Synthesis of renewable plasticizer alcohols by formal anti-Markovnikov hydration of terminal branched chain alkenes via a borane-free oxidation/reduction sequence

Green Chemistry

Volumn 14, Issue 9, 2012, Pages 2450-2456

  Harvey, Benjamin G ^a   Meylemans, Heather A ^a   Quintana, Roxanne L ^a  

^a NAVAL AIR WARFARE CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84870224032     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c2gc35595g     Document Type: Article

References (38)

1. R. A. Sheldon Catal. Today 2011 167 3 13
2. F. Cherubini Energy Convers. Manage. 2010 51 1412 1421
3. E. Dinjus, U. Arnold, N. Dahmen, R. Höfer and W. Wach, Sustainable Solutions for Transportation, in Sustainable Solutions for Modern Economies, ed., R. Höfer, RSC Publishing, Cambridge, 2009, ch. 8, pp. 125-163
4. D. M. Alonso J. Q. Bond J. A. Dumesic Green Chem. 2010 12 1493 1513
5. L. E. Manzer Top. Catal. 2010 53 1193 1196
6. A. Gandini Macromolecules 2008 41 9491 9504
7. J. Van Haveren E. L. Scott J. Sanders Biofuels, Bioprod. Biorefin. 2008 2 41 57
8. B. Yin M. Hakkarainen J. Appl. Polym. Sci. 2011 4 2400 2407
9. A. Greco D. Brunetti G. Renna G. Mele A. Maffezzoli Polym. Degrad. Stab. 2010 95 2169 2174
10. M. G. A. Vieira M. A. da Silva L. O. dos Santos M. M. Beppu Eur. Polym. J. 2011 47 254 263
11. R. Tudor M. Ashley Platinum Met. Rev. 2007 51 116 126
12. B. G. Harvey H. A. Meylemans J. Chem. Technol. Biotechnol. 2011 86 2 9
13. M. E. Wright B. G. Harvey R. L. Quintana Energy Fuels 2008 22 3299 3302
14. B. G. Harvey R. L. Quintana Energy Environ. Sci. 2010 3 352 357
15. H. C. Brown J. C. Chen J. Org. Chem. 1981 46 3978 3988
16. V. K. Aggarwal S. P. Thomas Angew. Chem., Int. Ed. 2009 48 1896 1898
17. G. Dong P. Teo Z. K. Wichens R. H. Grubbs Science 2011 333 1609 1612
18. L. Hintermann ChemCatChem 2012 4 321 322
19. A. N. Campbell P. B. White I. A. Guzei S. S. Stahl J. Am. Chem. Soc. 2010 132 15116 15119
20. M. Schroder Chem. Rev. 1980 80 187 213
21. H. C. Kolb M. S. VanNieuwenhze K. B. Sharpless Chem. Rev. 1994 94 2483 2547
22. S. V. Ley C. Ramarao A.-L. Lee N. Ostergaard S. C. Smith I. M. Shirley Org. Lett. 2003 5 185 187
23. L. Emmanuvel T. M. Ali Shaikh A. Sudalai Org. Lett. 2005 7 5071 5074
24. F. Fringuelli R. Germani F. Pizzo G. Savelli Synth. Commun. 1989 19 1939 1943
25. C. P. Park J. H. Lee K. S. Yoo K. W. Jung Org. Lett. 2010 12 2450 2452
26. F. Dubois A. Murphy T. D. P. Stack Org. Lett. 2003 5 2469 2472
27. K. Kosswig, K. Gelfert and F. Kloh, Ger. Pat., DE1276619, 1968
28. C. Cordier S. Leach A. Nelson Science of Synthesis 2007 29 407 486
29. I. Bucsi Á. Molnár M. Bartók G. A. Olah Tetrahedron 1994 50 8195 8202
30. M. L. Kantam P. L. Santhi M. F. Siddiqui Tetrahedron Lett. 1993 34 1185 1186
31. H. P. A. Groll and G. Hearne, US Pat., 2042224, 1934
32. M. Bartók and A. Molnár, Dehydration of Diols, in Ethers, Crown Ethers, Hydroxyl Groups and their Sulphur Analogues, ed., S. Patai, John Wiley and Sons, Ltd, Chichester, UK, 1981, vol. 2
33. B. Katryniok S. Paul V. Bellière-Baca P. Rey F. Dumeignil Green Chem. 2010 12 2079 2098
34. R. C. Mebane A. J. Mansfield Synth. Commun. 2005 35 3083 3086
35. M. Rahma C. S. Brazel Prog. Polym. Sci. 2004 29 1223 1248
36. A. Stuart M. M. McCallum D. Fan D. J. LeCaptain C. Y. Lee D. K. Mohanty Polym. Bull. 2010 65 589 598
37. R. Hofer and K. Hinrichs, Additives for the Manufacture and Processing of Polymers, in Handbook Environmental Chemistry, Vol. 12, Polymers: Opportunities and Risks II: Sustainability, Product Design and Processing, ed., P. Eyerer, M. Weller, C. Hübner, Springer Verl., Berlin, Heidelberg, 2010, pp. 97-145
38. M. Hrusovsky, J. Hrcka, Z. Cvengrosova and K. Fancovic, Czech Patent CS 224913, 1984