A kind of polycitrate triester and preparation method thereof

A technology of citric acid three and citric acid, applied in the field of plastic rubber plasticizers, can solve the problems of poor solvent extraction resistance and migration resistance, poor solvent extraction resistance and migration resistance, and failure to overcome thermal stability and the like, Achieve good migration resistance, meet industrial production requirements, and increase the effect of relative molecular weight

Inactive Publication Date: 2017-01-04
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the small molecular weight, the ratio of the number of non-polar aliphatic carbon atoms to the number of polar ester groups (A P / A O ) and other reasons, the current citrate triester plasticizers still have shortcomings such as thermal stability, low temperature flexibility, solvent extraction resistance and migration resistance in actual use.
Scientific research workers have improved citrate triester plasticizers, such as octadecyl tributyl citrate (CN101255240A), oleoyl tributyl citrate (CN101255114A), butenedioic acid tributyl citrate bis The development of a series of products such as ester (CN101781213A); at the same time, the development of double citrate triester (US3239555, CN1037350A) is to connect two citrate triester molecules through fatty chains (usually 1 to 12 carbon atoms) to form a Dicitrate triester molecule; Although this type of dicitrate triester molecule has improved the plasticizing effect to a certain extent, it still has not overcome the shortcomings of thermal stability, low temperature flexibility, solvent extraction resistance and poor migration resistance. Its application is limited and cannot meet the actual needs

Method used

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  • A kind of polycitrate triester and preparation method thereof
  • A kind of polycitrate triester and preparation method thereof
  • A kind of polycitrate triester and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The preparation of tributyl trimesic acid tricitrate comprises the following steps:

[0040] 1) Preparation of tributyl citrate: add 100mol citric acid, 380mol butanols, p-benzenemethanesulfonic acid (mass fraction is 2% of the total mass of citric acid and alcohol) and 40L water-carrying agent cyclohexane in the reactor , heated to 120°C under stirring, refluxed for 4 hours, recovered excess alcohol by distillation under reduced pressure to obtain crude tributyl citrate, then washed the crude tributyl citrate with 2% sodium bicarbonate solution, removed the catalyst, and recovered the organic phase to obtain Tributyl Citrate.

[0041] 2) Preparation of trimesoyl chloride: 70 mol of trimesic acid was added to the reaction kettle, 210 mol of phosphorus trichloride was added dropwise, the temperature was raised to 60° C. with stirring, cooled to room temperature, and trimesoyl chloride was obtained by standing and stratifying.

[0042] 3) Preparation of tributyl trimesic...

Embodiment 2

[0044] The preparation of tributylmalonate tricitrate comprises the following steps:

[0045] 1) Preparation of tributyl citrate: add 100mol citric acid, 400mol butanols, p-benzenemethanesulfonic acid (mass fraction is 2% of the total mass of citric acid and alcohol) and 40L water-carrying agent cyclohexane in the reactor , heated to 140°C under stirring, refluxed for 4 hours, and recovered excess alcohol by distillation under reduced pressure to obtain crude tributyl citrate, then washed the crude tributyl citrate with 2% sodium bicarbonate solution, removed the catalyst, and recovered the organic phase to obtain Tributyl Citrate.

[0046] 2) Preparation of glycerinyl chloride: add 70 mol of glyceric acid into the reaction kettle, dropwise add 210 mol of phosphorus trichloride, stir and heat up to 60° C., cool to room temperature, stand and separate to obtain glycerinyl chloride.

[0047] 3) Preparation of tributyl malonate tricitrate: add 100mol tributyl citrate and an appr...

Embodiment 3

[0049] The preparation of trioctyl trimesic acid tricitrate comprises the following steps:

[0050] 1) Preparation of trioctyl citrate: add 100mol citric acid, 380mol octanol, p-benzenemethanesulfonic acid (mass fraction is 2% of the total mass of citric acid and alcohol) and 40L water-carrying agent cyclohexane in the reactor , heated to 150°C under stirring, refluxed for 4 hours, recovered excess alcohol by distillation under reduced pressure to obtain crude trioctyl citrate, then washed the crude trioctyl citrate with 2% sodium bicarbonate solution, removed the catalyst, and recovered the organic phase to obtain Trioctyl Citrate.

[0051] 2) Preparation of trimesoyl chloride: 70 mol of trimesic acid was added to the reaction kettle, 200 mol of phosphorus trichloride was added dropwise, the temperature was raised to 60° C. with stirring, cooled to room temperature, and trimesoyl chloride was obtained by standing and stratifying.

[0052] 3) Preparation of trioctyl trimesic ...

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PUM

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Abstract

The invention discloses a polycitrate triester and a preparation method thereof. The preparation method of the polycitrate triester is to prepare the citrate triester by reacting citric acid and alcohol, and then prepare polybasic acid chloride by acylation of polybasic carboxylic acid. Polyacyl chlorides and citrate triesters are prepared by esterification to obtain polycitrate triesters. The preparation method is simple to operate, has wide sources of raw materials, mild reaction conditions, and meets industrial production requirements. The obtained polycitrate triesters have good growth Plastic effect and excellent thermal stability, low temperature flexibility, solvent extraction resistance and migration resistance, can be widely used in plastic rubber plasticizers.

Description

technical field [0001] The invention relates to a polycitrate triester and a preparation method thereof, belonging to the technical field of plasticizers for plastics and rubbers. Background technique [0002] Plasticizer is the category with the largest production capacity and consumption among plastic processing aids. Especially since the 1980s, with the continuous development of polyvinyl chloride (PVC) products, the plasticizer industry has shown a situation of rapid development. Compared with foreign countries, the variety of plasticizers in my country is slightly single, mainly phthalates, of which dioctyl phthalate (DOP) and dibutyl phthalate (DBP) account for a large proportion . Due to the toxicity of plasticizers, some application fields of traditional primary plasticizers are limited. For example, studies have shown that DOP and DBP may have potential carcinogenic risks, and the benzene ring in the structure of phthalate diester (DEHP) can cause cancer. . Many c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/14C07C69/76C07C69/704C08K5/11C08K5/12
Inventor 潘春跃喻桂朋崔霁第刘青山郑大田
Owner CENT SOUTH UNIV
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