Abstract
The oxidation mechanisms of thiophene (Tp) with H2O2 over defect and perfect titanium silicalite-1 (TS-1) were investigated by means of DFT/ONIOM2 calculations for different models 7T:45T, 9T:45T and 13T:45T. The B3LYP, ωB97X-D, and M06-2X functionals were used in the high-level part of ONIOM2, with PM6 in the lower-level part. The related potential energy surface profiles are constructed based on the ωB97X-D/ONIOM2 method for 13T:45T cluster. Four possible paths are proposed for the oxidation of Tp into sulfoxide and sulfoxide into sulfone using H2O2 as an oxidant over defect and perfect TS-1. The dimerization of sulfoxide and sulfone through Diels–Alder cycloaddition is also studied. It is found that perfect TS-1 is highly unfavorable compared to defect TS-1 (TS-d). The calculated activation energy of Tp oxidation with TS-d is found to be remarkably lower than that without any zeolite catalyst. The calculated results may contribute to the understanding of the reaction mechanism of the catalytic oxidative desulfurization of sulfides in liquid fuels.
Similar content being viewed by others
References
Clerici MG, Bellussi G, Romano U (1991) J Catal 129:159–167
Hulea V, Fajula F, Bousquet J (2001) J Catal 198:179–186
Kong L, Li G, Wang X (2004) Catal Lett 92(3–4):163–167
Kong L, Li G, Wang X, Wu B (2006) Energy&Fuels 20:896–902
Sengupta A, Kamble PD, Basu JK, Sengupta S (2012) Ind Eng Chem Res 51(1):147–157
Wang W, Li G, Liu L, Chen Y (2013) Microporous Mesoporous Mater 179:165–171
Lv Q, Li G, Sun H (2014) Fuel 130:70–75
Du S, Li F, Sun Q, Wang N, Jia M, Yu J (2016) Chem Commun 52(16):3368–3371
Du S, Chen X, Sun Q, Wang N, Jia M, Valtchev V, Yu J (2016) Chem Commun 52(17):3580–3583
Sinclair PE, Catlow CRA (1999) J Phys Chem B 103:1084–1095
Damin A, Bordiga S, Zecchina A, Lamberti C (2002) J Chem Phys 117:226–237
Sever RR, Root TW (2003) J Phys Chem B 107(17):4090–4099
Sever RR, Root TW (2003) J Phys Chem B 107(17):4080–4089
Sinclair PE, Sankar G, Catlow CRA, Thomas JM, Maschmeyer T (1997) J Phys Chem B 101:4232–4237
Tozzola G, Mantegazza MA, Ranghino G, Petrini G, Bordiga S, Ricchiardi G, Lamberti C, Zulian R, Zecchina A (1998) J Catal 179(1):64–71
Sankar G, Thomas JM, Catlow CRA, Barker CM, Gleeson D, Kaltsoyannis N (2001) J Phys Chem B 105:9028–9030
Lamberti C, Bordiga S, Zecchina A, Artioli G, Marra G, Spano G (2001) J Am Chem Soc 123(10):2204–2212
Barker CM, Gleeson D, Kaltsoyannis N, Catlow CRA, Sankar G, Thomas JM (2002) Phys Chem Chem Phys 4:1228–1240
Zhuang J, Ma D, Yan Z, Deng F, Liu X, Han X, Bao X, Liu XW, Guo X, Wang X (2004) J Catal 221(2):670–673
Bonino F, Damin A, Ricchiardi G, Ricci M, Spano G, D’Aloisio R, Zecchina A, Lamberti C, Prestipino C, Bordiga S (2004) J Phys Chem B 108:3573–3583
Bordiga S, Damin A, Bonino F, Ricchiardi G, Zecchina A, Tagliapietra R, Lamberti C (2003) Phys Chem Chem Phys 5:4390–4393
Tantanak D, Vincent MA, Hillier IH (1998) Chem Commun: 1031–1032
Atoguchi T, Yao S (2003) J Mol Catal A 191:281–288
Limtrakul J, Inntam C, Truong TN (2004) J Mol Catal A 27:139–148
Wells DH, Delgass WN, Thomson KT (2004) J Am Chem Soc 126(9):2956–2962
