Skip to main content
SpringerLink
Log in

1,8-Diazabicyclo [5.4.0] undec-7-ene functionalized cellulose nanofibers as an efficient and reusable nanocatalyst for the synthesis of tetraketones in aqueous medium

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

1,8-Diazabicyclo [5.4.0] undec-7-ene functionalized cellulose nanofibers (CNF@DBU[Cl]) were simply prepared and characterized by analytical techniques. Scanning electron microscope confirmed that CNF@DBU[Cl] was formed with average size of 30–60 nm. X-ray diffraction of CNF@DBU[Cl] showed that the crystalline structure of the cellulose nanofibers was remained unchanged after functionalization. According to elemental analyses and thermal gravimetric analysis, the loading amount of organic group on cellulose nanofibers was found to be 1.46 mmol/g. The catalytic activity of DBU functionalized cellulose nanofibers was studied for the synthesis of biologically important tetraketone derivatives in the reaction of aldehydes with 1,3-dicarbonyl compounds. In the presence of CNF@DBU[Cl], the corresponding tetraketones were obtained in 80–96% yields under very mild reaction conditions. The catalyst was recovered and reused four successive runs without significant loss of catalytic activity. This method showed several significant advantages including short reaction times, high yields of products, use of various substrates, convenient work-up, no necessity of extraction or chromatographic purification steps, environmentally friendly conditions and lack of use of any harmful solvent.

Graphic abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. Q. Du, Y. Li, Beilstein J. Org. Chem. 7, 378 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. W. Yu, L. Jiang, C. Shen, W. Xu, P. Zhang, Catal. Commun. 79, 11 (2016)

    Article  CAS  Google Scholar 

  3. S. Hajar, MdS Islam, MdL Rahman, S.S. Rashid, Z.Z. Chowdhury, MdE Ali, S.M. Sarkar, Bioressources 12, 882 (2017)

    CAS  Google Scholar 

  4. MdS Islam, MdL Rahman, M.M. Yusoff, S.M. Sarkar, J. Clean. Prod. 149, 1045 (2017)

    Article  CAS  Google Scholar 

  5. D. Li, J. Zhang, C. Cai, J. Org. Chem. 83, 7534 (2018)

    Article  CAS  PubMed  Google Scholar 

  6. S. Shojaei, Z. Ghasemi, A. Shahrisa, Appl. Organomet. Chem. 31, e3788 (2017)

    Article  CAS  Google Scholar 

  7. P. Kaur, B. Kumar, V. Kumar, R. Kumar, Tetrahedron Lett. 59, 1986 (2018)

    Article  CAS  Google Scholar 

  8. H.P.S. Abdul Khalil, C.K. Saurabha, A.S. Adnan, M.R. Nurul Fazitaa, M.I. Syakira, Y. Davoudpour, M. Rafatullah, C.K. Abdullah, M.K.M. Haafiz, R. Dungani, Carbohydr. Polym. 150, 216 (2016)

