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Synthesis of N-methylaniline by Aniline Alkylation with Methanol over Sn-MFI Molecular Sieve

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Abstract

Sn-MFI molecular sieves (Tin silicalite-1) with SiO2/SnO2 molar ratio of 50–150 were synthesized and characterized. Elemental analysis, XRD and DRUV–vis confirmed that prepared samples were of MFI zeolite structure and Sn was incorporated in MFI framework. Vapor phase methylation of aniline over Sn-MFI was systematically studied and optimizations of process parameters were carried out. Sn-MFI (SiO2/SnO2 = 50) was found to be optimum catalyst with 55% aniline conversion and 60% N-methylaniline selectivity. At lower space velocity (higher contact time) of 1 h−1, aniline conversion was found to be increased to 71% with reduction in N-methylaniline selectivity to 39% and increased in N,N-dimethylaniline selectivity to 58%. The reaction follows first order kinetics with respect to aniline having activation energy of 7.3 kcal/mol.

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References

  1. Narayanan S, Durgakumari V, Rao AS (1994) Appl Catal A 111:133

    Article  CAS  Google Scholar 

  2. Santhanalakshmi J, Raja T (1996) Appl Catal A 147:69

    Article  CAS  Google Scholar 

  3. Sunwanprasop S, Nhujak T, Roengsumran S, Petsom A (2004) Ind Eng Chem Res 43:4973

    Article  Google Scholar 

  4. Stauffer SR, Hartwig JF (2003) J Am Chem Soc 125:6977

    Article  CAS  Google Scholar 

  5. Kim JS, Shon OJ, Rim JA, Kim SK, Yoon J (2002) J Org Chem 67:2348

    Article  CAS  Google Scholar 

  6. Narayanan S, Deshpande K (2000) Appl Catal 199:1

    Article  CAS  Google Scholar 

  7. Baustista FM, Campelo JM, Luna GD, Marinas JM, Romero AA, Urbano MR (1997) J Catal 172:103

    Article  Google Scholar 

  8. Baustista FM, Campelo JM, Luna GD, Marinas JM, Romero AA (1998) Appl Catal A 166:39

    Article  Google Scholar 

  9. Garces LJ, Makwana VD, Hincapie B, Sacco A, Suib SL (2003) J Catal 217:107

    CAS  Google Scholar 

  10. Ivanova II, Pomakhina EB, Rebrov AI, Hunger M, Kolyagin YG, Weitkamp J (2001) J Catal 203:375

    Article  CAS  Google Scholar 

  11. Selva M, Tundo P, Foccardi T (2005) J Org Chem 70:2476

    Article  CAS  Google Scholar 

  12. Ko A, Yang C, Zhu W, Lin H (1996) Appl Catal A 134:53

    Article  CAS  Google Scholar 

  13. Vijayaraj M, Gopinath CS (2006) J Catal 241:83

    Article  CAS  Google Scholar 

  14. Sreekumara K, Rajab T, Kiranb BP, Sugunana S, Rao BS (1999) Appl Catal A 182:327

    Article  Google Scholar 

  15. Park YK, Park K, Woo S (1994) Catal Lett 26:169

    Article  CAS  Google Scholar 

  16. Yang C, He N, Xu Q (1999) J Incl Phen Macro 35:123

    Article  CAS  Google Scholar 

  17. Su BL, Barthomeuf D (1995) Appl Catal A 124:73

    Article  CAS  Google Scholar 

  18. Elangovan SP, Kannan C, Arabindoo B, Murugesan V (1998) Appl Catal A 174:213

    Article  CAS  Google Scholar 

  19. Yadav GD, Doshi NS (2003) J Mol Catal A 194:195

    Article  CAS  Google Scholar 

  20. Narayanan S, Deshpande K (1995) J Mol Catal A 104:L109

    Article  Google Scholar 

  21. Narayanan S, Prasad BP (1995) J Mol Catal A 96:57

    Article  CAS  Google Scholar 

  22. Luque R, Campelo JM, Luna D, Marinas JM, Romero AA (2007) J Mol Catal A 269:190

