Hydroformylation (the “oxo reaction”) is one of the largest homogeneous transition-metal catalyzed processes operated industrially. Chemspeed is proud to have contributed to the high-throughput screening of Rh-catalyzed bis-hydroformylation of 1,3-butadiene to adipic aldehyde with its fully automated pressure synthesizer, published by the Catalysis Research Laboratory (CaRLa), University of Heidelberg, and resulting in unprecedented maximum selectivity to adipic aldehyde. Organometallics, 2011, 30 (13), pp 3643–3651 Toward the Rhodium-Catalyzed Bis-Hydroformylation of 1,3-Butadiene to Adipic Aldehyde Stuart E. Smith †, Tobias Rosendahl †, and Peter Hofmann *†‡ † Catalysis Research Laboratory (CaRLa), University of Heidelberg, Im Neuenheimer Feld 584, D-69120 Heidelberg, Germany ‡Organisch-Chemisches Institut, University of Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany
The effects of the ligand to metal ratio, temperature, syngas pressure, partial pressures of H2 and CO, and new ligand structures have been examined on 12 of the most reasonable products resulting from the rhodium-catalyzed low-pressure hydroformylation of 1,3-butadiene. The selectivity for the desired linear dihydroformylation product, 1,6-hexanedial (adipic aldehyde), is essentially independent of all of these reaction parameters, except for ligand structure. However, the reaction parameters do have a substantial effect on the selectivity for the products, resulting from the branched addition of the rhodium hydride to the carbon–carbon double bond. The optimum reaction parameters and ligand have resulted in a so far unprecedented maximum selectivity of 50% for adipic aldehyde. About CaRLa Catalysis represents the most important general technology of industrial chemistry. More than 80 percent of all chemical products come into contact with catalysts at least once during their synthesis. High-performance catalysts have huge environmental and economic benefits. They help to significantly reduce the feedstock needs and energy consumption used for chemical processes while producing fewer by-products and waste; they open up new, more cost-effective ways of manufacturing established products and they enable an efficient manufacturing of new products. In May 2006, BASF and the University of Heidelberg set up our new joint laboratory devoted to homogeneous catalysis, CaRLa. Contrary to classical industry-academia partnerships, the concept of this lab relies on bringing academic and industrial researchers as close as possible together in one laboratory, fostering technology transfer from basic research to potential industrial applications. Additional information
