Heterogeneous oxidation of pyrimidine and alkyl thioethers in ionic liquids over mesoporous Ti or Ti/Ge catalysts

Chemistry - A European Journal

Volumn 10, Issue 18, 2004, Pages 4640-4646

  Cimpeanu, Valentin ^a   Parvulescu, Vasile I ^b   Amorós, Pedro ^c   Beltrán, Daniel ^c   Thompson, Jillian M ^d   Hardacre, Christopher ^d  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Romania)

^b UNIVERSITY OF BUCHAREST   (Romania)

^c UNIVERSITY OF VALENCIA   (Spain)

^d QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

Heterogeneous catalysis; Ionic liquids; Mesoporous materials; Sulfoxidation; Thioether

Indexed keywords

CATALYSIS; HYDROGEN PEROXIDE; ORGANIC ACIDS; ORGANIC SOLVENTS; OXIDATION; TITANIUM;

DIOXANES; HETEROGENOUS OXIDATION; IONIC LIQUIDS; MESOPOROUS CATALYSTS;

ETHERS;

2 THIOBENZYL 4,6 DIMETHYLPYRIMIDINE; 2 THIOBENZYLPYRIMIDINE; 2 THIOMETHYL 4,6 DIMETHYLPYRIMIDINE; 2 THIOMETHYLPYRIMIDINE; ACID; ALKYL GROUP; ANISOLE DERIVATIVE; BIS(TRIFLUOROMETHANESULFONYL)IMIDE; DIOXANE; FLUORINE DERIVATIVE; GERMANIUM; HALIDE; HYDROGEN PEROXIDE; IMIDE; LACTIC ACID; METHYL GROUP; N HEPTYL METHYL SULFIDE; PYRIMIDINE; PYRIMIDINE DERIVATIVE; SOLVENT; SULFIDE; TETRAFLUOROBORATE; THIOANISOLE; THIOL DERIVATIVE; TITANIUM; TRIFLUOROACETIC ACID; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; UREA;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; HYDROGEN BOND; LEACHING; LIQUID; MOLECULAR STABILITY; OXIDATION; PARAMETER; POROSITY; REACTION ANALYSIS; RECYCLING; TEMPERATURE DEPENDENCE; TRANSMISSION ELECTRON MICROSCOPY; X RAY POWDER DIFFRACTION;

CATALYSIS; GERMANIUM; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PARTICLE SIZE; POROSITY; PYRIMIDINES; SILICON DIOXIDE; SOLVENTS; SULFIDES; TITANIUM;

EID: 4744371919     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400105     Document Type: Article

References (56)

