The method of obtaining bis( beta-chloroethyl)vinylphosphonate

 

(57) Abstract:

The inventive product - bis-(chloroethyl)vinylphosphonate, CF6H11Cl2O3P. Reagent 1: ClCH2CH2P(O) (OCH2CH2Cl302. Reagent 2: carbonate of an alkali metal. Reaction conditions: when 90-130oWith catalyst - product of the interaction of aliphatic monohydroxy alcohol, ethylene glycol, glycerol or phenol with a boron reagent when the molar ratio of 1-50:1. 1 C.p. f-crystals, 1 table.

The invention relates to a technology for obtaining esters vinylphosphonic acid, which finds wide use as a reactive flame retardants and plasticizers in the production of various polymer materials.

A method of obtaining bis-(chloroethyl)-vinylphosphonate the dehydrochlorination bis-(b-chloroethyl)-chloroethyl)-chloroethylphosphonic carbonate or bicarbonate of an alkali metal in an inert solvent at 120oC. in a stream of nitrogen. The resulting reaction mass is then cooled to 20-25oWith and washed with water. The washing water is extracted with benzene (3 x 50 ml) and combine the organic layers. The benzene is distilled off, the residue is washed with water, the pH of which brought others>3D0=1,4755[1]

The disadvantage of this method is the use of acetic acid is explosive and corrosive product and benzene-explosive product.

Closest to the claimed invention is a method for bis-(chloroethyl)-vinylphosphonate the dehydrochlorination bis-(b-chloroethyl)-chloroethylphosphonic carbonate or bicarbonate of an alkali metal in the presence of acetic acid without solvent or in the presence of inert solvents (acetone, acetonitrile, benzene and others) in a stream of nitrogen at 25-225oWith, mainly 115-125oC. After cooling the reaction mass to 205oWith the dissolving of salt add water, separate the organic layer and aqueous layer is extracted with benzene dissolved product. The benzene layer is combined with the product and washed with aqueous sodium bicarbonate solution at pH 7-8. Distilled benzene, and then water, heating in vacuum to 100oC. the Distillation allocate fractions 113-130oC at 0.3 mm RT.article The yield of the target product 97% [2]

The disadvantage of this method is the use of explosive acetic acid and benzene and carrying out distillation of the desired product at a high vacuum.

oC and a molar ratio of bis-(b-chloroethyl)-chloroethylphosphonic: boron compound 1:0,002 0,01 followed by cooling the reaction mixture, dissolving the salt water, treatment with chloroform at 0 to 10oWith the separation of the layers, washing the organic layer with aqueous ammonia or sodium carbonate at 0 to 10oWith, then with water until neutral environment, distillation of the chloroform and drying of the target product at 100-120oWith the vacuum.

The invention is illustrated by examples in the table. All the experiments reflected in the table, carried out according to the method described in example 1.

To 150 g (0,423 mole) of bis-(b-chloroethyl)-chloroethylphosphonic (76%) are added 1.5 g (0,024 mole) of ethylene glycol, 0.3 g (0,005 mol) of boric acid (for education in the reaction mixture of catalyst) and 42.5 g (0.4 mole) of sodium carbonate. The reaction is carried out under stirring in a stream of nitrogen and a temperature of 110-115oC for 2.5 h prior to the absence hlaut to dissolve salts and again cooled to 53oC. To the cooled mixture is added 100 ml of chloroform so that the temperature was in the range of 2-8oC. After separation the organic layer was washed with ammonia water with a mass fraction of ammonia 2% (2 x 100 ml) at a temperature of 2-8oWith, and then with water until neutral environment (pH 7-8,5).

Then distilled chloroform by heating the product up to 100-110oWith, and dried in a vacuum of 60 mm RT. tbsp. at a temperature of 100-120oC. Get to 101.3 g of bis-(b-chloroethyl)-vinylphosphonate content mass fraction of the basic substance to the double bond of 91.8% and output 94,35% calculated on the base material, n2D0=1,477, appearance colourless liquid (40 units on a scale Hazen).

1. The method of obtaining bis (chloroethyl)-vinylphosphonate the dehydrochlorination bis(b-chloroethyl)-b-chloroethylphosphonic carbonate of an alkali metal in the presence of a catalyst at a temperature of 90 to 130oWith cooling of the reaction mixture, dissolving the salt water, by treatment with a solvent, separation of layers and selection of the target product, wherein the catalyst used is the product of the interaction of aliphatic monohydroxy alcohol, ethylene glycol, glycerol or phenol with a boron reagent when their molar ratio, RT at 0, 10oWith, the organic layer is washed at a temperature of 0 to 10oWith a solution of ammonia or sodium carbonate, then with water until neutral environment, distilled chloroform and dried target product at 100 120oWith the vacuum.

2. The method according to p. 1, characterized in that as boron reagent use boric acid, sodium tetraborate, or boron oxide.

 

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