Method for preparation of methyl cyclohexanediamine by selective hydrogenation of toluenediamine and catalyst

A technology for producing methylcyclohexanediamine and toluenediamine, which is applied in the field of selective hydrogenation of toluenediamine to produce methylcyclohexanediamine, which can solve the problems of high catalyst preparation cost, many steps in the preparation process, and easy deactivation of the catalyst. problem, to achieve the effect of simple preparation method, high selectivity, and improved activity and selectivity

Active Publication Date: 2017-08-01
JIANGSU QINGQUAN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The production of 2,4(2,6)-methylcyclohexanediamine mainly adopts the hydrogenation of 2,4(2,6)-toluenediamine (TDA for short), and there are few reports on this at home and abroad.
However, severe deamination
[0004] 2,4(2,6)-Methylcyclohexanediamine is a fine chemical product with very high added value. According to the current reports, there is no very effective method to overcome the problem that the catalyst is easily deactivated and cannot be applied mechanically.
The traditional TDA hydrogenation catalyst has poor activity and the catalyst is easily deactivated. The catalyst reported in patent US4186145 has high activity, but the preparation process has many steps and the catalyst preparation cost is high

Method used

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  • Method for preparation of methyl cyclohexanediamine by selective hydrogenation of toluenediamine and catalyst
  • Method for preparation of methyl cyclohexanediamine by selective hydrogenation of toluenediamine and catalyst
  • Method for preparation of methyl cyclohexanediamine by selective hydrogenation of toluenediamine and catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Catalyst preparation: Weigh 10g of alumina carrier, dissolve it in an aqueous solution containing a certain amount of ruthenium chloride and cerium nitrate, add carrier mass fraction 3% polyethylene glycol into the impregnating solution, impregnate at room temperature for 12h, and then stir at 100°C , Evaporate to dryness. The obtained sample was dried at 120°C for 6 hours, calcined at 450°C for 4 hours, and reduced with hydrogen at 200°C for 3 hours to obtain a supported catalyst 1.0%Ce-5%Ru / Al 2 o 3 .

[0053] Hydrogenation reaction: carried out in a 300mL autoclave: 30.0g industrial grade TDA, 90.0g tetrahydrofuran, 1.5g catalyst 1.0%Ce-5%Ru / Al 2 o 3 , add 0.3g of lithium hydroxide to a 300mL reactor, replace the air in the reactor with nitrogen for 3 times, replace the air in the reactor with hydrogen for 5 times, control the reaction temperature at 180°C, the reaction pressure at 8.0MPa, and the stirring speed at 500 rpm to The hydrogen in the kettle is basical...

Embodiment 2

[0055] Catalyst preparation: Weigh 10g of alumina carrier, dissolve it in an aqueous solution containing a certain amount of ruthenium chloride and cerium nitrate, add carrier mass fraction 3% polyethylene glycol into the impregnating solution, impregnate at room temperature for 12h, and then stir at 100°C , Evaporate to dryness. The obtained sample was dried at 120°C for 6h, calcined at 450°C for 4h, and reduced with hydrogen at 200°C for 3h to obtain a supported catalyst 1.0%Ce-2%Ru / Al 2 o 3 .

[0056] Hydrogenation reaction: except using the catalyst prepared in this embodiment, all the others are the same as in embodiment 1.

Embodiment 3

[0058] Weigh 10g of alumina carrier, dissolve it in an aqueous solution containing a certain amount of ruthenium chloride and cerium nitrate, add carrier mass fraction 3% polyethylene glycol into the impregnating solution, impregnate at room temperature for 12h, then stir and evaporate to dryness at 100°C moisture. The obtained sample was dried at 120°C for 6h, calcined at 450°C for 4h, and reduced with hydrogen at 200°C for 3h to obtain a supported catalyst 1.0%Ce-10%Ru / Al 2 o 3 .

[0059] Hydrogenation reaction: except using the catalyst prepared in this embodiment, all the others are the same as in embodiment 1.

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Abstract

The invention provides a catalyst for preparation of methyl cyclohexanediamine by selective hydrogenation of toluenediamine. The catalyst comprises an active component and an additive, wherein the active component is ruthenium; the additive is prepared from one or several of cerium, manganese, barium, calcium, magnesium and lanthanum. The catalyst is prepared by a method with the following steps of dissolving the active component, the additive and a dispersant into a solvent, so as to obtain impregnating liquid; soaking a carrier into the impregnating liquid for impregnating; drying, roasting and reducing the impregnated carrier, so as to obtain the catalyst, wherein the dispersant is prepared from one or several of polyethylene glycol, sodium lauryl sulfate, polyvinylpyrrolidone and sodium dodecyl benzene sulfonate. The catalyst has the advantages that the activity is high, the selectivity is good, and the stability is good; the catalyst is mixed to react to complete the preparation of the methyl cyclohexanediamine by selective hydrogenation of the toluenediamine, the conversion rate of the toluenediamine is high, the selectivity of the methyl cyclohexanediamine is good, and the catalyst can be continuously used for 20 times or more.

Description

technical field [0001] The invention relates to a catalyst for selectively hydrogenating toluenediamine to produce methylcyclohexanediamine and a preparation method thereof, and a method for selectively hydrogenating toluenediamine to produce methylcyclohexanediamine, belonging to the technical field of fine chemicals. Background technique [0002] 2,4(2,6)-Methylcyclohexanediamine (C 7 h 16 N 2 , referred to as HTDA), is an important organic chemical and fine chemical intermediate, which can be used to produce powder coating hardener, aging polymerization inhibitor, light-resistant surface coating resin, curing agent for epoxy resin, and it can also be used as a synthetic detergent , Cosmetics and other daily fine chemicals raw materials. The most important use is for the preparation of methylcyclohexyl diisocyanate. The production of 2,4(2,6)-methylcyclohexanediamine mainly adopts the hydrogenation of 2,4(2,6)-toluenediamine (TDA for short), and there are few reports o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J23/63B01J23/58C07C209/72C07C211/36
CPCB01J23/58B01J23/63C07C209/72C07C211/36
Inventor 李显明徐铁勇洪俊杰李子剑吴小林郭家成
Owner JIANGSU QINGQUAN CHEM CO LTD
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