Skip to main content
Log in

Mont-K10 Supported Fe(II) Schiff-Base Complex as an Efficient Catalyst for Hydrogenation of Ketones

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

A new Fe(II) Schiff base complex anchored on mont-K10 (Fe@imine-mont-K10) was synthesized and extensively characterized by FTIR, powder X-ray diffraction, SEM–EDX, TEM, ESR, X-ray photoelectron spectroscopy (XPS), BET surface area measurement, solid state 29Si NMR and ICP-AES analysis. The catalytic activity of the complex was investigated for hydrogenation of ketones. The results indicated that it exhibited good catalytic activity for hydrogenation of aromatic as well as aliphatic ketones in i-PrOH/CH3CN (1:1) using Na-i-OPr as base at 80 °C resulting in moderate to excellent isolated yields (51–99%) of their corresponding products. The catalyst shows good reusability.

Graphical Abstract

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 2

Similar content being viewed by others

References

  1. Çalık HS, Ispir E, Karabuga S, Aslantas M (2016) J Organomet Chem 801:122

    Article  CAS  Google Scholar 

  2. Foubelo F, Najera C, Yus M (2015) Tetrahedron 26:769

    Article  CAS  Google Scholar 

  3. Margalef J, Pàmies O, Diéguez M (2016) Tetrahedron Lett 57:1301

    Article  CAS  Google Scholar 

  4. Zhou L, Gu H, Yan X (2009) Catal Lett 132:16

    Article  CAS  Google Scholar 

  5. Saluzzo C, Lemaire M (2002) Adv Synth Catal 344:915

    Article  CAS  Google Scholar 

  6. Wang B, Li C, He B, Qi J, Liang C (2017) J Energy Chem 26:799

    Article  CAS  Google Scholar 

  7. Magubane MN, Alam MG, Ojwach SO, Munro OQ (2017) J Mol Struct 1135:197

    Article  CAS  Google Scholar 

  8. Baysal A, Karakas DE, Meric N, Ak B, Aydemir M, Durap F (2017) Transit Met Chem 42:365

    Article  CAS  Google Scholar 

  9. Pattanayak P, Parua SP, Patra D, Lai CK, Brandao P, Felix V, Chattopadhyay S (2015) Inorg Chim Acta 429:122

    Article  CAS  Google Scholar 

  10. Olguín J, Sandoval MAP (2017) J Organomet Chem 848:309

    Article  CAS  Google Scholar 

  11. Oruç ZI, Gok L, Türkmen H, Sahin O, Büyükgüngor O, Çetinkaya B (2016) J Organomet Chem 807:36

    Article  CAS  Google Scholar 

  12. Sharma S, Kumar M, Nayal OS, Thakur MS, Bhatt V, Kumar N, Singh B, Sharma U (2016) Asian J Org Chem 5:1471

    Article  CAS  Google Scholar 

  13. Aydemir M, Meric N, Kayan C, Ok F, Baysal A (2013) Inorg Chim Acta 398:1

    Article  CAS  Google Scholar 

  14. Albrecht M, Crabtree RH, Mata J, Peris E (2002) Chem Commun. https://doi.org/10.1039/B109491B

    Article  Google Scholar 

  15. Shen Y, Chen Q, Lou LL, Yu K, Ding F, Liu S (2010) Catal Lett 137:104

    Article  CAS  Google Scholar 

  16. Landaeta VR, Rosa ADSL, Lugo RER (2018) Inorg Chim Acta 470:303

    Article  CAS  Google Scholar 

  17. Ramasamy B, Gangwar MK, Ghosh P (2017) Eur J Inorg Chem 2017:3253

    Article  CAS  Google Scholar 

  18. He L, Ni J, Wang LC, Yu FJ, Cao Y, He HY, Fan KN (2009) Chem Eur J 15:11833

    Article  CAS  PubMed  Google Scholar 

  19. Su FZ, He L, Ni J, Cao Y, He HY, Fan KN (2008) Chem Commun 0:3531

    Article  CAS  Google Scholar 

  20. Alonso F, Riente P, Reinoso FR, Martínez JR, Escribano AS, Yus M (2008) J Catal 260:113

    Article  CAS  Google Scholar 

  21. Alonso F, Riente P, Reinoso FR, Martínez JR, Escribano AS, Yus M (2009) Chem Cat Chem 1:75

    CAS  Google Scholar 

  22. Gracia MJ, Campelo JM, Losada E, Luque R, Marinas JM, Romero AA (2009) Org Biomol Chem 7:4821

    Article  CAS  PubMed  Google Scholar 

  23. Kilic A, Kaya İH, Ozaslan I, Aydemir M, Durap F (2018) Catal Commun 111:42

    Article  CAS  Google Scholar 

  24. Gupta KC, Sutar AK (2008) Coord Chem Rev 252:1420

    Article  CAS  Google Scholar 

  25. Pretorius R, Mazloomi Z, Albrecht M (2017) J Organomet Chem 845:196

    Article  CAS  Google Scholar 

  26. Suganthy PK, Prabhu RN, Sridevi VS (2015) Polyhedron 88:57

    Article  CAS  Google Scholar 

  27. Toubiana J, Medina L, Sasson Y (2014) Mod Res Catal 3:68

    Article  CAS  Google Scholar 

  28. Zeng L, Wu F, Li YY, Dong ZR, Gao JX (2014) J Organomet Chem 762:34

    Article  CAS  Google Scholar 

  29. Dayan S, Ozpozan NK, Ozdemir N, Dayan O (2014) J Organomet Chem 770:21

    Article  CAS  Google Scholar 

  30. Sonnenberg JF, Coombs N, Dube PA, Morris RH (2012) J Am Chem Soc 134:5893

    Article  CAS  PubMed  Google Scholar 

  31. He R, Cui P, Pi D, Sun Y, Zhou H (2017) Tetrahedron Lett 58:3571

    Article  CAS  Google Scholar 

  32. Mezzetti A (2017) Isr J Chem 57:1

    Article  CAS  Google Scholar 

  33. Smith SAM, Prokopchuk DE, Morris RH (2017) Isr J Chem 57:1

    Article  CAS  Google Scholar 

  34. Gong W, Chen C, Fan R, Zhang H, Wang G, Zhao H (2018) Fuel 231:165

    Article  CAS  Google Scholar 

  35. Perez M, Elangovan S, Spannenberg A, Junge K, Beller M (2016) Chem Sus Chem 9:1

    Article  Google Scholar 

  36. Wang D, Voisine AB, Sortais JB (2018) Catal Commun 105:31

    Article  CAS  Google Scholar 

  37. Kumar BS, Amali AJ, Pitchumani K (2018) Molecular Catal 448:153

    Article  CAS  Google Scholar 

  38. Li YY, Yu SL, Shen WY, Gao JX (2015) Acc Chem Res 48:2587

    Article  CAS  PubMed  Google Scholar 

  39. Nagashima H (2017) Bull Chem Soc Jpn 90:761

    Article  CAS  Google Scholar 

  40. Arai M, Zhao F (2015) Catalysts 5:868

    Article  CAS  Google Scholar 

  41. Gupta KC, Sutar AK (2007) J Mol Catal A: Chem 272:64

    Article  CAS  Google Scholar 

  42. Parida KM, Sahoo M, Singha S (2010) J Mol Catal A 329:7

    Article  CAS  Google Scholar 

  43. Singha S, Sahoo M, Parida KM (2011) Dalton Trans 40:11838

    Article  CAS  PubMed  Google Scholar 

  44. Sahoo M, Parida KM (2018) Chemistry Select 3:3092

    CAS  Google Scholar 

  45. Parida KM, Sahoo M, Singha S (2010) J Catal 276:161

    Article  CAS  Google Scholar 

  46. Wang R, Wang J, Zi H, Xia Y, Wang H, Liu X (2017) Mol Catal 441:168

    Article  CAS  Google Scholar 

  47. Bata P, Zsigmond A, Gyemant M, Czegledi A, Kluson P (2015) Res Chem Intermed 41:9281

    Article  CAS  Google Scholar 

  48. Bata P, Notheisz F, Kluson P, Zsigmond A (2015) Appl Organometal Chem 29:45

    Article  CAS  Google Scholar 

  49. Molla RA, Roy AS, Ghosh K, Salam N, Iqubal MA, Tuhina K, Islam SM (2015) J Organomet Chem 776:170

    Article  CAS  Google Scholar 

  50. Xu D, Zhou ZM, Dai L, Tang LW, Zhang J (2015) Bioorg Med Chem Lett 25:1961

    Article  CAS  PubMed  Google Scholar 

  51. Patil NM, Sasaki T, Bhanage BM (2016) ACS Sustain Chem Eng 4:429

    Article  CAS  Google Scholar 

  52. Hudson R, Chazelle V, Bateman M, Roy R, Li CJ, Moores A (2015) ACS Sustain Chem Eng 3:814

    Article  CAS  Google Scholar 

  53. Zhang JF, Zhong R, Zhou Q, Hong X, Huang S, Cui HZ, Hou XF (2017) Chem Cat Chem 9:2496

    CAS  Google Scholar 

  54. Azua A, Finn MT, Yi H, Dantas AB, Kostal AMV (2017) ACS Sustain Chem Eng 5:3963

    Article  CAS  Google Scholar 

  55. Tao F (2014) Metal Nanoparticles for Catalysis: Advances and Applications, RSc Catalysis Series No. 17, ISSN-1757-6725, Royal Society of Chemistry

