Solubility of small-chain carboxylic acids in supercritical carbon dioxide

Sparks, Darrell L.; Estevez, L. Antonio; Hernandez, Rafael; McEwen, Jason; French, Todd

doi:10.1021/je100504h

Title: Solubility of small-chain carboxylic acids in supercritical carbon dioxide

Journal Article · 07 July 2010 · Journal of Chemical and Engineering Data

DOI: https://doi.org/10.1021/je100504h · OSTI ID:1079590

Sparks, Darrell L. ^[1]; Estevez, L. Antonio ^[2]; Hernandez, Rafael ^[3]; McEwen, Jason ^[3]; French, Todd ^[3]

Mississippi State Univ., Mississippi State, MS (United States); Mississippi State University
Univ. of Puerto Rico, Mayaguez (Puerto Rico)
Mississippi State Univ., Mississippi State, MS (United States)

The solubility of heptanoic acid and octanoic acid in supercritical carbon dioxide has been determined at temperatures of (313.15, 323.15, and 333.15) K over a pressure range of (8.5 to 30.0) MPa, depending upon the solute. The solubility of heptanoic acid ranged from a solute concentration of (0.08 ± 0.03) kg • m^-3 (T = 323.15 K, p = 8.5 MPa) to (147 ± 0.2) kg • m^-3 (T = 323.15 K, p = 20.0 MPa). The lowest octanoic acid solubility obtained was a solute concentration of (0.40 ± 0.1) kg • m^-3 (T = 333.15 K, p = 10.0 MPa), while the highest solute concentration was (151 ± 2) kg • m^-3 (T = 333.15 K, p = 26.7 MPa). In addition, solubility experiments were performed for nonanoic acid in supercritical carbon dioxide at 323.15 K and pressures of (10.0 to 30.0) MPa to add to the solubility data previously published by the authors. In general, carboxylic acid solubility increased with increasing solvent density. The results also showed that the solubility of the solutes decreased with increasing molar mass at constant supercritical-fluid density. Additionally, the efficacy of Chrastil's equation and other density-based models was evaluated for each fatty acid.

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Research Organization:: Mississippi State Univ., Mississippi State, MS (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE)

Grant/Contract Number:: FG36-06GO86025

OSTI ID:: 1079590

Report Number(s):: DOE/GO--8602531

Journal Information:: Journal of Chemical and Engineering Data, Journal Name: Journal of Chemical and Engineering Data Journal Issue: 11 Vol. 55; ISSN 0021-9568

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (44)

