A continuous-flow o-methylation of phenols with dimethyl carbonate in a continuously fed stirred tank reactor

Industrial and Engineering Chemistry Research

Volumn 38, Issue 5, 1999, Pages 2075-2079

  Bomben, Andrea ^a   Selva, Maurizio ^a   Tundo, Pietro ^a  

^a Dipto di Sci Ambientali dell'U   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AGENTS; CARBONATES; CATALYSIS; CHEMICAL REACTORS; PHENOLS; POLYETHYLENE GLYCOLS; REACTION KINETICS;

CONTINUOUSLY FED STIRRED TANK REACTOR; CRESOL; DIMETHYL CARBONATE; METHYLATION;

ALKYLATION;

AGRICULTURAL CHEMICAL; CARBONIC ACID; CRESOL; PHENOL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; ENVIRONMENTAL FACTOR; METHODOLOGY; METHYLATION; QUANTITATIVE DIAGNOSIS; STOICHIOMETRY;

EID: 0032961447     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie9806444     Document Type: Article

References (24)

1. Dorothea, G. Phenol Derivatives. In Ullmann's Encyclopedia of Industrial Chemistry; Barbara, E., Stephen, H., Gail, S., Eds.; VCH Verlagsgesellschaft: Weinheim, Germany, 1991; Vol. A19.
2. (a) Fener, H.; Hooz, J. Methods of Formation of the Ether Linkage. In The Chemistry of the Ether Linkage; Patai, S., Ed.; Interscience Publishers: London, 1967; Chapter 10, pp 445-498.
3. (b) Hiers, G. S.; Hager, F. D. Anisole. In Organic Syntheses, 2nd ed.; Gilman, H., Blatt, A. H., Eds.; Wiley: New York, 1941; Collect. Vol. I, pp 58-60.
4. McCormack, W. B.; Lawes, B. C. Sulfuric and Sulforous Esters. In Kirk-Othmer Encyclopedia of Chemical Technology, 3rd ed.; John Wiley & Sons: New York, 1978; Vol. 22, p 236 and references therein.
5. Ono, Y. Dimethylcarbonate for Environmentally Benign Reactions. Pure Appl. Chem. 1996, 68, 367-75.
6. KiwiMinsker, L.; Porchet, S.; Doepper, R.; Renken, A. Catalyst Acid/Base Properties to Control the Selectivity in Gas-Phase Methylation of Cathecol. Stud. Surf. Sci. Catal. 1997, 108, 149-156.
7. 3+ on the Alkylation of Phenol with Methanol over Magnesium-Aluminium Calcined Hydrotalcite. Appl. Catal. A 1997, 762, 81-91.
8. (b) Velu, S.; Swamy, C. S. Selective C-Alkylation of Phenol with Methanol over Catalysts Derived from Copper-Aluminium Hydrotalcite-like Compounds. Appl. Catal. A 1996, 145, 141-153.
9. (c) Velu, S.; Swamy, C. S. Alkylation of Phenol with Methanol over Magnesium-Aluminium Hydrotalcites. Appl. Catal. A 1994, 119, 241-252.
10. Landau, M. V.; Kogan, S. B.; Tavor, D.; Herskowitz, M.; Koresh, J. E. Selectivity in Heterogeneous Catalytic Processes. Catal. Today 1997, 36, 497-510.
11. 2 Catalyst. Appl. Catal. A 1995, 133, L7-L10.
12. 3) Catalysts. 4. Catalytic Performance in the Alkylation of Phenol with Methanol. Appl. Catal. A 1993, 99, 161-173.
13. Agayev, A. A.; Tagiyev, D. B. Alkylation of Phenol by Methanol on Type-Y Zeolites. Pet. Chem. 1992, 32, 101-105.
14. Pierantozzi, R.; Nordquist, F. Selective O-alkylation of Phenol with Methanol. Appl. Catal. 1986, 21, 263-271.
15. Renaud, M.; Chantal, P. D.; Kalliaguine, S. Anisole Production by Alkylation of Phenol. Can. Chem. Eng. 1986, 64, 787-791.
16. Tundo, P.; Trotta, F.; Moraglio, G.; Ligorati, F. Continuous-Flow Processes under Gas-Liquid Phase-Transfer (GL-PTC) Conditions. The Reaction of Dialkyl carbonates with Phenols, Alcohols, and Mercaptans. Ind. Eng. Chem. Res. 1988, 27, 1565-1571.
17. (a) Tundo, P. Continuous-Flow Methods in Organic Synthesis; Ellis Horwood: Chichester, U.K., 1991.
18. (b) Tundo, P.; Selva, M. Simplify Gas-Liquid Phase-Transfer Catalysis. CHEMTECH 1995, 25 (5), 31-5.
19. (a) Fu, Z. H.; Ono, Y. Selective O-methylation of Phenol with Dimethyl carbonate over X-zeolites. Catal. Lett. 1993, 27, 43-47.
20. (b) Fu, Y.; Baba, T.; Ono, Y. Vapor-Phase Reaction of Catechol with Dimethyl carbonate. Appl. Catal. A 1998, 166, 425-430.
21. 4 Catalysts. React. Kinet. Catal. Lett. 1997, 62, 47-54.
22. 3 Catalysts. React. Kinet. Catal. Lett. 1998, 63, 261-269.
23. Carrá, S.; Morbidelli, M. Gas-Liquid Reactors. In Chemical Reaction and Reactor Engineering; Carberry, J. J., Varma, A., Eds.; Marcel Dekker: New York, 1987; Chapter 9, pp 545-666.
24. It has to be noted that the reactant mixture was sent to the reactor for about 8 h/day. After that time, the catalytic bed was cooled to 100 °C and kept under stirring overnight before restarting the reaction the next day.