1,9-Nonanediamine, 5-methyl- → 1,9-Nonanediamine, 5-methyl-
Reaction equation
[CH3:1][CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].CC(CC(C)CCCCN)CN.CC(CC(C)CC(C)CN)CN>>[CH2:1]=[C:2]([CH2:3][CH2:4][CH2:5][C:6]#[N:7])[CH2:8][CH2:9][CH2:10][C:11]#[N:12].[CH3:1][C:2]([CH2:3][CH2:4][CH2:5][C:6]#[N:7])=[CH:8][CH2:9][CH2:10][C:11]#[N:12].[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][NH2:7])[CH2:8][CH2:9][CH2:10][CH2:11][NH2:12]Participants
Procedure
Although the diadduct contained 7 dinitriles and the product of the first stage reduction contained 7 diamines (not including N-methylated C10 diamines), samples A, B, and C of the product of the second stage reduction contained only the 3 saturated diamine isomers 5-methyl-1,9-nonanediamine, 2,4-dimethyl-1,8-octanediamine, and 2,4,6-trimethyl-1,7-heptanediamine (again excluding the traces of N-methylated C10 diamines). This results from the conversion of both 5-methylenenonanedinitrile and 5-methyl-4-nonenedinitrile to 5-methyl-1,9-nonanediamine, the conversion of each of 2-methyl-4-methyleneoctanedinitrile, 2,4-dimethyl-4-octenedinitrile, and 2,4-dimethyl-3-octenedinitrile to 2,4-dimethyl-1,8-octanediamine, and the conversion of both of 2,6-dimethyl-4-methyleneheptanedinitrile and 2,4,6-trimethyl-3-heptenedinitrile to 2,4,6-trimethyl-1,7-heptanedinitrile. No unsaturation in any of MND samples A, B, and C was detected by gas-liquid chromatographic analysis.
Sources & evidence
- ORD record
- ord-3ab7df677c4f4865a1b2413635cf4697
- Source dataset
- uspto-grants-1976_09
- Patent number
- US03980621
Reaction notes
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