Direct alkenylation of aromatics with phenylacetylene over supported H3PW12O40 catalysts as a clean and highly efficient approach to producing α-arylstyrenes

作者: Zhongkui Zhao , Yitao Dai , Ting Bao , Renzhi Li , Guiru Wang

DOI: 10.1016/J.JCAT.2011.12.024

关键词:

摘要: Abstract Phosphotungstic acid (PTA) catalysts supported on MCM-41 prepared via a wet impregnation method assisted by vacuum with heating (IMPVH) were first employed for direct alkenylation of different aromatics phenylacetylene to synthesize α-arylstyrenes. N 2 adsorption–desorption, FT-IR, X-ray diffraction (XRD), and NH 3 temperature-programmed desorption (NH TPD) characterization techniques used reveal the relationship between catalyst’s nature properties. The results demonstrate that fabricated 25 wt.% PTA/MCM-41 catalyst exhibits outstanding catalytic performance, remarkably better than HY zeolite. It is also found properties are strongly dependent PTA dispersity, sites, preservability Keggin structure, mesopore architecture, notably affected loading calcination temperature. stability illustrate more 99% maximum conversion can be obtained, 92% maintained up 540 min time stream. We find decrease in activity, along long reaction time, mainly ascribable deactivation coke deposition. spent refreshed, 97.1% obtained over regenerated catalyst. This approach highly efficient extra-substituted benzene, polycyclic aromatics, even heteroaromatics, suggesting presented this paper green synthesis protocol

参考文章(55)
Tongqiang Wang, Yuanyuan Hu, Songlin Zhang, A novel and efficient method for the olefination of carbonyl compounds with Grignard reagents in the presence of diethyl phosphite Organic and Biomolecular Chemistry. ,vol. 8, pp. 2312- 2315 ,(2010) , 10.1039/C001931C
Ruoshi Li, Sunewang R. Wang, Wenjun Lu, FeCl3-Catalyzed Alkenylation of Simple Arenes with Aryl-Substituted Alkynes Organic Letters. ,vol. 9, pp. 2219- 2222 ,(2007) , 10.1021/OL070737U
Zhongkui Zhao, Weihong Qiao, Xiuna Wang, Guiru Wang, Zongshi Li, Lübo Cheng, HY zeolite promoted free-solvent alkylation of α-methylnaphthalene with long chain olefins in liquid-solid intermittent reaction Journal of Molecular Catalysis A-chemical. ,vol. 241, pp. 194- 198 ,(2005) , 10.1016/J.MOLCATA.2005.07.022
Gauthier Winé, Zora El Berrichi, Cuong Pham-Huu, BETA zeolite supported on silicon carbide for Friedel-Crafts fixed-bed reactions Journal of Molecular Catalysis A-chemical. ,vol. 278, pp. 64- 71 ,(2007) , 10.1016/J.MOLCATA.2007.08.018
Q.-H. Xia, S.-C. Shen, J. Song, S. Kawi, K. Hidajat, Structure, morphology, and catalytic activity of β zeolite synthesized in a fluoride medium for asymmetric hydrogenation Journal of Catalysis. ,vol. 219, pp. 74- 84 ,(2003) , 10.1016/S0021-9517(03)00154-4
Ezzat Rafiee, Mohammad Joshaghani, Sara Eavani, Solmaz Rashidzadeh, A revision for the synthesis of β-enaminones in solvent free conditions: efficacy of different supported heteropoly acids as active and reusable catalysts Green Chemistry. ,vol. 10, pp. 982- 989 ,(2008) , 10.1039/B803249A
Joseph A Kocal, Bipin V Vora, Tamotsu Imai, Production of linear alkylbenzenes Applied Catalysis A-general. ,vol. 221, pp. 295- 301 ,(2001) , 10.1016/S0926-860X(01)00808-0
J. S. Beck, J. C. Vartuli, W. J. Roth, M. E. Leonowicz, C. T. Kresge, K. D. Schmitt, C. T. W. Chu, D. H. Olson, E. W. Sheppard, S. B. McCullen, J. B. Higgins, J. L. Schlenker, A new family of mesoporous molecular sieves prepared with liquid crystal templates Journal of the American Chemical Society. ,vol. 114, pp. 10834- 10843 ,(1992) , 10.1021/JA00053A020
Yoshimi Yamamoto, Shigeru Hatanaka, Katsuyuki Tsuji, Kazuyuki Tsuneyama, Ryuichiro Ohnishi, Hiroyuki Imai, Yuichi Kamiya, Toshio Okuhara, Direct addition of acetic acid to ethylene to form ethyl acetate in the presence of H4SiW12O40/SiO2 Applied Catalysis A-general. ,vol. 344, pp. 55- 60 ,(2008) , 10.1016/J.APCATA.2008.03.040
Wataru Ninomiya, Masahiro Sadakane, Shinji Matsuoka, Hiroki Nakamura, Hiroyuki Naitou, Wataru Ueda, An efficient synthesis of α-acyloxyacrylate esters as candidate monomers for bio-based polymers by heteropolyacid-catalyzed acylation of pyruvate esters Green Chemistry. ,vol. 11, pp. 1666- 1674 ,(2009) , 10.1039/B914515J