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Method for synthesizing carbamic acid ester without phosgene in ionic liquid

A technology of carbamate and alkyl carbamate, which is applied in the field of non-phosgene synthesis of carbamate in ionic liquid, can solve the problems of no room temperature ionic liquid and few research reports, and achieves good reusability, The effect of simple product composition and easy separation

Inactive Publication Date: 2010-06-16
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although patents such as US-4278805, EP-A-28338, US-4375000, EP-0018588, and WO-9717323 have also introduced methods for preparing some aromatic or aliphatic carbamates from alkyl carbamate

Method used

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  • Method for synthesizing carbamic acid ester without phosgene in ionic liquid
  • Method for synthesizing carbamic acid ester without phosgene in ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-4

[0038] In a 120ml reaction kettle equipped with electromagnetic stirring and automatic temperature control system, add 4mmol of hexamethylenediamine, 16mmol of butyl carbamate, 3.7ml of n-butanol, 0.16g of dihydrogen phosphate 1-methyl- 3-Butylimidazolium ionic liquid, after airtight, replace the air in the kettle with nitrogen. After raising the temperature to 200°C for 4 hours, the reactor was cooled to room temperature to release residual gas, and the insoluble matter was separated by filtration, and the butanol in the filtrate was distilled off. Add 50ml of distilled water to the remaining solid, stir well, and precipitate a white solid target product. After drying and weighing, calculate the separation yield according to the amount of hexamethylenediamine added. Results: The conversion rate of hexamethylenediamine was 100%, and the separation yield of butylhexamethylenedicarbamate was 92%.

[0039] The dihydrogen phosphate 1-methyl-3-butylimidazolium ionic liquid was re...

Embodiment 5

[0043] In a 120ml reaction kettle equipped with electromagnetic stirring and automatic temperature control system, add 4mmol of hexamethylenediamine, 16mmol of butyl carbamate, 3.7ml of n-butanol, 0.16g of perchlorate 1-methyl-3 - Butylimidazole ionic liquid, after airtight, replace the air in the kettle with nitrogen. After raising the temperature to 200°C for 4 hours, cool the reaction vessel to room temperature, release residual gas, separate the catalyst and insoluble matter through centrifugation and filtration, and distill off the butanol in the filtrate. Add 50ml of distilled water to the remaining solid, stir well, and precipitate a white solid target product. After drying and weighing, calculate the separation yield according to the amount of hexamethylenediamine added. Results: The conversion rate of hexamethylenediamine was 100%, and the separation yield of butylhexamethylenedicarbamate was 91%.

Embodiment 6

[0045]In a 120ml reaction kettle equipped with electromagnetic stirring and automatic temperature control system, add 4mmol of hexamethylenediamine, 16mmol of ethyl carbamate, 2.2ml of ethanol, 0.11g of dihydrogen phosphate 1-methyl-3- Butylimidazole ionic liquid, after airtight, replace the air in the kettle with nitrogen. After raising the temperature to 200°C for 4 hours, cool the reactor to room temperature, release residual gas, separate the catalyst and insoluble matter through centrifugation and filtration, and distill off the ethanol in the filtrate. Add 50ml of distilled water to the remaining solid, stir well, and precipitate a white solid target product. After drying and weighing, calculate the separation yield according to the amount of hexamethylenediamine added. Results: The conversion rate of hexamethylenediamine was 100%, and the separation yield of ethylhexamethylenedicarbamate was 46%.

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Abstract

The invention discloses a method for synthesizing carbamic acid ester without phosgene in ionic liquid. In the method, dialkyl imidazoles ionic liquid is taken as catalyst and reaction medium, amine compound and carbamic acid alkyl ester carbonyl are compounded into corresponding carbamic acid ester by carbonylation in proper solvent at certain reaction temperature and reaction time. The method is mainly characterized in that the catalyst system is simple, no other catalysts are added in except for ionic liquid, and the ionic liquid can be recycled; the product is precipitated in crystal form which is easy to separate; the operation process is simple and safe, belongs to environment-friendly production process, provides a new approach for synthesizing isocyanate in green way, and has certain practical application prospect.

Description

technical field [0001] The invention relates to a method for synthesizing carbamate without phosgene in an ionic liquid, in particular to a method for synthesizing a corresponding carbamate by oxolation of an amine compound and an alkyl carbamate under the environment of an ionic liquid method. Background technique [0002] Carbamate is a very important organic synthesis intermediate, which is not only widely used in the manufacture of agricultural pesticides, herbicides and drug synthesis, but also can be used as an important precursor for non-phosgene synthesis of polyurethane in industry. The foamed plastics, coatings, adhesives, synthetic leather, elastic fibers, etc. and their products are widely used in the fields of construction, transportation, mining, machinery, printing, light industry and agriculture. So far, there have been many synthetic processes related to carbamate, such as the reaction of carbamoyl chloride and alcohol in the early stage, and the reaction o...

Claims

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Application Information

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IPC IPC(8): C07C269/00C07C271/20C07C271/08B01J31/02
CPCY02P20/54
Inventor 邓友全张宏哲张庆华郭晓光马昱博
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI