CO2/water-regulating transamidation of urea and amines

ACS Sustainable Chemistry and Engineering

Volumn 2, Issue 5, 2014, Pages 1147-1154

  Zhang, Ran ^a   Guo, Li ^a   Chen, Jizhong ^a   Gan, Huimei ^a   Song, Baoning ^a   Zhu, Wenwen ^a   Hua, Li ^a   Hou, Zhenshan ^a  

^a RESEARCH INSTITUTE OF INDUSTRIAL CATALYSIS   (China)

Author keywords

Ammonia scrubbing; Carbon dioxide; Green chemistry; Transamidation of urea; Urea derivatives

Indexed keywords

AMINES; METABOLISM; UREA;

BIPHASIC CONDITIONS; GREEN CHEMISTRY; REACTION MIXTURE; REACTION ROUTES; REACTION TEMPERATURE; TRANSAMIDATION; TRANSAMIDATION REACTION; UREA DERIVATIVES;

CARBON DIOXIDE;

EID: 84899996464     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc400511u     Document Type: Article

References (53)

1. Bigi, F.; Maggi, R.; Sartori, G. Selected synthesis of ureas through phosgene substitutes Green Chem. 2000, 2, 140-148
2. Estevez, S. A.; Pissinate, K.; Nascimento, M. G.; Grynberg, N. F.; Echevaria, A. Synthesis, cytotoxicity, and DNA-topoisomerase inhibitory activity of new asymmetric ureas and thioureas Bioorg. Med. Chem. 2006, 14, 492-499
3. Füldner, S.; Mitkina, T.; Trottmann, T.; Frimberger, A.; Gruber, M.; König, B. Urea derivatives enhance the photocatalytic activity of dye-modified titanium dioxide Photochem. Photobiol. Sci. 2011, 10, 623-625
4. Lamothe, M.; Perez, M.; Colovray, G. V.; Halazy, S. A simple one-pot preparation of N, N′-unsymmetrical ureas from N-Boc protected primary anilines and amines Synlett 1996, 507-508
5. Eckert, H.; Forster, B. Triphosgene, a crystalline phosgene substitute Angew. Chem., Int. Ed. Engl. 1987, 26, 894-895
6. Fujita, S.; Bhanage, B. M.; Kanamaru, H.; Arai, M. Synthesis of 1, 3-dialkylurea from ethylene carbonate and amine using calcium oxide J. Mol. Catal. A: Chem. 2005, 230, 43-48
7. Nagaraju, N.; Kuriakose, G. A new catalyst for the synthesis of N, N-biphenylurea from aniline and dimethyl carbonate Green Chem. 2002, 4, 269-271
8. 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, 99-105
9. Valli, V. L. K.; Alper, H. Reductive carbonylation of mono- and dinitroarenes catalyzed by Montmorillonitebipyridinylpalladium(II) acetate and ruthenium carbonyl J. Am. Chem. Soc. 1993, 115, 3778-3779
10. Cenini, S.; Pizzotti, M.; Crotti, C.; Porta, F.; La Monica, G. Selective ruthenium carbonyl catalysed reductive carbonylation of aromatic nitro compounds to carbarnates J. Chem. Soc. Chem. Commun. 1984, 1286-1287
11. Shi, F.; Deng, Y. Q. Polymer-Immobilized gold catalysts for the efficient and clean syntheses of carbamates and symmetric ureas by oxidative carbonylation of aniline and its derivatives J. Catal. 2002, 211, 548-551
12. Kim, H. S.; Kim, Y. J.; Lee, H.; Lee, S. D.; Chin, C. S. Oxidative carbonylation of aromatic amines by selenium compounds J. Catal. 1999, 184, 526-534
13. 6-catalyzed oxidative carbonylation of primary amines to N, N′-disubstituted ureas in single or biphasic solvent systems. Optimization and functional group compatibility studies J. Org. Chem. 2000, 65, 5216-5222
14. Díaz, D. J.; Darko, A. K.; McElwee, L. W. Transition metal-catalyzed oxidative carbonylation of amines to ureas Eur. J. Org. Chem. 2007, 4453-4465
15. Shi, F.; Deng, Y. Q.; SiMa, T. L.; Peng, J. J.; Gu, Y. L.; Qiao, B. T. Alternatives to phosgene and carbon monoxide: synthesis of symmetric urea derivatives with carbon dioxide in ionic liquids Angew. Chem., Int. Ed. 2003, 42, 3257-3260
16. 2 via base catalysis Green Chem. 2007, 9, 158-161
17. 2 activation: an unexpected catalytic activity of polymer-supported nanogold J. Am. Chem. Soc. 2005, 127, 4182-4183
18. 2 and amines with a functional ionic liquid as the catalyst Green Chem. 2008, 10, 465-469
19. 2 and amines catalyzed by polyethylene glycol supported potassium hydroxide without dehydrating agents Synlett 2010, 8, 1276-1280
20. 2 Chin. J. Chem. 2013, 31, 381
21. 2 in the absence of catalyst and solvent Green Chem. 2010, 12, 1811-1816
22. Zhang, M.; Imm, S.; Bähn, S.; Neubert, L.; Neumann, H.; Beller, M. Efficient copper(II)-catalyzed transamidation of nonactivated primary carboxamides and ureas with amines Angew. Chem., Int. Ed. 2012, 51, 1-6
23. 2O - KI - catalyzed, environmentally friendly synthesis of N, N′-disubstituted ureas in water under microwave irradiation Synth. Commun. 2005, 35, 2325-2331
