Kinetic studies on the esterification of a substituted phenylacetic acid by phase-transfer catalysis

Industrial and Engineering Chemistry Research

Volumn 37, Issue 12, 1998, Pages 4625-4630

  Juang, Ruey Shin ^a   Liu, Shing Chaur ^a  

^a YUAN ZE UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ACTIVATION ENERGY; CATALYSTS; CAUSTIC SODA; COMPOSITION EFFECTS; ESTERIFICATION; MIXING; REACTION KINETICS; THERMAL EFFECTS;

PHASE TRANSFER CATALYSIS; PHASE TRANSFER CATALYSTS; PHENYLACETIC ACIDS;

CATALYSIS;

PHENYLACETIC ACID DERIVATIVE; SODIUM HYDROXIDE; TETRABUTYLAMMONIUM; TOLUENE;

ADSORPTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ENGINEERING; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; ESTERIFICATION; HYDROGEN BOND; HYDROLYSIS; PHASE TRANSITION; REACTION ANALYSIS; REACTION TIME; SOLUBILITY; TEMPERATURE DEPENDENCE;

EID: 0032456117     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie980226z     Document Type: Article

References (21)

1. Starks, C. M.; Liotta, G. L.; Halpern, M. E. Phase-Transfer Catalysis. Fundamentals, Applications, and Industrial Perspectives; Chapman & Hall: New York, 1994; pp 48 and 108.
2. Rabinovitz, M.; Cohen, Y.; Halpern, M. Hydroxide Ion Initiation Reactions under Phase Transfer Catalysis Conditions: Mechanism and Implications. Angew. Chem., Int. Ed. Engl. 1986, 25, 960-970.
3. Wang, M. L. Kinetic Modeling of Catalytic Phase Transfer Systems. In Handbook of Phase Transfer Catalysis; Sasson, Y., Neumann, R., Eds.; Chapman & Hall: New York, 1997; Chapter 2, pp 36-109.
4. Bhattacharya, A. General Kinetic Model for Liquid-Liquid Phase-Transfer-Catalyzed Reactions. Ind. Eng. Chem. Res. 1996, 35, 645-652.
5. Lasek, W.; Makosza, M. Adsorption at the Liquid-Liquid Interface: An Important Factor in Phase-Transfer Catalysis. J. Phys. Org. Chem. 1993, 6, 412-420.
6. Mason, D.; Magdassi, S.; Sasson, Y. Interfacial Activity of Quaternary Salts as a Guide to Catalytic Performance in Phase-Transfer Catalysis. J. Org. Chem. 1990, 55, 2714-2717.
7. Tamaki, K. Surface Activity of Tetrabutylammonium Halides in the Aqueous Solutions. Bull. Chem. Soc. Jpn. 1967, 40, 38-41.
8. Makosza, M. Two-Phase Reactions in the Chemistry of Carbanions and Halocarbenes - A Useful Tool in Organic Synthesis. Pure Appl. Chem. 1975, 43, 439-462.
9. Lele, S. S.; Bhave, R. R.; Sharma, M. M. Fast and Very Slow Reactions: Phase Transfer Catalysis. Chem. Eng. Sci. 1983, 38, 765-773.
10. Bokman, F.; Bohman, O.; Siegbahn, H. O. G. Different Surface Activity of Quaternary Ammonium and Phosphonium Ions in Formamide Solutions. Acta Chem. Scand. 1992, 46, 403-405.
11. Yeu, M. C. Synthesis of an Ether-Ester Compound via Esterification by Phase-Transfer Catalysis. M.S. Thesis, National Tsing Hua University, Hsinchu, Taiwan, 1996.
12. Juang, R. S.; Liu, S. C. Interfacial Properties on the Synthesis of Ether-Ester Compounds by Liquid-Liquid Phase-Transfer Catalysis. Ind. Eng. Chem. Res. 1997, 36, 5296-5301.
13. Halpern, M.; Sasson, Y.; Rabinovitz, M. Hydroxide Ion Initiation Reactions under Phase Transfer Catalysis Conditions. 5. Isomerization of Allylbenzene via Hydroxide Ion Extraction. J. Org. Chem. 1983, 48, 1022-1025.
14. Huang, T. C.; Lin, S. G. Kinetic of Benzylation of Isobutyraldehyde in a Toluene-Aqueous Sodium Hydroxide System with Quaternary Ammonium Iodine. J. Chin. Inst. Chem. Eng. 1988, 19, 193-200.
15. Solaro, R.; D'Antone, S.; Chiellini, E. Heterogeneous Ethylation of Phenylacetonitrile. J. Org. Chem. 1980,45, 4179-4183.
16. Wu, H. S.; Jou, S. H. Kinetics of Formation of Diphenoxymethane from Phenol and Dichloromethane Using Phase-Transfer Catalysis. J. Chem. Technol. Biotechnol. 1995,64, 325-330.
17. Wu, H. S.; Lu, M. C. Phenolyses of 1-Bromoethylbenzene by Phase-Transfer Catalysis in a Heterogeneous Two-Phase System. J. Mol. Catal. 1995, 104, 139-146.
18. Wu, H. S.; Meng, S. S. Modeling and Experimental Study of a Sequential Phosphazene Reaction by Phase-Transfer Catalysis. AIChE J. 1997,43, 1309-1318.
19. Hanna, G. J.; Noble, R. D. Measurement of Liquid-Liquid Interfacial Kinetics. Chem. Rev. 1985, 85, 583-598.
20. Laidler, K. J.; Meiser, J. H. Physical Chemistry, 2nd ed.; Houghton Mifflin: Boston, 1995; pp 827-843.
21. Amankwa, L.; Cantwell, F. F. Dissociation of Tetrahexylammonium Picrate Ion Pairs Adsorbed at the Chloroform-Water Interface. Anal. Chem. 1990, 62, 2270-2274.