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International Journal of Chemical Reactor Engineering

Ed. by de Lasa, Hugo / Xu, Charles Chunbao

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1542-6580
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Efficient Synthesis of 1-Acetylpyrene Using [Bmim]Cl–FeCl3 Ionic Liquid as Dual Catalyst and Solvent

Min Chen / Aixia Pan / Tong He / Lulu Xu / Yu Fang / Huaming Li / Jimin Xie
Published Online: 2013-06-18 | DOI: https://doi.org/10.1515/ijcre-2012-0021

Abstract

Friedel–Crafts acylation of pyrene with acetic anhydride to 1-acetylpyrene catalyzed by three metal chloride and three Lewis acidic ionic liquids (ILs) containing 1-butyl-3-methylimidazolium chloride ([Bmim]Cl) and different metal chloride was investigated. ILs were prepared and tested for the acylation to explore the effects of Lewis acidity of ILs on the synthesis of 1-acetylpyrene. [Bmim]Cl–FeCl3 was found to be the most suitable catalyst, and the possible pathway for the acylation of pyrene with acetic anhydride catalyzed by [Bmim]Cl–FeCl3-IL was discussed. Pure 1-acetylpyrene was obtained and its structure was identified by gas chromatography–mass spectrometer, Fourier transform infrared and 1H NMR spectra.

Keywords: Lewis acidic ionic liquids; Friedel–Crafts acylation; 1-acetylpyrene; acetic anhydride; catalysis

References

  • 1.

    Harrington PJ, Lodewijk E. Twenty years of Naproxen technology. Org Process Res Dev 1997;1:72–6.Google Scholar

  • 2.

    Harvey G, Mäder G. The shape-selective acylation of 2-methoxynaphthalene, catalyzed by zeolites Y, beta and ZSM-12. Collect Czech Chem Commun 1992;57:862–8.Google Scholar

  • 3.

    Fujisawa T, Kondo K, Sakai K. Process for preparing thiophene derivatives. US Patent, 4 266 067, 1981.Google Scholar

  • 4.

    Kantam ML, Ranganath KVS, Sateesh M, Kumar KBS, Choudary BM. Friedel-Crafts acylation of aromatics and heteroaromatics by beta zeolite. J Mol Catal A: Chem 2005;225:15–20.Google Scholar

  • 5.

    Das D, Cheng S. Friedel-Crafts acylation of 2-methoxynaphthalene over zeolite catalysts. Appl Catal A: Gen 2000;201:159–68.Google Scholar

  • 6.

    Kaur J, Griffin K, Harrison B, Kozhevnikov IV. Friedel-Crafts acylation catalysed by heteropoly acids. J Catal 2002;208:448–55.Google Scholar

  • 7.

    Kozhevnikov IV. Friedel-Crafts acylation and related reactions catalysed by heteropoly acids. Appl Catal A: Gen 2003;256: 3–18.Google Scholar

  • 8.

    Firouzabadi H, Iranpoor N, Nowrouzi F. Aluminum dodecatungstophosphate (AlPW12O40) as a non-hygroscopic Lewis acid catalyst for the efficient Friedel–Crafts acylation of aromatic compounds under solvent-less conditions. Tetrahedron 2004;60:10843–50.Google Scholar

  • 9.

    Deutsch J, Trunschke A, Müller D, Quaschning V, Kemnitz E, Lieske H. Acetylation and benzoylation of various aromatics on sulfated zirconia. J Mol Catal A: Chem 2004;207:51–7.Google Scholar

  • 10.

    Zane F, Melada S, Signoretto M, Pinna F. Active and recyclable sulphated zirconia catalysts for the acylation of aromatic compounds. Appl Catal A: Gen 2006;299:137–44.Google Scholar

  • 11.

    Deutsch J, Prescott HA, Müller D, Kemnitz E, Lieske H. Acylation of naphthalenes and anthracene on sulfated zirconia. J Catal 2005;231:269–78.Google Scholar

  • 12.

    Chen M, Li D, Luo Y, He MQ, Xie JM, Li HM, Yuan XH. Synthesis of 5-benzoylacenaphthene in the presence of Lewis acidic ionic liquids. J Ind Eng Chem 2011;17:14–7.Google Scholar

  • 13.

