Collect. Czech. Chem. Commun. 1983, 48, 755-765

The reactivity of amines in deamination reaction on alumina

Jiří Sedláčeka and Josef Koubekb

a Institute of Chemical Process Fundamentals, Czechoslovak Academy of Sciences, 165 02 Prague 6-Suchdol
b Prague Institute of Chemical Technology, Department of Organic Technology, 166 28 Prague 6


The rates of deamination of a series of primary, secondary and tertiary amines on alumina were determined by the method of initial reaction rates. In addition quantum chemical calculations for the same series of amines were performed by semiempirical CNDO/2 method, the interaction of molecule with surface acid centre of the catalyst being modelled by protonation of the amino group. It was found that experimental reactivities correlate well with calculated properties of the C-N bond. This shows that the cleavage of this bond takes place in the rate determining step of the reaction, giving evidence for E1 elimination mechanism. The good correlation of the experimental with calculated data confirms the correctness of the concept of the molecular adsorption of the amine on the acid catalytic centre as the first phase of heterogeneously catalysed deamination reaction.