Acetylated citric acid fatty acid ester plasticizer, preparation method thereof and application

A technology for acetylating citric acid and fatty acid ester, which is applied in the preparation of carboxylate, chemical instruments and methods, preparation of organic compounds, etc., can solve problems such as poor compatibility and precipitation, achieve mild conditions, reduce dependence, and process simple effect

Inactive Publication Date: 2017-09-19
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to poor compatibility with PVC resin, this kind of plasticizer is easy to precipitate

Method used

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  • Acetylated citric acid fatty acid ester plasticizer, preparation method thereof and application
  • Acetylated citric acid fatty acid ester plasticizer, preparation method thereof and application
  • Acetylated citric acid fatty acid ester plasticizer, preparation method thereof and application

Examples

Experimental program
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Effect test

Example Embodiment

[0027] Example 1

[0028] The first step is the preparation of epoxidized methyl oleate: take 45 mL of hydrogen peroxide with a concentration of 30 wt.% and add dropwise to a three-necked flask with 30 g methyl oleate, 30 mL acetic acid and 1.5 g ion exchange resin catalyst to control the hydrogen peroxide After 1.5h the dripping is completed, and the temperature is not higher than 65℃, then keep the temperature at 65℃ and react for 3h. After the reaction, neutralize with 4wt.% sodium carbonate solution, wash with water to neutrality, and then dry to obtain an epoxy value of 3.6% Light yellow epoxidized methyl oleate.

[0029] In the second step, citric acid and epoxidized fatty acid methyl esters are ring-opened to prepare citric acid fatty acid esters. 100g of epoxidized methyl oleate, 13g of citric acid, 1010 0.1g of antioxidant and catalyst are obtained in the first step. 0.4g of dimethylimidazole, reacted at 140°C for 3 hours to obtain a crude product with an acid value of 0....

Example Embodiment

[0031] Example 2

[0032] The first step is the preparation of epoxidized fatty acid methyl esters: 50mL of hydrogen peroxide with a concentration of 30wt.% is added dropwise to the mixture of 30g methyl oleate, 20mL ethyl acetate and 1.2g phosphotungstic heteropoly acid quaternary ammonium salt catalyst. In a three-necked flask, the controlled hydrogen peroxide was added dropwise in 2.0h, the temperature was not higher than 65℃, and then kept at 65℃ for 3h. After the reaction, neutralized with 4wt.% sodium carbonate solution, washed with water to neutrality, and dried to obtain epoxy Value 4.1% yellowish epoxidized methyl oleate.

[0033] In the second step, citric acid and epoxidized fatty acid methyl esters are ring-opened to prepare citric acid fatty acid esters. 100g of epoxidized methyl oleate, 14g of citric acid, 168 0.1g of antioxidants and catalyst are obtained in the first step. Diethylenetriamine 0.3g, reacted at 140°C for 4 hours to obtain a crude product with an acid ...

Example Embodiment

[0035] Example 3

[0036] The first step, the preparation of epoxidized methyl ricinoleate: Take 55mL of 30wt.% hydrogen peroxide and add dropwise to 30g of methyl ricinoleate, 20mL of ethyl acetate and 1.2g of quaternary ammonium phosphotungstate. In the salt catalyst three-necked flask, the controlled hydrogen peroxide was added dropwise in 2h, the reaction temperature was not higher than 65℃, and then kept at 65℃ for 3h. After the reaction, it was neutralized with 4% sodium carbonate solution, washed with water to neutrality, and then dried. A yellowish epoxidized methyl ricinoleate with an epoxy value of 3.8% was obtained.

[0037] In the second step, citric acid and epoxidized methyl ricinoleate are ring-opened to prepare citric acid fatty acid esters. 100g of epoxidized methyl ricinoleate, 14g of citric acid and 50% Phosphoric acid 0.2g and catalyst tetrabutylammonium chloride 0.2g, reacted at 140℃ for 3.5 hours to obtain a crude product with an acid value of 0.98mg / g, and t...

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Abstract

The invention discloses an acetylated citric acid fatty acid ester plasticizer, a preparation method thereof and an application. The preparation method includes the steps: preparing epoxidation fatty acid ester; performing ring-opening reaction on citric acid and fatty acid ester to prepare citric acid fatty acid ester; performing acetylation reaction to obtain the acetylated citric acid fatty acid ester plasticizer. According to the plasticizer, the citric acid and the fatty acid ester serve as main materials to prepare a biological base plasticizer, the raw materials are low in cost, easy to acquire, green and environmentally friendly, dependence on petrochemical resources can be relieved, molecular weight is high, the content of polar bonds is high, a long fatly chain exists, so that the plasticizer is high in flashing point, resistant in precipitation and cold and good in plasticizing efficiency as compared with acetyl tributyl citrate and epoxidized fatty acid methyl ester, thermal stability of PVC (polyvinyl chloride) products can be improved, and the plasticizer can completely replace DOP (dioctyl-phthalate) to prepare the PVC products with special performance. The preparation method is simple in process, mild in condition and quite suitable for industrial production, and the plasticizer can be directly produced without changing production devices.

Description

technical field [0001] The invention belongs to the field of bio-based materials, and relates to a preparation method of an environment-friendly, bio-based PVC plasticizer, acetylated citric acid fatty acid ester. Background technique [0002] Bio-based materials refer to a new class of materials manufactured by biological, chemical and physical means using renewable biomass, including crops, trees and other plants and their residues and contents as raw materials. It mainly includes bioplastics, bio-based platform compounds, biomass functional polymer materials, functional sugar products, wood-based engineering materials and other products, which are green, environmentally friendly, renewable and biodegradable. The main materials oil and citric acid used in the present invention belong to renewable biomass. Plasticizers are plastic additives that can be added to polymer materials to change the plasticity of the material, making it easier to process and making the product so...

Claims

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Application Information

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IPC IPC(8): C07C69/67C07C67/31C07C67/26C07C69/704C07D301/12C07D303/42C08K5/11C08L27/06
Inventor 冯国东周永红马艳许彬张猛刘承果
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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