The method of producing sulfoxidov

IPC classes for russian patent The method of producing sulfoxidov (RU 2139275):

C07C317/04 - of an acyclic saturated carbon skeleton

C07C315/02 - by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides

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(57) Abstract:

The sulfoxidov is produced by oxidation of the sulfide with an aqueous solution of chlorine dioxide at a molar ratio of sulfide : chlorine dioxide, equal to 1 : 0.5, and for 30-90 min at 20°C in an organic solvent. The method allows to obtain the sulfoxide with a yield of 90-95%.

The invention relates to a method of producing sulfoxidov, which are used as biologically active substances, extractants rare metals and selective solvents.

Known oxidation of sulfides to sulfoxidov 30% hydrogen peroxide in acetic acid or acetone. But the reaction is slow (about two weeks) [Karaulov E. N. Chemistry of sulfides oil. M., Nauka, 1970].

A known method of producing sulfoxidov oxidation of sulfides with hydrogen peroxide in acetic anhydride (prototype) [Prilezhaeva E. N., Sviridov, A. C., Laba Century. And., Azimova, a Method of producing sulfoxidov. Auth. testimony N 314752, 1971] . According to this method, the sulfoxidov synthesized as follows: to a solution of sulfide in acetic anhydride with stirring, added dropwise an equimolar amount of hydrogen peroxide (reaction temperature from +20 to -10^oC). Reacciona the th sulfoxide chloroform. Output sulfoxide is 68-88%. The disadvantage of this method is the duration of the reaction (about a day), relatively low output and the negative reaction temperature.

The present invention is to increase the efficiency of the method of obtaining sulfoxidov due to the application of the new oxidizer of organic sulfur compounds and the reaction of the oxidation of sulphides in an aqueous solution of chlorine dioxide at room temperature (20^oC), if necessary in the medium of organic solvent that can synthesize sulfoxide with the release of 88-95% and to reduce the reaction time up to 30-90 minutes

This is the technical result, which is in causal connection with the existing features of the invention.

The essential feature of the invention is to conduct the oxidation reaction of diallylsulfide aqueous solution of chlorine dioxide at a molar ratio of sulfide : chlorine dioxide, equal to 1 : 0.5, and accordingly, within 30-90 minutes at a temperature of 20^oC, if necessary in the medium of organic solvent.

To select the optimal reaction conditions for the oxidation varied the molar ratio of sulfide : diocles leads to incomplete conversion of sulfide and reduction of sulfoxide. The increase in the number of chlorine dioxide to the formation of sulfones along with sulfoxidov.

According to the proposed method the oxidation of diallylsulfide carried out as follows.

Example 1. Oxidation of dioctyladipate. To 0.85 grams (of 0.003 mole) of dioctyladipate added dropwise 22 ml of an aqueous solution of chlorine dioxide (concentration of ClO₂is 5 g/l). The molar ratio of sulfide: chlorine dioxide is 1 : 0.5 in. The reaction is carried out for 90 min at 20^oC. Control reactions carried out TLC and GLC. For TLC using Silufol plates that show a 5% solution of KMnO₄with the addition of a few drops of concentrated H₂SO₄Eluent - ethanol : benzene (1 : 4). After the reaction the precipitated crystals of the oxidized product is filtered, washed with water and dried in vacuum. Get 0,81 g (90%) of dioctylsulfosuccinate in the form of white crystals, so pl. 68-69^oC (from EtOH). IR-spectrum (CCl₄), /cm^-1: 1050 (S=O). An NMR spectrum¹H (CDCl₃, , M. D.): 0.85 (t, 6H, CH₃); 1.24 (m, 16H, CH₂^4,5,6,7), 1.41 (m, 4H, CH₂³), 1.73 (m, 4H, CH₂²); 2.61 (m, 4H, CH₂-S). An NMR spectrum¹³C (CDCl₃, , M. D. ): 22 (2C, CH₃), 29 (12C, CH₂), 53 (2C, CH₂SO).

Example 2. About the ora. The molar ratio Diisobutylene : chlorine dioxide is 1 : 0.5 in. The reaction is carried out for 30 min at 20^oC. Then the reaction mixture is extracted with chloroform. The chloroform is distilled off and get 0,90 g (98%) of the oxidized product. According to GC with known compounds oxidized product consists of 95% of diisobutylaluminum and 3% of diisobutylamine. Cleaning of diisobutylamine carried out by vacuum distillation. IR-spectrum (CCl₄), /cm^-1: 1050 (S=O).

Example 3. Oxidation of Dobropillya. To 0.84 g (to 0.007 mole) of Dobropillya added dropwise 48 ml of an aqueous solution of chlorine dioxide (concentration of ClO₂5 g/l), the molar ratio dipropylacetic : chlorine dioxide is 1 : 0.5 in. Next, perform a reaction and produce oxidized products as in example 2. Get 0,92 g (97%) with a mixture of 95% dipropylacetamide and 2% of dipropylamine. Cleaning dipropylacetamide carried out by vacuum distillation. IR-spectrum (CCl₄), /cm^-1: 1050 (S=O).

Thus, the optimal conditions for obtaining sulfoxidov are: oxidation of sulfides aqueous solution of chlorine dioxide at a molar ratio of sulfide : chlorine dioxide, equal to 1 : 0.5, and accordingly, in techen g (to 0.007 mole) of Dobropillya dissolved in 5 ml dichloromethane and added dropwise 48 ml of an aqueous solution of chlorine dioxide (concentration of ClO₂5 g/l), the molar ratio dipropylacetic : chlorine dioxide is 1 : 0.5 in. Next, perform a reaction similar to example 3. Get 0,86 g (91%) with a mixture of 88% of dipropylacetamide and 3% of dipropylamine. Cleaning of dipropylamine carried out by vacuum distillation. IR-spectrum (CCl₄), /cm^-1: 1050 (S=O).

Example 5. Oxidation of Dobropillya in the environment of ethyl acetate. 0.84 g (to 0.007 mole) of Dobropillya dissolved in 5 ml of ethyl acetate and added dropwise 48 ml of an aqueous solution of chlorine dioxide (concentration of ClO₂5 g/l), the molar ratio dipropylacetic: chlorine dioxide is 1:0.5 in. Next carry out the reaction as in example 4. Obtain 0.87 g (94%) with a mixture of 92% of dipropylacetamide and 2% of dipropylamine. Cleaning of dipropylamine carried out by vacuum distillation. IR-spectrum (CCl₄), /cm^-1: 1050 (S=O).

The method of producing sulfoxidov by oxidation of sulfides with subsequent isolation of the target product by known methods, wherein the oxidation is conducted with an aqueous solution of chlorine dioxide at a molar ratio of sulfide : chlorine dioxide equal to 1 : 0,5, respectively, within 30 - 90 minutes at a temperature of 20^oC, if necessary in the environment of organic races