TARTARIC ACID
TARTARIC ACID
Tartaric Acid market can be primarily divided into D-Tartaric acid, L-tartaric acid and DL Tataric acid.
DL-Tartaric Acid
EC / List no.: 205-105-7
CAS no.: 133-37-9
L(+) Tartaric Acid
EC / List no.: 201-766-0
CAS no.: 87-69-4
Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes, but also in bananas, tamarinds, and citrus.
Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation.
It is commonly mixed with sodium bicarbonate and is sold as baking powder used as a leavening agent in food preparation.
The acid itself is added to foods as an antioxidant E334 and to impart its distinctive sour taste.
DL-Tartaric acid has been used as food additives such as sour seasonings.
DL-Tartaric can also widely be used as industrial chemicals such as starting materials for detergents.
DL-Tartaric acid is a white, crystalline powder.
DL-Tartaric is mainly used in the food industry as an acidulant or ingredient producing emulsifier, and can be used as a starting material for pyruvate.
Its usage also covers the construction industry as a retarder, metal complexing agent for electroplating industry.
tartaric acid as an acidity regulator, adjuvant, anticaking agent, antioxidant, bulking agent, emulsifier, flour treatment agent, humectant, preservative, raising agent, sequestrant, stabilizer
L(+)-Tartaric Acid is a dicarboxylic acid available as white crystalline powder.
L(+)-Tartaric Acid can be used in areas below：
1） As acidulant, or ingredient producing emulsifier in food industry;
2） As retarder in construction industry;
3） As intermediate, resolving agent or salt-forming agent in pharmaceutical industry;
4） As complexing agent, chelating agent or antiscaling agent in electroplating and polishing industry;
5） As fruitacid in cosmetic industry.
D(-)-Tartaric acid is a white, crystalline acid which is widely used as intermediate or resolving agent in pharmaceutical industry.
DL-Tartaric Acid is white powder, Widely used in food industry, used as foaming agent of beer, acid taste agent, taste modified agent, and is mainly used to make tartaric acid salts, like potassium sodium tartrate, it can also be served as beer vesicant, food stuff sourness agent and flavoring etc.
DL-Tartaric Acid
EC / List no.: 205-105-7
CAS no.: 133-37-9
(±)-tartaric acid
IUPAC names
(+-)-Tartaric acid
(2R,3R)-2,3-dihydroxybutanedioic acid
2,3-Dihydroxybutanedioic Acid
2,3 dihydroxybutanedioic acid
2,3-Dihydroxybutanedioic acid
2,3-dihydroxybutanedioic acid
2,3-dihydroxysuccinic acid
Acide Tartrique Poudre
Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-
DL-Tartaric Acid
Tartaric acid
TARTARIC ACID ICSC: 0772
Racemic acid; uvic acid
DL-Tartaric acid
2,3-Dihydroxybutanedioic acid March 1996
CAS #: 133-37-9
EC Number: 205-105-7
L(+) Tartaric Acid
EC / List no.: 201-766-0
CAS no.: 87-69-4
Mol. formula: C4H6O6
(+)-(R,R)-Tartaric acid
(+)-tartaric acid
(+)-Tartaric acid
(+)-tartaric acid
(2R,3R)-(+)-Tartaric acid
1,2-Dihydroxyethane-1,2-dicarboxylic acid
2,3-Dihydroxybutanedioic acid
Acidum tartaricum
Butanedioic acid, 2,3-dihydroxy- (2R,3R)-
Cichoric acid
d-alpha,beta-Dihydroxysuccinic acid
Dextrotartaric acid
Kyselina 2,3-dihydroxybutandiova
Kyselina vinna
L-(+)-Tartaric acid
L-(+)-tartaric acid
l-Tartaric acid
Natural tartaric acid
Succinic acid, 2,3-dihydroxy
Tartaric acid
Tartaric acid (VAN)
Tartaric acid, L-(+)-
Threaric acid
Translated names
(+)-Borkősav (hu)
(+)-Kwas winowy (pl)
(+)-kyselina vinná (cs)
(+)-Tartaric acid (no)
(+)-viinhape (et)
(+)-Viinihappo (fi)
(+)-vinska kiselina (hr)
(+)-Vinska kislina (sl)
(+)-Vinsyra (sv)
(+)-vinsyre (da)
(+)-Vyno rūgštis (lt)
(+)-Vīnskābe (lv)
(+)-Weinsäure (de)
(+)-Wijnsteenzuur (nl)
(+)-Ácido tartárico (pt)
(+)-Τρυγικό οξύ (el)
(+)-Винена киселина (bg)
Acid (+)-tartric (ro)
Acide (+)-tartrique (fr)
Acido (+)-tartarico (it)
Aċidu (+)-tartariku (mt)
Kyselina (+)-vínna (sk)
Ácido (+)-tartárico (es)
CAS names
Butanedioic acid, 2,3-dihydroxy- (2R,3R)-
IUPAC names
(+) Tartaric acid
(+)-Tartaric acid
(+)-tartaric acid
(+)-tartaric acid
(2R,3R)-(+)-Tartaric acid
(2R,3R)-2,3-dihydroxybutanedioic acid
(2R,3R-2,3-Dihydroxybutandisäure
2,3-dihydroxy butanedioic acid
2,3-dihydroxybutanedioic acid
2,3-Dihydroxysuccinic acid
2,3-dihydroxysuccinic acid
Butanedioic acid, 2,3-dihydroxy- (2R,3R)-
Bórkősav
L(+) Tartaric Acid
L(+)-2,3-dihydrooxy butanedioic acid
L(+)-Tartaric acid
L-(+)-Tartaric Acid
L-(+)-Tartaric acid
L-(+)-tartaric acid
L-(+)-Tartaric acid
Tartaric acid (d,l)
Trade names
(+)-tartaric acid
Acide tartrique
Tartaric acid
Tartaric acid is an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics, and is a dihydroxyl derivative of succinic acid.
Tartaric acid has been known to winemakers for centuries.
However, the chemical process for extraction was developed in 1769 by the Swedish chemist Carl Wilhelm Scheele.
Tartaric acid played an important role in the discovery of chemical chirality.
This property of tartaric acid was first observed in 1832 by Jean Baptiste Biot, who observed its ability to rotate polarized light.
Louis Pasteur continued this research in 1847 by investigating the shapes of sodium ammonium tartrate crystals, which he found to be chiral.
By manually sorting the differently shaped crystals, Pasteur was the first to produce a pure sample of levotartaric acid.
Stereochemistry
Tartaric acid crystals drawn as if seen through an optical microscope
Naturally occurring tartaric acid is chiral, and is a useful raw material in organic chemical synthesis.
The naturally occurring form of the acid is dextrotartaric acid or L-(+)-tartaric acid (obsolete name d-tartaric acid).
Because it is available naturally, it is slightly cheaper than its enantiomer and the meso isomer.
The dextro and levo prefixes are archaic terms.
Modern textbooks refer to the natural form as (2R,3R)-tartaric acid (L-(+)-tartaric acid), and its enantiomer as (2S,3S)-tartaric acid (D-(-)-tartaric acid).
The meso diastereomer is (2R,3S)-tartaric acid (which is identical with ‘(2S,3R)-tartaric acid’).
Whereas the two chiral stereoisomers rotate plane polarized light in opposite directions, solutions of meso-tartaric acid do not rotate plane-polarized light.
The absence of optical activity is due to a mirror plane in the molecule
Tartaric acid in Fehling’s solution binds to copper(II) ions, preventing the formation of insoluble hydroxide salts.
Other names: Butanedioic acid, 2,3-dihydroxy-(R*,R*)-(.+/-.)-; Paratartaric acid; (.+/-.)-Tartaric acid; Paratartaric aicd; Racemic acid; Racemic tartaric acid; Resolvable tartaric acid; Tartaric acid, (DL)-; Tartaric acid, (.+/-.)-; Traubensaure; Uvic acid; Dihydroxysuccinic acid, (DL)-; dl-2,3-dihydroxybutanedioic acid; 2,3-Dihydroxysuccinic acid, (DL)-; (2RS,3RS)-Tartaric acid; Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-; Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-; NSC 148314; Tartaric acid; (±)-tartaric acid
Production
L-(+)-Tartaric acid
The L-(+)-tartaric acid isomer of tartaric acid is industrially produced in the largest amounts.
It is obtained from lees, a solid byproduct of fermentations.
The former byproducts mostly consist of potassium bitartrate (KHC4H4O6).
This potassium salt is converted to calcium tartrate (CaC4H4O6) upon treatment with milk of lime (Ca(OH)2):[18]
KO2CCH(OH)CH(OH)CO2H + Ca(OH)2 → Ca(O2CCH(OH)CH(OH)CO2) + KOH + H2O
In practice, higher yields of calcium tartrate are obtained with the addition of calcium chloride.
Calcium tartrate is then converted to tartaric acid by treating the salt with aqueous sulfuric acid:
Ca(O2CCH(OH)CH(OH)CO2) + H2SO4 → HO2CCH(OH)CH(OH)CO2H + CaSO4
Racemic tartaric acid
Racemic tartaric acid (i.e.: a 50:50 mixture of D-(−)-tartaric acid and L-(+)-tartaric acid molecules, racemic acid) can be prepared in a multistep reaction from maleic acid.
In the first step, the maleic acid is epoxidized by hydrogen peroxide using potassium tungstate as a catalyst.
HO2CC2H2CO2H + H2O2 → OC2H2(CO2H) 2
In the next step, the epoxide is hydrolyzed.
OC2H2(CO2H)2 + H2O → (HOCH)2(CO2H)2
meso-Tartaric acid
meso-Tartaric acid is formed via thermal isomerization. dextro-Tartaric acid is heated in water at 165 °C for about 2 days.
meso-Tartaric acid can also be prepared from dibromosuccinic acid using silver hydroxide:
HO2CCHBrCHBrCO2H + 2 AgOH → HO2CCH(OH)CH(OH)CO2H + 2 AgBr
meso-Tartaric acid can be separated from residual racemic acid by crystallization, the racemate being less soluble.
Reactivity
L-(+)-tartaric acid, can participate in several reactions.
As shown the reaction scheme below, dihydroxymaleic acid is produced upon treatment of L-(+)-tartaric acid with hydrogen peroxide in the presence of a ferrous salt.
HO2CCH(OH)CH(OH)CO2H + H2O2 → HO2CC(OH)C(OH)CO2H + 2 H2O
Dihydroxymaleic acid can then be oxidized to tartronic acid with nitric acid.[20]
Derivatives
Tartar emetic
Commercially produced tartaric acid
Important derivatives of tartaric acid include its salts, cream of tartar (potassium bitartrate), Rochelle salt (potassium sodium tartrate, a mild laxative), and tartar emetic (antimony potassium tartrate).
