Ammonia → 6-Aminohexanenitrile

HRID 1954489Notes

Reaction equation

HRID 1954489 reaction equation
[CH:1]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8])=O.[NH3:9]>[Co].[H][H]>[NH2:9][CH2:1][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8].[NH2:9][CH2:1][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH2:8]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 110406526-Oxohexanenitrile

Product 2

HCID 16402HexamethylenediamineHCID 170796-AminohexanenitrileYield 56%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 178418361HCID 178418361, compoundSolvent2×

Conditions

Temperature
100 °C

Procedure

In the autoclave described in Example 1 there were placed 32 g of 5-formylvaleronitrile and 10 g of cobalt catalyst under argon. The autoclave was then sealed and 130 ml of ammonia were forced in. The mixture was stirred using a magnetic stirrer and was heated to 100° C. and the overall pressure raised to 100 bar by forcing in hydrogen and then kept at this value by continuous replenishment with hydrogen. After a period of 20 hours the autoclave was depressurized and the hydrogenation effluent analyzed by gas chromatography. The products formed comprised 56% of 6-aminocapronitrile and 6% of hexamethylene diamine (conversion 100%).

Workup

  1. customThe autoclave was then sealed
  2. temperaturethe overall pressure raised to 100 bar

Sources & evidence

ORD record
ord-dafe66e13ec6447b814e6b47634f648b
Source dataset
uspto-grants-2000_09
Patent number
US06121481

Reaction notes

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