RU2159764C1 - Method of preparing 4,4'-dichlorodiphenyl sulfoxide - Google Patents

Abstract

FIELD: fine organic synthesis, more particularly preparation of chlorinated aromatic sulfoxides. SUBSTANCE: 4,4'-dichlorodiphenyl sulfoxide is prepared by reacting sulfide with sulfuryl chloride. Diphenyl sulfide is first dissolved in carbon tetrachloride, and reaction is carried out in the presence of aluminium chloride at 0-5 C. Invention makes it possible to prepare 4,4'-dichlorodiphynyl sulfoxide by technologically simple method using available compounds with high yield (94%). Method uses simple equipment and has industrial application. EFFECT: more efficient preparation method.

Description

 The invention relates to the field of organic sulfur compounds, and more specifically to the field of production of chlorinated aromatic sulfoxides.

 The invention can most effectively be used in fine organic synthesis and in the production of sulfur-containing polymers.

 A known method of chlorination of aromatic sulfur-containing compounds by chlorination of diphenyl sulfide with molecular chlorine in a non-polar solvent under cooling (F. Krafft, Ber., 7, 1874, p, 1164-65).

A known method of chlorination of benzyl sulfoxides with sulfuryl chloride in a non-polar organic solvent at a temperature of -15 -0 ^o C (Meers CA, McCollum Gj. Tetrahedron Lett., 1973, 4, p. 289).

 However, these methods do not lead to the formation of 4,4'-dichlorodiphenyl sulfoxide.

A known method for producing 4,4'-dichlorodiphenyl sulfoxide by reacting 4,4'-dichlorodiphenyl sulfide dissolved in a 75% aqueous solution of acetonitrile with cerium ammonium nitrate at room temperature, followed by dilution of the reaction mixture with water and extraction of the resulting product with ether (CM Wong, T.-L. But, Synthesis, 1972, p. 561) /
The disadvantage of this method is the use of hard-to-reach starting compounds, as well as low technological isolation of the finished product.

Closest to the proposed invention in technical essence is a method for producing a chlorinated aromatic sulfur-containing compound by reacting diphenyl sulfoxide with sulfuryl chloride, taken in a molar ratio of 1: 2-2.2, at a temperature of 18-25 ^o C (RF patent N 2122538, priority 22.07.96 g.), selected by us for the prototype.

 However, it is not possible to obtain 4,4'-dichlorodiphenyl sulfoxide using this method.

 The objective of the present invention is to develop a technological method for producing 4,4'-dichlorodiphenyl sulfoxide using available raw materials and in high yield of the target product.

Изобретение позволяет осуществить получение 4,4'-дихлордифенилсульфоксида технологически простым способом с использованием доступных компонентов с достаточно высоким выходом (94%).The solution of this problem is achieved by the fact that 4,4'-dichlorodiphenyl sulfoxide is obtained by the interaction of diphenyl sulfide with sulfuryl chloride, and diphenyl sulfide is previously dissolved in carbon tetrachloride, and the reaction is carried out in the presence of AlCl ₃ at a temperature of 0 - +5 ^o C according to the following scheme:

The invention allows the production of 4,4'-dichlorodiphenyl sulfoxide in a technologically simple way using available components with a fairly high yield (94%).

 The method is simple in hardware design and can be used in industry.

 The following are specific examples of the invention.

 Example 1

To a suspension of 1.0 g (7.5 mmol) of anhydrous aluminum trichloride in a solution of 2.7 g (10 mmol) of diphenyl sulfide in 50 ml of carbon tetrachloride at 0 ^° C., 2 ml (25 mmol) of sulfuryl chloride are added.

The solvent was evaporated, the residue was dried and crystallized from chloroform. Yield of 4,4'-dichlorodiphenyl sulfoxide: 0.25 g (94%) _M.p. 143-144 ^o C.

 Example 2

Carried out analogously to example 1, but the reaction is carried out at 5 ^o C. Obtain 0.24 g (90%) of 4,4'-dichlorodiphenyl sulfoxide.

 Example 3

Carried out analogously to example 1, but the reaction is carried out at 2.5 ^o C. Obtain 0.24 g (90%) of 4,4'-dichlorodiphenyl sulfoxide.

 Carrying out the reaction at temperatures above this leads to side processes, which affects the quality of the resulting product and reduces its yield.

 Literature.

 1. F. Krafft. Ber., 7, 1874, p, 1164-65.

 2. Meers C.A., McCollum G.j., Tetrahedron Lett., 1973, 4, p. 289.

 3. G.M. Wong, T.-L. Ho, Synthesis, 1972, p. 561.

 4. RF patent N 2122538, priority July 22, 1996.

Claims (1)

The method of producing 4,4'-dichlorodiphenyl sulfoxide by the interaction of diphenyl sulfide with sulfuryl chloride, characterized in that diphenyl sulfide is pre-dissolved in carbon tetrachloride, and the reaction is carried out in the presence of AlCl ₃ at a temperature of 0 - +5 ^o C.