Solubility of fatty acids in supercritical carbon dioxide Maheshwari, P.; Nikolov, Z. L.; White, T. M. Journal of the American Oil Chemists' Society, Vol. 69, Issue 11 https://doi.org/10.1007/bf02541039	journal	November 1992
Permanganate oxidation of oleic acid using emulsion technology Garti, Imissim; Avni, Eitan Journal of the American Oil Chemists' Society, Vol. 58, Issue 8 https://doi.org/10.1007/bf02665593	journal	August 1981
Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification Metzger, J. O.; Bornscheuer, U. Applied Microbiology and Biotechnology, Vol. 71, Issue 1 https://doi.org/10.1007/s00253-006-0335-4	journal	June 2006
Liquid-phase catalytic oxidation of unsaturated fatty acids Noureddini, H.; Kanabur, M. Journal of the American Oil Chemists' Society, Vol. 76, Issue 3 https://doi.org/10.1007/s11746-999-0236-7	journal	March 1999
Supercritical fluid extraction with carbon dioxide and ethylene Adachi, Yoshinori; Lu, Benjamin C. -Y. Fluid Phase Equilibria, Vol. 14 https://doi.org/10.1016/0378-3812(83)80120-4	journal	January 1983
Phase equilibria of supercritical CO2 - fatty oil component binary systems Bharath, Ragunath; Yamane, Seichiro; Inomata, Hiroshi Fluid Phase Equilibria, Vol. 83 https://doi.org/10.1016/0378-3812(93)87021-r	journal	February 1993
Solubilities of fatty acids, fatty acid esters, triglycerides, and fats and oils in supercritical carbon dioxide Yu, Zer-Ran; Singh, Bhajmohan; Rizvi, Syed S. H. The Journal of Supercritical Fluids, Vol. 7, Issue 1 https://doi.org/10.1016/0896-8446(94)90006-x	journal	March 1994
Polymerization of soybean oil via permanganate oxidation with sub/supercritical CO2 Mercangöz, M.; Küsefoğlu, S.; Akman, U. Chemical Engineering and Processing: Process Intensification, Vol. 43, Issue 8 https://doi.org/10.1016/j.cep.2003.10.002	journal	August 2004
Evaluation of density-based models for the solubility of solids in supercritical carbon dioxide and formulation of a new model Sparks, Darrell L.; Hernandez, Rafael; Estévez, L. Antonio Chemical Engineering Science, Vol. 63, Issue 17 https://doi.org/10.1016/j.ces.2008.05.031	journal	September 2008
Solubilities of palmitic and stearic fatty acids in supercritical carbon dioxide Garlapati, Chandrasekhar; Madras, Giridhar The Journal of Chemical Thermodynamics, Vol. 42, Issue 2 https://doi.org/10.1016/j.jct.2009.08.001	journal	February 2010
Solubility behavior of ternary systems of lipids, cosolvents and supercritical carbon dioxide and processing aspects Güçlü-Üstündağ, Özlem; Temelli, Feral The Journal of Supercritical Fluids, Vol. 36, Issue 1 https://doi.org/10.1016/j.supflu.2005.03.002	journal	November 2005
Solubility of hexanoic acid and butyl acetate in supercritical carbon dioxide Ghaziaskar, Hassan S.; Nikravesh, M. Fluid Phase Equilibria, Vol. 206, Issue 1-2 https://doi.org/10.1016/s0378-3812(02)00319-9	journal	April 2003
Correlating the Solubility Behavior of Fatty Acids, Mono-, Di-, and Triglycerides, and Fatty Acid Esters in Supercritical Carbon Dioxide Industrial & Engineering Chemistry Research, Vol. 39, Issue 12 https://doi.org/10.1021/ie0001523	journal	November 2000
An improved equation for predicting the solubility of vegetable oils in supercritical carbon dioxide Del Valle, Jose M.; Aguilera, Jose M. Industrial & Engineering Chemistry Research, Vol. 27, Issue 8 https://doi.org/10.1021/ie00080a036	journal	August 1988
Solubility of solids and liquids in supercritical gases Chrastil, Josef The Journal of Physical Chemistry, Vol. 86, Issue 15 https://doi.org/10.1021/j100212a041	journal	July 1982
Solid solubilities of methoxyphenylacetic acid isomer compounds in supercritical carbon dioxide Lee, Hyung Keun; Kim, Choon Ho; Kim, Sunwook Journal of Chemical & Engineering Data, Vol. 39, Issue 1 https://doi.org/10.1021/je00013a046	journal	January 1994
Supercritical Fluid−Solid Phase Equilibria Calculations by Cubic Equations of State and Empirical Equations: Application to the Palmitic Acid + Carbon Dioxide System Gordillo, Dolores; Pereyra, Clara; Martínez de la Ossa, Enrique J. Journal of Chemical & Engineering Data, Vol. 49, Issue 3 https://doi.org/10.1021/je0340598	journal	April 2004
Solubility of Azelaic Acid in Supercritical Carbon Dioxide Sparks, Darrell L.; Hernandez, Rafael; Estévez, L. Antonio Journal of Chemical & Engineering Data, Vol. 52, Issue 4 https://doi.org/10.1021/je600572z	journal	June 2007
Solubility of Nonanoic (Pelargonic) Acid in Supercritical Carbon Dioxide Sparks, Darrell L.; Estévez, L. Antonio; Hernandez, Rafael Journal of Chemical & Engineering Data, Vol. 53, Issue 2 https://doi.org/10.1021/je700465u	journal	January 2008
Supercritical-fluid-assisted oxidation of oleic acid with ozone and potassium permanganate Sparks, Darrell L.; Antonio Estévez, L.; Hernandez, Rafael Green Chemistry, Vol. 11, Issue 7 https://doi.org/10.1039/b816515g	journal	January 2009
Fats and oils as oleochemical raw materials Hill, Karlheinz Pure and Applied Chemistry, Vol. 72, Issue 7 https://doi.org/10.1351/pac200072071255	journal	January 2000
The perspectives of use of high oleic sunflower for oleochemistry and energy raws Vannozzi, G. P. Helia, Vol. 29, Issue 44 https://doi.org/10.2298/hel0644001v	journal	January 2006
Solubility of fatty acids in supercritical carbon dioxide Maheshwari, P.; Nikolov, Z. L.; White, T. M. Journal of the American Oil Chemists' Society, Vol. 69, Issue 11 https://doi.org/10.1007/BF02541039	journal	November 1992
