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Chloroacetic acid

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Chloroacetic acid Basic information

Product Name:
Chloroacetic acid
Synonyms:
  • acidechloroacetique
  • acidechloroacetique(french)
  • acidemonochloracetique
  • acidemonochloracetique(french)
  • acidemonochloracetique(solide)
  • acidemonochloracetique(solutions)
  • Acidomonocloroacetico
  • alpha-Chloroacetic acid
CAS:
79-11-8
MF:
C2H3ClO2
MW:
94.5
EINECS:
201-178-4
Product Categories:
  • API Intermediate
  • 500 Series Drinking Water Methods
  • EPA
  • Method 552
  • omega-Chlorocarboxylic Acids
  • omega-Functional Alkanols, Carboxylic Acids, Amines & Halides
  • Pharmaceutical Intermediates
  • Other Reagents
  • Miscellaneous Reagents
  • Aliphatics
  • Aliphatics, Miscellaneous Reagents
Mol File:
79-11-8.mol
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Chloroacetic acid Chemical Properties

Melting point:
61 °C
Boiling point:
189 °C(lit.)
Density 
1.58
vapor density 
3.26 (vs air)
vapor pressure 
0.75 mm Hg ( 20 °C)
refractive index 
1.4330
Flash point:
126°C
storage temp. 
0-6°C
solubility 
Soluble in methanol, acetone, diethyl ether, benzene, chloroform and ethanol.
pka
2.85(at 25℃)
form 
Liquid
color 
White
Odor
Penetrating, burning odor
PH Range
< 1 at 800 g/l at 20 °C
explosive limit
8%
Water Solubility 
SOLUBLE
Sensitive 
Hygroscopic
Merck 
14,2112
BRN 
605438
Stability:
Stable. Deliquescent. Incompatible with strong bases, alkalies, most common metals, strong oxidizing agents.
CAS DataBase Reference
79-11-8(CAS DataBase Reference)
NIST Chemistry Reference
Acetic acid, chloro-(79-11-8)
EPA Substance Registry System
Chloroacetic acid (79-11-8)
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Safety Information

Hazard Codes 
T,N,Xi,F
Risk Statements 
25-34-50-40-36/37/38-23/24/25-38
Safety Statements 
23-37-45-61-36-26-16-63-36/37/39
RIDADR 
UN 1751 6.1/PG 2
WGK Germany 
2
RTECS 
AF8575000
3
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
II
HS Code 
29154000
Hazardous Substances Data
79-11-8(Hazardous Substances Data)

MSDS

  • Language:English Provider:MCA
  • Language:English Provider:SigmaAldrich
  • Language:English Provider:ALFA
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Chloroacetic acid Usage And Synthesis

Chemical Properties

colourless or white crystals

Chemical Properties

Chloroacetic acid is a colorless to white crystalline solid. It has a strong vinegar-like odor and an Odor Threshold of 0.15 milligram per cubic meter.

Uses

Herbicide, preservative, bacteriostat, intermediate in production of carboxymethylcellulose; ethyl chloroacetate, glycine, synthetic caffeine, sarcosine, thioglycolic acid, EDTA, 2,4-D, 2,4,5-T.

Uses

Chloroacetic acid behaves as a very strong monobasic acid and is used as a strong acid catalyst for diverse reactions. The Cl function can be displaced in base-catalyzed reactions.

Definition

A colorless crystalline solid made by substituting one of the hydrogen atoms of the methyl group of ethanoic acid with chlorine, using red phosphorus. It is a stronger acid than ethanoic acid because of the electron-withdrawing effect of the chlorine atom. Dichloroethanoic acid (dichloroacetic acid, CHCl2COOH) and trichloroethanoic acid (trichloroacetic acid,CCl3COOH) are made in the same way. The acid strength increases with the number of chlorine atoms present.

Production Methods

Chloroacetic acid can be synthesized by the radical chlorination of acetic acid, treatment of trichloroethylene with concentrated H2SO4, oxidation of 1,2-dichloroethane or chloroacetaldehyde, amine displacement from glycine, or chlorination of ketene.

Definition

ChEBI: A chlorocarboxylic acid that is acetic acid carrying a 2-chloro substituent.

General Description

Chloroacetic acid, solution is a colorless solution of the white crystalline solid. The acid concentration can be up to 80%.It is used in manufacturing dyes and in medicine. Chloroacetic acid is toxic by inhalation, ingestion and skin contact. Chloroacetic acid is corrosive to metals and tissue. Chloroacetic acid is used as an herbicide, preservative and bacteriostat.

Air & Water Reactions

Water soluble.

Reactivity Profile

These organic compounds donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Chloroacetic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Hazard

Use in foods prohibited by FDA. Irritating and corrosive to skin. Upper respiratory tract irritant. Questionable carcinogen.

Health Hazard

Inhalation causes mucous membrane irritation. Contact with liquid causes severe irritation and burns of the eyes and irritation and burns of skin. Ingestion causes burns of mouth and stomach.

Fire Hazard

Special Hazards of Combustion Products: Toxic gases, such as hydrogen chloride, phosgene and carbon monoxide, may be generated.

Safety Profile

Poison by ingestion, inhalation, subcutaneous, and intravenous routes. A corrosive skin, eye, and mucous membrane irritant. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Combustible liquid when exposed to heat or flame. To fight fire, use water spray, fog, mist, dry chemical, foam. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORIDES.

Potential Exposure

This haloacetic acid can be a byproduct of drinking water disinfection and may increase the risk of cancer. Monochloracetic acid is used primarily as a chemical intermediate in the synthesis of sodium carboxymethyl cellulose; and such other diverse substances as ethyl chloroacetate, glycine, synthetic caffeine, sarcosine, thioglycolic acid, and various dyes. Hence, workers in these areas are affected. It is also used as an herbicide. Therefore, formulators and applicators of such herbicides are affected.

Shipping

UN1750 (liquid) & UN1751 (solid) Chloroacetic acid, solid or liquid, Hazard class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 8-Corrosive material.

Purification Methods

Crystallise the acid from CHCl3, CCl4, *benzene or water. Dry it over P2O5 or conc H2SO4 in a vacuum desiccator. Further purification is by distillation from MgSO4, and by fractional crystallisation from the melt. Store it under vacuum or under dry N2. [Bernasconi et al. J Am Chem Soc 107 3621 1985, Beilstein 2 IV 474.]

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, sulfides (releasing heat, toxic, and possibly flammable gases), thiosulfates, and dithionites (releasing hydrogen sulfate and oxides of sulfur). The solution in water is a strong acid. Contact with strong oxidizers, strong bases; and strong reducing agents such as hydrides can cause violent reactions. Chloracetic acid decomposes on heating, producing toxic and corrosive hydrogen chloride, phosgene, and carbon monoxide gases. Attacks metals in the presence of moisture.

Waste Disposal

Incineration, preferably after mixing with another combustible fuel; care must be exercised to assure complete combustion to prevent the formation of phosgene; an acid scrubber is necessary to remove the halo acids produced.

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