An in situ high pressure FTIR study on molecular interactions of ketones, esters, and amides with dense phase carbon dioxide

Journal of Supercritical Fluids

Volumn 46, Issue 2, 2008, Pages 197-205

  Akiyama, Y ^a   Fujita, S ^a   Senboku, H ^a   Rayner, C M ^b   Brough, S A ^b   Arai, M ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

Carbonyl compounds; FTIR; Molecular interactions; Pressure effect; Substituent effect; Supercritical carbon dioxide

Indexed keywords

AMIDES; CARBON DIOXIDE; CARBONYLATION; ESTERIFICATION; ESTERS; FLOW INTERACTIONS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; KETONES; PRESSURE;

CARBONYL COMPOUNDS; DENSE PHASE; FTIR STUDIES; HIGH PRESSURE (HP); IN-SITU;

ORGANIC COMPOUNDS;

EID: 47949109009     PISSN: 08968446     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.supflu.2008.03.009     Document Type: Article

References (34)

1. Rayner C.M. The potential of carbon dioxide in synthetic organic chemistry. Org. Proc. Res. Develop. 11 (2007) 121-132
2. 2 in green chemical synthesis and processing. J. Supercrit. Fluids 28 (2004) 121-191
3. In: Jessop P.G., and Leitner W. (Eds). Chemical Synthesis Using Supercritical Fluids (1999), Wiley-VCH, Weinheim
4. 2 binding to carbonyl groups. J. Phys. Chem. A 102 (1998) 7860-7863
5. 2. J. Am. Chem. Soc. 124 (2002) 12590-12599
6. 2: evidence for cooperative C{single bond}H⋯O interactions. J. Phys. Chem. A 107 (2003) 10311-10323
7. Kazarian S.G., Vincent M.F., Bright F.V., Liotta C.L., and Eckert C.A. Specific intermolecular interaction of carbon dioxide with polymers. J. Am. Chem. Soc. 118 (1996) 1729-1736
8. 2 and Leis bases from FTIR spectroscopy. J. Phys. Chem. 100 (1996) 10837-10848
9. Park Y.-K., and Turner C.H. Does solvent density play a role in the keto-enol tautomerism of acetylacetone?. J. Supercrit. Fluids 37 (2006) 201-208
10. 2 and polymers having different chain groups. J. Supercrit. Fluids 36 (2006) 236-244
11. 2 by FTIR spectroscopy. J. Supercrit. Fluids 27 (2003) 283-295
12. 2 based on FTIR spectroscopy. J. Phys. Chem. B 101 (1997) 10918-10922
13. 1H NMR spectroscopy. J. Phys. Chem. B 104 (2000) 2749-2758
14. 13C NMR spectroscopic evaluation of the affinity of carbonyl compounds for carbon dioxide under supercritical conditions. Angew. Chem. Int. Ed. 43 (2004) 3719-3722
15. Zhao F., Fujita S., Sun J., Ikushima Y., and Arai M. Carbon dioxide expanded liquid substrate phase: an effective medium for selective hydrogenation of cinnamaldehyde to cinnamyl alcohol. Chem. Commun. (2000) 2326-2327
16. 2 medium with a Pt/C catalyst: a study on molecular interactions and pressure effects. J. Phys. Chem. A 109 (2005) 4419-4424
17. Liu R., Zhao F., Fujita S., and Arai M. Selective hydrogenation of citral with transition metal complexes in supercritical carbon dioxide. Appl. Catal. A: Gen. 316 (2007) 127-133
18. 2 pressure of 3 MPa and the maximum conversion is larger by a factor of 3 compared with that obtained under ambient pressure.
19. C.M. Rayner, S.A. Brough, unpublished results.
20. Fujita S., Akihara S., Zhao F., Liu R., Hasegawa M., and Arai M. Selective hydrogenation of cinnamaldehyde using ruthenium-phosphine complex catalysts with multiphase reaction systems in and under pressurized carbon dioxide: significance of pressurization and interfaces for the control of selectivity. J. Catal. 236 (2005) 101-111
21. Fujita S., Okamura S., Akiyama Y., and Arai M. Hydroformylation of cyclohexene with carbon dioxide and hydrogen using ruthenium carbonyl catalysts: influence of pressures of gaseous components. Int. J. Mol. Sci. 8 (2007) 749-759
22. Ha T.-K., Pal C., and Ghosh P.N. Ethyl acetate: gas phase infrared spectra, ab initio calculation of structure and vibrational frequencies and assignment. Spectrochim. Acta A 48 (1992) 1083-1090
23. Lopez-Anreus E., Garrigues S., and de la Guardia M. Simultaneous vapour phase Fourier transform infrared spectrometric determination of butyl acetate, toluene and methyl ethyl ketone in paint solvents. Analyst 123 (1998) 1247-1252
24. Ikushima Y., Saito N., Arai M., and Arai K. Solvent polarity parameters of supercritical carbon dioxide as measured by infrared spectroscopy. Bull. Chem. Soc. Jpn. 64 (1991) 2224-2229
25. Ikushima Y., Saito N., and Arai M. Supercritical carbon dioxide as reaction medium: examination of its solvent effects in the near-critical region. J. Phys. Chem. 96 (1992) 2293-2297
26. T(30) values of supercritical carbon dioxide at various pressures and temperatures. Liebigs Ann./Recueil (1997) 1195-1199
27. Reichardt C. Solvents and Solvent Effects in Organic Chemistry. 3rd ed. (2003), Wiley-VCH, Weinheim
28. Moriyoshi T., Kita T., and Uosaki Y. Static relative permittivity of carbon dioxide and nitrous oxide up to 30 MPa. Ber. Bunsenges. Phys. Chem. 97 (1993) 589-596
29. Hyatt J.A. Liquid and supercritical carbon dioxide as organic solvents. J. Org. Chem. 49 (1984) 5097-5101
30. Clayden J., Greeves N., Warren S., and Wothers P. Organic Chemistry (2001), Oxford University Press, Oxford
31. Streitwieser Jr. A., and Heathcock C.H. Introduction to Organic Chemistry. 3rd ed. (1985), Macmillan, New York
32. Nakanishi K., and Solomon P.H. Infrared Absorption Spectroscopy. 2nd ed. (1977), Holden-Day, San Francisco
33. Rabinovitz M., and Pines A. Hindered internal rotation and dimerization of N,N-dimethylformamide in carbon tetrachloride. J. Am. Chem. Soc. 91 (1969) 1585-1589
34. α{single bond}H⋯O{double bond, long}C hydrogen bond?. J. Am. Chem. Soc. 122 (2000) 4750-4755