Permanganate oxidation of oleic acid using emulsion technology Garti, Imissim; Avni, Eitan Journal of the American Oil Chemists' Society, Vol. 58, Issue 8 https://doi.org/10.1007/BF02665593	journal	August 1981
Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification Metzger, J. O.; Bornscheuer, U. Applied Microbiology and Biotechnology, Vol. 71, Issue 1 https://doi.org/10.1007/s00253-006-0335-4	journal	June 2006
Liquid-phase catalytic oxidation of unsaturated fatty acids Noureddini, H.; Kanabur, M. Journal of the American Oil Chemists' Society, Vol. 76, Issue 3 https://doi.org/10.1007/s11746-999-0236-7	journal	March 1999
Supercritical fluid extraction with carbon dioxide and ethylene Adachi, Yoshinori; Lu, Benjamin C. -Y. Fluid Phase Equilibria, Vol. 14 https://doi.org/10.1016/0378-3812(83)80120-4	journal	January 1983
Phase equilibria of supercritical CO2 - fatty oil component binary systems Bharath, Ragunath; Yamane, Seichiro; Inomata, Hiroshi Fluid Phase Equilibria, Vol. 83 https://doi.org/10.1016/0378-3812(93)87021-R	journal	February 1993
Solubilities of fatty acids, fatty acid esters, triglycerides, and fats and oils in supercritical carbon dioxide Yu, Zer-Ran; Singh, Bhajmohan; Rizvi, Syed S. H. The Journal of Supercritical Fluids, Vol. 7, Issue 1 https://doi.org/10.1016/0896-8446(94)90006-X	journal	March 1994
Solubility of hexanoic acid and butyl acetate in supercritical carbon dioxide Ghaziaskar, Hassan S.; Nikravesh, M. Fluid Phase Equilibria, Vol. 206, Issue 1-2 https://doi.org/10.1016/S0378-3812(02)00319-9	journal	April 2003
Polymerization of soybean oil via permanganate oxidation with sub/supercritical CO2 Mercangöz, M.; Küsefoğlu, S.; Akman, U. Chemical Engineering and Processing: Process Intensification, Vol. 43, Issue 8 https://doi.org/10.1016/j.cep.2003.10.002	journal	August 2004
Evaluation of density-based models for the solubility of solids in supercritical carbon dioxide and formulation of a new model Sparks, Darrell L.; Hernandez, Rafael; Estévez, L. Antonio Chemical Engineering Science, Vol. 63, Issue 17 https://doi.org/10.1016/j.ces.2008.05.031	journal	September 2008
Solubilities of palmitic and stearic fatty acids in supercritical carbon dioxide Garlapati, Chandrasekhar; Madras, Giridhar The Journal of Chemical Thermodynamics, Vol. 42, Issue 2 https://doi.org/10.1016/j.jct.2009.08.001	journal	February 2010
Solubility behavior of ternary systems of lipids, cosolvents and supercritical carbon dioxide and processing aspects Güçlü-Üstündağ, Özlem; Temelli, Feral The Journal of Supercritical Fluids, Vol. 36, Issue 1 https://doi.org/10.1016/j.supflu.2005.03.002	journal	November 2005
Correlating the Solubility Behavior of Fatty Acids, Mono-, Di-, and Triglycerides, and Fatty Acid Esters in Supercritical Carbon Dioxide Industrial & Engineering Chemistry Research, Vol. 39, Issue 12 https://doi.org/10.1021/ie0001523	journal	November 2000
An improved equation for predicting the solubility of vegetable oils in supercritical carbon dioxide Del Valle, Jose M.; Aguilera, Jose M. Industrial & Engineering Chemistry Research, Vol. 27, Issue 8 https://doi.org/10.1021/ie00080a036	journal	August 1988
Solubility of solids and liquids in supercritical gases Chrastil, Josef The Journal of Physical Chemistry, Vol. 86, Issue 15 https://doi.org/10.1021/j100212a041	journal	July 1982
Solid solubilities of methoxyphenylacetic acid isomer compounds in supercritical carbon dioxide Lee, Hyung Keun; Kim, Choon Ho; Kim, Sunwook Journal of Chemical & Engineering Data, Vol. 39, Issue 1 https://doi.org/10.1021/je00013a046	journal	January 1994
Supercritical Fluid−Solid Phase Equilibria Calculations by Cubic Equations of State and Empirical Equations: Application to the Palmitic Acid + Carbon Dioxide System Gordillo, Dolores; Pereyra, Clara; Martínez de la Ossa, Enrique J. Journal of Chemical & Engineering Data, Vol. 49, Issue 3 https://doi.org/10.1021/je0340598	journal	April 2004
Solubility of Azelaic Acid in Supercritical Carbon Dioxide Sparks, Darrell L.; Hernandez, Rafael; Estévez, L. Antonio Journal of Chemical & Engineering Data, Vol. 52, Issue 4 https://doi.org/10.1021/je600572z	journal	June 2007
Solubility of Nonanoic (Pelargonic) Acid in Supercritical Carbon Dioxide Sparks, Darrell L.; Estévez, L. Antonio; Hernandez, Rafael Journal of Chemical & Engineering Data, Vol. 53, Issue 2 https://doi.org/10.1021/je700465u	journal	January 2008
Supercritical-fluid-assisted oxidation of oleic acid with ozone and potassium permanganate Sparks, Darrell L.; Antonio Estévez, L.; Hernandez, Rafael Green Chemistry, Vol. 11, Issue 7 https://doi.org/10.1039/b816515g	journal	January 2009
Fats and oils as oleochemical raw materials Hill, Karlheinz Pure and Applied Chemistry, Vol. 72, Issue 7 https://doi.org/10.1351/pac200072071255	journal	January 2000
The perspectives of use of high oleic sunflower for oleochemistry and energy raws Vannozzi, G. P. Helia, Vol. 29, Issue 44 https://doi.org/10.2298/HEL0644001V	journal	January 2006

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
HEPTANOIC ACID
NONANOIC ACID
OCTANOIC ACID
PRESSURE RANGE
density-based model
fluid densities
heptanoic acid
nonanoic acid
octanoic acids
pressure ranges
solubility data
solute concentrations
solvent density
super-critical
supercritical carbon dioxides

Title: Solubility of small-chain carboxylic acids in supercritical carbon dioxide

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References (44)

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