Decreasing Side Products and Increasing Selectivity in the Tandem Hydroformylation/Acyloin Reaction

• Published in: ChemCatChem 2015-09, Vol.7 (17), p.2607-2613
• Main Authors: Ostrowski, Karoline A., Faßbach, Thiemo A., Vogelsang, Dennis, Vorholt, Andreas J.
• Format: Article
• Language: English
• Subjects: aldehydes; alkenes; high-pressure chemistry; hydroformylation; surfactants
• ISSN: 1867-3880; 1867-3899
• DOI: 10.1002/cctc.201500727

A highly selective catalyst system was developed for the recently discovered tandem hydroformylation/acyloin reaction by systematic investigations and changes of reaction conditions. This new catalyst system is characterized by an excellent selectivity of the desired reaction pathway with negligible amounts of side products. A successful application of the tandem hydroformylation/acyloin reaction to a variety of olefins is enabled with comparable excellent selectivities up to >99 % for the first and second reaction step, therefore a general synthesis for the conversion of olefins into acyloins is found. Furthermore, very good to excellent yields for the intermediates and final acyloin products were observed within two catalysed reactions in one preparative step. The acyloin product was applied as a nonpolar precursor for surfactants. After attaching a polar head group to the acyloin and determination of tensiometric data, the molecule showed industrial relevant surface‐active properties. Jointly successful: New catalyst systems for the tandem hydroformylation/acyloin reaction display excellent selectivities within two catalyzed reactions in one preparative step. A variety of olefins can be converted efficiently, and the acyloin product is applied successfully as a nonpolar precursor for surfactants.