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Hydroformylation of Higher Olefins with Immobilized Catalysts

Timo J. Koch, Jürgen Klankermayer, and Walter Leitner. institute of technical and marcomolecular chemistry, RWTH-Aachen University, Worringerweg 1, Aachen, Germany

In current industrial chemistry, aldehydes derived from higher olefins are important commodities for the synthesis of various fine chemicals. The resulting aldehydes from the hydroformylation processes are easily converted into many important secondary products like detergents, paints, coatings, plasticizers, copolymers, pharmaceuticals and agrochemicals.[1] The latest generation of industrial hydroformylation processes uses rhodium catalysts in combination with water soluble phosphines (Ruhrchemie/Rhône-Poulenc-process).[2, 3] A major drawback of this approach is its limitation to water soluble alkenes. A switch to other immobilization techniques often results in unacceptable high levels of catalyst leaching.[4] In this contribution, we describe that the combination of supercritical fluids with certain established immobilization techniques can open new process alternatives and reduce the amount of leaching significantly. In combination with supercritical fluids our immobilization approach leads to a flexible and stable reaction system for the hydroformylation of alkenes with various chain length (propene to octadecene).[5, 6] Moreover, the facile catalyst immobilization procedure enables the application of a wide range of transition metal complexes. [7, 8] The beneficial combination with supercritical fluids suppresses the catalyst leaching, allows the control of conversion and can be further developed to a continuous process.[9, 10] Literature: [1] B. Fell, Tenside, Surfactants, Detergents 1998, 35, 326. [2] L. Bexten, B. Cornils, D. Kupies, (Ruhrchemie A.-G., Fed. Rep. Ger.). Application: DE, 1986, p. 25 pp. [3] H. Bahrmann, B. Cornils, W. Konkol, W. Lipps, (Ruhrchemie A.-G., Fed. Rep. Ger.). Application: DE, 1985, p. 20 pp. [4] M. F. Sellin, I. Bach, J. M. Webster, F. Montilla, V. Rosa, T. Aviles, M. Poliakoff, D. J. Cole-Hamilton, Journal of the Chemical Society, Dalton Transactions 2002, 4569. [5] W. Leitner, Green Chemistry b Roger A. Sheldon, Vol. 407, 2000. [6] M. McCarthy, H. Stemmer, W. Leitner, Green Chemistry 2002, 4, 501. [7] B. Cornils, W. A. Herrmann, I. T. Horvath, W. Leitner, S. Mecking, H. Olivier-Bourbigou, D. Vogt, Editors, Multiphase Homogeneous Catalysis, Volume 2, 2005. [8] B. Cornils, W. A. Herrmann, I. T. Horvath, W. Leitner, S. Mecking, H. Olivier-Bourbigou, D. Vogt, Editors, Multiphase Homogeneous Catalysis, Volume 1, 2005. [9] N. Tanchoux, W. Leitner, Handbook of Green Chemistry and Technology 2002, 482. [10] P. g. Jessop, W. Leitner, Editors, Chemical Synthesis Using Supercritical Fluids, 1999.