|Jmol-3D images||Image 1|
|Molar mass||94.50 g mol−1|
|Appearance||Colorless or white crystals|
|Density||1.58 g·cm−3, solid|
|Melting point||63 °C (145 °F; 336 K)|
|Boiling point||189.3 °C (372.7 °F; 462.4 K)|
|Solubility in water||85.8 g/100mL (25 °C)|
|Solubility||soluble in methanol, acetone, diethyl ether, benzene, chloroform, ethanol|
|Vapor pressure||0.22 hPa|
|Refractive index (nD)||1.4351 (55 °C)|
heat capacity C
|144.02 J/K mol|
|Std enthalpy of
|R-phrases||R25 R34 R50|
|S-phrases||S23 S37 S45 S61|
|Main hazards||alkylating agent|
|Flash point||126 °C (259 °F; 399 K)|
|Autoignition temperature||< 500 °C|
|LD50||165 mg/kg (mouse, oral)|
|Related compounds||2-chloropropionic acid
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
The production of chloroacetic acid was 706,000 tonnes/year in 2010, of which over half is produced in China. Other countries with significant production capacity are Germany (105,000), the Netherlands (100,000), India (>65,000), and the United States (55,000). The world's largest producer is Akzo Nobel.
2H + Cl
2 → ClCH
2H + HCl
2CHCl + 2 H
2O → ClCH
2H + 2 HCl
The hydrolysis method produces a highly pure product, which can be important since mono-, di-, and trichloroacetic acids are difficult to separate by distillation. Approximately, 420,000,000 kg/y are produced globally.
Reactivity and uses
In industry, chloroacetic acid is used in the production of a wide variety of useful compounds; e.g., drugs, dyes, pesticides. Most reactions take advantage of the high reactivity of the C–Cl bond. It is the precursor to the herbicide glyphosate, and the herbicides MCPA (2-methyl-4-chlorophenoxyacetic acid) and dimethoate are prepared by alkylation with chloroacetic acid. Chloroacetic acid is converted to chloroacetyl chloride, a precursor to adrenaline (epinephrine). Displacement of chloride by sulfide gives thioglycolic acid, which is used as a stabilizer in PVC and a component in some cosmetics.
Chloroacetic acid easily penetrates skin and mucous membranes and interferes with cellular energy production. Initial dermal exposure to high concentrations (e.g., 80% solution) may not appear very damaging at first, however systemic poisoning may present within hours. Exposure can be fatal if greater than 6% body surface area is exposed to chloroacetic acid. The sodium salt does not penetrate the skin as well as the acid but can be as damaging given a longer duration and greater surface area of exposure.
Upon exposure to chloroacetic acid, immediate decontamination should be commenced by rinsing the affected area with water or bicarbonate solution in order to neutralize the acid and prevent further skin absorption.
- Dippy, J. F. J.; Hughes, S. R. C.; Rozanski, A. (1959). "498. The dissociation constants of some symmetrically disubstituted succinic acids". Journal of the Chemical Society 1959: 2492–2498. doi:10.1039/JR9590002492.
- Malveda, M. P. (2011). "CEH Marketing Research Report: MONOCHLOROACETIC ACID". Chemical Economics Handbook. SRI consulting. Retrieved July 2011.
- Koenig, G.; Lohmar, E.; Rupprich, N. (2005), "Chloroacetic Acids", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a06_537
- Burgstahler, A. W.; Worden, L. R. (1966), "Coumarone", Org. Synth. 46: 28; Coll. Vol. 5: 251
- Antidote treatment
- Mitroka, J.G. 1989. Monochloroacetic Acid Lethality in the Rat in Relation to Lactic Acid Accumulation in the Cerebrospinal Fluid. Ph.D. Dissertation, Rutgers, State University of New Jersey, New Brunswick, NJ.;
- Régnier JF, et al. Experimental evaluation of potential antidotes for monochloroacetic acid (MCA) acute poisoning. Hum Exp Toxicol 1996;15:850.