An examination of factors influencing the thermodynamics of correlation-gas chromatography as applied to large molecules and chiral separations

Journal of Chemical and Engineering Data

Volumn 55, Issue 2, 2010, Pages 698-707

  Lipkind, Dmitry ^a   Chickos, James S ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANALYTES; CHIRAL COLUMN; CHIRAL SEPARATIONS; CORRELATION-GAS CHROMATOGRAPHY; EFFECTS OF TEMPERATURE; ENDOTHERMIC ENTHALPY; ENDOTHERMICITY; ENTHALPIES OF VAPORIZATION; ENTHALPY OF TRANSFER; GASPHASE; MEAN TEMPERATURE; SENSITIVITY TO TEMPERATURES; STATIONARY PHASE; VAPORIZATION ENTHALPIES;

CHIRALITY; CHROMATOGRAPHIC ANALYSIS; ENTHALPY; PARAFFINS; VAPORIZATION;

GAS CHROMATOGRAPHY;

EID: 77249116227     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je900422c     Document Type: Conference Paper

References (43)

1. Lipkind, D.; Chickos, J. S. Hypothetical Thermodynamic Properties. Subcooled Vaporization Enthalpies and Vapor Pressures of Polyaromatic Heterocycles and Related Compounds. J. Chem. Eng. Data 2009, 54, DOI: 10.1021/je900034d.
2. Lipkin, D.; Chickos, J. S. A Examination of the Vaporization Enthalpies and Vapor Pressures of Pyrazine, Pyrimidine, Pyridazine and 1,3,5-Triazine. Struct. Chem. 2009, 20, 49-58.
3. 92 at T) 298.15 K by Correlation-Gas Chromatography. J. Chem. Eng. Data 2008, 53, 2432-2440.
4. Zhao, H.; Unhannanant, P.; Hanshaw, W.; Chickos, J. S. The Vaporization Enthalpies and Vapor Pressures of Some Deuterated Hydrocarbons. Liquid Vapor Pressure Isotope Effects. J. Chem. Eng. Data 2008, 53, 1545-1556.
5. 76 at T) 298.15 K by Correlation-Gas Chromatography. Are the Vaporization Enthalpies a Linear Function of Carbon Number. J. Chem. Eng. Data 2008, 53, 481-91.
6. Lipkind, D.; Kapustin, Y.; Umnahanant, P.; Chickos, J. S. The Vaporization Enthalpies and Vapor Pressures of a Series of Unsaturated Fatty Acids Methyl Esters by Correlation - Gas Chromatography. Thermochim. Acta 2007, 456, 94-101.
7. Umnahanant, P.; Kweskin, S.; Nichols, G.; Dunn, M. J.; Smart-Ebinne, H.; Chickos, J. S. Vaporization Enthalpies of the α, ω-Alkanediols by Correlation-Gas Chromatography. J. Chem. Eng. Data 2006, 51, 2246-2254.
8. 16. J. Chem. Thermodyn. 2005, 37, 941-953.
9. 21-C30 at T) 298.15 by Correlation-Gas Chromatography. J. Chem. Eng. Data 2004, 49, 77-85.
10. Hanshaw, W.; Nutt, M.; Chickos, J. S. Hypothetical Thermodynamic Properties. Subcooled Vaporization Enthalpies and Vapor Pressures of Polyaromatic Hydrocarbons. J. Chem. Eng. Data 2008, 53, 1903-1913.
11. Temprado, M.; Roux, M. V.; Umnahanant, P.; Zhao, H.; Chickos, J. S. Thermochemistry of 2,4-Pentanedione revisited: Observance of a Non-Zero Enthalpy of Mixing Between Tautomers and its Effects on Enthalpies of Formation. J. Phys. Chem. B 2005, 109, 12590-12595.
12. Temprado, M.; Chickos, J. S. Application of Correlation-Gas Chromatography to Evaluate the Vaporization Enthalpy of a Component in an Equilibrium Mixture. Thermochim. Acta 2005, 435, 49-56.
13. Umnahanant, P.; Chickos, J. S. The Thermochemistry of Ethyl 3-Oxobutanoate Revisited: Observance of a Non-Zero Enthalpy of Mixing Between Tautomers and Its Effects on Enthalpies of Formation. J. Chem. Eng. Data 2005, 50, 1720-26.
14. Zhao, H.; Chickos, J. S. Measurement of the Vaporization Enthalpy of Complex Mixtures by Correlation-Gas Chromatography. The Vaporization Enthalpy of RP-1, JP-7, and JP-8, R Rocket and Jet Fuels at T = 298.15K. Combust. Fuel 2005, 19, 2064-2073.
15. Chickos, J. S.; Wentz, A. E.; Hillesheim-Cox, D.; Zehe, M. J. Measurement of the Vaporization Enthalpy of Complex Mixtures by Correlation-Gas Chromatography. The Vaporization Enthalpy of RJ-4, a High-Energy Density Rocket Fuel at T = 298.15K. Ind. Eng. Chem. 2003, 42, 2874-2877.
16. Roux, M. V.; Temprado, M.; Chickos, J. S.; Nagano, Y. Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons. J. Phys. Chem. Ref. Data 2008, 37, 1855-1996.
17. Hoare, M. R.; Purnell, J. H. Temperature Effects in Gas-Liquid Partition Chromatography. Trans. Faraday Soc. 1956, 52, 222-229.
18. Peacock, L. A.; Fuchs, R. Enthalpy of Vaporization Measurements by Gas Chromatography. J. Am. Chem. Soc. 1977, 99, 5524-5525.
