Zeolite Catalyzed Friedel-Crafts Reactions: A Review

Page: [491 - 506] Pages: 16

  • * (Excluding Mailing and Handling)

Abstract

Friedel-Crafts reaction is one of the most useful synthetic tools in organic chemistry, mainly in the synthesis of aromatic ketones. The active catalysts for this reaction are modified zeolites and are preferable catalysts when shape selectivity affects the formation of the expected product. In this review, our aim is to corroborate recent literature available on zeolite catalyzed Friedel-Crafts alkylation and acylation reaction.

Keywords: Synthetic zeolite, natural zeolite, Friedel-craft acylation, Friedel-craft alkylation, aromatic ketones, acylation reaction.

Graphical Abstract

[1]
Scott, J.; Guang, D.; Naeramitmarnsuk, K.; Thabuot, M.; Amal, R. J. Chem. Technol. Biotechnol., 2001, 77, 63-69.
[http://dx.doi.org/10.1002/jctb.521]
[2]
Weitkamp, J. Solid State Ion., 2000, 131, 175-188.
[http://dx.doi.org/10.1016/S0167-2738(00)00632-9]
[3]
Breck, D.W. John Wiley; New York, 1974.
[4]
Csicsery, S.M. American Chemical Society; Washington, D.C, 1976.
[5]
Jha, B.; Singh, D.N. Acta Geotech. Slov., 2012, 2, 63-71.
[6]
Auerbach, S.M.; Carrado, K.A.; Dutta, P.K. CRC Press; , 2003.
[7]
Jha, B.; Singh, D.N. J. Mater. Educ., 2011, 33, 65-132.
[8]
Venuto, P.B.; Landis, P.S. Adv. Catal., 1968, 18, 259-371.
[http://dx.doi.org/10.1016/S0360-0564(08)60430-7]
[9]
Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P.; Graille, J.; Pioch, D. J. Org. Chem., 1986, 51, 2128-2130.
[http://dx.doi.org/10.1021/jo00361a039]
[10]
Chiche, B.; Finieis, A.; Gauthier, C.; Geneste, P. Appl. Catal., 1987, 30, 365-369.
[http://dx.doi.org/10.1016/S0166-9834(00)84126-3]
[11]
Aucejo, A.; Burget, M.C.; Corma, A.; Fornes, V. Appl. Catal., 1986, 22, 187-200.
[http://dx.doi.org/10.1016/S0166-9834(00)82628-7]
[12]
Shabtai, J.; Lazar, R.; Biron, E. J. Mol. Catal., 1984, 27, 35-43.
[http://dx.doi.org/10.1016/0304-5102(84)85068-3]
[13]
Davis, M.E. Microporous Mesoporous Mater., 1998, 21, 173-182.
[http://dx.doi.org/10.1016/S1387-1811(98)00007-9]
[15]
Majchrzak, K.I.; Nowak, W. Thermochim. Acta, 2004, 413, 23-29.
[http://dx.doi.org/10.1016/j.tca.2003.10.021]
[16]
Somerset, V.S.; Petrik, L.F.; White, R.; Klinka, M.J.; Key, D.; Iwuoha, E.I. Fuel, 2005, 84, 2324-2329.
[http://dx.doi.org/10.1016/j.fuel.2005.05.012]
[17]
Wang, H.; Pinnavaia, J. Angew. Chem. Int. Ed., 2006, 45, 7603-7606.
[http://dx.doi.org/10.1002/anie.200602595]
[18]
Davis, M.E.; Lobo, R.F. J. Mater. Chem., 1992, 4, 756-768.
[http://dx.doi.org/10.1021/cm00022a005]
[19]
Beving, D.E.; O’Neill, C.R.; Yan, Y. Microporous Mesoporous Mater., 2008, 108, 77-85.
[http://dx.doi.org/10.1016/j.micromeso.2007.03.029]
[20]
Smart, M.; Willhalm, R.; Mori, S. Chemical Economics Handbook - SRI International/, Menlo Park, CA. 1995. https://ihsmarkit.com
[21]
