Alcoholates of bis (p-aminocyclohexyl) methane and their use in separating stereoisomers of bis (p-aminocyclohexyl) methane

摘要

The invention relates to molecular compounds of bis (4-aminocyclohexyl) methane with cycloaliphatic alcohols or thiols, the compounds having the formula FORM:1074180/C2/1 in which X denotes oxygen or sulphur and R denotes an aliphatic hydrocarbon ring of 4-12 ring carbon atoms, or a substitution derivative of such a ring, or a ring of the said type linked to the bis (p-aminocyclohexyl) methane by a group -(R2)C(R3)-, R2 and R3 denoting hydrogen or alkyl groups of 1-5 carbon atoms. The compounds may be prepared by mixing the components, optionally in a solvent, a number of which are specified. The products are useful in changing the relative proportions of trans, trans-, trans, cis- and cis, cis-isomers of bis (4-aminocyclohexyl) methane in mixtures containing two or three of the isomers. For example, by using less than the stoichiometric proportion of alcohol or thiol, the molecular compound of the trans, trans-isomer is formed in preference to that of the other two isomers. Alternatively, a molecular compound of all three isomers may be partly crystallized, the molecular compound of the trans, trans-isomer crystallizing first. In a typical example, a dibutyl ether solution of bis (4-aminocyclohexyl) methane containing all three isomers is treated with cyclohexanol and cooled, and the solid and liquid portions are separated by filtration; the solid portion is enriched in the trans, transisomer and the liquid portion in the cis, cisisomer. Other examples describe the similar use of cyclopentanol, cycloheptanol, cyclododecanol, 2 - methylcyclohexanol, cyclohexylmethanol, cyclooctanol and cyclohexanethiol. Some other cycloaliphatic alcohols and thiols which may be used are also specified. The molecular compounds can be decomposed into their component parts by fractional distillation under atmospheric or reduced pressure.