    Article  CAS  Google Scholar 

  23. Woo SI, Lee JK, Hong BS, Park YK, Uh YS (1989) Stud Surf Sci Catal 49B:1095

    Article  Google Scholar 

  24. Chen PY, Chen MC, Chu HY, Chang NS, Chuang TK (1986) Stud Surf Sci Catal 28:739

    Article  CAS  Google Scholar 

  25. Campelo JM, Lafont F, Marinas JM (1995) Zeolites 15:97

    Article  CAS  Google Scholar 

  26. Karge HG, Dondur V (1990) J Phys Chem 94:765

    Article  CAS  Google Scholar 

  27. Karge HG, Dondur V, Weitkamp J (1991) J Phys Chem 95:283

    Article  CAS  Google Scholar 

  28. Jing H, Edulji SK, Gibbs JM, Stern CL, Zhou H, Nguyen ST (2004) Inorg Chem 43:4315

    Article  CAS  Google Scholar 

  29. Bryce MR (1991) Chem Soc Rev 20:355

    Article  CAS  Google Scholar 

  30. Panchgalle SP, Kalkote UR, Niphadkar PS, Joshi PN, Chavan SP, Chaphekar GM (2004) Green Chem 6:308

    Article  CAS  Google Scholar 

  31. Corma A, Nemeth L, Renz M, Valencia S (2001) Nature 412:423

    Article  CAS  Google Scholar 

  32. Mal KN, Bhaumik A, Kumar R, Ramaswamy AV (1995) Catal Lett 33:387

    Article  CAS  Google Scholar 

  33. Gaydhankar TR, Joshi PN, Kalita P, Kumar R (2007) J Mol Catal A: Chem 265:306

    Article  CAS  Google Scholar 

  34. Mal NK, Arumugamangalam V, Ramaswamy AV (1996) J Mol Catal A: Chem 105:149

    Article  CAS  Google Scholar 

  35. Mal NK, Arumugamangalam V, Ramaswamy AV (1996) Appl Catal A: Gen 143:75

    Article  CAS  Google Scholar 

  36. Samanta S, Mal NK, Manna A, Bhaumik A (2004) Appl Catal A: Gen 273:157

    Article  CAS  Google Scholar 

  37. Boronat M, Corma A, Renz M (2006) J Phys Chem B 110:21168

    Article  CAS  Google Scholar 

  38. Corma A, Domine ME, Valencia S (2003) J Catal 215:294

    Article  CAS  Google Scholar 

  39. Niphadkar PS, Kotwal MS, Deshpande SS, Bokade VV, Joshi PN (2009) Mater Chem Phys 114:344

    Article  CAS  Google Scholar 

  40. Bibby LM, Aldridge LP, Milestone NB (1981) J Catal 72:373

    Article  CAS  Google Scholar 

  41. Chaudhari K, Das TK, Rajmohanan PR, Lazar K, Sivasanker S, Chandwadkar AJ (1999) J Catal 183:281

    Article  CAS  Google Scholar 

  42. Wang X, Xu H, Fu X, Liu P, Lefebvre F, Basset JM (2005) J Mol Catal A: Chem 238:185

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Catalysis Division, National Chemical Laboratory (CSIR), Pune, 411008, India

    P. S. Niphadkar, P. N. Joshi, H. R. Gurav, S. S. Deshpande & V. V. Bokade

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  1. P. S. Niphadkar
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  2. P. N. Joshi
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  3. H. R. Gurav
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  4. S. S. Deshpande
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  5. V. V. Bokade
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Correspondence to V. V. Bokade.

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Niphadkar, P.S., Joshi, P.N., Gurav, H.R. et al. Synthesis of N-methylaniline by Aniline Alkylation with Methanol over Sn-MFI Molecular Sieve. Catal Lett 133, 175–184 (2009). https://doi.org/10.1007/s10562-009-0143-4

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  • DOI: https://doi.org/10.1007/s10562-009-0143-4

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