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A computational approach to solvent selection for biphasic reaction systems

A computational approach to solvent selection for biphasic reaction systems. Martina Peters April 1, 2008 COSMO-RS Symposium 2009. Liquid-liquid biphasic systems. Easy product separation Recycling of the catalyst Suppressed inhibitory effects on the catalyst

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A computational approach to solvent selection for biphasic reaction systems

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  1. A computational approach to solvent selection for biphasic reaction systems Martina Peters April 1, 2008 COSMO-RS Symposium 2009

  2. Liquid-liquid biphasic systems • Easy product separation • Recycling of the catalyst • Suppressed inhibitory effects on the catalyst • Important examples: SHOP & Rhône-Poulenc

  3. Search for the “perfect“ solvent • Conversion • Yield • Toxicity • Enantiomeric excess • Catalyst stability • Catalyst activity • Price $$ • Boiling point • Miscibility • Analytics • Recyclability • Long-term stability • Robustness • ...

  4. Approach • Existing Solvents • MTBE • DIPE • DEE • Cyclohexanone • Hexane • Heptane • Toluene • IL 1 • … • Existing Solvents • MTBE • Hexane • IL 1 • New Solvents • IL 2 • IL 3 • IL 4 • … • DIPE • DEE • Heptane • Toluene • Cyclohexanone • … Experimental approach Computational approach Guided experiments Bigger solvent space Fast Laborious Expensive

  5. The sample reaction • Possible solvents: • Hexane • Heptane • MTBE • DIPE • Toluene • [BMIM][BTA] • [BMIM][PF6] H2O • Biphasic system • Asymmetric reduction • Alcoholdehydrogenase from L. brevis M.F. Eckstein et al., Adv. Synth. Catal.2006, 348, 1591. M.F. Eckstein et al., Adv. Synth. Catal.2006, 348, 1597.

  6. Concept

  7. Partition coefficients A.C. Spiess et al., Chem. Eng. Proc.2008, 47, 1034.

  8. Concept

  9. Equilibrium constant K Dr. Kai Leonhard DG = -RT lnK Hess cycle: DGformation + DGsolvation = DGsolution Quantum mechanics COSMO-RS M. Peters et al., AIChE Journal, 2008, 54, 2729-2734.

  10. Concept

  11. Reaction system free of choice 7 different parameters solvent dependent • Phase volume ratio V • Cosubstrate/substrate ratio S • Partition coefficients a, b, g, d • Equilibrium constant K M. Peters et al., Ind. Eng. Chem. Res.2007, 46, 7073

  12. Conversion X and yield h – prediction* *Basis for prediction: measured Px and measuredK

  13. Conversion X and yield h – prediction* *Basis for prediction: calculated Px and calculated K

  14. Conversion X and yield h – prediction* *Basis for prediction: calculated Px and measuredK

  15. Conclusion Theoretical solvent selection possible! But: Experimental verification advisable Computational approach to solvent selection • Prediction of partition coefficients • Prediction of equilibrium constants • Analytical solution for conversion and yield • Prediction of conversion and yield in biphasic systems

  16. Acknowledgements DFG GK 1166 BioNoCo„Biocatalysis in non-conventional media“ www.bionoco.org Prof. Walter Leitner Dr. Lasse Greiner Prof. Jochen Büchs Dr. Marrit Eckstein Dr. Kai Leonhard Dr. Antje Spiess

  17. Thank you for your attention!

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