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

Synthesis method of methoxyfenozide key intermediate-substituted methyl benzoyl chloride

A technology of methylbenzoyl chloride and methoxyfenozide, which is applied in the field of compound preparation, can solve the problems of difficult treatment of phosphorus-containing wastewater, equipment corrosion, large investment, etc., and achieves reduced discharge, mild reaction conditions, and safe elimination. hidden effect

Inactive Publication Date: 2012-07-18
HANGZHOU VOCATIONAL & TECHN COLLEGE
View PDF4 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present about 3, the preparation method of 5-dimethylbenzoyl chloride and 3-methoxy-2-methylbenzoyl chloride mainly uses sulfur oxychloride, phosphorus pentachloride, phosphorus oxychloride, phosgene, Acyl chloride reagents such as diphosgene are prepared by acid chlorination reaction, and a large amount of sulfur dioxide tail gas is released during the reaction process with thionyl chloride, as reported in the third issue of volume 21 of "Heilongjiang Medical Science" 3,4,5-Trimethoxy The synthesis and application of benzoyl chloride, "Chemical Engineer" 2007, No. 11, reported the preparation of 2,4,6-trimethylbenzoyl chloride, etc., using aluminum trichloride as the catalyst and thionyl chloride as the acid chloride React with chemical reagents; with phosphorus oxychloride, the product contains a large amount of by-product phosphoric acid, and phosphorus oxychloride as a chlorinated reagent severely corrodes equipment, a large amount of phosphorus-containing wastewater is difficult to handle, and the pollution problem is serious; There are serious safety hazards in gas and diphosgene, which require the equipment to be well sealed and equipped with a corresponding phosgene tail gas treatment system, which requires a large investment. The above-mentioned methods are not suitable for 3,5-dimethylbenzene due to their different defects. Industrial production of acid chloride and 3-methoxy-2-methylbenzoyl chloride

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
  • Synthesis method of methoxyfenozide key intermediate-substituted methyl benzoyl chloride
  • Synthesis method of methoxyfenozide key intermediate-substituted methyl benzoyl chloride
  • Synthesis method of methoxyfenozide key intermediate-substituted methyl benzoyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 The synthetic method of a methoxyfenozide key intermediate substituted toluyl chloride described in this example is 3,5-dimethylbenzoic acid and bis(trichloromethyl)carbonate in an organic Under the action of an amine catalyst, an acid chlorination reaction occurs in an organic solvent to obtain the corresponding substituted methylbenzoyl chloride. The operation process is: first dissolve the organic amine catalyst in the organic solvent, then add 3,5-dimethylbenzoic acid to dissolve, then slowly add the organic solvent solution dissolved with bis(trichloromethyl) carbonate, control The rate of addition keeps the temperature of the reaction solution within 20°C. After the addition is complete, heat the reaction solution to 50°C-150°C, keep it warm for 2-5 hours, and track and detect it by chromatography. After the reaction is complete, evaporate the solvent under reduced pressure and distill The corresponding substituted methylbenzoyl chloride was collected. ...

Embodiment 2

[0023] Example 2 The synthetic method of a kind of methoxyfenozide key intermediate substituted methylbenzoyl chloride described in this example, the amount ratio of the feed material described in it is 3,5-dimethylbenzoic acid: bis( Trichloromethyl) carbonate: catalyst is 1: 0.4: 0.2,3, the charging capacity of 5-dimethylbenzoic acid is 15g (0.1mol), and bis(trichloromethyl) carbonate charging capacity is 12g (0.04 mol), the catalyst is pyridine, and the consumption is 1.6g (0.02mol), and the organic solvent is toluene, and the consumption is 100ml, which is 5.8 times of the quality of 3,5-dimethylbenzoic acid. Reaction temperature is 100~110 ℃, other operation is the same as embodiment 1, obtains 3,5-dimethylbenzoyl chloride 14.5g, product yield 86%, purity (GC) 98.5%, boiling point 232~135 ℃.

Embodiment 3

[0024] Example 3 The synthetic method of a kind of methoxyfenozide key intermediate substituted toluoyl chloride described in this example, the amount ratio of the feed material described in it is 3,5-dimethylbenzoic acid: bis( Trichloromethyl) carbonate: catalyst is 1: 0.4: 0.05, the charging capacity of 3,5-dimethylbenzoic acid is 15g (0.1mol), and bis(trichloromethyl) carbonate charging capacity is 12g (0.04 mol), the catalyst is triethylamine, and the consumption is 0.5g (0.005mol), and the organic solvent is chlorobenzene, and the consumption is 100ml, which is 7.3 times of 3,5-dimethylbenzoic acid quality. Reaction temperature is 120~130 ℃, other operation is the same as embodiment 1, 3,5-dimethylbenzoyl chloride 14.7g, product yield 87.5%, purity (GC) 99%, boiling point 235~236 ℃.

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

PropertyMeasurementUnit
boiling pointaaaaaaaaaa
boiling pointaaaaaaaaaa
boiling pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses a synthesis method of methoxyfenozide key intermediate-substituted methyl benzoyl chloride. The corresponding substituted methyl benzoyl chloride is obtained by reacting 3,5-mesitylenic acid or 3-methoxyl-2-methyl benzoic acid with di(trichloromethyl)carbonic ester under the action of an organic amine catalyst in an organic solvent according to a chemical equation. The method has the advantages of mild reaction condition, safe and reliable operating process, high product yield, elimination of potential safety hazard from a process source, reduction in three waste generating sources, and high industrial implementation value.

Description

technical field [0001] The invention relates to a synthesis method of a key intermediate of methoxyfenozide substituted toluyl chloride, which belongs to the preparation method of compounds. Background technique [0002] Methoxyfenozide is a high-efficiency, low-toxic insect growth regulator belonging to diarylhydrazides. It is mainly used in vegetables and farmland crops to control Lepidoptera pests. It was successfully developed by Dow Chemical Company. As important intermediates of 3,5-dimethylbenzoyl chloride and 3-methoxy-2-methylbenzoyl chloride, how to adopt a clean and efficient synthesis method has attracted great attention. [0003] At present about 3, the preparation method of 5-dimethylbenzoyl chloride and 3-methoxy-2-methylbenzoyl chloride mainly uses sulfur oxychloride, phosphorus pentachloride, phosphorus oxychloride, phosgene, Acyl chloride reagents such as diphosgene are prepared by acid chlorination reaction, and a large amount of sulfur dioxide tail gas i...

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): C07C65/21C07C63/10C07C51/60
Inventor 童国通
Owner HANGZHOU VOCATIONAL & TECHN COLLEGE
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