Library Subscription: Guest
Begell Digital Portal Begell Digital Library eBooks Journals References & Proceedings Research Collections
Catalysis in Green Chemistry and Engineering

ISSN Print: 2572-9896
ISSN Online: 2572-990X

Catalysis in Green Chemistry and Engineering

DOI: 10.1615/CatalGreenChemEng.2020034489
pages 13-31

V2O5/HMS AS NOVEL CATALYST FOR PRODUCTION OF 1,1'-BI-2-NAPHTHOL BY OXIDATIVE C-C COUPLING OF 2-NAPHTHOL: ACTIVITY, SELECTIVITY AND KINETICS

Jeetendra Y. Salunke
Department of Chemical Engineering, Institute of Chemical Technology, Nathalal Parekh Marg, Matunga,Mumbai, 400 019, India
Ganapati D. Yadav
Department of Chemical Engineering, Institute of Chemical Technology, University of Mumbai, Nathalal Parekh Marg, Matunga, Mumbai 400019, India

ABSTRACT

Mesoporous materials such as hexagonal molecular sieve (HMS) can be used as supports for catalysis wherein bulky molecules are involved as reactants or products. The selective oxidative C-C coupling of 2-naphthol to 1,1'-bi-2-naphthol (BINOL) is a challenging reaction, and it was carried out using V2O5/HMS (V-HMS) as the catalyst and molecular oxygen as the oxidizing agent. BINOL is used as a ligand for asymmetric catalysis by transition metals. The redox nature of V2O5, high surface area, larger pore wall thickness, and high thermal stability makes V-HMS the best catalyst for synthesis of bulky BINOL. Different loadings of vanadium on HMS were studied, among which 4% V-HMS was the best. All synthesized and reused catalysts were characterized by TGA-DSC, XRD, H2-TPR, FT-IR, SEM-EDX, TEM, XPS, and BET analysis techniques. 2-Naphthol conversion and BINOL selectivity were 100%. A Mars van Krevelen−type mechanism was proposed, and a kinetic model was built for an oxidative coupling reaction. The apparent activation energy of the reaction system was 15.4 kcal/mol. The catalyst was used repeatedly without any significant loss in activity. The process is green.

REFERENCES

  1. Bhor, M.D., Nandurkar, N.S., Bhanushali, M.J., and Bhanage, B.M., An Efficient Oxidative Coupling of Naphthols Catalyzed by Fe Impregnated Pillared Montmorillonite K10, Catal. Lett., vol. 112, pp. 45-50, 2006.

  2. Bhor, M.D., Nandurkar, N.S., Bhanushali,M.J., and Bhanage, B.M., Ultrasound Promoted Selective Synthesis of 1,1'-Binaphthyls Catalyzed by Fe Impregnated Pillared Montmorillonite K10 in Presence of TBHP as an Oxidant, Ultrason. Sonochem., vol. 15, pp. 195-202, 2008.

  3. Brussee, J., Groenendijk, J.L.G., Koppele, J.M., and Jansen, A.C.A., On the Mechanism of the Formation of S(-)-(1, 1'-Binaphthalene)-2,2'-Diol via Copper(II)amine Complexes, Tetrahedron, vol. 41, pp. 3313-3319, 1985.

  4. Bulanek, R., Cicmanec, P., Sheng-Yang, H., Knotek, P., Capek, L., and Setnicka, M., Effect of Preparation Method on Nature and Distribution of Vanadium Species in Vanadium-Based Hexagonal Mesoporous Silica Catalysts: Impact on Catalytic Behavior in Propane ODH, Appl. Catal. A Gen., vols. 415-416, pp. 29-39, 2012.

  5. Chen, Y., Yekta, S., and Yudin, A.K., Modified BINOL Ligands in Asymmetric Catalysis, Chem. Rev., vol. 103, pp. 3155-3212, 2003.

  6. Devaraji, P., Sathu, N.K., and Gopinath, C.S., Ambient Oxidation of Benzene to Phenol by Photocatalysis on Au/Ti0.98V0.02O2: Role of Holes, ACS Catal., vol. 4, pp. 2844-2853, 2014.

