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

Methods for preparing N-alkoxycarbonyl isothiocyanate and derivative thereof

A technology of alkoxycarbonyl isothiocyanate and its derivatives, which is applied in the field of preparation of isothiocyanate and its derivatives, can solve the problems of low reaction efficiency, difficulty in catalyst removal, high catalyst toxicity, etc., and achieve catalytic High efficiency, non-toxic catalyst, and less waste water generation

Active Publication Date: 2011-08-31
CENT SOUTH UNIV
View PDF6 Cites 14 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing catalysts have problems such as high catalyst toxicity, low reaction efficiency, and difficulty in removing the catalyst during the refining process.

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
  • Methods for preparing N-alkoxycarbonyl isothiocyanate and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The preparation of embodiment 1N-ethoxycarbonyl isothiocyanate

[0036]2.5 parts of N-(N', N'-dimethylaminopropyl) methylisobutylimine with a purity of 99% were dissolved in 200 parts of cyclohexane, and 45.3 parts of thiocyanic acid with a purity of 98.5% were added Sodium, the mixture was cooled to a temperature of 0°C to 5°C under stirring. 54.3 parts of ethyl chloroformate with a purity of 98.5% was added to the reaction mixture under stirring in this temperature range, and the reaction was stirred for 3 hours, and the reaction was completed. Add 100 parts of water to dissolve the precipitated sodium chloride generated by the reaction, and separate the liquid to remove the water phase. The oil phase was distilled off under reduced pressure to remove the solvent cyclohexane to obtain the desired N-ethoxycarbonyl isothiocyanate product. Analysis indicated a 98.4% product yield based on ethyl chloroformate.

Embodiment 2

[0037] The preparation of embodiment 2N-ethoxycarbonyl-O-ethylthiocarbonyl carbamate

[0038] The N-ethoxycarbonyl isothiocyanate product prepared according to Example 1 was added to 115 parts of ethanol while maintaining the temperature of the reaction mixture between about 25°C and about 45°C. The reaction mixture was then stirred at a temperature of about 40°C to 45°C for about 2 hours. The product obtained is an ethanol solution of N-ethoxycarbonyl-O-ethylthiocarbonylcarbamate. Analysis indicated a 95.6% product yield based on ethyl chloroformate.

Embodiment 3

[0039] The preparation of embodiment 3N-ethoxycarbonyl-O-isopropylthiocarbonyl carbamate (one pot method)

[0040] Add 28 parts of N-(N', N'-dimethylaminopropyl) cyclohexylimine with 98% purity to 453 parts of NaSCN with 98% purity in 1000 parts of acetone solution, then keep the temperature under stirring Between 10°C and about 25°C. 550 parts of 98.5% ethyl chloroformate were added to the reaction mixture at this temperature range with stirring. After the addition step, the reaction mixture was stirred at about 10°C to about 25°C for 4 hours to give N-ethoxycarbonyl isothiocyanate. Then maintain the reaction temperature between 10°C and 25°C, and add 491 parts of isopropanol under stirring. After the addition is complete, the reaction is continued with stirring for about 3 hours at a temperature of 45° C. to 55° C., and the reaction ends. The obtained mixture was washed with water, separated to remove the water phase, and the remaining acetone solvent was distilled off un...

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 invention discloses a method for preparing alkoxycarbonyl isothiocyanate, which comprises the following step of: reacting chloroformate with thiocyanate in an organic solvent by taking dialkyl amino alkyl imine Schiff base as a catalyst to generate N-alkoxycarbonyl isothiocyanate. The invention further provides a method for preparing an alkoxycarbonyl isothiocyanate derivative, which comprises the following steps of: reacting chloroformate with thiocyanate in the presence of an organic solvent and a catalytic amount of dialkyl amino alkyl imine Schiff base to generate an alkoxycarbonyl isothiocyanate intermediate product; and reacting the intermediate product with an alcohol, amine, thioalcohol or thiophenol compound to generate the alkoxycarbonyl isothiocyanate derivative. The methods disclosed by the invention have the advantages of catalyst nontoxicity, high catalysis efficiency, high product purity, small amount of waste water and the like.

Description

technical field [0001] The technical field to which the invention belongs is the preparation of isothiocyanate and derivatives thereof, and mainly relates to an improved method for preparing N-alkoxycarbonyl isothiocyanate and derivatives thereof. Background technique [0002] Isothiocyanate is an important fine chemical intermediate, which has a very wide range of applications in the fields of medicine, pesticides and mineral processing agents. Since R.E.Doran first synthesized N-ethoxycarbonyl isothiocyanate from ethyl chloroformate and lead thiocyanate in boiling toluene in 1896, it has been synthesized by the reaction of chloroformate and thiocyanate N-alkoxycarbonyl isothiocyanate has become the main method for preparing N-alkoxycarbonyl isothiocyanate and its derivatives. The catalyst is to improve the efficiency of the reaction process between chloroformate and thiocyanate The key to technology. [0003] U.S. Patent No. 4,659,853 discloses a reaction between halofor...

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
IPC IPC(8): C07C331/32C07C327/22C07C335/28B01J31/02
Inventor 钟宏刘广义何谋海王帅夏柳荫曹占芳袁露
Owner CENT SOUTH UNIV
Features
  • Generate Ideas
  • 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