    Article  CAS  Google Scholar 

  9. T. Baran, A. Mentes, J. Organomet. Chem. 803, 30 (2016)

    Article  CAS  Google Scholar 

  10. S. Keshipour, S.S. Mirmasoudi, Adv. Environ. Technol. 3, 59 (2017)

    Google Scholar 

  11. A. Matsuoka, T. Isogawa, Y. Morioka, B.R. Knappett, A.E.H. Wheatley, S. Saito, H. Naka, RSC Adv. 5, 12152 (2015)

    Article  CAS  Google Scholar 

  12. Y. Huang, Y. Fang, L. Chen, A. Lu, L. Zhang, Chem. Eng. J. 315, 573 (2017)

    Article  CAS  Google Scholar 

  13. Y. Cao, M. Tang, M. Li, J. Deng, F. Xu, L. Xie, Y. Wang, ACS Sustain. Chem. Eng. 5, 9894 (2017)

    Article  CAS  Google Scholar 

  14. K. Murali, M.S. Neelakandan, S. Thomas, JSM Nanotechnol. Nanomed 6(1), 1064 (2018)

    Google Scholar 

  15. L. Dykman, N. Khlebtsov, Chem. Soc. Rev. 41, 2256 (2012)

    Article  CAS  PubMed  Google Scholar 

  16. L. Chen, E. Hwang, J. Zhang, Sensors 18, 1440 (2018)

    Article  CAS  Google Scholar 

  17. MdR Awual, Chem. Eng. J. 307, 456 (2017)

    Article  CAS  Google Scholar 

  18. MdR Awual, G.E. Eldesoky, T. Yaita, M. Naushad, H. Shiwaku, Z.A. Alothman, S. Suzuki, Chem. Eng. J. 279, 639 (2015)

    Article  CAS  Google Scholar 

  19. A. Shahat, MdR Awual, M. Naushad, Chem. Eng. J. 271, 155 (2015)

    Article  CAS  Google Scholar 

  20. MdR Awual, Chem. Eng. J. 303, 539 (2016)

    Article  CAS  Google Scholar 

  21. MdR Awual, Chem. Eng. J. 300, 264 (2016)

    Article  CAS  Google Scholar 

  22. MdR Awual, T. Yaita, S. Suzuki, H. Shiwaku, J. Hazard. Mater. 291, 111 (2015)

    Article  CAS  PubMed  Google Scholar 

  23. MdR Awual, T. Yaita, H. Shiwaku, Chem. Eng. J. 228, 327 (2013)

    Article  CAS  Google Scholar 

  24. MdR Awual, T. Kobayashi, Y. Miyazaki, R. Motokawa, H. Shiwaku, S. Suzuki, Y. Okamoto, T. Yaita, J. Hazard. Mater. 252–253, 313 (2013)

    Article  PubMed  CAS  Google Scholar 

  25. MdR Awual, MdM Hasan, MdA Khaleque, MdC Sheikh, Chem. Eng. J. 288, 368 (2016)

    Article  CAS  Google Scholar 

  26. MdR Awual, Chem. Eng. J. 289, 65 (2016)

    Article  CAS  Google Scholar 

  27. MdR Awual, Chem. Eng. J. 307, 85 (2017)

    Article  CAS  Google Scholar 

  28. S. Duan, Zh Du, H. Fan, R. Wang, Nanomaterials 8, 949 (2018)

    Article  PubMed Central  CAS  Google Scholar 

  29. M. Kaushik, A. Moores, Green Chem. 18, 622 (2016)

    Article  CAS  Google Scholar 

  30. T. Nypelö, H. Pynnönen, M. Österberg, J. Paltakari, J. Laine, Cellulose 19, 779 (2012)

    Article  CAS  Google Scholar 

  31. T. Saito, A. Isogai, Carbohydr. Polym. 61, 183 (2005)

    Article  CAS  Google Scholar 

  32. K. Yoon, B.S. Hsiao, B. Chu, J. Mater. Chem. 18, 5326 (2008)

    Article  CAS  Google Scholar 

  33. I. Siro, D. Plackett, Cellulose 17, 459 (2010)

    Article  CAS  Google Scholar 

  34. H. Takagi, A. Asano, Compos. Part A Appl. Sci. Manuf. 39, 685 (2008)

    Article  CAS  Google Scholar 

  35. A. Isogai, T. Saito, H. Fukuzumi, Nanoscale 3, 71 (2011)

    Article  CAS  PubMed  Google Scholar 

  36. S. Iwamoto, A. Isogai, T. Iwata, Biomacromol 12, 831 (2011)

    Article  CAS  Google Scholar 

  37. Z. Ma, M. Kotaki, S. Ramakrishna, J. Membrane Sci. 265, 115 (2005)

    Article  CAS  Google Scholar 

  38. W. Chen, H. Yu, Y. Liu, Y. Hai, M. Zhang, P. Chen, Cellulose 18, 433 (2011)

    Article  CAS  Google Scholar 

  39. D. Klemm, T. Heinze, B. Philipp, W. Wagenknecht, Acta Polym. 48, 277 (1997)

    Article  CAS  Google Scholar 

  40. D. Roy, M. Semsarilar, J.T. Guthrie, S. Perrier, Chem. Soc. Rev. 38, 2046 (2009)

    Article  CAS  PubMed  Google Scholar 

  41. K.R. Reddy, N.S. Kumar, P.S. Reddy, B. Sreedhar, M.L. Kantam, J. Mol. Catal. A: Chem. 252, 12 (2006)

    Article  CAS  Google Scholar 

  42. C. Li, J. Wang, Zh Yang, Zh Hu, Z. Lei, Catal. Commun. 8, 1202 (2007)

    Article  CAS  Google Scholar 

  43. G.M. Maharvi, S. Ali, N. Riaz, N. Afza, A. Malik, M. Ashraf, L. Iqbal, M. Lateef, J. Enzyme Inhib. Med. Chem. 23, 62 (2008)

    Article  CAS  PubMed  Google Scholar 

  44. K.M. Khan, G.M. Maharvi, M.T.H. Khan, A. Jabbar Shaikh, S. Perveen, S. Begum, M.I. Choudhary, Bioorg. Med. Chem. 14, 344 (2006)

    Article  CAS  PubMed  Google Scholar 

  45. M. Saha, A.K. Pal, Tetrahedron Lett. 52, 4872 (2011)

    Article  CAS  Google Scholar 

  46. M. Brito-Arias, M. Tapia-Albarran, I. Padilla-Martınez, F. Martınez-Martınez, G. Espinosa, E. Molins, E. Espinosa, J. Chem. Crystallogr. 29, 759 (1999)

    Article  CAS  Google Scholar 

  47. A. Fallah, M. Tajbakhsh, H. Vahedi, A. Bekhradnia, Res. Chem. Intermed. 43, 29 (2017)

    Article  CAS  Google Scholar 

  48. T.S. Jin, A.Q. Wang, H. Ma, J. Zhang, T. Li, Indian J. Chem. B 45, 470 (2006)

    Google Scholar 

  49. A. Pramanik, S. Bhar, Catal. Commun. 20, 17 (2012)

    Article  CAS  Google Scholar 

  50. V.K. Rao, M.M. Kumar, A. Kumar, Indian J. Chem. Sec. B 50, 1128 (2011)

    Google Scholar 

  51. S. Kantevari, R. Bantu, L. Nagarapu, J. Mol. Catal. A: Chem. 269, 53 (2007)

    Article  CAS  Google Scholar 

  52. S. Ray, A. Bhaumik, M. Pramanik, R.J. Butcher, S.O. Yildirim, C. Mukhopadhyay, Catal. Commun. 43, 173 (2014)

    Article  CAS  Google Scholar 

  53. M. Gupta, M. Gupta, J. Chem. Sci. 128, 849 (2016)

    Article  CAS  Google Scholar 

  54. A. Ilangovan, S. Malayappasamy, S. Muralidharan, S. Maruthamuthu, Chem. Cent. J. 5, 1 (2011)

    Article  CAS  Google Scholar 

  55. G. Song, B. Wang, H. Luo, L. Yang, Catal. Commun. 8, 673 (2007)

    Article  CAS  Google Scholar 

  56. V. Rama, K. Kanagaraj, K. Pitchumani, Tetrahedron Lett. 53, 1018 (2012)

    Article  CAS  Google Scholar 

  57. M. Tajbakhsh, M. Heidary, R. Hosseinzadeh, Res. Chem. Intermed. 42, 1425 (2016)

    Article  CAS  Google Scholar 

  58. A.M. Akondi, M.L. Kantam, R. Trivedi, B. Sreedhar, S.K. Buddana, R.S. Prakasham, S. Bhargava, J. Mol. Catal. A: Chem. 386, 49 (2014)

