Research on Chemical Intermediates

, Volume 45, Issue 5, pp 2999–3018 | Cite as

Synthesis, characterization and application of nano-N,N,N′,N′-tetramethyl-N-(silica-n-propyl)-N′-sulfo-ethane-1,2-diaminium chloride as a highly efficient catalyst for the preparation of N,N′-alkylidene bisamides

  • Abdolkarim ZareEmail author
  • Masoud Sadeghi-Takallo
  • Mostafa Karami
  • Alireza Kohzadian


A novel mesoporous nanomaterial, namely nano-N,N,N′,N′-tetramethyl-N-(silica-n-propyl)-N′-sulfo-ethane-1,2-diaminium chloride (nano-[TSPSED][Cl]2), was prepared, and characterized using Fourier-transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDS), field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), adsorption/desorption porosimetry (BET, Langmuir, BJH and adsorption/desorption isotherm), thermal gravimetric (TG), differential thermal gravimetric (DTG) and X-ray diffraction (XRD) analyses. Afterward, nano-[TSPSED][Cl]2 was used as a highly efficient and recyclable nanocatalyst for the condensation reaction of primary amides (2 eq.) with arylaldehydes (1 eq.) under solvent-free conditions to afford N,N′-alkylidene bisamides in high yields and in short times.

Graphical abstract


Mesoporous nanocatalyst Silica-based nanocatalyst Nano-N,N,N′,N′-tetramethyl-N-(silica-n-propyl)-N′-sulfo-ethane-1,2-diaminium chloride (nano-[TSPSED][Cl]2N,N′-alkylidene bisamide Solvent-free 



The authors gratefully acknowledge support of this work by Payame Noor University.

Supplementary material

11164_2019_3775_MOESM1_ESM.docx (506 kb)
The online version of this article ( contains supplementary material (the BET, Langmuir, BJH and adsorption–desorption isotherm plots of the used nano-silica for the preparation of nano-[TSPSED][Cl]2, and selected spectral data and original spectra of N,N′-alkylidene bisamides), which are available to authorized users (DOCX 506 kb)