1. I. I. Fernandez, N. Khiar, Chem. Rev. 2003, 103, 3651-3705.
2. T. Michel, J. Y. Gauthier, Y. Leblanc, S. Léger, H. Perrier, P. Prasit, Z. Wang, Synthesis 2001, 1778-1779.
3. a) D. C. Radu, V. Cimpeanu, F. Bertinchamps, E. M. Gaigneaux, V. I. Pârvulescu, Catal. Commun. 2003, 4, 5-9;
4. b) D. C. Radu, V. I. Parvulescu, V. Cimpeanu, E. Bartha, A. Jonas, P. Grange, Appl. Catal. A 2003, 242, 77-84.
5. D. C. Radu, A. Ion, V. I. Parvulescu, V. Cimpeanu, E. Bartha, D. T. On, S. Kaliaguine, Stud. Surf. Sci. Catal. 2003, 146, 609-612.
6. R. S. Reddy, J. S. Reddy, R. Kumar, Kumar, J. Chem. Soc. Chem. Commun. 1992, 84-85.
7. V. Hulea, Y. Moreau, F. Di Renzo, Stud. Surf. Sci. Catal. 1997, 108, 361-368.
8. D. J. Robinson, L. Davies, N. McMom, D. J. Willock, G. W. Watson, C. B. Page, D. Bethell, G. J. Hutchings, Phys. Chem. Chem. Phys. 2000, 2, 1523-1529.
9. a) M. Iwamoto, M. Yonemitsu, H. Kunishima, J. Hirosumi, N. Kita, Y. Tanaka, in Catalysis by Unique Metal Ion Structures in Solid Matrices (Eds.: G. Centi, B. Wichterlova, A. T. Bell), Kluwer Academic, Dordrecht, 2001, p. 235;
10. b) M. Iwamoto, Y. Tanaka, J. Hirosumi, N. Kita, Chem. Lett. 2001, 226-227.
11. a) M. G. Clerici, P. Ingallina, Catal. Today 1998, 41, 351-364;
12. b) L. Balducci, D. Bianchi, R. Bortolo, R. D'Aloisio, M. Ricci, R. Tassinari, R. Ungari, Angew. Chem. 2003, 115, 5087-5090; Angew. Chem. Int. Ed. 2003, 42, 4937-4940.
13. b) L. Balducci, D. Bianchi, R. Bortolo, R. D'Aloisio, M. Ricci, R. Tassinari, R. Ungari, Angew. Chem. 2003, 115, 5087-5090; Angew. Chem. Int. Ed. 2003, 42, 4937-4940.
14. a) K. R. Seddon, A. Stark, Green Chem. 2002, 4, 119-223;
15. b) C. Hardacre, J. M. Thompson, E. Mullan, D. Rooney, unpublished results.
16. Ionic Liquids in Synthesis (Eds.: P. Wasserscheid, T. Welton), Wiley-VCH, Weinheim, 2002.
17. a) T. Welton, Chem. Rev. 1999, 99, 2071-2083;
18. b) R. Sheldon, Chem. Commun. 2001, 2399-2407;
19. c) H. Olivier-Bourbigou, L. Magna, J. Mol. Catal. A 2002, 182-183, 419-437.
20. C. Baudequin, J. Baudoux, J. Levillain, D. Cahard, A.-C. Gaumont, J.-C. Plaquevent, Tetrahedron: Asymmetry 2003, 14, 3081-3093; J. Dupont, R. F. de Souza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667-3692; C. M. Gordon, Appl. Catal. A 2001, 222, 101-117.
21. C. Baudequin, J. Baudoux, J. Levillain, D. Cahard, A.-C. Gaumont, J.-C. Plaquevent, Tetrahedron: Asymmetry 2003, 14, 3081-3093; J. Dupont, R. F. de Souza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667-3692; C. M. Gordon, Appl. Catal. A 2001, 222, 101-117.
22. C. Baudequin, J. Baudoux, J. Levillain, D. Cahard, A.-C. Gaumont, J.-C. Plaquevent, Tetrahedron: Asymmetry 2003, 14, 3081-3093; J. Dupont, R. F. de Souza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667-3692; C. M. Gordon, Appl. Catal. A 2001, 222, 101-117.
23. R. T. Carlin, J. Fuller, Chem. Commun. 1997, 1345-1346.
24. K. Anderson, P. Goodrich, C. Hardacre, D. W. Rooney, Green Chem. 2003, 5, 448-453.
25. R. Hagiwara, Y. Shimizu, T. Hoshi, T. Suzuki, M. Ando, K. Ohkubo, C. Yokoyama, Tetrahedron Lett. 2001, 42, 4349-4351.
26. a) C. Hardacre, D. W. Rooney, J. M. Thompson, S. P. Katdare, World Patent WO03028882;
27. b) C. Hardacre, S. P. Katdare, D. Milroy, P. Nancarrow, D. W. Rooney, J. M. Thompson, J. Catal., in press
