Preparation method of glycerol monostearate p-hydroxybenzoate

A technology of p-hydroxybenzoic acid and sodium hydroxybenzoate, which is applied in the field of preparation of monoglyceride p-hydroxybenzoate, can solve the problems that glycidol raw materials are difficult to obtain, difficult to obtain, and high price of lipase, and achieve good industrial application prospects and operation Simple and convenient, high purity and high yield

Inactive Publication Date: 2013-12-18
LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation method of monoglyceride includes direct esterification method, the direct conversion rate of this method is low, and molecular distillation and extraction are required for separation; the glycidol method uses glycidol and acid to react, and the yield is not very high , and in industrial production, glycidol raw materials are not easy to obtain
Chemical group protection method, the two hydroxyl groups on the glycerin molecule are condensed and dehydrated to form isobutylidene glycerol, and then esterified with isobutylidene monoglyceride, and finally the isobutylidene protection group is decomposed. The raw materials of this method are easy to obtain, and the product High purity, but complex post-processing
The enzymatic directional hydrolysis method prepares monoglycerides at a lower temperature, and the product has a better color. The main disadvantage is that the price of lipase is too high, it is not easy to obtain, and the enzyme is easily inactivated

Method used

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  • Preparation method of glycerol monostearate p-hydroxybenzoate
  • Preparation method of glycerol monostearate p-hydroxybenzoate

Examples

Experimental program
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Effect test

Embodiment 1

[0021] ①Weigh 2g of sodium p-hydroxybenzoate, 0.03g of tetrabutylammonium bromide, 2ml of epichlorohydrin and 4.2ml of xylene into a sealed stainless steel reactor with magnetic stirring, and react at 115°C for 110 minutes and then The reactor is cooled and opened, and the liquid phase (including unreacted chlorocyclopropane and a large amount of solvent) is poured into a fixed waste liquid bottle, which is used for distilling and recovering the solvent after the reaction is completed. The solid phase was separated from the rotor and transferred to a 50 ml small beaker for later use.

[0022] ② Measure 20ml of 0.02mol / L dilute sulfuric acid solution, pour it into a small beaker containing the intermediate product, and stir for 50 minutes under heating at 80°C. After the reaction, rinse the solid phase with a large amount of deionized water to make the oily and The viscous solid phase is cooled and hardened, and the residual impurities (acid, sodium chloride, catalyst, etc.) ar...

Embodiment 2

[0024] ① Weigh 2g of sodium p-hydroxybenzoate, 0.04g of tetrabutylammonium bromide, 3ml of epichlorohydrin and 5.6ml of xylene into a sealed stainless steel reactor with magnetic stirring, and react at 115°C for 110 minutes The reactor is cooled and opened, and the liquid phase (including unreacted chlorocyclopropane and a large amount of solvent) is poured into a fixed waste liquid bottle, which is used for distilling and recovering the solvent after the reaction is completed. The solid phase was separated from the rotor and transferred to a 50 ml small beaker for later use.

[0025] ② Measure 20ml of 0.03mol / L dilute sulfuric acid solution, pour it into a small beaker containing the intermediate product, and stir for 50 minutes under heating at 80°C. After the reaction, wash the solid phase with a large amount of deionized water to make the oily and The viscous solid phase is cooled and hardened, and the residual impurities (acid, sodium chloride, catalyst, etc.) are washed ...

Embodiment 3

[0027] ① Weigh 2g of sodium p-hydroxybenzoate, 0.05g of tetrabutylammonium bromide, 3.5ml of epichlorohydrin and 7.0ml of xylene into a sealed stainless steel reactor with magnetic stirring, and react at 115°C for 110 minutes Cool and open the reactor, pour the liquid phase (including unreacted chlorocyclopropane and a large amount of solvent) into a fixed waste liquid bottle, and reserve it for distillation and recovery of the solvent after the reaction. The solid phase was separated from the rotor and transferred to a 50 ml small beaker for later use.

[0028] ② Measure 20ml of 0.04mol / L dilute sulfuric acid solution, pour it into a small beaker containing the intermediate product, and stir for 50 minutes under heating at 80°C. After the reaction, rinse the solid phase with a large amount of deionized water to make the oily and The viscous solid phase is cooled and hardened, and the residual impurities (acid, sodium chloride, catalyst, etc.) are washed away, and the obtained...

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Abstract

The invention discloses a preparation method of glycerol monostearate p-hydroxybenzoate, which comprises the following steps: (1) proportionally weighing sodium p-hydroxybenzoate and epoxy chloropropane; adopting tetrabutylammonium bromide as a phase transfer catalyst, adding a proper amount of solvent, and reacting in a sealed constant-temperature stirring reactor; and cooling to obtain an intermediate product glycidyl ester p-hydroxybenzoate; (2) measuring the prepared sulfuric acid solution, pouring into a container with the intermediate product obtained by the step (1), putting the container into a water bath kettle for a constant-temperature heating stirring reaction, and flushing a solid phase by use of deionized water to remove residual impurities; and finally transferring the reaction product in the container into watch glass, and drying and cooling to obtain a glycerol monostearate p-hydroxybenzoate product. By adopting the method disclosed by the invention, the obtained product has high purity and yield over 99.9% and 95% respectively; the operation is simple and convenient, the product is pure, and no meta-position byproduct is generated; the method has a great prospect in industrial application and deserves wide popularization and application.

Description

1. Technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of monoglyceryl p-hydroxybenzoate used as a preservative and an emulsifier. 2. Background technology [0002] Paraben is one of the three broad-spectrum food preservatives recognized internationally. Compared with sodium benzoate and potassium sorbate, it mainly has good antibacterial effect and a wide range of applicable pH , less toxic and side effects, low cost and easy to use. [0003] Monoglyceride derivatives are polyol-type nonionic surfactants. Monoglyceride is the most productive emulsifier. It has excellent properties such as emulsification, dispersion, solubilization, and wetting. It is widely used in food, Daily chemicals, pharmaceuticals, plastics and other departments. [0004] Monoglyceryl p-hydroxybenzoate has both antiseptic and emulsifying functions, and there are few studies at present. The preparation method of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/84C07C67/29
Inventor 李剑杨丽娜周瑜
Owner LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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