    Article  CAS  Google Scholar 

  59. J.K. Rajput, G. Kaur, Catal. Sci. Technol. 4, 142 (2014)

    CAS  Google Scholar 

  60. M. Tajbakhsh, M. Farhang, H.R. Mardani, R. Hosseinzadeh, Y. Sarrafi, Chin. J. Catal. 34, 2217 (2013)

    Article  CAS  Google Scholar 

  61. M. Tajbakhsh, M. Farhang, R. Hosseinzadeh, Y. Sarrafi, RSC Adv. 4, 23116 (2014)

    Article  CAS  Google Scholar 

  62. M. Tajbakhsh, M. Bazzar, S.F. Ramzanian, M. Tajbakhsh, Appl. Clay Sci. 178, 88 (2014)

    Google Scholar 

  63. Y. Sarrafi, M. Sadatshahabi, K. Alimohammadi, M. Tajbakhsh, Green Chem. 13, 2851 (2011)

    Article  CAS  Google Scholar 

  64. Z. Lasemi, E. Mehrasbi, Res. Chem. Intermed. 41(2855–2866), 51 (2015)

    Google Scholar 

  65. J.T. Li, Y.W. Li, Y.L. Song, G.F. Chen, Ultrason. Sonochem. 19, 1 (2012)

    Article  PubMed  CAS  Google Scholar 

  66. J.J. Yu, L.M. Wang, J.Q. Liu, F.L. Guo, Y. Liu, N. Jiao, Green Chem. 12, 216 (2010)

    Article  CAS  Google Scholar 

  67. J.M. Khurana, K. Vij, J. Chem. Sci. 124, 907 (2012)

    Article  CAS  Google Scholar 

  68. M.R. Awual, J. Environ. Chem. Eng. 7, 103087 (2019)

    Article  CAS  Google Scholar 

  69. M.R. Awual, M.M. Hasan, M.A. Khaleque, Sens. Actuators B Chem. 209, 194 (2015)

    Article  CAS  Google Scholar 

  70. M.R. Awual, M.M. Hasan, J. Ind. Eng. Chem. 21, 507 (2015)

    Article  CAS  Google Scholar 

  71. M.R. Awual, M.M. Hasan, Sens. Actuators B Chem. 202, 395 (2014)

    Article  CAS  Google Scholar 

  72. M.R. Awual, T. Yaita, T. Taguchi, H. Shiwaku, Y. Okamoto, J. Hazard. Mater. 278, 227 (2014)

    Article  CAS  PubMed  Google Scholar 

  73. M.R. Awual, S. Suzuki, T. Taguchi, H. Shiwaku, T. Yaita, Chem. Eng. J. 242, 127 (2014)

    Article  CAS  Google Scholar 

  74. M.R. Awual, M.M. Hasan, H. Znad, Chem. Eng. J. 259, 611 (2015)

    Article  CAS  Google Scholar 

  75. M.R. Awual, T. Kobayashi, H. Shiwaku, Y. Miyazaki, T. Yaita, Chem. Eng. J. 225, 558 (2013)

    Article  CAS  Google Scholar 

  76. M.R. Awual, Mater. Sci. Eng. C 101, 686 (2019)

    Article  CAS  Google Scholar 

  77. M.R. Awual, J. Environ. Chem. Eng. 7, 103378 (2019)

    Article  CAS  Google Scholar 

  78. J. Bian, F. Peng, X.P. Peng, P. Peng, F. Xu, R.C. Sun, BioResources 7, 4626 (2012)

    Article  CAS  Google Scholar 

  79. S.G. Khokarale, J.P. Mikkola, RSC Adv. 8, 18531 (2018)

    Article  CAS  Google Scholar 

  80. K.Y. Lee, T. Tammelin, K. Schulfter, H. Kiiskinen, J. Samela, A. Bismarck, A.C.S. Appl, Mater. Interfaces 4, 4078 (2012)

    Article  CAS  Google Scholar 

  81. A. Fatoni, S. Koesnarpadi, N. Hidayati, Indones J. Chem. 15, 194 (2015)

    Article  CAS  Google Scholar 

  82. T.T.T. Ho, T. Zimmermann, R. Hauert, W. Caseri, Cellulose 18, 1391 (2011)

    Article  CAS  Google Scholar 

  83. V.K. Rao, M.M. Kumar, A. Kumar, Indian J. Chem. B 50, 1128 (2011)

    Google Scholar 

  84. A. Hasaninejad, N. Golzar, M. Beyrati, A. Zare, M.M. Doroodmand, J. Mole. Catal. A: Chem. 372, 137 (2013)

    Article  CAS  Google Scholar 

  85. F. Darviche, S. Balalaie, F. Chadegani, P. Salehi, Synth. Commun. 37, 1059 (2007)

    Article  CAS  Google Scholar 

  86. E.C. Horning, M.G. Horning, J. Org. Chem. 11, 95 (1946)

    Article  CAS  PubMed  Google Scholar 

  87. D.B. Ramachary, M. Kishor, J. Org. Chem. 72, 5056 (2007)

    Article  CAS  PubMed  Google Scholar 

  88. S. Khodabakhshi, M. Baghernejad, Iran. J. Catal. 3, 67 (2013)

    CAS  Google Scholar 

  89. M. Kidwai, V. Bansal, P. Mothsra, S. Saxena, R.K. Somvanshi, S. Dey, T.P. Singh, J. Mol. Catal. A: Chem. 268, 76 (2007)

    Article  CAS  Google Scholar 

  90. I. Manolov, C. Maichle-Moessmer, N. Danchev, Eur. J. Med. Chem. 41, 882 (2006)

    Article  CAS  PubMed  Google Scholar 

  91. S. Hasanzadeh Banakar, M.G. Dekamin, A. Yaghoubi, New J. Chem. 42, 14246 (2018)

    Article  CAS  Google Scholar 

  92. F. Nemati, M.M. Heravi, R. Saeedi Rad. Chin. J. Catal. 33, 1825 (2012)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We are grateful to University of Mazandaran for partial support of this work.

Author information

Authors and Affiliations

  1. Department of Chemistry, South Tehran Branch, Islamic Azad University, Tehran, Iran

    Zahra Lasemi

  2. Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, Iran

    Mahmood Tajbakhsh, Heshmatoallah Alinezhad & Forough Mehrparvar

Authors
  1. Zahra Lasemi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mahmood Tajbakhsh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Heshmatoallah Alinezhad
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Forough Mehrparvar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zahra Lasemi.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lasemi, Z., Tajbakhsh, M., Alinezhad, H. et al. 1,8-Diazabicyclo [5.4.0] undec-7-ene functionalized cellulose nanofibers as an efficient and reusable nanocatalyst for the synthesis of tetraketones in aqueous medium. Res Chem Intermed 46, 3667–3682 (2020). https://doi.org/10.1007/s11164-020-04167-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-020-04167-y

Keywords

Search

Navigation