Preparation of bio-based aromatic monomer and preparation method of related homopolyester and copolyester

A technology of aromatic monomer and homopolyester, which is applied in the field of green synthesis, can solve the problems of restricting the application of renewable resources, etc., and achieve the effect of green synthesis method, novel monomer, and favorable industrial production

Inactive Publication Date: 2021-01-26
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are relatively few reports on the synthesis of polyesters using monomers derived from citric acid derived from renewable resources, which limits the application of renewable resources in polyester production.

Method used

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  • Preparation of bio-based aromatic monomer and preparation method of related homopolyester and copolyester
  • Preparation of bio-based aromatic monomer and preparation method of related homopolyester and copolyester
  • Preparation of bio-based aromatic monomer and preparation method of related homopolyester and copolyester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: Preparation of 2,3-diphenyl-1,4-diethyl terephthalate monomer

[0032] After benzil (10g, 0.05mol), diethyl 1,3-acetonedicarboxylate (12g, 0.06mol) and methanol (70mL) were mixed and dissolved, sodium hydroxide (10g) was added and stirred at room temperature for 24h. The resulting product 2,5-diethoxycarbonyl-4-hydroxyl-3,4-diphenylcyclopentadienone (50g, 0.13mol) and acetic anhydride (100mL) were mixed uniformly, and then diluted with acetic anhydride was added dropwise Concentrated sulfuric acid (7 mL) solution was stirred at room temperature for 12 h, and quenched by adding water (300 mL). The resulting product 2,5-diethoxycarbonyl-3,4-diphenylcyclopentadienone (20g, 0.05mol) was mixed with dicycloheptadiene (19g, 0.21mol) and toluene (100mL) at 110 It was heated to reflux at ℃ for 12h, the solvent was removed under reduced pressure, and white crystals were obtained by recrystallization with methanol.

Embodiment 2

[0033] Example 2: Synthesis of homopolyester by 2,3-diphenyl-1,4-diethyl terephthalate and 1,10-decanediol

[0034] Add 2g (5.34mmol) 2,3-diphenyl-1,4-diethyl terephthalate and 1.49g (8.55mmol) 1,10-decanediol into a 100mL well-sealed three-neck flask, add Catalyst antimony trioxide and zinc acetate 0.63mg (2.67×10 -3 mmol), slowly feed nitrogen and continue to stir, heat to 160°C, react at this temperature for 3h, then raise the temperature to 240°C for 4h, remove the nitrogen protection, change the vacuum to 3mmHg, heat up to 260°C and continue the reaction for 8h , to obtain a viscous reaction solution, after the reaction solution was cooled to room temperature, 10 mL of chloroform was added to dissolve it, and then 100 mL of precipitating agent methanol was added to precipitate a white solid, which was filtered by suction and fully dried to obtain a homopolyester.

Embodiment 3

[0035] Example 3: Synthesis of homopolyester by 2,3-diphenyl-1,4-diethyl terephthalate and 1,8-octanediol

[0036]Add 2g (5.34mmol) 2,3-diphenyl-1,4-diethyl terephthalate and 1.25g (8.55mmol) 1,8-octanediol into a 100mL well-sealed three-neck flask, add Catalyst antimony trioxide and zinc acetate 0.63mg (2.67×10 -3 mmol), slowly feed nitrogen and continue to stir, heat to 160°C, react at this temperature for 3h, then raise the temperature to 240°C for 4h, remove the nitrogen protection, change the vacuum to 3mmHg, heat up to 260°C and continue the reaction for 8h , to obtain a viscous reaction solution, after the reaction solution was cooled to room temperature, 10 mL of chloroform was added to dissolve it, and then 100 mL of precipitating agent methanol was added to precipitate a white solid, which was filtered by suction and fully dried to obtain a homopolyester. .

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PUM

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Abstract

The invention relates to a preparation method of a citric acid group-based monomer and semi-aromatic homopolyester and copolyester thereof, which takes acetone dicarboxylic acid diethyl ester and various dihydric alcohols (HO-R-OH, -R- comprises at least one of the following structures) as raw materials, adopts a mixed catalyst, and realizes bulk polymerization under the conditions of high temperature and high vacuum. The preparation method comprises the following steps of 1) preparing 2, 5-diethoxycarbonyl-4-hydroxy-3, 4-diphenyl cyclopentadiene ketone from diethyl acetone dicarboxylate, (2)preparing 2, 5-diethoxycarbonyl-3, 4-diphenyl cyclopentadiene ketone from the 2, 5-diethoxycarbonyl-4-hydroxyl-3, 4-diphenyl cyclopentadiene ketone, (3) preparing 2, 3-diphenyl-1, 4-terephthalic aciddiethyl ester from 2, 5-diethoxycarbonyl-3, 4-diphenyl cyclopentadiene ketone, 4) synthesizing homopolyester from 2, 3-diphenyl-1, 4-terephthalic acid diethyl ester and dihydric alcohol with differentcarbon chain lengths, and 5) synthesizing copolyester from 2, 3-diphenyl-1, 4-terephthalic acid diethyl ester, terephthalic acid or ester thereof and various dihydric alcohols. The method has the advantages that the raw materials are low in price and wide in source, the synthesis process is simple and environmentally friendly, the polymerization product has high glass-transition temperature and good thermal stability and can be degraded, and industrial production and structural and functional diversification can be achieved.

Description

technical field [0001] The invention relates to the technical field of green synthesis of renewable resources, in particular to a preparation method of a citric acid-based monomer and its semi-aromatic homopolyester and copolyester. Background technique [0002] Polyester is a thermoplastic engineering plastic with excellent comprehensive properties. Its excellent impact resistance, dimensional stability, and strong heat resistance and oxygen barrier properties make polyester widely used in various packaging materials, agricultural films, biomedicine, etc. , information electronics and other fields are widely used. With the development of the polyester industry, the demand for polyester materials is increasing day by day, and a large amount of waste polyester materials are burned, discarded or buried, which has caused serious environmental pollution and also exacerbated the shortage of petrochemical and land resources. With the increasing awareness of environmental protecti...

Claims

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Application Information

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IPC IPC(8): C08G63/183C08G63/78
CPCC08G63/183C08G63/78
Inventor 管延珍庞成才高辉
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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