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Collect. Czech. Chem. Commun. 1992, 57, 862-868
https://doi.org/10.1135/cccc19920862

The Shape-Selective Acylation of 2-Methoxynaphthalene, Catalyzed by Zeolites Y, Beta and ZSM-12

Gillian Harvey and Georg Mäder

Technisch-Chemisches Laboratorium, ETH-Zentrum, Universitatsstr. 6, 8092 Zurich, Switzerland

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  • Li Xuemin, Martinez Abraham, Kuperman Alexander, Han Jinyi, Katz Alexander: Supramolecular approaches for pore expansion in mesoporous Y zeolites. Microporous and Mesoporous Materials 2024, 373, 113100. <https://doi.org/10.1016/j.micromeso.2024.113100>
  • Nikseresht Ahmad, Mirzaei Nasim, Masoumi Sara, Azizi Hamid Reza: Response Surface Methodology Optimization of Friedel–Crafts Acylation Using Phosphotungstic Acid Encapsulation in a Flexible Nanoporous Material. ACS Mater. Au 2023, 3, 123. <https://doi.org/10.1021/acsmaterialsau.2c00062>
  • Feng Gang, Wen Zhi-Hui, Wang Jiancheng, Lu Zhang-Hui, Zhou Jian, Zhang Rongbin: Guiding the design of practical MTW zeolite catalysts: An integrated experimental-theoretical perspective. Microporous and Mesoporous Materials 2021, 312, 110810. <https://doi.org/10.1016/j.micromeso.2020.110810>
  • Azhagapillai Prabhu, Sundaravel Balachandran, Pachamuthu Muthusamy P.: Acylation of isobutylbenzene with acetic anhydride on AlKIT-6 mesoporous acid catalyst. Materials Science for Energy Technologies 2021, 4, 128. <https://doi.org/10.1016/j.mset.2021.02.002>
  • Turkustani Aisha M., Aldahiri Reema H.: Highly Efficient Nanocrytalline Zeolite Catalyst for the Hydroxyalkylation of Anisole with Benzaldehyde. sci adv mater 2021, 13, 1070. <https://doi.org/10.1166/sam.2021.4005>
  • Guo Y., Sun J., Guo F., He Yu., Chen P.: Friedel-Crafts acylation of 2-methoxynaphthalene with acetic anhydride catalyzed by phosphotungstic acid in ionic liquid. BCC 2019, 51, 289. <https://doi.org/10.34049/bcc.51.2.4449>
  • Jain Zenish J., Gide Paraag S., Kankate Rani S.: Biphenyls and their derivatives as synthetically and pharmacologically important aromatic structural moieties. Arabian Journal of Chemistry 2017, 10, S2051. <https://doi.org/10.1016/j.arabjc.2013.07.035>
  • Zhang Bin, Zhang Yahong, Hu Yuanyuan, Shi Zhangping, Azhati Arepati, Xie Songhai, He Heyong, Tang Yi: Microexplosion under Microwave Irradiation: A Facile Approach to Create Mesopores in Zeolites. Chem. Mater. 2016, 28, 2757. <https://doi.org/10.1021/acs.chemmater.6b00503>
  • Serrano D. P., Escola J. M., Sanz R., Garcia R. A., Peral A., Moreno I., Linares M.: Hierarchical ZSM-5 zeolite with uniform mesopores and improved catalytic properties. New J. Chem. 2016, 40, 4206. <https://doi.org/10.1039/C5NJ02856F>
  • Chen Ping, Wang Wei, Zhai Yuchun: Friedel–Crafts acylation of 2-methoxynaphthalene with acetic anhydride over Al-HMS. J Porous Mater 2014, 21, 441. <https://doi.org/10.1007/s10934-014-9790-y>
  • Ouyang Xiaoying, Hwang Son-Jong, Runnebaum Ron C., Xie Dan, Wanglee Ying-Jen, Rea Thomas, Zones Stacey I., Katz Alexander: Single-Step Delamination of a MWW Borosilicate Layered Zeolite Precursor under Mild Conditions without Surfactant and Sonication. J. Am. Chem. Soc. 2014, 136, 1449. <https://doi.org/10.1021/ja410141u>
  • Sreedhar I., Kantamneni Harini, Suresh Kumar Reddy K., Raghavan K. V.: Optimal process conditions for zeolite catalyzed acylation of anisole. Kinet Catal 2014, 55, 229. <https://doi.org/10.1134/S0023158414020116>
