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Preparation method of methyl-3-pentenoate

A technology of methyl pentenoate and valerolactone is applied in the field of preparation of unsaturated carboxylic acid esters, can solve problems such as difficulty in isomer separation, avoid expensive price, high yield, and reduce the generation of isomers Effect

Inactive Publication Date: 2012-11-21
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method uses renewable biomass-sourced γ-valerolactone and methanol as raw materials to obtain a mixture of methyl pentenoate at a higher temperature (200-250°C) and a longer reaction time (40h). But it contains more isomers (25-35% of 4-pentenoic acid methyl ester and 1-5% of 2-pentenoic acid methyl ester), because the physical and chemical properties of the isomers are extremely close, so Cause the difficulty of isomer in separation, therefore, improve the selectivity of 3-pentenoic acid methyl ester, reduce the generation of isomer to the greatest extent is a technical problem that needs to be solved

Method used

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  • Preparation method of methyl-3-pentenoate
  • Preparation method of methyl-3-pentenoate
  • Preparation method of methyl-3-pentenoate

Examples

Experimental program
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Effect test

Embodiment 1

[0061] Add a stirring bar, γ-valerolactone (10.01g, 0.1mol) and sulfuric acid (98%, 0.036g, 0.36mmol) into a 25mL two-necked round-bottomed flask, install a rectification column, a nitrogen gas introduction device, and stir in a nitrogen atmosphere Raise the temperature to 170°C, add methanol into the reaction flask through a syringe at a flow rate of 10mL / h, and react for 3.5h. The mixture of methanol and products is distilled from the top of the tower, and the fractions at 70-90°C are collected and analyzed by GC, GC-MS internal standard The content of the target product 3-pentenoic acid methyl ester was determined by the method, which contained 3-pentenoic acid methyl ester 10.84g, the yield was 95%, and the selectivity was 98%.

Embodiment 2

[0063] Add a stirring bar, γ-valerolactone (10.01g, 0.1mol) and trifluoromethanesulfonic acid (98%, 0.055g, 0.36mmol) into a 25mL two-necked round-bottomed flask, install a rectification tower, and a nitrogen gas introduction device. Stir in a nitrogen atmosphere and heat up to 190°C. Methanol is added into the reaction flask through a syringe at a flow rate of 10mL / h. After 5 hours of reaction, the mixture of methanol and products is distilled from the top of the tower. MS internal standard method was used to determine the content of the target product, methyl 3-pentenoate, which contained 10.73 g of methyl 3-pentenoate, with a yield of 94% and a selectivity of 94%.

Embodiment 3

[0065] Add a stirrer, γ-valerolactone (10.01g, 0.1mol) and phosphotungstic acid (0.290g, 0.1mmol) into a 25mL two-necked round bottom flask, install a rectification tower and a nitrogen gas introduction device, stir and raise the temperature in a nitrogen atmosphere To 250°C, add methanol into the reaction flask through a syringe at a flow rate of 10mL / h, react for 8h, the mixture of methanol and product is distilled from the top of the tower, collect the fraction at 70-90°C, and measure it by GC, GC-MS internal standard method The content of target product 3-pentenoic acid methyl ester, wherein contains 3-pentenoic acid methyl ester 9.12g, productive rate 80%, selectivity 86%.

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Abstract

The invention discloses a preparation method of methyl-3-pentenoate. According to the invention, gamma-valerolactone and methanol which are adopted as initial raw materials undergo ester change and a dehydration reaction under the action of a catalyst to obtain methyl-3-pentenoate, and simultaneously the obtained methyl-3-pentenoate is separated through distillation. The method provided by the invention has the advantages of high reaction selectivity, simple technology, simple operation, and environmental protection, and the highest yield and the highest selectivity of the methyl-3-pentenoate reach 95% and 98% respectively.

Description

technical field [0001] The invention relates to the preparation of unsaturated carboxylic acid esters, in particular to a preparation method of methyl 3-pentenoate. Background technique [0002] Methyl 3-pentenoate is an important intermediate for the preparation of adipic acid, caprolactone, caprolactam and their polymers and copolymers such as polyamide-6 and polyamide-66 in the nylon industry. At present, the most important method for preparing methyl 3-pentenoate is carboxyesterification of 1,3-butadiene, such as Royal DSM Group (DSM), Royal Shell Petroleum Group (Shell), DuPont and Germany BASF and other chemical giants use 1,3-butadiene as the starting material to develop a new green synthesis process for the production of caprolactam, and have made some progress. Among them, the most promising one is the Altam route jointly developed by Shell and DSM. The first step is to use 1,3-butadiene, CO and methanol as raw materials for carboxyesterification to prepare methyl ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/533C07C67/03
Inventor 廖兵曾繁馨邓理郭庆祥刘海峰刘军魏续瑞
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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