  1. 1.
    M. Rauchdi, M.A. Ali, A. Roucoux, Appl. Catal. A: Gen. 550, 266 (2018)CrossRefGoogle Scholar
  2. 2.
    S. Nazarzadeh, A. Ghorbani-Choghamarani, E. Tahanpesar, J. Iran. Chem. Soc. 15, 649 (2018)CrossRefGoogle Scholar
  3. 3.
    Y.K. Tailor, S. Khandelwal, R. Gopal, E. Rushell, A. Prajapati, M. Kumar, ChemistrySelect 2, 11055 (2017)CrossRefGoogle Scholar
  4. 4.
    G.T. Reddy, G. Kumar, N.C.G. Reddy, Adv. Synth. Catal. 360, 995 (2018)CrossRefGoogle Scholar
  5. 5.
    Z. Hamidi, M.A.K. Zarchi, Res. Chem. Intermed. 44, 6995 (2018)CrossRefGoogle Scholar
  6. 6.
    A. Ramazani, P.A. Asiabi, H. Aghahosseini, F. Gouranlou, Curr. Org. Chem. 21, 908 (2017)CrossRefGoogle Scholar
  7. 7.
    E. Soleimani, M. Naderi Namivandi, H. Sepahvand, Appl. Organomet. Chem. 31, 3566 (2017)CrossRefGoogle Scholar
  8. 8.
    A. Zare, M. Merajoddin, A.R. Moosavi-Zare, M. Zarei, M.H. Beyzavi, M.A. Zolfigol, Res. Chem. Intermed. 42, 2365 (2016)CrossRefGoogle Scholar
  9. 9.
    R. Hosseinzadeh-Khanmiri, Y. Kamel, Z. Keshvari, A. Mobaraki, G.H. Shahverdizadeh, E. Vessally, M. Babazadeh, Appl. Organomet. Chem. 32, 4452 (2018)CrossRefGoogle Scholar
  10. 10.
    A. Khazaei, N. Sarmasti, J.Y. Seyf, J. Mol. Liq. 262, 484 (2018)CrossRefGoogle Scholar
  11. 11.
    M. Shekouhy, A. Moaddeli, A. Khalafi-Nezhad, J. Ind. Eng. Chem. 50, 41 (2017)CrossRefGoogle Scholar
  12. 12.
    A. Zare, A. Kohzadian, Z. Abshirini, S.S. Sajadikhah, J. Phipps, M. Benamarad, M.H. Beyzavi, New J. Chem. 43, 2247 (2019)CrossRefGoogle Scholar
  13. 13.
    M. Himaja, D. Poppy, K. Asif, Int. J. Res. Ayurveda Pharm. 2, 1079 (2011)Google Scholar
  14. 14.
    A.R. Moosavi-Zare, M.A. Zolfigol, S. Farahmand, A. Zare, A.R. Pourali, R. Ayazi-Nasrabadi, Synlett 25, 193 (2014)CrossRefGoogle Scholar
  15. 15.
    F. Tamaddon, D. Azadi, J. Mol. Liq. 255, 406 (2018)CrossRefGoogle Scholar
  16. 16.
    N. Irannejad-Gheshlaghchaei, A. Zare, S.S. Sajadikhah, A. Banaei, Res. Chem. Intermed. 44, 6253 (2018)CrossRefGoogle Scholar
  17. 17.
    D. Jaiswal, A. Mishra, P. Rai, M. Srivastava, B.P. Tripathi, S. Yadav, J. Singh, J. Singh, Res. Chem. Intermed. 44, 231 (2018)CrossRefGoogle Scholar
  18. 18.
    C.L. Allen, J.M. Williams, Chem. Soc. Rev. 40, 3405 (2011)CrossRefGoogle Scholar
  19. 19.
    X.-L. Wang, X.-T. Sha, G.-C. Liu, N.-L. Chen, Y. Tian, CrystEngComm 17, 7290 (2015)CrossRefGoogle Scholar
  20. 20.
    M.-N. Chang, X.-K. Yang, P.M. Chhetri, J.-D. Chen, Polymers 9, 691 (2017)CrossRefGoogle Scholar
  21. 21.
    J.W. Bode, Curr. Opin. Drug Discov. Devel. 9, 765 (2006)Google Scholar
  22. 22.
    M. Rodriguez, P. Dubreuil, J.P. Bali, J. Martinez, J. Med. Chem. 30, 758 (1987)CrossRefGoogle Scholar
  23. 23.
    M. Goodman, H. Shao, Pure Appl. Chem. 68, 1303 (1996)CrossRefGoogle Scholar
  24. 24.
    T. Yamazaki, K.I. Nunami, M. Goodman, Biopolymers 31, 1513 (1991)CrossRefGoogle Scholar
  25. 25.
    J.P. Wan, Y.F. Chai, J.M. Wu, Y.J. Pan, Synlett 19, 3068 (2008)Google Scholar
  26. 26.
    K. Selvakumar, T. Shanmugaprabha, M. Kumaresan, P. Sami, Synth. Commun. 47, 2115 (2017)CrossRefGoogle Scholar
  27. 27.
    H.R. Saadati-Moshtaghin, F.M. Zonoz, M.M. Amini, J. Solid State Chem. 260, 16 (2018)CrossRefGoogle Scholar
  28. 28.
    T.L. Lambat, S.S. Deo, F.S. Inam, T.B. Deshmukh, A.R. Bhat, Karbala Int. J. Modern Sci. 2, 63 (2016)CrossRefGoogle Scholar
  29. 29.
    B. Maleki, M. Baghayeri, RSC Adv. 5, 79746 (2015)CrossRefGoogle Scholar
