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Method of producing beta-mercaptocarboxylic acids

A technology of mercaptocarboxylic acid and compound, which is applied in the field of preparation of β-mercaptocarboxylic acid compounds, can solve the problems of cheap preparation process, low productivity, long reaction time, etc., and achieve the effects of simplified purification process, high productivity and high yield

Inactive Publication Date: 2010-08-11
RESONAC HOLDINGS CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reaction described in Acta Chimica Scandinavica 1951, 5, 690-698 using diethylamine in large excess, involves problems of low productivity due to long reaction time and reaction process requiring equipment and cheap The preparation process
No literature describes or suggests the use of water-compatible solvents, polar solvents, or the effects of using such solvents

Method used

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  • Method of producing beta-mercaptocarboxylic acids
  • Method of producing beta-mercaptocarboxylic acids

Examples

Experimental program
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Effect test

Embodiment 1

[0125] N-Methylpyrrolidone (NMP) (313 g, produced by Junsei Chemical Co., Ltd.) was charged in a 500 ml volume autoclave made of HASTELLOY C (registered trademark), and crotonic acid (25.5 g, 0.3 mol, Tokyo Chemical Industry Co., Ltd.) and 4A molecular sieve (MS4A) (24 g, powder, produced by Junsei Chemical Co., Ltd.) as a solid acid catalyst. Hydrogen sulfide (16.1 g, 0.5 mol, 1.6 equivalents based on crotonic acid, manufactured by Sumitomo Seika Chemicals Co., Ltd.) was absorbed into the mixture while maintaining the temperature in the range of 2 to 7°C. The temperature was then raised to 100°C and held at this temperature for 5 hours. The autoclave was cooled to 25°C and the solution therein was sampled. The sample was analyzed by HPLC, and it was confirmed that the generated reaction product was 3-mercaptobutyric acid (25.6 g, 0.2 mol, yield: 72%). The conversion of crotonic acid was 100%. The reaction pressure at the beginning of the reaction was 0.6Mpa, and the reacti...

Embodiment 2-11

[0127] The reaction is carried out in the same manner as in Example 1, except that, as shown in Table 1, the solvent used is N-methyl-2-pyrrolidone (NMP), dimethylformamide (DMF), 1,3-bis Methyl-2-imidazolidinone (DMI), tetrahydrofuran (THF), methanol, ethanol or isopropanol (IPA), and 4A molecular sieves as solid acid catalysts vary in shape and amount of hydrogen sulfide. The results are shown in Table 1.

[0128] Table 1

[0129]

Embodiment 12

[0131] The reaction was carried out in the same manner as in Example 1, except that Y-54 molecular sieves (24 g, powder, produced by Union Showa K.K.) were used, and a solvent of NMP (266 g, produced by Junsei Chemical Co., Ltd.) and distilled water (47 g) was used. The mixture was used as solvent, and the reaction temperature was 115°C. It was confirmed that the generated reaction product was 3-mercaptobutyric acid (27.0 g, 0.2 mol, yield: 76%). The conversion rate of crotonic acid was 100%. The reaction pressure at the beginning of the reaction is 0.5Mpa, and the reaction pressure at the end of the reaction is 0.4Mpa.

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Abstract

The invention relates to a method for efficiently producing beta-mercaptocarboxylic acids using a solid acid catalyst such as zeolite, which product corresponds to respective starting materials selected from alpha, beta-unsaturated carboxylic acids (alpha, beta-unsaturated carboxylic acid, alpha, beta-unsaturated carboxylic acid ester, alpha, beta-unsaturated amide, alpha, beta-unsaturated aldehide and alpha, beta-unsaturated ketone) and hydrogen sulfides (hydrogen sulfide, sulfide salt and hydrosulfide salt), wherein a solvent compatible with water is used in the reaction. According to the invention, beta-mercaptocarboxylic acids which are useful as additives in synthetic materials for pharmaceutical or agricultural agents and in polymer compounds can be industrially produced efficiently by using easily available alpha, beta-unsaturated carboxylic acid (such as crotonic acid) at high yield.

Description

technical field [0001] The present invention relates to a process for the efficient preparation of beta-mercaptocarboxylic acids, beta-mercaptocarboxylates, beta-mercapto Amides, β-mercaptoaldehydes and β-mercaptoketones (hereinafter, these compounds are collectively referred to as β-mercaptocarboxylic acid compounds), the starting materials correspond to the corresponding target products and are selected from α, β-not α, β-unsaturated carboxylic acid group consisting of saturated carboxylic acid, α, β-unsaturated carboxylic acid ester, α, β-unsaturated amide, α, β-unsaturated aldehyde and α, β-unsaturated ketone. Background technique [0002] Traditionally, mercapto compounds have been widely used as synthetic materials for various pharmaceuticals and agrochemicals. Specifically, the effectiveness of β-mercaptocarbonyl compounds as antioxidants has been highly recognized, and the compounds are industrially used as stabilizers for polymer compounds (Japanese Patent Applicat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/04C07C323/56C07C323/54C07C323/61C07B45/06
CPCC07B45/06C07C319/04C07C2101/16C07C2101/10C07C2601/10C07C2601/16C07C323/52C07C323/56C07C319/26
Inventor 涩谷彰青木英雅
Owner RESONAC HOLDINGS CORPORATION
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