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Method for preparing symmetrical disulfide compound

A compound and disulfide technology, applied in chemical instruments and methods, formation/introduction of mercapto/thioether groups, organic compound/hydride/coordination complex catalysts, etc., can solve problems such as difficult preparation of catalysts, and achieve Cheap and easy to prepare dosage, high yield and low impurity content

Inactive Publication Date: 2010-12-29
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The key catalyst of the method reported in Document 1 is difficult to prepare; the method reported in Document 2 involves reagents sensitive to water and air, which must be carried out in special containers.
This makes these methods subject to many limitations in practical applications

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0035] Catalyst preparation:

[0036] A. Preparation of N,N'-disalicylidene diamine cobalt:

[0037] Preparation of Schiff base I:

[0038] Weigh 48.8 g (0.4 mol) of salicylaldehyde, dissolve it in 240 ml of industrial alcohol and add it to a four-neck flask; weigh 12.0 g (0.2 mol) of ethylenediamine, add it dropwise to the reaction bottle, start stirring at the same time, and react at room temperature After 1 h, filter with suction, wash the filter cake with 200 ml of industrial alcohol, and dry to obtain a light yellow solid (52.0 g), with a yield of 96%.

[0039] Catalyst CoSalon (I, R 1 =H) Preparation:

[0040] Take 30.0 g (0.112 mol) of the above-prepared Schiff base I and mix 26.7 g (0.107 mol) cobalt acetate tetrahydrate into a four-neck flask, add 225 ml of industrial alcohol into the reaction flask, start stirring, and react at room temperature for 2 h; then heated to a temperature of 60~70°C, refluxed for 1 h; cooled to 20°C, filtered with suction, and washed wi...

Embodiment 1

[0056] Example 1 The substrate is 2-mercaptobenzothiazole, the catalyst is N,N'-disalicylidenediamine cobalt, and the organic solvent is absolute ethanol. The molar ratio of the feed material is substrate:catalyst 1:0.025, and the feed mass volume ratio substrate (g):solvent volume (ml) is 1:10.

[0057] Mix 50.1 g (0.3 mol) of 2-mercaptobenzothiazole and 2.44 g (0.0075 mol) of catalyst (I) into a 1000 ml three-necked flask equipped with a thermometer and mechanical stirring, then add 500 ml of absolute ethanol, and open Stir, ventilate, heat to 60°C, keep warm for reaction, TLC tracking detection, and the reaction ends in 1 hour. Cool naturally to 20°C, evaporate the solvent, and obtain 45.7 g of light yellow solid after recrystallization with 50 ml of toluene, yield 91.8%, purity 99.1%, m.p.178~179°C; 1 H NMR (500 MHz, CDCl 3 ):δ8.01 (d, J =8.0 Hz, 2H), 7.85 (d, J =8.0 Hz, 2H), 7.54 (d, J =7.5 Hz, 2H), 7.43 (d, J =7.0 Hz, 2H). IR (KBr): 2922, 669, 443 cm -1 . MS ( E...

Embodiment 2

[0059] The substrate was changed to 33.0 g (0.3 mol) of thiophenol, the amount of catalyst was 2.44 g (0.0075 mol), and the mass volume ratio of substrate (g): solvent volume (ml) was 1:10. Other conditions and preparation steps were the same Example 1. 29.5 g of milky white solid was obtained, with a yield of 90%, a purity of 99.2%, and an m.p of 60~61°C. 1 H NMR (500 MHz, CDCl 3 ): δ7.50 (d, J =8.5 Hz, 4H), 7.31 (t, J =7.5 Hz, 4H), 7.25 (t, J =7.0 Hz, 2H). IR (KBr): 3070, 685, 461 cm -1 . MS ( EI, 70 eV ): m / z=218 (100, M + ).

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Abstract

The invention discloses a method for preparing a symmetrical disulfide compound. In the method, a compound shown as a formula (III) is taken as a raw material, and a CoSalen complex shown as a formula (I) or (II) is taken as a catalyst; and the method comprises the following steps of: in an organic solvent, introducing air or oxygen serving as an oxidant, reacting at the temperature of between 20 and 100 DEG C, tracking and monitoring until the reaction is completed, and after the reaction is finished, performing after treatment on reacting fluid to prepare the symmetrical disulfide compound shown as a formula (IV). Compared with the prior art, the method for preparing the symmetrical disulfide compound has the advantages of simple and convenient operation, mild reaction condition, low cost, easy preparation and small dosage of the adopted catalyst, low cost, easy acquirement and cleanness of the adopted oxidant gas, low content of the impurity of disulfide as the finished product, higher yield, commercial prospect and remarkable application value and social and economic benefits.

Description

technical field [0001] The invention relates to a new method for preparing corresponding symmetrical disulfide compounds by catalytically oxidizing mercaptan or thiophenol compounds. Symmetrical disulfide compounds are an important class of intermediates for medicines, pesticides, dyes and polymer materials. Background technique [0002] Disulfides, also known as disulfide compounds, are mainly produced by oxidation of corresponding mercapto compounds. Prior to the present invention, the preparation methods of symmetrical disulfides were mainly reported in the following documents. (1) Hamid Golchoubian et al reported the use of Mn (III) Schiff base complexes as catalysts and air as oxidants to catalyze the oxidation of mercaptans or thiophenols to prepare symmetrical disulfides with a yield of 86-98% (Catalysis Communications. 2007, 8, 697-700); (2) Wang Hua et al. described the preparation of disulfides by catalytic oxidation of mercaptans with metal alkyl compounds and c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B45/06B01J31/22C07C319/24C07C321/28C07C323/09C07C323/33C07C323/20C07C323/62C07C321/10C07C321/04C07D277/78C07D307/38
Inventor 李永曙谭成侠潘丽艳颜贻意
Owner ZHEJIANG UNIV OF TECH
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