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
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[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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