Solubility Modeling of N-CBZ Derivatised Amino Acids in Supercritical Carbon Dioxide

N. Vedaraman, Pravin Gadkari, Balaraman Manohar, K. V. Sandhya, Gerd Brunner, K. Udaya Sankar

CSIR-Central Leather Research Institute, Chennai, India.
Food Engineering, CSIR—Central Food Technological Research Institute, Mysore, India.
Food Engineering, CSIR—Central Food Technological Research Institute, Mysore, India；Academy of Scientific and Innovative Research, CSIR-CFTRI, Mysore, India.
VT-2, TUHH, Hamburg, Germany.

DOI: 10.4236/ijamsc.2014.22006                

Abstract

The experimental solubility of CBZ (Carbobenzoxy) derivatized amino acids namely N-CBZ valine, N-CBZ proline, N-CBZ aspartic acid in supercritical carbon dioxide were correlated by Soave-Red- lich-Kwong Equation state based on fugacity determination and group contribution method using extrapolated critical parameters and mixing rules and other two different empirical models proposed by Yu (1994) and Gordillo-coworkers (1999). The SRK EOS prediction showed very high deviation of % AARD of 9% - 59%. The Yu model had three derivatized amino acids with average absolute deviation from 2.04, 8.17, 10.96, while the Gordillo model had 0.245, 1.067 and 1.144 for CBZ-valine, CBZ-proline and CBZ-aspartic acid successively. The correlated values had better fit with Gordillo model. The predictive capability and applicability for these amino acid derivatives for both the models demonstrated with correlation coefficient around 0.99 for all the experimental solubility observed.

