Ammonia → HCID 20449668, compound
Reaction equation
[C:1]1([C:7]([CH3:18])([CH2:13][CH2:14][CH2:15][C:16]#[N:17])[CH2:8][CH2:9][CH2:10][C:11]#[N:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.N.[H][H]>[Ni]>[C:1]1([C:7]([CH3:18])([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 125 °C
Procedure
An autoclave was charged with 0.42 mole 100 g 5-phenyl-5-methylnonanedinitrile, 10 g Raney nickel, and 9.86 mole 400 ml methanol. The reaction mixture was flushed with nitrogen and then charged with 8.9 mole 150 g ammonia. The reactor was then pressurized to 1500 psig with hydrogen and heated at 125° C. for two hours. The reactor was cooled, vented and the controls filtered and the filtrate concentrated in a rotary evaporator. Another hydrogenation run was made under essentially the same conditions described above except that 0.46 mole 110 g of 5-phenyl-5-methylnonanedinitrile was employed. The product of this run was concentrated as described above. Analysis of these concentrates by NMR and GLC indicated that complete hydrogenation of the nitrile groups to amino groups had been accomplished. The concentrates were then fractionally distilled under vacuum to give 180 g of 5-phenyl-5-methyl-1,9-nonanediamine for an 84 mole percent yielf based on the 5-phenyl-5-methylnonanedinitrile.
Workup
- customThe reaction mixture was flushed with nitrogen
- temperatureThe reactor was cooled
- filtrationthe controls filtered
- concentrationthe filtrate concentrated in a rotary evaporator
- concentrationThe product of this run was concentrated
- distillationThe concentrates were then fractionally distilled under vacuum
Sources & evidence
- ORD record
- ord-0b56fd44f885495eaa7baee9fc591acb
- Source dataset
- uspto-grants-1981_09
- Patent number
- US04288625
Reaction notes
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