133-37-9

Basic information

• Product Name: DL-Tartaric acid
• Synonyms: (2S,3S)-2,3-dihydroxybutane-1.4-dioicacid;2,3-dihydroxy-,(R*,R*)-(±)-Butanedioicacid;2,3-dihydroxy-,(theta,theta)-(+/-)-butanedioicaci;Butanedioic acid, 2,3-dihydroxy-(R*,R*)-(.+/-.)-;Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-(±DL-2,3-Dihydroxysuccinicacid;dl-Tartaric acid anhydrous;DL-Weinsαure
• CAS NO: 133-37-9
• Molecular Formula: C₄H₆O₆
• Molecular Weight: 150.09
• EINECS: 205-105-7
• Product Categories: Food & Feed ADDITIVES;Food additive and acidulant
• Mol File: 133-37-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 210-212 °C(lit.)
• Boiling Point: 191.59°C (rough estimate)
• Flash Point: 210 °C
• Appearance: White/Liquid
• Density: 1.788
• Vapor Pressure: 4.93E-08mmHg at 25°C
• Refractive Index: 1.5860 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: H2O: 0.1 g/mL, clear
• PKA: 3.03, 4.37(at 25℃)
• Water Solubility: soluble
• Stability: Stable. Incompatible with bases, oxidizing agents, reducing agents, silver.
• Merck: 14,9069
• BRN: 1725148
• CAS DataBase Reference: DL-Tartaric acid(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Tartaric acid(133-37-9)
• EPA Substance Registry System: DL-Tartaric acid(133-37-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-41
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 133-37-9(Hazardous Substances Data)

Usage

Description

DL-Tartaric acid, also known as dihydroxy succinic acid, is a colorless crystalline solid with an acid taste and a melting temperature of 170°C (338°F). It is odorless and occurs in two forms, Land D-tartaric acid, which are mirror images of each other. DL-Tartaric acid is found in many fruits or other parts of plants, free or combined with potassium, calcium, or magnesium. It is also present in raw, lean fish, white wine, red wine, and port wine.

Uses

Used in Food Industry:
DL-Tartaric acid is used as a synergist for antioxidants, emulsifier, sequestrant, and flavoring agent. It is mixed with sodium bicarbonate and used as a leavening agent in food preparation.
Used in Pharmaceutical Industry:
DL-Tartaric acid is utilized in the preparation of tartar emetic, which is used in cough syrup as an expectorant. It is also used in the production of effervescent salts, in combination with citric acid, to improve the taste of oral medications.
Used in Chemical Industry:
DL-Tartaric acid is used as a chemical intermediate and a sequestrant. It is also used in tanning, effervescent beverages, baking powder, ceramics, photography, textile processing, mirror silvering, and metal coloring.
Used in Metal and Farming Industries:
DL-Tartaric acid acts as a chelating agent in metal and farming industries.
Used in Ink, Toner, and Colorant Products:
DL-Tartaric acid is utilized in pigments, processing aids, ink, toner, and colorant products.
Used as Lubricant and Grease:
DL-Tartaric acid is used as a lubricant and grease.
Used in Synthesis:
DL-Tartaric acid can be used in the Debus–Radziszewski reaction as a weak acid for the synthesis of imidazolium ionic liquid. It is also used as an additive in electrochemical deposition technique for the synthesis of bismuth thin films to be used as X-ray absorbers. Furthermore, it serves as a complexing agent for the synthesis of nano-crystalline indium tin oxide (ITO) powder and as a dopant for the synthesis of polyaniline nanofibers and nanotubes by oxidation polymerization.

FUNCTIONAL USES

Synergist for antioxidants, acid, emulsifier, sequestrant, flavouring agent

Solubility

Freely soluble in water; sparingly soluble in ethanol

Melting range

200 - 206o with decomposition when heated rapidly in a sealed capillarytube

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.

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.

