Hydrogenation in flow: Homogeneous and heterogeneous catalysis using Teflon AF-2400 to effect gas-liquid contact at elevated pressure

Chemical Science

Volumn 2, Issue 7, 2011, Pages 1250-1257

  O'Brien, Matthew ^a   Taylor, Nicholas ^a   Polyzos, Anastasios ^a   Baxendale, Ian R ^a   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC HYDROGENATION; COMPUTER ASSISTED; ELEVATED PRESSURE; GAS LIQUIDS; GAS PERMEATION; HENRY'S LAW; HOMOGENEOUS AND HETEROGENEOUS CATALYSIS; TO EFFECT;

CATALYSIS; HYDROGENATION; POLYTETRAFLUOROETHYLENES; PRESSURE EFFECTS;

GAS PERMEABLE MEMBRANES;

EID: 79959465232     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c1sc00055a     Document Type: Article

References (71)

1. P. Sabatier and J. B. Senderens, C.R. Hebd. Seances Acad. Sci., 1900, 131, 40-42
2. P. Sabatier and J. B. Senderens, C. R. Hebd. Seances Acad. Sci., 1905, 140, 482-486
3. P. Sabatier, Ber. Dtsch. Chem. Ges., 1911, 44, 1984-2001.
4. R. Noyori, T. Ohkuma, M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi and S. Akutagawa, J. Am. Chem. Soc., 1987, 109, 5856-5858
5. T. P. Dang and H. B. Kagan, J. Chem. Soc. D, 1971, 481
6. W. S. Knowles, Acc. Chem. Res., 1983, 16, 106-112
7. H. Lindlar, Helv. Chim. Acta, 1952, 35, 446-450
8. R. H. Crabtree and M. W. Davis, J. Org. Chem., 1986, 51, 2655-2661
9. J. M. Brown, Angew. Chem., Int. Ed. Engl., 1987, 26, 190-203
10. J. A. Osborn, F. H. Jardine, J. F. Young and G. Wilkinson, J. Chem. Soc. A, 1966, 1711-1732
11. S. Nishimura, Handbook of heterogeneous catalytic hydrogenation for organic synthesis, J. Wiley, New York, 2001
12. J. G. de Vries and C. J. Elsevier, The handbook of homogeneous hydrogenation, Wiley-VCH, Weinheim, 2006
13. A. Pfaltz, J. Blankenstein, R. Hilgraf, E. Höormann, S. McIntyre, F. Menges, M. Schöonleber, S. P. Smidt, B. Wöustenberg and N. Zimmermann, Adv. Synth. Catal., 2003, 345, 33-43.
14. J. D. Holladay, J. Hu, D. L. King and Y. Wang, Catal. Today, 2009, 139, 244-260.
15. H. Cavendish, Philos. Trans. R. Soc. London, 1766, 56, 141-184.
16. G. Eigenberger and U. Wegerle, ACS Symp. Ser., 1982, 196, 133-143
17. J. A. MacDiarmid and G. J. T. North, Plant/Oper. Prog.,1989, 8, 96-99
18. F. Dryer, M. Chaos, Z. Zhao, J. Stein, J. Alpert and C. Homer, Combust. Sci. Technol., 2007, 179, 663-694
19. B. J. Lee and I.-S. Jeung, Int. J. Hydrogen Energy, 2009, 34, 8763-8769.
20. J. C. Brandt and T. Wirth, Beilstein J. Org. Chem., 2009, 5, 30
21. G. Jas and A. Kirschning, Chem.-Eur. J., 2003, 9, 5708-5723
22. T. Razzaq and C. O. Kappe, Chem. Asian J., 2010, 5, 1274-1289;
23. D. Webb and T. F. Jamison, Chem. Sci., 2010, 1, 675-680
24. C. Wiles and P. Watts, Eur. J. Org. Chem., 2008, 1655-1671
25. M. Baumann, I. R. Baxendale, S. V. Ley, N. Nikbin, C. D. Smith and J. P. Tierney, Org. Biomol. Chem., 2008, 6, 1577-1586
26. C. D. Smith, I. R. Baxendale, S. Lanners, J. J. Hayward, S. C. Smith and S. V. Ley, Org. Biomol. Chem., 2007, 5, 1559-1561;
27. I. R. Baxendale, J. J. Hayward and S. V. Ley, Comb. Chem. High Throughput Screening, 2007, 10, 802-836
28. M. Baumann, I. R. Baxendale and S. V. Ley, Molecular Diversity, DOI: 10.1007/s11030-010-9282-1
29. I. R. Baxendale and S. V. Ley, Chimia, 2008, 62, 162-168
30. V. Hessel, Chem. Eng. Technol., 2009, 32, 1655-1681
31. B. D. A. Hook, W. Dohle, P. R. Hirst, M.
32. M. Brasholz, J. M. Macdonald, S. Saubern, J. H. Ryan and A. B. Holmes, Chem.-Eur. J., 2010, 16, 11471-11480
33. A. R. Bogdan and N. W. Sach, Adv. Synth. Catal., 2009, 351, 849-854
34. A. R. Bogdan, S. L. Poe, D. C. Kubis, S. J. Broadwater and D. T. McQuade, Angew. Chem., Int. Ed., 2009, 48, 8547-8550
