Clean synthesis method for di-tert-butyl disulfide

A technology of di-tert-butyl disulfide and synthesis method, which is applied in the preparation of hydrogenated polysulfide/polysulfide, organic chemistry, etc., can solve the problems of high cost, difficult recovery of catalyst, high toxicity of solvent, etc., and achieve the reaction time Short, recycled reusable, inexpensive effect

A technology of di-tert-butyl disulfide and synthesis method, which is applied in the preparation of hydrogenated polysulfide/polysulfide, organic chemistry, etc., can solve the problems of high cost, difficult recovery of catalyst, high toxicity of solvent, etc., and achieve the reaction time Short, recycled reusable, inexpensive effect

CN101838228BInactive Publication Date: 2012-11-21ZHENGZHOU UNIV
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  • Clean synthesis method for di-tert-butyl disulfide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add 2.18mmol of catalyst CuCl, 100mL of acetone, 867mmol of tert-butyl mercaptan (t-Bu-SH) into the reaction vessel, and add 54g of 30% (mass fraction of hydrogen peroxide in hydrogen peroxide, the same below) hydrogen peroxide under stirring condition (476.5mmol) and 150mL acetone mixture, [n(CuCl):n(t-Bu-SH):n(H2 o 2 )=2.5: 1000: 550 (representing the molar ratio of each substance, the same below), the volume ratio of the total volume added by the solvent acetone to tert-butyl mercaptan is 2.5: 1], and the control reaction temperature is between 40 ± 5 ° C , react until the detected mercaptan conversion rate reaches 99.8%, stop the reaction. The catalyst was removed by filtration, and then the acetone was removed. After standing for stratification, the oil layer was obtained as di-tert-butyl disulfide, with a selectivity of 94.5%. Mass Spectrum See figure 1 , molecular ion peak 178, base peak 57.

Embodiment 2

[0020] In reaction vessel, add catalyst CuCl 0.0434mmol, acetone 20mL, add tert-butyl mercaptan 86.7mmol, add the mixed solution of 50% hydrogen peroxide 3.5g (51.5mmol) and 10mL acetone under stirring condition, [n(CuCl):n (t-Bu-SH):n(H 2 o 2 )=0.50: 1000: 594, the volume ratio of the total volume added by the solvent acetone to tert-butyl mercaptan is 3.0: 1], the reaction temperature is controlled at 35 ± 5°C, and the reaction until the detected mercaptan conversion rate reaches 99.6%, Stop responding. The catalyst was removed by filtration, and then the acetone was removed. After standing for stratification, the oil layer was obtained as di-tert-butyl disulfide, with a selectivity of 93.8%. Mass Spectrum See figure 1 .

Embodiment 3

[0022] In the reaction vessel, add catalyst CuCl 0.0606mmol, acetone 20mL, add tert-butyl mercaptan 86.7mmol, add the mixed solution of 75% hydrogen peroxide 2.2g (48.5mmol) and 10mL acetone under stirring condition, [n(CuCl):n (t-Bu-SH):n(H 2 o 2 ) = 0.699: 1000: 560, the volume ratio of the total volume added by the solvent acetone to tert-butyl mercaptan is 3.0: 1], the reaction temperature is controlled at 40 ± 3°C, and the reaction until the detected mercaptan conversion rate reaches 98.4%, That is, the reaction stops. The catalyst was removed by filtration, and then the acetone was removed. After standing for stratification, the oil layer was obtained as di-tert-butyl disulfide, with a selectivity of 93.7%. Mass Spectrum See figure 1 .

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Abstract

The invention belongs to the field of organic synthesis and particularly relates to a clean synthesis method for di-tert-butyl disulfide, which comprises the following steps: adding tert-butyl mercaptan, a catalyst and a solvent, i.e. acetone, into a reactor container, or only adding the tert-butyl mercaptan and the catalyst into the reactor container firstly and then adding an oxidizer, i.e. oxyful, or a mixture of acetone and oxyful into the reactor container with stirring; controlling a reaction temperature between minus 20 DEG C and 70 DEG C to perform a reaction sufficiently; after the reaction is completed, post-processing the obtained product to obtain the di-tert-butyl disulfide, wherein the catalyst is cuprous chloride, copper chloride or a mixture of the cuprous chloride and thecopper chloride in random mass proportion. The invention meets the requirement for clean production. The catalyst and the reaction solvent have low price, can be conveniently recycled, have small usage in the reaction and have excellent catalytic performance. Meanwhile, the process has short reaction time, the conversion rate of the tert-butyl mercaptan reaches 98 to 100 percent, the selectivity of the di-tert-butyl disulfide is between 90 and 96 percent, the reaction yield is high and the clean synthesis method is suitable for industrial production.

Description

(1) Technical field [0001] The invention belongs to the field of organic synthesis, in particular to a clean synthesis method of di-tert-butyl disulfide. (2) Background technology [0002] Disulfides have important application value in the fields of food science, biochemistry and fragrance chemistry. First of all, in industry, organic disulfides have been used as vulcanizing agents in natural rubber, synthetic rubber and elastomers to give them good tensile strength; in addition, organic disulfide extreme pressure additives are an important class of lubricating oil additives. High load resistance, low corrosion, excellent high temperature extreme pressure performance, widely used in extreme pressure and anti-wear lubricating oil, metal processing extreme pressure lubrication and other fields. From the viewpoint of synthesis and biochemistry, organic disulfides are important intermediates for the synthesis of sulfinyl compounds and oxysulfur compounds. [0003] The English ...

Claims

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Application Information

Patent Timeline
21 Nov 2012
Publication
CN101838228B
IPC
C07C321/14; C07C319/24
Inventors
章亚东; 黄俊芳