Method for synthesizing diamino formic ether

A technology of diurethane and carbamate, which is applied in the field of catalyzing carbamate and alkyl or aryl diamine to synthesize corresponding dicarbamate, which can solve unfavorable industrial scale-up, high reaction temperature, side effects There are many products, etc., to achieve the effect of good reusability, good economy, and easy separation and recovery

Inactive Publication Date: 2009-07-01
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

Disadvantages: higher reaction temperature, higher cost of organic zirconium salt catalyst, more by-products
In US-A-5386053, carbonic acid derivatives and alcohols are used

Method used

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  • Method for synthesizing diamino formic ether
  • Method for synthesizing diamino formic ether
  • Method for synthesizing diamino formic ether

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0031] Example 1

[0032] In a 2L autoclave, add 174.5g butyl carbamate (BC) and 58g 1,6-hexamethylenediamine (HDA), add Zn(OAc) 2 3 g, the solvent is butanol, and the reaction is completed after 5 hours at 180° C., the reaction pressure is 1.5 MPa, and 500 rpm. After the product was cooled to room temperature, samples were taken to obtain sample 1 of a colorless clear liquid and part of the catalyst, and part of the catalyst was recovered by filtration. Take 1-2ml sample 1 and dissolve it in 2-3ml chloroform for chromatographic analysis. Then at 80°C and 100mmHg, the butanol in sample 1 was recovered by distillation, and the residue after distillation was cooled to room temperature and 200ml of ether was added to obtain the target product 1,6-butyl-hexanedicarbamate (BHDC), part of the catalyst, The monoester (hexamethylene-1-amino-6-carbamate butyl) and a small amount of butylated product were precipitated, and then subjected to suction filtration to obtain a mixture of B...

Example Embodiment

[0034] Example 2

[0035]In a 2L autoclave, add 174.5g butyl carbamate (BC) and 100g 4,4-diphenylmethanediamine (MDA), add Pb(OAc) 2 3 g, the solvent is butanol, and the reaction is completed after 6 hours at 280° C., the reaction pressure is 1.5 MPa, and 450 rpm. After the product was cooled to room temperature, samples were taken to obtain a light yellow clear liquid and a sample 1 of a part of the catalyst, and part of the catalyst was recovered by filtration. Take 1-2ml sample 1 and dissolve it in 2-3ml chloroform for chromatographic analysis. Then at 80°C, under 100mmHg, the butanol in sample 1 was recovered by distillation, and the residue after the distillation was cooled to room temperature and 200ml of ether was added to obtain the target product 4,4-diphenylmethanedicarbamate butyl ester (BMDC), Part of the catalyst, monoester (butyl diphenylmethane-4-amino-4-carbamate) and a small amount of butylated product were precipitated, and then suction filtration was perf...

Example Embodiment

[0036] Example 3

[0037] In a 2L autoclave, add 225g methyl carbamate (MC) and 122g 2,6-toluenediamine (MDA), add SnCl 2 3 g, the solvent is methanol, at 160° C., the reaction pressure is 1.5 MPa and 600 rpm, the reaction is completed after 5 hours. After the product was cooled to room temperature, samples were taken to obtain sample 1 of a colorless clear liquid and part of the catalyst, and part of the catalyst was recovered by filtration. Take 1-2ml sample 1 and dissolve it in 2-3ml chloroform for chromatographic analysis. Then, at 40°C and 100mmHg, the methanol in sample 1 was recovered by distillation, and the residue after distillation was cooled to room temperature and 200ml of ether was added to obtain the target product 2,6-toluene dicarbamate (MTDC), part of the catalyst, mono Esters (methyl toluene-2 / 6-amino-6 / 2-carbamate) and a small amount of methylated products were precipitated, and then filtered with suction to obtain a mixture of MTDC, part of the catalyst...

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Abstract

The invention discloses a method for synthesizing diurethane. The method is to take carbamate and alkyl or aryl diamine as reactant and an organic solvent as a reaction medium, control the reaction temperature to be between 80 and 300 DEG C and the reaction pressure to be between 1.0 and 2.0 MPa, and catalyze and synthesize the diurethane, wherein the catalyst is one or two selected from Zn(OAc)2, Pb(OAc)2, SnCl2, NiO,SnO2 and ZnO. The method mainly has the characteristics of mild reaction conditions, cheap and easily obtained catalyst, good reusability, easy reclaiming and separation, good economical efficiency of the carbamate raw material, high purity of products, small number of byproducts, and high industrial application value.

Description

technical field [0001] The invention relates to a method for synthesizing diurethanes, in particular to a method for synthesizing corresponding diurethanes from carbamates and alkyl or aryl diamines. Background technique [0002] Alkyl carbamates are useful intermediates in the preparation of various chemical products, such as herbicides, insecticides, etc. As an intermediate in organic synthesis, methyl carbamate can be used to synthesize melamine derivatives and polyvinylamine. Methyl carbamate can also react with unsaturated hydrocarbons, aldehydes, ketones, polyols and aromatic rings to generate various derivatives. Because methyl carbamate has the characteristics of odorlessness, moderate volatility, low toxicity, and good moth-proof effect, it can replace naphthalene and camphor as a moth-proof agent for clothing. Urethane can be used to synthesize dialkyl alkyl glycol formate, a promising tranquilizer. Butyl carbamate can react with formaldehyde to generate methylo...

Claims

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Application Information

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IPC IPC(8): C07C271/20C07C271/24C07C271/26C07C269/06
Inventor 邓友全郭晓光尚建鹏马昱博马祥元张宏哲
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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