24. Licence, P.; Gray, W. K.; Sokolova, M.; Poliakoff, M. Selective monoprotection of 1, n-terminal diols in supercritical carbon dioxide: a striking example of solvent tunable desymmetrization J. Am. Chem. Soc. 2005, 127, 293-298
25. Leitner, W. Supercritical carbon dioxide as a green reaction medium for catalysis Acc. Chem. Res. 2002, 35, 746-756
26. Eckert, C. A.; Liotta, C. L.; Bush, D.; Brown, J. S.; Hallett, J. P. Sustainable reactions in tunable solvents J. Phys. Chem. B 2004, 108, 18108-18118
27. Hardy, S.; Wispelaere, I. M. de; Leitner, W.; Liauw, M. A. Comprehensive monitoring of a biphasic switchable solvent synthesis Analyst 2013, 138, 819-824
28. Hallett, J. P.; Pollet, P.; Liotta, C. L.; Eckert, C. A. Reversible in situ catalyst formation Acc. Chem. Res. 2008, 41, 458-467
29. 2/aqueous biphasic media Green Chem. 2002, 4, 501-504
30. Cheng, H. Y.; Meng, X. C.; Liu, R. X.; Hao, Y. F.; Yu, Y. C.; Cai, S. X.; Zhao, F. Y. Cyclization of citronellal to p-menthane-3,8-diols in water and carbon dioxide Green Chem. 2009, 11, 1227-1231
31. 2 J. Org. Chem. 2010, 75, 257-260
32. Ferreiro, S. S.; Pereira, F. P.; Mora, I. C.; Romero, V.; Lavilla, I.; Bendicho, C. Ion pair-based liquid-phase microextraction combined with cuvetteless UV-vis micro-spectrophotometry as a miniaturized assay for monitoring ammonia in waters Talanta 2011, 85, 1448-1452
33. Tsuboi, T.; Hirano, Y.; Shibata, Y.; Motomizu, S. Sensitivity improvement of ammonia determination based on flow-injection indophenol spectrophotometry with manganese (II) ion as a catalyst and analysis of exhaust gas of thermal power plant Anal. Sci. 2002, 18, 1141-1144
34. Li, X. N.; Hagaman, E.; Tsouris, C.; Lee, J. W. Removal of carbon dioxide from flue gas by ammonia carbonation in the gas phase Energy Fuels 2003, 17, 69-74
35. 2 greenhouse gas by ammonia scrubbing Ind. Eng. Chem. Res. 1997, 36, 2490-2493
36. 13C NMR study Green Chem. 2006, 8, 995-1000
37. Coxon, B.; Fatiadi, A. J.; Sniegoski, L. T.; Hertz, H. S.; Schaffer, R. A novel acylative degradation of uric acid. Carbon-13 nuclear magnetic resonance studies of uric acid and its degradation products J. Org. Chem. 1977, 42, 3132-3140
38. 3 in organic solvents and its catalytic conversion into urea under mild conditions Green Chem. 2011, 13, 1267-1274
39. 2-protected amine formation from nitrile and Imine hydrogenation in gas-expanded liquids Ind. Eng. Chem. Res. 2004, 43, 7907-7911
40. George, M.; Weiss, R. G. Detection of pre-sol aggregation and carbon dioxide scrambling in alkylammonium alkylcarbamate gelators by nuclear magnetic resonance Langmuir 2003, 19, 8168-8176
41. Park, J. Y.; Yoon, S. J.; Lee, H. Effect of steric hindrance on carbon dioxide absorption into new amine solutions: thermodynamic and spectroscopic verification through solubility and NMR analysis Environ. Sci. Technol. 2003, 37, 1670-1675
42. 2-switchable wormlike micelles Chem. Commun. 2013, 49, 4902-4904
43. Stoimenovski, J.; Izgorodina, E. I.; MacFarlane, D. R. Ionicity and proton transfer in protic ionic liquids Phys. Chem. Chem. Phys. 2010, 12, 10341-10347
44. Jensen, M. B. Study on carbamtes XII. The carbamates of butylamines Acta Chem. Scand. 1957, 11, 499-505
45. 2 on conversion of inulin to 5- hydroxymethylfurfural and propylene oxide to 1, 2-propanediol in water Green Chem. 2010, 12, 1215-1219
46. 2 microemulsion Langmuir 1998, 14, 6371-6376
47. Aresta, M.; Tkatchenko, D. B.; Belli Dell'Amico, D.; Bonnet, M. C.; Boschi, D.; Calderazzo, F.; Faure, R.; Labella, L.; Marchetti, F. Isolation and structural determination of two derivatives of the elusive carbamic acid Chem. Commun. 2000, 1099-1100
48. 2 expanded liquid and hot water Green Chem. 2004, 382-386
49. Meessen, J. H.; Petersen, H. Urea. Ullmann's Encyclopaedia of Industrial Chemistry; Verlag GmbH and Co. KGaA, Wiley-VCH: Weinheim, 2005; pp 1-35.
50. Lu, J.; Liotta, C. L.; Eckert, C. A. Spectroscopically probing microscopic solvent properties of room-temperature ionic liquids with the addition of carbon dioxide J. Phys. Chem. A 2003, 107, 3995-4000
51. Roosen, C.; Ansorge, S. M.; Mang, T.; Leitner, W.; Greiner, L. Gaining pH-control in water/carbon dioxide biphasic systems Green Chem. 2007, 9, 455-458
52. 2 capture: a review Int. J. Greenhouse Gas Control 2012, 10, 443-455
53. Kreye, O.; Mutlu, H.; Meier, M. A. R. Sustainable routes to polyurethane precursors Green Chem. 2013, 15, 1431-1455