Precipitation of mandelic acid with a supercritical antisolvent process: Experimental and theoretical analysis, optimization, and scaleup

Industrial and Engineering Chemistry Research

Volumn 46, Issue 5, 2007, Pages 1552-1562

  Martín, Ángel ^a   Gutiérrez, Laura ^a   Mattea, Facundo ^a   Cocero, María José ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CONCENTRATION (PROCESS); MATHEMATICAL MODELS; NOZZLES; PRECIPITATION (CHEMICAL); PRESSURE EFFECTS; SUPERCRITICAL FLUIDS;

MANDELIC ACID; NOZZLE DESIGNS; SOLUTION CONCENTRATION;

CARBOXYLIC ACIDS;

CARBOXYLIC ACIDS; CONCENTRATION (PROCESS); MATHEMATICAL MODELS; NOZZLES; PRECIPITATION (CHEMICAL); PRESSURE EFFECTS; SUPERCRITICAL FLUIDS;

EID: 33947149673     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie0608051     Document Type: Article

References (24)

1. Shekunov, B. Y.; York, P. Crystallization processes in pharmaceutical technology and drug delivery design. J. Cryst. Growth 2000, 211, 122.
2. Shariati, A.; Peters, C. J. Recent developments in particle design using supercritical fluids. Curr. Opin. Solid State Mater. Sci. 2003, 7 (4-5), 371.
3. Jung, J.; Perrut, M. Particle design using supercritical fluids: Literature and patent survey. J. Supercrit. Fluids 2001, 20 (3), 179.
4. Reverchon, E. Supercritical antisolvent precipitation of micro- and nano-particles. J. Supercrit. Fluids 1999, 75 (1), 1.
5. Reverchon, E.; Della Porta, G.; Falivene, M. G. Process parameters and morphology in amoxicillin micro and submicro particles generation by supercritical antisolvent precipitation. J. Supercrit. Fluids 2000, 17 (3), 239.
6. Lengsfeld, C. S.; Delplanque, J. P.; Barocas, V. H.; Randolph, T. W. Mechanism Governing Microparticle Morphology during Precipitation by a Compressed Antisolvent: Atomization vs Nucleation and Growth. J. Phys. Chem. B 2000, 104, 2725.
7. Wubbolts, F. E.; Bruinsma, O. S. L.; van Rosmalen, G. M. Dryspraying of ascorbic acid or acetaminophen solutions with supercritical carbon dioxide. J. Cryst. Growth. 1999, 198/199, 767.
8. Reverchon, E.; De Marco, I.; Caputo, G.; Della Porta, G. Pilot scale micronization of amoxicillin by supercritical antisolvent precipitation. J Supercrit. Fluids 2003, 26 (1), 1.
9. Jarmer, D. J.; Lengsfeld, C. S.; Randolph, T. W. Scale-up criteria for an injector with a confined mixing chamber during precipitation with a compressed-fluid antisolvent. J. Supercrit. Fluids 2006, 37 (2), 242.
10. Martín, A.; Cocero, M. J. Numerical modeling of jet hydrodynamics, mass transfer and crystallization kinetics in the supercritical antisolvent (SAS) process. J. Supercrit. Fluids 2004, 32 (1-3), 203.
11. Zingg, S. P.; Arnet, E. M.; McPhail, A. T.; Bothner-By, A. A.; Gilkerson, W. R. Chiral discrimination in the structures and energetics of association of stereoisomeric salts of mandelic acid with .alpha.-phenylethylamine, ephedrine, and pseudoephedrine. J. Am. Chem. Soc. 1988, 110 (5), 1565.
12. Yu, R. J.; Van Scott, E. J. Alpha-hydroxyacids and carboxylic acids. J. Cosmet. Dermatol. 2004, 3 (2), 76.
13. Miguel, F.; Martín, A.; Gamse, T.; Cocero, M. J. Supercritical anti solvent precipitation of lycopene: Effect of the operating parameters. J. Supercrit. Fluids 2006, 36 (3), 225.
14. Lorenz, H.; Perlberg, A.; Sapoundjiev, D.; Eisner, M. P.; Seidel-Morgenstern, A. Crystallization of enantiomers. Chem. Eng. Process. 2006, 45 (10), 863.
15. Profir, V. M.; Rasmuson, A. C. Influence of Solvent and the Operating Conditions on the Crystallization of Racemic Mandelic Acid. Cryst. Growth Des. 2004, 4 (2), 315.
16. Peng, D. Y.; Robinson, D. B. A New Two-Constant Equation of State. Ind. Eng. Chem. Fundam. 1976, 15, 59.
17. Shariati, A.; Peters, C. J. Measurement and modelling of the phase behavior of ternary systems of interest for the GAS process: I. The system carbon dioxide + 1-propanol + salicylic acid. J. Supercrit. Fluids 2002, 23 (3), 195.
18. Poling, B. E.; Prausnitz, J.; O'Connell, J. P. The Properties of Gases and Liquids, 5th Edition; McGraw-Hill: New York, 2001.
19. Cheng, K. W.; Tang, M.; Chen, Y. P. Solubilities of benzoin, propyl 4-hydroxybenzoate and mandelic acid in supercritical carbon dioxide. Fluid Phase Equilib. 2002, 201 (1), 79.
20. Lorenz, H.; Sapoundjiev, D.; Seidel-Morgenstern, A. Enantiomeric Mandelic Acid System-Melting Point Phase Diagram and Solubility in Water. J. Chem. Eng. Data 2002, 47 (5), 1280.
21. Wagner, Z.; Pavlicek, J. Vapor-liquid equilibrium in the carbon dioxide-ethyl acetate system at high pressure. Fluid Phase Equilib. 1994, 97, 119.
22. Coulson, J. M.; Richardson, J. F.; Backhurst, J. R.; Harker, J. H. Coulson and Richardson's Chemical Engineering, 6th Edition; Butterworth-Heinemann: Woburn, MA, 1999; Vol. 1.
23. Vemavarapu, C.; Mollan, M. J.; Lodaya, M. Needham, T. E. Design and process aspects of laboratory scale SCF particle formation systems. Int. J. Pharm. 2005, 292 (1-2), 1.
24. Perrut, M.; Clavier, J.-Y. Supercritical Fluid Formulation: Process Choice and Scale-up. Ind. Eng. Chem. Res. 2003, 42, 6375.