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Supported aminoalkyl ionic liquid-metal catalyst, and preparation method and application thereof

A metal catalyst and ionic liquid technology, applied in the supported amine alkyl ionic liquid-metal catalyst and its preparation and application fields, can solve the problems of difficulty in improving hydrogenation activity, low selectivity, deamination and the like, and achieve improved selectivity , The preparation method is simple and the reaction conditions are mild.

Active Publication Date: 2019-11-26
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The problem we are currently facing is the contradiction between conversion and selectivity. During the catalytic hydrogenation reaction of 2,4-TDA, one of the amino groups on the benzene ring (-NH 2 ) is easily removed to generate p-methylcyclohexylamine (MCHA) by-product, resulting in a decrease in the selectivity of 2,4-MCHD
When the catalyst is supported by activated carbon, the active metal is highly dispersed to make the hydrogenation activity higher, but it is easy to cause deamination when no acidic additive is added, and the selectivity of 2,4-MCHD is low
When alumina is used as the carrier, the special crystals of Ru on the carrier are beneficial to inhibit the removal of amino groups and promote the selectivity of 2,4-MCHD, but at the same time, the low metal dispersion makes it difficult to improve the hydrogenation activity

Method used

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  • Supported aminoalkyl ionic liquid-metal catalyst, and preparation method and application thereof
  • Supported aminoalkyl ionic liquid-metal catalyst, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Catalyst preparation:

[0056] Weigh 0.258g of ruthenium chloride trihydrate and 0.305g of potassium tetrachloropalladate in a three-necked flask, then add 14.1mL of deionized water into the flask, stir rapidly until completely dissolved; 2 / g, γ-Al with a bulk density of 0.85g / mL 2 o 3 Carrier 10g, stirred evenly, impregnated at room temperature for 12h; after impregnation, vacuum-dried at 110°C for about 10h; put the dried catalyst into a muffle furnace, and calcined at 400°C for 4h in an air atmosphere to obtain a calcined catalyst . Weigh 1g1-aminoethyl-3-methylimidazolium lysine salt ([C 2 NH 2 MIm][Lys]) ionic liquid and 14.1mL of deionized water were put into a three-necked flask and mixed evenly, then the roasted catalyst was added into the three-necked flask, stirred evenly, and immersed for 12h at room temperature; after the impregnation was completed, the catalyst was Vacuum drying at ℃ for about 10h; put the dried catalyst into a tube furnace, in a hydr...

Embodiment 2

[0060] Catalyst preparation:

[0061] Weigh 0.258g of ruthenium chloride trihydrate and 0.305g of potassium tetrachloropalladate in a three-necked flask, then add 14.1mL of deionized water into the flask, stir rapidly until completely dissolved; 2 / g, γ-Al with bulk density of 0.85 g / mL 2 o 3 Carrier 10g, stirred evenly, impregnated at room temperature for 12h; after impregnation, vacuum dried at 110°C for about 10h; put the dried catalyst into a muffle furnace, and calcined at 400°C for 4h in an air atmosphere to obtain a calcined catalyst . Weigh 1g 1-aminoethyl-3-methylimidazolium dicyanamide salt ([C 2 NH 2 MIm][N(CN) 2 ]) ionic liquid and 14.1mL of deionized water were put into a three-necked flask and mixed evenly, then the roasted catalyst was added into the three-necked flask, stirred evenly, and impregnated at room temperature for 12h; after impregnation, the catalyst was vacuum-dried at 110°C About 10h; put the dried catalyst into a tube furnace, and in a hydro...

Embodiment 3

[0065] Catalyst preparation:

[0066] Weigh 0.258g of ruthenium chloride trihydrate and 0.305g of potassium tetrachloropalladate in a three-necked flask, then add 14.1mL of deionized water into the flask, stir rapidly until completely dissolved; 2 / g, γ-Al with a bulk density of 0.85g / mL 2 o 3 Carrier 10g, stirred evenly, impregnated at room temperature for 12h; after impregnation, vacuum dried at 110°C for about 10h; put the dried catalyst into a muffle furnace, and calcined at 400°C for 4h in an air atmosphere to obtain a calcined catalyst . Weigh 1g 1-aminopropyl-3-methylimidazolium lysine salt ([C 3 NH 2 MIm][Lys]) ionic liquid and 14.1mL of deionized water were put into a three-necked flask and mixed evenly, then the roasted catalyst was added into the three-necked flask, stirred evenly, and immersed for 12h at room temperature; after the impregnation was completed, the catalyst was Vacuum drying at ℃ for about 10h; put the dried catalyst into a tube furnace, in a hy...

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Abstract

The invention provides a supported aminoalkyl ionic liquid-metal catalyst. The supported aminoalkyl ionic liquid-metal catalyst is composed of a carrier, and an aminoalkyl alkyl ionic liquid and metalactive components which are loaded on the carrier; the carrier is activated alumina, and the metal active components are ruthenium and palladium; the cation of the aminoalkyl ionic liquid is an alkyland aminoalkyl disubstituted imidazole cation, wherein the alkyl group is a C1-C16 alkyl group, and the aminoalkyl group is an aminoethyl group or an aminopropyl group; the anion of the aminoalkyl ionic liquid is at least one of a lysine radical, a dicyanamido group, a nitrate radical, a tetrafluoroborate ion, a hexafluorophosphate ion, an acetate ion and a hydroxyl group; and the catalyst contains 0.5-5.0 wt% of the ruthenium metal, 0.5-5.0 wt% of the palladium metal and 5-20 wt% of the ionic liquid. The invention also provides an application of the supported aminoalkyl ionic liquid-metal catalyst in catalysis of a reaction for hydrogenating 2,4-toluenediamine to synthesize 1-methyl-2,4-cyclohexanediamine. The catalyst has the advantages of high selectivity and yield of the product, simple reaction system, small amount of three wastes, low energy consumption and high industrial application values.

Description

[0001] (1) Technical field [0002] The invention relates to a loaded ionic liquid-metal catalyst and its preparation and application in catalyzing the hydrogenation of 2,4-toluenediamine to synthesize 1-methyl-2,4-cyclohexanediamine. [0003] (2) Background technology [0004] 1-Methyl-2,4-cyclohexanediamine (2,4-MCHD) is an important organic chemical and fine chemical intermediate, which can be used in the production of powder coating hardener, aging polymerization inhibitor, coating resin, ring Oxygen resin curing agent can also be used as a raw material for dyes, detergents and pharmaceutical intermediates. [0005] [0006] The preparation of 2,4-MCHD can be carried out by reducing the nitro group on the aliphatic ring, amination of the hydroxyl group, and direct catalytic hydrogenation of aromatic diamines. Considering the source of raw materials, cost, process simplicity and yield, etc., most of them are prepared by direct catalytic hydrogenation, which is simple in ...

Claims

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Application Information

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IPC IPC(8): B01J31/02B01J31/22C07C209/72C07C211/36
CPCB01J31/0292B01J31/0284B01J31/1616B01J31/1815C07C209/72B01J2231/646B01J2531/821B01J2531/824C07C2601/14C07C211/36
Inventor 丰枫张宁李小年郭伶伶卢春山张群峰
Owner ZHEJIANG UNIV OF TECH
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