Hydroformylation of post-metathesis product using commercial rhodium-based catalysts

Abstract

The hydroformylation of the post-metathesis product 7-tetradecene using different commercially available homogeneous rhodium-based catalysts has been investigated. The influences of different reaction conditions such as temperature (60–90 °C), pressure (10–30 bar), ligand-to-metal ratio (0–30) and unwanted impurities in the reaction environment were found to have significant effect on resulting product distributions and catalyst performance parameters such as the turnover number and selectivity. The two main reactions observed were hydroformylation of 7-tetradecene to the target aldehyde product 2-hexylnonanal over the entire temperature range and isomerization above 70 °C. Selectivities as high as 99% toward the target product 2-hexylnonanal were observed with turnover numbers up to 980 (mol product mol Rh−1). A comparative study with different post-metathesis products also shows preferred selectivity (67–85%) toward corresponding branched aldehydes which is advantageous in the industrial context in which mixed post-metathesis feedstocks might be expected.