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Ammonia → Hexamethylenediamine

HRID 23314
Notes
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Reaction equation

HRID 23314 reaction equation
[C:1](#[N:8])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7].N.[H][H].[O-2].[Al+3].[O-2].[O-2].[Al+3].[Si](=O)=O.[O-2].[Ca+2]>[Fe]>[NH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][NH2:8].[NH2:7][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][CH:1]1[NH2:8]
ParticipantsProcedureSources & evidenceReaction notes

Participants

9

Reactant 6

HCID 222AmmoniaHCID 8128AdiponitrileHCID 24261SilicaHCID 6850728CalciumoxideHCID 9989226AluminaHCID 178418361HCID 178418361, compound

Product 2

HCID 46101,2-Diaminocyclohexane
HCID 16402HexamethylenediamineYield 98.05%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

DE-A-2 429 293 discloses in Example 1 that the hydrogenation of adiponitrile in the presence of five times the weight of ammonia at from 93 to 98° C. (inlet temperature into the reactor) or at from 94 to 104° C. (outlet temperature) over an iron catalyst prepared from magnetite by reduction with hydrogen and doped with aluminum oxide, silicon dioxide, calcium oxide and vanadium pentoxide yields 98.22% of hexamethylenediamine comprising 1900 ppm of 1,2-diaminocyclohexane, and in Example 2 that the hydrogenation of adiponitrile in the presence of five times the weight of ammonia at from 93 to 98° C. (inlet temperature into the reactor) or at from 94 to 104° C. (outlet temperature) over an iron catalyst prepared from Labrador hematite ore (Fe2O3) by reduction with hydrogen and doped with aluminum oxide, silicon dioxide and calcium oxide yields 98.05% of hexamethylenediamine comprising 3500 ppm of 1,2-diaminocyclohexane.

Sources & evidence

ORD record
ord-b63b76bfbdd54ee487c6ba2080b6a6a2
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06852669B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes