CO2-protected amine formation from nitrile and imine hydrogenation in gas-expanded liquids

Industrial and Engineering Chemistry Research

Volumn 43, Issue 24, 2004, Pages 7907-7911

  Xie, Xiaofeng ^a   Liotta, Charles L ^a   Eckert, Charles A ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; AMMONIUM COMPOUNDS; CARBON DIOXIDE; HYDROGENATION; SEPARATION;

GAS-EXPANDED LIQUIDS; IMINE HYDROGENATION; TUNABLE MEDIA;

AMINES;

ALCOHOL; AMINE; BENZONITRILE; BENZOPHENONE; BENZYL CYANIDE DERIVATIVE; CARBAMIC ACID DERIVATIVE; CARBON DIOXIDE; IMINE; NITRILE;

CARBON DIOXIDE;

ARTICLE; CARBON DIOXIDE TENSION; CATALYSIS; GAS CHROMATOGRAPHY; HYDROGENATION; PRECIPITATION;

EID: 9344233328     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie0498201     Document Type: Article

References (38)

1. 2 expanded methanol-an application of gas anti-solvent reactions (GASR). In Reaction Engineering for Pollution Prevention; Abrahamand, M. A., Hesketh, R. P., Eds.; Elsevier: Amsterdam, 2000; p 173.
2. 2-expanded phases. Coord. Chem. Rev. 2001, 219-221, 789.
3. Subramaniam, B.; Lyon, C. J.; Arunajatesan, V. Environmentally benign multiphase catalysis with dense phase carbon dioxide. Appl. Catal. B 2002, 37, 279.
4. Huang, Y.; Schricker, S. R.; Culbertson, B. M.; Olesik, S. V. Synthesis of poly(acrylic acid-co-itaconic acid) in carbon dioxide-methanol mixtures. J. Macromol. Sci., Chem. 2002, A39, 27.
5. Eckert, C. A.; Bush, D.; Brown, J. S.; Liotta, C. L. Tuning solvents for sustainable technology. Ind. Eng. Chem. Res. 2000, 39, 4615.
6. Zhao, J.; Olesik, S. V. Separation of dimer acids using enhanced-fluidity liquid chromatography. Anal. Chim. Acta 2001, 449, 221.
7. Lin, C.; Muhrer, G.; Mazzotti, M.; Subramaniam, B. Vapor-liquid mass transfer during gas antisolvent recrystallization: Modeling and experiments. Ind. Eng. Chem. Res. 2003, 42, 2171.
8. 2 mixtures. AIChE J. 1996, 42, 2047.
9. Arai, Y.; Sako, T.; Takebayashi, Y. Supercritical fluids: Molecular interactions, physical properties, and new applications; Springer: Berlin, New York, 2002.
10. Kiran, E. Polymerization and polymer modification reactions in near and supercritical fluids. NATO Sci. Ser., Ser. E: Appl. Sci. 2000, 366, 253.
11. Eckert, C. A.; Knutson, B. L.; Debenedetti, P. G. Super-critical fluids as solvents for chemical and materials processing. Nature (London) 1996, 383, 313.
12. 2 expanded methanol and ethylene glycol. Ind. Eng. Chem. Res. 2004, 43, 2605-2609.
13. Dibenedetto, A.; Aresta, M.; Fragale, C.; Narracci, M. Reaction of silylalkylmono- and silylalkyldi-amines with carbon dioxide: Evidence of formation of inter- and intra-molecular ammonium carbamates and their conversion into organic carbamates of industrial interest under carbon dioxide catalysis. Green Chem. 2002, 4, 439.
14. Aresta, M.; Ballivet-Tkatchenko, D.; Dell'Amico, D. B., Boschi, D.; Calderazzo, F.; Labella, L.; Bonnet, M. C.; Faure, R.; Marchetti, F. Isolation and structural determination of two derivatives of the elusive carbamic acid. Chem. Commun. 2000, 1099.
15. Hirst, L. L.; Pinkel, I. I. Absorption of carbon dioxide by amines. Di- and triethanolamine and tetramine. Ind. Eng. Chem. 1936, 28, 1313.
16. Fuerstner, A.; Ackermann, L.; Beck, K.; Hori, H.; Koch, D.; Langemann, K.; Liebl, M.; Six, C.; Leitner, W. Olefin metathesis in supercritical carbon dioxide. J. Am. Chem. Soc. 2001, 123, 9000.
