SU929630A1 - Process for producing di- or trioxydiphenyl sulfones - Google Patents

Description

t

The invention relates to an improved process for the preparation of diyl trioxydiphenyl sulfones, widely used in pharmacology, the production of rubber and anion exchange resins.

A method of producing dioxydiphenylsulfones by sulfonating phenols in fuming sulfuric acid is known.

: at elevated temperatures up to

200 ° C 1.

The disadvantage of this method is to carry out the process in an aggressive environment and its associated limited applicability for the synthesis of compounds containing labile functional groups.

Closest to the invention is a method for the preparation of dioxydiphenylsulfones, which consists in the interaction of quinone and benzenesulfinic acid in water at room temperature 2.

Z

However, quinones used in the known method are inaccessible and unstable compounds. This method is unsuitable for the preparation of trioxydiphenylsulfones, since the corresponding quinones containing a hydroxyl group are unknown. .

The purpose of the invention is to simplify the process.

This goal is achieved in that according to the method for producing diyl trioxydiphenylsulfone phenol. reacted with benzenesulfinic acid in the presence of peroxidase and hydrogen peroxide

15 or O-diphenol oxidase in water at pH 5-9 and a temperature of 18-35 ° C.

The use of available phenols as starting compounds leads to a simplification of the process. Commercial preparations of enzymes or made from plant tissues can be used. The method of preparation of preparations is simple and cheap.

A portion of plant tissue (blocks, potatoes) is ground in a porcelain mortar cold, washed with cold acetone until the filtrate remains colorless. The powder is dried and used in the work.

The optimal yield of the target products is when using peroxidase and hydrogen peroxide in the ratio of 1/500 and 1/700.

Example 1. A mixture of an aqueous 0.1 M solution of pyrocatechol and 0.2 M of benzenesulfinic acid (pH 8–9.5) was added 100 mg of peroxidase in 10 ml of water and 50 ml of 3% Npo. The mixture is shaken and left for min. At the end of the precipitation, the solution is filtered. The diarylsulfone obtained is purified by recrystallization. Data on the yield of the reaction products (diarylsulfones) depending on the ratio of peroxidase to hydrogen peroxide, i.e. on the concentration of oxidant, are given in table.1.

Example 2. To a mixture of a 0.02 M solution of the fnol compound and 0.0 M benzenesulfinic acid (pH) was added 200 mg of the enzyme preparation o-diphenol oxidase. The mixture was shaken and left for 1 hour. The precipitate formed was separated by filtration.

The output of diarylsulfonov is 96-98% of the original.

Table 2 shows the yield of substituted diarylsulfones upon catalysis by o-diphenol oxidase.

-

The advantages of the proposed method are the high selectivity of the process - the production of predominantly ortho-isomers, the absence of by-products, a high reaction rate, the cheapening of the process when using enzyme preparations as an oxidant, an increase in the yield of products by 10-15% compared with the known method.

Table 1

table 2

Claims (2)

1. Patent CqCP f, cl. C 07 C U7 / 02, 1966. 2.J. et.al. Kinetics of, in addition to benzenesulfinic acid to benzoquinone. Tetrahedron, 25,2715 1969 (prototype).