28. J. S. Yadav, B. V. S. Reddy, M. Sridhar Reddy, N. Niranjan, J. Mol. Catal. A 2004, 210, 99-103.
29. K. R. Seddon, J. Chem. Technol. Biotechnol. 1997, 68, 351-356.
30. M. J. Torres, PhD Thesis, Queen's University Belfast (UK), 2001.
31. V. I. Pârvulescu, D. Dumitriu, G. Poncelet, J. Mol. Catal. A 1999, 140, 91-105.
32. K. R. Seddon, A. Stark, M. J. Torres, Pure Appl. Chem. 2000, 72, 2275-2287.
33. C. Villagrán, M. Deetlefs, W. Pitner, C. Hardacre, Anal. Chem. 2004, 76, 2118-2123.
34. Following centrifugation, small amounts of catalyst remain in the ionic liquid and are difficult to remove. This residue is digested with the ionic liquid prior to ICP-AES analysis, resulting in an error of 4-2% in the values in Figure 7.
35. a) V. Hulea, P. Moreau, F. Di Renzo, J. Mol. Catal. A 1996, 111, 325-332;
36. b) V. Hulea, P. Moreau, J. Mol. Catal. A 1996, 113, 499-505.
37. D. J. Brown, The Pyrimidines, Wiley, New York, 1994, p. 609.
38. a) G. Bellussi, A. Carati, M. G. Clerici, G. Maddinelli, R. Millini, J. Catal. 1992, 133, 220-230;
39. b) M. G. Clerici, P. Ingallina, J. Catal. 1993, 140, 71-83.
40. a) O. Bortolini, F. Di Furia, G. Modena, J. Mol. Catal. 1982, 14, 53-62;
41. b) A. Arcoria, F. P. Ballistreri, G. A. Tomaselli, F. Di Furia, G. Modena, J. Mol. Catal. 1984, 24, 189-196.
42. A. Corma, M. A. Camblor, P. Esteve, A. Martinez, J. Perez-Pariente, J. Catal. 1994, 145, 151-158.
43. N. L. Lancaster, P. A. Salter, T. Welton, G. B. Young, J. Org. Chem. 2002, 67, 8855-8861.
44. A. J. Carmichael, D. M. Haddleton, S. A. F. Bon, K. R. Seddon, Chem. Commun. 2000, 1237-1238.
45. O. A. Kholdeeva, G. M. Maksimov, R. I. Maksimovskaya, L. A. Kovaleva, M. A. Fedotov, V. A. Grigoriev, C. L. Hill, Inorg. Chem. 2000, 39, 3828-3837.
46. A. J. Carmichael, C. Hardacre, J. D. Holbrey, M. Nieuwenhuyzen, K. R. Seddon, Mol. Phys. 2001, 99, 795-800.
47. D. T. On, M. P. Kapoor, E. Thibeault, J. E. Gallot, G. Lemay, S. Kaliaguine, Microporous Mesoporous Mater. 1998, 20, 107-118.
48. R. R. Hunt, E. R. Sayer, J. F. W. McOmie, J. Chem. Soc. 1959, 525-537.
49. S. Cabrera, J. El Haskouri, C. Guillem, J. Latorre, A. Beltrán, D. Beltrán, M. D. Marcos, P. Amorós, Solid State Sci. 2000, 2, 405-420.
50. J. El Haskouri, S. Cabrera, M. Gutierrez, A. Beltrán-Porter, D. Beltrán-Porter, M. D. Marcos, P. Amorós, Chem. Commun. 2001, 309-310.
51. J. El Haskouri, D. Ortiz de Zárate, C. Guillem, J. Latorre, M. Caldés, A. Beltrán, D. Beltrán, A. B. Descalzo, G. Rodríguez, R. Martfnez, M. D. Marcos, P. Amorós, Chem. Commun. 2002, 330-331.
52. J. El Haskouri, D. Ortiz de Zárate, F. Pérez-Pla, A. Cervilla, C. Guillem, J. Latorre, M.D. Marcos, A. Beltrán, D. Beltrán, P. Amorós, New J. Chem. 2002, 26, 1093-1096.
53. P. A. Z. Suarez, J. E. L. Dullius, S. Einloft, R. F. de Souza, J. Dupont, Polyhedron 1996, 15, 1217-1223.
54. P. Bonhote, A. P. Días, N. Papageorgiou, K. Kalyanasundram, M. Grätzel, Inorg. Chem. 1996, 35, 1168-1178.
55. L. Cammarata, S. G. Kazarian, P. A. Salter, T. Welton, Phys. Chem. Chem. Phys. 2001, 3, 5192-5200.
56. A. I. Vogel, Vogel's Textbook of Quantitative Inorganic Analysis, 5th ed., Longman Scientific and Technical, Harlow, 1989, pp. 370-372.