Catalytic performances of cross-linking humic acids supported Pd/Ni bimetallic catalyst for heck reaction

Xu, Qijie; Zhang, Lei; Shi, Wenzhong; Cui, Yuanchen

doi:10.2478/v10026-009-0031-0

Abstract

The cross-linking humic acids (CL-HAs), epichlorohydrin as the cross-linking reagent and the supported Pd/Ni bimetallic catalysts (CL-HAs-Pd/Ni) were prepared and characterized by IR, AAS, XPS, TEM. The effects of reaction time, temperature, base, solvent and the amount of catalyst on the properties of the catalyst were studied. These catalysts could catalyze the Heck reaction of aryl halides and substituted aryl halides with acrylic acids or styrene successfully; the yields were all above 95%.

References

Biffis, A., Zecca, M. & Basato, M. (2001). Palladium metal catalysts in Heck C-C coupling reactions. J mol Catal A Chem, 173(1-2): 249-274.DOI:10.1016/S1381-1169(01)00153-4.10.1016/S1381-1169(01)00153-4
Search in Google Scholar
Deiters, A. & Stephen, F. M. (2004). Synthesis of Oxygen- and Nitrogen-Containing Heterocycles by Ring-Closing Metathesis. Chem. Rev., 104 (5):2199-2238.10.1021/cr0200872.
Search in Google Scholar
Irina, P. & Andrei, V. (2000). The Heck Reaction as a Sharpening Stone of Palladium Catalysis. Chem Rev, 100(8): 3009-3066.DOI:10.1021/cr9903048.10.1021/cr9903048
Search in Google Scholar
Liu, P., Wang, L. & Li, L. M. et al. (2004). Study on the Heck Arylation Reaction Catalyzed by Chitosan-Immobilized Palladium(0) Complex. Chin J Orgc Chem, 24(1): 59-65. DOI: CNKI:SUN:YJHU.0.2004-01-010.
Search in Google Scholar
Liu, D. G., Lee, J. F. & Tang, M. T. (2005). Characterization of Pt-Ru/C catalysts by X-ray absorption spectroscopy and temperature-programmed surface reaction. J Mol Catal A Chem, 231(1-2): 197-206. DOI: 10.1016/j.molcata.2005.07.011.10.1016/j.molcata.2005.07.011
Search in Google Scholar
Zhang, H. F., Zhang, L. & Cui, Y. Ch. (2007). Synthesis of chitosan microsphere-resin supported palladium complex and its catalytic properties for Mizoroki-Heck reaction. React. Funct. Polym., 67(4): 322-328. DOI: 10.1016/j.reactfunctpolym.2007.01.004.10.1016/j.reactfunctpolym.2007.01.004
Search in Google Scholar
Zhang, L. & Cui, Y C. (2005). Synthesis of Starch Supported Palladium Catalyst and Its Catalytic Properties for Heck Reaction. Chin J Appl CHem, 22(4): 440-445. DOI: CNKI:SUN:YYHX.0.2005-04-00J.
Search in Google Scholar
Sun, Q., Zhang, Zh. Q. & Su, Y. Ch. et al. (1994). The Best Catalytic Condition of Multi-Nuclear Pd(?)-Ni(?) Phthalocyanine for Heck Reaction Selected with Orthogonal Test. J. Northeast Normal University, 2(2): 53-56. DOI: CNKI:SUN:DBSZ.0.1994-02-013.
Search in Google Scholar
Reddy, R. K., Kumar, N. S. & Surendra, P. R. et al. (2006). Cellulose supported palladium(0) catalyst for Heck and Sonogashira coupling reactions. J Mol. Catal. A. Chem., 252(1-2): 12-16. DOI: 10.1016/j.molcata. 2006.02.024.
Search in Google Scholar
Klavins, M. J. & Dipane, K. B. (2001). Influence of colloid suspensions of humic acids upon the alkaline fading of carbocations. Chemosphere, 21(7-8): 555-560. DOI: 10.1002/poc.1317.10.1002/poc.1317
Search in Google Scholar
Klavins, M. J. & Babre, K. (2002). Decarboxylation and alkaline colour fading reactions in presence of humic substances. Chemosphere, 49(6): 685-689. DOI: 10.1016/S0045-6535(02)00303-X.10.1016/S0045-6535(02)00303-X
