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CN-122012182-A - Method for synthesizing branched fatty acid ester of hydroxy fatty acid by taking natural oil containing hydroxy fatty acid as raw material

CN122012182ACN 122012182 ACN122012182 ACN 122012182ACN-122012182-A

Abstract

The invention discloses a method for synthesizing hydroxy fatty acid branched fatty acid ester by taking natural grease containing hydroxy fatty acid as a raw material, which comprises the steps of taking natural hydroxy fatty acid grease and fatty acid acyl chloride as core raw materials, synthesizing tri-hydroxy fatty acid branched fatty acid ester triglyceride through esterification reaction, then completing purification by a molecular distillation technology, taking water as a substrate, taking lipase as a catalyst, directionally hydrolyzing to generate hydroxy fatty acid branched fatty acid ester, and finally deeply purifying by secondary molecular distillation to successfully prepare high-purity hydroxy fatty acid branched fatty acid ester. The technology has the advantages of simple operation, strong large-scale capacity, wide application scene and the like, and provides a new idea for high-value utilization of the natural fatty acid grease containing hydroxyl.

Inventors

  • JIN JUN
  • ZHEN CHENG
  • LI HAILING
  • Gong ren
  • JIN QINGZHE
  • WANG XINGGUO

Assignees

  • 江南大学
  • 山东天骄生物技术股份有限公司

Dates

Publication Date
20260512
Application Date
20251231

Claims (10)

  1. 1. A method for synthesizing hydroxy fatty acid branched-chain fatty acid ester by taking natural oil containing hydroxy fatty acid as raw material is characterized by comprising the following steps, The method comprises the steps of taking natural grease containing hydroxy fatty acid and fatty acid acyl chloride as raw materials, and esterifying and synthesizing tri-hydroxy fatty acid branched chain fatty acid ester triglyceride (TAG-FAHFA) under the action of an acid binding agent; molecular distillation is adopted to obtain high-purity TAG-FAHFA; hydrolyzing TAG-FAHFA by using immobilized lipase to obtain hydroxy fatty acid branched-chain fatty acid ester (FAHFA); purifying the branched fatty acid ester of hydroxy fatty acid by multistage molecular distillation to obtain FAHFA with high purity.
  2. 2. The method according to claim 1, wherein the natural fat or oil containing hydroxy fatty acid is one or more of castor oil, salfat, dilaury oil (Orychophragmus violaceus seed oil), lesqueella oil (Lesqueella oil) and its hydrogenated and fractionated products.
  3. 3. The method of claim 1 or 2, wherein the fatty acid chloride is one of caproic acid chloride, caprylic acid chloride, capric acid chloride, lauric acid chloride, myristic acid chloride, palmitic acid chloride, palmitoleic acid chloride, stearic acid chloride, oleic acid chloride, linoleic acid chloride, linolenic acid chloride, arachic acid chloride, behenic acid chloride, lignoceric acid chloride, EPA acid chloride, DPA acid chloride, DHA acid chloride, and nervonic acid chloride.
  4. 4. The method of claim 1, wherein the acid binding agent is one or more of triethylamine, pyridine, N-diisopropylethylamine.
  5. 5. The method according to claim 1, 2 or 4, wherein the esterification synthesizes a branched tri-hydroxy fatty acid ester triglyceride, wherein, The molar ratio of the substrate is 1:4-1:10, the temperature is 20-50 ℃, the time is 2-24 hours, the addition amount of the acid binding agent is 10-20% of the total mass of the substrate, the solvent is added for assisting dissolution, and the quenching agent is adopted for quenching after the reaction is finished; The solvent is one of dichloromethane or chloroform, and the addition amount is 6-8 times of the total mass of the substrate; the quenching agent is one of water, ethanol or methanol, and the addition amount is 0.8-1.5 times of the total mass of the substrate.
  6. 6. The method according to claim 5, wherein the parameters of molecular distillation purification of TAG-FAHFA are: The feeding speed is 0.5-1.5 mL/min, the absolute pressure is 2-8 Pa, the evaporation surface temperature is 120-180 ℃, the film scraping rotating speed is 100-150 r/min, and the distillation residue is high-purity TAG-FAHFA.
  7. 7. The method of claim 1, wherein the immobilized lipase enzyme is one or more of Palatase 20000L、Novozym 435、Lipozyme TL IM、Lipozyme RM IM、Novozym 40086、Lipase AY、Lipase DF-15、IM-NE100、NE-10、NE-20、R-001、RIM-03、AP6、Amano PS.
  8. 8. The method according to claim 1 or 7, wherein the step of hydrolyzing TAG-FAHFA with an immobilized lipase to obtain a branched fatty acid ester of a hydroxy fatty acid comprises, Taking water and TAG-FAHFA as substrates, wherein the molar ratio is 1:600-1:1500, the reaction time is 3-8 hours, the reaction temperature is 30-50 ℃, enzyme accounts for 8-12% of the total mass of the substrates, and emulsifying agent accounts for 0.2% of the total mass of the substrates; The emulsifier is one or more of deoxycholate, tween 20, triton 100, PEG-400 and polyricinoleate.
  9. 9. The method according to claim 8, wherein the purification of the branched fatty acid ester of a hydroxy fatty acid by multistage molecular distillation is carried out by the following parameters: Primary distillation, namely, the temperature of an evaporation surface is 160-180 ℃, the rotation speed of a film scraping is 100-150 r/min, the feeding rate is 1-1.6 ml/min, the condensation temperature is 40-60 ℃, and the distillation residue is taken; And (3) performing secondary distillation, namely obtaining distillate at the evaporation surface temperature of 200-260 ℃, the film scraping rotating speed of 120-160 r/min, the feeding rate of 1-1.6 ml/min and the condensing temperature of 30-40 ℃.
  10. 10. The branched fatty acid ester of a hydroxy fatty acid produced by the method of any one of claims 1 to 9.

