Abstract
Various V/P mole ratios of vanadium substituted Keggin-type phosphomolybdic acids were synthesized by the hydrothermal method. These materials were characterized using several physico-chemical techniques such as X-ray diffraction, FT-IR, N2-sorption, Raman spectroscopy, 31P MAS NMR, SEM and NH3-TPD. FT-IR, Raman spectroscopy and 31P NMR results confirm the formation of the primary structure of the Keggin ion and its crystalline nature is shown clearly by XRD. NH3-TPD results reveal that the acidity of the materials systematically decreases with increasing vanadium content. The Knoevenagel reaction carried out over vanadium substituted phosphomolybdic acid with various V/P mole ratios indicate that the higher V/P mole ratio exhibits better catalytic performance under solvent free conditions. The catalytic properties correlate with the structural properties and the acidity of the materials.
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References
Trost BM (1991) Comprehensive organic synthesis. Elsevier, Oxford, p 133
Knoevenagel L (1898) Ber 31:258
Enders D, Muller S, Demir AS (1988) Tetrahedron Lett 29:6437
Reeves RL, Patai S (1996) The chemistry of carbonyl compounds. Interscience Publishers, New York 567
Jones G (1967) Org React 15:204
Attanasi O, Fillippone P, Mei A (1983) Syn Commun 13:1203
Shanthan Rao P, Venkatratnam RV (1991) Tetrahedron Lett 32:5821
Bao W, Zhang Y, Wang J (1996) Syn Commun 26:3025
Saravanamurugan S (2006) Appl Catal A Gen 298:8
Boullet FT, Focucad A (1982) Tetrahedron Lett 23:4927
Macquarrie DJ, Clark JH, Lambert A, Gmode JE, Priest A (1997) React Funct Polym 35:153
Brunel D (1993) Micropor Mesopor Mater 27:329
Hein RW, Astle MJ, Shelton JR (1961) J Org Chem 26:4874
Moison H, Boullet FT, Focaud A (1987) Tetrahedron 43:537
Bigi F, Chesini L, Maggi R, Sartori G (1999) J Org Chem 64:1033
Kantam ML, Choudary BM, Reddy CV, Rao KK, Figueras F (1998) Chem Commun 1033
Joshi UD, Joshi PN, Tamhankar SS, Joshi VV, Rode CV, Shiralkar VP (2003) Appl Catal A Gen 239:209
Climent MJ, Corma A, Forens V, Frau A, Lopez RG, Iborra S, Primo J (1996) J Catal 163:392
Corma A, Fornes V, Aranda RMM, Garcia H, Primo J (1990) Appl Catal 59:237
Corma A, Aranda RMM, Sanchez F, Guinst M, Barrault J, Bouchoule C, Duprez D, Maurel R, Montassier C (1991) Stud Surf Sci Catal 62:503
Corma A, Aranda RMM (1993) Appl Catal A 105:271
Oskooie HA, Heravi MM, Derikvand F, Khorasani M (2006) Syn Commu 36:2819
Bhunia S, Saha D, Koner S (2011) Langmuir 27:15322
Metzger JO (1998) Ang Chem Inter Ed 37:2975
Tanaka K, Toda F (2000) Chem Rev 100:1025
Pillai MK, Singh S, Jonnalagadda SB (2011) Kinet Catal 52:536
Fumin Z, Maiping G, Hanqing G, Jun W (2007) Front Chem Eng China 1:296
Sen R, Bera R, Ashis B, Gutlich P, Ghosh S, Mukherjee AK, Koner S (2008) Langmuir 24:5970
Ilkenhans T, Herzag B, Braun T, Schlogl R (1995) J Catal 153:275
Zhang J, Tang Y, Li G, Hu C (2005) Appl Catal A Gen 278:251
Predoeva A, Damyanova S, Gaigneaux EM, Petrov L (2007) Appl Catal A Gen 319:14
Raj NKK, Deshpande SS, Ingle RH, Raja T, Manikandan P (2004) Catal Lett 24:1001
Yue ZY, Bao B, Liu RL, Xi HS, Yong H (2006) Chin J Chem 24:1001
Tang Y, Zhang J (2006) J Serb Chem Soc 71:111
Ogiwara Y, Takahashi K, Kitazawa T, Sakai N (2015) J Org Chem 80:3101
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B Viswanadham thanks to the University of KwaZulu-Natal for the award of the AES Postdoctoral Research Fellowship.
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Viswanadham, B., Jhansi, P., Chary, K.V.R. et al. Efficient Solvent Free Knoevenagel Condensation Over Vanadium Containing Heteropolyacid Catalysts. Catal Lett 146, 364–372 (2016). https://doi.org/10.1007/s10562-015-1646-9
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DOI: https://doi.org/10.1007/s10562-015-1646-9