  7. Doussot, J., Guy, A., and Ferroud, C., Selective Synthesis of 1,1'-Binaphthalene Derivatives by Oxidative Coupling with TiCl4, Tetrahedron Lett., vol. 41, pp. 2545-2547, 2000.

  8. Du, G., Lim, S., Pinault, M., Wang, C., Fang, F., Pfefferle, L., and Haller, G.L., Synthesis, Characterization, and Catalytic Performance of Highly Dispersed Vanadium Grafted SBA-15 Catalyst, J. Catal., vol. 253, pp. 74-90, 2008.

  9. Guo, Q.X., Wu, Z.J., Luo, Z.B., Liu, Q.Z., Ye, J.L., Luo, S.W., Cun, L.F., and Gong, L.Z., Highly Enantioselective Oxidative Couplings of 2-Naphthols Catalyzed by Chiral Bimetallic Oxovanadium Complexes with Either Oxygen or Air as Oxidant, J. Am. Chem. Soc., vol. 129, pp. 13927-13938, 2007.

  10. Ikeda, T.,Misawa, N., Ichihashi, Y., Nishiyama, S., and Tsuruya, S., Liquid-Phase Oxidative Coupling of 2-Naphthol by Vanadium Catalysts Supported on MCM-41, J. Mol. Catal. A Chem., vol. 231, pp. 235-240, 2005.

  11. Jana, S., Pande, S., Sinha,A.K., and Pal, T., Synthesis of Superparamagnetic B-MnO2 Organosol:A Photocatalyst for the Oxidative Phenol Coupling Reaction, Inorg. Chem., vol. 47, pp. 5558-5560, 2008.

  12. Joseph, J.K., Jain, S.L., and Sain, B., V2O5-O2 as a Simple and Efficient Protocol for the Oxidative Coupling of 2-Naphthols to Binaphthols under Mild Reaction Conditions, Catal. Commun., vol. 7, pp. 184-186, 2006.

  13. Keck, G.E., Li, X.Y., and Krishnamurthy, D., Catalytic Enantioselective Synthesis of Dihydropyrones via Formal Hetero Diels-Alder Reactions of "Danishefsky's Diene" with Aldehydes, J. Org. Chem., vol. 60, pp. 5998-5999, 1995.

  14. Kissinger, H.E., Reaction Kinetics in Differential Thermal Analysis, Anal. Chem., vol. 29, pp. 1702-1706, 1957.

  15. Liu, W., Lai, S.Y., Dai, H., Wang, S., Sun, H., and Au, C.T., Oxidative Dehydrogenation of N-\Butane over Mesoporous VOX /SBA-15 Catalysts, Catal. Lett., vol. 113, pp. 147-154, 2007.

  16. Love, B.E. and Bills, R.A., Facile Synthesis of BINOL in the Absence of Solvent, Synth. Commun., vol. 32, pp. 2067-2073, 2002.

  17. Mastrorilli, P., Muscio, F., Suranna, G.P., Nobile, C.F., and Latronico, M., Aerobic Oxidation of Substituted Phenols Catalysed by Metal Acetylacetonates in the Presence of 3-Methylbutanal, J. Mol. Catal. A Chem., vol. 165, pp. 81-87, 2001.

  18. Pisal, D.S. and Yadav, G.D., Synthesis of Salicylaldehyde through Oxidation of o-Cresol: Evaluation of Activity and Selectivity of Different Metals Supported on OMS-2 Nanorods and Kinetics, Mol. Catal., vol. 491, 2020. DOI: 10.1016/j.mcat.2020.110991.

  19. Rocha, G.M.S.R.O., Johnstone, R.A.W., and Neves, M.G.P.M.S., Catalytic Effects of Metal (IV) Phosphates on the Oxidation of Phenol and 2-Naphthol, J. Mol. Catal. A Chem., vol. 187, pp. 95-104, 2002.