Diisopropyl tartrate is used as a co-catalyst in asymmetric synthesis.
Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death.
The median lethal dose (LD50) is about 7.5 grams/kg for a human, 5.3 grams/kg for rabbits, and 4.4 grams/kg for mice.
Given this figure, it would take over 500 g (18 oz) to kill a person weighing 70 kg (150 lb), so it may be safely included in many foods, especially sour-tasting sweets.
As a food additive, tartaric acid is used as an antioxidant with E number E334; tartrates are other additives serving as antioxidants or emulsifiers.
When cream of tartar is added to water, a suspension results which serves to clean copper coins very well, as the tartrate solution can dissolve the layer of copper(II) oxide present on the surface of the coin. The resulting copper(II)-tartrate complex is easily soluble in water.
Tartaric acid in wine
See also: Acids in wine and Tartrate
Unpurified potassium bitartrate can take on the color of the grape juice from which it was separated.
Tartaric acid may be most immediately recognizable to wine drinkers as the source of “wine diamonds”, the small potassium bitartrate crystals that sometimes form spontaneously on the cork or bottom of the bottle.
These “tartrates” are harmless, despite sometimes being mistaken for broken glass, and are prevented in many wines through cold stabilization (which is not always preferred since it can change the wine’s profile).
The tartrates remaining on the inside of aging barrels were at one time a major industrial source of potassium bitartrate.
Tartaric acid plays an important role chemically, lowering the pH of fermenting “must” to a level where many undesirable spoilage bacteria cannot live, and acting as a preservative after fermentation.
In the mouth, tartaric acid provides some of the tartness in the wine, although citric and malic acids also play a role.
Tartaric acid in citrus
Results from a study showed that in citrus, fruits produced in organic farming contain higher levels of tartaric acid than fruits produced in conventional agriculture.
In superconductors
Tartaric acid seems to increase the critical temperature in certain superconductors, by supposedly raising the oxidation grade, while the mechanism of this phenomenon is still not precisely known.[27]
Applications
Tartaric acid and its derivatives have a plethora of uses in the field of pharmaceuticals.
For example, it has been used in the production of effervescent salts, in combination with citric acid, to improve the taste of oral medications.[20] The potassium antimonyl derivative of the acid known as tartar emetic is included, in small doses, in cough syrup as an expectorant.
Tartaric acid also has several applications for industrial use. The acid has been observed to chelate metal ions such as calcium and magnesium.
Therefore, the acid has served in the farming and metal industries as a chelating agent for complexing micronutrients in soil fertilizer and for cleaning metal surfaces consisting of aluminium, copper, iron, and alloys of these metals, respectively.[18]
Synonyms: DL-2,3-Dihydroxybutanedioic acid
CAS No. 133-37-9, 526-83-0
DL-Tartaric Acid (2,3-Dihydroxysuccinic acid) is a white, crystalline organic acid isolated from many plants, particularly tamarinds and grapes and is used as an antioxidant and an additive agent to give a sour taste.
Tartaric acid is a white crystalline diprotic organic acid.
The compound occurs naturally in many plants, particularly in grapes, bananas, and tamarinds.
It is also one of the main acids found in wine.
Tartaric acid can be added to food when a sour taste is desired.
It is also used as an antioxidant. Salts of tartaric acid are known as tartarates.
The chemical is a dihydroxy derivative of succinic acid.
Tartaric acid is found in cream of tartar and baking powder.
The chemical compound is used in silvering mirrors, tanning leather, and in Rochelle Salt.
In medical analysis, tartaric acid is used to make solutions for the determination of glucose.
Tartaric acid is a white, crystalline organic acid anti-inflammatory and anti-oxidant properties that occurs naturally in many fruits.
These properties help to stimulate overall helps to boost individual’s immune systems.
Tartaric acid is a dicarboxylic acid, which is notably found in different fruits such as grapes, bananas, tamarind and citrus.
It is also obtained from wine fermentation by-products by salts, potassium bitartrate, also known as tartar cream.
Tartaric acid is an important ingredient in bakery items where, when mixed with baking powder, it acts as a leavening agent.
It also improves fruit flavours and in baked goods stabilizes batter structures and colour.
Tartaric acid extracts serve as buffers in the winemaking cycle to control antioxidant E334, acidity and preservatives; in other food items, they act as natural flavour enhancers and food emulsifiers.
DL-Tartaric acid
Agent Name: DL-Tartaric acid
CAS Number: 133-37-9
Formula: C4-H6-O6
Major Category
Other Classes: DL-Tartaric acid formula graphical representation
Synonyms: (+-)-Tartaric acid; (2RS,3RS)-Tartaric acid; Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-; DL-Tartrate; Paratartaric acid; Racemic acid; Racemic tartaric acid; Resolvable tartaric acid; Tartaric acid D,L; Traubensaure; Uvic acid; dl-Tartaric acid; Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-; Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-(+-)-; Butanedioic acid, 2,3-dihydroxy-, (theta,theta)-(+-)-; [ChemIDplus] dl-Weinsaure (German); Vogesensaure (German); [Merck Index]
Category: Organic Acids
Description: White solid; [ICSC] Colorless or white odorless solid; [JECFA] White odorless crystalline powder; [Acros Organics MSDS]
Sources/Uses
Used as a synergist for antioxidants, acid, emulsifier, sequestrant, and flavoring agent; [JECFA]
Comments
Causes burns; Inhalation of aerosol may cause pulmonary edema; [ICSC] An irritant; [Acros Organics MSDS]
Tartaric Acid, also called dihydroxysuccinic acid [HOOC(CHOH)2COOH]), is a white crystalline naturally occurring carboxylic acid; melting at 171 C, soluble in water and alcohols.
It is obtained natually as a by-products of wine fermentation along with its salts.
This natural acid is used as an antioxidant in food.
Tartaric acid has two asymmetrical carbon atoms and three chiral isomers; the dextro-, levo-, (optically active) and meso- forms (optically inactive).
The d- and l-tartaric acids are said to be enantiomorphs (each molecule is asymmetrical and has the mirror image of the other).
There are two asymmetrical carbon atoms in meso-tartaric acid, but the molecule is symmetrical and does not exhibit optical activity; the optical activity is internally compensated, the effect of one asymmetrical carbon atom balancing the effect of the other.
A pair of optical isomers such as d-tartaric acid and meso-tartaric acid, which are not enantiomorphs, are called diastereoisomers. Tartaric Acid is a useful raw material for the synthesis of other chiral compounds.
L-tartaric acid (called also d-2,3-dihydroxysuccinic acid or l-2,3-dihydroxybutanedioic acid) is chiefly found in many plant especially grape.
This form can be partially converted to the others by heating it with an aqueous alkali (potassium hydroxide) as the isomeric forms differ from each other in boiling points.
It can be synthesized by the reaction of maleic acids or fumaric acids with aqueous potassium permanganate.
Tartaric acid is biodegradable and no pollution problems are known.
Tartaric acid is used chiefly in the form of its salts, e.g., cream of tartar (potassium hydrogen tartrate), Rochelle salt (potassium sodium tartrate) and Tartar Emetic (antimony potassium tartrate).
It is used to enhance flavours in foods, confectionery and beverages.
It is used as a chemical intermediate and a sequestrant and in tanning, ceramics, photography, textile processing, mirror silvering, and metal coloring.
CAS No.133-37-9
Chemical Name:DL-Tartaric acid
Synonyms: Uvic acid;Sal tartar;DL-Tartaric;DL-TARTRATE;DL-Weinsαure;Traubensaure;Traubensαure;Vogesensαure;RACEMIC ACID;TARTARIC ACID
Tartaric Acid is synergist for antioxidants, acids, emulsifiers, sequestrants, flavoring agents
FUNCTIONAL USES
Synergist for antioxidants, acid, emulsifier, sequestrant, flavouring agent
Solubility
Freely soluble in water; sparingly soluble in ethanol
Applications
Tartaric acid and its derivatives have a plethora of uses in the field of pharmaceuticals.
It has been used in the production of effervescent salts, in combination with citric acid, in order to improve the taste of oral medications.
The potassium antimonyl derivative of the acid known as tartar emetic is included, in small doses, in cough syrup as an expectorant.
Melting range
200 – 206 with decomposition when heated rapidly in a sealed capillary tube
substances
N potassium permanganate while keeping the solution at 20o . The colour of the solution does not disappear within 3 min.
METHOD OF ASSAY
Weigh accurately about 2 g of the dried sample, dissolve it in 40 ml of water, add phenolphthalein TS, and titrate with 1 N sodium hydroxide.
Each ml of 1 N sodium hydroxide is equivalent to 75.04 mg of C4H6O6.
Chemical Properties
Tartaric acid, HOOC(CHOH)2COOH, is a water- and alcohol-soluble colorless crystalline solid with an acid taste and a melting temperature of 170°C (338 OF).
It is also known as dihydroxy succinic acid.
Tartaric acid is used as a chemical intermediate and a sequestrant,as well as in tanning, effervescent beverages, baking powder, ceramics, photography, textile processing, mirror silvering, and metal coloring.
Chemical Properties
Tartaric acid is odorless, but has a characteristic acid taste.
Naturally occurring tartaric acid is generally of the L-configuration (based on the absolute configuration of D-glyceric acid).
The L-forms of tartrates are dextrorotatory in solution and thus are designated as L(+)-tartrates.
For a detailed description on this chemical, refer to Burdock (1997).
Occurrence
d-Tartaric acid occurs in many fruits or other parts of the plant, free or combined with potassium, calcium or magnesium.
It is also reported found in raw, lean fish, white wine, red wine and port wine.
Preparation
The tartrates used in commerce are obtained as a by-product of wine manufacture and have the L(+) configuration.
Produced from argols or wine lees, which are formed in the manufacture of wine by extracting the potassium acid tartrate, transforming this into the calcium salt and then acidifying with dilute sulfuric acid; also by oxidation of d-glucose with nitric acid.
The dl-tartaric acid is obtained by boiling the d-tartaric acid with an aqueous solution of NaOH or by oxidation of fumaric acid.
The l- and the meso-tartaric acid are also known, but are less important.