    Chen M, Huang LJ, Luo Y, He MQ, Xie JM, Yuan XH. Preparation of 3,6-dibenzoylacenapthene in the presence of Lewis acidic ionic liquids. React Kinet Catal Lett 2009;98:355–63.Web of ScienceGoogle Scholar

  • 14.

    Xin HL, Wu Q, Han MH, Wang DZh, Jin Y. Alkylation of benzene with 1-dodecene in ionic liquids [Rmim]+Al2Cl6X (R=butyl, octyl and dodecyl; X=chlorine, bromine and iodine). Appl Catal A: Gen 2005;292:354–361.Google Scholar

  • 15.

    Kim DS, Ahn WS. Diphenylmethane synthesis using ionic liquids as Lewis acid catalyst. Korean J Chem Eng 2003;20:39–43.Google Scholar

  • 16.

    Nara SJ, Harjani JR, Salunkhe MM. Friedel-Crafts Sulfonylation in 1-Butyl-3-methylimidazolium chloroaluminate ionic liquids. J Org Chem 2001;66:8616–20.Google Scholar

  • 17.

    Joglekar HG, Rahman I, Kulkarni BD. The path ahead for ionic liquids. Chem Eng Technol 2007;30:819–828.Web of ScienceGoogle Scholar

  • 18.

    Sarsani VR, Lyon CJ, Hutchenson KW, Harmer MA, Subrarnaniam B. Continuous acylation of anisole by acetic anhydride in mesoporous solid acid catalysts: reaction media effects on catalyst deactivation. J Catal 2007;245:184–90.Web of ScienceGoogle Scholar

  • 19.

    Boon JA, Levisky JA, Pflug JL, Wilkes JS. Friedel–Crafts reactions in ambient-temperature molten salts. J Org Chem 1986;51:480–3.Google Scholar

  • 20.

    Li ChZh, Liu WJ, (Kent) Zhao ZB. Efficient synthesis of benzophenone derivatives in Lewis acid ionic liquids. Catal Commun 2007;8:1834–7.Google Scholar

  • 21.

    Hardacre C, Nancarrow P, Rooney DW, Thompson JM. Friedel–Crafts benzoylation of anisole in ionic liquids: catalysis, separation, and recycle studies. Org Process Res Develop 2008;12:1156–63.CrossrefWeb of ScienceGoogle Scholar

  • 22.

    Earle MJ, Hakala U, Hardacre C, Karkkainen J, McAuley BJ, Rooney DW, Seddon KR, Thompson JM, Wähäla K. Chloroindate(III) ionic liquids: recyclable media for Friedel–Crafts acylation reactions. Chem Commun 2005;7:903–5.CrossrefGoogle Scholar

  • 23.

    Adams CJ, Earle MJ, Roberts G, Seddon KR. Friedel-Crafts reactions in room temperature ionic liquids. Chem Commun 1998;19:2097–8.Google Scholar

  • 24.

    Yin DH, Li ChZh, Tao L, Yu NY, Hu S, Yin DL. Synthesis of diphenylmethane derivatives in Lewis acidic ionic liquids. J Mol Catal A: Chem 2006;245:260–5.Google Scholar

  • 25.

    Luo Y, Pan AX, Xing M, Chen M, Xie JM. Synthesis of 1-acetylpyrene via Friedel–Crafts reaction using chloroaluminate ionic liquids as dual catalyst and solvent. Adv Mater Res 2012;560–1:214–20.Google Scholar

  • 26.

    Zhang J, Huang ChP, Chen BH, Li JW, Li YX. Alkylation of isobutane and butene using chloroaluminate imidazolium ionic liquid as catalyst: effect of organosulfur compound additive. Korean J Chem Eng 2008;25:982–6.CrossrefWeb of ScienceGoogle Scholar

  • 27.

    Davey PN, Newman CP, Seddon KR, Earle MJ. Improvements in Friedel–Crafts reactions. World Patent, 9919288, 1999.Google Scholar

About the article

Published Online: 2013-06-18


Citation Information: International Journal of Chemical Reactor Engineering, ISSN (Online) 1542-6580, ISSN (Print) 2194-5748, DOI: https://doi.org/10.1515/ijcre-2012-0021.

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