  20. Roy, K., Vinod, C.P., and Gopinath, C.S., Design and Performance Aspects of a Custom-Built Ambient Pressure Photoelectron Spectrometer toward Bridging the Pressure Gap: Oxidation of Cu, Ag, and Au Surfaces at 1 Mbar O2 Pressure, J. Phys. Chem. C, vol. 117, pp. 4717-4726, 2013.

  21. Sakamoto, T., Yonehara, H., and Pac, C., Catalytic Activities of CuSO4/Al2O3 in Dehydrogenation of Arenes by Dioxygen, J. Org. Chem., vol. 62, pp. 3194-3199, 1997.

  22. Schmitt, M.M., Schiiler, E., Braun, M., Hating, D., and Schreier, P., Horseradish Peroxidase: An Effective but Unselective Biocatalyst for Biaryl Synthesis, Tetrahedron Lett., vol. 39, pp. 2945-2946, 1998.

  23. Seebach, D., Dahinden, R., Marti, R.E., Beck, A.K., Plattner, D.A., and Kuehnle, F.N.M., On the Ti TADDOLate-Catalyzed Diels-Alder Addition of 3-Butenoyl-1,3-Oxazolidin-2-One to Cyclopentadiene. General Features of Ti-BINOLate- and Ti-TADDOLate-Mediated Reactions, J. Org. Chem., vol. 60, pp. 1788-1799, 1995.

  24. Setnicka, M., Bulanek, R., Capek, L., and Cicmanec, P., N-Butane Oxidative Dehydrogenation over VOX-HMS Catalyst, J. Mol. Catal. A Chem., vol. 344, pp. 1-10, 2011.

  25. Sharma, V.B., Jain, S.L., and Sain, B., Copper (II) Schiff Base Catalysed Aerobic Oxidative Coupling of 2-Naphthols: An Efficient and Simple Synthesis of Binaphthols, J. Mol. Catal. A Chem., vol. 219, pp. 61-64, 2004.

  26. Sharma, V.B., Jain, S.L., and Sain, B., Methyltrioxorhenium-Catalyzed Aerobic Oxidative Coupling of 2-Naphthols to Binaphthols, Tetrahedron Lett., vol. 44, pp. 2655-2656, 2003.

  27. Shibasaki, M., Sasai, H., and Arai, T., Asymmetric Catalysis with Heterobimetallic Compounds, Angew. Chem. Int. Ed. Engl., vol. 36, pp. 1236-1256, 1997.

  28. Slink, W.E. and DeGroot, P.B., Vanadium-Titanium Oxide Catalysts for Oxidation of Butene to Acetic Acid, J. Catal., vol. 68, pp. 423-432, 1981.

  29. Somei, H., Asano, Y., Yoshida, T., Takizawa, S., Yamataka, H., and Sasai, H., Dual Activation in a Homolytic Coupling Reaction Promoted by an Enantioselective Dinuclear Vanadium (IV) Catalyst, Tetrahedron Lett., vol. 45, pp. 1841-1844, 2004.

  30. Tanev, P.T. and Pinnavaia, T.J., A Neutral Templating Route to Mesoporous Molecular Sieves, Science, vol. 267, pp. 865-867, 1995.

  31. Umare, P.S. and Tembe, G.L., Catalytic Oxidative Coupling of 2-Naphthol Using Metal B Diketonates, React. Kinet. Catal. Lett., vol. 82, pp. 173-178, 2004.

  32. Wallis, P.J., Booth, K.J., Patti, A.F., and Scott, J.L., Oxidative Coupling Revisited: Solvent-Free, Heterogeneous and in Water, Green Chem., vol. 8, pp. 333-337, 2006.

  33. Yadav, G.D. and Aduri, P., Aldol Condensation of Benzaldehyde with Heptanal to Jasminaldehyde over Novel Mg-Al Mixed Oxide on Hexagonal Mesoporous Silica, J. Mol. Catal. A Chem., vol. 355, pp. 142-154, 2012.

