Ammonia → Hexamethylenediamine

HRID 845127Notes

Reaction equation

HRID 845127 reaction equation
[CH2:1]([CH2:6][C:7]#[N:8])[CH2:2][CH2:3][C:4]#[N:5].[NH3:9]>>[NH:8]1[CH2:4][CH2:3][CH2:2][CH2:1][CH2:6][CH2:7]1.[CH2:1]([CH2:6][CH2:7][NH2:8])[CH2:2][CH2:3][CH2:4][NH:5][CH2:7][CH2:6][CH2:1][CH2:2][CH2:3][CH2:4][NH2:9].[CH2:4]([NH2:5])[CH2:3][CH2:2][CH2:1][CH2:6][CH3:7].[NH2:5][CH2:4][CH2:3][CH2:2][CH2:1][CH2:6][CH2:7][NH2:8]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 8128Adiponitrile

Product 4

HCID 8102HexylamineYield 7%HCID 8119AzepaneHCID 8924N-(6-Aminohexyl)-1,6-hexanediamineYield 3%HCID 16402HexamethylenediamineYield 15%

Procedure

0.4 liter/hour of adipodinitrile, 1.2 liter/hour of ammonia and 2.4 liters/hour of hydrogenation mixture are fed, at 270° C. and under an H2 pressure of 260 bar, into the reactor described in Example 1, and over the catalyst described in that Example. Azacycloheptane is obtained in a yield of 70% together with 3% of bishexamethylenetriamine, 7% of hexylamine and 15% of hexamethylenediamine.

Workup

  1. customare fed, at 270° C. and under an H2

Sources & evidence

ORD record
ord-441f141ba45e4f95b313919dfdf2a133
Source dataset
uspto-grants-1988_07
Patent number
US04755604

Reaction notes

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