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Selective synthesis method of sn-1 chloropropanol fatty acid ester

A fatty acid ester, sn-1 technology, applied in the field of selective synthesis of sn-1 chloropropanol fatty acid ester, can solve the problems of difficult removal of catalysts, limited types, high price, etc., and achieves easy acquisition, less use, low cost effect

Inactive Publication Date: 2014-12-24
WUHAN POLYTECHNIC UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, a small number of foreign manufacturers have provided this product, but the sample size is very small, the types are limited and the price is extremely expensive; due to the variety of fatty acids in 3-MCPD esters, and there are different types such as monoesters and diesters, relevant research is facing challenges. Many practical difficulties, so it is of great significance to explore and develop economical and convenient 3-MCPD ester synthesis methods
BUKOWSKI W etc. once used diethylene glycol dimethyl ether as solvent, and used low carbonic acid to synthesize chloropropanol fatty acid ester by ring-opening epichlorohydrin under the catalysis of chromium acetate. This method has good selectivity and Yield, but the catalyst is difficult to remove during the subsequent processing of the product

Method used

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  • Selective synthesis method of sn-1 chloropropanol fatty acid ester
  • Selective synthesis method of sn-1 chloropropanol fatty acid ester

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Effect test

Embodiment 1

[0022] Add 10g molecular sieve (SiO 2 :Al 2 o 3 =50:1), magnetically stirred for 5 hours in a water bath at 70°C, suction filtered while hot, and vacuum-dried at 120°C for 2 hours to prepare the ferric sulfate catalyst supported by aluminosilicate molecular sieves. Then take by weighing 0.05mol of lauric acid and place it in a 100mL round-bottomed flask, preheat and melt in a water bath of 60° C. 5% of the total weight of epichlorohydrin) was stirred and mixed, and then 0.05mol of epichlorohydrin was added dropwise. After 24 hours, the reaction was stopped, the product was filtered with suction to remove the catalyst, washed with methanol, and the solvent was evaporated to obtain sn-1 chloropropanol monolaurate.

Embodiment 2

[0024] In 0.2mol / L ferric chloride aqueous solution (50mL), add 10g molecular sieve (SiO 2 :Al 2 o 3 =80:1), stirred magnetically for 4 hours in a water bath at 80°C, filtered while hot, and dried at 120°C for 2 hours to prepare a molecular sieve-supported ferric chloride catalyst. Then weigh 0.05mol of n-decanoic acid and place it in a 100mL round-bottomed flask, preheat and melt it in a water bath at 50° C. 2% of the total weight of capric acid and epichlorohydrin) was stirred and mixed, and then 0.025mol of epichlorohydrin was added dropwise. After 40 hours, the reaction was stopped, the product was filtered with suction to remove the catalyst, washed with methanol, and the solvent was evaporated to obtain sn-1 chloropropanol n-decanoic acid monoester.

Embodiment 3

[0026] In 0.2mol / L ferric nitrate aqueous solution (50mL), add 10g molecular sieve (SiO 2 :Al 2 o 3 =38:1), magnetically stirred for 4 hours in a water bath at 90°C, suction filtered while hot, and dried at 120°C for 2 hours to prepare a molecular sieve-supported ferric nitrate catalyst. Then take by weighing the n-octanoic acid of 0.05mol and place in the 100mL round-bottomed flask, preheat and melt in the water bath pan of 50 ℃ and the ferric nitrate catalyst (being that catalyst amount is reactant n-octanoic acid and 3% of the total weight of epichlorohydrin) was stirred and mixed, and then 0.10mol of epichlorohydrin was added dropwise. The reaction was stopped after 60 hours, the product was filtered with suction to remove the catalyst, washed with methanol, and the solvent was evaporated to obtain sn-1 chloropropanol n-octanoic acid monoester.

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Abstract

The invention discloses a selective synthesis method of sn-1 chloropropanol fatty acid ester, which comprises the following steps: 1) adding an aluminosilicate molecular sieve into an iron salt solution, heating and stirring to react sufficiently, carrying out vacuum filtration while the solution is hot, and carrying out vacuum drying on the filtered substance to obtain the aluminosilicate molecular sieve-supported iron salt catalyst; and 2) preheating and melting fatty acid, evenly mixing with the aluminosilicate molecular sieve-supported iron salt catalyst, dropwisely and slowly adding epoxy chloropropane, reacting at 50-90 DEG C for 24-80 hours, carrying out vacuum filtration to remove the catalyst, washing with methanol, and concentrating the filtrate to obtain the product. The method has the advantages of abundant raw material sources, high product selectivity, simple preparation and after-treatment, low cost, low environmental pollution and the like.

Description

technical field [0001] The invention belongs to the technical field of food safety, and in particular relates to a selective synthesis method of sn-1 chloropropanol fatty acid ester (that is, an esterification product of 1-hydroxyl in chloropropanol). Background technique [0002] Chloropropanol is a general term for a class of compounds formed after the hydroxyl group in glycerol is replaced by chlorine, and chloropropanol ester is the esterification product of chloropropanol and fatty acid. Chloropropanol and its fatty acid esters are a class of pollutants produced during the processing and manufacturing of some specific foods. Relevant toxicity research reports indicate that chloropropanols have reproductive toxicity, neurotoxicity, and carcinogenicity. In early studies of 3-monochloropropanol-l,2-diol (3-MCPD) in acid hydrolyzed vegetable proteins, it has been found that there is a large amount of 3-MCPD mono- and di-ester formation . Chloropropanol esters are conside...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/26C07C69/28C07C69/58
CPCC07C67/26C07C69/63C07C69/65
Inventor 胡志雄王维曼张维农齐玉堂
Owner WUHAN POLYTECHNIC UNIVERSITY
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