Defying Markovnikov: A New Spin on the Wacker Oxidation

Contributors:

Thomas Bouveyron

Dr. Kevin Hares

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In this episode of Innovate and React, I welcome back Thomas Bouveyron from and TH Köln to explore how we can make conventional petrochemical pathways more sustainable. We look into the synthesis of n-decanal, which is a crucial molecule in the fragrance industry and a key scent in Chanel No. 5. Thomas’ gaol is to shift from crude oil- to bio-based building blocks. How do you bend the rules of classical Wacker oxidation to favor the usually unfavored anti-Markovnikov product? Thomas shares his methodology, combining statistical Design of Experiments (DOE) and computational Density Functional Theory (DFT) calculations to unravel more of the catalytic mechanism. We also discuss the practical engineering hurdles of catalyst fatigue, solvent participation, and the tricky business of separating decanal from decanone.

Chapters

04:34 Defying the Markovnikov Rule in Wacker Oxidation
08:20 Design of Experiments (DOE): Optimizing with Statistics
15:43 Unraveling Reaction Mechanisms and DFT Calculations
32:31 The Real-World Engineering and Scale-Up Hurdles