Friedel, P.; Crafts, J.M. Compt. Rend, 1877, 84, 1392-1395.
[22]
Olah, G.A.; Krishnamurti, R.; Prakash, G.K.S. University of Southern California; , 1991, 3, pp. 293-339.
[23]
Sheldon, R.A.; Bekkum, H.V. Wiley-VCH; Weinheim, 2001.
[24]
Sartori, G.; Maggi, R. Chem. Rev., 2006, 106(3), 1077-1104.
[http://dx.doi.org/10.1021/cr040695c] [PMID: 16522017]
[25]
Olah, G.A. Wiley-Interscience., , 1963-1964.
[26]
Roberts, R.M.; Khalaf, A.A.; Dekker, M. Friedel-Crafts Alkylation Chemistry: A Century of Discovery; New York, 1984.
[27]
Olah, G.A. Wiley; New York, 1973.
[28]
Singh, A.P.; Bhattacharya, D.; Sharma, S. J. Mol. Catal. Chem., 1995, 102, 139-145.
[http://dx.doi.org/10.1016/1381-1169(95)00104-2]
[29]
Vinu, A.; Sawanat, D.P.; Ariga, K.; Hartmann, M.; Halligudi, S.B. Microporous Mesoporous Mater., 2005, 80, 195-203.
[http://dx.doi.org/10.1016/j.micromeso.2004.12.012]
[30]
Bokade, V.V.; Yadav, G.D. J. Nat. Gas Chem., 2007, 16, 186-192.
[http://dx.doi.org/10.1016/S1003-9953(07)60046-2]
[31]
Anand, C.; Srinivasu, P.; Alam, S.; Balasubramanian, V.V.; Sawant, D.P.; Palanichamy, M.; Murugesan, V.; Vinu, A. Microporous Mesoporous Mater., 2008, 111, 72-79.
[http://dx.doi.org/10.1016/j.micromeso.2007.07.011]
[32]
Devi, K.R.P.S.; Sreeja, P.B.; Sugunan, S. Int. Nano Lett., 2013, 3, 40-47.
[http://dx.doi.org/10.1186/2228-5326-3-40]
[33]
Li, J.; Xu, C.; Lou, L.L.; Zhang, C.; Yu, K.; Qi, B.; Liu, S.; Wang, Y. Catal. Commun., 2013, 38, 59-62.
[http://dx.doi.org/10.1016/j.catcom.2013.04.008]
[34]
Bejblová, M.; Procházková, D.; Cejka, J. ChemSusChem, 2009, 2(6), 486-499.
[http://dx.doi.org/10.1002/cssc.200900007] [PMID: 19350610]
[35]
Serrano, D.P.; Garcia, R.A.; Otero, D. Appl. Catal. A., 2009, 359, 69-78.
[http://dx.doi.org/10.1016/j.apcata.2009.02.013]
[36]
Grieken, R.V.; Sotelo, J.L.; Menendez, J.M.; Melero, J.A. Microporous Mesoporous Mater., 2000, 39, 135-147.
[http://dx.doi.org/10.1016/S1387-1811(00)00190-6]
[37]
Matsumoto, A.; Chen, H.; Tsutsumi, K.; Grun, M.; Unger, K. Microporous Mesoporous Mater., 1999, 32, 55-62.
[http://dx.doi.org/10.1016/S1387-1811(99)00089-X]
[38]
Garcia, R.A.; Serrano, D.P.; Vicente, G.; Otero, D.; Linares, M. Stud. Surf. Sci. Catal., 2008, 174, 1091-1094.
[http://dx.doi.org/10.1016/S0167-2991(08)80075-4]
[39]
Botella, P.; Corma, A.; Navarro, M.T.; Rey, F.; Sastre, G. J. Catal., 2003, 217, 406-417.
[http://dx.doi.org/10.1016/S0021-9517(03)00053-8]
[40]
Wei, H.; Liu, K.; Xie, S.; Xin, W.; Li, X.; Liu, S.; Xu, L. J. Catal., 2013, 307, 103-110.
[http://dx.doi.org/10.1016/j.jcat.2013.07.010]
[41]
Selvin, R.; Hsu, H.; Her, T. Catal. Commun., 2008, 10, 169-172.
[http://dx.doi.org/10.1016/j.catcom.2008.08.013]
[42]
Hsu, C.Y.; Chiang, A.S.T.; Selvin, R.; Thompson, R.W. J. Phys. Chem. B, 2005, 109(40), 18804-18814.
[http://dx.doi.org/10.1021/jp0526391] [PMID: 16853420]
[43]
Bond, G.; Gardner, J.A.; McCabe, R.W.; Shorrock, D.J. J. Mol. Catal. Chem., 2007, 278, 1-5.
