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Cyanoethylation of alicyclic hypodiamine

A technology of alicyclic amine and diaminocyclohexane is applied in the field of cyanoethylation reaction of cycloaliphatic primary diamine, which can solve the problems of affecting reactivity, low reactivity and the like

Inactive Publication Date: 2002-02-27
AIR PROD & CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The steric hindrance of the amine group can affect the reactivity, e.g. o-toluidine is less reactive than p-toluidine

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 Under anhydrous conditions with a ratio of acrylonitrile to amine of ~4:1

[0021] From acrylonitrile to H 6 OTD cyanoethylation

[0022] Add 32.66 g (0.24 mol) of dry and distilled H 6 OTD (a mixture of 35% 2,3-diaminotoluene and 65% 3,4-diaminotoluene). The reaction flask was heated to 70° C., and 55.35 g of acrylonitrile (1.04 mol) was added dropwise. A mild exotherm occurred and the temperature was controlled not to exceed 77°C during the dropwise addition. The acrylonitrile addition was completed in about 20 minutes and the mixture was refluxed for 18 hours. Using chromatographic-mass spectrometry, stereoprobe mass spectrometry, and chemical ionization mass spectrometry with NH3 and ND3 to analyze the synthesized mixture, it was shown that there were 36% unreacted H 6 OTD (M + =128), 60% monocyanoethylated amine product, it uses molecular formula A (M + =181) represents; Also have 1.23% dicyanoethylated amine product, it uses molecular formula B (M...

Embodiment 2

[0024] Example 2 Under anhydrous conditions with a ratio of acrylonitrile to amine of ~2.5:1

[0025] From acrylonitrile to H 6 OTD cyanoethylation

[0026] Substantially repeat the procedure of Example 1, add 30.90 grams (0.24 mole) of H in the 250 milliliters of three-necked flasks equipped with magnetic stirring bar, oil bath, reflux condenser, dropping funnel by the method adopted before 6 OTD (a mixture of 35% 2,3-diaminotoluene and 65% 3,4-diaminotoluene). Heat the reactant to 70°C, add 32 grams (0.6 moles) of acrylonitrile dropwise so that the temperature does not exceed 77°C, the dropwise addition of acrylonitrile takes about 20 minutes to complete, and several samples are taken during the 24 hour period, the results are listed in the table 1

[0027] time (hours)

[0028] The results showed that the dicyanoethylation reaction (product B) proceeded slowly under anhydrous conditions, and little dicyanoethylation reaction occurred in the fi...

Embodiment 3

[0029] In Example 3, the ratio of acrylonitrile to amine is ~4:1 and water is added

[0030] From acrylonitrile to H 6 OTD cyanoethylation

[0031]4 grams (0.22 moles) of water were added to the reaction mixture of Example 1 at 77° C., and sampling and analysis after 10 minutes showed that 56% of the mixture was the dicyanoethylated product represented by molecular formula B. This result indicates that water catalyzes the reaction of acrylonitrile with unreacted methylcyclohexylamine and monocyanoethylated methylcyclohexylamine in the reaction product.

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PUM

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Abstract

A process for the cyanoethylation of substituted cycloaliphatic vicinal diamines which comprises reacting acrylonitrile and a diamine in the presence water as catalyst. Cyanoethylated methylcyclohexylamines are readily prepared in the presence of water.

Description

technical field [0001] The present invention relates to a process for the cyanoethylation of cycloaliphatic primary diamines. Background technique [0002] The reaction of primary and secondary amines with acrylonitrile to form the corresponding cyanoethylamines is well known. Products resulting from the cyanoethylation of organic amines are industrially important because of their wide-ranging uses in various fields. For example, cyanoethylated amines can be used as coupling agents in the preparation of azo dyes for paper, synthetic fibers, etc. Also, the pendant nitrile groups can be reduced to amines, thus generating multifunctional amines for use as curing agents for epoxies and isocyanates. [0003] In general, the addition of acrylonitrile to amines is easier than to many organic compounds, but the ease of addition to amines is quite different. For example, primary amines with two active hydrogen atoms can add one or two acrylonitrile molecules. Ad...

Claims

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Application Information

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IPC IPC(8): C07B61/00C07C253/30C07C255/24C07C255/31
CPCC07C253/30C07C2101/14C07C2601/14C07C255/24
Inventor J·J·布德尼克G·A·维达格
Owner AIR PROD & CHEM INC
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