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Method for oxidizing sulfilimine into sulfoximide

A technology of sulfimide and sulfonimine, which is applied in the field of sulfimide oxidation to sulfonimine, can solve the problems of unfavorable product purification, easy environmental pollution, oxidizing agent does not meet atomic economy, etc., and achieves important environmental and social significance, The effect of simple reaction conditions and important industrial application value

Inactive Publication Date: 2016-04-13
NANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are many oxidizing agents that can oxidize sulfimine to sulfoximine, such as potassium permanganate, sodium perchlorate, ruthenium trichloride / periodic acid, calcium hypochlorite, etc. (US Patent, US2008094634A1), but these oxidizing agents are all It can only be realized under alkaline or acidic conditions, which requires an excessive amount of alkaline reagents or acid reagents, and some oxidants also need noble metal catalysis to react.
As a result, all the above oxidants do not meet the requirements of atom economy, and have disadvantages such as complicated operation, many by-products, unfavorable product purification, easy pollution of the environment, and high cost.

Method used

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  • Method for oxidizing sulfilimine into sulfoximide
  • Method for oxidizing sulfilimine into sulfoximide
  • Method for oxidizing sulfilimine into sulfoximide

Examples

Experimental program
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Effect test

Embodiment 1

[0023] (1) Dissolve 1 mmol of sodium tungstate dihydrate in 15 ml of water, stir for 5 minutes, and make a uniform and transparent solution;

[0024] (2) Add 6 milliliters of ethanol to the above solution, stir for 5 minutes;

[0025] (3) Add 15 milliliters of sulfuric acid in above-mentioned solution, stir 5 minutes;

[0026] (4) Add 0.1 gram of polyethylene glycol 10000 to the above solution and stir for 5 minutes;

[0027] (5) Transfer the above mixture into a 100 ml round bottom flask, stir at 120°C for 3 hours, and cool to room temperature;

[0028] (6) Pour the above-mentioned cooled reaction mixture into 500 ml of distilled water, collect the precipitate, wash it with deionized water and absolute ethanol in turn, and dry it in vacuum to obtain the tungsten oxide WO with oxygen holes. 3-x Nanosheets.

Embodiment 2

[0030] (1) Dissolve 2 mmol of sodium tungstate dihydrate in 20 ml of water, stir for 10 minutes, and make a uniform and transparent solution;

[0031] (2) Add 10 milliliters of ethanol to the above solution, stir for 10 minutes;

[0032] (3) Add 20 milliliters of sulfuric acid in above-mentioned solution, stir 10 minutes;

[0033] (4) Add 0.3 grams of polyethylene glycol 10000 to the above solution, and stir for 10 minutes;

[0034] (5) Transfer the above mixture into a 100 ml round bottom flask, stir at 160°C for 4 hours, and cool to room temperature;

[0035] (6) Pour the above-mentioned cooled reaction mixture into 500 ml of distilled water, collect the precipitate, wash it with deionized water and absolute ethanol in turn, and dry it in vacuum to obtain the tungsten oxide WO with oxygen holes. 3-x Nanosheets.

Embodiment 3

[0037] (1) Dissolve 3 millimoles of sodium tungstate dihydrate in 25 milliliters of water, stir for 20 minutes, and make a uniform and transparent solution;

[0038] (2) Add 13 milliliters of ethanol to the above solution, and stir for 20 minutes;

[0039] (3) Add 25 milliliters of sulfuric acid in above-mentioned solution, stir 20 minutes;

[0040] (4) Add 0.6 grams of polyethylene glycol 10000 to the above solution, and stir for 20 minutes;

[0041] (5) Transfer the above mixture into a 100 ml round bottom flask, stir at 200°C for 5 hours, and cool to room temperature;

[0042] (6) Pour the above-mentioned cooled reaction mixture into 500 ml of distilled water, collect the precipitate, wash it with deionized water and absolute ethanol in turn, and dry it in vacuum to obtain the tungsten oxide WO with oxygen holes. 3-x Nanosheets.

[0043] The preparation embodiment of sulfoximine is as follows:

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Abstract

The invention provides a method for oxidizing sulfilimine into sulfoximide. The method comprises the following steps: preparing a tungsten oxide WO3-x nanosheet catalyst, and carrying out WO3-x nanosheet catalyzed oxidation of sulfilimine. The method has the advantages of simple reaction conditions, no pollution in the whole reaction steps, low cost, important industrial application values, and important environmental and social significance.

Description

technical field [0001] The invention relates to organic chemistry, in particular to a method for oxidizing sulfimine into sulfoximine. Background technique [0002] Sulfoximine is a class of organic compounds with important biological activities, especially N-cyanosulfoximine compounds. The new insecticide Sulfoxaflor developed by Dow AgroSciences is one of these substances. Contact representatives of (Babcock, J.M.; Gerwick, C.B.; Huang, J.X.; Loso, M.R.; Nakamura, G.; Nolting, S.P.; Rogers, R.B.; Sparks, T.C.; Thomas, J.; Watsona, G.B.; and Zhua, Y. PestManag. Sci. 2011, 67, 328.). Sulfoximine is usually prepared by oxidation of sulfimine, for example, sulfoxaflor can be obtained by oxidation of corresponding N-cyanosulfimine with m-chloroperoxybenzoic acid under alkaline conditions (PCT patent, WO2007149134A1). There are many oxidizing agents that can oxidize sulfimine to sulfoximine, such as potassium permanganate, sodium perchlorate, ruthenium trichloride / periodic aci...

Claims

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Application Information

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IPC IPC(8): C07C381/10C07D213/34B01J23/30
CPCB01J23/30C07C381/10C07D213/34
Inventor 鲍克燕毛武涛赵强张正辉左军超谢海泉李贝贝
Owner NANYANG NORMAL UNIV
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