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Cyclic trimetric polybutylene terephthalate preparation method

A technology for polybutylene terephthalate and terephthalate, which is applied in the field of compound preparation, can solve the problems of long synthesis process, high cost, complicated operation and the like, and achieves short synthesis route, simple operation and conditions easy-to-control effects

Active Publication Date: 2018-05-18
EAST CHINA NORMAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method has low yield, complicated operation and high cost
The other is the chemical method. In the patent (authorized announcement number: CN103755677B) applied by Zhang Lei of Tianjin Alta Technology Co., Ltd., he synthesized compounds with carboxyl and hydroxyl groups at both ends, and closed the ring through condensation reaction. This method requires up to ten steps for the synthesis of cyclic tripolybutylene terephthalate, and the synthesis process is lengthy

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] In a one-necked bottle, dissolve 1.43g of bis-(4-hydroxybutyl)-terephthalate and 1.57g of 4-(allyloxycarbonyl)benzoic acid in 20mL of chloroform, add 0.18g of DMAP, 2.33g of EDCI in sequence , heated to 85°C for reaction. After 24 hours of reaction, TLC detected that the reaction of raw materials was complete. Dilute hydrochloric acid was added for extraction, washed with water, the organic phase was separated, dried over anhydrous sodium sulfate, evaporated to dryness, and purified by column chromatography with chloroform. 1.58 g of (III) bis(4-(4-allylterephthaloyloxy)butyl)terephthalate was obtained in a yield of 75%.

[0042] 1 H NMR (400MHz, CDCl 3 )δ8.04(dd, J=9.3,6.9Hz,12H),5.98(ddd,J=22.5,10.9,5.7Hz,2H),5.42–5.20(m,4H),4.78(d,J=5.6Hz ,4H),4.37(s,8H),1.91(s,8H).

[0043] MS(ESI):m / z[M+Na] + :709.

[0044] In a single-necked bottle, 1.43g of bis-(4-hydroxybutyl)-terephthalate and 1.57g of 4-(allyloxycarbonyl)benzoic acid were dissolved in 20mL of chloroform...

Embodiment 2

[0051] Add 1.5g bis(4-(4-allyl terephthaloyloxy) butyl) terephthalate in the one-necked bottle, dissolve 0.75g Grubbs second-generation catalyst in chloroform, dropwise Then add 0.62g tetraisopropyl titanate and react at room temperature. The reaction was carried out for 12 hours, and TLC detected that the reaction of the raw materials was complete. The solid was removed by suction filtration, washed with water, dried, evaporated to dryness, and purified by column chromatography with a volume ratio of chloroform to ethyl acetate of 40:1. 0.94 g of the cyclic tripolybutylene terephthalate precursor of formula (IV) was obtained, and the yield was 65%.

[0052] 1 H NMR (400MHz, CDCl 3 )δ8.05(dd,J=9.0,6.8Hz,12H),5.98(s,2H),4.83(s,4H),4.36(s,8H),1.88(s,8H).

[0053] MS(ESI):m / z[M+Na] + :681.

[0054] Add 1.5g bis(4-(4-allyl terephthaloyloxy) butyl) terephthalate in the one-necked bottle, dissolve 0.75g Grubbs first-generation catalyst in chloroform, dropwise Then add 0.62 g ...

Embodiment 3

[0061] Dissolve 1.2 g of cyclic tripolybutylene terephthalate precursor in 20 mL of tetrahydrofuran in a one-necked bottle, add 0.24 g of palladium carbon, replace hydrogen, and react at room temperature. After 8 hours of reaction, TLC detected that the reaction of the raw materials was complete. The solid was removed by suction filtration, and the filtrate was evaporated to dryness and dried. 0.72 g of cyclic tripolybutylene terephthalate of formula (V) was obtained, and the yield was 95%.

[0062] 1 H NMR (400MHz, CDCl 3 )δ8.03(s,12H),4.36(s,12H),1.88(s,12H).

[0063] MS(ESI):m / z[M+Na] + :683.

[0064] Dissolve 1.2 g of cyclic tripolybutylene terephthalate precursor in 20 mL of tetrahydrofuran in a one-necked bottle, add 0.24 g of palladium carbon, replace hydrogen, and react at room temperature. React for 4 hours. The solid was removed by suction filtration, the filtrate was evaporated to dryness, and purified by beating with petroleum ether and ethyl acetate at a vo...

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Abstract

The invention discloses a cyclic trimetric polybutylene terephthalate preparation method. The method comprises the steps: (a) preparing bis(4-(4-allyl terephthaloyl oxy)butyl)polyethylene terephthalate (III) from bis-(4-hydroxyl butyl)-polyethylene terephthalate (I) and 4-(allyloxy carbonyl)benzoic acid (II) under action of a condensing agent and an auxiliary reagent; (b) preparing cyclic trimetric polybutylene terephthalate precursor (IV) by ring closure of the bis(4-(4-allyl terephthaloyl oxy)butyl)polyethylene terephthalate (III) under the action of a Grubbs catalyst and lewis acid; (c) hydrogenating the cyclic trimetric polybutylene terephthalate precursor under the action of Pd / C to obtain cyclic trimetric polybutylene terephthalate (V). The preparation method disclosed by the invention has the advantages that the raw materials are cheap and easy to obtain, a synthesizing route is simple and short, a yield is high, and conditions are easy to control.(The formula is shown in the description.).

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular to a preparation method of cyclic tripolybutylene terephthalate. Background technique [0002] Polybutylene terephthalate, PBT for short, is a polymer of terephthalic acid and 1,4-butanediol. PBT is a thermoplastic polyester engineering plastic with excellent performance, high rigidity and hardness, good thermal stability, excellent wear resistance, good chemical corrosion resistance, and excellent impact resistance. Therefore, PBT is widely used in electronic appliances and accessories, auto parts, mechanical equipment, textile fields, etc. [0003] Although the content of cyclic polymers with low degree of polymerization in PBT plastics is small, it is an important factor affecting the quality of plastics, especially the high content of cyclic dibutylene terephthalate and cyclic trimer. Butylene glycol phthalate has thus attracted extensive attention and research in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D323/00
CPCC07D323/00
Inventor 罗宇李晓林周朴朱皓庭何洋张玉柳占莉杨世琼李倩康立涛
Owner EAST CHINA NORMAL UNIV
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