Description

Method for synthesizing branched fatty acid ester of hydroxy fatty acid by taking natural oil containing hydroxy fatty acid as raw material Technical Field The invention belongs to the technical field of grease processing, and particularly relates to a method for synthesizing hydroxy fatty acid branched fatty acid ester by taking natural grease containing hydroxy fatty acid as a raw material. Background In 2014, american scientists found a new class of endogenous lipids, hydroxy fatty acid branched fatty acid esters (FAHFA), which are fatty acid esters composed of one molecule of fatty acid and one molecule of hydroxy fatty acid, and ester linkages composed of the hydroxy groups of hydroxy fatty acids and the carboxyl groups of fatty acids, in AG4OX mice (transgenic mice overexpressed by adipose tissue Glut 4). The branched fatty acid esters of hydroxy fatty acids generally exhibit the efficacy of improving insulin resistance and improving adipose tissue inflammation. Wherein 12-oleic acid hydroxystearate (12-OAHSA) can relieve adipose tissue inflammation and indirectly improve diabetes. At present, the synthesis of fatty acid ester lipid of hydroxy fatty acid branch chain is still in the experimental preliminary stage, and mass production is not possible. Disclosure of Invention This section is intended to outline some aspects of embodiments of the invention and to briefly introduce some preferred embodiments. The present invention has been made in view of the above and/or problems occurring in the prior art. Therefore, the invention aims to overcome the defects in the prior art and provide a method for synthesizing hydroxy fatty acid branched-chain fatty acid ester by taking natural grease containing hydroxy fatty acid as a raw material. In order to solve the technical problems, the invention provides a method for synthesizing hydroxy fatty acid branched-chain fatty acid ester by taking natural grease containing hydroxy fatty acid as raw material, The method comprises the steps of taking natural grease containing hydroxy fatty acid and fatty acid acyl chloride as raw materials, and esterifying and synthesizing tri-hydroxy fatty acid branched chain fatty acid ester triglyceride (TAG-FAHFA) under the action of an acid binding agent; molecular distillation is adopted to obtain high-purity TAG-FAHFA; hydrolyzing TAG-FAHFA by using immobilized lipase to obtain hydroxy fatty acid branched-chain fatty acid ester (FAHFA); purifying the branched fatty acid ester of hydroxy fatty acid by multistage molecular distillation to obtain FAHFA with high purity. As a preferable mode of the method, the natural grease containing the hydroxyl fatty acid is one or more of castor oil, salfat, dilaury oil (Orychophragmus violaceus seed oil), lesqueril oil (Lesqueril oil) and hydrogenation and fractionation products thereof. As a preferable mode of the method, the fatty acid acyl chloride is one of caproic acid acyl chloride, caprylic acid acyl chloride, capric acid acyl chloride, lauric acid acyl chloride, myristic acid acyl chloride, palmitic acid acyl chloride, palmitoleic acid acyl chloride, stearic acid acyl chloride, oleic acid acyl chloride, linoleic acid acyl chloride, linolenic acid acyl chloride, arachic acid acyl chloride, behenic acid acyl chloride, lignoceric acid acyl chloride, EPA acyl chloride, DPA acyl chloride, DHA acyl chloride and nervonic acid acyl chloride. As a preferable scheme of the method, the acid binding agent is one or more of triethylamine, pyridine and N, N-diisopropylethylamine. As a preferred embodiment of the method of the present invention, wherein the esterification is performed to synthesize a branched fatty acid triglyceride of a tri-hydroxy fatty acid, wherein, The molar ratio of the substrate is 1:4-1:10, the temperature is 20-50 ℃, the time is 2-24 hours, the addition amount of the acid binding agent is 10-20% of the total mass of the substrate, the solvent is added for assisting dissolution, and the quenching agent is adopted for quenching after the reaction is finished; The solvent is one of dichloromethane or chloroform, and the addition amount is 6-8 times of the total mass of the substrate; the quenching agent is one of water, ethanol or methanol, and the addition amount is 0.8-1.5 times of the total mass of the substrate. As a preferred embodiment of the method of the present invention, the parameters of the molecular distillation purification of TAG-FAHFA are: The feeding speed is 0.5-1.5 mL/min, the absolute pressure is 2-8 Pa, the evaporation surface temperature is 120-180 ℃, the film scraping rotating speed is 100-150 r/min, and the distillation residue is high-purity TAG-FAHFA. As a preferred embodiment of the method of the present invention, the immobilized lipase is one or more of Palatase 20000L、Novozym 435、Lipozyme TL IM、Lipozyme RM IM、Novozym 40086、Lipase AY、Lipase DF-15、IM-NE100、NE-10、NE-20、R-001、RIM-03、AP6、Amano PS. As a preferable scheme of the method, the method compri