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A kind of preparation method of 3,4-diacetoxy-1-butene

A technology of diacetoxy and butene, which is applied in the field of preparation of 3,4-diacetoxy-1-butene, can solve the problems of expensive catalyst, high catalyst consumption and low isomerization yield, etc. Achieve the effects of increased yield, simple and easy-to-obtain raw materials, and high yield

Active Publication Date: 2020-10-13
广州巨元生化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In this synthetic route, the rearrangement of 1,4-butenediol to 1,2-butenediol requires the use of catalysts, mercury sulfate and sulfuric acid, and the amount of catalyst is large, and mercury sulfate is a heavy metal reagent, which is not allowed in production. Use; acetylation can be reacted with acetyl chloride or acetic anhydride, acetyl chloride and acetic anhydride are limited reagents and expensive, which limits the industrialization of the process
[0010] In addition, in the rearrangement of 1,4-diacetoxy-2-butene to 3,4-diacetoxy-1-butene, it is reported that the catalyst palladium chloride is used, the catalyst is expensive, and the isomerization yield Low

Method used

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preparation example Construction

[0034] A kind of preparation method of 3,4-diacetoxy-1-butene, comprises the following steps:

[0035] Esterification step: In the presence of acid, 1,4-butenediol is esterified with acetic acid to obtain a solution containing 1,4-diacetoxy-2-butene and acetic acid, and the acetic acid is removed , to obtain 1,4-diacetoxy-2-butene;

[0036] Isomerization step: adding a cuprous catalyst to the 1,4-diacetoxy-2-butene obtained in the esterification step, heating for isomerization rearrangement reaction, and obtaining 3,4-diacetoxy Base-1-butene mixture;

[0037] Purification step: Purify the mixed liquid obtained in the isomerization step to obtain 3,4-diacetoxy-1-butene.

[0038] The specific reaction formula is as follows:

[0039]

[0040] As a preferred embodiment, the specific operating steps of the esterification step are as follows:

[0041] Esterification step 1) adding acetic acid and sulfuric acid, or adding acetic acid and p-toluenesulfonic acid to the reaction ...

Embodiment 1

[0051] A kind of preparation method of 3,4-diacetoxy-1-butene, comprises the following steps:

[0052] Esterification step: add acetic acid and p-toluenesulfonic acid to the reaction vessel; stir to disperse, then add 1,4-butenediol dropwise, and stir for esterification; the molar ratio of acetic acid to 1,4-butenediol is 5:1;. The conditions for the reaction of acetic acid and 1,4-butenediol are as follows: the reaction temperature is 20° C., and the reaction time is 1.0 h. When the reaction generates water, remove the generated water so that the reaction proceeds in the positive direction; after the reaction is completed, remove the acetic acid in the reaction solution to obtain 1,4-diacetoxy-2-butene; specifically, remove The method of the water generated by the reaction is the vacuum distillation water separation method.

[0053]Isomerization step: adding a cuprous catalyst to the 1,4-diacetoxy-2-butene obtained in the esterification step, heating for isomerization rearr...

Embodiment 2

[0057] A kind of preparation method of 3,4-diacetoxy-1-butene, comprises the following steps:

[0058] Esterification step: add acetic acid and sulfuric acid, or add acetic acid and p-toluenesulfonic acid to the reaction vessel; stir and disperse, then add 1,4-butenediol dropwise, and stir for esterification reaction; acetic acid and 1,4-butene The molar ratio of enediol is 2:1; the conditions for the reaction of acetic acid and 1,4-butenediol are: the reaction temperature is 110°C, and the reaction time is 5h. When the reaction generates water, remove the generated water so that the reaction proceeds in the positive direction; after the reaction is completed, remove the acetic acid in the reaction solution to obtain 1,4-diacetoxy-2-butene; specifically, remove The method of the water generated by the reaction is the atmospheric pressure distillation method.

[0059] Isomerization step: adding a cuprous catalyst to the 1,4-diacetoxy-2-butene obtained in the esterification ste...

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Abstract

The invention discloses a preparation method of 3,4-diacetoxy-1-butene. The preparation method comprises steps as follows: an esterification step: 1,4-butylene glycol and acetic acid are subjected to an esterification reaction in the presence of acid, a solution containing 1,4-diacetoxy-2-butene and acetic acid is obtained, acetic acid is removed and 1,4-diacetoxy-2-butene is obtained; an isomerization step: cuprous catalysts are added to 1,4-diacetoxy-2-butene obtained in the esterification step, the mixture is heated for an isomerization rearrangement reaction, and a mixed solution containing 3,4-diacetoxy-1-butene is obtained; a purification step: the mixed solution obtained in the isomerization step is purified, and 3,4-diacetoxy-1-butene is obtained. The preparation method adopts easy-to-realize reaction conditions and has the characteristic of high yield.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a preparation method of 3,4-diacetoxy-1-butene. Background technique [0002] 3,4-diacetoxy-1-butene is widely used as an important intermediate in the preparation of medicines, feed additives, food additives, etc. An important intermediate of acetate, and 3-methyl-4-oxo-2-buten-1-yl acetate is the synthesis of vitamin A acetate, apo-8'-carotaldehyde, citrinin, apo - an important intermediate of ethyl 8'-carotate; in addition, 3,4-diacetoxy-1-butene can also be used in lithium batteries, food packaging materials, etc. Therefore, research on the synthesis method of 3,4-diacetoxy-1-butene has important industrial application value. [0003] Among them, the chemical structural formula of 3,4-diacetoxy-1-butene is shown in formula (I) [0004] [0005] At present, there are very limited reports on the preparation of 3,4-diacetoxy-1-butene, and there are various defects...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/293C07C69/16
CPCC07C67/08C07C67/293C07C69/16
Inventor 廖艳金姚伟平麦凌志方泽华区家杰李建喜
Owner 广州巨元生化有限公司
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