  • Lu Juyou, Zhang Hao, Chen Xiaowu, Liu Hongxia, Jiang Yuyang, Fu Hua: Palladium‐Catalyzed Synthesis of Aromatic Ketones and Isoindolobenzimidazoles via Selective Aromatic CH Bond Acylation. Adv Synth Catal 2013, 355, 529. <https://doi.org/10.1002/adsc.201200743>
  • Chen Min, Pan Aixia, He Tong, Xu Lulu, Fang Yu, Li Huaming, Xie Jimin: Efficient Synthesis of 1-Acetylpyrene Using [Bmim]Cl–FeCl3 Ionic Liquid as Dual Catalyst and Solvent. International Journal of Chemical Reactor Engineering 2013, 11, 1. <https://doi.org/10.1515/ijcre-2012-0021>
  • Hsu Hsiu Ling, Selvin Rosilda, Roselin L. Selva: Preparation of Core-Shell Silica - 12-Tungstophosphoricacid Nanoparticles for Acylation of Aromatics. AMR 2013, 706-708, 219. <https://doi.org/10.4028/www.scientific.net/AMR.706-708.219>
  • Méndez Leticia, Torviso Rosario, Pizzio Luis, Blanco Mirta: 2-Methoxynaphthalene acylation using aluminum or copper salts of tungstophosphoric and tungstosilicic acids as catalysts. Catal Today 2011, 173, 32. <https://doi.org/10.1016/j.cattod.2011.03.028>
  • Sartori Giovanni, Maggi Raimondo: Update 1 of: Use of Solid Catalysts in Friedel−Crafts Acylation Reactions. Chem. Rev. 2011, 111, PR181. <https://doi.org/10.1021/cr100375z>
  • Pande Manoj A., Samant Shriniwas D.: Acylation of Aromatic Ethers Using Different Carboxylic Acid Anhydrides as Acylating Agents in the Presence of Nontoxic, Noncorrosive Resin Amberlyst 15 as a Solid Acid Catalyst. Synthetic Communications 2011, 41, 754. <https://doi.org/10.1080/00397911003644407>
  • Sharghi Hashem, Jokar Mahboubeh, Doroodmand Mohammad Mahdi, Khalifeh Reza: Catalytic Friedel–Crafts Acylation and Benzoylation of Aromatic Compounds Using Activated Hematite as a Novel Heterogeneous Catalyst. Adv Synth Catal 2010, 352, 3031. <https://doi.org/10.1002/adsc.201000319>
  • Revathi S., Preethi M. Esther Leena, Siddarth S., Sivakumar T.: Solvent free selective acetylation of veratrole over 12-tungstophosporic acid immobilized mesoporous silicates. Catalysis Communications 2008, 9, 594. <https://doi.org/10.1016/j.catcom.2007.03.027>
  • Waghmare Nilesh G., Kasinathan Palraj, Amrute Amol, Lucas Nishita, Halligudi S.B.: Titania supported silicotungstic acid: An efficient solid acid catalyst for veratrole acylation. Catalysis Communications 2008, 9, 2026. <https://doi.org/10.1016/j.catcom.2008.03.043>
  • Vinu Ajayan, Justus Josena, Anand C., Sawant Dhanashri P., Ariga Katsuhiko, Mori Toshiyuki, Srinivasu Pavuluri, Balasubramanian Veerappan V., Velmathi Sivan, Alam Sher: Hexagonally ordered mesoporous highly acidic AlSBA-15 with different morphology: An efficient catalyst for acetylation of aromatics. Microp Mesop Mat 2008, 116, 108. <https://doi.org/10.1016/j.micromeso.2008.03.033>
  • Yuan Bing, Li Zongshi, Liu Yongjun, Zhang Shusheng: Liquid phase acylation of 2-methylnaphthalene catalyzed by H-beta zeolite. Journal of Molecular Catalysis A 2008, 280, 210. <https://doi.org/10.1016/j.molcata.2007.11.004>
  • Karthik G., Kulangiappar K., Marken Frank, Kulandainathan M. Anbu: Electrochemically promoted Friedel–Crafts acylation of aromatic compounds. Tetrahetron Lett 2008, 49, 2625. <https://doi.org/10.1016/j.tetlet.2008.02.084>
  • Bejblová Martina, Zones Stacey I., Čejka Jiří: Highly selective synthesis of acetylferrocene by acylation of ferrocene over zeolites. CATAL A GENERAL 2007, 327, 255. <https://doi.org/10.1016/j.apcata.2007.05.023>
  • Bejblová Martina, Klisáková-Mayerová Jana, Červený Libor, Čejka Jiří: One-pot synthesis of isobutyl toluene via combined acylation and hydrogenation over Pd–Beta zeolite. Microp Mesop Mat 2006, 90, 384. <https://doi.org/10.1016/j.micromeso.2005.11.005>
