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Preparation method of hydroxy fatty acid glyceride

A technology of hydroxy fatty acid glyceride and glycerol, which is applied in the field of ester preparation and achieves the effects of mild reaction conditions, high safety and improved transesterification rate

Active Publication Date: 2014-04-16
DONGGUAN BOTON FLAVORS & FRAGRANCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, there are no reports at home and abroad on the method for preparing hydroxy fatty acid glycerides by biocatalysis

Method used

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  • Preparation method of hydroxy fatty acid glyceride
  • Preparation method of hydroxy fatty acid glyceride
  • Preparation method of hydroxy fatty acid glyceride

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preparation example Construction

[0037] In one embodiment, the preparation method of hydroxy fatty acid glyceride comprises the following steps:

[0038] Mixing step: add lactone, glycerin with 0.5-10 times the amount of lactone substance, water with 0.05-10 times the amount of lactone substance, main solvent with 0-200 times the amount of lactone substance, 0 An auxiliary solvent of ~20 times the amount of the lactone substance, and a lipase of 0.01%-5.0% by weight of the lactone;

[0039] Reaction steps: react at 30 to 80° C., and obtain a reaction liquid containing hydroxy fatty acid glyceride after reaching an equilibrium state.

[0040] Wherein, the main solvent refers to an organic solvent capable of dissolving at least one of lactone and glycerol, generally a hydrophilic solvent, which can be one or more of tert-butanol, tert-amyl alcohol, acetone and ionic liquid Multiple mixing, described auxiliary solvent refers to the organic solvent that can promote the dissolubility of reaction substrate in main...

Embodiment 1

[0054] Add 170.250 g (1 mol) δ-decalactone, 920.090 g (10 mol) glycerol, 18.016 g (1 mol) water, 7412.160 g (100 mol) tert-butanol and 7.812 g (0.1 mol) dimethyl sulfoxide to the enzyme reactor Add 5g of immobilized Candida lipase, and stir the reaction at 60°C for 24 hours. The reaction basically reaches equilibrium, and 5-hydroxycapric acid glyceride (monoester and diester) is produced, and the remaining unreacted δ - Decalactone 112.458g (0.66mol), the transesterification rate of δ-decalactone reached 34%.

[0055] Finish the reaction, inactivate the enzyme, remove the lipase by filtration, carry out vacuum distillation on the reaction liquid to remove tert-butanol, water, most of dimethyl sulfoxide and glycerin, and put the distillation residue under the conditions of temperature 50°C and vacuum degree 200Pa Carry out molecular distillation, glycerol, dimethyl sulfoxide and part of δ-decalactone are distilled out, and the remaining part of molecular distillation is extract...

Embodiment 2

[0057] Add 114.140g (1mol) γ-caprolactone, 92.090g (1mol) glycerin, 1.802g (0.1mol) water and 580.800g (10mol) acetone to the enzyme reactor, then add 0.2g porcine pancreatic lipase, The reaction was stirred at 50°C for 96 hours, and the reaction basically reached equilibrium, producing 4-hydroxycaproic acid glyceride (monoester, diester, triester), and the remaining unreacted γ-caprolactone 51.071g (0.45mol), γ -The transesterification rate of caprolactone reaches 55%.

[0058] Finish the reaction, inactivate the enzyme, remove the lipase by filtration, carry out normal pressure and reduced pressure distillation on the reaction solution to remove acetone, water, part of γ-caprolactone and glycerin, and put the distillation residue under the conditions of temperature 80°C and vacuum degree 20Pa Molecular distillation is carried out, glycerin, γ-caprolactone and 4-hydroxycaproic acid glyceride are distilled, and the distilled part is subjected to silica gel column chromatograph...

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Abstract

Disclosed is a process for preparing a hydroxyl fatty acid glyceride, comprising the following steps: a mixing step: adding into an enzyme reactor, a lactone, a glycerol in a molar amount 0.5-10 times the lactone, water in a molar amount 0.05-10 times the lactone, a main solvent in a molar amount 0-200 times the lactone, a secondary solvent in a molar amount 0-20 times the lactone, and a lipase in an amount 0.01%-5.0% of the lactone weight; and a reaction step: reacting same under conditions of 30-80°C, and after having reached balance, obtaining a reaction solution comprising hydroxyl fatty acid glyceride. The present invention can prepare a hydroxyl fatty acid glyceride, and has the advantages of mild reaction conditions, being energy saving and reduced consumption, and high reaction efficiency, etc., compared with traditional chemical synthesis technology. In addition, the synthesis reaction of the present invention uses a lipase as a catalyst, has strong reaction specificity, no by-product, and a high level of safety, and at the same time the reaction is not subject to strong acids and base, or high temperature and pressure processes so the quality of the product is relatively high.

Description

technical field [0001] The invention relates to the preparation of esters, in particular to a method for preparing hydroxy fatty acid glycerides. Background technique [0002] Lactone, the English name latctones, refers to the cyclic ester formed by removing a part of water from the hydroxyl group and carboxyl group in the carboxylic acid molecule containing hydroxyl group. Common lactones are x=2, 3 or 4, which are called β-, γ- or δ-lactones, respectively. Low-level (smaller ring) lactones are scented liquids that can be used as food flavorings (see Table 1), and are easily soluble in water, ethanol and ether. [0003] Table 1 Some lactones that can be used as food flavoring [0004] [0005] The properties of lactones are similar to open-chain carboxylic acid esters, and react with water (in the presence of acid or base), alcohol or ammonia to generate corresponding hydroxy fatty acids, hydroxy fatty acid esters or hydroxy amides. Lactones react with glycerol to pro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P7/62C12P7/6445
CPCC12P7/6445C12P7/62
Inventor 姜兴涛邹慧余汉谋李锐李庆廷李庆龙
Owner DONGGUAN BOTON FLAVORS & FRAGRANCES
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