  56. Farias M, Martinelli M, Rolim GK (2011) Appl Catal A 403:119

    Article  CAS  Google Scholar 

  57. Yadav GD (2005) Catal Surv Asia 9:117

    Article  CAS  Google Scholar 

  58. Kaur N, Kishore D (2012) J Chem Pharm Res 4:991

    CAS  Google Scholar 

  59. Huang TK, Wang R, Shi L, Lu X (2008) Catal Commun 9:1143

    Article  CAS  Google Scholar 

  60. Parida KM, Varadwaj GBB, Sahu S, Sahoo PC (2011) Ind Eng Chem Res 50:7849

    Article  CAS  Google Scholar 

  61. Varadwaj GBB, Sahu S, Parida KM (2011) Ind Eng Chem Res 50:8973

    Article  CAS  Google Scholar 

  62. Barros VP, Faria AL, MacLeod TCO, Moraes LAB, Assis MD (2008) Int Biodeterior Biodegradation 61:337

    Article  CAS  Google Scholar 

  63. Gogoi N, Bordoloi P, Borah G, Gogoi PK (2017) Catal Lett 147:539

    Article  CAS  Google Scholar 

  64. Sultana S, Borah G, Gogoi PK (2018) Appl Organometal Chem 1:1–10. https://doi.org/10.1002/aoc.4595

    Article  CAS  Google Scholar 

  65. Saikia PK, Sarmah PP, Borah BJ, Saikia L, Dutta DK (2016) J Mol Catal A 412:27

    Article  CAS  Google Scholar 

  66. Ahangaran F, Hassanzadeh A, Nouri S (2013) Int Nano Lett 3:23

    Article  CAS  Google Scholar 

  67. Moosvi SK, Majid K, Ara T (2016) Mat Res 19:983

    Article  Google Scholar 

  68. Huang G, Zhang C, Long Y, Wynn J, Liu Y, Wang W, Gao J (2013) Nanotechnology 24:395601. https://doi.org/10.1088/0957-4484/24/39/395601

    Article  CAS  PubMed  Google Scholar 

  69. Bhattacharyya KG, Gupta SS (2006) Sep Purif Technol 50:388

    Article  CAS  Google Scholar 

  70. Verma S, Baig RBN, Nadagouda MN, Varma RS (2016) Green Chem 18:1327

    Article  CAS  Google Scholar 

  71. Baltrusaitis J, Cwiertny DM, Grassian VH (2007) Phys Chem Chem Phys 9:5542

    Article  CAS  PubMed  Google Scholar 

  72. Wang X, Wu G, Wei W, Sun Y (2010) Catal Lett 136:96

    Article  CAS  Google Scholar 

  73. Magubane MN, Nyamato GS, Ojwach SO, Munro OQ (2016) RSC Adv 6:65205

    Article  CAS  Google Scholar 

  74. Wang F, Zhang Z (2017) ACS Sustain Chem Eng 5:942

    Article  CAS  Google Scholar 

  75. Li J, Liu J, Zhou H, Fu Y (2016) Chemsuschem 9:1339

    Article  CAS  PubMed  Google Scholar 

  76. Bala MD, Ikhile MI (2014) J Mol Catal A 385:98

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors thank SAIF, IIT Bombay for ESR and ICP-AES facilities, SAIF, NEHU, Shillong for TEM and 1H-NMR facilities, SAIF, IISC Bangalore for 29Si NMR facilities, SAIF, STIC, Kochi University, Kochi for 1H-NMR facilities, ACMS, IIT Kanpur for X-ray photoelectron spectroscopic facilities and BIT, Bangalore for BET surface area measurement facilities. S. Sultana gratefully thanks UGC-SAP-DRS-I programme (2016-2021) and UGC-Maulana Azad National Fellowship, Delhi for financial support.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Geetika Borah or Pradip. K. Gogoi.

Ethics declarations

Conflict of interest

The authors declare that there is no conflict of interests regarding the publication of this article.

Additional information

Publisher's Note

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

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 3293 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sultana, S., Borah, G. & Gogoi, P.K. Mont-K10 Supported Fe(II) Schiff-Base Complex as an Efficient Catalyst for Hydrogenation of Ketones. Catal Lett 149, 2142–2157 (2019). https://doi.org/10.1007/s10562-019-02810-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-019-02810-x

Keywords

Navigation