  34. Yadav, G.D. and Manyar, H.G., Synthesis of a Novel Redox Material UDCaT-3: An Efficient and Versatile Catalyst for Selective Oxidation, Hydroxylation and Hydrogenation Reactions, Adv. Synth. Catal., vol. 350, pp. 2286-2294, 2008.

  35. Yadav, G.D. and Mewada, R.K., Selectivity Engineering in the Synthesis of Value Added Chemicals: Oxidation of L-Octanol to L-Octanal over Nano-Fibrous Ag-OMS-2 Catalysts, Chem. Eng. Res. Des., vol. 90, pp. 86-97, 2012.

  36. Yadav, G.D. and Salunke, J.Y., Selectivity Engineering of Solid Base Catalyzed O-Methylation of 2-Naphthol with Dimethyl Carbonate to 2-Methoxynaphthalene, Catal. Today, vol. 207, pp. 180-190, 2013.

  37. Yadav, G.D. and Sharma, R.V., Biomass Derived Chemicals: Environmentally Benign Process for Oxidation of 5-Hydroxymethylfurfural to 2,5-Diformylfuran by Using Nano-Fibrous Ag-OMS-2-Catalyst, Appl. Catal. B Environ., vol. 147, pp. 293-301, 2014.

  38. Yadav, G.D., Subramanian, S., and Manyar, H.G., Selective Oxidation of Methyl Diphenyl Methyl Mercapto Acetate to Methyl Diphenyl Methyl Sulfinyl Acetate Using a Novel Catalyst UDCaT-3, Org. Process Res. Dev., vol. 14, pp. 537-543, 2010.

  39. Yadav, G.D. and Surve, P.S., Solventless Green Synthesis of 4-O-Aryloxy Carbonates from Aryl/Alkyl-Oxy Propanediols and Dimethyl Carbonate over Nano-Crystalline Alkali PromotedAlkaline EarthMetal Oxides, Catal. Sci. Technol., vol. 3, pp. 2668-2676, 2013.

  40. Yadav, G.D. and Yadav, A.R., Selective Liquid Phase Oxidation of Secondary Alcohols into Ketones by Tert-Butyl Hydroperoxide on Nano-Fibrous Ag-OMS-2 Catalyst, J. Mol. Catal. A Chem., vol. 380, pp. 70-77, 2013.


Articles with similar content:

SYNTHESIS OF 3-METHOXYCATECHOL FROM PYROGALLOL AND DIMETHYL CARBONATE IN LIQUID PHASE SLURRY REACTOR
Catalysis in Green Chemistry and Engineering, Vol.1, 2018, issue 1
Riitta Keiski, Ganapati D. Yadav, Pooja R. Tambe
GREEN SYNTHESIS OF 2,3-OXYBUTYL MALONONITRILE VIAMICHAEL REACTION OF METHYL VINYL KETONE WITH MALONONITRILE OVER TITANIA AND ZINC LOADED HYDROTALCITE CATALYSTS
Catalysis in Green Chemistry and Engineering, Vol.2, 2019, issue 1
Amarsinh L. Jadhav, Ganapati D. Yadav
PRODUCTION OF p-CYMENE BY ALKYLATION OF TOLUENE WITH PROPAN-2-OL
Catalysis in Green Chemistry and Engineering, Vol.2, 2019, issue 2
Mannepalli Lakshmi Kantam, Ajayan Vinu, Gunjan P. Deshmukh, Snehal R. Gajbhiye
HYDROGENOLYSIS OF GLYCEROL: COMPARISON OF CONTINUOUS AND BATCH MODE REACTIONS OVER Ni-ZnO CATALYSTS
Catalysis in Green Chemistry and Engineering, Vol.1, 2018, issue 1
Narsinga Raju, Nakka Lingaiah, Voggu Rekha, Miryala Balaraju
CO2 DISSOCIATION ON Ni-RICH MULTIMETAL CLUSTER: EFFECT OF Pt AND Mg
International Journal of Energy for a Clean Environment, Vol.19, 2018, issue 3-4
Zehao Huang, Zhe Xu, Lijuan Fu, Wenjie Qi, Ying Yang, Xu Chen, Jie Song