17. Wittmann, K.; Wisniewski, W.; Mynott, R.; Leitner, W.; Kranemann, C. L.; Rische, T.; Eilbracht, P.; Kluwer, S.; Ernsting, J. M.; Elsevier, C. J. Supercritical carbon dioxide as solvent and temporary protecting group for rhodium-catalyzed hydroaminomethylation. Chem. Eur. J. 2001, 7, 4584.
18. Clifford, T. Fundamentals of supercritical fluids; Oxford University Press: New York, 1999.
19. Francis, A. W. Ternary systems of liquid carbon dioxide. J. Phys. Chem. 1954, 58, 1099.
20. Charpentier, P. A.; Kennedy, K. A.; DeSimone, J. M.; Roberts, G. W. Continuous polymerizations in supercritical carbon dioxide: Chain-growth precipitation polymerizations. Macromolecules 1999, 32, 5973.
21. 2 as antisolvent. J. Appl. Polym. Sci. 2003, 88, 2427.
22. De Bellefon, C.; Fouilloux, P. Homogeneous and heterogeneous hydrogenation of nitriles in a liquid phase: Chemical, mechanistic, and catalytic aspects. Catal. Rev.-Sci. Eng. 1994, 36, 459.
23. Satoh, T.; Suzuki, S.; Suzuki, Y.; Miyaji, Y.; Imai, Z. Reduction of organic compounds with sodium borohydride-transition metal salt systems. I. Reduction of organic nitrile, nitro and amide compounds to primary amines. Tetrahedron Lett. 1969, 4555.
24. James, B. R. Synthesis of chiral amines catalyzed homogeneously by metal complexes. Catal. Today 1997, 37, 209.
25. Osborn, J. A.; Schrock, R. R. Preparation and properties of some cationic complexes of rhodium(I) and rhodium(III). J. Am. Chem. Soc. 1971, 93, 2397.
26. Yoshida, T.; Okano, T.; Thorn, D. L.; Tulip, T. H.; Otsuka, S.; Ibers, J. A. Preparations and reactions of some hydrido dinitrogen trialkylphosphine complexes of rhodium(i). The structure of a dinitrogen-bridged rhodium(i) dinier, [RhH(P-iso-Pr)3)2]2-(μ-N2). J. Organomet. Chem. 1979, 181, 183.
27. Rylander, P. N. Hydrogenation Methods; Academic Press: London, Orlando, FL, 1985.
28. Caddick, S.; Haynes, A. K. D. K.; Judd, D. B.; Williams, M. R. V. Convenient synthesis of protected primary amines from nitriles. Tetrahedron Lett. 2000, 41, 3513.
29. Diaf, A.; Beckman, E. J. Foamable materials via a polymer-bound, thermally reversible carbon dioxide: Amine adduct. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 956.
30. George, M.; Weiss, R. G. Chemically reversible organogels via "latent" gelators. Aliphatic amines with carbon dioxide and their ammonium carbamates. Langmuir 2002, 18, 7124.
31. Loudon, G. M. Organic Chemistry; Oxford University Press: New York, 2002.
32. 2. J. Phys. Chem. A 2001, 105, 3947.
33. Yoshida, T.; Okano, T.; Otsuka, S. Catalytic hydrogenation of nitriles and dehydrogenation of amines with the rhodium(I) hydrido compounds [RhH[P(CHMe2)3]3] and [Rh2H2(m-n2)-[P(cyclohexyl)3]4]. J. Chem. Soc., Chem. Commun. 1979, 870.
34. Crabtree, R. H. The Organometallic Chemistry of the Transition Metals; John Wiley: New York, 2001.
35. 2. Abstracts of Papers, 221st National Meeting of the American Chemical Society, San Diego, Apr 1-5, 2001; American Chemical Society: Washington, DC, 2001; IEC.
36. Jessop, P. G.; Ikariya, T.; Noyori, R. Homogeneous catalysis in supercritical fluids. Chem. Rev. 1999, 99, 475.
37. Baiker, A. Supercritical fluids in heterogeneous catalysis. Chem. Rev. 1999, 99, 453.
38. Herrera, V.; Munoz, B.; Landaeta, V.; Canudas, N. Homogeneous hydrogenation of imines catalyzed by rhodium and iridium complexes kinetics and mechanism of the hydrogenation of N-(β-naphthylmethylene)aniline using [Ir(cod)(PPh3)2]PF6 as catalyst precursor. J. Mol. Catal. A 2001, 174, 141.