화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Journal of Industrial and Engineering Chemistry, Vol.37, 190-197, May, 2016
DOI10.1016/j.jiec.2016.03.022  Export Citation
Kinetics and mechanism of phase transfer catalyzed synthesis of aromatic thioethers by H2S-rich methyldiethanolamine
Gaurav Singh, Priya G. Nakade, Dorothy Chetia, Preeti Jha, Ujjal Mondal, Saroj Kumari, and Sujit Sen†
  • Catalysis Research Laboratory, Department of Chemical Engineering, National Institute of Technology, Rourkela 769008, India
E-mail:
Hydrogen sulphide (H2S) removal and its efficient utilization is a big challenge for many petroleum refinery industries now-a-days. The present investigation involves absorption of H2S in aqueous methyldiethanolamine (MDEA) followed by sulphidation of benzyl chloride (BC) by H2S-rich MDEA to yield dibenzyl sulphide (DBS) selectively using tetrabutylphosphonium bromide (TBPB) as a phase transfer catalyst. Ninety per cent selectivity of DBS was obtained at some level of process condition. A suitable mechanism has been proposed. An empirical kinetic model was also developed and correlated with experimental data. The present work has a potential to be used as an alternative to Claus process.
Keywords:Hydrogen sulphide;Methyldiethanolamine;Phase transfer catalysis;Kinetics;Modeling
  1. Keras LJ, US Patent No. US2011/0155646, 2011.
  2. Huang HY, Yu Y, Chung KH, Energy Fuels, 23, 4420 (2009)
  3. Bineesh KV, Kim DK, Cho HJ, Park DW, J. Ind. Eng. Chem., 16(4), 593 (2010)
  4. Vilmain JB, Courousse V, Biard PF, Azizi M, Couvert A, Chem. Eng. Res. Des., 92(2), 191 (2014)
  5. Elyassi B, Wahedi YA, Rajabbeigi N, Kumar P, Jeong JS, Zhang X, Kumar P, Balasubramanian VV, Katsiotis MS, Mkhoyan KA, Boukos N, Hashimi SA, Tsapatsis M, Microporous Mesoporous Mater., 190, 152 (2014)
  6. Wang C, Pei Y, Chemosphere, 88, 1178 (2012)
  7. Kohl AL, Nielsen RB, Gulf Publishing Company, Houston, TX. 1997.
  8. Mandal B, Bandyopadhyay SS, Environ. Sci. Technol., 40, 6076 (2006)
  9. Maity SK, Pradhan NC, Patwardhan AV, Ind. Eng. Chem. Res., 45(23), 7767 (2006)
  10. Al-Baghli NA, Pruess SA, Yesavage VF, Selim MS, Fluid Phase Equilib., 185(1-2), 31 (2001)
  11. Kaewsichan L, Al-Bofersen O, Yesavage VF, Selim MS, Fluid Phase Equilib., 183-184, 159 (2001)
  12. Sen S, Pradhan NC, Patwardhan AV, Asia-Pac. J. Chem. Eng., 6, 257 (2011)
  13. Singh G, Nakade PG, Mishra P, Jha P, Sen S, Mondal U, J. Mol. Catal. A-Chem., 411, 78 (2016)
  14. Mondal U, Puthankot A, Sen S, Singh G, R. Soc. Chem. Adv., 6, 23666 (2016)
  15. Weiland RH, Sivasubramanian MS, Dingman JC, The Proceedings of the 53rd Annual Laurence Reid Gas Condition Conference, Norman, OK, 2003.