Panyaburapa W, Nanok T, Limtrakul J (2007) J Phys Chem C 111(8):3433–3441
Sirijaraensre J, Limtrakul J (2013) Phys Chem Chem Phys 15(41):18093–18100
Sirijaraensre J, Limtrakul J (2009) Phys Chem Chem Phys 11(3):578–585
Hansen N, Kerber T, Sauer J, Bell AT, Keil FJ (2010) J Am Chem Soc 132(33):11525–11538
Van Speybroeck V, Van der Mynsbrugge J, Vandichel M, Hemelsoet K, Lesthaeghe D, Ghysels A, Marin GB, Waroquier M (2011) J Am Chem Soc 133(4):888–899
Dumrongsakda P, Ruangpornvisuti V (2012) Catal Lett 142(1):143–149
Morpurgo S (2015) J Comput Chem 36(9):660–669
Van der Mynsbrugge J, Hemelsoet K, Vandichel M, Waroquier M, Van Speybroeck V (2012) J Phys Chem C 116(9):5499–5508
Yang G, Pidko EA, Hensen EJM (2013) J Phys Chem C 117(8):3976–3986
Chiu C, Vayssilov GN, Genest A, Borgna A, Rösch N (2014) J Comput Chem 35(10):809–819
Maihom T, Boekfa B, Sirijaraensre J, Nanok T, Probst M, Limtrakul J (2009) J Phys Chem C 113(16):6654–6662
Tranca DC, Hansen N, Swisher JA, Smit B, Keil FJ (2012) J Phys Chem C 116(44):23408–23417
Sahoo SK, Nair NN (2016) J Comput Chem 37(18):1657–1667
Marra GL, Artioli G, Fitch AN, Milanesio M, Lamberti C (2000) Microporous Mesoporous Mater 40(1–3):85–94
Hijar CA, Jacubinas RM, Eckert J, Henson NJ, Hay PJ, Ott KC (2000) J Phys Chem B 104(51):12157–12164
Henry PF, Weller MT, Wilson CC (2001) J Phys Chem B 105(31):7452–7458
Yuan S, Si H, Fu A, Chu T, Tian F, Duan Y-B, Wang J (2011) J Phys Chem A 115(5):940–947
Gamba A, Tabacchi G, Fois E (2009) J Phys Chem A 113(52):15006–15015
Papayannis DK, Kosmas AM (2014) React Kinet Mech Cat 111(2):709–722
Goerigk L, Grimme S (2011) Phys Chem Chem Phys 13(14):6670–6688
Zeng X, Wang H, DeYonker NJ, Mo G, Zhou R, Zhao C (2014) Theor Chem Acc 133:1498–1503
Frisch MJ et al. (2013) Gaussian 09, Revision D.01. Gaussian Inc, Wallingford, CT
Lamberti C, Bordiga S, Arduino D, Zecchina A (1998) J Phys Chem B 102:6382–6390
Pei S, Zajac GW, Kaduk JA, Faber J, Boyanov BI, Duck D, Fazzini D, Morrison TI, Yang DS (1993) Catal Lett 21(3–4):333–344
Davis RJ, Liu Z, Tabora JE, Wieland WS (1995) Catal Lett 34(1–2):101–113
Bordiga S, Coluccia S, Lamberti C, Marchese L, Zecchina A, Boscherini F, Buffa F, Genoni F, Leofanti G (1994) J Phys Chem 98(15):4125–4132
Wang L, Xiong G, Su J, Li P, Guo H (2012) J Phys Chem C 116(16):9122–9131
Yudanov IV, Gisdakis P, Valentin CD, Rösch N (1999) Eur J Inorg Chem 12:2135–2145
Castellà-Ventura M, Akacem Y, Kassab E (2008) J Phys Chem C 112(48):19045–19054
Xu H, Han Z, Zhang D, Liu C (2015) J Mol Catal A 398:297–303
Acknowledgements
This work was supported by the National Natural Science Foundation of China (21403038), Guangdong Provincial Natural Science Foundation (2015A030313892), the Training Program for Outstanding Young Teachers in Colleges and Universities in Guangdong Province (YQ2015116).
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Wang, H., Zhou, R. & Deng, Y. Thiophene oxidation with H2O2 over defect and perfect titanium silicalite-1: a computational study. Reac Kinet Mech Cat 124, 45–60 (2018). https://doi.org/10.1007/s11144-018-1350-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11144-018-1350-z