DL-Tartaric acid Preparation Products And Raw materials
Raw materials
CALCIUM TARTRATE Tungstic acid Maleic acid Maleic anhydride Hydrogen peroxide Sodium pyruvate (+/-)-TRANS-EPOXYSUCCINIC ACID D(-)-Tartaric acid CIS-EPOXYSUCCINIC ACID
Preparation Products
L(+)-Diethyl L-tartrate Potassium tartrate Disodium tartrate dihydrate L-Antimony potassium tartrate Ammonium L-tartrate Pyruvic acid Kitasamycin tartrate Potassium sodium tartrate (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester Potassium Bitartrate 4-Hydroxy-D-(-)-2-phenylglycine
Tartaric acid is a white crystalline organic acid that occurs naturally in many plants, most notably in grapes.
Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of winemaking.
Naturally occurring tartaric acid is chiral, and is a useful raw material in organic chemical synthesis.
The naturally occurring form of the acid is dextrotartaric acid or D-(-)-tartaric acid.
Applications
1. DL – TARTARIC ACID is widely used as beverages and other food acidifier, similar to the use and citric acid.
Combination of tartaric acid and tannin can be used as mordant acid dyes, but also for the photographic industry, and the fixation of certain imaging operations, which have a photosensitive iron salts, it can be used to produce a blueprint
2. DL – Tartaric acid with a variety of metal ions complexation can be used for metal surface cleaning agents and polishing agents
3. Potassium sodium tartrate (Rochelle salt) can be prepared Fehling, but also used in medicine as laxatives and diuretics, but also as a Sims can be fun intermediates
4. The crystal has piezoelectric properties can be used for the electronics industry
5. DL – TARTARIC ACID (CAS NO.147-71-7) is used for chromatographic analysis of reagent and a masking agent. And it also used as split agent for pharmaceutical, food additives, chemical and biological reagents
6. This product is widely used in food industry, such as beer foam, food sour agent, Jiao flavor agent and used in soft drinks, candy, fruit juice, sauces, cold dish, and baking powder and so on. This product is in line with Japanese food additives Kimisada book
DL Tartaric Acid is a colorless and semi-transparent or white powder, with a sour taste.
It is widely used in many fields such as foodstuff, medicine, the chemical and light industries etc., and is mainly used to make tartrates (tartaric acid salts), like antimony potassium tartrate, and potassium sodium tartrate.
It can be used as a beer vesicant, foodstuff sourness agent, and flavoring etc.
Its sourness is 1.3 times of that of citric acid, and it is especially suitable to be a sourness agent of grape juice.
It is also very important for the tannage, photograph, glass, enamel and telecommunication equipment industries.
Tartaric Acid is a white crystalline dicarboxylic acid found in many plants, particularly tamarinds and grapes.
Tartaric acid is used to generate carbon dioxide through interaction with sodium bicarbonate following oral administration.
Carbon dioxide extends the stomach and provides a negative contrast medium during double contrast radiography.
Tartaric acid is an organic acid naturally found in fruits including grapes and tamarind.
It is a principal ingredient in wine and provides it with the characteristic tart taste.
Tartaric acid is primarily manufactured from natural raw materials; however, it can also be manufactured synthetically from maleic anhydride. Tartaric acid finds applications in the wine, food & beverages, construction, pharmaceutical, chemical, leather tanning, and metal finishing industries. It is used as an acidulant, pH control, and flavorant in wine. Tartaric acid is also used as an anti-microbial agent, anti-caking agent in bakery items and flavorant for fruit juices in the food & beverages industry. In the pharmaceutical industry, it is used as an excipient for drugs with poor solubility at higher pH levels. Tartaric acid is used as an anti-set agent in cement formulations in the construction industry.
DL tartaric acid is very useful in many applications,
· Tartaric Acid is widely used as antioxidant and acidity regulator in food production.
As antioxidant: in canned food to maintain flavor and appearance.
As acidity regulator: in canned food and confectionery to improve flavor.
· Beverage
Dl Tartaric Acid is widely used as antioxidant and acidity regulator in beverage.
As acidity regulator: in soft drink to improve flavor.
· Pharmaceutical
Dl Tartaric Acid is widely used as intermediate in Pharmaceutical.
As intermediate: in medicine manufacturing.
· Cosmetics
· Agriculture/Animal Feed
· Other Industries
Dl Tartaric Acid is widely used as antioxidant in various other industries.
As antioxidant: in leather processing to soften leather.
Tartaric acid is used in silvering mirrors, tanning leather, and in the making of Rochelle salt, which is sometimes used as a laxative.
Salts of Tartaric
Salts of tartaric acid are known as tartrates. It is a dihydroxyl derivative of succinic acid.
1. (R*, R*)-(+-)-2,3-dihydroxybutanedioic acid, Monoammonium Monosodium Salt
2. Aluminium Tartrate
3. Ammonium Tartrate
4. Calcium Tartrate
5. Calcium Tartrate Tetrahydrate
6. Mn (III) Tartrate
7. Potassium Tartrate
8. Seignette Salt
9. Sodium Ammonium Tartrate
10. Sodium Potassium Tartrate
11. Sodium Tartrate
12. Stannous Tartrate
13. Tartaric Acid
14. Tartaric Acid, ((R*, R*)-(+-))-isomer
15. Tartaric Acid, (R*, S*)-isomer
16. Tartaric Acid, (R-(R*, R*))-isomer
17. Tartaric Acid, (S-(R*, R*))-isomer
18. Tartaric Acid, Ammonium Sodium Salt, (1:1:1) Salt, (R*, R*)-(+-)-isomer
19. Tartaric Acid, Calcium Salt, (R-R*, R*)-isomer
20. Tartaric Acid, Monoammonium Salt, (R-(R*, R*))-isomer
Tartaric acid is also use as a preservative in packaged foods coupled with growing use across various end-user industries, such as food & beverages, pharmaceuticals as it acts as an emulsifier and chelating agent.
Moreover, the rising adoption of tartaric acid in antacids will drive the growth of the market further.
Based on the type of tartaric acid, synthetic segment is expected to hold the largest market share as tartaric acid produced in the country is chemically synthesised.
Based on the application, food & beverage is expected to lead the market in the next five years owing to the widespread applications of tartaric acid as emulsifier and preservative in packaged foods, bakery items, soft-drinks etc.
Increasing demand from the wine industry in the Asia-Pacific and Latin American regions, coupled with the growing demand for packaged food, is expected to drive the market during the forecast period.
The market is primarily driven by the diverse uses of tartaric acid in the food & beverage industry.
Owing to the changing lifestyles, the growing demand for packaged food in developing economies around the world is expected to boost market growth during the forecast period.
Tartaric acid is widely used in the pharmaceutical segment.
This is owing to its characteristic property of enhancing the taste of medicine, making it the material of choice for use in the pharmaceutical industry.
Tartaric acid and its derivatives are widely used in making effervescent salts, which are formed when combined with citrates.
The pharmaceutical industry is expected to be the one of the fastest growing segments by end-user industry in the global tartaric acid market due to the rise in medicine demand globally.
The natural tartaric acid segment is projected to be the fastest-growing during the forecast period, due to its high usage in applications such food & beverages, especially in the wine industry, resulting in an exponential increase in the consumption and production.
Tartaric acid is mostly used in the wine industry due to the major role it plays in maintaining the chemical stability of the wine, controlling the acidity of wine and its color, and finally in influencing the taste of the finished wine.
DESCRIPTION
In general, where biological molecules have optical isomers, only one of the isomers or forms will be active biologically.
The other will be unaffected by the enzymes in living cells. The meso form of the molecule is not affected by polarized light.
The fourth form — the DL mixture, is not a single molecule, but a mixture of equal amounts of D and L isomers.
It does not rotate polarized light (like the meso form) because the rotation of light by the D and L forms is equal in amount but opposite in direction.
It is possible to separate the DL mixture into the two isomers, each of which does rotate light.
In the 1840s, Louis Pasteur determined that each of the two isomers of tartaric acid rotated light in opposite directions, and the meso form was inactive in this respect.
He also separated by hand, crystals of the racemic mixture to show that it was made of equal amounts of the D and L forms, making it different than the meso form of tartaric acid.
Applications
Tartaric acid is found in cream of tartar, which is used in making candies and frostings for cakes.
Tartaric acid is also used in baking powder where it serves as the source of acid that reacts with sodium bicarbonate (baking soda). This reaction produces carbon dioxide gas and lets products “rise,” but it does so without the “yeast” taste that can result from using active yeast cultures as a source of the carbon dioxide gas.
Tartaric acid is used in silvering mirrors, tanning leather, and in the making of Rochelle Salt, which is sometimes used as a laxative.
Blue prints are made with ferric tartarte as the source of the blue ink.
In medical analysis, tartaric acid is used to make solutions for the determination of glucose.
Common esters of tartaric acid are diethyl tartarate and dibutyl tartrate. Both are made by reacting tartaric acid with the appropriate alcohol, ethanol or n-butanol.
In the reaction the Hydrogen of the COOH acid group is replaced with an ethyl group (diethyl tartarate) or butyl group (dibutyl tartarate.
These esters are used in manufacturing lacquer and in dyeing textiles.
