Preparation of pentane-1,5-diamines

Details Preparation of pentane-1,5-diamines Preparation of pentane-1,5-diamines

C - Chemistry, Metallurgy

07

C

C07C 211/01 (2006.01) C07C 209/48 (2006.01) C07C 217/42 (2006.01) C07C 229/26 (2006.01) C07D 213/38 (2006.01) C08G 59/50 (2006.01)

Patent

CA 2076917

- 20 - O.Z. 0050/42644 Abstract of the Disclosure: A process for the preparation of pentane-1,5-diamines of the formula I Image (I) where R1 is C1- to C20-alkyl, which is unsubstituted or substituted by one to four heterocyclic radicals or by C2-to C8-carbaloxy, carboxyl, C1- to C8-alkylamino and/or hydroxyl, or is C2- to C20-alkenyl, C3- to C20-cycloalkyl, C4- to C20- cycloalkylalkyl, C4- to C20-alkylcycloalkyl, C2- to C20-alkoxyalkyl, C2- to C8-alkoxycarbonyl, C1- to C20-haloalkyl, aryl, C7- to C20-aralkyl or C7- to C20-alkylaryl, and R2 and R3 independently of one another, are hydrogen, Cl- to C20-alkyl, which is unsubstituted or substituted by one to four heterocyclic radicals or by C2- to C8-carbalkoxy, carboxyl, C1- to C3-alkylamino and/or hydroxyl, or are C2- to C20-alkenyl, C3- to C20-cycloalkyl, C4- to C20-cycloalkylalkyl, C4- to C20-alkylcycloalkyl, C2- to C20-alkoxyalkyl, C2- to C8-alkoxycarbonyl, C1- to C20-haloalkyl, aryl, C7- to C20-aralkyl or C7- to C20-alkylaryl, or together are a C4- to C7-alkylene chain which is unsubstituted or substituted by one to five C1- to C4-alkyl groups, from ?-cyanoketones of the formula II - 21 - O.Z. 0050/42644 Image (II) where R1, R2 and R3 are as defined above, which comprises a) reacting the cyanoketones of the formula II with excess ammonia in a first reaction space on acidic heterogeneous catalysts at from 20 to 150°C and at from 15 to 500 bar, and b) hydrogenating the resultant reaction products using hydrogen in a second reaction space in the presence of excess ammonia on cobalt-, nickel-, ruthenium-, palladium- and/or other noble metal-containing catalysts, with or without basic components, unsup- ported or on basic or neutral supports, at from 50 to 180°C and at from 30 to 500 bar, in two spatially separate reaction spaces, and novel pentane-1,5-diamines.

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