  • Shanmugapriya K., Palanichamy M., Balasubramanian V.V., Murugesan V.: Vapour phase reaction of m-cresol and ethyl acetate over MCM-41 molecular sieves: One-pot synthesis of coumarin derivatives. Microp Mesop Mat 2006, 95, 272. <https://doi.org/10.1016/j.micromeso.2006.05.020>
  • Bordoloi Ankur, Mathew Nevin T., Devassy Biju M., Mirajkar S.P., Halligudi S.B.: Liquid-phase veratrole acylation and toluene alkylation over WOx/ZrO2 solid acid catalysts. Journal of Molecular Catalysis A 2006, 247, 58. <https://doi.org/10.1016/j.molcata.2005.11.029>
  • Sudha S., Palanichamy M., Balasubramanian V.V., Arabindoo Banumathi, Murugesan V.: The vapour phase reaction of tert-butylbenzene and tert-butyl acetate over Al-MCM-41 molecular sieves. Journal of Molecular Catalysis A 2006, 255, 220. <https://doi.org/10.1016/j.molcata.2006.03.050>
  • Sartori Giovanni, Maggi Raimondo: Use of Solid Catalysts in Friedel−Crafts Acylation Reactions. Chem. Rev. 2006, 106, 1077. <https://doi.org/10.1021/cr040695c>
  • Deutsch J., Prescott H.A., Müller D., Kemnitz E., Lieske H.: Acylation of naphthalenes and anthracene on sulfated zirconia. Journal of Catalysis 2005, 231, 269. <https://doi.org/10.1016/j.jcat.2005.01.024>
  • Kantam Mannepalli Lakshmi, Ranganath Kalluri Venkata Sri, Sateesh Mutyala, Kumar Kota Balaji Shiva, Choudary Boyapati Manoranjan: Friedel–Crafts acylation of aromatics and heteroaromatics by beta zeolite. Journal of Molecular Catalysis A 2005, 225, 15. <https://doi.org/10.1016/j.molcata.2004.08.018>
  • Klisáková Jana, Červený Libor, Čejka Jiřı́: On the role of zeolite structure and acidity in toluene acylation with isobutyric acid derivatives. CATAL A GENERAL 2004, 272, 79. <https://doi.org/10.1016/j.apcata.2004.05.019>
  • Udayakumar S, Pandurangan A, Sinha P.K: Vapour phase reaction of ethylbenzene with isopropyl acetate over mesoporous Al-MCM-41 molecular sieves. Journal of Molecular Catalysis A 2004, 216, 121. <https://doi.org/10.1016/j.molcata.2004.02.014>
  • Botella P., Corma A., Navarro M.T., Rey F., Sastre G.: On the shape selective acylation of 2-methoxynaphthalene over polymorph C of Beta (ITQ-17). Journal of Catalysis 2003, 217, 406. <https://doi.org/10.1016/S0021-9517(03)00053-8>
  • Beers Annemarie E.W, Nijhuis T.A, Aalders N, Kapteijn F, Moulijn J.A: BEA coating of structured supports—performance in acylation. Applied Catalysis A: General 2003, 243, 237. <https://doi.org/10.1016/S0926-860X(02)00547-1>
  • Bezouhanova Cvetana P.: Synthesis of aromatic ketones in the presence of zeolite catalysts. CATAL A GENERAL 2002, 229, 127. <https://doi.org/10.1016/S0926-860X(02)00021-2>
  • Guignard C, Pédron V, Richard F, Jacquot R, Spagnol M, Coustard J.M, Pérot G: Acylation of veratrole by acetic anhydride over Hβ and HY zeolites. CATAL A GENERAL 2002, 234, 79. <https://doi.org/10.1016/S0926-860X(02)00199-0>
  • Botella P, Corma A, Sastre G: Al-ITQ-7, a Shape-Selective Zeolite for Acylation of 2-Methoxynaphthalene. Journal of Catalysis 2001, 197, 81. <https://doi.org/10.1006/jcat.2000.3057>
  • Rebrov E.V., Seijger G.B.F., Calis H.P.A., de Croon M.H.J.M., van den Bleek C.M., Schouten J.C.: The preparation of highly ordered single layer ZSM-5 coating on prefabricated stainless steel microchannels. CATAL A GENERAL 2001, 206, 125. <https://doi.org/10.1016/S0926-860X(00)00594-9>
  • Escola J.M, Davis M.E: Acylation of biphenyl with acetic anhydride and carboxylic acids over zeolite catalysts. CATAL A GENERAL 2001, 214, 111. <https://doi.org/10.1016/S0926-860X(01)00473-2>
  • Beers A.E.W., Nijhuis T.A., Kapteijn F., Moulijn J.A.: Zeolite coated structures for the acylation of aromatics. Microp Mesop Mat 2001, 48, 279. <https://doi.org/10.1016/S1387-1811(01)00368-7>