• (2S,3S)-2,3-dihydroxybutane-1.4-dioicacid
• 2,3-dihydroxy-,(R*,R*)-(±)-Butanedioicacid
• DL-Tartaric acid 133-37-9 pure 99% food additives Paratartaric acid kf-wang(at)kf-chem.com
• 2,3-dihydroxybutanedioic acid hydrate
• DL-Tartaric acid/2,3-Dihydroxysuccinic acid
• Clopidogrel Impurity 45
• Tartaric acid kf-wang(at)kf-chem.com
• 2,3-dihydroxy-,(theta,theta)-(+/-)-butanedioicaci
• Butanedioic acid, 2,3-dihydroxy-(R*,R*)-(.+/-.)-
• Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-(±
• dl-Tartaric acid anhydrous
• DL-Weinsαure
• Paratartaric acid
• Paratartaric aicd
• Racemic tartaric acid
• Racemictartaricacid
• DL-Tartaric
• Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-
• D/ DL-Tartaric acid
• DL-TARTRATE
• DL-2,3-Dihydroxysuccinicacid
• Ordinay tartaric acid
• DL-TARTARIC ACID ANHYDROUS, FOR ION CHROMATOGRAPHY
• DL-TARTARIC ACID SOL.,ELUENT CONCENTRATE FOR IC, 0.1M IN WATER
• Dl-TartaricAcid(Synthetic)
• DL-TARTARIC ACID extra pure
• DL-Tartaric acid, 99.50%
• DL-TARTARIC ACID, 99% ANHYDROUS
• DL-2,3-Dihydroxybutanedioic acid solution
• DL-Tartaric acid solution
• DL-tartaric acid, 99.5%
• DL-Tartaric acid, 99.5% 100GR
• DL-TARTARIC ACID, 99%, ANHYDROUSDL-TARTARIC ACID, 99%, ANHYDROUSDL-TARTARIC ACID, 99%, ANHYDROUSDL-TARTARIC ACID, 99%, ANHYDROUS
• racemischeWeinsαure
• Resolvable tartaric acid
• Sal tartar
• Tartaric acid D,L
• Traubensaure
• Traubensαure
• Uvic acid
• Vogesensαure
• TARTARIC ACID
• RACEMIC ACID
• DL-TARTARIC ACID
• dl-dihydroxysuccinic acid
• DL-2,3-DIHYDROXYBUTANEDIOIC ACID
• DL-Tartaric acid ReagentPlus(R), 99%
• DL-Tartaric ac
• DL-Tartaric acid concentrate
• DL-Tartaric acid Vetec(TM) reagent grade, 99%
• (2R,3R)-rel-2,3-Dihydroxysuccinic acid
• TARTARIC ACID (D-, L-, DL-, MESO-)
• Tartaric acid, 99.5%
• DL-Tartaric Acid >
• DL-WEINSAEURE 500 G
• high purity DL-Tartaric acid
• Tartaric Acid Impurity 1 (DL-Tartaric Acid )
• DL-TartaricAci
Synonyms:
(2R,3R)-rel-2,3- dihydroxybutane dioic acid
(R*,R*)-(±)-2,3- dihydroxybutane dioic acid
(theta,theta)-(±)-2,3- dihydroxybutane dioic acid
(±)-2,3- dihydroxybutanedioic acid
racemic acid
(±)- tartaric acid
(2RS,3RS)- tartaric acid
DL- tartaric acid
racemic tartaric acid
para tartaric aicd
DL- tartaric aicd natural
traubensaure
uvic acid
(±)-Tartaric acid
2,3-Dihydroxybernsteinsäure [German] [ACD/IUPAC Name]
2,3-dihydroxybutanedioic acid
2,3-dihydroxysuccinic acid
2,3-Dihydroxy-succinic acid
212-425-0 [EINECS]
815-82-7 [RN]
Acide tartrique [French] [ACD/IUPAC Name]
Butanedioic acid, 2,3-dihydroxy- [ACD/Index Name]
DL-Tartaric acid
MFCD00064206 [MDL number]
Tartaric acid [ACD/IUPAC Name] [JP15] [NF] [Trade name] [Wiki]
Tartaric acid, (±)-
Tartaric acid, (DL)-
TARTARIC ACID, D-
TARTARIC ACID, DL-
TARTARIC ACID, MESO-
Tartarsäure [German]
(+)-tartarate
(+)-Weinsaeure
(±)-tartaric acid
(±)-Tartaric Acid
(1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylic acid
(2R,3R)-2,3-Dihydroxybernsteinsaeure
(2R,3R)-2,3-dihydroxybutanedioate
(2R,3R)-2,3-dihydroxybutanedioic acid
(2R,3R)-2,3-tartaric acid
(2R,3R)-rel-2,3-Dihydroxysuccinic acid
(2R,3R)-Tartarate
(2RS,3RS)-Tartaric acid
(2S,3S)-2,3-Dihydroxysuccinic acid [ACD/IUPAC Name]
(R,R)-tartarate
1,2-DIHYDROXYETHANE-1,2-DICARBOXYLIC ACID
1-Aminoheptadecane
2-(2-oxanyloxy)isoindole-1,3-dione
2, 3-Dihydrosuccinic acid
2,3-dihydroxysuccinic acid
2,3-dihydrosuccinic acid
2,3-dihydroxybutanedioate
2,3-dihydroxy-succinate
2,3-Dihydroxysuccinic acid, (DL)-
205-696-1 [EINECS]
2-Tetrahydropyran-2-yloxyisoindoline-1,3-dione
3-Carboxy-2,3-dihydroxypropanoate [ACD/IUPAC Name]
3-Carboxy-2,3-dihydroxypropanoic acid
868-14-4 [RN]
91469-46-4 [RN]
acide tartarique
Acidum tartaricum
Butanedioic acid, 2,3-dihydroxy- {[R-(R*,R*)]-}
Cremor tartari
d-a,b-Dihydroxysuccinic Acid
DB09459
dextro,laevo-tartaric acid
Dihydroxysuccinic acid, (DL)-
DL-2,3-Dihydroxybutanedioic acid
dl-tartaric acid-gr
dl-tartaricacid
dl-tartrate
http:////www.amadischem.com/proen/573971/
http:////www.amadischem.com/proen/594359/
http:////www.amadischem.com/proen/595007/
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15674
Kyselina 2,3-dihydroxybutandiova [Czech]
Kyselina vinna [Czech]
Kyselina vinna
L-tartarate
Malic acid, 3-hydroxy-
MFCD00004238 [MDL number]
MFCD00064207 [MDL number]
MFCD00071626 [MDL number]
MFCD00151254 [MDL number]
Natrol
Paratartaric acid
Rechtsweinsaeure
Resolvable tartaric acid
Succinic acid, 2, 3-dihydroxy
Succinic acid, 2,3-dihydroxy
Succinic acid, 2,3-dihydroxy-
TAR
Tartar cream
Tartarate [ACD/IUPAC Name]
Tartaric acid, (±)-
Tartaric acid, (l)
Tartrol
THREARIC ACID
TLA
Traubensaure
Uvic acid
Weinsaeure
Weinsteinsaeure
WLN: QVYQYQVQ
酒石酸 [Chinese]
Tartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes and tamarinds, and is one of the main acids found in wine.
It is added to other foods to give a sour taste, and is used as an antioxidant. Salts of tartaric acid are known as tartrates.
It is a dihydroxy derivative of dicarboxylic acid.
Tartaric acid was first isolated from potassium tartrate, known to the ancients as tartar, c. 800 by the Persian alchemist Jabir ibn Hayyan, who was also responsible for numerous other basic chemical processes still in use today.
The modern process was developed in 1769 by the Swedish chemist Carl Wilhelm Scheele.
The chirality of tartaric acid was discovered in 1832 by Jean Baptiste Biot, who observed its ability to rotate polarized light.
Louis Pasteur continued this research in 1847 by investigating the shapes of tartaric acid crystals, which he found to be asymmetric.
Pasteur was the first to produce a pure sample of levotartaric acid.
Stereochemistry
Naturally-occurring tartaric acid is chiral, meaning that it has molecules that are non-superimposable on their mirror-images.
It is a useful raw material in organic chemistry for the synthesis of other chiral molecules.
The naturally occurring form of the acid is L-(+)-tartaric acid or dextrotartaric acid.
The mirror-image (enantiomeric) form, levotartaric acid or D-(−)-tartaric acid, and the achiral form, mesotartaric acid, can be made artificially.
Note, that the dextro and levoprefixes are not related to the D/L configuration (which is derived from the reference D- or L-glyceraldehyde), but to the orientation of the optical rotation, (+) = dextrorotatory, (−) = levorotatory.
Sometimes, instead of capital letters, small italic d, l are used.
They are abbreviations of dextro- and levo-, and nowadays should not be used.
Levotartaric and dextrotartaric acid are enantiomers, mesotartaric acid is a diastereomer of both of them.
A rarely occurring optically inactive form of tartaric acid, DL-tartaric acid is a 1:1 mixture of the levo and dextroforms.
It is distinct from mesotartaric acid and was called racemic acid (from Latin racemus – “a bunch of grapes”).
The word racemic later changed its meaning, becoming a general term for 1:1 enantiomeric mixtures – racemates.
Important derivatives of tartaric acid include its salts, Cream of tartar (potassium bitartrate), Rochelle salt (potassium sodium tartrate, a mild laxative) and tartar emetic (antimony potassium tartrate).
Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death.
The minimum recorded fatal dose for a human is about 12 grams. In spite of that, it is included in many foods, especially sour-tasting sweets.
As a food additive, tartaric acid is used as an antioxidant with E number E334, tartrates are other additives serving as antioxidants or emulsifiers.
When cream of tartar is added to water, a suspension results which serves to clean copper coins very well.
This is due to the fact that the tartrate solution can dissolve the layer of copper(II) oxide present on the surface of the coin.
Copper(II)-tartrate complex that is formed is easily soluble in water. Tartaric acid in wine
Tartaric acid may be most immediately recognizable to wine drinkers as the source of “wine diamonds,” the small potassium bitartrate crystals that sometimes form spontaneously on the cork.
These “tartrates” are harmless, despite sometimes being mistaken for broken glass, and are prevented in many wines through cold stabilization.
The tartrates that remain on the inside of aging barrels were at one time a major industrial source of potassium bitartrate.
However, tartaric acid plays an important role chemically, lowering the pH of fermenting “must” to a level where many undesirable spoilage bacteria cannot live, and acting as a preservative after fermentation.
In the mouth, tartaric acid provides some of the tartness that is currently out of fashion in the wine world, although citric and malic acids also play a role.
The modern practice of extended hang time, where grapes are allowed to sit on the vine nearly until they become raisins, can dramatically reduce the taste of tartaric acid in a wine, leaving it smoother but also potentially less compatible with food
Tartaric Acid
Tartaric acid is one of the least antimicrobial of the organic acids known to inactivate fewer microorganisms and inhibit less microbial growth in comparison with most other organic acids (including acetic, ascorbic, benzoic, citric, formic, fumaric, lactic, levulinic, malic, and propionic acids) in the published scientific literature.
Tartaric acid (2,3-dihydroxybutanedioic acid) is a naturally occurring dicarboxylic acid containing two stereocenters.
Tartaric acid has a stronger, sharper taste than citric acid.
Although it is renowned for its natural occurrence in grapes, it also occurs in apples, cherries, papaya, peach, pear, pineapple, strawberries, mangos, and citrus fruits.
Tartaric acid is used preferentially in foods containing cranberries or grapes, notably wines, jellies, and confectioneries.
Commercially, tartaric acid is prepared from the waste products of the wine industry and is more expensive than most acidulants, including citric and malic acids.
Tartaric acid is one of the least antimicrobial of the organic acids known to inactivate fewer microorganisms and inhibit less microbial growth in comparison with most other organic acids (including acetic, ascorbic, benzoic, citric, formic, fumaric, lactic, levulinic, malic, and propionic acids) in the published scientific literature.
Furthermore, when dissolved in hard water, undesirable insoluble precipitates of calcium tartrate can form.
l-Tartaric acid is an abundant constituent of many fruits such as grapes and bananas and exhibits a slightly astringent and refreshing sour taste. It is one of the main acids found in wine. It is added to other foods to give a sour taste and is normally used with other acids such as citric acid and malic acid as an additive in soft drinks, candies, and so on. It is produced by acid hydrolysis of calcium tartrate, which is prepared from potassium tartrate obtained as a by-product during wine production. Optically active tartaric acid is used for the chiral resolution of amines and also as an asymmetric catalyst.
