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Synthesis method of stable isotope labeled 3-chloro-1,2-propylene glycol fatty acid diester

A technology of propylene glycol fatty acid and stable isotope, which is applied in the direction of isotope introduction into organic compounds, acyclic/carbocyclic compound isotope introduction, organic chemical methods, etc., which can solve the problems of high cost and difficult production process

Active Publication Date: 2021-06-04
上海安谱璀世标准技术服务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method is used for the quantitative detection of chloropropanol ester, and stable isotope internal standard needs to be used, and because stable isotope labeling raw material price is more expensive, and cost is higher, and production technology is more difficult to realize, how to guarantee the stable isotope atom in the production process is not It will fall off, and it is very technically difficult to ensure product purification. The synthesis method of stable isotope-labeled 3-chloro-1,2-propanediol fatty acid diester has not been reported in the literature

Method used

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preparation example Construction

[0019] A kind of synthetic method of the 3-chloro-1,2-propanediol fatty acid diester of stable isotope label provided by the invention comprises the following steps:

[0020] S1: Add stable isotope-labeled epichlorohydrin and water in sequence in the reaction vessel, react at a temperature of 90-110°C for 20-30 hours, and distill off the water under reduced pressure to obtain stable isotope-labeled 3-chloro-1,2- Propylene glycol; the molar ratio of the stable isotope-labeled epichlorohydrin to water is 1:2 to 1:4, which saves the amount of water while ensuring the complete hydrolysis reaction and reduces the post-reaction treatment time;

[0021] S2: reacting stable isotope-labeled 3-chloro-1,2-propanediol and fatty acid chloride under the catalysis of immobilized lipase to prepare 3-chloro-1,2-propanediol fatty acid diester; the stable isotope labeling The molar ratio of 3-chloro-1,2-propanediol and fatty acid chloride is 1:2.0~1:3.0, this ratio range can ensure the complete ...

Embodiment 1

[0023] Add epichlorohydrin-D to the reaction vessel 5 (10mmol, 975mg), water (30mmol, 6mL), reacted at 100°C for 24 hours, and distilled off the water under reduced pressure to obtain 3-chloro-1,2-propanediol-D 5 .

Embodiment 2

[0025] Add 3-chloro-1,2-propanediol-D to the reaction vessel 5 (9.0mmol, 1.0g), palmitoyl chloride (25mmol, 6.9g), Novozym435 immobilized lipase (300mg), reacted for 2.5 hours at a temperature of 25 to 30°C, filtered to remove the immobilized lipase, washed the filter cake with n-hexane, and the filtrate Column chromatography after concentration gives 3-chloro-1,2-propanediol palmitic acid diester-D 5 , yield 60%.

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Abstract

The invention discloses a synthesis method of stable isotope labeled 3-chloro-1,2-propylene glycol fatty acid diester. The synthesis method comprises the following steps: S1, hydrolyzing stable isotope labeled epoxy chloropropane to prepare stable isotope labeled 3-chloro-1,2-propylene glycol; and S2, carrying out a reaction on the stable isotope labeled 3-chloro-1,2-propylene glycol and fatty acid acyl chloride under the catalytic action of the immobilized lipase to prepare the 3-chloro-1,2-propylene glycol fatty acid diester. The synthesis process has characteristics of mild conditions, simple process, short process route, easy product separation and purification and high yield, the chemical purity and the stable isotope abundance of the obtained product achieve more than 99% so as to meet the requirements of the standard reagent for quantitative detection of 3-chloro-1,2-propylene glycol fatty acid diester; and the use value is high, and the economical efficiency is good.

Description

technical field [0001] The invention relates to a method for synthesizing stable isotope-labeled 3-chloro-1,2-propanediol fatty acid diester, which belongs to the technical field of fine chemical synthesis. Background technique [0002] 3-Chloro-1,2-propanediol fatty acid diester is a kind of chloropropanol ester, which is a new class of carcinogens found in food, especially in refined vegetable oil. Chlorpropanol ester releases free chloropropanol through the action of intestinal pancreatic lipase, which has reproductive toxicity and neurotoxicity, and can cause kidney tumors; therefore, more and more attention is paid to chloropropanol ester at home and abroad. Quantitative detection of trace amounts of chloropropanol esters in food is becoming more and more important. [0003] Stable isotope dilution mass spectrometry IDMS (Isotope Dilution Mass Spectrometry) is a newly developed benchmark quantitative method for measuring trace and trace organic compounds. The method i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/62C12P7/64C07B59/00C07C29/10C07C31/34C07C31/38C07C69/28C07C69/58C07C69/63
CPCC12P7/62C12P7/6436C07B59/001C07C29/106C07C69/28C07C69/58C07C69/63C07B2200/05C07C31/34C07C31/38
Inventor 郭会陈武炼
Owner 上海安谱璀世标准技术服务有限公司
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