Mercaptoacetic acid Chemical Properties

Melting point:

−16 °C(lit.)

Boiling point:

96 °C5 mm Hg(lit.)

Density 

1.326 g/mL at 20 °C(lit.)

vapor density 

3.2 (vs air)

vapor pressure 

0.4 mm Hg ( 25 °C)

refractive index 

n20/D 1.505(lit.)

Flash point:

126 °C

storage temp. 

Store at +2°C to +8°C.

solubility 

Chloroform (Sparingly), Methanol (Sparingly)

form 

Liquid

pka

3.68(at 25℃)

color 

clear clear, colorless

Odor

strong unpleasant odor

PH

1 (H2O, 20℃)

Water Solubility 

soluble

Sensitive 

Air Sensitive

Merck 

14,9336

BRN 

506166

Exposure limits

TLV-TWA 1 ppm (～3.8 mg/m³) (ACGIH).

Stability:

Air Sensitive

InChIKey

CWERGRDVMFNCDR-UHFFFAOYSA-N

LogP

0.090

CAS DataBase Reference

68-11-1(CAS DataBase Reference)

NIST Chemistry Reference

Acetic acid, mercapto-(68-11-1)

EPA Substance Registry System

Thioglycolic acid (68-11-1)

Safety Information

Hazard Codes 

T,T+

Risk Statements 

23/24/25-34-26-24/25

Safety Statements 

25-27-28-45-36/37-28C-23

RIDADR 

UN 1940 8/PG 2

WGK Germany 

1

RTECS 

AI5950000

F 

9-13-23

Autoignition Temperature

662 °F

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29309070

Hazardous Substances Data

68-11-1(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 0.15 ml/kg (Deichmann, Mergard)

MSDS

• Language:English Provider:Mercaptoacetic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Mercaptoacetic acid Usage And Synthesis

Description

Thio glycolic acid (TGA) is the organic compound HSCH₂CO₂H . It contains both a thiol (mercaptan) and a carboxylic acid. It is a clear liquid with a strong unpleasant odor. It is readily oxidized by air to the corresponding disulfide [SCH₂CO₂H]₂.
TGA was developed in the 1940s for use as a chemical depilatory and is still used as such, especially in salt forms, including calcium thioglycolate and sodium thioglycolate. TGA is the precursor to ammonium thioglycolate that is used for permanents. TGA and its derivatives break the disulfide bonds in the cortex of hair. One reforms these broken bonds in giving hair a "perm." Alternatively and more commonly, the process leads to depilation as is done commonly in leather processing. It is also used as an acidity indicator, manufacturing of thioglycolates, and in bacteriology for preparation of thioglycolate media.
TGA is also used in the making of tin stabilizers often used in certain polyvinyl chloride products (such as vinyl siding).
TGA, usually as its dianion, forms complexes with metal ions. Such complexes have been used for the detection of iron, molybdenum, silver, and tin.
Thioglycolic acid is used as nucleophile in thioglycolysis reactions used on condensed tannins to study their structure.

Chemical Properties

Thioglycolic acid is a colorless liquid with a strong unpleasant odor like rotten eggs.

Chemical Properties

Also known as mercaptoacetic acid, HSCH2COOH is a colorless liquid with a strong unpleasant odor. Used as a reagent for metals such as iron, molybdenum, silver, and tin,and in bacteriology.

Uses

Thioglycolic Acid is an organic compound containing both a thiol and a carboxylic acid. Thioglycolic Acid is a precursor to ammonium thioglycolate, a chemical used for permanents. Thioglycolic Acid is used in organic synthesis as a nucleophile in thioglycolysis reactions and is used as a S transfer agent for sulfonyl chloride synthesis.

Uses

Sensitive reagent for iron, molybdenum, silver, tin. With ferric iron a blue color appears, and when an alkali hydroxide is added to a solution contg ferrous salts and thioglycolic acid, a yellow precipitate forms. Used in the manufacture of thioglycolates. The ammonium and sodium salts are commonly used for cold waving and the calcium salt is a depilatory. The sodium salt also is used in bacteriology in the preparation of thioglycolate media.

Uses

Mercaptoacetic acid is used as a reagent formetals analysis; in the manufacture of thioglycolates, pharmaceuticals, and permanentwave solutions; and as a vinyl stabilizer.