Tartaric Acid
Tartaric acid is the most water-soluble of the solid acidulants. It contributes a strong tart taste that enhances fruit flavors, particularly grape and lime. This dibasic acid is produced from potassium acid tartrate, which has been recovered from various by-products of the wine industry, including press cakes from fermented and partially fermented grape juice, lees (the dried, slimy sediments in wine fermentation vats), and argols (the crystalline crusts formed in vats during the second fermentation step of wine making). The major European wine-producing countries, Spain, Germany, Italy, and France, use more of the acid than the United States.
Tartaric acid is often used as an acidulant in grape- and lime-flavored beverages, gelatin desserts, jams, jellies, and hard sour confectionery. The acidic monopotassium salt, more commonly known as ‘cream of tartar,’ is used in baking powders and leavening systems. Because it has limited solubility at lower temperatures, cream of tartar does not react with bicarbonate until the baking temperatures are reached; this ensures maximum development of volume in the finished product.
Grapes contribute tartaric and malic acids to wines. Tartaric acid concentration varies during grape ripening, and is more related to climatic conditions than varietal character. Tartrate precipitation during maturation decreases wine contents to 0.445–1.688 g l−1, independent of age or wine type.
In contrast, malic acid contents, more dependent on grape variety than climate, fall during ripening. Contents are lower in younger port wines, than older, possibly through later picking in recent vintages.
Lactic acid, formed by strain-dependent anaerobic yeast metabolism, is present in port wines in the range 0.3–1.68 g l−1, independent of wine age.
Tartaric Acid is a white crystalline dicarboxylic acid found in many plants, particularly tamarinds and grapes. Tartaric acid is used to generate carbon dioxide through interaction with sodium bicarbonate following oral administration. Carbon dioxide extends the stomach and provides a negative contrast medium during double contrast radiography. In high doses, this agent acts as a muscle toxin by inhibiting the production of malic acid, which could cause paralysis and maybe death.
NCI Thesaurus (NCIt)
2,3-dihydroxybutanedioic acid is a tetraric acid that is butanedioic acid substituted by hydroxy groups at positions 2 and 3. It has a role as a human xenobiotic metabolite and a plant metabolite. It is a conjugate acid of a 3-carboxy-2,3-dihydroxypropanoate.
Chemical Names:
2,3-dihydroxybutanedioic acid
Other Name:
2,3-dihydroxysuccinic acid
Thearic acid
Uvic acid
L(+) tartaric acid
D(-) tartaric acid
Mesotartaric acid
Racemic acid
Trade Names:
CAS Numbers:
L(+) tartaric acid: 87-69-4
D(-) tartaric acid: 147-71-7
Mesotartaric acid: 147-73-9
Racemic acid: 133-37-9
Other Codes:
L(+) tartaric acid: 205-695-6
D(-) tartaric acid: 201-766-0
Mesotartaric acid: 205-696-1
Racemic acid: 205-105-7
Characterization of Petitioned Substance
Composition of the Substance:
Tartaric acid [HOOCCH(OH)CH(OH)COOH; C4H6O6] is a four-carbon, organic acid with two OH groups on the second and third carbon atoms, and two carboxylic acid (COOH) groups involving the first and fourth carbons
The form of tartaric acid found naturally in grapes and often produced synthetically for use in handling is the L(+) tartaric acid isomer.
This form is generally referred to as the ‘dextro form’ (Church and Blumberg,28 1951).
The D(-) form of tartaric acid is less common in nature and has almost no practical uses.
The third form is an achiral isomer, mesotartaric acid, that also can be manufactured
Properties of the Substance:
An organic acid, tartaric acid is an odorless, white crystalline solid (Smith and Hong-Shum, 2008).
The substance has a strong, tart taste and contributes to the flavors of many fruits (Furia, 1972).
It has a high Ka (acid-dissociation equilibrium constant; measure of the strength of acidity) and possesses microbial stability.
It is found naturally in plants including grapes, bananas, and tamarinds
Specific Uses of the Substance:
Tartaric acid is a natural organic acid that is in many plants especially grapes, bananas, and tamarinds.
Tartaric acid can be used to create several different salts, including tartar emetic (antimony potassium tartrate), cream of tartar (potassium hydrogen tartrate), and Rochelle salt (potassium sodium tartrate).
The primary uses of tartaric acid are associated with its salts (The Chemical Company, 2010).
Tartaric acid and its salts have a very wide variety of uses. These include use as an acidulant, pH control agent, preservative, emulsifier, chelating agent, flavor enhancer and modifier, stabilizer, anti-caking agent, and firming agent.
It has been used in the preparation of baked goods and confectionaries, dairy products, edible oils and fats, tinned fruits and vegetables, seafood products, meat and poultry products, juice beverages and soft drinks, sugar preserves, chewing gum, cocoa powder, and alcoholic drinks.
As an acidulant and flavoring agent, tartaric acid is known to enhance the flavors of the fruits in which it is a natural derivative.
Tartaric acid is commonly used to enhance grape flavors and to enhance flavors associated with raspberry, oranges, lemon, gooseberry, and currant.
Tartaric acid and its immediate byproducts are particularly useful in baking.
Due to its acidic properties,tartaric acid is used in baking powder in combination with baking soda (sodium bicarbonate).
When tartaric acid reacts with sodium bicarbonate, carbon dioxide gas is produced, causing various baking products to ‘rise’ without the use of active yeast cultures.
This action alters the texture of many foods. Tartaric acid and its salts are used in pancake, cookie, and cake mixes because of these properties
Cream of tartar is used to make cake frosting and candies.
In the winemaking process, tartaric acid is used to alter acidity. Tartaric acid is a natural component of grapes, which are frequently used in the production of wine.
However, some wines are not made with grapes and a tablet of nonsynthetic or synthetic tartaric acid is added to wine to increase the mixture’s acidity.
In addition, organic acids, such as tartaric acid, are known to have antimicrobial properties which make them an important component in wine and other foods.
These antimicrobial properties are associated with the natural acidity of tartaric acid, which creates an unfavorable environment for microorganisms to survive and grow.
The typical concentrations of tartaric acid in wines range 1500 to 4000 mg/L. Higher levels may cause an unpleasant and sour taste (Bastos et al., 2009; Waite and Daeschel, 2007).
Industrial and manufacturing uses of tartaric acid and its derivatives include leather tanning, mirror silvering, ceramics, photography, and blue printing (ferric tartarate serves as a source of blue ink).
Diethyl tartarate and dibutyl tartrate are common esters of tartaric acid and are used in dyeing textiles and the manufacture of lacquer.
Tartaric acid is used in several medical applications including the manufacture of solutions that are used to determine glucose levels.
Rochelle Salt is occasionally used as a laxative. Tartaric acid also acts as a skin coolant and cream of tartar is an effective cleansing agent.
In non-permanent hair dyes, tartaric acid acts as a mild acid
Since 2003, tartaric acid has been included on the National List of Allowed and Prohibited Substances (hereafter referred to as the National List) as a nonagricultural (nonorganic) substance allowed as an ingredient in or on processed products labeled as “organic” or “made with organic (specified ingredients 99 or food group(s)).”
This material is listed both as a nonsynthetic allowed substance if made from grape wine (i.e. L(+) tartaric acid) [7 CFR §205.605 (a)] and a synthetic allowed (7 CFR §205.605 (b)) substance if made from malic acid (i.e. a synthetic form of L(+) tartaric acid).
Following review of data detailing the manufacture of synthetic L(+) tartaric acid, it has been determined that the regulatory language (7 CFR §205.605 (a); 7 CFR §205.605 (b)) referring to synthetic L(+) tartaric acid should be altered to say ‘made from maleic acid’ rather than ‘made from malic acid.’ Data included in the U.S.
Food and Drug Administration (FDA) Generally Recognized as Safe (GRAS) notice for synthetic L(+) tartaric acid (discussed in more detail below) supports this conclusion (FDA, 2009).
The FDA classifies nonsynthetic L(+) tartaric acid and its salts (i.e. L(+) potassium acid tartrate, L(+) sodium potassium tartrate acid) to be GRAS.
The FDA has compiled consumer data and determined that 6 mg each of tartaric acid and potassium acid tartrate added to foods is ingested daily per capita (a total of about 0.2 milligrams (mg) per kilogram (kg) in an adult).
These substances are not believed to be hazardous to the general public if used at used at levels that are now typical, or that might reasonably be expected in the future (FDA, 2011a).
In 2006, the FDA ruled that a synthetic form of L(+) tartaric acid is also considered GRAS.
Synthetic L(+) tartaric acid is produced by the conversion of maleic anhydride to tartaric acid through the enzymatic action of the enzyme cis-epoxisuccinate hydrolase contained in immobilized Rhodococcus ruber cells (FDA, 2009).
The FDA also regulates the use of L(+) tartaric acid as an agent for compensating for the natural acidity of the fruit juice ingredient in fruit jellies, jams, preserves, butters, or related products.
According to 21 CFR 150.141 and 150.161, the quantity of tartaric acid used in these products must a reasonable quantity for adding to the overall acidity of the product.
Additionally, the use of L(+) tartaric acid is permitted as a neutralizing agent in cacoa products, including chocolate liquor and breakfast cocoa (discussed in detail in 21 CFR 163).
The total amount of tartaric acid permitted for use in cocoa products is not to exceed 1.0 part by weight (FDA, 2011b).
Action of the Substance:
Generally, only L(+) tartaric acid is used in food applications. Tartaric acid increases the acidity of a solution and acts as an anti-microbial agent to preserve a food.
The addition of tartaric acid (or products already known to contain tartaric acid) lowers the pH of a solution.
In fruit juices, tartaric acid helps to maintain the proper sugar/acid balance in fruit juices.
By lowering the pH of a solution, the tartaric acid acts as an effective antimicrobial agent by creating an environment too acidic for most microorganisms to grow (Nagy et al., 1993; Waite and Daeschel, 2007).
Baking powder is used in many baking applications and tartaric acid produces carbon dioxide gas following reaction with sodium bicarbonate.
This action causes baking products to ‘rise’ without the use of active yeast cultures.
The use of baking powder containing tartaric acid alters the texture of many foods
As an emulsifier, tartaric acid acts by attaching to a surface and then links two repelling substances, such as oil and water.