[http://dx.doi.org/10.1016/j.molcata.2007.07.048]
[44]
Carvajal, R.; Chu, P.J.; Lunsford, J.H. J. Catal., 1990, 125, 123-131.
[http://dx.doi.org/10.1016/0021-9517(90)90083-V]
[45]
Aleixo, R.; Elvas-Leitao, R.; Martins, F.; Carvalho, A.P.; Brigasc, A.; Martins, A.; Nunes, N. Mol. Catal., 2017, 434, 175-183.
[http://dx.doi.org/10.1016/j.mcat.2017.03.007]
[46]
Guray, I.; Warzywoda, J.; Bac, N.; Sacco, A. Jr. Microporous Mesoporous Mater., 1999, 31, 241-251.
[http://dx.doi.org/10.1016/S1387-1811(99)00075-X]
[47]
Machado, V.; Rocha, J.; Carvalho, A.P.; Martins, A. Appl. Catal. A Gen., 2012, 445, 329-338.
[http://dx.doi.org/10.1016/j.apcata.2012.09.001]
[48]
Shih, P.C.; Wang, J.H.; Mou, C.Y. Catal. Today, 2004, 93-95, 365-370.
[http://dx.doi.org/10.1016/j.cattod.2004.06.025]
[49]
Guidotti, M.; Canaff, C.; Coustard, J.; Magnoux, P.; Guisnet, M. J. Catal., 2005, 230, 375-383.
[http://dx.doi.org/10.1016/j.jcat.2004.12.021]
[50]
Wine, G.; Pham-Huu, C.; Ledoux, M. Catal. Commun., 2006, 7, 768-772.
[http://dx.doi.org/10.1016/j.catcom.2006.03.002]
[51]
Winé, G.; Matta, J.; Tessonnier, J.P.; Pham-Huu, C.; Ledoux, M.J. Chem. Commun. (Camb.), 2003, 9(4), 530-531.
[PMID: 12638984]
[52]
Wine, G.; Vanhaecke, E.; Ivanova, S.; Ziessel, R.; Pham-Huu, C. Catal. Commun., 2009, 10, 477-480.
[http://dx.doi.org/10.1016/j.catcom.2008.10.014]
[53]
Ledoux, M.J.; Hantzer, S.; Pham-Huu, C.; Desaneaux, M.P.; Guille, J. J. Catal., 1988, 114, 176-185.
[http://dx.doi.org/10.1016/0021-9517(88)90019-X]
[54]
Ledoux, M.J.; Pham-Huu, C. CATTech, 2001, 5, 226-246.
[http://dx.doi.org/10.1023/A:1014092930183]
[55]
Basso, S.; Tessonnier, J.P.; Pham-Huu, C.; Ledoux, M.; Wine, G. US Patent 20030162649, 2003.
[56]
Kantarli, I.C.; Artok, L.; Bulut, H.; Yilmaz, S.; Ulku, S. Stud. Surf. Sci. Catal., 2002, 142, 799-806.
[http://dx.doi.org/10.1016/S0167-2991(02)80104-5]
[57]
Bai, G.; Li, T.; Yang, Y.; Zhang, H.; Lan, X.; Li, F.; Han, J.; Ma, Z.; Chen, Q.; Chen, G. Catal. Commun., 2012, 29, 114-117.
[http://dx.doi.org/10.1016/j.catcom.2012.09.028]
[58]
Bigi, F.; Carloni, S.; Flego, C.; Maggi, R.; Mazzacani, A.; Rastelli, M.; Sartori, G. J. Mol. Catal. Chem., 2002, 178, 139-146.
[http://dx.doi.org/10.1016/S1381-1169(01)00284-9]
[59]
Chen, Z.; Feng, Y.; Tong, T.; Zeng, A. Appl. Catal. A., 2014, 482, 92-98.
[http://dx.doi.org/10.1016/j.apcata.2014.05.028]
[60]
Matsukata, M.; Ogura, M.; Osaki, T.; Rao, P.R.H.P.; Nomura, M.; Kikuchi, E. Top. Catal., 1999, 9, 77-92.
[http://dx.doi.org/10.1023/A:1019106421183]
[61]
Chen, Z.; Chen, W.; Tong, T.; Zeng, A. J. Mol. Catal. Chem., 2015, 396, 231-238.
[http://dx.doi.org/10.1016/j.molcata.2014.09.038]
[62]
Klisakova, J.; Cerveny, L.; Cejka, J. Appl. Catal., 2004, 272, 79-86.
[http://dx.doi.org/10.1016/j.apcata.2004.05.019]
[63]
Aiello, R.; Giordano, G.; Testa, F. In, 1st ed; Studies in Surface Science and Catalysis, 2002, Vol. 142, p. 23.
