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Method for catalyzing gamma-valerolactone to be subjected to ring-opening polymerization by utilizing biomimetic catalyst

A technology of biomimetic catalyst and ring-opening polymerization, which is applied in the field of using biomimetic catalyst to catalyze the ring-opening polymerization of γ-valerolactone, can solve the problem of single substrate of polyester, and achieve high catalytic efficiency, wide sources and low dosage Effect

Inactive Publication Date: 2017-08-08
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] CN 105348495, CN 106478928, CN 106478933 and CN 104530393 have greatly improved organic catalysts, such as the preparation of carbene ionic liquids, and the addition of hydrogen bond donors to thiourea amides to speed up the reaction rate and efficiency, but there are still extremely big room for improvement
On the other hand, the polyester substrate is relatively simple, the polylactic acid monomer is lactide, the polycaprolactone monomer is ε-caprolactone, and other branched aliphatic lactones have less ring-opening polymerization. There is a lot of room for research

Method used

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  • Method for catalyzing gamma-valerolactone to be subjected to ring-opening polymerization by utilizing biomimetic catalyst
  • Method for catalyzing gamma-valerolactone to be subjected to ring-opening polymerization by utilizing biomimetic catalyst
  • Method for catalyzing gamma-valerolactone to be subjected to ring-opening polymerization by utilizing biomimetic catalyst

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Preparation of aminothiazole-based biomimetic catalyst (CAZ): 3.3 mmol of benzoyl chloride was dissolved in 5 mL of THF, and 3 mmol of 2-amino-5,6-dimethylbenzimidazole and 5.7 mmol of N,N-diisopropyl were added dropwise The THF solution of ethylamine (15ml), the mixture was stirred at room temperature for 16h, after the reaction was completed, the reaction solution was evaporated to dryness, and the aminothiazole catalyst intermediate was obtained by column chromatography, and then 3mmol of the intermediate and 3mol of Lawson's reagent were taken, and 60ml of toluene was added as Solvent, under nitrogen protection, heating and refluxing for 16h, after the reaction, vacuum drying, column chromatography to obtain N-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)benzothiol amide.

Embodiment 2

[0032] Preparation of thiourea amide biomimetic catalyst (CSA): under argon protection, 1 mmol 3,5-bis(trifluoromethyl) phenyl isothiocyanate was dissolved in 1 ml of anhydrous THF, and N, N-dimethylcyclohexanediamine 2.23mmol, the reaction was stirred for 3h, the mixture was concentrated in vacuo, and the oily substance was purified by column chromatography to obtain -3,5-bis(trifluoromethyl)phenyl)-3-(2-(bis Methylamino) cyclohexyl) thiourea biomimetic catalyst.

Embodiment 3

[0034] Preparation of phenyl phosphate biomimetic catalyst pyrophosphoric acid catalyst (IDPA): firstly synthesize diphenyl ester phosphoramide, take 3 mmol of diphenyl chlorophosphate in a 50 ml flask in an anhydrous and oxygen-free environment, and pass it through it at -78 ° C Ammonia gas was added to react for 2 h. After the reaction, the cooling bath was removed, the product was vacuum-dried, and the product was purified by column chromatography (dichloromethane was used as the eluent). Get 2mmol diphenyl ester phosphoramide and 2mmol diphenyl chlorophosphate and 50ml flask, add 5ml THF to it, add 5mmol 60% sodium hydroxide solution to it in addition, stir at room temperature for 14h, add 10ml 10% after the reaction finishes Hydrochloric acid and 10 ml of dichloromethane (DCM), stirred for 1 h, the organic phase was taken out, and the product was purified by column chromatography.

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Abstract

The invention provides a method for catalyzing gamma-valerolactone to be subjected to ring-opening polymerization by utilizing a biomimetic catalyst and belongs to the field of biomass high molecular materials. According to the method, the gamma-valerolactone is used as a monomer, the biomimetic catalyst is used as a catalyst and an alcohol compound is used as an initiator, and the gamma-valerolactone is subjected to the ring-opening polymerization in a solvent to obtain poly-gamma-valerolactone; the biomimetic catalyst is one or a mixture of more of a thioureaamide type dihydrogen bond donor catalyst, an aminothiazole type dihydrogen bond donor catalyst and a phenyl phosphate type dihydrogen bond donor catalyst. Compared with a traditional catalyst, the aminothiazole type biomimetic catalyst, the thioureaamide type biomimetic catalyst and the phenyl phosphate type biomimetic catalyst have no metal and the utilization amount is small; the catalysis effect is higher under the action of a dihydrogen bond.

Description

technical field [0001] The invention belongs to the field of biomass polymer materials, in particular to a method for catalyzing ring-opening polymerization of γ-valerolactone by using a biomimetic catalyst. Background technique [0002] With the development of science and technology, polymer materials have spread all over people's daily life. Among them, polyvinyl chloride and polystyrene are difficult to degrade in nature, causing great pollution to the environment. Among them, polylactic acid, polyaliphatic lactone and Polyesters such as polycarbonate are a kind of biodegradable and bioabsorbable polymer materials, which are widely used in the biological and pharmaceutical industries. And after being mixed with other polymers, the degradability of the polymer material is greatly improved. This type of polyester, as a fully degradable and environmentally friendly material derived from renewable resources crops, has attracted extensive attention and research all over the w...

Claims

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Application Information

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IPC IPC(8): C08G63/87C08G63/08
CPCC08G63/08C08G63/823C08G63/87
Inventor 朱晨杰郭凯沈涛唐成伦应汉杰欧阳平凯
Owner NANJING UNIV OF TECH
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