Unlock instant, AI-driven research and patent intelligence for your innovation.

Process for preparing 2E,4E,3,7,11-trimethyl-2,4,10-dodecatrienoic ester

A dodecatrienoate and trimethyl technology, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., can solve problems such as poor selectivity of trans double bonds

Active Publication Date: 2007-04-11
CHINA TOBACCO HUNAN INDAL CORP
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 3,7,11-Trimethyl-2,4,10-Dodecatrienoate is an intermediate for the preparation of insect growth regulator-methoprene and its derivatives, currently known as 3-hydroxy-3,7 , 11-trimethyl-4,10-dodecadienoic acid ester is used as raw material and dehydrated with conventional organic acid to obtain 3,7,11-trimethyl-2,4,10-dodecatriene A mixture of four double-bond isomers of acid esters, in which the ratio of the target product 2E, 4E-3,7,11-trimethyl-2,4,10-dodecatrienoate in the product is only 25 % or so, double bond isomerization occurs during the dehydration reaction, and the selectivity to generate trans double bonds is poor

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 preparing 2E,4E,3,7,11-trimethyl-2,4,10-dodecatrienoic ester
  • Process for preparing 2E,4E,3,7,11-trimethyl-2,4,10-dodecatrienoic ester
  • Process for preparing 2E,4E,3,7,11-trimethyl-2,4,10-dodecatrienoic ester

Examples

Experimental program
Comparison scheme
Effect test

reference example 1

[0034] Preparation of raw material 3,7,11-trimethyl-2,4,10-dodecatrienoic acid isopropyl ester

[0035] Into a 250 ml round bottom flask was added 13 g of a homemade sample of isopropyl 3-hydroxy-3,7,11-trimethyl-4,10-dodecadienoate, 100 ml of benzene and 0.26 g of p-toluenesulfonic acid, Stir the reaction at 60°C for 4.5 hours, wash the reaction solution with saturated aqueous sodium bicarbonate solution until weakly alkaline, then wash twice with saturated brine, dry over anhydrous sodium sulfate, evaporate benzene to obtain 3,7,11-trimethyl 12.1 g of isomer mixture of isopropyl-2,4,10-dodecatrienoate, yield 72%. According to the GC-MS results, the content of isopropyl 2E, 4E-3, 7, 11-trimethyl-2, 4, 10-dodecatrienoate is about 25%. The sample was subjected to silica gel column chromatography with 100:1 petroleum ether:ethyl acetate as the eluent to obtain 2Z,4E-3,7,11-trimethyl-2,4,10-dodecatriene 0.20 gram of isopropyl ester, its GC-MS result is shown in Fig. 1. 0.30 g ...

reference example 2

[0043] Preparation of raw material 3,7,11-trimethyl-2,4,10-dodecatrienoic acid ethyl ester

[0044] Similar to the above preparation of 3,7,11-trimethyl-2,4,10-dodecatrienoic acid isopropyl ester, 3-hydroxy-3,7,11-trimethyl-4,10- Isopropyl dodecadienoate is replaced by ethyl 3-hydroxy-3,7,11-trimethyl-4,10-dodecadienoate to give 3,7,11-trimethyl-2 , 12.0 g of 4,10-ethyl dodecatrienoic acid isomer mixture, yield 70%. GC-MS results showed that the content of ethyl 2E,4E-3,7,11-trimethyl-2,4,10-dodecatrienoate was about 27%. The sample was subjected to silica gel column chromatography with 100:1 petroleum ether:ethyl acetate as the eluent to obtain 2Z,4E-3,7,11-trimethyl-2,4,10-dodecatriene Ester 0.2 gram, its GC-MS result is shown in Figure 3. 0.20 g of 2E,4E-3,7,11-trimethyl-2,4,10-dodecatrienoate was obtained, and the GC-MS results are shown in FIG. 4 . Obtain 4.1 grams of 3,7,11-trimethyl-2,4,10-dodecatrienoic acid ethyl ester isomer mixture, and its GC results are shown ...

Embodiment 1

[0052] Add 2 grams of 3,7,11-trimethyl-2,4,10-dodecatrienoic acid isopropyl isomer mixture in Reference Example 1 and 0.02 gram of thiophenol into a 100ml single-necked bottle , heated to 100°C in nitrogen, stirred for 1 hour, and then distilled off thiophenol under reduced pressure. Obtain 2 gram samples, its GC result is shown in Figure 6, wherein 2E, 4E-3,7,11-trimethyl-2,4,10-dodecatrienoic acid isopropyl ester content is 50.7%, 2Z, 4E - Isopropyl 3,7,11-trimethyl-2,4,10-dodecatrienoate content of 26.5%.

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 process of preparing 2E, 4E-3, 7, 11-trimethyl-2, 4, 10-dodecatrienoic ester with 3, 7, 11- trimethyl-2, 4, 10-dodecatrienoic ester. During the preparation, 3, 7, 11- trimethyl-2, 4, 10-dodecatrienoic ester is made to react with catalyst phenyl thiophenol or the catalyst mixture of phenyl thiophenol and 2, 2'-azo diisobutyronitrile.

Description

technical field [0001] The invention relates to a method for preparing 2E, 4E-3, 7, 11-trimethyl-2, 4, 10-dodecatrienoate. Background technique [0002] 3,7,11-trimethyl-2,4,10-dodecatrienoate is an intermediate for the preparation of insect growth regulator-methoprene and its derivatives, currently known as 3-hydroxy-3,7 , 11-trimethyl-4,10-dodecadienoic acid ester is used as raw material and dehydrated with conventional organic acid to obtain 3,7,11-trimethyl-2,4,10-dodecatriene A mixture of four double-bond isomers of acid esters, in which the ratio of the target product 2E, 4E-3,7,11-trimethyl-2,4,10-dodecatrienoate in the product is only 25 % or so, double bond isomerization occurs during the dehydration reaction, and the selectivity of generating trans double bonds is poor. Contents of the invention [0003] The purpose of this invention is to provide a kind of method for preparing 2E, 4E-3,7,11-trimethyl-2,4,10-dodecatrienoate, this method has overcome the above-m...

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): C07C69/587B01J31/02
Inventor 周容刘建福苏利霞杨华武银董红
Owner CHINA TOBACCO HUNAN INDAL CORP
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com