Chloroacetic acid

Chloroacetic acid, which falls under the category of halogenated acetic acid derivatives, is distinguished by the inclusion of a chlorine atom within its molecular structure. This particular compound manifests as a colorless, crystalline solid, showcasing its physical form. Notably, it possesses a high degree of solubility in water, making it readily miscible in aqueous environments.

1.Industrial production of chloroacetic acid has three main methods. (1) acetic acid chlorination is iodine, phosphorus, sulfur or phosphorus and sulfur halide catalyst in the presence of chlorine with acetic acid obtained by direct chlorination. In addition to the generation of chloroacetic acid, there are deep-chlorinated by-products such as dichloroacetic acid, trichloroacetic acid. This method of raw material consumption is low, simple process, chloroacetic acid yield of up to 92%. (2) trichlorethylene hydration method is 93% sulfuric acid as the catalyst, the reaction temperature of about 160-180 ℃. This method can be high purity chloroacetic acid, the yield of up to 90%, but more hydrochloric acid by-product. (3) chlorohydrin oxidation method is 60 ℃ 60% nitric acid oxidation, chloroacetic acid yield of more than 90%. In North America, mainly by acetic acid chlorination, Western Europe to TCE mainly hydrated. China's use of acetic acid chloride production: the amount of acetic acid to the reaction pot, the weight of glacial acetic acid 3.5% sulfur powder as a catalyst, preheated to 90 ℃ or more, the beginning of access to the right amount of chlorine, two reactor series chlorine , The main pot control temperature of 98 ± 2 ℃, Vice pot is 85-90 ℃, chlorine rate of about 70kg / h, to be the reaction pot material relative density of 1.350 (80 ℃), the reaction reaches the end. The reaction is pumped to the acid tank, cooling crystallization, the liquid phase is a small amount of acetic acid, dichloroacetic acid, sulfur chloride and a small amount of chloroacetic acid, separated from the crystal, and then the following 38 ℃ mother liquor is finished. Per ton of products produced about 150 kg of mother liquor, can be further chlorinated into dichloroacetic acid, methyl dichloroacetate and chloroform. TCE addition of water and hydrolysis of the same time: the reaction temperature of 160-180 ℃, sulfuric acid concentration in the reaction should be maintained at 93%, control the proportion of trichlorethylene and water. Sulfuric acid consumption of not more than 50kg, 30% by-product hydrochloric acid 2.57t. Chloroacetic acid for industrial products is colorless or slightly yellow crystals. Consumption of raw materials fixed: acetic acid (98%) 730kg / t, chlorine 860kg / t, sulfur 26kg / t. Purification method: chloroform, carbon tetrachloride, benzene or water recrystallization, into a vacuum desiccator with phosphorus pentoxide or concentrated sulfuric acid drying. For further purification, distillation may be carried out in the presence of magnesium sulfate. The distillate is melted and crystallized in steps, and the product is stored under vacuum or in dry nitrogen. (4) in the presence of acetic anhydride to the chlorine in the acid can be made from chloroacetic acid: refined by distillation that chloroacetic acid products. (5) take industrial chloroacetic acid at 35 ~ 40 ℃ placed about half a month, the crystallization of liquid acetic acid and dichloroacetic acid, and then dissolved in benzene, steamed out part of the benzene, stop heating and cooling recrystallization, filtration Crystallization, in order to remove trichloroacetic acid, benzene and a small amount of ether washing, that was anhydrous pure chloroacetic acid. 2. Preparation: In a reaction flask (preweighed) equipped with a stirrer, a thermometer, a reflux condenser (connected to a trachea to a hydrogen chloride gas absorption device) and a vent tube (extending into the bottom of the bottle), glacial acetic acid (2) 150g (2.5mol), red phosphorus 6g, heated to 100 ℃, slowly into the chlorine gas, keep the reaction ℃ in between 105 ~ 110 ℃. Until the mass increase of about 85g, about 5h. Distillation, the first to collect the lower boiling point of acetyl chloride and unreacted acetic acid, and then collected 150 ~ 200 ℃ distillate. The liquid of the fraction is cooled and solidified. As much as possible to dump uncured liquid, the solid re-distillation, collecting 182 ~ 192 ° C fraction, after cooling mp 63 ℃, in chloroacetic acid (1) 150-175 g, yield 64- 74%.

1. Used in a wide range of organic synthetic materials. Dyestuff industry is used to produce indigo and naphthalene aminoacetic acid dyes; in the pharmaceutical industry, it is used to synthesize caffeine, barbiturate, epinephrine, vitamin B6, glycine, malonate and other drugs and intermediates; in the pesticide industry Production of more than 20 pesticides such as herbicide 24-D, butyl ester, 245-T, thiocyanate, α-naphthaleneacetic acid, glyphosate, alachlor, acetochlor, butachlor, and the ins

Molecular Weight:94.50
XLogP3:0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:93.9821570
Monoisotopic Mass:93.9821570
Topological Polar Surface Area:37.3
Heavy Atom Count:5
Complexity:42.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes