Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1976-09-20
1977-04-26
Schwartz, Gerald A.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
260566F, C07C 8518, C07C 8520
Patent
active
040201040
ABSTRACT:
A process is described for isomerizing the cis,cis- and cis,trans-isomers of di-(p-aminocyclohexyl)methane to the corresponding trans,trans-isomer. The starting isomer, or mixture of isomers, is converted to the corresponding bis-benzaldimine by reaction with benzaldehyde (or benzaldehyde containing 1 to 3 inert substituents), the bis-benzaldimine is isomerized in the presence of a basic catalyst (potassium t-butoxide, potassium hydroxide preferred) to give predominantly the trans,trans-isomer of the bis-benzaldimine, and the latter is subjected to acid hydrolysis to yield the trans,trans-isomer of the free diamine. The process can be applied to the individual cis,cis- and cis,trans-isomers of the diamine as well as to admixtures of these isomers with the trans,trans-isomer, such as the mixtures of these stereoisomers obtained by catalytic hydrogenation of di-(p-aminophenyl)methane.
REFERENCES:
patent: 3856862 (1974-12-01), Chung et al.
Firth Denis A.
Kekich John
Schwartz Gerald A.
The Upjohn Company
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