Search in Google Scholar
Bellamy, L. J., The infrared spectra of complex molecules[M]. Chapman and Hall, London, 1975.10.1007/978-94-011-6017-9
Search in Google Scholar
Stevenson, F. J. Humus chemistry: genesis, composition, reactions [M]. Wiley-interscience, New York, 1994.
Search in Google Scholar
Fan, K. N. An introduction of spectroscopy[M]. Higher education press, Bei Jing, 2001.
Search in Google Scholar
Fujita, S., Yoshida, T. & Bhanage, B. M. et al. (2002). Heck reaction with a silica-supported Pd-TPPTS liquid phase catalyst: effects of reaction conditions and various amines on the reaction rate. J Mol Catal A Chem, 188(1-2): 37-43. DOI: 10.1016/S1381-1169(02)00336-9.10.1016/S1381-1169(02)00336-9
Search in Google Scholar
Iweta, P. R., Anna, M. T. & Jozef, J. Z. (2006). Basefree efficient palladium catalyst of Heck reaction in molten tetrabutylammonium bromide. J Mol Catal A Chem, 257, 3-8. DOI: 10.1016/j.molcata.2006.03.064.10.1016/j.molcata.2006.03.064
Search in Google Scholar
Li, R. X. Green solvent (the synthesis and application of ion liquid) [M]. Chemical industry press, 2004.
Search in Google Scholar
Zhang, L. & Cui, Y. C. (2005). Synthesis of Polyvinyl Chloride-triethylene-tetramine Supported Pal- ladium Complex and Its Catalytic Properties for Heck Reaction. Acta Chimica Sinica, 10: 924-930. DOI: CNKI:SUN:HXXB.0.2005-10-009.
Search in Google Scholar
Jiang, J. Z. & Cai, C. (2006). In situ formation of dispersed palladium nanoparticles in microemulsion: Efficient reaction system for ligand-free Heck reaction. J Collid Interf Sci, 2006, 299(2): 938-943. DOI: 10.1016/j.jcis.2006.02.035.10.1016/j.jcis.2006.02.03516631192
Search in Google Scholar
Perez, R., Veronese, D. & Coelho, F. (2006). Palladium catalyzed Heck reaction of arenediazonium tetrafluoroborate salts with Baylis-Hillman adducts: production of α-benzyl-β-keto esters. Tetrahedron Lett, 47(8): 1325-1328. DOI: 10.1016/j.tetlet.2005.12.058.10.1016/j.tetlet.2005.12.058
Search in Google Scholar
Chen, F. X., Kelvin, T. & Shen, Sh. C. et al. (2007). Porous magnesia as solid base for ligand-free Heck reaction. Catal Commun, 8(3): 405-409. DOI: 10.1016/j.catcom.2006.06.032.10.1016/j.catcom.2006.06.032
Search in Google Scholar
Cai, M. Zh., Xu, Q. H. & Jiang, J. W. (2006). The first MCM-41-supported thioether palladium(0) complex: A highly active and stereoselective catalyst for Heck arylation of olefins with aryl halides. J Mol Catal A Chem, 260(1-2): 190-196. DOI: 10.1016/j.molcata.2006.07.014.10.1016/j.molcata.2006.07.014
Search in Google Scholar
Sun, Q., Yao, X. H., Su, Y. Ch. et al. (1994). Catalytic Study on Heck Reaction by Multi-nuclear Pd(?) Ni(?)(1:1) Phthalocyanine. J Synthetic Chem, 2(3), 282-286. DOI: CNKI:SUN:HCHX.0.1994-03-015.
Search in Google Scholar
Reetz, M. T., Breinbauer, R., Wanninger, K. (1996). Suzuki and Heck reactions catalyzed by preformed palladium clusters and palladium/nickel bimetallic clusters. Tetrahedron Lett, 37(26): 4499-4502. DOI: 10.1016/0040-4039(96)00924-0.10.1016/0040-4039(96)00924-0
Search in Google Scholar

Catalytic performances of cross-linking humic acids supported Pd/Ni bimetallic catalyst for heck reaction

Abstract

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