InChI:InChI=1/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1

Synthetic route

Glyoxilic acid (298-12-4) → DL-tartaric acid (133-37-9)

Conditions	Yield
With bis(cyclopentadienyl)-titanium(III) chloride In tetrahydrofuran at -78 - 20℃;	68%
With acetic acid; zinc
elektrolytische Reduktion;
With alkali elektrolytische Reduktion;
Electrolysis;

sorbic Acid (110-44-1) → DL-tartaric acid (133-37-9)

Conditions	Yield
With potassium permanganate at 0℃;

hydrogen cyanide (74-90-8) + Glyoxal (131543-46-9) → DL-tartaric acid (133-37-9)

Conditions	Yield
With hydrogenchloride

mannitol (69-65-8) → DL-tartaric acid (133-37-9)

Conditions	Yield
With nitric acid

D-galactitol (608-66-2) → DL-tartaric acid (133-37-9)

Conditions	Yield
With nitric acid

dihydroxyfumaric acid (133-38-0) + quinhydrone (106-34-3) → DL-tartaric acid (133-37-9)

dihydroxyfumaric acid (133-38-0) → DL-tartaric acid (133-37-9)

Conditions	Yield
With hydroquinone

D-tartaric acid (147-71-7) + L-Tartaric acid (87-69-4) → DL-tartaric acid (133-37-9)

Conditions	Yield
unter Waermeentwicklung;
With water

meso-tartaric acid (147-73-9) → DL-tartaric acid (133-37-9)

Conditions	Yield
at 200℃;

L-Tartaric acid (87-69-4) + furan-2,3,5(4H)-trione pyridine (1:1) → DL-tartaric acid (133-37-9) + tartaric acid (87-69-4)

L-Tartaric acid (87-69-4) → meso-tartaric acid (147-73-9) + DL-tartaric acid (133-37-9)

Conditions	Yield
With water
With hydrogenchloride
With hydrogenchloride im geschlossenen Rohr;
With sodium hydroxide; water

L-Tartaric acid (87-69-4) → DL-tartaric acid (133-37-9)

Conditions	Yield
With sodium hydroxide
With potassium hydroxide
With sodium hydroxide Racemisierung;

D-glucaric acid (87-73-0) → L-Tartaric acid (87-69-4) + DL-tartaric acid (133-37-9)

Conditions	Yield
With nitric acid

D-glucaric acid (87-73-0) → DL-tartaric acid (133-37-9)

Conditions	Yield
With nitric acid

meso-galactaric acid (526-99-8, 1213827-87-2) → DL-tartaric acid (133-37-9)

Conditions	Yield
With nitric acid
With potassium permanganate
With permanganate(VII) ion

1,3-butadiene-1-carboxylic acid (626-99-3) → DL-tartaric acid (133-37-9)

Conditions	Yield
With potassium permanganate at 0℃;

dihydroxytartaric acid (76-30-2) → meso-tartaric acid (147-73-9) + DL-tartaric acid (133-37-9)

Conditions	Yield
With zinc

1,2-dihydroxy-ethane-1,1,2-tricarboxylic acid (639-51-0) → DL-tartaric acid (133-37-9)

Conditions	Yield
With water

inositol (551-72-4, 643-12-9, 6917-35-7, 39907-99-8, 40461-73-2, 41546-32-1, 41546-33-2, 41546-34-3, 41546-35-4, 41546-36-5) → DL-tartaric acid (133-37-9)

Conditions	Yield
With alkaline permanganate

2-Methyl-1,4-benzoquinone (553-97-9) → DL-tartaric acid (133-37-9)

Conditions	Yield
With sulfuric acid bei der elektrolytischen Oxydation an einer PbO2-Anode;

benzene-1,2-diol (120-80-9) → DL-tartaric acid (133-37-9) + cis-2,3-epoxysuccinic acid (16533-72-5)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide at 70 - 80℃;

tartaric acid (87-69-4) → meso-tartaric acid (147-73-9) + DL-tartaric acid (133-37-9)

Conditions	Yield
With hydrogenchloride
With water
With alkaline solution

tartaric acid (87-69-4) → DL-tartaric acid (133-37-9)

Conditions	Yield
With aluminium salt
With water at 175℃;

maleic acid (110-16-7) → DL-tartaric acid (133-37-9)

Conditions	Yield
With sulfuric acid; lead dioxide bei der elektrolytischen Oxydation;
With dihydrogen peroxide; tungsten(VI) oxide
With dihydrogen peroxide; tungsten(VI) oxide

(2E)-but-2-enedioic acid (110-17-8) → DL-tartaric acid (133-37-9)

Conditions	Yield
With sodium chlorate; osmium(VIII) oxide; water
With sodium chlorate; osmium(VIII) oxide; water at 50℃;
With osmium(VIII) oxide; potassium chlorate; water at 50℃;

(2E)-but-2-enedioic acid (110-17-8) → DL-tartaric acid (133-37-9) + oxalic acid (144-62-7)

