Skip to main content
SpringerLink
Log in

Preparation of 3,6-dibenzoylacenapthene in the presence of Lewis acidic ionic liquids

  • Published:
Reaction Kinetics and Catalysis Letters Aims and scope Submit manuscript

Abstract

The reactivity of Lewis acidic ionic liquids for the acylation of acenaphthene to 3,6-dibenzoylacenaphthene was investigated. Ionic liquids of different alkyl chain length and metal chloride were synthesized and tested for the reaction to discuss the effects of Lewis acidity of the ionic liquid on the alkylation. Pure 3,6-dibenzoylacenaphthene was obtained and the structure of 3,6-dibenzoylacenaphthene was identified by GC/MS, FT-IR and 1H NMR spectra. [Emim]C1/A1C13 ionic liquid was found to be the most active catalyst in the acylation. The yield of 3,6-dibenzoylacenaphthene was up to 89.6% and the selectivity towards 3,6-dibenzoylacenaphthene was up to 92.2%. The experiment shows that [Emim]Cl/AlCl3 can be used as both catalyst and solvent, it is reusable and environmentally friendly for the preparation of 3,6-dibenzoylacenaphthene.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Singh RP, Kamble RM, Chandra KL (2001) Tetrahedron 57:241

    Article  CAS  Google Scholar 

  2. Lund T, Lundgren B, Lund H (1995) Acta Chem Scand 49:755

    Article  CAS  Google Scholar 

  3. Xie XG, Lu JP, Chen B (2004) Tetrahedron Lett 45:809

    Article  CAS  Google Scholar 

  4. Baleizao C, Pires N, Gigante B (2004) Tetrahedron Lett 45:4375

    Article  CAS  Google Scholar 

  5. Boon JA, Levisky JA, Pflug JL (1986) J Org Chem 51:480

    Article  CAS  Google Scholar 

  6. Hardacre C, Katdare SP, Milroy D (2004) J Catal 227:44

    Article  CAS  Google Scholar 

  7. Adams CJ, Earle MJ, Seddon KR (1998) Chem Commun 19:2097

    Google Scholar 

  8. Huddleston JG, Visser AE, Reichert WM, Willauer HD, Broker GA, Rogers RD (2001) Green Chem 3:156

    Article  CAS  Google Scholar 

  9. Welton T (1999) Chem Rev 99:2071

    Article  CAS  Google Scholar 

  10. Nara SJ, Harjani JR, Salunkhe MM (2001) J Org Chem 66:8616

    Article  CAS  Google Scholar 

  11. Vogel P (1985) Carbocation chemistry. Elsevier, Amsterdam, p 444

  12. Reichardt C (1988) Federal Republic of Germany. VCH, Weinheim, p 248

  13. Xin HL, Wu Q, Han MH, Wang DZ, Jin Y (2005) Appl Catal A: Gen 292:354

    Article  CAS  Google Scholar 

  14. Howarth J, Hanlon K, Fayne D, McCormac P (1997) Tetrahedron Lett 38:3097

    Article  CAS  Google Scholar 

  15. Yoo K, Namboodiri VV, Varma RS, Smirniotis PG (2004) J Catal 222:511

    Article  CAS  Google Scholar 

  16. Matsumoto T, Ichikawa K (1984) J Am Chem Soc 106:4316

    Article  CAS  Google Scholar 

Download references

Acknowledgment

This work was supported in part by the National Natural Science Foundation of China (No. 20207003).

Author information

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang, 212013, Jiangsu, People’s Republic of China

    Min Chen, Lijing Huang, Ying Luo, Minqiang He & Jimin Xie

  2. School of Material Science and Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang, 212013, Jiangsu, People’s Republic of China

    Xinhua Yuan

Authors
  1. Min Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lijing Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ying Luo
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Minqiang He
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jimin Xie
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Xinhua Yuan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Min Chen.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chen, M., Huang, L., Luo, Y. et al. Preparation of 3,6-dibenzoylacenapthene in the presence of Lewis acidic ionic liquids. React Kinet Catal Lett 98, 355–363 (2009). https://doi.org/10.1007/s11144-009-0088-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11144-009-0088-z

Keywords

Search

Navigation