  30. 30.
    B. Maleki, F.M. Zonoz, H.A. Akhlaghi, Org. Prep. Proced. Int. 47, 361 (2015)CrossRefGoogle Scholar
  31. 31.
    B.F. Mirjalili, M.A. Mirhoseini, J. Chem. Sci. 125, 1481 (2013)CrossRefGoogle Scholar
  32. 32.
    G. Ramachandran, R. Saraswathi, M. Kumarraja, P. Govindaraj, T. Subramanian, Synth. Commun. 48, 216 (2018)CrossRefGoogle Scholar
  33. 33.
    A. Mouradzadegun, S. Elahi, F. Abadast, RSC Adv. 4, 31239 (2014)CrossRefGoogle Scholar
  34. 34.
    M. Anary-Abbasinejad, M.H. Mosslemin, A. Hassanabadi, S.T. Safa, Synth. Commun. 40, 2209 (2010)CrossRefGoogle Scholar
  35. 35.
    G. Harichandran, S.D. Amalraj, P. Shanmugam, J. Iran. Chem. Soc. 8, 298 (2011)CrossRefGoogle Scholar
  36. 36.
    H.A. Soliman, A.Y. Mubarak, S.S. Elmorsy, Chin. Chem. Lett. 27, 353 (2016)CrossRefGoogle Scholar
  37. 37.
    K. Suzuki, K. Ikari, H. Imai, J. Am. Chem. Soc. 126, 462 (2004)CrossRefGoogle Scholar
  38. 38.
    P. Jal, M. Sudarshan, A. Saha, S. Patel, B. Mishra, Colloids Surf. A: Phys. Eng. Asp. 240, 173 (2004)CrossRefGoogle Scholar
  39. 39.
    E.C. Mansaneira, N. Schwantes-Cezario, G.F. Barreto-Sandoval, B. Martins-Toralles, DYNA 84, 163 (2017)CrossRefGoogle Scholar
  40. 40.
    Y. Miller, G.M. Chaban, J. Zhou, K.R. Asmis, D.M. Neumark, R.B. Gerber, J. Chem. Phys. 127, 094305 (2007)CrossRefGoogle Scholar
  41. 41.
    W. Förner, H.M. Badawi, Z. Naturforsch. 66b, 69 (2011)CrossRefGoogle Scholar
  42. 42.
    F. Scheinmann, An Introduction to Spectroscopic Methods for the Identification of Organic Compounds: mass Spectrometry, Ultraviolet Spectroscopy, Electron Spin Resonance Spectroscopy, Nuclear Magnetic Resonance Spectroscopy (Recent Developments), Use of Various Spectral Methods Together, and Documentation of Molecular Spectra (Elsevier, Amsterdam, 2013)Google Scholar
  43. 43.
    V.J. Kapoor, W.D. Brown (ed.), in Proceedings of the Third Symposium on Silicon Nitride and Silicon Dioxide Thin Insulating Films, (The Electrochemical Society, 1994)Google Scholar
  44. 44.
    C. Rao, R. Venkataraghavan, T. Kasturi, Can. J. Chem. 42, 36 (1964)CrossRefGoogle Scholar
  45. 45.
    A. Mourhly, M. Khachani, A.E. Hamidi, M. Kacimi, M. Halim, S. Arsalane, Nanomater. Nanotechnol. 5, 35 (2015)CrossRefGoogle Scholar
  46. 46.
    K. Antony, J.P. Davim, Advanced Manufacturing and Materials Science: Selected Extended Papers of ICAMMS 2018 (Springer, New York, 2018)CrossRefGoogle Scholar
  47. 47.
    L.D.S. Yadav, Organic Spectroscopy (Springer, Dordrecht, 2005)CrossRefGoogle Scholar
  48. 48.
    D.L. Pavia, G.M. Lampman, G.S. Kriz, J.A. Vyvyan, Introduction to Spectroscopy, 5th edn. (Cengage Learning, Belmont, 2014)Google Scholar
  49. 49.
    J. Safari, Z. Zarnegar, RSC Adv. 5, 17738 (2015)CrossRefGoogle Scholar
  50. 50.
    H. Tian, L. Pan, X. Xiao, R.W.T. Wilkins, Z. Meng, B. Huang, Mar. Pet. Geol. 48, 8 (2013)CrossRefGoogle Scholar
  51. 51.
    A. Biabani-Ravandi, M. Rezaei, Chem. Eng. J. 184, 141 (2012)CrossRefGoogle Scholar
  52. 52.
    M. Nikoorazm, A. Ghorbani-Choghamarani, M. Khanmoradi, Appl. Organomet. Chem. 30, 705 (2016)CrossRefGoogle Scholar
  53. 53.
    M. Nikoorazm, A. Ghorbani-Choghamarani, N. Noori, B. Tahmasbi, Appl. Organomet. Chem. 30, 843 (2016)CrossRefGoogle Scholar
  54. 54.
    R.E. Morsi, R.S. Mohamed, R. Soc, Open Sci. 5, 172021 (2018)Google Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of ChemistryPayame Noor UniversityTehranIran

Personalised recommendations