Application

Thioglycolic acid is an intermediate in the production of thiomethoprol (caputril), biotin, thiozinc acid, sodium dithiosuccinate and other pharmaceuticals, and is also an intermediate in the synthesis of cysteine, hormonal agent, and industrial disinfectant. And an important raw material for the synthesis of sulfuric acid. Thioglycolic acid is used as antioxidant and stabilizer in pharmaceuticals to enhance the stability of the main drug and prolong the validity period of pharmaceutical preparations. Ammonium and sodium salts of thioglycolic acid are mainly used as curling agents, calcium salts can be used as depilatory agents, polymerization initiators, accelerators and chain transfer agents, and can be used for hair removal before cosmetic surgery and animal experiments. Thioglycolic acid is used to make epoxy resin, catalyst of bisphenol A, and it can also be used as the basic raw material for synthesizing PVC transparent plastic and organic antimony and organic tin heat stabilizer.
Thioglycolic acid is a sensitive reagent for the determination of iron, molybdenum, aluminum, tin, etc., and is an inhibitor of copper sulfide and iron sulfide minerals in beneficiation. In the petrochemical industry and the railway sector, it is used for cleaning and derusting of equipment and rails. It can be used as a crystallization nucleating agent in polypropylene processing and molding, as a modifier for coatings and fibers, as a blanket quickening agent, as a stabilizer raw material for polyvinyl chloride and rubber, as a cold perm agent, and as a pharmaceutical intermediate. Thioglycolic acid is used as a color developer for the photometric determination of molybdenum, rhenium and iron, and as a compounding masking agent.

Definition

ChEBI: Thioglycolic acid is a sulfur-containing carboxylic acid. It is a conjugate acid of a thioglycolate(1-).

General Description

A colorless liquid with an unpleasant odor. Density 1.325 g / cm3. Used to make permanent wave solutions and depilatories. Corrosive to metals and tissue.

Air & Water Reactions

Readily oxidized by air. Water soluble.

Reactivity Profile

Mercaptoacetic acid is readily oxidized by air . Reacts readily with other oxidizing agents as well in reactions that may generate toxic gases. Incompatible with diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials may generate heat and toxic and flammable gases. May react with acids to liberate hydrogen sulfide. Neutralizes bases in exothermic reactions. Reacts with cyanides, sulfites, nitrites, thiosulfates to generate flammable and toxic gases and heat. Reacts with carbonates and bicarbonates.

Hazard

Toxic by ingestion and inhalation, strong irritant to tissue, eyes, and skin.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Health Hazard

Mercaptoacetic acid is a highly toxic and ablistering compound. Even a 10% solutionwas lethal to most experimental animals by dermal absorption. The oral LD50 value ofundiluted acid is less than 50 mg/kg (Patty1963). The lethal dose in rabbits by skinabsorption is 300 mg/kg. The acute toxicsymptoms in test animals include weakness,respiratory distress, convulsions, irritation ofthe gastrointestinal tract, and liver damage.
Mercaptoacetic acid is a severe irritant.Contact with eyes can cause conjunctivalinflammation and corneal opacity. Skin contact can result in burns and necrosis.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Safety Profile

Poison by ingestion, skin contact, intraperitoneal, and intravenous routes. Moderately toxic by subcutaneous route. A corrosive irritant to skin, eyes, and mucous membranes. When heated to decomposition it emits toxic fumes of SOx. See also MERCAPTANS and HYDROGEN SULFIDE.

Potential Exposure

Thioglycolic acid is used to make thioglycolates; in sensitivity tests for iron; in formulations of permanent wave solutions and depilatories; in pharmaceutical manufacture; as a stabilizer in vinyl plastics.

Carcinogenicity

Thioglycolic acid was not mutagenic in a number of Salmonella typhimurium strains with or without metabolic activation.

Shipping

UN1940 Thyoglycolic acid, Hazard class: 8; Labels: 8-Corrosive material.

Purification Methods

Mix the acid with an equal volume of *benzene; the *benzene is then distilled off to dehydrate the acid. After heating to 100o to remove most of the *benzene, the residue is distilled under vacuum and stored in sealed ampoules at 3o. [Eshelman et al. Anal Chem 22 844 1960, Beilstein 3 IV 1130.]

Incompatibilities

Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur). Air, strong oxidizers; bases, active metals, for example, sodium potassium, magnesium, and calcium. Readily oxidized by air. Thermal decomposition causes release of hydrogen sulfide. May attack various metals.

Waste Disposal

Dissolve in flammable solvent and burn in furnace equipped with afterburner and alkaline scrubber.

Mercaptoacetic acid(68-11-1)Related Product Information

• 1,1'-Thiobisethane
• Methyl thioglycolate
• Stearic acid
• Glycolic acid
• POLY(2-HYDROXYACETIC ACID)
• Methyl glycolate
• 2-Phenylethanethiol
• SODIUM ETHANETHIOLATE
• ETHYL THIOGLYCOLATE
• Sodium glycolate
• Ethanethiol
• Folic acid
• Hyaluronic acid
• Citric acid
• Ethyl 2-(Chlorosulfonyl)acetate
• 2-Thiobarbituric acid
• calcium sulphidoacetate
• THIOGLYCOLIC ACID SODIUM SALT (MERCAPTOACETIC ACID SODIUM SALT),Mercaptoacetic acid sodium salt, Thioglycolic acid sodium salt
• Mercaptoacetic
• Thioglycolic
• Thioglycolic Acid