Keywords

Derivatized Amino Acids, Soave-Redlich-Kwong (SRK), Yu Model, Gordillo Model

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	Caude, M. and Thiebaut, D. (1999) Practical Supercritical Fluid Chromatography and Extraction. Harwood Academic Publishers, Chur.
[2]	Erkey, C. (2000) Supercritical Carbon Dioxide Extraction of Metals from Aqueous Solutions: A Review. Journal of Supercritical Fluids, 17, 259-287. http://dx.doi.org/10.1016/S0896-8446(99)00047-9
[3]	Laintz, K.E., Wai, C.M., Yonker, C.R. and Smith, R.D. (1992) Extraction of Metal Ions from Liquid and Solid Mate- rials by Supercritical Carbon Dioxide. Analytical Chemistry, 64, 2875-2878. http://dx.doi.org/10.1021/ac00046a039
[4]	Wai, C.M. (1995) Supercritical Fluid Extraction of Trace Metals from Solid and Liquid Materials for Analytical Ap- plications. Analytical Sciences, 11, 165-167. http://dx.doi.org/10.2116/analsci.11.165
[5]	Lin, Y., Brauer, R.D., Laintz, K.E. and Wai, C.M. (1993) Supercritical Fluid Extraction of Lanthanides and Actinides from Solid Materials with a Fluorinated β-Diketone. Analytical Chemistry, 65, 2549-2551. http://dx.doi.org/10.1021/ac00066a027
[6]	Iso, S., Uno, S., Meguro, Y., Sasaki, T. and Yoshida, Z. (2000) Pressure Dependence of Extraction Behaviour of Plu- tonium (IV) and Uranium (VI) from Nitric Acid Solution to Supercritical Carbon Dioxide Containing Tributyl Phos- phate. Progress in Nuclear Energy, 37, 423-428. http://dx.doi.org/10.1016/S0149-1970(00)00082-2
[7]	Tomioka, O., Meguro, Y., Enokida, Y., Yamamoto, I. and Yoshida, Z. (2001) Dissolution Behaviour of Uranium Oxi- des with Supercritical CO2 Using HNO3-TBP Complex as a Reactant. Journal of Nuclear Science and Technology, 38, 1097-1102. http://dx.doi.org/10.1080/18811248.2001.9715141
[8]	Mincher, B.J., Fox, R.V., Holmes, R.G.G., Robbins, R.A. and Boardman, C. (2001) Supercritical Fluid Extraction of Plutonium and Americium from Soil Using Theonytrifluoroacetone and Tributylphosphate Complexation. Radiochi- mica Acta, 89, 613-617.
[9]	Lin, Y., Wai, C.M., Jean, F.M. and Brauer, R.D. (1994) Supercritical Fluid Extraction of Thorium and Uranium Ions from Solid and Liquid Materials with Fluorinated beta Diketones and Tributyl Phosphate. Environmental Science and Technology, 28, 1190-1193. http://dx.doi.org/10.1021/es00055a034
[10]	Rao, A., Kumar, P. and Ramakumar, K.L. (2010) Separation of Uranium from Different Uranium Oxide Matrices Em- ploying Supercritical Carbon Dioxide Extraction. Journal of Radioanalytical and Nuclear Chemistry, 285, 247-257. http://dx.doi.org/10.1007/s10967-010-0568-7
[11]	Smart, N.G., Carleson, T., Kast, T., Clifford, A.A., Burford, M.D. and Wai, C.M. (1997) Solubility of Chelating Agents and Metal Containing Compounds in Supercritical Fluid Carbon Dioxide. Talanta, 44, 137-150. http://dx.doi.org/10.1016/S0039-9140(96)02008-5
[12]	Kumar, R., Sivaraman, N., Senthil Vadivu, E., Srinivasan, T.G. and Vasudeva Rao, P.R. (2003) Complete Removal of Uranyl Nitrate from Tissue Matrix Using Supercritical Fluid Extraction. Radiochimica Acta, 91, 197-201. http://dx.doi.org/10.1524/ract.91.4.197.19966
[13]	Kumar, R., Sivaraman, N., Sujatha, K., Srinivasan, T.G. and Vasudeva Rao, P.R. (2007) Removal of Plutonium and Americium from Waste Matrices by Supercritical Carbon Dioxide Extraction. Radiochimica Acta, 95, 577-584. http://dx.doi.org/10.1524/ract.2007.95.10.577
[14]	Suresh Kumar, V., Kumar, R., Sivaraman, N., Ravisankar, G. and Vasudeva Rao, P.R. (2010) Design and Adaptation of a Novel Supercritical Extraction Facility for Operation in a Glove Box for Recovery of Radioactive Elements. Re- view of Scientific Instruments, 81, 094101-094106. http://dx.doi.org/10.1063/1.3484190
[15]	Kumar, R., Sivaraman, N., Sujatha, K., Srinivasan, T.G. and Vasudeva Rao, P.R. (2009) A Novel Technique for Mod- ifier Free Delivery of Ligands for Supercritical Fluid Extraction. Radiochimica Acta, 97, 443-451. http://dx.doi.org/10.1524/ract.2009.1633
[16]	Sujatha, K., Pitchaiah, K.C., Sivaraman, N., Srinivasan, T.G. and Vasudeva Rao, P.R. (2012) Recovery of Uranium and Plutonium from Waste Matrices Using Supercritical Fluid Extraction. American Journal of Analytical Chemistry, 3, 916-922. http://dx.doi.org/10.4236/ajac.2012.312A121
[17]	Sujatha, K., Pitchaiah, K.C., Sivaraman, N., Nagarajan, K., Srinivasan, T.G. and Vasudeva Rao, P.R. (2014) Recovery of Plutonium from Polymeric Waste Matrices Using Supercritical Fluid Extraction. Desalination and Water Treatment, 52, 470-475. http://dx.doi.org/10.1080/19443994.2013.808729
[18]	Brahmmananda Rao, C.V.S., Srinivasan, T.G. and Vasudeva Rao, P.R. (2012) Studies on the Extraction by Substituted Butyl Phosphonates. Solvent Extraction and Ion Exchange, 30, 262-277. http://dx.doi.org/10.1080/07366299.2011.639250
[19]	Datta, A., Sivaraman, N., Srinivasan, T.G. and Vasudeva Rao, P.R. (2011) Liquid Chromatographic Behaviour of Ac- tinides and Lanthanides on Monolith Supports. Radiochimica Acta, 99, 275-283. http://dx.doi.org/10.1524/ract.2011.1816
[20]	Suresh, A., Srinivasan, T.G. and Vasudeva Rao, P.R. (1994) Extraction of U(VI), Pu(IV) and Th(IV) by Some Trialkyl Phosphates. Solvent Extraction and Ion Exchange, 12, 727-744. http://dx.doi.org/10.1080/07366299408918234