Phase-Transfer Catalytic Kinetics of the Synthesis of Phenyl Benzoate

Industrial and Engineering Chemistry Research

Volumn 34, Issue 5, 1995, Pages 1572-1580

  Lee, Yao Sheng ^a   Yeh, Mou Yung ^a   Shin, Yen Ping ^a  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001712013     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie00044a009     Document Type: Article

References (29)

1. Chang, J. R.; Yeh, M. Y.; Shih, Y. P. Studies of Phase Transfer Catalytic Preparation of Benzyl Benzoate. J. Chin. Inst. Chem. Eng. 1983, 14, 457–462.
2. Chang, J. R.; Yeh, M. Y.; Shih, Y. P. Kinetics of Phase Transfer Catalytic Preparation of Benzyl Benzoate. J. Chin. Chem. Soc. 1984, 31, 185–90.
3. Do, J. S.; Chou, T. S. Kinetics of the Oxidation of Benzyl Alcohol by Hypochlorite Ion in the Presence of Phase-Transfer Catalyst. Ind. Eng. Chem. Res. 1990, 29, 1095–1103.
4. Furniss, B. S.; Hannaford, A. J.; Rogers, V.; Smith, P. W. G.; Tatchell, A. G. Vogel’s Textbook of Practical Organic Chemistry, 4th ed.; Wiley: New York, 1978.
5. Handbook of Chemistry and Physics, 61st ed.; CRC Press: Boca Raton, FL, 1980.
6. Hennis, H. E.; Easterly, J. D., Jr.; Collins, R.; Thompson, L. R. Esters from the Reactions of Alkyl Halides and Salts of Carboxylic Acids: Reactions of Primary Alkyl chlorides and Sodium Salts of Carboxylic Acids. Ind. Eng. Chem. Prod. Res. Dev. 1967, 6, 193–195.
7. Hennis, H. E.; Thompson, L. R.; Long, J. D. Esters from the Reactions of Alkyl Halides and Salts of Carboxylic Acids: Comprehensive Study of Amine Catalysis. Ind. End. Chem. Prod. Res. Dev. 1968, 7, 96–101.
8. Huang, I. D.; Dauerman, L. Exploratory Process Study: Base-Catalyzed Reaction of Organic Chlorides with Sodium Acetate. Ind. Eng. Chem. Prod. Res. Dev. 1969, 8, 227–232.
9. Hwu, D. H.; Hwang, C; Yeh, M. Y.; Jung, H. M.; Shih, Y. P. Kinetics of Phase-Transfer Synthesis Benzyl Esters Using Tertiary Amines. Ind. Eng. Chem. Res. 1990, 29, 2214–2221.
10. Hwu, D. H.; Hwang, C; Shih, Y. P.; Yeh, M. Y.; Chao, C. L. Kinetics of the Synthesis of Benzyl Ethers Using Tertiary Amines as Catalysts. Ind. Eng. Chem. Res. 1992, 31, 177–182.
11. Ulis, V. O. Phase Transfer Catalyzed Acylation. Tetrahedron Lett. 1979, 2431–2432.
12. Koening, K. E.; Weber, W. P. Synthesis of Benzoyl Cyanides by Phase-Transfer Catalysis. Tetrahedron Lett. 1974, 2275–2278.
13. Kuo, C. S.; Jwo, J. J. Inverse Phase-Transfer Catalysis. Kinetics and Mechanism of the Pyridine 1-Oxide-Catalyzed Substitution Reaction of Benzoyl Chloride and Benzoate Ion in a Two-Phase Water/Dichloromethane Medium. J. Org. Chem. 1992, 57, 1991–1995.
14. Landini, D.; Maia, A.; Rampoldi, M. Stability of Quaternary Onium Salts under Phase-Transfer Conditions in the Presence of Aqueous Alkaline Solutions. J. Org. Chem. 1986, 51, 3187–3191.
15. Lee, G. A.; Freedman, H. H. Phase-Transfer Oxidations with Hypochlorites: Scope and Mechanism. Isr. J. Chem. 1985, 26, 229–234.
16. Mathias, K.; Vaidya, R. A. Inverse Phase Transfer Catalysis. First Report of a New Class of Interfacial Reactions. J. Am. Chem. Soc. 1986, 108, 1093–1094.
17. Menger, F. M. Interfacial Physical Organic Chemistry, Imidazole-Catalyzed Ester Hydrolysis at a Water-Heptane Boundary. J. Am. Chem. Soc. 1970, 92, 5965–5971.
18. Merker, R. L.; Scott, M. J. The Reaction of Alkyl Halides with Carboxylic Acids and Phenols in the Presence of Tertiary Amines. J. Org. Chem. 1961, 26, 5180–5183.
19. Mills, R. H.; Farrar, M. W.; Weinkauff, O. J. Synthesis of Esters from Simple Alkyl Halides and Tertiary Amine Salts of Carboxylic Acids. Chem. Ind. 1962, Dec 29, 2144.
20. Plusquellec, D.; Roulleau, F.; Lefeuvre, M.; Brown, E., A New Synthesis of Carboxylic Carbonic Acid Anhydrides Using Phase Transfer Reactions. Tetrahedron 1988, 44, 2471–2476.
21. Rabinovitz, M.; Cohen, Y.; Halpern, M. Hydroxide Ion Initiated Reactions under Phase-Transfer Catalysis Conditions: Mechanism and Implications. Angew. Chem., Int. Ed. Engl. 1986, 25, 960–970.
22. Starks, C. M. Phase-Transfer Catalysis. I. Heterogeneous Reactions Involving Anion Transfer by Quaternary Ammonium and Phosphonium Salts. J. Am. Chem. Soc. 1971, 93, 195–199.
23. Starks, C. M.; Liotta, C. Phase-Transfer Catalysis, Principle and Techniques; Academic Press: New York, 1978; p 21.
24. Szeji, W. The Phase-Transfer Catalyzed Synthesis of Esters of Carboxylic Acids. Synthesis 1980, 5, 402–403.
25. Warner, C. C.; Yates, J. A. Kinetics and Mechanisms for the Two-Phase Reaction between Aqueous Aniline and Benzoyl Chloride in Chloroform with and without Pyridine Catalysis. J. Org. Chem. 1989, 54, 150–154.
26. Wang, T. T.; Huang, T. C.; Yeh, M. Y. Benzyl Alcohol from Phase-Transfer Catalyzed Weakly Alkaline Hydrolysis of Benzyl Chloride. Chem. Eng. Commun. 1990, 92, 139–151.
27. Wilmer, K.; Yue, X. Inverse Phase-Transfer Catalysis: Probing Its Mechanism with Compositive Transacrylation. J. Am. Chem. Soc. 1987, 109, 1278–1279.
28. Yeh, M. Y.; Guo, H. H.; Chen, L. C.; Shih, Y. P. Kinetics of Phase-Transfer Catalytic Esterification of Phthalic Acid Monobutyl Ester. Ind. Eng. Chem. Res. 1988, 27, 1582–1587.
29. Zerda, J. D. L.; Neumann, R.; Sasson, Y. Hofmann Decomposition of Quaternary Ammonium Salts under Phase-Transfer Catalytic Conditions. J. Chem. Soc, Perkin Trans. 2 1986, 823–826.