1,9-Nonanediamine, 5-methyl- → 1,9-Nonanediamine, 5-methyl-

Participants

Reaction Steps

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.

Provenance & Evidence