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CO 2 as a chemical feedstock

CO 2 as a chemical feedstock. Professor Michael North. School of Chemistry. Dymeryx. Synthesis of heterocycles from epoxides. All are known reactions but often with harsh reaction conditions (e.g. 20 bar CO 2 pressure and >100 o C for cyclic carbonate synthesis)

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CO 2 as a chemical feedstock

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  1. CO2 as a chemical feedstock Professor Michael North School of Chemistry Dymeryx

  2. Synthesis of heterocycles from epoxides All are known reactions but often with harsh reaction conditions (e.g. 20 bar CO2 pressure and >100 oC for cyclic carbonate synthesis) Could a bimetallic catalyst activate both substrates? Can we use only sustainable elements in the catalyst?

  3. Sustainable catalysis Red/orange= rising threat from increased use; Red = serious threat in next 100 years; Orange = limited availability; Many elements are endangered. http://www.chemistryinnovation.co.uk/

  4. A bimetallic aluminium(salen) catalyst M. North et al., Eur. J. Inorg. Chem.2007, 3323–3326; Chem. Eur. J.2010, 16, 6828–6843; Patent WO/2008/132474.

  5. Cyclic carbonate synthesis from terminal epoxides M. North et al., Eur. J. Inorg. Chem.2007, 3323–3326; Chem. Eur. J.2010, 16, 6828–6843.

  6. Supported catalysts

  7. Results with supported catalysts M. North et al. Patent WO/2009/109765; Chem. Commun. 2009, 2577–2579; Dalton Trans.2011, 40, 3885–3902

  8. Gas phase flow reactor Column dimensions: 3-15 cm x 1 cm. M. North, et al.Chem. Eur. J. 2009, 11454–11457; Dalton Trans.2011, 40, 3885–3902

  9. Continuous flow results at 60 oC In each case, CO2 is 21% of the gases passing into the reactor. Ethylene oxide (EO) flow rate ca 1.2 mL / min. Column length 15 cm M. North, et al.Chem. Eur. J. 2009, 11454–11457; Dalton Trans.2011, 40, 3885–3902.

  10. Continuous flow results with tBu-silica catalyst at 100 oC 3cm reactor containing 0.65g catalyst. Catalyst reactivated with BnBr M. North, et al.Chem. Eur. J. 2009, 11454–11457; Dalton Trans.2011, 40, 3885–3902

  11. Doosan Power systems test facility Flue gas composition Flow rate 20 mL/min Used El Cerrejon coal (typical hard coal): 74%C; 0.5%S; 1.5%N; 5%H; 7% H2O M. North et al.Energy Environ. Sci., 2011, 4, 4163–4170.

  12. Real flue gas flow reactor results with ethylene oxide Catalyst reactivated M. North, et al.Energy Environ. Sci., 2011, 4, 4163–4170.

  13. Synthesis of di- and trithiocarbonates M. North, et al.Synlett2010, 623–627; J. Org. Chem.2010, 75, 6201–6207.

  14. Stereochemistry • Internal epoxides are substrates. • Reaction involves inversion of epoxide stereochemistry. M. North, et al.J. Org. Chem.2010, 75, 6201–6207.

  15. Oxazolidinone synthesis Best conditions eventually found to be 5 mol% 1 at 80 oC in toluene for 24 h with no cocatalyst. Gave 100% yield with A:B = 2.2:1

  16. Other epoxides and isocyanates

  17. Acknowledgements Dr. Riccardo Pasquale Dr. Jaisiel Melendez Dr. Pedro Villuendas Dr. Carl Young Professor Bill Clegg Dr. Ross Harrington EPSRC, TSB, SSE DoosanBabcock CarbonConnections Newcastle University

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