Reaction Kinetics, Mechanisms and Catalysis
Volume/Issue:
Volume 107: Issue 2
Cu(II) Schiff base complexes on montmorillonite as nano-reactor heterogeneous catalysts for the epoxidation of cyclooctene: synthesis, characterization and immobilization
Authors:
Abolfazl Bezaatpour Department of Chemistry, Faculty of Basic Science, University of Mohaghegh Ardabili 179, Ardabil, Iran

Search for other papers by Abolfazl Bezaatpour in
Current site
Google Scholar
PubMed Close
,
Mahdi Behzad Department of Chemistry, Semnan University, Semnan, Iran

Search for other papers by Mahdi Behzad in
Current site
Google Scholar
PubMed Close
,
Vahdat Jahed Department of Chemistry, Semnan University, Semnan, Iran

Search for other papers by Vahdat Jahed in
Current site
Google Scholar
PubMed Close
,
Mandana Amiri Department of Chemistry, Faculty of Basic Science, University of Mohaghegh Ardabili 179, Ardabil, Iran

Search for other papers by Mandana Amiri in
Current site
Google Scholar
PubMed Close
,
Yaghoub Mansoori Department of Chemistry, Faculty of Basic Science, University of Mohaghegh Ardabili 179, Ardabil, Iran

Search for other papers by Yaghoub Mansoori in
Current site
Google Scholar
PubMed Close
,
Zahra Rajabalizadeh Department of Chemistry, Faculty of Basic Science, University of Mohaghegh Ardabili 179, Ardabil, Iran

Search for other papers by Zahra Rajabalizadeh in
Current site
Google Scholar
PubMed Close
, and
Somayeh Sarvi Department of Chemistry, Faculty of Basic Science, University of Mohaghegh Ardabili 179, Ardabil, Iran

Search for other papers by Somayeh Sarvi in
Current site
Google Scholar
PubMed Close
Pages:
367–381
Online Publication Date:
19 Jul 2012
Publication Date:
01 Dec 2012
Article Category:
Research Article
DOI:
https://doi.org/10.1007/s11144-012-0474-9
Keywords:
Heterogeneous catalyst; Immobilization; Schiff base; Epoxidation; Montmorillonite
Restricted access

Abstract

Cu(II) tetradentate Schiff base complexes of N,N′-(bis(pyridin-2-yl)formylidene)ethane-1,2-diamine (pfed), N,N′-(bis(pyridin-2-yl)formylidene)propane-1,3-diamine (pfpd), N,N′-(bis(pyridin-2-yl)formylidene)benzene-1,2-diamine (pfbd), N,N′-(bis(pyridin-2-yl)formylidene)cycohexane-1,2-diamine (pfcd) and N,N′-(bis(pyridin-2yl)formylidene)meso-stilben-1,2-diamine (pfmd) were synthesized, characterized and immobilized on sodium montmorillonite. These catalysts were characterized by X-ray diffraction, IR spectroscopy, diffuse reflectance spectra (DRS) and atomic absorption spectroscopy. The IR and DRS data of the heterogeneous catalysts show that copper(II) complexes were physically entrapped within sodium montmorillonite. The basal spacing (d001) of heterogeneous catalysts indicates that Cu(II) Schiff base complexes were fixed in the axial direction into the interlayer of montmorillonite. All new heterogeneous catalysts show excellent catalytic activity in the epoxidation of cyclooctene using tert-butylhydroperoxide in acetonitrile. The supported [Cu(pfed)] exhibited a moderate 74 % selectivity for epoxidation with 76 % conversion. The catalytic activity and selectivity of heterogeneous catalysts have not changed after three times of reusing.

  • 1. Puzari, A, Baruah, JB 2002 J Mol Catal A Chem 187:149–162 .

  • 2. Jiang, J, Li, R, Wang, H, Zheng, Y, Chen, H, Ma, J 2008 Catal Lett 120:221–228 .

  • 3. Jiang, J, Ma, K, Zheng, Y, Cai, S, Li, R, Ma, J 2009 Appl Clay Sci 45:117–122 .

  • 4. Boghaei, DM, Bezaatpour, A, Behzad, M 2006 J Mol Catal A Chem 245:12–16 .

  • 5. Palucki, M, McCormick, GJ, Jacobsen, EN 1995 Tetrahedron Lett 36:5457–5460.

  • 6. Zhou, X, Shearer, J, Rokita, SE 2000 J Am Chem Soc 122:9046–9047 .

  • 7. Linker, T 1997 Angew Chem Int Ed Engl 38:2060–2062 .

  • 8. Zhang, W, Loebach, JL, Wilson, SR, Jacobsen, EN 1990 J Am Chem Soc 112:2801–2803 .

  • 9. Tsuchida, E, Oyaizu, K 2003 Coord Chem Rev 237:213–228 .

  • 10. Zhang, W, Jacobsen, EN 1991 J Org Chem 56 7 2296–2298 .

  • 11. Musie, GT, Wei, M, Subramaniam, B, Busch, DH 2001 Inorg Chem 40:3336–3341 .

  • 12. Salavati-Niasari, M, Zamani, E, Bazarganipour, M 2007 Appl Clay Sci 38:9–16 .

