脂肪族アミン合成反応機構に関する研究

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Aliphatic amines have been produced since long ago and are used for making products, such as fabric softeners, antistatic agents, shampoos, conditioners, and others. <BR>Aliphatic amines can be produced by many methods. Among them, the reaction of an aliphatic alcohol with a primary amine gives dialkylamine. We have already reported that the Cu-Ni catalyst provides high activity and selectivity for the reaction between dodecyl alcohol and dodecylamine. <BR>The reaction mechanism for the formation of didodecylamine from dodecyl alcohol and dodecylamine is considered to be as follows. Dodecyl alcohol is dehydrogenated to form the corresponding aldehyde (first step) which reacts with dodecylamine to give the reaction intermediate (second step). This intermediate undergoes conversion to didocecylamine by hydrogenolysis (third step). <BR>In this study the titration curves of products during reaction between dodecyl alcohol and dodecylamine were each found to have two equivalence points. It would thus appear that there is another product giving an equivalence point differing from that of the objective product (didodecylamine) or the raw material (dodecylamine). This product was sought using FT-NMR, and found to be didodecylimine. <BR>From these results, the following new mechanism is put forth. Dodecyl alcohol is dehydrogenated to the corresponding aldehyde (first step) which reacts with dodecylamine to give the reaction intermediate (second step). This intermediate subsequently undergoes dehydration to form didodecylimine (third step). Didodecylimine is then hydrogenated to give didodecylamine (fourth step).
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脂肪族アミン合成反応機構に関する研究

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