The method of producing sulfoxidov

IPC classes for russian patent The method of producing sulfoxidov (RU 2127258):

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 invention relates to methods for producing sulfoxidov that can be used as extractants metals, flotation agents and biologically active substances. The invention consists in the oxidation of sulfide with chlorine dioxide in an organic solvent at a volume ratio of sulfide : solvent = 1 : 1-20, and a molar ratio of sulfide : chlorine dioxide, equal to 1 : 0.5, and for two hours at a temperature of 18-20°C. the Method allows to obtain the sulfoxide with the release of 90% in the environment of dichloromethane.

The invention relates to a method of producing sulfoxidov that can be used as extractants metals, flotation reagents, solvents and biologically active substances.

Known oxidation of sulfides to sulfoxidov 30% hydrogen peroxide in acetic acid or acetone. While the reaction proceeds slowly (about two weeks), and the target product contains shared hard impurities sulfone (Karaulov E. N. Chemistry of sulfides oil. M.: Nauka, 1970).

A known method of producing sulfoxidov by oxidation of sulfides with hydrogen peroxide in acetic anhydride (prototype). Way don't fill the quantity of hydrogen peroxide to a solution of sulfide in acetic anhydride with stirring and the temperature from +20 to -10^oC. the Reaction mixture was left overnight. The resulting sulfoxide allocate or distillation of the acetic anhydride, or by extraction sulfoxide chloroform or dichloromethane. Output sulfoxide is 68-88%. A method of obtaining sulfoxide is long reaction occurring about a day (SU, 314752, 1971).

The present invention is to increase the efficiency of the method through the use of new oxidizer organic sulfur compounds, which allows to obtain the sulfoxide with the release of 80-90% and to reduce the reaction time of the oxidation of sulfide to two hours.

The essential features of the invention is the oxidation of sulfide with chlorine dioxide in an organic solvent by passing air with chlorine dioxide through a solution of the sulfide in a molar ratio of sulfide : chlorine dioxide, equal to 1 : 0.5 and a volume ratio of sulfide : solvent 1 : 1 to 5, or by adding a solution of chlorine dioxide in carbon tetrachloride to sulfide at a volume ratio of 20 : 1 and a molar ratio of sulfide : chlorine dioxide, equal to 1 : 0.5, and for two hours at a temperature of 18-20^oC.

The method is as follows.

Example Hladilnika and thermometer. Through a solution of 5 ml (4,2 g) dioctyladipate in 25 ml of dichloromethane bubbled air with chlorine dioxide (from 100 ml of an aqueous solution containing 4 g/l ClO₂). The reaction mixture was stirred on a magnetic stirrer for 2 hours at 20^oC. monitoring the progress of reactions and the absence of impurities sulfone checked by TLC and GLC. For thin-layer chromatography using Silufol plates, which are in iodine chamber. Eluent - ethanol : benzene (7 : 93). After the reaction the solvent is distilled off. The reaction product produce by recrystallization from ethanol. Yield 4.0 g (90%), white crystals.

So pl. 68 - 69^oC.

IR-spectrum (CCl₄, , cm^-1): 1050, 1380, 1440, 2880, 2950, 2980.

PMR-spectrum (CDCl₃, , M. D.): 0,85 t (6H, CH₃); 1,24 m (16H, CH⁴₂^,5,6,7); 1,41 m (4H, CH³₂); 1.73 m (4H, CH²₂); 2,61 m (4H, CH₂S).

NMR ¹³C range of dioctylsulfosuccinate (CDCl₃, , M. D.): 22 (2C, CH₃), 29 (12C, CH₂), 53 (2C, CH₂SO).

Example 2. Oxidation of dioctyladipate in the environment of carbon tetrachloride. The oxidation is carried out analogously to example 1, the volume ratio of the sulfide : carbon tetrachloride is 1 : 5, the molar ratio of sulfide : chlorine dioxide is 1 : 0.5, slania of dioctyladipate in the environment of carbon tetrachloride. The oxidation is carried out analogously to example 1, the volume ratio of the sulfide : carbon tetrachloride is 1 : 3, the molar ratio of sulfide : chlorine dioxide is 1 : 0.5, the reaction time is 2 hours, the temperature of the 18^oC. Output dioctylsulfosuccinate is 78%.

Example 4. Oxidation of dioctyladipate in the environment of carbon tetrachloride. The oxidation is carried out analogously to example 1, the volume ratio of the sulfide : tetrachloride hydrocarbon is 1 : 1, the molar ratio of sulfide : chlorine dioxide is 1 : 0.5, the reaction time is 2 hours, the temperature of the 18^oC. Output dioctylsulfosuccinate is 75%.

Example 5. Oxidation of dioctyladipate in the environment of chloroform. The oxidation is carried out analogously to example 1, the volume ratio of the sulfide : chloroform is 1 : 5, the molar ratio of sulfide : chlorine dioxide is 1 : 0.5, the reaction time is 2 hours, the temperature of the 20^oC. Output dioctylsulfosuccinate is 70%.

Example 6. Oxidation of dioctyladipate in the environment of ethyl alcohol. The oxidation is carried out analogously to example 1, the volume ratio of the sulfide : ethyl alcohol is 1 : 5, the molar ratio of sulfide : chlorine dioxide is 1 : 0.5, the reaction time is 2 hours, the temperature of the 20^oC. Output dioctylsulfosuccinate is 70%.lending ratio of sulfide : acetone is 1 : 5, the molar ratio of sulfide : chlorine dioxide is 1 : 0.5, the reaction time is 2 hours, the temperature of the 20^oC. Output dioctylsulfosuccinate is 60%.

Example 8. Oxidation of dioctyladipate in the environment of diethyl ether. The oxidation is carried out analogously to example 1, the volume ratio of the sulfide : diethyl ether 1 : 5, the molar ratio of sulfide : chlorine dioxide is 1 : 0.5, the reaction time is 2 hours, the temperature of the 20^oC. Output dioctylsulfosuccinate is 60%.

Example 9. To 200 ml of an aqueous solution of chlorine dioxide is added 200 ml of carbon tetrachloride. The mixture is stirred for 30 minutes and transferred into a separating funnel. The breaking time is 30 minutes. The lower layer containing chlorine dioxide in carbon tetrachloride is drained and used for oxidation of dioctyladipate. The reaction is performed in a three-neck flask, equipped with reflux condenser, dropping funnel and thermometer. To 10 ml (8,4 g) dioctyladipate added dropwise 200 ml of chlorine dioxide in carbon tetrachloride. The reaction mixture was stirred on a magnetic stirrer for 2 hours at a temperature of 20^oC. monitoring the progress of reactions and the absence of impurities sulfone checked by TLC and GLC. For thin-layer chromakey reaction the solvent is distilled off. The reaction product produce by recrystallization from ethanol. Yield 7.5 g (85%), white crystals. So pl. 68-69^oC.

In similar conditions with good outputs obtained dipropyl and dimethylsulfoxide.

Used books
1. Karaulova E. N. Chemistry of sulfides oil. -M.: Nauka, 1970.

2. Prilezhaeva E. N., Sviridov, A. C., Laba Century. And., Azimova, a Method of producing sulfoxidov. Auth. testimony N 314752, 1971.0

The method of producing sulfoxidov by oxidation of sulfides in the medium of organic solvent and selection of the target product by known methods, wherein the oxidation is carried out with chlorine dioxide in the environment of an organic solvent at a volume ratio of sulfide : solvent 1 : 1 - 20 and the molar ratio of sulfide : chlorine dioxide, equal to 1 : 0.5 V for two hours at a temperature of 18 - 20^oC.