[64]
Kosova, G.; Cejka, J. Collect. Czech. Chem. Commun., 2002, 67, 1760-1778.
[http://dx.doi.org/10.1135/cccc20021760]
[65]
Corma, A.; Nemeth, L.T.; Renz, M.; Valencia, S. Nature, 2001, 412(6845), 423-425.
[http://dx.doi.org/10.1038/35086546] [PMID: 11473313]
[66]
Prochazkova, D.; Kurfirtova, L.; Pavlatova, J. Catal. Today, 2012, 179, 78-84.
[http://dx.doi.org/10.1016/j.cattod.2011.06.033]
[67]
Ammar, M.; Jiang, S.; Ji, S. J. Solid State Chem., 2016, 233, 303-310.
[http://dx.doi.org/10.1016/j.jssc.2015.11.014]
[68]
Yamazaki, T.; Makihara, M.; Komura, K. J. Mol. Catal. Chem., 2017, 426, 170-176.
[http://dx.doi.org/10.1016/j.molcata.2016.11.012]
[69]
Koehle, M.; Zhang, Z.; Goulas, K.A.; Caratzoulas, S.; Vlachos, D.G.; Lobo, R.F. Appl. Catal. A., 2018, 564, 90-101.
[http://dx.doi.org/10.1016/j.apcata.2018.06.005]
[70]
Makihara, M.; Aoki, H.; Komura, K. Catal. Lett., 2018, 148, 2974-2979.
[http://dx.doi.org/10.1007/s10562-018-2530-1]
[71]
Chevella, D.; Mameda, N.; Kodumuri, S.; Banothu, R.; Gajula, K.S.; Kutepov, B.I.; Namaa, N. Catal. Commun., 2018, 105, 20-25.
[http://dx.doi.org/10.1016/j.catcom.2017.11.002]
[72]
Sun, Y.; Prins, R. Appl. Catal. A., 2008, 336, 11-16.
[http://dx.doi.org/10.1016/j.apcata.2007.08.015]
[73]
Choi, M.; Cho, H.S.; Srivastava, R.; Venkatesan, C.; Choi, D.H.; Ryoo, R. Nat. Mater., 2006, 5(9), 718-723.
[http://dx.doi.org/10.1038/nmat1705] [PMID: 16892049]
[74]
Kim, J.; Cho, K.; Ryoo, R. Appl. Catal. A., 2014, 470, 420-426.
[http://dx.doi.org/10.1016/j.apcata.2013.11.019]
[75]
Kim, W.; Kim, J.C.; Kim, J.; Seo, Y.; Ryoo, R. ACS Catal., 2013, 3, 192-195.
[http://dx.doi.org/10.1021/cs300678n]
[76]
Kim, J.; Kim, W.; Seo, Y.; Kim, J.C.; Ryoo, R. J. Catal., 2013, 301, 187-197.
[http://dx.doi.org/10.1016/j.jcat.2013.02.015]
[77]
Bai, G.; Ma, Z.; Shi, L.; Lan, X.; Wang, Y.; Han, J.; Qiu, M.; Fu, H.; Liu, P. Appl. Catal. A., 2012, 427-428, 114-118.
[http://dx.doi.org/10.1016/j.apcata.2012.03.040]
[78]
Bidart, A.M.F.; Borges, A.P.S.; Nogueira, L.; Lachter, E.R.; Mota, C.J.A. Catal. Lett., 2001, 75, 155-157.
[http://dx.doi.org/10.1023/A:1016748206714]
[79]
Wang, Y.; Song, H.; Sun, X. Chin. J. Catal., 2016, 37, 2134-2141.
[http://dx.doi.org/10.1016/S1872-2067(16)62587-1]
[80]
Liu, K.F.; Xie, S.J.; Liu, S.; Xu, G.; Gao, N.; Xu, L. J. Catal., 2011, 283, 68-74.
[http://dx.doi.org/10.1016/j.jcat.2011.07.004]
[81]
Zhang, K.; Zhang, H.; Xu, G.; Xiang, S.; Xu, D.; Liu, S.; Li, H. Appl. Catal. A., 2001, 207, 183-190.
[http://dx.doi.org/10.1016/S0926-860X(00)00663-3]
[82]
Nur, H.; Ramli, Z.; Efendi, J.; Rahman, A.N.A.; Chandren, S.; Yuan, L.S. Catal. Commun., 2011, 12, 822-825.
[http://dx.doi.org/10.1016/j.catcom.2011.01.015]
[83]
Choudhary, V.R.; Jana, S.K.; Patil, N.S.; Bhargava, S.K. Microporous Mesoporous Mater., 2003, 57, 21-35.
[http://dx.doi.org/10.1016/S1387-1811(02)00529-2]