Conditions	Yield
With osmium(VIII) oxide; dihydrogen peroxide; tert-butyl alcohol at 0℃;
With osmium(VIII) oxide; dihydrogen peroxide; tert-butyl alcohol at 0℃;

hydroquinone (123-31-9) → DL-tartaric acid (133-37-9) + cis-2,3-epoxysuccinic acid (16533-72-5)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide
With sodium hydroxide; dihydrogen peroxide at 70 - 80℃;

oxalic acid diethyl ester (95-92-1) → DL-tartaric acid (133-37-9)

Conditions	Yield
With sodium amalgam; ethanol Produkt: Traubensaeureester;

glycerol (56-81-5) → DL-tartaric acid (133-37-9)

Conditions	Yield
With hydrazine at 190 - 250℃;

p-benzoquinone (106-51-4) → DL-tartaric acid (133-37-9)

Conditions	Yield
With sulfuric acid elektrolytische Oxydation;

vanadocene + DL-tartaric acid (133-37-9) → C5H5(1-)*V(3+)*C4H4O6(2-)=(C5H5)V(C4H4O6)

Conditions	Yield
In diethyl ether byproducts: H2, cyclopentadiene; Ar atmosphere; 20 h, 95°C; ppt. was filtered off, washed with ether, and dried; elem. anal.;	93%

Pt(2,2':6',2''-terpyridine)Cl + DL-tartaric acid (133-37-9) → [PtCl(2,2′:6′,2′′-terpyridine)](DL-Hta)

Conditions	Yield
Stage #1: DL-tartaric acid With lithium hydroxide monohydrate In water for 0.166667h; Darkness; Stage #2: Pt(2,2':6',2''-terpyridine)Cl for 0.166667h;	92%

ethyl 3-amino-5-fluoro-4,4-dimethoxypentanoate (908253-60-1) + DL-tartaric acid (133-37-9) → 1-ethoxy-5-fluoro-4,4-dimethoxy-1-oxopentan-3-aminium tartarate

Conditions	Yield
In water; isopropyl alcohol at 20℃; for 4h;	87.1%

ethanol (64-17-5) + DL-tartaric acid (133-37-9) → (+/-)-diethyl tartrate (57968-71-5)

Conditions	Yield
With Dowex 50W-X8 (H+) In benzene Heating;	82%
With hydrogenchloride
With hydrogenchloride

indium(III) hydroxide + DL-tartaric acid (133-37-9) + water (7732-18-5) → α-[InOH(D/L-tartrate)]*2H2O InOH(COOCHOHCHOHCOO)*2H2O, α, low temperature

Conditions	Yield
In water High Pressure; reaction of In(OH)3, organic ligand and H2O at 110°C for 2 days; elem. anal.;	75%

DL-tartaric acid (133-37-9) + cyclohexanol (108-93-0) → dicyclohexyl tartrate (15785-59-8, 83071-79-8, 133098-69-8, 133098-70-1, 140850-35-7)

Conditions	Yield
With acidic ion exchange resin In chloroform for 40h; Heating;	73%

DL-tartaric acid (133-37-9) → strontium d,l-tartrate (868-19-9, 22438-83-1)

Conditions	Yield
With strontium(II) acetate In water at 100℃; for 48h; Autoclave;	73%

DL-tartaric acid (133-37-9) → C4H4O6(2-)*Ca(2+)

Conditions	Yield
With calcium acetate In water at 60℃; for 48h;	72%

DL-tartaric acid (133-37-9) + benzyl alcohol (100-51-6) → dibenzyl DL-tartrate

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 12h; Dean-Stark; Reflux;	72%

DL-tartaric acid (133-37-9) + 1,2-diamino-benzene (95-54-5) → 1,2-bis(2-benzimidazyl)-1,2-ethanediol

Conditions	Yield
With hydrogenchloride for 24h; Heating;	70%

hexaammonium heptamolybdate tetrahydrate + ammonium hydroxide + DL-tartaric acid (133-37-9) + dihydrogen peroxide (7722-84-1) → (NH4)2[MoO(O2)2(tartrate(2-))]*2H2O

Conditions	Yield
In water soln. of ammonium heptamolybdate tetrahydrate and D,L-tartaric acid in water treated with soln. of H2O2 (35 wt.-%) and aq. ammonia, stirred for 2 h; EtOH added, soln. stored at room temp. for 24 h, ppt. filtered off, washed with EtOH and air-dried; elem. anal.;	69%

