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Method for the production of amines from compounds comprising carbodiimide groups, by hydrolysis with water

A carbodiimide group and carbodiimide technology, which is applied in the preparation of amino compounds, organic compounds, chemical instruments and methods, etc., can solve problems such as the transformation of compounds that have not yet seen carbodiimide groups

Inactive Publication Date: 2006-12-13
DEGUSSA AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] So far, no direct conversion of compounds wi

Method used

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  • Method for the production of amines from compounds comprising carbodiimide groups, by hydrolysis with water
  • Method for the production of amines from compounds comprising carbodiimide groups, by hydrolysis with water
  • Method for the production of amines from compounds comprising carbodiimide groups, by hydrolysis with water

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0020] Conversion of Dicyclohexylcarbodiimide to Cyclohexylamine

[0021] 500g of dicyclohexylcarbodiimide was heated to 190°C in an autoclave. Subsequently, 900 g of water were added with stirring from a storage tank heated to 190°C. The reaction mixture builds up vapor pressure in the autoclave. During the reaction, the pressure increases further due to the release of carbon dioxide. After a reaction time of 4 h, the experiment was stopped and the reaction mixture was analyzed by gas chromatography. A total of 178 g of cyclohexylamine were found, which corresponds to a yield of 37% of theory, based on the amount of dicyclohexylcarbodiimide used.

example 2

[0023] Conversion of Dicyclohexylcarbodiimide to Cyclohexylamine

[0024] 500g of dicyclohexylcarbodiimide was heated to 190°C in an autoclave. Subsequently, 900 g of a 0.25M aqueous sodium hydroxide solution was added under stirring from a storage tank heated to 190°C. The reaction mixture builds up vapor pressure in the autoclave. During the reaction, the pressure increases further due to the release of carbon dioxide. After a reaction time of 4 h, the experiment was stopped and the reaction mixture was analyzed by gas chromatography. A total of 298 g of cyclohexylamine were found, which corresponds to a yield of 62% of theory, based on the amount of dicyclohexylcarbodiimide used.

example 3

[0026] Conversion of Dicyclohexylcarbodiimide to Cyclohexylamine

[0027] The experiment was carried out in a manner similar to that of Example 2, except that the pressure in the autoclave was adjusted to 55 bar with nitrogen and a nitrogen flow of 50 g / h was maintained through the reaction mixture throughout the reaction in order to continuously remove the carbon dioxide formed.

[0028] A total of 399 g of cyclohexylamine were found, which corresponds to a yield of 83% of theory, based on the amount of dicyclohexylcarbodiimide used.

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Abstract

The invention relates to a single or multiple-step method for the production of monoamines, diamines and/or polyamines from carbodiimide groups and, optionally, also other groups of compounds comprising isocyanate chemicals, by hydrolysis with water.

Description

technical field [0001] The present invention relates to a single- or multistage process for the preparation of mono-, di- and / or polyamines from compounds having carbodiimide groups and optionally other isocyanate chemical groups by hydrolysis with water. Background technique [0002] Mono-, di- and / or polyamines are suitable, for example, as starting material for the preparation of polyisocyanate polyaddition compounds, as starting material in polycondensation processes or for the preparation of di- or polyisocyanate compounds. Aliphatic amines can be obtained by combining alkyl halides or alcohols with NH 3 Reaction (aminolysis), by reductive amination of ketones or aldehydes, by aminoalkylation (especially the Mannich reaction), reduction of amides with lithium aluminum hydride, catalytic hydrogenation of nitriles, oximes with diboranes or nitrides LiAlH 4 It can also be prepared by Hofmann degradation, Curtis rearrangement, Ritter reaction, Schmidt reaction or Gabriell...

Claims

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Application Information

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IPC IPC(8): C07C209/62C07C211/35C07C211/36C07C211/50C07C211/00
CPCC07C209/62Y02P20/10C07C211/00C07C211/35C07C211/36C07C211/50
Inventor M·奥尔谢尔R·罗莫尔德S·科尔斯特鲁克
Owner DEGUSSA AG