Kinetics of phenol alkylation with tert-butyl alcohol using sulfonic acid functional ionic liquid catalysts

Chemical Engineering Journal

Volumn 166, Issue 1, 2011, Pages 340-347

  Elavarasan, Pandian ^a   Kondamudi, Kishore ^a   Upadhyayula, Sreedevi ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY DELHI   (India)

Author keywords

Alkylation; Ionic liquid; Kinetics; N (4 sulfonic acid) butyl triethylammonium hydrogen sulfate; Phenol; Tert Butyl alcohol

Indexed keywords

4-TERT-BUTYLPHENOL; ACIDIC IONIC LIQUIDS; ARRHENIUS EQUATION; BUTYLPHENOL; CATALYTIC ACTIVITY; FUNCTIONAL IONIC LIQUIDS; KINETIC MODELS; MOLE RATIO; NEGATIVE ACTIVATION ENERGY; PHENOL ALKYLATION; PHENOL CONVERSION; PRODUCT DISTRIBUTIONS; REACTION MECHANISM; REACTION TEMPERATURE; REACTION TIME; SULFONIC ACID; SULFONIC ACID-FUNCTIONALIZED; TEMPERATURE RANGE; TERT-BUTYL ALCOHOLS; TERT-BUTYLATION OF PHENOL; TRIETHYLAMINES;

ACTIVATION ENERGY; ALCOHOLS; ALKYLATION; BATCH REACTORS; BUTANE; CATALYST ACTIVITY; HYDROGEN; IONS; PHENOLS; REACTION KINETICS;

IONIC LIQUIDS;

INSECTIVORA;

EID: 78650308561     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2010.11.001     Document Type: Article

References (27)

1. Shinde A.B., Shrigadi N.S., Samant S.D. tert-Butylation of phenols using tert-butyl alcohol in the presence of FeCl3-modified montmorillonite K10. Appl. Catal. A: Gen. 2004, 276:5-8.
2. Dumitriu E., Hulea V. Effects of channel structures and acid properties of large-pore zeolites in the liquid-phase tert-butylation of phenol. J. Catal. 2003, 218:249-257.
3. Sakthivel A., Dapurkar S.E., Gupta N.M., Kulshreshtha S.K., Selvam P. The influence of aluminium sources on the acidic behaviour as well as on the catalytic activity of mesoporous H-AlMCM-41 molecular sieves. Microporous Mesoporous Mater. 2003, 65:177-187.
4. Ojha K., Pradhan N.C., Samanta A.C. Kinetics of batch alkylation of phenol with tert-butyl alcohol over a catalyst synthesized from coal fly ash. J. Chem. Eng. 2005, 112:109-115.
5. Chandler K., Liotta C.L., Eckert C.A., Schiraldi D. Tuning alkylation reactions with temperature in near-critical water. AIChE J. 1998, 44:2080-2087.
6. Gui J., Ban H., Cong X., Zhang X., Hu Z., Sun Z. Selective alkylation of phenol with tert-butyl alcohol catalyzed by Brönsted acidic imidazolium salts. J. Mol. Catal. A: Chem. 2008, 225:27-31.
7. Shen H.Y., Judeh Z.M.A., Ching C.B. Selective alkylation of phenol with tert-butyl alcohol catalyzed by [bmim]PF6. Tetrahedron Lett. 2003, 44:981-983.
8. Shen H.Y., Judeh Z.M.A., Ching C.B., Xia Q.H. Comparative studies on alkylation of phenol with tert-butyl alcohol in the presence of liquid or solid acid catalysts in ionic liquids. J. Mol. Catal. A: Chem. 2004, 212:301-308.
9. Bhatt N., Sharma P., Patel A., Selvam P. Supported 12-tungstophosphoricacid: an efficient and selective solid acid catalyst for tert-butylation of phenol and cresols. Catal. Commun. 2008, 9:1545-1550.
10. Kirk R.D., Othmer D.F. Kirk-Othmer Encyclopedia of Chemical Technology 1978, vol. 2. Wiley Interscience, New York. 3rd ed.
11. Carlton A.A. Alkylation of phenol with tert-butyl alcohol in the presence of perchloric acid. J. Org. Chem. 1948, 13:120.
12. Welton T. Room-temperature ionic liquids, solvents for synthesis and catalysis. Chem. Rev. 1999, 99:2071-2084.
13. Chowdhury S., Mohan R.S., Scott J.L. Reactivity of ionic liquids. Tetrahedron 2007, 63:2363-2389.
14. Wasserscheid P., Keim W. Ionic liquids-new solutions for transition metal catalysis. Angew. Chem. 2000, 39:3772-3789.
15. Sheldon R. Catalytic reactions in ionic liquids. Chem. Commun. 2001, 2399-2407.
16. Plechkova N.V., Seddon K.R. Applications of ionic liquids in the chemical industry. Chem. Soc. Rev. 2008, 37:123-150.
17. Couling D.J., Bernot R.J., Docherty K.M., Dixon J.K., Maginn E.J. Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure-property relationship modeling. Green Chem. 2006, 8:82-90.
18. Elavarasan P., Kishore K.V., Upadhyayula S. Relative acidity measurement of Bronsted acid functional ionic liquids by UV-spectroscopy. Bull. Catal. Soc. India 2009, 8:107-113.
19. Fraga-Dubreuil J., Bourahla K., Rahmounc M., Pierre J., Hamelin J. Catalysed esterifications in room temperature ionic liquids with acidic counteranion as recyclable reaction media. Catal. Commun. 2002, 3:185-190.
20. Gui J., Cong X., Liu D., Zhang X., Hu Z., Sun Z. Novel Brønsted acidic ionic liquid as efficient and reusable catalyst system for esterification. Catal. Commun. 2004, 5:473-477.
21. Subramanian S., Mitra A., Satyanarayana C.V.V., Chakrabarty D.K. Para-selective butylation of phenol over silicoaluminophosphate molecular sieve SAPO-11 catalyst. Appl. Catal. A: Gen. 1997, 159:229-240.
22. Laidler K.J. Chemical Kinetics 2007, Pearson Education Inc., New Delhi.
23. Yuceer M., Atasoy I., Berber R. A software for parameter estimation in dynamic models. Braz. J. Chem. Eng. 2008, 25:813-821.
24. Yadav G.D., Doshi N.S. Alkylation of phenol with methyl-tert-butyl ether and tert-butanol over solid acids: efficacies of clay-based catalysts. Appl. Catal. A: Gen. 2002, 236:129-147.
25. Helfferich F.G. Kinetics of Multistep Reactions 2004, Elsevier, Amsterdam. 2nd ed.
26. Roberson R.E., Koshy K.M., Annessa A., Ong J.N., Scott J.M.W., Blandamer M.J. kinetics of solvolysis in water of four secondary alky nitrates. Can. J. Chem. 1982, 60:1980-1985.
27. Wold S., Ahlberg P. Evaluation of activation parameter for a first order reaction from one kinetic experiments. Theory, numerical methods and computer program. Acta Chem. Scand. 1970, 24:618-632.