  16. Mandal BP, Biswas AK, Bandyopadhyay SS, Sep. Purif. Technol., 35(3), 191 (2004)
  17. Xu HJ, Zhang CF, Zheng ZS, Ind. Eng. Chem. Res., 41(12), 2953 (2002)
  18. Maity SK, Pradhan NC, Patwardhan AV, Appl. Catal. A: Gen., 301(2), 251 (2006)
  19. Xue Q, Liu Y, J. Ind. Eng. Chem., 18(1), 169 (2012)
  20. Kovacs S, Novak Z, Org. Biomol. Chem., 9, 711 (2011)
  21. Pradhan NC, Sharma MM, Ind. Eng. Chem. Res., 29, 1103 (1990)
  22. Martin MT, Thomas AM, York DG, Tetrahedron Lett., 43, 2145 (2002)
  23. Bandgar BP, Pandit SS, Nagargoje SP, Sulfur Lett., 25, 247 (2002)
  24. Thankachan AP, Sindhu KS, Krishnan KK, Anilkumar G, R. Soc. Chem. Adv., 5, 32675 (2015)
  25. Salvatore RN, Smith RA, Nischwitz AK, Gavin T, Tetrahedron Lett., 46, 8931 (2005)
  26. Saxena A, Kumar A, Mozumdar S, Appl. Catal. A: Gen., 317(2), 210 (2007)
  27. Kumar A, Singh P, Kumar S, Chandra R, Mozumdar S, J. Mol. Catal. A-Chem., 276(1-2), 95 (2007)
  28. Bandgar BP, Gawande SS, Muley DB, Green Chem. Lett. Rev., 3, 49 (2010)
  29. Pradhan NC, Sharma MM, Ind. Eng. Chem. Res., 31, 1610 (1992)
  30. Gladysz JA, Wong VK, Jick BS, Tetrahedron, 35, 2329 (1979)
  31. Sen S, Maity SK, Pradhan NC, Patwardhan AV, Int. J. Chem. Sci., 5, 1569 (2007)
  32. Maity SK, Pradhan NC, Patwardhan AV, J. Mol. Catal. A-Chem., 250(1-2), 114 (2006)
  33. Miyazaki T, Katayama M, Yoshimoto S, Ogiwara Y, Sakai N, Tetrahedron Lett., 57, 676 (2016)
  34. Arisawa M, Ichikawa T, Yamaguchi M, Org. Lett., 14, 5318 (2012)
  35. Starks CM, Liotta CL, Halpern M, Phase Transfer Catalysis: Fundamentals, Applications and Industrial Perspectives, Chapman and Hall, Inc, New York, 1994.
  36. Sasson Y, Neumann R (Eds.), Handbook of Phase Transfer Catalysis, Blackie Academic and Professional, London, 1997.
  37. Yadav GD, Desai NM, Catal. Commun., 7, 325 (2006)
  38. Yadav GD, Motirale BG, Chem. Eng. J., 156(2), 328 (2010)
  39. Yadav GD, Lande SV, J. Mol. Catal. A-Chem., 244(1-2), 271 (2006)
  40. Yadav GD, Sowbna PR, Chem. Eng. J., 179, 221 (2012)
  41. Yadav GD, Sowbna PR, Chem. Eng. Res. Des., 90(9), 1281 (2012)
  42. Ido T, Susaki T, Jin G, Goto S, Appl. Catal. A: Gen., 201, 139 (2000)
  43. Mondal U, Sen S, Singh G, R. Soc. Chem. Adv., 5, 102942 (2015)
  44. Bijudasa K, Nair TDR, Curr. Chem. Lett., 3, 109 (2014)
  45. Yang HM, Li CC, J. Mol. Catal. A-Chem., 246(1-2), 255 (2006)
  46. Yang HM, Liu HC, Appl. Catal. A: Gen., 258(1), 25 (2004)
  47. Fujihira T, Takido T, Seno M, J. Mol. Catal. A-Chem., 137, 65 (1999)
  48. Lin PJ, Yang HM, J. Mol. Catal. A-Chem., 235(1-2), 293 (2005)
  49. Wu HS, Tseng MS, AIChE J., 48(4), 867 (2002)
  50. Alexander GV, Interfacial Catalysis, Mercel Dekker, Inc., New York, 2003.