Aromaticity of five- and six-membered heterocycles present in crude oils - An electronic description for hydrotreatment process

Fuel

Volumn 100, Issue , 2012, Pages 177-185

  Valencia, Diego ^a   Klimova, Tatiana ^a   García Cruz, Isidoro ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b INSTITUTO MEXICANO DEL PETRÓLEO   (Mexico)

Author keywords

Aromaticity; DFT; Heterocycles; Hydrotreatment; Proton affinity

Indexed keywords

AROMATICITIES; DFT; HETEROCYCLES; HYDROTREATMENT; PROTON AFFINITY;

BENZENE; CATALYST POISONING; DENSITY FUNCTIONAL THEORY; ORGANIC COMPOUNDS; PROTONATION; PROTONS; PYRIDINE; THIOPHENE;

AROMATIZATION;

EID: 84865032903     PISSN: 00162361     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fuel.2012.05.011     Document Type: Conference Paper

References (41)

1. H. Topsoe, B.S. Clausen, and F.E. Massoth Hydrotreating catalysis 1996 Springer-Verlag Berlin
2. B. Delmon New technical challenges and recent advances in hydrotreatment catalysis. A critical updating review Catal Lett 22 1988 1 32
3. C.M. Fu, and A.M. Schaffer Effect of nitrogen compounds on cracking catalysts Ind Eng Chem Prod Res Dev 24 1985 68 75
4. K. Liu, and F.T.T. Ng Effect of the nitrogen heterocyclic compounds on hydrodesulfurization using in situ hydrogen and a dispersed Mo catalyst Catal Today 149 2010 28 34
5. A. Niquille-Röthlisberger, and R. Prins Influence of nitrogen-containing components on the hydrodesulfurization of 4,6-dimethyldibenzothiophene over Pt, Pd, and PtPd on alumina catalysts Top Catal 46 2007 65 78
6. T.C. Ho, and J. Sobel Inhibition of dibenzothiophene hydrodesulfurization by di-aza heterocycles Catal Lett 99 2005 109 112
7. T.C. Ho, and D. Nguyen Poisoning effect of ethylcarbazole on hydrodesulfurization of 4,6-diethyldibenzothiophene J Catal 222 2004 450 460
8. 3 catalyst in the hydrodesulfurization of dibenzothiophene, 4-methyldibenzothiophene and 4,6-dimethyldibenzothiophene Appl Catal B Environ 35 2001 59 68
9. T.C. Ho Inhibiting effects in hydrodesulfurization of 4,6-diethyldibenzothiophene J Catal 219 2003 442 451
10. 3 catalysts Energy Fuels 8 1994 249 257
11. C. Song An overview of new approaches to deep desulfurization for ultra-clean gasoline, diesel fuel and jet fuel Catal Today 86 2003 211 263
12. A. Stanislaus, A. Marafi, and M.A. Rana Recent advances in the science and technology of ultra low sulfur diesel (ULSD) production Catal Today 153 2010 1 68
13. D.H. Kim, D.S. Choi, S. Hong, and S. Kim Atomic and electronic structure of pyrrole on Ge(1 0 0) J Phys Chem C 112 2008 7412 7419
14. W.A. Abdallah, and A.E. Nelson Density functional theory study of pyrrole adsorption on Mo(1 1 0) J Phys Chem B 109 2005 10863 10870 (Pubitemid 40844523)
15. F. Zaera Kinetics of chemical reactions on solid surfaces: deviations from conventional theory Acc Chem Res 35 2002 129 136
16. V.L. Minkin, M.N. Glukhovtsev, and B.Y.A. Simkin Aromaticity and antiaromaticity 1994 John Wiley & Sons
17. A.R. Katritzky, M. Karelson, S. Sild, T.M. Krygowski, and K. Jug Aromaticity as a quantitative concept. 7. Aromaticity reaffirmed as a multidimensional characteristic J Org Chem 63 1998 5228 5231 (Pubitemid 128491731)
18. A.D. Becke Functional thermochemistry. III. The role of exact exchange J Chem Phys 98 1993 5648 5652
19. C. Lee, W. Yang, and R.G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys Rev B 37 1988 785 789
20. Gaussian 03, Revision C.02, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery Jr JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian, Inc., Wallingford CT; 2004.
21. 4 J Chem Phys 97 1992 1087 1092
22. D.B. Chesnut The electron localization function signature of the amide bond exhibits nitrogen lone pair character J Phys Chem A 104 2000 7635 7638
23. S. Cristol, J.-P. Paul, E. Payen, D. Bougeard, F. Hutschka, and S. Clémendot DBT derivatives adsorption over molybdenum sulfide catalysts: a theoretical study J Catal 224 2004 138 147
24. 2 nanocluster - a density functional theory study of structure-reactivity relations Energy Fuels 17 2003 387 398
25. H. Yang, C. Fairbridge, J. Chen, and Z. Ring Structure-HDS reactivity relationship of dibenzothiophenes based on density functional theory Catal Lett 97 2004 217 222
26. I. García-Cruz, D. Valencia, T. Klimova, R. Oviedo-Roa, J.M. Martínez-Magadán, and R. Gómez-Balderas Proton affinity of S-containing aromatic compounds: implications for crude oil hydrodesulfurization J Mol Catal A Chem 281 2008 79 84 (Pubitemid 351222727)
27. S. Kabli, E.S.E. van Beelen, S. Ingemann, L. Henriksen, and S. Hammerumb The proton affinities of saturated and unsaturated heterocyclic molecules Int J Mass Spectrom 249 2006 370 378
28. R.J. Srinivasa, and S.G. Narahari Proton affinity of five-membered heterocyclic amines: Assessment of computational procedures Int J Quant Chem 106 2006 1217 1224
29. R.J. Gillespie, and P.L. Popelier Chemical bonding and molecular geometry: from lewis to electron densities 2001 Oxford University Press
30. W.J. Hehre, R. Ditchfield, L. Radom, and J.A. Pople Molecular orbital theory of the electronic structure of organic compounds. V. Molecular theory of bond separation J Am Chem Soc 92 1970 4796 4801
31. G. Hohlneicher, L. Packschies, and J. Weber σ-π Energy separation in homodesmotic reactions Chem Phys Chem 6 2005 2541 2551
32. 2N Catal Lett 18 1993 1 8
33. E. Furimsky, and F.E. Massoth Hydrodenitrogenation of petroleum Catal Rev Sci Eng 47 2005 297 489
34. M.J. Girgis, and B.C. Gates Reactivities, reaction networks, and kinetics in high-pressure catalytic hydroprocessing Ind Eng Chem Res 30 1991 2021 2058
35. V. La Vopa, and C.N. Satterfield Poisoning of thiophene hydrodesulfurization by nitrogen compounds J Catal 110 1988 375 387
36. 2-based hydrotreating catalysts J Catal 271 2010 280 289
37. 3 catalyst Catal Lett 129 2009 50 60
38. 3 catalyst Energy Fuels 17 2003 164 171
39. 3 Appl Catal A General 267 2004 17 25
40. M. Vrinat, R. Bacaud, D. Laurenti, M. Cattenot, N. Escalona, and S. Gamez New trends in the concept of catalytic sites over sulfide catalysts Catal Today 107 2005 570 577
41. T. Koltai, M. Macaud, A. Guevara, E. Schulz, M. Lemaire, and R. Bacaud Comparative inhibiting effect of polycondensed aromatics and nitrogen compounds on the hydrodesulfurization of alkyldibenzothiophenes Appl Catal A General 231 2002 253 261 (Pubitemid 34440723)