Zinc acetates as efficient catalysts for the synthesis of bis-isocyanate precursors

Industrial and Engineering Chemistry Research

Volumn 49, Issue 14, 2010, Pages 6362-6366

  Reixach, Elisenda ^a   Bonet, Nuria ^a   Rius Ruiz, F Xavier ^a   Wershofen, Stefan ^b   Vidal Ferran, Anton ^a,c  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b Formerly Baver Material Science AG   (Germany)

^c INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKOXYCARBONYLATION; AROMATIC DIAMINE; CATALYST LOADINGS; DIMETHYL CARBONATE; DIPHENYLMETHANE; EFFICIENT CATALYSTS; MOLAR RATIO; ZINC ACETATE;

CATALYSTS; ZINC;

TIME DOMAIN ANALYSIS;

EID: 79952474694     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie100319n     Document Type: Article

References (43)

1. Ulrich, H. Chemistry and Technology of Isocyanates; John Wiley & Sons: Chichester, 1996.
2. Babad, H.; Zeiler, A. G. Chemistry of phosgene. Chem. Rev. 1973, 73, 75.
3. Cotarca, L.; Eckert, H. Phosgenations - A Handbook; Wiley-VCH: Weinheim, 2004.
4. Butler, D. C. D.; Alper, H. Synthesis of isocyanates from carbamate esters employing boron trichloride. Chem. Commun. 1998, 23, 2575.
5. Valli, V. L. K.; Alper, H. A Simple, Convenient, and Efficient Method for the Synthesis of Isocyanates from Urethanes. J. Org. Chem. 1995, 60, 257.
6. Chong, P. Y.; Janicki, S. Z.; Pelillo, P. A. Multilevel Selectivity in the Mild and High-Yielding Chlorosilane-Induced Cleavage of Carbamates to Isocyanates. J. Org. Chem. 1998, 63, 8515.
7. Ragaini, F. Away from phosgene: reductive carbonylation of nitroarenes and oxidative carbonylation of amines, understanding the mechanism to improve performance. Dalton Trans. 2009, 32, 6251.
8. 2yPy catalytic system. J. Mol. Catal. A: Chem. 2009, 303, 43.
9. Wehman, P.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Reductive carbonylation of aromatic dinitro compounds with apalladium(phenanthroline) 2(triflate): catalyst and an aromatic carboxylic acid as cocatalyst. Chem. Commun. 1996, 2, 217.
10. Jacob, A.; Wershofen, S.; Klein, S.; Sundermeyer, J.; Mei, F. Process for the production of urethanes. Chem. Abstr. 2009, 151, 248978; WO 095164.
11. Orejon, A.; Masdeu-Bulto, A. M.; Salagre, P.; Castillon, S.; Claver, C.; Padilla, A.; Almena, B.; Serrano, F. L. Strategies for the immobilization of homogeneous catalysts and their use in the synthesis of carbamates. Ind. Eng. Chem. Res. 2008, 47, 8032.
12. 3-promoted solution and solid phase synthesis of carbonates and carbamates in the presence of TBAI. Tetrahe2002, 58, 3329.
13. Li, Q.-F.; Wang, J.-W.; Dong, W.-S.; Kang, M.-Q.; Wang, X.-K.; Peng, S.-Y. A phosgene-free process for the synthesis of methyl N-phenyl carbamate by the reaction of aniline with methyl carbamate. J. Mol. Catal. A.Chem. 2004, 212, 99.
14. Grzyb, J. A.; Shen, M.; Yoshina-Ishii, C.; Chi, W.; Brown, R. S.; Batey, R. A. Carbamoylimidazolium and thiocarbamoylimidazolium salts: novel reagents for the synthesis of ureas, thioureas, carbamates, thiocarbamates and amides. Tetrahedron 2005, 61, 7153.
15. Carafa, M.; Quaranta, E. Synthesis of organic carbamates without using phosgene. Carbonylation of amines with carbonic acid diesters. MiniRev Org. Chem. 2009, 6, 168.
16. Ono, Y. Dimethyl carbonate for environmentally benign reactions. Pure Appl. Chem. 1996, 68, 367.
17. Guo, X.; Qin, Z.; Fan, W.; Wang, G.; Zhao, R.; Peng, S.; Wang, J. Zinc Carboxylate functionalized mesoporous SBA-15 catalyst for selective synthesis of methylene-4,4'-di(phenylcarbamate). Catal. Lett. 2009, 128, 405.
18. 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.
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, 193.
