Catalytic methylation of phenol on MgO - Surface chemistry and mechanism

Journal of Catalysis

Volumn 269, Issue 2, 2010, Pages 340-350

  Cavani, Fabrizio ^a,b   Maselli, Luca ^a,b   Passeri, Sauro ^a,b   Lercher, Johannes A ^c  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b INSTM   (Italy)

^c TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Basic catalysis; Electrophilic substitution; Magnesium oxide; Phenol methylation; Reaction mechanism

Indexed keywords

ADSORBED PHENOLS; ADSORBED SPECIES; AROMATIC RINGS; BASIC CATALYSIS; BIMOLECULAR DISPROPORTIONATION; CATALYST SURFACES; COMPUTATIONAL STUDIES; DEFUNCTIONALIZATIONS; ELECTROPHILIC SUBSTITUTIONS; FUNCTIONALIZED; IN-SITU IR; KINETIC MEASUREMENT; MAGNESIUM OXIDES; O-CRESOL; ORTHOGONAL ORIENTATIONS; PARALLEL REACTIONS; PHENOL DERIVATIVES; PHENOL METHYLATION; PRIMARY REACTION; REACTION PRODUCTS; STEADY-STATE CONDITION; SUBSTITUTED PHENOL; SYNTHETIC APPROACH;

ADSORPTION; ALKYLATION; CATALYSIS; CATALYSTS; FORMALDEHYDE; MAGNESIUM; METHANOL; METHYLATION; ORGANIC POLYMERS; REACTION INTERMEDIATES; SULFUR COMPOUNDS; SURFACE CHEMISTRY;

PHENOLS;

EID: 75249098348     PISSN: 00219517     EISSN: 10902694     Source Type: Journal    
DOI: 10.1016/j.jcat.2009.11.019     Document Type: Article

References (69)