19. Fuchs, R.; Peacock, L. A. Heats of Vaporization and Gaseous Heats of Formation of Some Five and Six-Membered Ring Alkenes. Can. J. Chem. 1979, 57, 2302-2304.
20. 20. J. Phys. Chem. Ref. Data 1994, 23, 1-39.
21. Steele, W. V.; Archer, D. G.; Chirico, R. D.; Collier, W. B.; Hossenlopp, I. A.; Nguyen, A.; Smith, N. K.; Gammon, B. The Thermodynamic Properties of Quinoline and Isoquinoline. J. Chem. Thermodyn. 1988, 20, 1233-64.
22. Steele, W. V.; Chirico, R. D.; Hossenlopp, I. A.; Nguyen, A.; Smith, N. K.; Gammon, B. E. The Thermodynamic Properties of the Five Benzoquinolines. J. Chem. Thermodyn. 1989, 21, 81-107.
23. Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Steele, W. V. The Thermodynamic Properties to the Temperature 700 K of Naphthalene and of 2,7-Dimethylnaphthalene. J. Chem. Thermodyn. 1993, 25, 1461-1494.
24. Chirico, R. D.; Steele, W. V. Thermodynamic Properties of Diphenylmethane. J. Chem. Eng. Data 2005, 50, 1052-59.
25. 8 1-Alcohols. J. Chem. Eng. Data 2006, 51, 7-10.
26. Steele, W. V.; Chirico, R. D.; Cowell, A. B.; Knipmeyer, S. E.; Nguyen, A. Thermodynamic Properties and Ideal Gas Enthalpies of Formation for Methyl Benzoate, Ethyl Benzoate, (R-(+)-Limonene tert-Amyl Methyl Ether, trans-Crotonaldehyde, and Diethylene Glycol. J. Chem. Eng. Data 2002, 47, 667-688.
27. Ruuzicka, K.; Mokbel, I.; Majer, V.; Ruuzicka, V.; Jose, J.; Zabransky, M. Description of Vapour-Liquid and Vapour-Solid Equilibria for a Group of Polycondensed Compounds of Petroleum Interest. Fluid Phase Equilib. 1998, 148, 107-137.
28. Ambrose, D.; Ellender, J. H.; Sprake, C. H. S. Thermodynamic Properties of Organic Oxygen Compounds. XXXV. Vapor Pressures of Aliphatic Alcohols. J. Chem. Thermodvn. 1974, 6, 909-914.
29. Menthol: A) 3.2838 (5.2895 - log (101.325 kPa) ;
30. B = 1091.9;
31. C)-156.45. Stephenson, R. M.; Malanowski, S. Handbook of the Thermodynamics of Organic Compounds; Elsevier: N. Y., 1987.
32. 30) in the Temperature Range Between 350 and 460 K. J. Chem. Eng. Data 2006, 51, 854-858.
33. Bicchi, C; Brunelli, C; Cravotto, Rubiolo, P.; Galli, M.; Mendicuti, F. Cyclodextrin Derivatives in GC Separation of Racemates with Different Volatilities. Part XIX: Thermodynamic Aspects of Enantioselective GC Separations of Some Volatiles with γ-Cyclodextrins 2,3-Substituted with Methyl and Acetyl Groups. J. Sep. Sci. 2003, 26, 761-770.
34. Skorka, M.; Asztemborska, M.; Zukowski, J. Thermodynamic Studies of Complexation and Enantiorecognition Processes of Monoterpenoids by R-and β-Cyclodextrin in Gas Chromatography. J. Chromatogr. A 2005, 1078, 136-143.
35. Results reported in the Supporting Information, Tables S12 to S13 or S14.
36. Majer, V.; Svoboda, V. Enthalpies of Vaporization of Organic Compounds. A Critical ReView and Data Complilation. IUPAC, Chemical Data Series 32, Blackwell Scientific Pub.: London, UK, 1985.
37. Mean value from: N'Guimbi, J. N.; Kasehgari, H.; Mokbel, I.; Jose, J. Tensions de Vapeur d'Alcools Primaires Dans le Domaine 0,3 Pa à 1,5 KPa. Thermochim. Acta 1992, 196, 367-377.
38. Kulikov, D.; Verevkin, S. P.; Heintz, A. Enthalpies of Vaporization of a Series of Aliphatic Alcohols. Experimental Results and Values Predicted by the ERAS-Model. Fluid Phase Equilib. 2001, 4813, 1-21.
39. Chirico, R. D.; Steele, W. V. Thermodynamic Properties of 2-Methylquinoline and 8-Methylquinoline. J. Chem. Eng. Data 2005, 50, 697-708.
40. Chirico, R. D.; Johnson, R. D., III; Steele, W. V. Thermodynamic Properties of Methylquinolines. Experimental Results for 2,6-Dimethylquinoline and Mutual Validation Between Experiments and Computational Methods for Methylquinolines. J. Chem. Thermodvn. 2007, 39, 698-711.
41. Chickos, J. S.; Garin, D. L.; Hilt, M.; Schilling, G. Some Solid State Properties of Enantiomers and Their Racemates. Tetrahedron 1981, 37, 2255.
42. Abrosimov, V. K.; Smirnov, V. I.; Kuznetsov, V. A.; Okhrimenko, T. M.; Efremova, E. P. Enthalpies of Solution in Ethanol-Water Mixtures and Acetone at 298.15 K and Enthalpies of Fusion of L (-) and DL-Chloramphenicols, D (+) - and DL-Camphors and L (-) and DL-Menthols. Russ. J. Phys. Chem. 2003, 77, 1191-1193.
43. This became apparent when attempting room-temperature X-ray diffraction studies.