This action is useful in the production of dairy products including milk because fats settle on the surface of the milk (i.e. cream) and must be homogeneously mixed to create milk for drinking (Hansenhuettl and Hartel, 2008).
Tartaric acid acts as a chelating agent and is used in the production of canned fruit products (Belitz et al.,2009).
Chelates are formed when an organic acid binds with a metal and prevents its reaction with another chemical.
Chelating agents prevent enzymatic browning through the formation of a complex a free metal and inhibitors through an unshared pair of electrons in their molecular structures
Combinations of the Substance:
At the end of the winemaking process, L(+) tartaric acid is an unwanted component.
In order to precipitate tartaric acid, winemakers add calcium hydroxide and potassium hydroxide to the mixture and then evaporate this solution, producing a white powder that contains calcium or potassium tartrate along with other chemical components.
The powder is sold to manufacturing facilities that purify L(+) tartaric acid
L (+) tartaric acid is used in combination with citric acid to impart tartness to many flavors, including wild cherry and sour apple flavors (Smith and Hong-Shum, 2003).
In food and beverages, L(+) tartaric acid us used a synergist to increase the antioxidant effect of other substances (Hui, 2006a).
Status
Historic Use:
The ancient Greeks and Romans first identified tartaric acid as a by-product of winemaking; however the product was not harnessed for use because wine was not traditionally stored in wooden casks or containers suitable for the sediment that contains the crude tartar.
As the use of wooden casks for the collection of wine increased, so did the collection of crude tartar.
Some winemakers began exclusively using wooden casks for the storage of wine so that crude tartar could be collected more efficiently
173
In the 1400’s, Paracelsus identified the use of tartar as a medicine, but was incorrect in his analysis of the chemical.
The chemical was first isolated in the mid-1700’s after cream of tartar was boiled with chalk and treated with sulfuric acid.
Tartaric acid is used to restore acidity in foods that contain fruit juices and also acts as a neutralizer in cocoa products (FDA, 2011b).
Additional food products made using tartaric acid include bakery products, gelatin, soft drinks, and confectionary products (The Chemical Company, 2010).
The use of tartaric acid (C4H6O6; INS 334) is permitted for organic processing by the Canadian General Standards Board as a non-organic ingredients classified as a food additive in beverages.
Use of the synthetic form is allowed only if the nonsynthetic form of tartaric acid is not commercially available.
Tartaric acid derived from nonsynthetic sources is also permitted for use as a processing aid in beverages (the Canadian General Standards Board, 2011).
The European Economic Community (EEC) permits the use of tartaric acid as a food additive in organic food if derived from a plant source, which is presumably grapes (EEC 889/2008, 2008).
The CODEX Alimentarius Commission describe the functions of tartaric acid as an acidity regulator, adjuvant, anticaking agent, antioxidant, bulking agent, emulsifier, flour treatment agent, humectant, preservative, raising agent, sequestrant, stabilizer, and.
Tartaric acid from a plant source (i.e. nonsynthetic L(+) tartaric acid) is permitted for use as a food additive in organic food production (although exclusions of the GFSA still apply).
Tartaric acid is listed as an acceptable acidity regulator in the Codex General Standard 209 for Food Additives (CODEX STAN 192-1995; CODEX Alimentarius Commission, 2011).
Both nonsynthetic and synthetic forms of L(+) tartaric acid (referred to simply as ‘tartaric acid’) are available for commercial use.
The nonsynthetic form of L(+) tartaric acid is isolated from the undesirable wastes created during the winemaking process.
These unwanted materials include grape pomace, grape stalks, grape seeds, and vine prunings, which naturally contain a significant amount of tartaric acid (Yalcin et al., 2008).
An excess of tartaric acid is generally unwanted in winemaking because it creates a sour and undesirable taste (Bastos et al., 2009).
The available excess tartaric acid is precipitated using potassium hydroxide or calcium hydroxide in order to create a wine with the desired taste.
Then the resulting waste mixture is evaporated.
This process produces a powder containing calcium or potassium tartrate and additional substances including polyphenols and tannins.
The powder is then sold to facilities that purify tartaric acid (Yalcin et al., 2008).
The process for extracting tartaric acid from waste materials is similar to the processing of excess tartaric acid in that potassium hydroxide is added to the waste mixture.
Activated carbon is also added to remove unwanted pigmentation.
The potassium tartrate is precipitated by adding saturated pure tartaric acid solution and then the precipitate is redissolved with acidic water at 70° C.
Potassium and sulfate ions must be removed from the remaining solution so cation exchanges are performed followed by evaporation.
The solution is then crystallized at 4° C (Yalcin et al., 2008).
A synthetic process for producing large quantities of L(+) tartaric acid for commercial use was described by Church and Blumberg (1951).
In this process, maleic acid anhydride is dissolved in water, and a catalyst solution containing tungstic oxide (a metallic catalyst) is added along with hydrogen peroxide.
The solution is held in a reaction vessel that is set to a temperature of 70° C for 12 hours.
The reaction mixture is then cooled, causing the acid to crystallize.
Centrifugation is used to separate out tartaric acid crystals from the mixture.
The tartaric acid is of a sufficient level of purity and does not require an additional purification step (Church and Blumberg, 1951).
In 2006, an alternative method for the manufacture of synthetic L(+) tartaric acid was declared as GRAS by the FDA. Using this method, tartaric acid produced by the conversion of maleic anhydride to tartaric acid.
Technical Evaluation Report Tartaric Acid Handling
This conversion is facilitated by the enzymatic action of cis-expoxisuccinate hydrolase.
This enzyme is contained in immobilized Rhodococcus ruber cells. Rhodococcus ruber cells are produced by fermentation and are subsequently immobilized by the addition of carrageenan, a commonly used food additive that comes from red seaweed.
The reaction substrate is produced in the presence of a metallic catalyst and by the reaction of maleic anhydrate with hydrogen peroxide.
The reaction product is then calcified, separated, and acidified to yield tartaric acid (FDA, 2009; Brenn-O-Kem Ltd., 2011).
This is the process most commonly used in the manufacture of synthetic tartaric acid (Brenn-O-Kem Ltd., 2011).
Both nonsynthetic and synthetic forms of L(+) tartaric acid are manufactured in commercially available quantities.
Synthetic tartaric acid is currently available for commercial use and is manufactured primarily by the conversion of maleic anhydride to tartaric acid using the enzymatic action of cis-eposxisuccinate hydrolase contained in immobilized Rhodococcus ruber cells (FDA, 2009).
Note that the D(-) form of tartaric acid is generally not used for practical applications.
Nonsynthetic tartaric acid is also available for commercial use and is produced following precipitation from sediment and wine wastes obtained during the production of grape wines.
Tartaric acid is a naturally occuring organic acid found in grapes and it is estimated that the average concentration of tartaric acid in winery waste is approximately 50 to 75 kg/ton in grape pomace and approximately 100 to 150 kg/ton in yeast lees (Nerantzis and Tartaridis, 2006).
Tartaric acid is observed at the end of the winemaking in the form of crystals.
These crystals form after potassium and calcium present naturally in wine combine with tartaric acid and form the compounds potassium bitartrate and calcium tartrate, respectively.
During fermentation, these compounds precipitate out and evidence of this action is noted in the formation of crystals.
L(+) tartaric acid is found as a secondary organic acid in many fruits including grapes, cherries, apples, mangos, raspberries, and strawberries. In tamarinds, tartaric acid is a predominant organic acid (Sortwell et al., 1996).
The nonsynthetic form of tartaric acid used for many food and industrial applications is
derived from the wastes associated with winemaking. Grape growers and wine makers produce a significant amount of waste materials and tartaric acid is contained in grape pomace and yeast lees.
Tartaric acid can be precipitated out of wastes and the actual wine solution by adding potassium hydroxide or calcium hydroxide.
After evaporation, tartaric acid in the form of crystals remains and can be sent for purification (Nerantzis and Tataridis, 2006).
Nonsynthetic L(+) tartaric acid and its salts (i.e. L(+) potassium acid tartrate, L(+) sodium potassium
308 tartrate acid) are classified by the FDA to be GRAS. These substances are not believed to be hazardous to
309 the general public if used at used at levels that are now current (a total of about 0.2mg per kg in an adult),
310 or that might reasonably be expected in the future (FDA, 2011a).
One of the many functions of L(+) tartaric acid is the ability to act as a preservative.
The other primary functions of L(+) tartaric acid are discussed in more detail in the sections on Specific Uses and the Action of the Substance.
Tartaric acid acts as an effective preservative by controlling the pH of a variety of food products by altering the acidity and preventing the growth of spoilage microbes.
The first dissociation constant or pK1 of tartaric acid is equal to 2.98 and the second dissociation constant or pK2 is equal to 4.34.
Typically an acidic environment causes a loss in enzymatic function in spoilage microbes, thereby destroying them (Waite and Daeschel, 2007).
Tartaric acid is used to alter the acidity of milk, margarine, meat and poultry products,fruit preserves, jellies, and jams, canned fruits, sherbets, beverages (including fruit juices), and soft drinks.
A small amount of tartaric acid is added to a solution (1-3% of the total solution) that meat carcasses are dipped in for the reduction of microbial populations present on the carcass (Smith and Hong-Shum, 2003).
In wine and juices, tartaric acid acts as a preservative by reducing the pH. Tartaric acid is typically added prior to fermentation of grapes or after fermentation to correct the solution’s overall acidity level (Smith and Hong-Shum, 2003; Waite and Daeschel, 2007).
L(+) tartaric acid is used to improve flavors, colors, and textures lost in food processing (Smith and Hong344 Shum, 2009).
As an acidulant, tartaric acid is used to improve the taste and enhance flavors of fruit-flavored products and can add intensity to the sweetness of sucrose (Heath, 1981).
A wide variety of products may contain tartaric acid, including fruit-flavored carbonated and noncarbonated beverages, dry beverage powders, low-calorie beverages, candies, fruit gums, and thermal processed fruits. Specifically, tartaric acid enhances lime, cranberry, and grape flavors (Hui, 2006a).
Tartaric acid is also considered a chelating agent and prevents discoloration that might occur during food processing.
Chelating agents are capable of binding metal ions and in doing so improve color, aroma, and texture.
Tartaric acid is added to canned fruit products because it increases the stability of the product’s color and aroma (Belitz et al., 2009).
Technical Evaluation Report Tartaric Acid Handling
The texture of food is altered by the presence of tartaric acid or one of its salts, cream of tartar.
Tartaric acid and cream of tartar are examples of fast-acting baking powders.
Fast-acting baking powders contain acids that release a large amount of gas in a short amount of time during the mixing process or while a batter or other baking mixture is at rest.
