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Method for generating nitrile and amine by means of rare-earth catalytic amidines compound degradation

A technology of rare earth catalysis and rare earth catalyst, which is applied in the chemical industry, can solve the problems of high reaction temperature, toxic triazine, pollution, etc., and achieve the effects of high yield, degradation and high quality

Active Publication Date: 2018-09-28
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The literature (Chem.Rev. 1944, 35, 351-425) reported the following degradation methods of amidines, (1) unsubstituted amidines were degraded at high temperature (>240°C) to generate corresponding nitriles and ammonia Gas, under this condition, the nitrile generated by degradation is prone to self-polymerization to form a triazine product; (2) The degradation of N-substituted amidine also requires high temperature (>240°C), in addition to the corresponding nitrile and amine, it is also easy Generate toxic triazines, causing new pollution
[0004] The existing amidine degradation method is relatively complex, requiring high reaction temperature, high equipment requirements, energy consumption, easy to produce new toxic chemicals, difficult reaction selectivity control, complex products, cumbersome post-treatment, which is not conducive to product recovery Utilization and energy conservation and environmental protection

Method used

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  • Method for generating nitrile and amine by means of rare-earth catalytic amidines compound degradation
  • Method for generating nitrile and amine by means of rare-earth catalytic amidines compound degradation
  • Method for generating nitrile and amine by means of rare-earth catalytic amidines compound degradation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The degradation of N-allyl-N-phenyl benzamidine, the structural formula is as follows:

[0026]

[0027] Under nitrogen protection, add raw material N-allyl-N-phenyl benzamidine (0.5 mmol) and catalyst Yb(CH 2 SiMe 3 ) 3 (10mol%), toluene (1 mL), react at 25 °C for 12 h. The yield of benzonitrile: 96%; the yield of N-allylaniline: 89%.

[0028] Benzonitrile 1 H NMR (400 MHz, CDCl 3 ): δ 7.64-7.58 (m, 3H), 7.48-7.44 (m, 2H). N-allylaniline 1 H NMR (400 MHz, CDCl 3 ): δ 7.17-7.14 (m, 2H), 6.70-6.68 (m,1H), 6.61-6.60 (m, 2H), 6.00 (m, 1H), 5.15-5.14 (m, 2H), 3.75 (m, 2H).

Embodiment 2

[0030] The degradation of N-methyl-N-phenyl benzamidine, the structural formula is as follows:

[0031]

[0032] Under the protection of nitrogen, the raw material N-methyl-N-phenylbenzamidine (0.5 mmol) and the catalyst Yb[N(SiMe 3 ) 2 ] 3 (10mol%), toluene (1 mL), react at 25 °C for 12 h. The yield of benzonitrile: 85%; the yield of N-methylaniline: 81%.

[0033] Benzonitrile 1 H NMR (400 MHz, CDCl 3 ): δ 7.64-7.58 (m, 3H), 7.48-7.44 (m, 2H). N-Methylaniline 1 H NMR (400 MHz, CDCl 3 ): δ 7.18-7.13 (m, 2H), 6.72-6.68 (m, 1H), 6.57-6.53 (m, 2H), 3.58 (s, 1H), 2.73 (s, 3H).

Embodiment 3

[0035] The degradation of N-methyl-N-phenyl-2-methylbenzamidine, the structural formula is as follows:

[0036]

[0037] Under nitrogen protection, add raw material N-methyl-N-phenyl-2-methylbenzamidine (0.5 mmol) and catalyst Yb[N(SiMe 3 ) 2 ] 3 (8 mol%), toluene (1 mL), react at 25 °C for 7 h. The yield of o-methylbenzonitrile: 68%; the yield of N-methylaniline: 63%.

[0038] o-methylbenzonitrile 1 H NMR (400 MHz, CDCl 3 ): δ 7.58-7.56 (m, 1H), 7.50-7.46(m, 1H), 7.32-7.24 (m, 2H), 2.53 (m, 3H). N-Methylaniline 1 H NMR (400 MHz, CDCl 3 ):δ 7.18-7.13 (m, 2H), 6.72-6.68 (m, 1H), 6.57-6.53 (m, 2H), 3.58 (s, 1H), 2.73(s, 3H).

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Abstract

The invention belongs to the technical field of chemical engineering, and particularly discloses a method for generating nitrile and amine by means of rare-earth catalytic amidines compound degradation. The method includes directly degrading amidines compounds in rare-earth catalytic systems to generate the corresponding nitrile and the corresponding amine. The method has the advantages that the method is wide in application range and easy and convenient to operate; the nitrile can be generated by the aid of the method under mild conditions in a high-yield manner, and the method is high in reaction selectivity.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to a method for generating nitrile and amine by rare earth-catalyzed degradation of amidine derivatives. Background technique [0002] The amidine structural unit widely exists in the technical pesticides, and its residues are increasingly harmful to the environment on which human beings depend. At the same time, amidine compounds are important intermediates in organic synthesis, and the treatment of residues in waste liquids and waste residues is also imminent. How to efficiently degrade residual amidine compounds into valuable organic chemicals that can be recycled under mild conditions is a problem that people are eagerly expecting to be solved. [0003] The existing degradation technology of amidine derivatives is mainly carried out under the conditions of high temperature and high pressure. The literature (Chem.Rev. 1944, 35, 351-425) reported the follow...

Claims

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Application Information

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IPC IPC(8): C07C253/00C07C255/50C07C209/00C07C211/48C07C211/05C07C211/46C07D333/38
CPCC07C209/00C07C253/00C07D333/38C07C255/50C07C211/48C07C211/05C07C211/46
Inventor 周锡庚张德兴
Owner FUDAN UNIV
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