Investigations of catalytic activity, deactivation, and regeneration of Pb(OAc) 2 for methoxycarbonylation of 2,4-toluene diamine with dimethyl carbonate

Industrial and Engineering Chemistry Research

Volumn 46, Issue 21, 2007, Pages 6858-6864

  Wang, Shengping ^a   Zhang, Guanglin ^b   Ma, Xinbin ^a   Gong, Jinlong ^c  

^a TIANJIN UNIVERSITY   (China)

^b HEBEI UNIVERSITY OF TECHNOLOGY   (China)

^c The University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHYL CARBONATE; METHOXYCARBONYLATION; MOLAR RATIO;

ACETIC ACID; LEAD; MEASUREMENT THEORY; METHANOL; SYNTHESIS (CHEMICAL); TOLUENE; X RAY DIFFRACTION ANALYSIS;

CATALYST ACTIVITY;

ACETIC ACID; CATALYST ACTIVITY; LEAD; MEASUREMENT THEORY; METHANOL; SYNTHESIS (CHEMICAL); TOLUENE; X RAY DIFFRACTION ANALYSIS;

EID: 35548990558     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie061537+     Document Type: Conference Paper

References (22)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley: New York, 1991; p 315.
2. Fritsch, K. C.; Klempner, D. Comprehensive Polymer Science; Allen, G., Bevington, J. C., Eds.; Pergamon: New York, 1989; p 413.
3. Wan, B. S.; Liao, S. j.; Yu, D. R. Polymer-Supported Palladium-Manganese Bimetallic Catalyst for the Oxidative Carbonylation of Amines to Carbamate esters. Appl. Catal., A 1999, 183, 81-84.
4. Kim, H. S.; Kim, Y. J.; Lee, H.; Lee, S. D; Chin, C. S. Oxidative Carbonylation of Aromatic Amine by Selenium Compounds. J. Catal. 1999, 184, 526-534.
5. Cenini, S.; Crotti, C.; Pizzotti, M. Ruthenium Carbonyl Catalyzed Reductive Carbonylation of Aromatic Nitro Compounds: a Selective Route to Carbamates. J. Org. Chem. 1988, 53 (6), 1243-1250.
6. Gasperini, M.; Ragaini, F.; Cenini, S.; Gallo, E. Carbonylation of Nitrobenzene to N-methyl Phenylcarbamate Catalyzed by Palladium-Phenanthroline Complexes Bifunctional Activation by Anthranilic Acid. J. Mol. Catal. A 2003, 204-205, 107-114.
7. Reddy, N. P.; Masdeu, A. M.; Ali, B. E. Palladium Complex-Potassium Carbonate-Catalysed Reductive Carbonylation of Mono- and Dinitroaromatic Compounds. J. Chem. Soc. Chem. Commun. 1994, 7, 863-865.
8. Ariza, X.; Urpi, F.; Vilarrasa, J. A Practical Procedure for the Preparation of Carbamates from Azides. Tetrahedron Lett. 1999, 40 (42), 7515-7517.
9. Fu, Z. H.; Ono, Y. Synthesis of Methyl N-phenyl Carbamate by Methoxycarbonylation of Aniline with Dimethyl Carbonate using Pb Compounds as Catalysts. J. Mol. Catal., A 1994, 91, 399-405.
10. 3. Appl. Catal., A 2002, 225, 43-49.
11. Hans-Josef, B.; Heinrich, K.; Wolfgang, R. Process for the preparation of N,O-disubstituted urethanes. EP 48371, 1982.
12. Aldo, B.; Pietro, C.; Fausto, G Process for the production of aromatic carbamates. EP 752413, 1997.
13. Aldo, B.; Pietro, C.; Emanuele, C.; Ignazio, P. Process for the production of aromatic urethanes. EP 752414, 1997.
14. Aldo, B.; Emanuele, C.; Vittorio, C.; Pietro, C. Process for the synthesis of aromatic urethanes. EP 881213, 1998.
15. Gurgiolo, A. E.; Tex, L. J. Preparation of carbamates from aromatic amines and organic carbonates. U.S. Patent 4,268,683, 1981.
16. Gurgiolo, A. E. Preparation of carbamates from aromatic amines and organic carbonates. U.S. Patent 4,268,684, 1981.
17. Vauthey, I.; Valot, F; Gozzi, C.; Fache, F.; Lemaire, M. An Environmentally Benign Access to Carbamates and Ureas. Tetrahedron Lett. 2000, 41 (33), 6347-6350.
18. Curini, M.; Epifano, F.; Maltese, F.; Rosati, O. Carbamate Synthesis from Amines and Dimethyl Carbonate under Ytterbium Triflate Catalysis. Tetrahedron Lett. 2002, 43 (28), 4895-4897.
19. Baba, T.; Kobayashi, A.; Yamauchi, T.; Tanaka, H.; Aso, S.; Inomata, M.; Kawanami, Y. Catalytic Methoxycarbonylation of Aromatic Diamines with Dimethyl Carbonate to their Dicarbamates using Zinc Acetate. Catal. Lett. 2002, 82 (3-4), 193-197.
20. Baba, T.; Kobayashi, A.; Kawanami, Y.; Inazu, K.; Ishikawa, A.; Echizenn, T.; Murai, K.; Aso, S.; Inomata, M. Characteristics of Methoxycarbonylation of Aromatic Diamine with Dimethyl Carbonate to Dicarbamate using a Zinc Acetate Catalyst. Green Chem. 2005, 7, 159-165.
21. 2. Appl. Catal., A 2002, 227 (1-2), 1-6.
22. Wang, G. R.; Zhao, X. Q.; Wang, Y. J. Thermodynamic Analysis of Synthesis of Toluene 2,4-Dicarbamate. Chin. J. Chem. Ind. Eng. 2005, 22 (1), 8-13.