SU740748A1 - Method of preparing 2-chloroethylformate - Google Patents

Description

one

This invention relates to the field of organic synthesis, specifically to an improved process for the preparation of 2-chloroethyl formate, which is used as a plasticizer.

A known method for producing 2-chloroethyl formate by reacting formaldehyde and chloroethyl alcohol in boiling benzene, in the presence of sulfuric acid 1. However, the yield of 2-chloroethyl formate does not exceed 60%.

The closest to the invention to the technical essence and the achieved result is a method for producing 2-chloroethyl formate by treating 1: 5-dioxolane with chlorine, in the presence of a catalyst, iodine, at 80-83 ° C for 3 days. The output of the desired product is 50% 2.

The disadvantage of this method is the low yield of the target product.

The purpose of the invention is to increase the yield of the target product.

The goal is achieved by the described method of obtaining 2chloroethyl formate by treating 1,3-dioxolane with hexachloroethane in the presence of azoisobutyronitrile catalyst, at a temperature of 60-80 ° C and a ratio of 1,3-dioxolane: hexachloroethane: azoisobutyronitrile 1-2: 1: 0,10, 15. The yield of the target product 8090%.

A distinctive feature of the process is the use of hexachloroethane as a chlorinating agent, azoisobutyronitrile as a catalyst, and carrying out the process at a ratio of 1,3-dioxolane

0 hexachloroethane: azoisobutyronitrile. 1-2: 1: 0.1-0.15 at 60-80 ° C.

Example 1. A three-neck flask equipped with a stirrer, a thermometer 15 and a reflux condenser is charged with 0.5 mol (37 g) of 1,3-dioxolane, 0.5 mol (118.5 g) of hexachlorozane and, 0.075 mol (12, 3 g) azoisobutyronitrile. Thus, a ratio of 20 1,3-dioxolane: hexachloroethane: azoisobutyronitrile was 1: 1: 0.15. The reaction was carried out for 10 hours. The mixture was cooled, isolated by distillation at atmospheric pressure 25 43.4 g of 2-chloroethyl formate (yield 80%) with a boiling point of 1.4250.

Found,%: C 33.4; H 4.9; с1 32.9. C H O SR

Calculated,%: C 33.2; H 4.6; Ce 32.1 30 IR spectrum, 1723 cm (C-CC).

Example 2 Analogously to example 1, the reaction temperature, duration 8 hours. 46.1 g (yield 85%) of 2-chloroethyl formate were isolated.

Example 3. Analogously to example 1, the reaction temperature is 80 ° C, the duration of b h.

45.0 g (83% yield) of 2-chloroethyl formate were isolated.

Example 4. Analogously to Example 1, 0.75 mol (55.5 g) of 1,3-dioxolane, 0.5 mol (118.5 g) of hexachloroethane and 0.075 mol (12, Zg) of azioeobutyronitrile are charged. Thus, the ratio of 1,3-dioxolane: hexachloroethane: azoisobutyronitrile was 1: 5-1; 0.15. 43.7 g (yield 81%) of 2-chloroethyl formate,

Example 5. Analogously to Example 1, 1 mol (74 g) of 1,3-dioxolane, 0/5 mol (118.5 g) of hexachloroethane and 0.075 mol (12.3 g) of azo isobutyronitrile are charged. Thus, the ratio of 1,3-dioxolane: hexachloroethane azoisobutyronitrile was 2: 1: 0.15

45.0 g (88% yield) of 2-chloroethyl formate are recovered.

Example 6. Analogously to example 1 download 0.5 mol (37 g) 1,3 dioxolava, 0.5 mol (118.5 g) hexachloroethane and 0.06 mol (9.8 g) azoiso. bu | tironitrile.

Thus, the geo-ratio of 1, 3-dioxolane: hexa Chloroethane: azoisobutyronitrile was 1: 1: O, 12. 42.7 g (79% yield) of 2-chloroethyl formate are recovered.

Example 7. Similarly, Example 1 was charged with 0.5 mol (37 g) of 1,3ioxolane, 0.5 mol (118.5 g), hexaloethane and 0.05 mol (8.2 g) of azoisobutyronitrile. Thus, the ratio is 1, 3-dioxolane; hexachloroethane: azoisobutyronitrile was 1: 1: 0.1; 42.6 g (yield 79%) of 2-chloroethyl formate was isolated.

The use of the proposed method makes it possible: to increase the yield of the desired 2-chloroethyl formate by 30% due to the use of a softer chlorinating agent, which makes it possible to selectively add a chlorine atom.

Claims (2)

1. A method of producing 2-chloroethyl formate by treating 1,3-dioxolane with a chlorinating agent with heating, in the presence of a catalyst, is characterized by the fact that, in order to increase the yield of the target product, hexachloroethane is used as a chlorinating agent, azoisobutyronitrile is used as a catalyst , and the process is carried out at a ratio of 1,3-dioxolane: hexachloroethane: azoisobutyronitrile 1-2: 1: 0.1-0.15 at 60-80 C. Sources of information taken into account in the examination 1, Contardi, Ercoli nternat Congr, Ghem. (Madrid) 1934.5, 163. 2.L.Cort, R.Pearson. O.Chem.Soc. 1960, 1682 (prototype).