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Method for preparing primary amine by catalytically reducing nitrile compounds through nano-porous palladium catalyst

A nanoporous, palladium catalyst technology, which is applied in the preparation of amino compounds, organic compounds, amino hydroxyl compounds, etc., can solve the problems of harsh reaction conditions, high requirements for production equipment and process control, etc., and achieve simple preparation and stable catalyst Good performance and high conversion rate

Inactive Publication Date: 2021-05-28
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In addition, in the previous catalytic reduction reaction, hydrogen was often used as the hydrogen source, and the reaction conditions were generally harsh, with certain risks, and high requirements for production equipment and process control

Method used

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  • Method for preparing primary amine by catalytically reducing nitrile compounds through nano-porous palladium catalyst
  • Method for preparing primary amine by catalytically reducing nitrile compounds through nano-porous palladium catalyst
  • Method for preparing primary amine by catalytically reducing nitrile compounds through nano-porous palladium catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Add PdNPore (2.7mg, 5mol%) catalyst and ammonia borane complex (30.86mg, 1mmol) in the mesoporous reactor, add methanol (3mL) under the nitrogen situation, add substrate benzonitrile (51.5mg ,0.5mmol), put it into an oil bath, react at 50°C for 12h, and then separate and purify by column chromatography (silica gel, 200–300 mesh; developing solvent is ethyl acetate:methanol=4:1) to obtain benzyl Amine 52.5 mg, yield 98%.

[0047]

[0048] yellow oily liquid; 1 H NMR (400MHz, CDCl 3 ),δ:7.35-7.20(m,5H),3.84(s,2H),1.54(br,2H).

Embodiment 2

[0054] Add PdNPore (2.7mg, 5mol%) catalyst and ammonia borane complex (30.86mg, 1mmol) in the mesoporous reactor, add methanol (3mL) under the nitrogen situation, add substrate benzonitrile (51.5mg , 0.5mmol), put it into an oil bath, react at 30°C for 24h, and then separate and purify by column chromatography (silica gel, 200–300 mesh; developing solvent is ethyl acetate:methanol=4:1) to obtain benzyl Amine 47.6 mg, yield 89%.

[0055]

[0056] yellow oily liquid; 1 H NMR (400MHz, CDCl 3 ),δ:7.35-7.20(m,5H),3.84(s,2H),1.54(br,2H).

Embodiment 3

[0058] Add PdNPore (2.7mg, 5mol%) catalyst and ammonia borane complex (30.86mg, 2mmol) in the mesoporous reactor, add methanol (5mL) under the nitrogen situation, add substrate benzonitrile (51.5mg , 0.5mmol), put it into an oil bath, react at 30°C for 12h, and then separate and purify by column chromatography (silica gel, 200–300 mesh; developing solvent is ethyl acetate:methanol=4:1) to obtain benzyl Amine 35.4 mg, yield 66%.

[0059]

[0060] yellow oily liquid; 1 H NMR (400MHz, CDCl 3 ),δ:7.35-7.20(m,5H),3.84(s,2H),1.54(br,2H).

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Abstract

The invention belongs to the technical field of heterogeneous catalysis, and provides a method for preparing primary amine by catalytically reducing nitrile compounds with a nano-porous palladium catalyst. According to the invention, aromatic and aliphatic nitrile compounds are adopted as raw materials, nano-porous palladium is adopted as a catalyst, ammonia borane is adopted as a hydrogen source, no additional additive is added, and selective hydrogenation is performed to prepare the corresponding primary amine. The method provided by the invention has the beneficial effects of mild reaction conditions, no additive, environmental protection, no need of hydrogen, simple operation, stable hydrogen source, safety, harmlessness, high conversion rate, high selectivity and good catalyst stability, and makes industrialization possible.

Description

technical field [0001] The invention belongs to the technical field of heterogeneous catalysis, and relates to a method for preparing primary amines by catalytically reducing nitrile compounds with a nanoporous palladium catalyst. Background technique [0002] Primary amine is an important industrial chemical, which plays an important role in the field of organic synthesis. It has a wide range of applications and has broad prospects in industries such as dyes, pigments, pesticides, medicines, fragrances, and polyurethane. [0003] Traditionally, the method systems for preparing primary amines from nitrile compounds can be divided into two categories, one is the homogeneous catalytic hydrogenation system, which is generally composed of transition metals such as Ru, Ni, Ir and related ligands to form Homogeneous catalysts, although such catalysts have the characteristics of high activity and high selectivity, the disadvantages of homogeneous catalysts, such as difficulty in se...

Claims

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Application Information

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IPC IPC(8): C07C209/48C07C209/84C07C211/27C07C211/29C07C211/17C07C211/03C07C213/02C07C213/10C07C217/58C07C227/10C07C227/40C07C229/38
CPCC07C209/48C07C209/84C07C213/02C07C213/10C07C227/10C07C227/40C07C2601/14C07C211/27C07C211/29C07C211/17C07C211/03C07C217/58C07C229/38
Inventor 包明修迪冯秀娟肖涛
Owner DALIAN UNIV OF TECH
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