CAT ALYT I C AMI N AT I O N O F ALCO HO LS
An V e r b e r c k m o e s , K . D e B u ys s e r , P . V a n D e r V o o r t
University Ghent
An . V e r b e r c k m o e s @ u g e n t . b e
Amines are important for chemical industry and numerous amines and their derivatives find applications as
agrochemicals, pharmaceuticals, food additives and personal care products. Imines are highly versatile
intermediates for the stereoselective synthesis of amines and N-heterocycles.
The catalytic amination of alcohols is a green, one-pot solvent-free catalytic reaction and is typically more
atom-economical than other amination routes. The one-pot multiple steps reaction uses a multifunctional
catalyst. The process can valorize various renewable alcohol feedstocks.
Fig. 1. Proposed hydrogen borrowing mechanism in the catalytic amination of alcohols
By the use of a well-designed multifunctional heterogeneous catalyst the amination can be performed by one
catalyst taking care of the consecutive steps: (1) dehydrogenation of alcohol, (2) condensation between
aldehyde and amine and (3) hydrogenation of imine. This reaction can be performed in a batch reactor (or
other reactor type). The reaction is solvent-free (medium = substrate molecules) and due to the potential
hydrogen borrowing mechanism (see Figure 1), there is no need for pure hydrogen in the third step.
In case one strives for selective imination, this pathway can also be used to generate hydrogen gas.
Hydrotalcite-like catalysts are cheap, highly versatile and stable catalysts with tunable chemical composition
(with incorporation of (preferably) transition metal ions or (if needed) low amounts of noble metal ions, and
with tunable metal ratios) that could execute this reaction under mild conditions at atmospheric pressure (for
a certain range of alcohols and amines). Also other type of catalysts with analogous properties can be
developed. Benchmarking will be done with available commercial catalysts.
Depending on the hydrogenation capacity of the activated catalyst and depending on the specific needs by
the partners, amines or imines or a mixture of imines/amines could be produced.
Various renewable alcohol side streams (e.g. fatty alcohols, carbohydrate type alcohols from lignocellulosic
streams (e.g. furfurylalcohol, 5-(hydroxymethyl)furfurylalcohol) and others) can be valorized towards valuable
imines and amines.
We look for partners with production of amines and/or imines and their derivatives and/or with interest in
valorizing their alcohol side streams. Polyamines produced in this way could be interesting green building
blocks for polymers.
Proposed form of presentation: poster