Method of preparing 3,3-dimethyl-4-pentenoic acid methyl ester with industrial scale

An industrial-scale technology of methyl bentitate, which is applied in the field of carbocyclic compound preparation, can solve the problems of no solid catalyst and pressurized reaction, and achieve the effects of less "three wastes" emission, simple process, and shortened reaction time

Inactive Publication Date: 2007-02-07
YINGKOU YINGXIN CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] So far, there is no method report using solid catalyst and pressurized reaction

Method used

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  • Method of preparing 3,3-dimethyl-4-pentenoic acid methyl ester with industrial scale
  • Method of preparing 3,3-dimethyl-4-pentenoic acid methyl ester with industrial scale

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Molar ratio: isopentenol: trimethyl orthoacetate: catalyst = 1: 1.2: 0.05

[0024] Raw materials: (all adopt commercially available industrial specifications)

[0025] Commercially available prenyl alcohol (Prenyl alcohol, chemical name 3-methyl-2-buten-1-ol 3-methyl-2-buten-1-ol) 86.9kg (content 99%, pure 86.031kg 1gkmol )

[0026] Commercially available trimethyl orthoacetate (Trimethyl orthoacetate, chemical name: 1.1.1-trimethoxyethane, 1.1.1-Trimethoxyethane) 145.5kg (content 99%, pure 144.05kg 1.2kgmol)

[0027] Catalyst anhydrous zinc chloride 6.8kg (content 98%, pure 6.664kg, 0.05kgmol)

[0028] operate:

[0029] Put the raw materials and catalysts into the autoclave, heat, and react for 6-7 hours at 150-160°C and a pressure of 2.5Mpa in the autoclave; after the reaction is completed, cool down to room temperature, and the pressure in the autoclave will naturally drop to normal pressure; the vacuum sucks out the material, and the reaction material is filtered...

Embodiment 2

[0031] Molar ratio: isopentenol: trimethyl orthoacetate: catalyst = 1: 1.5: 0.03

[0032] Prenol 86.9kg (content 99%, pure 86.031kg 1kgmol) and trimethyl orthoacetate 181.8kg (content 99%, pure 179.98kg 1.5kgmol), catalyst nickel sulfate 7.7kg (content 98%, pure 7.55kg, 0.03kgmol) in an autoclave at 190-200°C, 3.0MPa, react for 8-9h, and observe that the pressure no longer increases as the end point of the reaction. The rectification operation was the same as that in Example 1, and finally the product methyl bentinate was 126kg, and the content determined by gas chromatography was 99.26%, which was 125.07kg pure, and the yield was 88.08%.

Embodiment 3

[0034] Molar ratio: isopentenol: trimethyl orthoacetate: catalyst = 1: 1.2: 0.02

[0035] Prenol 86.9kg (content 99%, pure 86kg 1kgmol) and trimethyl orthoacetate 145.5kg (content 99%, pure 144.05kg 1.2kgmol), catalyst nickel acetate 5.3kg (content 98%, pure 5.19 kg, 0.02kgmol) into the autoclave, 160~170°C, 2.5MPa, react for 9~10h, observe the end of the reaction after the pressure no longer increases. The rectification operation was the same as that in Example 1, and finally the product methyl bentinate was 122kg, and the content determined by gas chromatography was 99.43%, which was 121.31kg pure, and the yield was 85.43%. All the other are with embodiment 1.

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Abstract

The invention belongs to the industrial scale production methods for methyl pentenoate, involving a synthesis method for methyl pantenate through a reaction of isopentenol with methyl orthoacetate through catalytic synthesis under pressure. The molar ratio of isopentenol : methyl orthoacetate : catalyst is 1:1.0~2.0 : 0.01~0.1. The reaction conditions include stirring pressure of 1~3.2MPa and temperature of 150~250DEG C, and the reaction time of 6~10h. The catalysts are removed after cooling and the final product is obtained by distilling the filtrate. The catalyst is solid anhydrous zinc chloride, nickel sulfate, nickel acetate, copper acetate, anhydrous cupric chloride, or anhydrous ferric chloride. The invention has the advantages of simple catalyst separation as using solid catalyst, short reaction time as reacting at high temperature and pressure, high yield of 88%, low production cost, high product content above 99%, simple process, and less wastes.

Description

technical field [0001] The invention belongs to the preparation of carbocyclic compounds, and in particular relates to a method for synthesizing methyl pyretinate by using prenyl alcohol and trimethyl orthoacetate under catalysis and pressure. Background technique [0002] Methyl pentenoic acid (4-Pentenoic acid, 3,3-dimethyl-, methyl ester), chemical name: 3,3-dimethyl-4-pentenoic acid methyl ester (3,3-Dimethyl-4-pentenoic acid acid methyl ester); Molecular formula C 8 h 14 o 2 ;Structural formula: [0003] [0004] Methyl bentinate is an important organic chemical raw material. It is an intermediate in the manufacture of the three major pyrethroid pesticides of fluorine, chlorine and bromine. It can also manufacture a variety of chemicals. It was first industrialized by the British Zeneca in the early 1970s Production, domestic production has also occurred in recent years, but most of them belong to the category of imitation. [0005] Literature "Synthetic Researc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/587C07C67/03
Inventor 高庆昌
Owner YINGKOU YINGXIN CHEM TECH CO LTD
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