20. Wang, S.; Zhang, G.; Ma, X.; Gong, J. Investigations of catalytic activity, deactivation, and regeneration of Pb(OAc)2 for methoxycarbonylation of 2,4-toluene diamine with dimethyl carbonate. Ind. Eng. Chem. Res. 2007, 46, 6858.
21. 2. Appl. Catal., A 2002, 227, 1.
22. Curini, M.; Epifano, F.; Maltese, F.; Rosati, O. Carbamate synthesis from amines and dimethyl carbonate under ytterbium triflate catalysis. Tetrahedron Lett. 2002, 43, 4895.
23. Buysch, H. J.; Krimm, H.; Richter, W. N,O-Disubstituted urethanes and their use as starting materials for organic isocyanates. Chem. Abstr. 1982, 97, 55505; EP 0048371.
24. Han, C.; Porco, J. A. Synthesis of carbamates and ureas using Zr(IV)-catalyzed exchange processes. Org. Lett. 2007, 9, 1517.
25. Distaso, M.; Quaranta, E. Sc(OTf)3-catalyzed carbomethoxylation of aliphatic amines with, dimethyl carbonate (DMC): DMC activation by η-O(C=O) coordination to Sc(III) and its relevance to catalysis. J. Catal. 2008, 253, 278.
26. 3. Appl. Catal., A 2002, 225, 43.
27. Tundo, P.; Bressanello, S.; Loris, A.; Sathicq, G. Direct Synthesis of N-methylurethanes from primary phosphines with, dimethyl carbonate. Pure Appl. Chem. 2005, 77, 1719.
28. Juarez, R.; Padilla, A.; Corma, A.; Garcia, H. Organocatalysts for the reaction of dimethyl carbonate with 2,4-diaminotoluene. Ind. Eng. Chem. Res. 2008, 47, 8043.
29. 2/HMS catalysts for the synthesis of diethyl carbonate by oxidative carbonylation of ethanol. Chem. Eng. J. 2008, 143, 220.
30. 2 catalysts for diethyl carbonate synthesis. Appl. Catal., A 2009, 366, 71.
31. Xiong, H.; Mo, W.; Hu, J.; Bai, R.; Li, G. CuCl/phen/NMI in homogeneous carbonylation for synthesis of diethyl carbonate: Highly active catalyst and corrosion inhibitor. Ind. Eng. Chem, Res. 2009, 48, 10845.
32. Rodriguez, A.; Canosa, J.; Dominguez, A.; Tojo, J. Isobaric phase equilibria of diethyl carbonate with, five alcohols at 101.3 kPa. J. Chem. Eng. Data 2002, 48, 86.
33. Heitkaemper, P.; Schieb, T.; Wershofen, S. Process for the preparation of bis(ethoxycarbonylamino)toluenes and their use in the preparation of diisocyanatotoluenes. Chem. Abstr. 1992, 119, 27834; EP 0520273.
34. Porta, F.; Cenini, S.; Pizzotti, M.; Crotti, C. Reactions of diethyl carbonate with amines catalysed by metal centres. Gazz, Chim. Ital, 1985, 115, 275.
35. Carloni, S.; De Vos, D. E.; Jacobs, P. A.; Maggi, R.; Sartori, G.; Sartorio, R. Catalytic activity of MCM-41-TBD in the selective preparation of carbamates and unsymmetrical alkyl carbonates from diethyl carbonate. J. Catal, 2002, 205, 199.
36. Murphy, W. S.; Raman, K. P. Attempted cycloaddition of Nethoxycarbonylmethyleneamine to N-ethoxycarbonylazepine: formation of 4,4'-bis(eth.oxycarbonylamino)diphenylmethane. J. Chem. Soc., Perkin Trans. 1 1981, 2, 447.
37. Aresta, M.; Dibenedetto, A.; Quaranta, E. Selective carbomethoxylation of aromatic diamines. Grgeen Chem. 1999, 1, 237.
38. Chilin, A.; Marzaro, G.; Zanatta, S.; Barbieri, V.; Pastorini, G.; Manzini, P.; Guiotto, A. A new access to quinazolines from simple anilines. Tetrahedron 2006, 62, 12351.
39. Polymerie ureas could be easily isolated by filtration from the reaction mixture. Although these polymeric ureas were not purified, MALDIMS spectrometry unequivocally revealed that a trimeric 4,4'-MDA derived urea was mainly formed under these reaction conditions together with higher oligomers.
40. 2O in open air.
41. Bis N-alkylation product 4a was not detected by HPLC.
42. Several N-alkylated carbamates and ureas were formed, as indicated by HPLC-MS; however, these were not isolated.
43. Wang, G. R.; Wang, Y. J.; Zhao, X. Q. Kinetic and technological analysis of dimethyl toluene-2,4-dicarbamate synthesis. Chem. Eng. Technol. 2005, 28, 1511.