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Method for synthesizing hexamethylene 1,6-diamino methyl formate

A technology of methyl dicarbamate and hexamethylene, applied in the field of hexamethylene-1, can solve the problems of harsh reaction conditions, serious pollution, complicated process, etc., and achieves short reaction time, high yield and selectivity , the effect of cheap and easy-to-obtain raw materials

Inactive Publication Date: 2006-02-01
CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to solve the problems of complex process, harsh reaction conditions and serious pollution in the prior art, the present invention provides a hexamethylene-1,6 -The synthetic method of methyl dicarbamate

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] A 250ml three-neck round bottom flask was heated in an oil bath with a constant temperature tank and magnetically stirred. 10.0g of 1,6-hexamethylenediamine, 21.0g of dimethyl carbonate, and 2.0g of lead oxide were added to the flask. After the addition, the reaction was carried out at 120° C. for 5 hours, and the by-product methanol was continuously separated during the reaction.

[0023] After the reaction, the catalyst was filtered off, the solvent was distilled off under reduced pressure, and crystallized to obtain a white solid of methyl hexamethylene-1,6-dicarbamate with a yield of 48%.

Embodiment 2

[0025] A 250ml three-necked round-bottomed flask was heated in an oil bath with a constant temperature tank and magnetically stirred. 15.0g of 1,6-hexamethylenediamine, 39.0g of dimethyl carbonate, and 4.3g of lead nitrate were added to the flask. After the addition, the reaction was carried out at 150° C. for 4 hours, and the by-product methanol was continuously separated during the reaction.

[0026] After the reaction was finished, the catalyst was filtered off, the solvent was distilled off under reduced pressure, and crystallized, the obtained white solid was methyl hexamethylene-1,6-dicarbamate, the yield was 95%, and the selectivity was 98%.

Embodiment 3

[0028] A 250ml three-neck round bottom flask was heated in an oil bath with a constant temperature bath and magnetically stirred. 10.0g of 1,6-hexamethylenediamine, 21.0g of dimethyl carbonate, and 2.3g of lead acetate were added to the flask. After the addition, the reaction was carried out at 150° C. for 3 hours, and the by-product methanol was continuously separated during the reaction.

[0029] After the reaction was finished, the catalyst was filtered off, the solvent was distilled off under reduced pressure, and crystallized, the obtained white solid was methyl hexamethylene-1,6-dicarbamate, with a yield of 98% and a selectivity of 99%.

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Abstract

A process for synthesizing hexamethylene-1,6-methyl diaminoformate features the ordinary-pressure catalytic reaction between 1,6-hexanediamine and dimethyl carbonate under the action of Pb catalyst. Its advantages are high output rate up to 98% and high selectivity.

Description

technical field [0001] The invention belongs to a synthesis method of methyl hexamethylene-1,6-dicarbamate, in particular to a method for using 1,6-hexamethylenediamine (also known as hexamethylenediamine, referred to as HDA) and carbonic acid Dimethyl ester (abbreviated as DMC) reacts under the catalysis of lead compounds to generate hexamethylene-1,6-dicarbamate methyl ester. Background technique [0002] Methyl hexamethylene-1,6-dicarbamate is an intermediate for the clean production of hexamethylene-1,6-diisocyanate (referred to as HDI). HDI is an aliphatic isocyanate widely used in the polyurethane industry. Polyurethane coatings made of HDI have the characteristics of no yellowing, color retention, gloss retention, chalking resistance, oil resistance, and abrasion resistance, which are inferior to aromatic polyurethane coatings. . HDI can also be used to produce elastomers, adhesives, textile finishing agents, etc., and has a wide range of ...

Claims

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Application Information

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IPC IPC(8): C07C271/06C07C269/04
Inventor 王公应程杰姚洁
Owner CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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