Tartaric acid and cream of tartar are important components of cookie, pancake, and cake mixes and are often sold as ‘double-acting baking powder’ (Hui, 2006b)
If appropriate use patterns and disposal recommendations are followed, it is unlikely that tartaric acid would cause harm to the environment.
However, tartaric acid is an acidulant and its release to the environment in large quantities could alter the pH of aquatic and soil environments.
If a large amount of an organic acid (i.e., tartaric acid) was released to the soil after improper disposal of excess tartaric acid or following improper use patterns, the increased acidity could create an environment incapable of supporting native soil organisms (Bickelhaupt, 2011).
L(+) tartaric acid in both the nonsynthetic and synthetic forms and its salts (i.e., L(+) potassium acid tartrate, L(+) sodium potassium tartrate acid) have been classified by the FDA as GRAS (FDA, 2009, 2011a).
While there are no known specific hazards to human health associated with normal use patterns of tartaric acid, acute effects associated with exposure are reported in Material Safety Data Sheets (MSDS) for L(+) tartaric acid.
Brief contact with tartaric acid is noted to cause possible irritation to the eyes.
However, scientific literature supporting these effects was not identified.
One study reported no signs of irritation after humans were administered a dermal dose of hand lotion containing tamarind and 2 percent (w/w) tartaric acid for 30 minutes daily for 5 days under semi-occlusive patch (Maenthaisong et al., 2007).
An MSDS (Industria Chimica Valenzana, 2007) notes that prolonged contact with L(+) tartaric acid may cause irritation to the skin, upper respiratory tract, and mucous membranes. Ingestion of large quantities may cause irritation to the gastro-intestinal tract and could result in nausea or vomiting. Chronic toxicity is determined as low.
Pow refers to the octanol water coefficient of a substance.
Technical Evaluation Report Tartaric Acid Handling
The oral LD50 of tartaric acid is between 3310 and 3530 mg/kg body weight in the rat and is 5000 mg/kg body weight in the dog.
The acceptable daily intake of tartaric acid and its potassium and sodium salt is up to 30 mg/kg body weight for humans (Smith and Hong-Shum, 2008).
The daily intake of tartaric acid that is added to foods is orders of magnitude below that which could be expected to cause human toxicity (FDA, 2011a).
Tartaric acid has a variety of applications in food handling, including use in baking applications and as an acidulant, flavoring agent, preservative, pH adjuster, and chelating agent.
No organic agricultural products have been identified as appropriate alternatives for tartaric acid in food applications (including winemaking).
However, other organic acids, including citric acid and malic acid, have demonstrated similar properties as tartaric acid with respect to its function as an acidulants, flavoring and chelating agent, pH adjuster, and preservative. Both citric and malic acids are included on the National
List as non-organic, non-agricultural substances permitted for use in organic agriculture (7 CFR §205.605).
In baking, L(+) tartaric acid is a critical component of baking powder.
Baking powder can be replaced with baking soda, but cream of tartar must be added to maintain the properties of baking powder.
Therefore, no sound alternative is available for tartaric acid in many baking applications (Hui, 2006b).
When used as an acidulant and flavoring agent, citric acid can sometimes act as a replacement of tartaric acid (Smith and Hong-Shum, 2008).
The National List includes nonsynthetic citric acid as permitted for use in organic food processing and handling.
Tartaric acid is a critical component in winemaking and cannot be replaced with an organic alternative.
438 Although both malic acid and tartaric acid are natural components of grapes and are used to alter the acidity in wine and possess characteristics of a preservative, they generally cannot be used interchangeably because the substances contribute differently to the wine’s overall taste.
In addition, the concentration of malic acid in grapes is much smaller than tartaric acid.
It is because of this phenomenon that additional malic and/or tartaric acid is added by winemakers in order to produce the desired taste and to obtain the proper pH for the wine solution. L-Malic acid (CAS # 97–67–6) is included on the National List as a nonorganic substance allowed as an ingredient in or on processed products labeled as “organic” or “made with organic (specified ingredients or food group(s))” (Volschenk et al., 2006).
When simply seeking to adjust pH, many organic acids can be used in place of tartaric acid.
Citric acid and malic acid are useful replacements for tartaric acid; however it is important to note that these acids also have flavors associated with their presence in a substance.
If seeking a purely grape flavor, then tartaric acid is the primary organic acid that should be used because malic acid adds and apple flavor to a product and citric acid adds many citrus flavors.
These alternative flavors may not be desirable to the product’s flavor profile (Hui, 2006a).
DL-Tartaric acid
tartaric acid
2,3-Dihydroxysuccinic acid
2,3-Dihydroxybutanedioic acid
133-37-9
526-83-0
Racemic acid
Uvic acid
Traubensaure
Racemic tartaric acid
DL-Tartrate
Paratartaric acid
Paratartaric aicd
Threaric acid
Resolvable tartaric acid
BUTANEDIOIC ACID, 2,3-DIHYDROXY-
(+)-Tartaric acid
Natural tartaric acid
Acidum tartaricum
NSC62778
Tartaric acid D,L
tartrate
Tartaric acid, L-(+)-
Baros
CHEBI:15674
dl-2,3-dihydroxybutanedioic acid
Dextrotartaric acid
(2RS,3RS)-Tartaric acid
MFCD00071626
NSC 148314
Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-
E-7050 (2S,3S)-2,3-dihydroxysuccinic acid
(2R,3R)-rel-2,3-Dihydroxysuccinic acid
DL-Tartaric acid, 99.5%
Butanedioic acid, 2,3-dihydroxy-(R*,R*)-(.+/-.)-
Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-
868-14-4
Tartaric acid, L-
(2R,3R)-2,3-Dihydroxybernsteinsaeure
Tartaric acid (VAN)
1007601-97-9
Kyselina vinna [Czech]
NSC155080
Butanedioic acid, 2,3-dihydroxy- (2R,3R)-
Tartaric acid [USAN:JAN]
(.+-.)-Tartaric acid
C4H6O6
(+)-(2R,3R)-Tartaric acid
d-alpha,beta-Dihydroxysuccinic acid
NSC-62778
Kyselina 2,3-dihydroxybutandiova [Czech]
(+) tartaric acid
(-) tartaric acid
1,2-Dihydroxyethane-1,2-dicarboxylic acid
AI3-06298
1,2-dicarboxylic acid
WLN: QVYQYQVQ
(-) D-Tartaric acid
ACMC-209qpg
Sal tartar (Salt/Mix)
Tartaric acid, (DL)-
Butanedioic acid, 2,3-dihydroxy- (R-(R*,R*))-
Butanedioic acid, 2,3-dihydroxy-, [S-(R*,R*)]-
Malic acid, 3-hydroxy-
laevo-(+)-tartaric acid
dextro,laevo-tartaric acid
Succinic acid,3-dihydroxy
SCHEMBL848
ACMC-209cz3
bmse000167
Succinic acid,3-dihydroxy-
(.+/-.)-Tartaric acid
DSSTox_CID_26986
DSSTox_RID_82036
2,3-dihydroxy-succinic acid
DSSTox_GSID_46986
Oprea1_827092
TARTARIC ACID, (L)
Tartaric acid, (.+-.)-
Butanedioic acid,3-dihydroxy-
CHEMBL333714
Dihydroxysuccinic acid, (DL)-
Tartaric acid, (.+/-.)-
DTXSID5046986
L+Tartaric Acid FCC, NF, USP
2,3-bis(oxidanyl)butanedioic acid
HMS3370M15
(+)-2,3-dihydroxybutanedioic acid
(S,S)-Tartaric acid;Tartaric acid
BCP14303
Process for producing DL-tartaric acid
Abstract
DL-Tartaric acid is produced by hydrolysis of epoxysuccinic acid by the process, comprising contacting an aqueous epoxysuccinic acid solution with a catalyst containing activated charcoal, aluminum oxide or ferric oxide which is substantially insoluble in said solution.
Conversion of epoxysuccinic acid as well as selectivity to dl-tartaric acid are very high.
Classifications
C07C51/367 Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
Process for producing DL-tartaric acid
Abstract
DL-Tartaric acid is produced by hydrolysis of epoxysuccinic acid by the process, comprising contacting an aqueous epoxysuccinic acid solution with a catalyst containing activated charcoal, aluminum oxide or ferric oxide which is substantially insoluble in said solution.
Conversion of epoxysuccinic acid as well as selectivity to dl-tartaric acid are very high.
ABSTRACT
dl-Tartaric acid is produced by hydrolysis of epoxysuccinic acid by the process, comprising contacting an aqueous epoxysuccinic acid solution with a catalyst containing activated charcoal, aluminum oxide or ferric oxide which is substantially insoluble in said solution.
Conversion of epoxysuccinic acid as well as selectivity to dl-tartaric acid are very high.
10 Claims, No Drawings
PROCESS FOR PRODUCING DL-TARTARIC ACID This invention relates to a process for producing dltartaric acid.
More particularly, this invention relates to an improvementof the process for producing dltartaric acid by hydrolysis of epoxysuccinic acid.
dl-Tartaric acid has been used as food additives such as sour seasonings.
It can also widely be used as industrial chemicals such as starting materials for detergents.
It has heretofore been know to produce dl-tartaric acid by allowing hydrogen peroxide to react with maleic acid in the presence of a tungsten compound catalyst (see, for example, J. M. Charch and R. Blumbery: Industrial and Engineering Chemistry vol. 43, p.1780 (1951)).
According to this method, it is known that epoxysuccinic acid is formed as intermediate which is then hydrolyzed to produce dl-tartaric acid.
However, epoxysuccinic acid, as different from other epoxy compounds, contains an oxirane ring in the molecule which is very stable.
Therefore, preparation of dl-tartaric acid by hydrolysis of this compound is not easy.
In the absence of a catalyst, even after boiling of an aqueous solution of epoxysuccinic acid which is continued as long as, for example, 5 hours, only 73.8% of said compound is hydrolyzed.
As catalysts for hydrolysis of oxirane rings, acids or bases have heretofore been generally known.
However, to the best of our knowledge, when sulfuric acid, for example, is used as a catalyst for preparation of dl-tartaric acid by hydrolysis of epoxysuccinic acid, there are drawbacks such that a great amount of sulfuric acid has to be used, that it takes a long time to carry out the reaction and that the yield of dl-tartaric acid is low. On the other hand, when bases such as caustic alkalis are used as catalysts, the products are in the form of alkali salts of dl-tartaric acid and disadvantageous in the production of free dl-tartaric acid. Furthermore, when the rate of reaction is increased by using sulfuric acid in the production of dl-tartaric acid, the selectivity is lowered. On the other hand, the rate of reaction must be decreased in order that the selectivity should not be lowered.
The object of the present invention is to provide an industrially advantageous process for producing dltartaric acid from epoxysuccinic acid in a very short time with good conversion as well as selectivity.
It has now been found that activated charcoal, aluminum oxide or ferric oxide effectively catalyzes the hy drolysis of epoxysuccinic acid.
Namely, the present invention provides a process for producing dl-tartaric acid from epoxysuccinic acid, comprising contacting an aqueous epoxysuccinic acid solution with a catalyst containing activated charcoal, aluminum oxide or ferric oxide which is substantially insoluble with said solution.
The catalyst containing activated charcoal, aluminum oxide or ferric oxide to be used in the present invention is a substance which is normally in the solid state and is insoluble in an aqueous epoxysuccinic acid solution.
As the catalyst containing activated charcoal, aluminum oxide or ferric oxide, the substance per se, alone or in mixtures, of these activated charcoal, aluminum oxide or ferric oxide may be used. Alternatively, other compounds containing these substances may also be used.
For example, silica-alumina which contains aluminum oxide .or oxide complexes which contain ferric oxide and other metal oxides such as titanium oxide,
eg titanium oxide ferric oxide (represented by 2Fe- O .3TiO or Fe O .3TiO may be mentioned.
These substances catalyze the hydrolysis of epoxysuccinic acid in heterogeneous catalytic systems.
Among these catalysts, the catalyst containing aluminum oxide or ferric oxide is preferred from the standpoint of activity per unit weight.
Above all, the catalyst containing ferric oxide is most preferred.
Although the catalyst containing activated charcoal is the lowest in catalytic activity among the three, it has an advantage that colorless dl-tartaric acid can be produced by the effect of decoloration of activated charcoal even if the starting epoxysuccinic acid may contain colored impurities.
The amount of the catalyst used may vary depending on the catalyst employed, the temperature at the time of hydrolysis, and the concentration of the aqueous epoxysuccinic acid solution.
Usually, when a catalyst containing activated charcoal is used, the amount of activated charcoal is preferably from 10 to 40% by weight, most preferably from 15 to 30% by weight, based on epoxysuccinic acid. On the other hand, when a catalyst containing aluminum oxide or ferric oxide is used, the amount of aluminum oxide or ferric oxide is preferably from 0.5 to 10% by weight, most preferably from 1 to 5% by weight based on epoxysuccinic acid.
These catalysts are insoluble solids and therefore they can easily be separated from the reaction mixture by filtration, after the hydrolysis reaction is over.
Repeated use of these catalysts is also possible.
The process according to the present invention is also suitable for practicing a continuous reaction by the use of a fixed-bed reactor.
The starting epoxysuccinic acid may either be cisepoxysuccinic acid or trans-epoxysuccinic acid, but cisepoxysuccinic acid is preferred because no mesotartaric acid is by-produced.
The epoxysuccinic acid used as the starting material may be produced in any way.
For example, it may be produced by allowing hydrogen peroxide to react with maleic acid in an aqueous solution in the presence of a tungsten compound catalyst.
Alternatively, it may be produced according to the method, comprising allowing hydrogen peroxide to react with acid calcium maleate in an aqueous solution in the presence of a tungsten compound catalyst to prepare acid calcium epoxysuccinate and then subjecting this acid calcium epoxysuccinate to acid decomposition. Furthermore, epoxysuccinic acid from the decomposed liquid obtained by acid decomposition of an epoxysuccinic acid salt or ester may also be used.
The decomposed liquid itself may also be available.
The concentration of an aqueous epoxysuccinic acid solution is not particularly limited, so long as it is a homogenous aqueous solution at the reaction temperature.
Industrially, however, it is preferred to use a solution containing 10 to 50% by weight of epoxysuccinic acid.
The reaction temperature may be the reflux temperature at the normal pressure of an aqueous epoxysuccinic acid solution or lower.
Preferably, however, the reaction temperature is 110C or less, most preferably from to C.
The thus obtained reaction mixture is subjected to filtration, while it is still hot, to remove the catalyst.
The filtrate is directly or after concentration, if necessary, cooled to crystallize dl-tartaric acid which is then separated, or the filtrate is evaporated to dryness, to obtain crystals of dl-tartaric acid. According to the process of the present invention, dl-tartaric acid can be obtained in a very short time, namely in 2 hours or less, preferably from 1 to 2 hours, whereby conversion of epoxysuccinic acid reaches 95% or more and the selectivity of dl-tartaric acid from epoxysuccinic acid is very high to result in increase in the yield of dl-tartaric acid.
The process of the present invention is further advantageous in that separation and recovery of catalyst are very easy.
The filtrate, which is obtained after dltartaric acid is crystallized and the crystals are separated from the reaction mixture after removal of the catalyst, contains dl-tartaric acid remaining in a solution and traces of unaltered epoxysuccinic acid.
This filtrate and the catalyst removed therefrom is readily available for recycle for re-use.
The present invention is also industrially advantageous in this respect.
The process of the present invention is further illustrated in detail with reference to the following examples.
In the examples as set forth below, for the purpose of showing the result briefly, the product crystals are obtained by the method wherein the reaction mixture after removal of the catalyst is evaporated to dryness.
Accordingly, the product crystals in the examples contain traces of unaltered epoxysuccinic acid, which can be removed substantially completely by recrystallization of the above crude product crystals from an aqueous solution thereof. Accordingly, crystals of ditartaric acid with a purity of 99.5% or more are obtained by the crystallization method.
EXAMPLE 1
To an aqueous solution having 6.6 g of epoxysuccinic acid dissolved in 50 g of water is added 1 g of commericially available activated charcoal powders and the mixture is heated at 100C for 2 hours under gentle stirring.
As the result, the conversion of epoxysuccinic acid is 96.3%.
The reaction mixture is filtered, while it is still hot, to separate it into activated charcoal and the filtrate.
The catalyst is washed with hot water and the washed water is added to the filtrate. The filtrate containing this washed water is evaporated to dryness and the obtained crystals are dried to constant weight to obtain 7.46 g of dl-tartaric acid crystals with a purity of 96.9%. This corresponds to a 96.3% yield of dl-tartaric acid based on the starting epoxysuccinic acid. In this crystal is contained 0.23 g of unaltered epoxysuccinic acid.
EXAMPLE 2
Example 1 is repeated except that 0.153 g of aluminum oxide (oz-A1 is used in place of activated charcoal and the reaction is conducted for 1 hour.
Conversion of epoxysuccinic acid is 95.2% and 7.42 g of dl-tartaric acid crystals with a purity of 96.1% is obtained.
This corresponds to a 95.0% yield of dltartaric acid based on the starting epoxysuccinic acid.
In this crystal is contained 0.29 g of unaltered epoxysuccinic acid.
EXAMPLE 3 Example 1 is repeated except that 0.240 g of ferric oxide (a-Fe O is used in place of activated charcoal and the reaction is conducted for 1 hour.
Conversion of epoxysuccinic acid is 95.8% and 7.41 g of dl-tartaric acid crystals with a purity of 96.8% is obtained.
This corresponds to a 95.6% yield of dltartaric acid based on the starting epoxysuccinic acid.
In the crystals is contained 0.23 g of unaltered epoxysuccinic acid.
COMPARATIVE EXAMPLE 1 An aqueous solution having 6.6 g of epoxysuccinic acid dissolved in g of water is refluxed for 1 hour under heating, whereby the conversion of epoxysuccinic acid is 22.0% and the yield of dl-tartaric acid based on the starting epoxysuccinic acid is 21.6%.
When the solution is further refluxed under heating for an additional 4 hours, the conversion of epoxysuccinic acid is only 73.8%.
In this reaction mixture is contained dl-tartaric acid in a yield of 72.5% based on the starting epoxysuccinic acid.
COMPARATIVE EXAMPLE 2 An aqueous solution having 6.6 g of epoxysuccinic acid and 2.6 g of 95.4% sulfuric acid dissolved in 50 g of water is refluxed for 1 hour under heating.
Conversion of epoxysuccinic acid is 34.1%.
In the reaction mixture is contained dl-tartaric acid corresponding to a 31.6% yield based on the starting epoxysuccinic acid.
When the solution is further refluxed under heating for an additional 4 hours, the conversion of epoxysuccinic acid is only 87.5% and in the reaction mixture is contained dl-tartaric acid corresponding to a 81.0% yield based on the starting epoxysuccinic acid.
EXAMPLE 4 Example 1 is repeated except that 0.508 g of silicaalumina (13% by weight of A1 0 content) is used in place of activated charcoal and the reaction is conducted for 1 hour.
Conversion of epoxysuccinic acid is 97.0% and 7.50 g of dl-tartaric acid crystals with a purity of 95.5% is obtained.
This corresponds to a 95.5% yield of dltartaric acid based on the starting epoxysuccinic acid.
In the reaction mixture is contained 0.22 g of unaltered epoxysuccinic acid.
EXAMPLE 5 Example 1 is repeated except that 0.495 g of titanium oxide ferric oxide (Fe O .3TiO is used in place of activated charcoal and the reaction is conducted for 1 hour.
Conversion of epoxysuccinic acid is 95.5% and 7.43 g of dl-tartaric acid crystals with a purity of 96.0% is obtained.
This corresponds to a 95.1% yield of dltartaric acid based on the starting epoxysuccinic acid.
In the reaction mixture is contained 0.20 g of unaltered epoxysuccinic acid.
What we claim is:
1. A process for producing dl-tartaric acid by hydrolysis of epoxysuccinic acid, comprising contacting an aqueous epoxysuccinic acid solution with a catalyst consisting essentially of activated charcoal, aluminum oxide or ferric oxide, and mixtures thereof said catalyst being substantially insoluble in said aqueous epoxysuccinic acid solution.
2. A process according to claim 1 wherein the catalyst consists essentially of activated charcoal in an amount from l0 to 40% by weight based on epoxysuccinic acid.
3. A process according to claim 1 wherein the catalyst consists essentially aluminum oxide or ferric oxide in an amount from 0.5 to by weight based on epoxysuccinic acid.
4. A process according to claim 1 wherein the catalyst is activated charcoal per se.
5. A process according to claim 1 wherein the catalyst is aluminum oxide per se.
6. A process according to claim 1 wherein the catalyst is ferric oxide per se.
7. A process according to claim 1 wherein the cata- UNITED STATES PATENT AND TRADEMARK OFFICE CERTIFICATE OF CORRECTION PATENT NO. 3,923, 884