1. Hattori H. Chem. Rev. 95 (1995) 537
2. Ono Y., and Baba T. Catal. Today 38 (1997) 321
3. Davis R.J. J. Catal. 216 (2003) 396
4. Ono Y. J. Catal. 216 (2003) 406
5. Cimino A., and Stone F.S. Adv. Catal. 47 (2002) 141
6. Barteau M. Chem. Rev. 96 (1996) 1413
7. K. Tanabe, T. Nishizaki, in: G.C. Bond et al. (Eds.), Proceedings of Sixth ICC, The Chemical Society, London, 1977, p. 863.
8. Sato S., Koizumi K., and Nozaki F. Appl. Catal. A 133 (1995) L7
9. Tanabe K., Hattori H., Sumiyoshi T., Tamaru K., and Kondo T. J. Catal. 53 (1978) 1
10. Bal R., Tope B.B., and Sivasanker S. J. Mol. Catal. A 181 (2002) 161
11. Li K.T., Wang I., and Chang K.R. Ind. Eng. Chem. Res. 32 (1993) 1007
12. Durgakumari V., and Narayanan S. J. Mol. Catal. 65 (1991) 385
13. Tanabe K., Shimazu K., Hattori H., and Shimazu K. J. Catal. 57 (1979) 35
14. T. Kotanigawa, K. Shimokawa, Bull. Chem. Soc. Jpn. 47 (1974) 950 and 1535.
15. Grabowska H., Kaczmarczyk W., and Wrzyszcz J. Appl. Catal. 47 (1989) 351
16. Velu S., and Swamy C.S. Appl. Catal. A 145 (1996) 141
17. Rao V.V., Chary K.V.R., Durgakumari V., and Narayanan S. Appl. Catal. 61 (1990) 89
18. Karuppannasamy S., Narayanan K., and Pillai C.N. J. Catal. 66 (1980) 281
19. Grabowska H., Mista W., Trawczynski J., Wrzyszcz J., and Zawadzki M. Appl. Catal. A 220 (2001) 207
20. Sreekumar K., and Sugunan S. Appl. Catal. A 230 (2002) 245
21. Mathew T., Shiju N.R., Sreekumar K., Rao B.S., and Gopinath C.S. J. Catal. 210 (2002) 405
22. Mathew T., Shylesh S., Devassy B.M., Satyanarayana C.V.V., Rao B.S., and Gopinath C.S. Appl. Catal. A 261 (2004) 292
23. Mathew T., Vijayaraj M., Pai S., Tope B.B., Hegde S.G., Rao B.S., and Gopinath C.S. J. Catal. 227 (2004) 175
24. Sato S., Koizumi K., and Nozaki F. J. Catal. 178 (1998) 264
25. Velu S., and Swamy C.S. Appl. Catal. A 119 (1994) 241
26. Velu S., and Swamy C.S. Appl. Catal. A 162 (1997) 81
27. Padmasri A.H., Venugopal A., Durgakumari V., Rama Rao K.S., and Kanta Rao P. J. Mol. Catal. A 188 (2002) 255
28. Sato S., Takahashi R., Sodesawa T., Matsumoto K., and Kamimura Y. J. Catal. 184 (1999) 180
29. Jyothi T.M., Raja T., Talawar M.B., and Rao B.S. Appl. Catal. A 211 (2001) 41
30. Bolognini M., Cavani F., Scagliarini D., Flego C., Perego C., and Saba M. Catal. Today 75 (2002) 103
31. Cavani F., Felloni C., Scagliarini D., Tubertini A., Flego C., and Perego C. Stud. Surf. Sci. Catal. 143 (2002) 953
32. Bolognini M., Cavani F., Scagliarini D., Flego C., Perego C., and Saba M. Micropor. Mesopor. Mater. 66 (2003) 77
33. Cavani F., Maselli L., Scagliarini D., Flego C., and Perego C. Stud. Surf. Sci. Catal. 155 (2005) 167
34. US Patent 4,933,509, 1989, assigned to General Electric.
35. Chantal P.D., Kaliaguine S., and Grandmaison J.L. Appl. Catal. 18 (1985) 133
36. Bregolato M., Bolis V., Busco C., Ugliengo P., Bordiga S., Cavani F., Ballarini N., Maselli L., Passeri S., Rossetti I., and Forni L. J. Catal. 245 (2007) 283
37. Pierantozzi R., and Nordquist A.F. Appl. Catal. 21 (1986) 263
38. King S.T., and Garces J.M. J. Catal. 104 (1987) 59
39. Palomares A.E., Eder-Mirth G., and Lercher J.A. J. Catal. 168 (1997) 442
40. Palomares A.E., Eder-Mirth G., Rep M., and Lercher J.A. J. Catal. 180 (1998) 56
41. Ballarini N., Cavani F., Maselli L., Montaletti A., Passeri S., Scagliarini D., Flego C., and Perego C. J. Catal. 251 (2007) 423
42. Ballarini N., Cavani F., Maselli L., Passeri S., and Rovinetti S. J. Catal. 256 (2008) 215
43. Sasaki S., Fujino K., and Takeuchi Y. Proc. Jpn. Acad. 55 (1979) 43
44. Colbourn E.A., Kendrick J., and Mackrodt C. Surf. Sci. 126 (1983) 350
45. Wong M.W. Chem. Phys. Lett. 256 (1996) 391
46. M.J. Frisch et al., Gaussian Inc., Wallingford CT, Gaussian 03, Revision C.02, 2004.
47. R. Dennington II, T. Keith, J. Millam, K. Eppinnett, W.L. Hovell, R. Gilliland, GaussView, Version 3.09, Semichem Inc., Shawnee Mission, KS, 2003.
48. Mirth G., and Lercher J.A. J. Catal. 132 (1991) 244
49. Mirth G., and Lercher J.A. J. Catal. 147 (1994) 199
50. Spitz R.N., Barton J.E., Barteau M.A., Staley R.H., and Sleight A.W. J. Phys. Chem. B 90 (1986) 4067
51. Eggers Jr. D.F., and Lingren W.E. Anal. Chem. 28 (1956) 1328
52. Tanabe K., and Saito K. J. Catal. 35 (1974) 247
53. Fukuda Y., and Tanabe K. Bull. Chem. Soc. Jpn. 46 (1973) 1616
54. Busca G., Lamette J., Lavalley J.-C., and Lorenzelli V. J. Am. Chem. Soc. 109 (1987) 5197
55. Evans J.V., and Whateley T.L. Trans. Faraday Soc. 63 (1967) 2769
56. Busca G. Catal. Today 27 (1996) 457
57. Lavalley J.C. Catal. Today 27 (1996) 377
58. Günster J., Liu G., Stultz J., Krischok S., and Goodman D.W. J. Phys. Chem. 104 (2000) 5738
59. Di Valentin C., Del Vitto A., Pacchioni G., Abbet S., Wörz A.S., and Heiz U. J. Phys. Chem. B 106 (2002) 11961
60. Peng X.D., and Barteau M.A. Langmuir 5 (1989) 1051
61. Burcham L.J., Briand L.E., and Wachs I.E. Langmuir 17 (2001) 6164
62. Mars P., Scholten J.J., and Zwietering P. Adv. Catal. 14 (1963) 35
63. Ziolek M., Kujawa J., Saur O., and Lavalley J.C. J. Phys. Chem. 97 (1992) 9761
64. Lazo N.D., Murray D.K., Kieke M.L., and Haw J.H. J. Am. Chem. Soc. 114 (1992) 8552
65. Mori T., Hoshino S., Neramittagapong A., Kubo J., and Morikawa Y. Chem. Lett. (2002) 390
66. Taylor D.R., and Ludlum K.H. J. Phys. Chem. 76 20 (1972) 2882
67. Hattori H., Shimazu K., Yoshii N., and Tanabe K. Bull. Chem. Soc. Jpn. 49 (1976) 969
68. Lecomte J., Finiels A., Geneste P., and Moreau C. Appl. Catal. A 168 (1998) 235
69. Ardizzi M., Cavani F., Dal Pozzo L., Maselli L., and Mezzogori R. Stud. Surf. Sci. Catal. 158 (2005) 1953