Alkylation Reactions in Near-Critical Water in the Absence of Acid Catalysts

Industrial and Engineering Chemistry Research

Volumn 36, Issue 12, 1997, Pages 5175-5179

  Chandler, Karen ^a   Deng, Fenghua ^a   Dillow, Angela K ^a   Liotta, Charles L ^a   Eckert, Charles A ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYSTS; COMPOSITION EFFECTS; IONIZATION OF LIQUIDS; IONS; PHENOLS; SOLVENTS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS; WATER;

HYDRONIUM IONS;

ALKYLATION;

EID: 0031353141     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie9702688     Document Type: Article

References (24)

1. Akerlof, G. C.; Oshry, H. I. The Dielectric Constant of Water at High Temperatures and in Equilibrium with Vapor. J. Am. Chem. Soc. 1950, 72, 2844-2847.
2. Brain, G.; Loupy, A.; Majdoub, M.; Petit, A. Anthraquinone Microwave-Induced Synthesis in Dry Media in Domestic Ovens. Chem. Ind. (London) 1991, 11, 396-397.
3. Connolly, J. F. Solubility of Hydrocarbons in Water Near the Critical Solution Temperatures. J. Chem. Eng. Data 1966, 11, 13-16.
4. Gao, J. Supercritical Hydration of Organic Compounds. The Potential of Mean Force for Benzene Dimer in Supercritical Water. J. Am. Chem. Soc. 1993, 115, 6893-6895.
5. Hart, H.; Haglund, E. A. Orientation in the Phosphoric Acid-Catalyzed Alkylation of Ortho-Cresol. J. Org. Chem. 1956, 15, 396-399.
6. Holliday, R. L.; King, J. W.; List, G. R. Hydrolysis of Vegetable Oils in Sub- and Supercritical Water. Ind. Eng. Chem. Res. 1997, 36, 932-935.
7. Huston, R. C.; Lewis, W. C. Action of Aromatic Alcohols on Aromatic Compounds in the Presence of Aluminum Chloride. VII. Condensation of Benzyl Alcohol with Para-Cresol. J. Am. Chem. Soc. 1931, 53, 2379-2382.
8. Katritzky, A. R.; Murugan, R.; Balasubramanian, M.; Siskin, M. Aqueous High-Temperature Chemistry of Carbo- and Heterocycles. 10. Aquathermolysis of Acyclic and Cyclic Phenol Ethers in the Presence of Sodium Bisulfite or Phosphoric Acid. Energy Fuels 1990, 4, 543-546.
9. Katritzky, A. R.; Allin, S. M.; Siskin, M. Aquathermolysis: Reactions of Organic Compounds with Superheated Water. Acc. Chem. Res. 1996, 29, 399-406.
10. Kuhlmann, B.; Arnett, E. M.; Siskin, M. Classical Organic Reactions in Pure Superheated Water. J. Org. Chem. 1994, 59, 3098-3101.
11. Marshall, W. L.; Franck, E. U. Ion Product of Water Substance, 0-1000 °C, 1-10,000 Bars, New International Formulation and Its Background. J. Phys. Chem. Ref. Data 1981, 10, 295-304.
12. Narayan, R.; Antal, M. J. Kinetic Elucidation of the Acid-Catalyzed Mechanism of 1-Propanol Dehydration in Supercritical Water. In ACS Symposium Series; Johnston, K. P., Penninger, J. M. L., Eds.; American Chemical Society: Washington, DC, 1989; Vol. 406, p 226.
13. Parsons, E. J. Organic Reactions in Very Hot Water. CHEMTECH 1996, 26, 30-34.
14. Penninger, J. M. L. Reactions of di-n-Butylphthalate in Water at Near-Critical Temperature and Pressure. Fuel 1988, 67, 490-496.
15. Pitzer, K. S. Dielectric Constant of Water at Very High Temperature and Pressure. Proc. Natl. Acad. Sci. USA 1983, 80, 4575-4576.
16. Pospisil, J. Mechanistic Action of Phenolic Antioxidants in Polymers - A Review. Polym. Degrad. Stab. 1988, 20, 181-202.
17. Roberts, R. M.; Khalaf, A. A. Friedel-Crafts Alkylation Chemistry: a Century of Discovery; Marcel Dekker, Inc.: New York, 1984.
18. Savage, P. E.; Gopalan, S.; Mizan, T. I.; Martino, C. J.; Brock, E. E. Reactions at Supercritical Conditions: Applications and Fundamentals. AiChE J. 1995, 41, 1723-1778.
19. Sears, C. A. Alkylation of Phenol with t-Butyl Alcohol in the Presence of Perchloric Acid. J. Org. Chem. 1948, 13, 120-122.
20. Shaw, R. W.; Brill, T. B.; Clifford, A. A.; Eckert, C. A.; Franck, E. U. Supercritical Water a Medium for Chemistry. Chem. Eng. News 1991, 69, 26-39.
21. Siskin, M.; Brons, G.; Vaughn, S. N.; Katritzky, A. R.; Balasubramanian, M. Aqueous Organic Chemistry. 3. Aquathermolysis: Reactivity of Ethers and Esters. Energy Fuels 1990, 4, 488-492.
22. Sowa, F. J.; Hennion, G. F.; Nieuwland, J. A. Organic Reactions with Boron Fluoride. IX. The Alkylation of Phenol with Alcohols. J. Am. Chem. Soc. 1935, 57, 709-711.
23. Torry, L. A.; Kaminsky, R.; Klein, M. T.; Klotz, M. R. The Effect of Salts on Hydrolysis in Supercritical and Near-Critical Water: Reactivity and Availability. J. Supercrit. Fluids 1992, 5, 163-168.
24. Xu, X.; Antal, M. J.; Anderson, D. G. M. Mechanism and Temperature-Dependent Kinetics of the Dehydration of tert-Butyl Alcohol in Hot Compressed Liquid Water. Ind. Eng. Chem. Res. 1997, 36, 23-41.