Ammonia → Isophorone diamine

HRID 1720132Notes

Reaction equation

HRID 1720132 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:8][C:7]([C:10]#[N:11])([CH3:9])[CH2:6][C:4](=[O:5])[CH2:3]1.[NH3:13]>[Co]>[CH3:1][C:2]1([CH3:12])[CH2:8][C:7]([C:10]#[N:11])([CH3:9])[CH2:6][C:4](=[O:5])[CH2:3]1.[CH3:1][C:2]1([CH3:12])[CH2:8][C:7]([CH2:10][NH2:11])([CH3:9])[CH2:6][CH:4]([NH2:13])[CH2:3]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 990683-Cyano-3,5,5-trimethylcyclohexanone

Product 2

HCID 17857Isophorone diamineYield 48%HCID 990683-Cyano-3,5,5-trimethylcyclohexanone

Reagents, catalysts & solvents 1

HCID 104730CobaltCatalyst

Procedure

EP-B 0 042 119 also discloses a Comparative Example in which isophoronenitrile and liquid ammonia are pumped into the top of a hydrogenation reactor charged with commercially available cobalt catalyst. The reaction system is kept at 270 bar with H2 ; a certain gas stream is set up and a certain amount of off-gas is withdrawn. The reaction mixture leaving the bottom of the reactor is then worked up by distillation. Despite approximately quantitative conversion of the isophoronenitrile, this embodiment produces only 48% of isophoronediamine, together with many by-products. EP-B 0 042 119 does not suggest passing a mixture containing isophoronenitrile, ammonia and organic solvent, instead of a mixture of isophoronenitrile and ammonia, over a trickle bed reactor at an essentially low pressure and without the need for a preliminary imine formation reaction.

Workup

  1. customare pumped into the top of a hydrogenation reactor
  2. customa certain amount of off-gas is withdrawn
  3. customThe reaction mixture leaving the bottom of the reactor
  4. distillationis then worked up by distillation

Sources & evidence

ORD record
ord-245634e6a8eb45ceb8a3aaf4823153ac
Source dataset
uspto-grants-1996_04
Patent number
US05504254

Reaction notes

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