Advertisement

Bronsted acid-functionalized choline chloride-butane sultone for the catalytic decomposition of cumene hydroperoxide to phenol

  • M P Padma priya
  • G R Rajarajeswari
Regular Article

Abstract

Choline chloride and 1,4-butane sultone were combined to obtain a sulphonic acid-functionalized ionic liquid. The structural properties of the ionic liquid were evaluated with AT-IR, NMR, mass and elemental analysis. The Bronsted acidity of the ionic liquid was confirmed from the AT-IR analysis of pyridine-adsorbed samples. The catalytic activity of the ionic liquid was studied for the preparation of phenol from cumene hydroperoxide by Hock process. Various reaction parameters were optimized and kinetics of the reaction was evaluated. This Bronsted acidic choline chloride-butane sultone-based ionic liquid was highly selective towards the conversion of cumene hydroperoxide to phenol. Ease of use and recovery, low environmental impact, and effective reduction of activation energy make it a potential candidate for industrial production of phenol.

Graphical Abstract

Synthesis of a Bronsted acid ionic liquid based on choline chloride and 1,4-butane sultone was described. This ionic liquid was selective in the conversion of cumene hydroperoxide to phenol. Simple synthetic procedure, immiscibility with reaction mixture, recyclability are the added advantages of this ionic liquid.

Keywords

Choline chloride 1,4 butane sultone ionic liquid phenol hock process 

Notes

Acknowledgements

The authors thank the Department of Science and Technology and University Grants Commission, Government of India for DST-FIST and UGC-SAP-sponsored analytical instrumentation facilities at the Department of Chemistry, Anna University, Chennai. MPPP is thankful to Anna University, Chennai for providing financial aid through Anna Centenary Research Fellowship.

Supplementary material

12039_2018_1445_MOESM1_ESM.pdf (608 kb)
Supplementary material 1 (pdf 607 KB)

References

  1. 1.
    Wu C Y, Pretzer W R and Kobylinski T P 1979 Decomposition of cumene hydroperoxide with a heterogeneous catalyst U.S. Patent No. 4, 173, 587Google Scholar
  2. 2.
    Knifton J F 1989 Method for production of phenol/acetone from cumene hydroperoxide U.S. Patent No. 4, 870, 217Google Scholar
  3. 3.
    Knifton J F and Sanderson J R 1990 Method for production of phenol/acetone from cumene hydroperoxide U.S. Patent No. 4, 898, 995Google Scholar
  4. 4.
    Kumar K P, Selvin R, Kumari P, Roselin L S, Arul N S and Bououdina M 2010 Selective decomposition of cumene hydroperoxide into phenol and acetone over nanocrystalline ZSM-5 Int. J. Mater. Eng. Innov. 1 417CrossRefGoogle Scholar
  5. 5.
    Knifton J F and Grice N J 1989 Method for production of phenol/acetone from cumene hydroperoxide U.S. Patent No. 4, 876, 397Google Scholar
  6. 6.
    Barton D H R and Delanghe N C 1997 New Catalysts for the conversion of cumene hydroperoxide into phenol Tetrahedron Lett. 38 6351CrossRefGoogle Scholar
  7. 7.
    Yadav G D and Asthana N S 2003 Selective decomposition of cumene hydroperoxide into phenol and acetone by a novel cesium substituted heteropolyacid on clay Appl. Catal. A 244 341CrossRefGoogle Scholar
  8. 8.
    Sasidharan M and Kumar R 1997 Zeolite-catalysed selective decomposition of cumene Hydroperoxide into phenol and acetone J. Chem. Res. 52 Google Scholar
  9. 9.
    Selvin R, Rajarajeswari G R, Roselin L S, Sadasivam V, Sivasankar B and Rengaraj K 2001 Catalytic decomposition of cumene hydroperoxide into phenol and acetone Appl. Catal. A 219 125CrossRefGoogle Scholar
  10. 10.
    Amarasekara A S 2016 Acidic ionic liquids Chem. Rev. 116 6133CrossRefGoogle Scholar
  11. 11.
    Zhang Q, Zhang S and Deng Y 2011 Recent advances in ionic liquid catalysis Green Chem. 13 2619CrossRefGoogle Scholar
  12. 12.
    Ratti R 2014 Ionic liquids: synthesis and applications in catalysis Adv. Chem. 1 Google Scholar
  13. 13.
    Rengstl D, Fischer V and Kunz W 2014 Low-melting mixtures based on choline ionic liquids PCCP 16 22815CrossRefGoogle Scholar
  14. 14.
    Harjani J R, Nara S J and Salunkhe M M 2002 Lewis acidic ionic liquids for the synthesis of electrophilic alkenes via the Knoevenagel condensation Tetrahedron Lett. 43 1127CrossRefGoogle Scholar
  15. 15.
    Haerens K, Matthijs E, Chmielarz A and Bruggen B V 2009 The use of ionic liquids based on choline chloride for metal deposition: A green alternative? J. Environ. Manag. 90 3245CrossRefGoogle Scholar
  16. 16.
    Morales R C, Tambyrajah V, Jenkins P R, Davies D L and Abbott A P 2004 The regiospecific Fischer indole reaction in choline chloride\(\cdot 2\text{ZnCl}_{2}\) with product isolation by direct sublimation from the ionic liquid Chem. Commun. 158 Google Scholar
  17. 17.
    Harishkumar H N, Mahadevan K M, Kiran Kumar H C and Satyanarayan N D 2011 A facile, choline chloride/urea catalyzed solid phase synthesis of coumarins via Knoevenagel condensation Org. Commun. 4 26Google Scholar
  18. 18.
    Florea A, Petica A, Anicai L and Visan T 2010 Preliminary studies of silver coatings formation from choline chloride based ionic liquids UPB Sci. Bull. 72 115Google Scholar
  19. 19.
    Paape N, Wei W, Bosmann A, Kolbeck C, Maier F, Steinruck H P, Wasserscheid P and Schulz P S 2008 Chloroalkylsulfonate ionic liquids by ring opening of sultones with organic chloride salts Chem. Commun. 3867 Google Scholar
  20. 20.
    An H, Kang L, Gao W, Zhao X and Wang Y 2013 Synthesis and characterization of novel Brønsted-Lewis acidic ionic liquids Green Sustain. Chem. 3 32CrossRefGoogle Scholar
  21. 21.
    Seubold F H and Vaughan W E 1953 Acid-catalyzed decomposition of cumene hydroperoxide J. Am. Chem Soc. 75 3790CrossRefGoogle Scholar

Copyright information

© Indian Academy of Sciences 2018

Authors and Affiliations

  1. 1.Department of Chemistry, College of Engineering, GuindyAnna UniversityChennaiIndia

Personalised recommendations