Aniline → Dicyclohexylamine

HRID 851343Notes

Reaction equation

HRID 851343 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Ru].C1CCCCC1>[CH:2]1([NH2:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH:2]1([NH:1][CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 1

HCID 6115Aniline

Product 2

HCID 7582DicyclohexylamineHCID 7965Cyclohexylamine

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 8078CyclohexaneSolvent

Procedure

It has now surprisingly been found that aniline can be efficiently hydrogenated over a ruthenium catalyst to produce cyclohexylamine with a minimum amount of byproduct dicyclohexylamine or cyclohexane by operating at a temperature of from 160° to 180° C. and by including from about 1 to about 8 parts by weight of ammonia per 100 parts aniline by weight in the charge. Moderate hydrogen pressures of from about 2 MPa to 5 MPa can be employed, and the reaction proceeds smoothly to completion in one half hour to four hours, with no rapid rise in temperature or localized heating. The ruthenium catalyst does not appear to be poisoned by the ammonia, and can be recycled a number of times.

Sources & evidence

ORD record
ord-5dcda1bdf9ed4efcbec2b5eda58fedef
Source dataset
uspto-grants-1983_05
Patent number
US04384142

Reaction notes

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