Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Process for synthesizing 1-chlorine-2-methyl-4-acetoxy-2-butylene

A technology of acetoxy and synthetic methods, applied in the chemical field, can solve problems such as poor product content, poor product yield and content, and increased impurities, and achieve the effects of low cost, mild reaction system, high content and yield

Active Publication Date: 2008-09-24
ZHEJIANG MEDICINE CO LTD +1
View PDF3 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, after experimental verification, it was found that the yield and content of the product were very poor during the chlorohydrination reaction
[0014] Usually the chloroalcoholation reaction of olefin can lead chlorine in the calcium hydroxide aqueous suspension, utilizes the active hypochlorous acid of generation to directly carry out chlorohydrinization ((Encyclopedia of Chemical Engineering) Editorial Board, Encyclopedia of Chemical Industry, Chemical Industry Press, 1996 the first 1st edition, Vol.16, P719-729); but we found that the content of the obtained product was very poor after experimental verification, which may be due to the presence of free chlorine and other miscellaneous ions that caused the double bond of olefins to undergo side reactions such as dichloro addition , resulting in an increase in impurities

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Process for synthesizing 1-chlorine-2-methyl-4-acetoxy-2-butylene
  • Process for synthesizing 1-chlorine-2-methyl-4-acetoxy-2-butylene
  • Process for synthesizing 1-chlorine-2-methyl-4-acetoxy-2-butylene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Preparation of 1-chloro-2-hydroxyl-2-methyl-3-butene and 1-chloro-2-methyl-4-hydroxyl-2-butene mixture

[0033] Put a 500ml three-neck bottle equipped with a thermometer and a solid feeding port into an alcohol cooling bath; add 68g (1mol) of isoprene, 100ml of water and 0.5g of inhibitor hydroquinone; Add tetrachloroglycocuril (95% available chlorine) in batches from the feeding port, 56 g (0.2 mol) in total, and add in about 1 hour, then continue to insulate and stir for 1 hour, filter, wash the filter cake with 15 ml of water, and it is a loose white powder solid. The filtrates were combined and allowed to stand for separation. The organic layer was lower than 40°C to recover unreacted isoprene under reduced pressure to obtain 90 g of crude product. Gas phase analysis showed that the total content of the product was 92.5%, and the yield was 92.1%. It can be directly used in the next reaction; the water layer is 99.5 grams, and it will be used in the next rea...

Embodiment 2

[0034] Embodiment 2: material proportioning, operating temperature and aftertreatment are with embodiment 1, and difference is that reaction water is the waste water layer in embodiment 1, gets crude product 93g, gas phase analysis shows that product total content is 89.5%, yield 92.1%. The filter cake is a loose white powder solid, and the water layer is 98 grams.

Embodiment 3

[0035] Embodiment 3: material proportioning, operating temperature and aftertreatment are the same as embodiment 1, the difference is that the water for reaction is the waste water layer in embodiment 2, obtains crude product 94.5g, gas phase analysis shows that product total content is 90.5%, yield 94.6% .

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The present invention discloses a synthetic method of 1-chlorine-2-methyl-4-acetoxy-2-butene, an important intermediate for synthesizing V acetate. The existing method adopts chlorohydrin reaction to prepare the product and has the problems of poor yield rate and content. In the method, isoprene is used as the raw material for the chlorohydrin reaction so as to prepare the mixture of addition products of 1-chlorine-2-hydroxy-2-methyl-3-butene and 1-chlorine-2-methyl-4-hydroxy-2-butene. Under the influence of acid catalysis, the mixture reacts with acetic anhydride to prepare the 1-chlorine-2-methyl-4-acetoxy-2-butene. The method is characterized in that the chlorohydrin reaction is done in the reaction system that consists of tetrachloroglycine urea and water. The raw materials used in the method has high content of available chlorine and less heteroion; the reaction system is mild; the content and the yield of the product are high; the three-waste is greatly reduced; the cost is low; and the method has high industrial value.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to the synthesis of V A Synthetic method of 1-chloro-2-methyl-4-acetoxy-2-butene, an important intermediate of acetate. Background technique [0002] Vitamin A (V A ) and its derivatives are an important class of drugs, and the products of major companies in the world are marked with V A Acetate-based (Encyclopedia of Chemical Industry, Chemical Industry Press, first edition in 1996, Vol.16, P719-729). 4-Acetoxy-2-methyl-2-buten-1-aldehyde (MW142, referred to as five-carbon aldehyde) is a C characterized by Wittig reaction 15 +C 5 Route Synthesis V A Key intermediate of acetate (Tanaka, USP 5,424,478, Process for producing Vitamin A Derivatives, [P] 1995; Tanaka, et al., JP 06,329,623, Preparation of Vitamin A Derivatives, [P] 1994; Zutter, Ulrich, Ep 648,735, Preparation of an intermediate for Vitamin A acetate, [P] 1995; Wang Lanming, Beijing Medicine, New Synthetic Technology of Vi...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/145C07C67/08C07C29/64
Inventor 马文鑫沈润溥胡四平陈春峰代世荣
Owner ZHEJIANG MEDICINE CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com