Synthesis of 5-Benzoylacenaphthene in the Presence of [Bmim] Cl/AlCl3 Ionic Liquid

Shu Yun Zhu; De Li Jiang; Yu Fang; Ji Min Xie; Min Chen

doi:10.4028/www.scientific.net/AMR.443-444.830

Paper Titles

Finite Element Analysis on Fracture Problem of Rubber - Metal Ring
p.809

Application of Optimized GM (1,1) in the Machine Tool Thermal Error Modeling
p.813

Equivalent Profile of High-Speed Mill Considering Gyroscopic Effect
p.818

Analytical Modeling of the Spindle Shaft of Heavy Load Deflection Angle Milling Head Dynamics Using Timoshenko Beam Model
p.823

Synthesis of 5-Benzoylacenaphthene in the Presence of [Bmim] Cl/AlCl₃ Ionic Liquid
p.830

Experimental Investigation of Vibration and Noise Control of Reciprocating Compressors
p.837

Cam Grinding Interpolation Research Based on Cubic Non-Uniform Rational B-Splines
p.843

Mg(OH)₂ Partially Substituted Alkaline Peroxide Mechanical Pulping of Poplar
p.850

Application Research of APDL on Contrarotating Propeller Parametric Modeling
p.855

HomeAdvanced Materials ResearchAdvanced Materials Research Vols. 443-444Synthesis of 5-Benzoylacenaphthene in the Presence...

Synthesis of 5-Benzoylacenaphthene in the Presence of [Bmim] Cl/AlCl₃ Ionic Liquid

Abstract:

Acylation of acenaphthene with benzoyl chloride to 5-benzoylacenaphthene catalyzed by [Bmin]Cl/AlCl₃ ([Bmin]⁺ = 1-butyl-3-methylimidazolium cation) ionic liquid was investigated. Pure 5-benzoylacenaphthene was obtained and the structure of 5-benzoylacenaphthene was identified by GC/MS, FT-IR and ¹H NMR spectra. The yield of 5-benzoylacenaphthene was up to 85.2 % and the selectivity towards 5-benzoylacenaphthene was up to 89.6 %. The [Bmim]C1/A1C1₃ ionic liquid catalyst shows well catalytic activity after running for 5 times. The facile product separation and the recycling performance of the ionic liquid catalyst is expected to contribute to the development of clean and environmentally friendly strategy for the synthesis of 5-benzoylacenaphthene.

You might also be interested in these eBooks

Manufacturing Science and Materials Engineering

View Preview

Info:

Periodical:

Advanced Materials Research (Volumes 443-444)

Pages:

830-836

DOI:

https://doi.org/10.4028/www.scientific.net/AMR.443-444.830

Citation:

Cite this paper

Online since:

January 2012

Authors:

Shu Yun Zhu, De Li Jiang, Yu Fang, Ji Min Xie, Min Chen

Keywords:

5-Benzoylacenaphthene, Acenaphthene, Acylation, Benzoyl Chloride, Ionic Liquid (IL)

Export:

RIS, BibTeX

Price:

Permissions:

Request Permissions

References

[1] U. Freese, F. Heinrich, and F. Roessner, Acylation of aromatic compounds on h-beta zeolites, Catal. Today, vol. 49, Feb. 1999, p.237–244, doi: 10. 1016/S0920-5861(98)00429-5.

DOI: 10.1016/s0920-5861(98)00429-5

Google Scholar

[2] J. Howarth, P. James, and J.F. Dai, The coupling of aryl halides in the ionic liquid [bmim]PF6, Tetrahedron Lett., vol. 41, Dec. 2000, p.10319–10321, doi: 10. 1016/S0040-4039(00)01854-2.

DOI: 10.1016/s0040-4039(00)01854-2

Google Scholar

[3] X. Xie., J. Lu, B. Chen, J. Han, X. She, and X. Pan, Pd/C-catalyzed Heck reaction in ionic liquid accelerated by microwave heating, Tetrahedron Lett., vol. 45, Jan. 2004, pp.809-811, doi: 10. 1016/j. tetlet. 2003. 11. 042.

DOI: 10.1016/j.tetlet.2003.11.042

Google Scholar

[4] J.A. Boon, J.A. Levisky, J.L. Pflug, and J.S. Wilkers, Friedel–Crafts reactions in ambient temperature molten salts, J. Org. Chem., vol. 51, Feb. 1986, p.480–483, doi: 10. 1021/jo00354a013.

DOI: 10.1021/jo00354a013

Google Scholar

[5] C. Hardacre, S.P. Katdare, D. Milroy, P. Nancarrow, D.W. Rooney, and J.M. Thompson, A catalytic and mechanistic study of the Friedel–Crafts benzoylation of anisole using zeolites in ionic liquids, J. Catal., vol: 227, Oct. 2004, pp.44-52.

DOI: 10.1016/j.jcat.2004.05.034

Google Scholar

[6] C.J. Adams, M.J. Earle, G. Robberts, and K.R. Seddon, Friedel–Crafts reactions in room temperature ionic liquids, Chem. Commum, vol. 19, Jul. 1998, p.2097–(2098).

DOI: 10.1039/a805599h

Google Scholar

[7] X. Yuan, M. Chen, Q. Dai, and X. Cheng, Friedel–Crafts acylation of anthracene with oxalyl chloride catalyzed by ionic liquid of [bmim]Cl/AlCl3, Chem. Eng. J. vol. 146, Feb. 2009, p.266–269, doi: 10. 1016/j. cej. 2008. 09. 022.

DOI: 10.1016/j.cej.2008.09.022

Google Scholar

[8] J.J. Eisch and K.C. Fichter, Organometallic compounds of Group III. 40. Kinetic control and locoselectivity in the electrophilic cleavage of allylic aluminum compounds: reactions of acenaphthenylaluminum reagents with carbonyl substrates, J. Org. Chem., vol. 49, Nov. 1984, pp.4631-4639.

DOI: 10.1021/jo00198a011

Google Scholar

[9] K.R. Seddon, Ionic liquids for clean technology, J. Chem. Tech. Biotechnol, vol. 68, Apr. 1997, pp.351-356, doi: 10. 1002/(SICI)1097-4660(199704)68: 4<351: AIDJCTB613>3. 0. CO; 2-4.

DOI: 10.1002/(sici)1097-4660(199704)68:4<351::aid-jctb613>3.0.co;2-4

Google Scholar

[10] A. Stark, B.L. MacLean, and R.D. Singer, 1-Ethyl-3-methylimidazolium halogenoaluminate ionic liquids as solvents for Friedel–Crafts acylation reactions of ferrocene, J. Chem. Soc., Dalton Trans. 1999, p.63–66. doi: 10. 1039/A806708B.

DOI: 10.1039/a806708b

Google Scholar

[11] P. Wasserscheid and W. Keim, Ionic liquids—new "solutions" for transition metal catalysis, Angew. Chem., Int. Ed., vol. 39, Oct. 2000, p.3772–3789, doi: 1002/1521-3773(20001103).

DOI: 10.1002/1521-3773(20001103)39:21<3772::aid-anie3772>3.0.co;2-5

Google Scholar