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高分子合成特論

高分子合成特論. Sustainable routes to polyurethane precursors. Author : Oliver Kreye , Hatice Mutlu and Michael A. R. Meier* DOI : 10.1039/c3gc40440d Cite : Green Chem. , 2013, 15 , 1431–1455 Impact factor : 6.828. Teacher : Prof. Guey - Sheng Liou

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高分子合成特論

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  1. 高分子合成特論 Sustainable routes to polyurethane precursors Author : Oliver Kreye , HaticeMutlu and Michael A. R. Meier* DOI : 10.1039/c3gc40440d Cite :Green Chem., 2013, 15, 1431–1455 Impact factor : 6.828 Teacher:Prof.Guey-ShengLiou Student : I-Chun Tang Date : 2013.11.15.

  2. Outline • Introduction • Isocyanates • Carbamates • PolyurethaneSynthesis • Conclusion

  3. Introduction

  4. Introduction

  5. Introduction 34.1% 61.3% aromatic aliphatic 1.2% 3.4% diols (polyols) diisocyanates

  6. Isocyanates

  7. Isocyanates phosphanes, amines bases, alkali metal salts of formic or acetic acid carbamic acid derivatives phosphanes, tertiary amines (e.g. pyridine) cat. tertiary amine bases (DABCO or DBU) phospholene 1-oxides DABCO:1,4-diazabicyclo[2.2.2]octane DBU:1,8-diazabicyclo[5.4.0]undec-7-ene

  8. Isocyanatesconventional synthesis of isocyanates

  9. Isocyanatesconventional synthesis of isocyanates good yield ; small-scale synthesis high price ; laboratory scale (excess) (excess) toxicity ; laboratory scale halogens; only non-sensitive foramide

  10. Isocyanatessustainable and promising pathways to isocyanates Rh/C high temp. / pressure highly toxic catalyst residues in the final products TFAA: trifluoroacetic anhydride

  11. Carbamates

  12. Carbamatescommon reaction pathways of carbamates

  13. Carbamatesconventional synthesis of carbamates chloroformate carbamoyl chloride

  14. Carbamatesconventional synthesis of carbamates Boc-protecting group of amines carbonyl diimidazole Boc2O: di-tert-butyldicarbonate carbonyl imidazolium salts

  15. Carbamatesconventional synthesis of carbamates carbamoyl-3-nitro-1,2,4-triazoles Methyl N-(triethylammoniumsulfonyl) carbamate - Burgess reagent

  16. Carbamatesconventional synthesis of carbamates

  17. Carbamatesconventional synthesis of carbamates Strong non-nucleophilic base Boc2O α-carbamoylation (excess)

  18. Carbamatessustainable synthesis procedures of carbamates transcarbamoylation

  19. Carbamates sustainable synthesis procedures of carbamates CuCl2/ KCl

  20. Carbamatessustainable synthesis procedures of carbamates Good sustainable and eco-friendly hydroxamic acids

  21. Carbamates sustainable synthesis procedures of carbamates methyl trioxorhenium (excess)

  22. Carbamates sustainable synthesis procedures of carbamates

  23. PolyurethaneSynthesis

  24. PolyurethaneSynthesis

  25. PolyurethaneSynthesis

  26. PolyurethaneSynthesis

  27. Conclusion

  28. Conclusion • Because of the toxicity of phosgene and isocyanate, research both in industry and academia is facing increasing demand for environmentally benign and safe processes for the synthesis of these compounds. • Carbon dioxide and monoxide as well as organic carbonates play an important role in these processes. • Provide a basis for the discussion and further development of sustainable and green synthesis routes to carbamates, isocyanates and polyurethanes and illustrate the very recent progress in this field.

  29. Thanks for your listening 

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