Preparation method of hydroxy fatty acid glyceride

A technology of hydroxy fatty acid glyceride and glycerin, which is applied in the field of ester preparation, to achieve the effects of reducing reaction tendency, increasing transesterification rate, and mild reaction conditions

Active Publication Date: 2012-01-18
DONGGUAN BOTON FLAVORS & FRAGRANCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

The invention discloses a preparation method of hydroxy fatty acid glyceride, which comprises the following steps: mixing: adding lactone, glycerol (0.5-10 times of lactone by mole), water (0.05-10 times of lactone by mole), primary solvent (0-200 times of lactone by mole), secondary solvent (0-20 times of lactone by mole) and lipase (0.01-5.0 wt% of lactone) into an enzyme reactor; and reaction: reacting at 30-80 DEG C, and obtaining a reaction liquid containing hydroxy fatty acid glyceride after achieving an equilibrium state. The method disclosed by the invention can be used for preparing hydroxy fatty acid glyceride. Compared with the traditional chemical synthesis technology, the invention has the advantages of mild reaction conditions, energy saving, consumption reduction, high reaction efficiency and the like; and in addition, by using lipase as the catalyst for synthetic reaction, the invention also has the advantages of high reaction specificity, no byproduct, high safety and higher product quality, and does not need strong acid, strong base, high pressure or high temperature in the reaction process.

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 Applications(China)
IPC IPC(8): C12P7/62
CPCC12P7/62C12P7/6445
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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