DL-tartaric acid (133-37-9) + tert-butyl 4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylate (144702-26-1) → telmisartan tert-butyl ester DL-tartarate

Conditions	Yield
In methanol for 5h; Reflux;	68.64%

DL-tartaric acid (133-37-9) + tetra(n-butyl)ammonium hydroxide (2052-49-5) → 2C16H36N(1+)*C8H4As2O12(2-)

Conditions	Yield
With arsenic(III) trioxide In water at 20℃; for 48h;	68%

4-amino-2-nitrophenol (119-34-6) + DL-tartaric acid (133-37-9) → 2,3-dihydroxy-N-(4-hydroxy-3-nitrophenyl)succinamic acid

Conditions	Yield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	55%

DL-tartaric acid (133-37-9) + urea (57-13-6) → 2-oxo-4-imidazoline-4-carboxylic acid (39828-47-2)

Conditions	Yield
With sulfuric acid at 80℃; for 1h;	53%

2-vinylpyridine (100-69-6) + DL-tartaric acid (133-37-9) + piperazine dihydrochloride hydrate (6091-62-9) → 1-<2-(2-pyridyl)ethyl>piperazine DL-tartrate (90125-80-7)

Conditions	Yield
1.) excess piperazine, water, 1 h, reflux;	34%

methanol (67-56-1) + DL-tartaric acid (133-37-9) → dimethyl tartrate (405897-14-5)

Conditions	Yield
With hydrogenchloride

methanol (67-56-1) + DL-tartaric acid (133-37-9) → (+/-)-monomethyltartaric acid (3333-46-8, 13856-18-3, 82796-94-9, 89395-25-5)

propan-1-ol (71-23-8) + DL-tartaric acid (133-37-9) → tartaric acid dipropyl ester (4181-80-0)

Conditions	Yield
With hydrogenchloride

ethanol (64-17-5) + DL-tartaric acid (133-37-9) → DL-tartaric acid monoethyl ester (608-89-9)

ethanol (64-17-5) + DL-tartaric acid (133-37-9) → DL-tartaric acid monoethyl ester (608-89-9) + (+/-)-diethyl tartrate (57968-71-5)

Conditions	Yield
With hydrogenchloride

(2S)-2-methyl-1-butanol (1565-80-6) + DL-tartaric acid (133-37-9) → tartaric acid bis-(2-methyl-butyl ester) (343326-54-5)

Conditions	Yield
With hydrogenchloride di--racemat;

Upstream product

• 110-44-1 sorbic Acid 
• 87-73-0 D-glucaric acid 
• 526-99-8 meso-galactaric acid 
• 626-99-3 1,3-butadiene-1-carboxylic acid 
• 56-81-5 glycerol 
• 7664-93-9 sulfuric acid 
• 110-16-7 maleic acid 
• 110-44-1 hexa-2,4-dienoic acid 
• 19071-25-1 (+/-)-2-chloro-3-hydroxy-succinic acid 
• 7732-18-5 water 
• 7647-01-0 hydrogenchloride 
• 3416-24-8 2-amino-2-deoxyglucose 
• 87-69-4 L-Tartaric acid 
• 634-63-9 meso-tartramide 

Downstream Products

• 4054-82-4 tartaric acid diisobutyl ester 
• 72842-25-2 di-O-p-toluoyl-DL-threaric acid-anhydride 
• 498-21-5 2-methylbutanedioic acid 
• 17096-37-6 chlorofumaryl chloride 
• 617-48-1 malic acid 
• 923-06-8 bromosuccinic acid 
• 147-71-7 D-tartaric acid 
• 147-73-9 meso-tartaric acid 
• 87-69-4 L-Tartaric acid 
• 610-20-8 di-O-nitro-tartaric acid 
• 541-50-4 2-acetoacetic acid 
• 17637-11-5 (+/-)-O,O'-dibenzoyltartaric anhydride 
• 87-69-4 tartaric acid 
• 5893-71-0 copper(II) tartrate trihydrate 

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A Systematic Study of the Use of DL-Tartaric acid (cas 133-37-9) in the Synthesis of Silica Materials Obtained by the Sol-Gel Method09/29/2019

DL-tartaric acid was used as a template for the formation of silica nanotubes and spheres by the sol-gel method from tetraethylorthosilicate (TEOS) as silica source. The reactions were carried out in ethanol/water mixtures in the presence of aqueous ammonia, between 0°C and 75°C, using both st...detailed

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