Chloroacetic acid, physical properties

The physical properties of cyanoacetic acid [372-09-8] and two of its ester derivatives are Hsted ia Table 11 (82). The parent acid is a strong organic acid with a dissociation constant at 25°C of 3.36 x 10. It is prepared by the reaction of chloroacetic acid with sodium cyanide. It is hygroscopic and highly soluble ia alcohols and diethyl ether but iasoluble ia both aromatic and aUphatic hydrocarbons. It undergoes typical nitrile and acid reactions but the presence of the nitrile and the carboxyUc acid on the same carbon cause the hydrogens on C-2 to be readily replaced. The resulting malonic acid derivative decarboxylates to a substituted acrylonitrile ... 

Physical Properties. Pure chloroacetic acid [79-11-8] (CICH2COOH), mol wt 94.50, C2H2CIO2, is a colorless, white dehquescent soHd. It has... 

Dichloroacetic acid [79-43-6] (CI2CHCOOH), mol wt 128.94, C2H2CI2O2, is a reactive intermediate in organic synthesis. Physical properties are mp 13.9°C, bp 194°C, density 1.5634 g/mL, and refractive index 1.4658, both at 20°C. The Hquid is totally miscible in water, ethyl alcohol, and ether. Dichloroacetic acid K = 5.14 X 10 ) is a stronger acid than chloroacetic acid. Most chemical reactions are similar to those of chloroacetic acid, although both chlorine... 

Chloroacetyl chloride [79-04-9] (CICH2COCI) is the corresponding acid chloride of chloroacetic acid (see Acetyl chloride). Physical properties include mol wt 112.94, C2H2CI2O, mp —21.8 C, bp 106°C, vapor pressure 3.3 kPa (25 mm Hg) at 25°C, 12 kPa (90 mm Hg) at 50°C, and density 1.4202 g/mL and refractive index 1.4530, both at 20°C. Chloroacetyl chloride has a sharp, pungent, irritating odor. It is miscible with acetone and bensene and is initially insoluble in water. A slow reaction at the water—chloroactyl chloride interface, however, produces chloroacetic acid. When sufficient acid is formed to solubilize the two phases, a violent reaction forming chloroacetic acid and HCl occurs. 

Production of cellulose esters from aromatic acids has not been commercialized because of unfavorable economics. These esters are usually prepared from highly reactive regenerated cellulose, and their physical properties do not differ markedly from cellulose esters prepared from the more readily available aHphatic acids. Benzoate esters have been prepared from regenerated cellulose with benzoyl chloride in pyridine—nitrobenzene (27) or benzene (28). These benzoate esters are soluble in common organic solvents such as acetone or chloroform. Benzoate esters, as well as the nitrochloro-, and methoxy-substituted benzoates, have been prepared from cellulose with the appropriate aromatic acid and chloroacetic anhydride as the impelling agent and magnesium perchlorate as the catalyst (29). 

See also Carboxymethyl celluloses applications, 5 452t in paper manufacture, 18 115 physical properties, 5 450t production from chloroacetic acid,... 

Chloroacetaldehyde, production from acetaldehyde, 1 105 Chloroacetamide, l 142 herbicides, 13 303 Chloroacetate esters, 1 142 physical properties of, 1 142t Chloroacetic acid, 1 136-139 end use of chlorine, 6 135t physical properties of, l 137t producers, l 139t... 

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