  • 13. Fan, QH, Li, YM, Chan, ASC 2002 Chem Rev 102:3385–3466 .

  • 14. Nones, CD, Pillinger, M, Valente, A, Goncalves, IS 2003 Inorg Chem Commun 6:1228–1233 .

  • 15. McNamara, CA, Dixion, MJ, Bradely, M 2002 Chem Rev 102:3275–3300 .

  • 16. Baleizão, C, Gigante, B, Das, D, Álvaro, M, Garcia, H, Corma, A 2004 J Catal 223:106–113 .

  • 17. Imamura, S, Sakai, H, Shono, M, Kanai, H 1998 J Catal 177:72–81 .

  • 18. Bekkum, HV, Vander Waal, JC 1997 J Mol Catal A Chem 124:137–146 .

  • 19. Rigutto, MS, Bekkum, HV 1993 J Mol Catal 81:77–98 .

  • 20. Brunner, H, Stumpf, A 1994 Monatsh Chem 125:485–489 .

  • 21. Gupta, KC, Abdulkadir, HK, Chand, S 2003 J Mol Catal A Chem 202:253–268 .

  • 22. Corma, A, Fuerte, A, Iglesias, M, Sanchez, F 1996 J Mol Catal A Chem 107:225–234 .

  • 23. Bezaatpour, A, Amiri, M, Jahed, V 2011 J Coord Chem 64:1837–1847 .

  • 24. Gao, J, Lu, L, Zhou, W, Gao, G, He, M 2008 J Porous Mater 15:127–132 .

  • 25. Zamanifar, E, Farzaneh, F 2011 React Kinet Mech Catal 104:197–209 .

  • 26. Boghaei, DM, Behzad, M, Bezaatpour, A 2005 J Mol Catal A Chem 241:1–7 .

  • 27. Frisch, MJ, Trucks, GW, Schlegel, HB, Scuseria, GE, Robb, MA, Cheeseman, JR, Montgomery, JA, Vreven, T, Kudin, KN, Burant, JC, Millam, JM, Iyengar, SS, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, GA, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kilao, O, Nakai, H, Klene, M, Li, X, Knox, JE, Hratchian, HP, Cross, JB, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, RE, Yazyev, O, Austin, AJ, Cammi, R, Pomelli, C, Ochterski, JW, Ayala, PY, Morokuma, K, Voth, GA, Salvador, P, Dannenberg, JJ, Zakrzewski, VG, Dapprich, S, Daniels, AD, Strain, MC, Farkas, O, Malick, DK, Rabuck, AD, Raghavachari, K, Foresmnn, JB, Ortiz, JV, Cui, Q, Baboul, AG, Clifford, S, Cioslowski, J, Stefanov, BB, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Martin, RL, Fox, DJ, Keith, T, Al-Laham, MA, Peng, CY, Nanayakkara, A, Challacombe, M, Gill, PMW, Johnson, B, Chen, W, Wong, MW, Gonzalez, C, Pople, JA 2003 GAUSSIAN03 revB.2 Gaussian Inc. Pittsburgh.

    • Search Google Scholar
    • Export Citation

  • 28. Irving, MNH, Parkins, RM 1965 J Inorg Nucl Chem 27:270–271 .

  • 29. Ray, MS, Bhattacharya, R, Chaudhuri, S, Righi, L, Bocelli, G, Mukhopadhyay, G, Ghosh, A 2003 Polyhedron 22:617–624 .

  • 30. Chiswell, B 1975 Inorg Chim Acta 12:195–198 .

  • 31. Geary, WJ 1971 Coord Chem Rev 7:81–122 .

  • 32. Lange, J, Elias, H, Paulus, H 2000 Inorg Chem 39:3342–3349 .

  • 33. Borah, M, Ganguli, JN, Dutta, DK 2001 J Colloid Interface Sci 233:171–179 .

  • 34. Sheldon, RA, Kochi, JK 1981 Metal catalyzed oxidations of organic compounds Academic Press New York.

  • Collapse
  • Expand
Cover Reaction Kinetics, Mechanisms and Catalysis
Reaction Kinetics, Mechanisms and Catalysis
Print ISSN:
1878-5190
Online ISSN:
1878-5204

To see the editorial board, please visit the website of Springer Nature.

Manuscript submission: www.editorialmanager.com/reac

For subscription options, please visit the website of Springer Nature.

Reaction Kinetics, Mechanisms and Catalysis
Language English
Size B5
Year of
Foundation		 1974
Volumes
per Year		 1
Issues
per Year		 6
Founder Akadémiai Kiadó
Founder's
Address		 H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
Publisher Akadémiai Kiadó
Springer Nature Switzerland AG
Publisher's
Address		 H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
CH-6330 Cham, Switzerland Gewerbestrasse 11.
Responsible
Publisher		 Chief Executive Officer, Akadémiai Kiadó
ISSN 1878-5190 (Print)
ISSN 1878-5204 (Online)

Monthly Content Usage

Abstract Views Full Text Views PDF Downloads
Apr 2024 14 0 0
May 2024 10 0 0
Jun 2024 14 0 0
Jul 2024 14 0 0
Aug 2024 35 0 0
Sep 2024 59 0 0
Oct 2024 41 0 0