  • Fromentin E., Coustard J.-M., Guisnet M.: Mechanism of 1-Acetyl-2-methoxynaphthalene Isomerisation over a HBEA Zeolite. Journal of Catalysis 2000, 190, 433. <https://doi.org/10.1006/jcat.1999.2762>
  • Andy P., Garcia-Martinez J., Lee G., Gonzalez H., Jones C.W., Davis M.E.: Acylation of 2-Methoxynaphthalene and Isobutylbenzene over Zeolite Beta. Journal of Catalysis 2000, 192, 215. <https://doi.org/10.1006/jcat.2000.2855>
  • Botella P., Corma A., López-Nieto J.M., Valencia S., Jacquot R.: Acylation of Toluene with Acetic Anhydride over Beta Zeolites: Influence of Reaction Conditions and Physicochemical Properties of the Catalyst. Journal of Catalysis 2000, 195, 161. <https://doi.org/10.1006/jcat.2000.2971>
  • Das Debasish, Cheng Soofin: Friedel–Crafts acylation of 2-methoxynaphthalene over zeolite catalysts. CATAL A GENERAL 2000, 201, 159. <https://doi.org/10.1016/S0926-860X(00)00438-5>
  • Casagrande Manuela, Storaro Loretta, Lenarda Maurizio, Ganzerla Renzo: Highly selective Friedel–Crafts acylation of 2-methoxynaphthlene catalyzed by H-BEA zeolite. CATAL A GENERAL 2000, 201, 263. <https://doi.org/10.1016/S0926-860X(00)00448-8>
  • Fromentin E., Coustard J.-M., Guisnet M.: Acetylation of 2-methoxynaphthalene with acetic anhydride over a HBEA zeolite. Journal of Molecular Catalysis A 2000, 159, 377. <https://doi.org/10.1016/S1381-1169(00)00225-9>
  • Kim Sung Duk, Lee Kyung Hee, Lee Jae Sung, Kim Young Gul, Yoon Kwang Eui: The regioselective acylation of 2-methoxynaphthalene to 2-acetyl-6-methoxynaphthalene over zeolite beta. Journal of Molecular Catalysis A 2000, 152, 33. <https://doi.org/10.1016/S1381-1169(99)00266-6>
  • Moreau Patrice, Finiels Annie, Meric Pascal: Acetylation of dimethoxybenzenes with acetic anhydride in the presence of acidic zeolites. Journal of Molecular Catalysis A 2000, 154, 185. <https://doi.org/10.1016/S1381-1169(99)00373-8>
  • Kawada Atsushi, Mitamura Shuichi, Matsuo Jun-ichi, Tsuchiya Takehiro, Kobayashi Shu: Friedel-Crafts Reactions Catalyzed by Rare Earth Metal Trifluoromethanesulfonates. Bulletin of the Chemical Society of Japan 2000, 73, 2325. <https://doi.org/10.1246/bcsj.73.2325>
  • Heinichen H.K., Hölderich W.F.: Acylation of 2-Methoxynaphthalene in the Presence of Modified Zeolite HBEA. Journal of Catalysis 1999, 185, 408. <https://doi.org/10.1006/jcat.1999.2526>
  • Bharathi Patibandla, Waghmode Suresh B, Sivasanker Subramanian, Vetrivel Rajappan: Molecular Modeling Studies on Zeolite Catalysts for Shape-Selective Electrophilic Substitution: I Acylation of 2-Methoxynaphthalene. Bulletin of the Chemical Society of Japan 1999, 72, 2161. <https://doi.org/10.1246/bcsj.72.2161>
  • Davis M.E.: Zeolite-based catalysts for chemicals synthesis. Microp Mesop Mat 1998, 21, 173. <https://doi.org/10.1016/S1387-1811(98)00007-9>
  • Ruiz Jaime, Astruc Didier, Gilbert Laurent: CoCl2 catalyzed trifluoroacetylation versus dimerization of methoxyaromatics using trifluoroacetic anhydride. Tetrahetron Lett 1996, 37, 4511. <https://doi.org/10.1016/0040-4039(96)00870-2>
  • Gunnewegh Eric A., Gopie Saritha S., van Bekkum Herman: MCM-41 type molecular sieves as catalysts for the Friedel-Crafts acylation of 2-methoxynaphthalene. Journal of Molecular Catalysis A 1996, 106, 151. <https://doi.org/10.1016/1381-1169(95)00270-7>
  • Amouzegh Patricia, Finiels Annie, Geneste Patrick, Ginestar Erick, Moreau Patrice: Acylation of a substituted benzofuran over an HY zeolite and its subsequent deacylation and reacylation. Catal Lett 1995, 34, 389. <https://doi.org/10.1007/BF00806889>