Diastereomeric salt precipitation based resolution of ibuprofen by gas antisolvent method

Journal of Supercritical Fluids

Volumn 118, Issue , 2016, Pages 48-53

  Lőrincz, László ^a   Bánsághi, György ^a   Zsemberi, Máté ^a   de Simón Brezmes, Sandra ^b   Szilágyi, Imre Miklós ^a   Madarász, János ^a   Sohajda, Tamás ^c   Székely, Edit ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b UNIVERSITY OF VALLADOLID   (Spain)

^c CycloLab Cyclodextrin Research & Development Laboratory Ltd   (Hungary)

Author keywords

Crystallization; Gas antisolvent process; Resolution; Supercritical antisolvent process; Supercritical carbon dioxide

Indexed keywords

CARBON DIOXIDE; CRYSTALLIZATION; DRUG PRODUCTS; GRAIN SIZE AND SHAPE; METHANOL; OPTICAL RESOLVING POWER; ORGANIC SOLVENTS; PRECIPITATION (CHEMICAL); SOLVENTS;

CRYSTAL SIZE DISTRIBUTIONS; DIASTEREOMERIC PURITY; DIASTEREOMERIC SALTS; GAS ANTI-SOLVENT PROCESS; OPERATIONAL PARAMETERS; SUPERCRITICAL ANTISOLVENT PROCESS; SUPERCRITICAL CARBON DIOXIDES; SUPERCRITICAL GAS;

SUPERCRITICAL FLUID EXTRACTION;

EID: 84982757102     PISSN: 08968446     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.supflu.2016.07.021     Document Type: Article

References (19)

1. [1] Adams, S.S., Bresloff, P., Mason, C.G., Pharmacological differences between the optical isomers of ibuprofen: evidence for metabolic inversion of the (−)-isomer. J. Pharm. Pharmacol. 28:3 (1976), 256–257.
2. [2] Gallagher, P.M., Coffey, M., Krukonis, V., Hillstrom, W., Gas anti-solvent recrystallization of RDX: formation of ultra-fine particles of a difficult-to-comminute explosive. J. Supercrit. Fluids 5:2 (1992), 130–142.
3. [3] Reverchon, E., Adami, R., Nanomaterials and supercritical fluids. J. Supercrit. Fluids 37:1 (2006), 1–22.
4. 2-antisolvent techniques on size distribution and crystal lattice of theophylline. J. Supercrit. Fluids 57:3 (2011), 267–277.
5. [5] Rossmann, M., Braeuer, A., Leipertz, A., Schluecker, E., Manipulating the size, the morphology and the polymorphism of acetaminophen using supercritical antisolvent (SAS) precipitation. J. Supercrit. Fluids 82 (2013), 230–237.
6. [6] Neurohr, C., Erriguible, A., Laugier, S., Subra-Paternault, P., Challenge of the supercritical antisolvent technique SAS to prepare cocrystal-pure powders of naproxen-nicotinamide. Chem. Eng. J. 303 (2016), 238–251.
7. [7] Jung, J., Perrut, M., Particle design using supercritical fluids: literature and patent survey. J. Supercrit. Fluids 20:3 (2001), 179–219.
8. [8] Debenedetti, P.G., Tom, J.W., Sang-Do, Y., Gio-Bin, L., Application of supercritical fluids for the production of sustained delivery devices. J. Control. Release 24:1 (1993), 27–44.
9. [9] Reverchon, E., De Marco, I., Supercritical antisolvent precipitation of Cephalosporins. Powder Technol. 164:3 (2006), 139–146.
10. [10] Reverchon, E., De Marco, I., Mechanisms controlling supercritical antisolvent precipitate morphology. Chem. Eng. J. 169:1 (2011), 358–370.
11. 2 at low temperature. J. Supercrit. Fluids 94 (2014), 91–101.
12. [12] Chen, W., Hu, X., Hong, Y., Su, Y., Wang, H., Li, J., Ibuprofen nanoparticles prepared by a PGSS™-based method. Powder Technol. 245 (2013), 241–250.
13. [13] Martín, A., Cocero, M., Separation of enantiomers by diastereomeric salt formation and precipitation in supercritical carbon dioxide: application to the resolution of mandelic acid. J. Supercrit. Fluids 40:1 (2007), 67–73.
14. 2: a novel technique for the separation of chiral drugs. J. Pharm. Sci. 88:8 (1999), 786–791.
15. [15] Bánsághi, G.y., Lőrincz, L., Szilágyi, I.M., Madarász, J., Székely, E., Crystallization and resolution of cis-permethric acid with carbon dioxide antisolvent. Chem. Eng. Technol. 37:8 (2014), 1417–1421.
16. [16] Bánsághi, G.y., Székely, E., Sevillano, D.M., Juvancz, Z., Simándi, B., Diastereomer salt formation of ibuprofen in supercritical carbon dioxide. J. Supercrit. Fluids 69 (2012), 113–116.
17. [17] Johannsen, M., Separation of enantiomers of ibuprofen on chiral stationary phases by packed column supercritical fluid chromatography. J. Chromatogr. A 937:1-2 (2001), 135–138.
18. 2 as an anti-solvent for chiral separations. Proceedings of the AIChE Annual Meeting, Dallas, 1999.
19. [19] Ebbers, E.J., Plum, B.J., Ariaans, G.J., Kaptein, B., Broxterman, Q.B., Bruggink, A., Zwanenburg, B., New resolving bases for ibuprofen and mandelic acid: qualification by binary phase diagrams. Tetrahedron: Asymmetry 8:24 (1997), 4047–4057.