Polyamines and their preparation

C - Chemistry – Metallurgy – 07 – C

Patent

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260/594.2, 260/6

C07C 211/13 (2006.01) C07C 209/48 (2006.01) C07C 211/63 (2006.01) C07C 217/42 (2006.01) C07C 233/36 (2006.01)

Patent

CA 2034076

- 9 - ABSTRACT The present invention is directed to polyamines re- presented by the following general structure: Image where R is an organic group, R' is H or CH3, and x=0 -3. Tri, tetra, penta and hexa amines, accordingly, are dis- closed. The method for making the novel polyamines comprises a multi-step reaction that commences in step (a) with the cyanoethylation of a primary amine, R-NH2, with acryloni- trile under cyanoethylation conditions to form an aminoni- trile of the structure R-NH-CH2-CH2-CN. The aminonitrile in step (b) is methylated by reaction with formic acid and formaldehyde under Leuckart reaction conditions to form a monomethyl aminonitrile of the structure R-N(CH3)-CH2-CH2- CN. The monomethyl aminonitrile then in step (c) is reduced, preferably by hydrogenation under hydrogenation conditions, to form a monomethyl diamine of the structure R-N(CH3)-CH2- CH2-CH2-NH2. The monomethyl diamine then in step (d) is chain extended again by cyanoethylation with acrylonitrile under cyanoethylation conditions to form a monomethyl dia- minonitrile of the structure R-N(CH3)-CH2-CH2-CH2-NH-CH2- CH2-CN. Finally, the monomethyl diaminonitrile in step (e) is reduced, preferably by hydrogenation under hydrogenation conditions to form the novel polyamine. Repeating step (b) results in R' being a methyl group. Repeating steps (d) and (e) extends x up to 4.

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