35. P. J. Nieuwland, K. Koch, N. van Harskamp, R. Wehrens, J. C. M. van Hest and F. P. J. T. Rutjes, Chem.-Asian J., 2010, 5, 799-805.
36. J.-I. Yoshida, Chem. Rec., 2010, 10, 332-341.
37. C. Csajagi, B. Borcsek, K. Niesz, I. Kovacs, Z. Szekelyhidi, Z. Bajko, L. Urge and F. Darvas, Org. Lett., 2008, 10, 1589-1592
38. R. V. Jones, L. Godorhazy, N. Varga, D. Szalay, L. Urge and F. Darvas, J. Comb. Chem., 2006, 8, 110-116
39. T. Fukuyama, T. Rahman, N. Kamata and I. Ryu, Beilstein J. Org. Chem., 2009, 5, 34
40. M. T. Rahman, T. Fukuyama, N. Kamata, M. Sato and I. Ryu, Chem. Commun., 2006, 2236-2238
41. P. W. Miller, L. E. Jennings, A. J. deMello, A. D. Gee, N. J. Long and R. Vilar, Adv. Synth. Catal., 2009, 351, 3260-3268
42. Y. Wada, M. A. Schmidt and K. F. Jensen, Ind. Eng. Chem. Res., 2006, 45, 8036-8042
43. R. D. Chambers, M. A. Fox, G. Sandford, J. Trmcic and A. Goeta, J. Fluorine Chem., 2007, 128, 29-33
44. S. Hübner, U. Bentrup, U. Budde, K. Lovis, T. Dietrich, A. Freitag, L. Küpper and K. Jähnisch, Org. Process Res. Dev., 2009, 13, 952-960
45. S. Saaby, K. R. Knudsen, M. Ladlow and S. V. Ley, Chem. Commun., 2005, 2909-2911
46. M. Baumann, I. R. Baxendale and S. V. Ley, Synlett, 2010, 749-752
47. V. Franckevicius, K. R. Knudsen, M. Ladlow, D. A. Longbottom and S. V. Ley, Synlett, 2006, 889-892
48. C. F. Carter, I. R. Baxendale, M. O'Brien, J. B. J. Pavey and S. V. Ley, Org. Biomol. Chem., 2009, 7, 4594-4597
49. R. Abdallah, V. Meille, J. Shaw, D. Wenn and C. de Bellefon, Chem. Commun., 2004, 372-373
50. E. V. Rebrov, M. J. F. Warnier, O. Muraza, M. H. J. M. De Croon, V. Hessel and J. C. Schouten, Proceedings of the AIChE, Houston Texas, USA, 2007
51. E. R. Murphy, J. R. Martinelli, N. Zaborenko, S. L. Buchwald and K. F. Jensen, Angew. Chem., Int. Ed., 2007, 46, 1734-1737.
52. M. O'Brien, I. R. Baxendale and S. V. Ley, Org. Lett., 2010, 12, 1596-1598.
53. A. Polyzos, M. O'Brien, T. P. Petersen, I. R. Baxendale and S. V. Ley, Angew. Chem., Int. Ed., 2011, 50, 1190-1193.
54. Manifold manufactured by Cambridge Reactor Design Ltd, Twentypence Road, Cottenham, Cambridgeshire, CB24 8PS, UK. www.cambridgereactordesign.com.
55. Teflon AF-2400 tubing was supplied by Biogeneral Inc., 9925 Mesa Rim Road, San Diego, California, USA. www.biogeneral.com
56. P. R. Resnick, US Patent 3978030
57. P. R. Resnick and W. H. Buck, in Fluoropolymers II, ed. G. Hougham, P. E. Cassidy, K. Johns and T. Davidson, Kluwer Academic, New York, pp. 25-33, 1999
58. S. M. Nemser and I. C. Roman, US Patent 5051114;
59. I. Pinnau and L. G. Toy, J. Membr. Sci., 1996, 109, 125-133.
60. R. Crabtree, Acc. Chem. Res., 1979, 12, 331-337.
61. Uniqsis Ltd, 29 Station Road, Shepreth, Cambridgeshire, UK, SG8 6GB. www.uniqsis.com.
62. K. Shirono, T. Morimatsu and F. Takemura, J. Chem. Eng. Data, 2008, 53, 1867-1871.
63. www.python.org
64. J. Tan, J. Xu, K. Wang and G. Luo, Ind. Eng. Chem. Res., 2010, 49, 10040-10045
65. M. Doan Cong and M. Ruel, J. Chem. Eng. Data, 1973, 18, 41-44
66. R. Battino and H. L. Clever, Chem. Rev., 1966, 66, 395-463
67. L. H. Turner, Y. C. Chiew, R. C. Ahlert and D. S. Kosson, AIChE J., 1996, 42, 1772-1788.
68. S. V. Ley, A. Massi, F. Rodriguez, D. C. Horwell, R. A. Lewthwaite, M. C. Pritchard and A. M. Reid, Angew. Chem., Int. Ed., 2001, 40, 1053-1055
69. I. R. Baxendale, J. Deeley, C. M. Griffiths-Jones, S. V. Ley, S. Saaby and G. K. Tranmer, Chem. Commun., 2006, 2566-2568
70. I. R. Baxendale and S. V. Ley, Ernst Schering Found. Symp. Proc., 2006, 151-185
71. S. V. Ley, C. Mitchell, D. Pears, C. Ramarao, J. Q. Yu and W. Zhou, Org. Lett., 2003, 5, 4665-4668.