Batch and tubular-batch crystallization of paracetamol: Crystal size distribution and polymorph formation

Crystal Growth and Design

Volumn 6, Issue 6, 2006, Pages 1407-1414

  Méndez Del Río, José R ^a   Rousseau, Ronald W ^a  

^a Georgia Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33745711826     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg060025v     Document Type: Article

References (24)

1. Midler, J. M.; Paul, E. L.; Whittington, E. F.; Futran, M.; Liu, P. D.; Hsu, J.; Pan, S.-H. Crystallization method to improve crystal structure and size. U.S. Patent 5,314,506, 1994.
2. Dauer, R.; Mokrauer, J. E.; McKeel, W. J. Dual Jet Crystallizer Apparatus. U.S. Patent 5,578,279, 1996.
3. am Ende, D. J.; Crawford, T. C.; Weston, N. P. Reactive Crystallization Method to Improve Particle Size. U.S. Patent 6,558,435, 2003.
4. Nichols, G.; Frampton, C. S. Physicochemical characterization of the orthorhombic polymorph of paracetamol crystallized from solution. J. Pharm. Sci. 1998, 87 (6), 684-693.
5. Beyer, T.; Day, G. M.; Price, S. L. The prediction, morphology, and mechanical properties of the polymorphs of paracetamol. J. Am. Chem. Soc. 2001, 123 (21), 5086-5094.
6. DiMartino, P.; Guyot-Hermann, A. M.; Gonflant, P.; Drache, M.; Guyot, J. C. A new pure paracetamol for direct compression: The orthorhombic form. Int. J. Pharm. 1996, 128 (1-2), 1-8.
7. Bürger, A.; Henck, J. O.; Hetz, S.; Rollinger, J. M.; Weissnicht, A. A.; Stottner, H. Energy/temperature diagram and compression behavior of the polymorphs of D-mannitol. J. Pharm. Sci. 2000, 89 (4), 457-468.
8. Brittain, H. G.; Fiese, E. F. Effects of pharmaceutical processing on drug polymorphs and solvates. In Polymorphism in pharmaceutical solids; Brittain, H. G., Ed.; Marcel Dekker: New York, 1999; p 331.
9. Chemburkar, S. R.; Bauer, J.; Deming, K.; Spiwek, H.; Patel, K.; Morris, J.; Henry, R.; Spanton, S.; Dziki, W.; Porter, W.; Quick, J.; Bauer, P.; Donaubauer, J.; Narayanan, B. A.; Soldani, M.; Riley, D.; McFarland, K. Dealing with the impact of ritonavir polymorphs on the late stages of bulk drug process development. Org. Process Res. Dev. 2000, 4 (5), 413-417.
10. Shan, G.; Igarashi, K.; Noda, H.; Ooshima, H. Control of solvent-mediated transformation of crystal polymorphs using a newly developed batch crystallizer (WWDJ-crystallizer). Chem. Eng. J. 2002, 85 (2-3), 169-176.
11. Igarashi, K.; Sasaki, Y.; Azuma, M.; Noda, H.; Ooshima, H. Control of polymorphs on the crystallization of glycine using a WWDJ batch crystallizer. Eng. Life Sci. 2003, 3, 159-63.
12. Brenek, S.; am Ende, D. J.; Schofield, R.; Jerdonek, C. Delivering the desired particle; Lasentec Users Forum; Charleston, SC, 2002.
13. Doki, N.; Yokota, M.; Kido, K.; Sasaki, S.; Kubota, N. Reliable and selective crystallization of the metastable alpha-form glycine by seeding. Cryst. Growth Des. 2004, 4 (1), 103-107.
14. Al-Zoubi, N.; Malamataris, S. Effects of initial concentration and seeding procedure on crystallisation of orthorhombic paracetamol from ethanolic solution. Int. J. Pharm. 2003, 260 (1), 123-135.
15. Kitamura, M. Controlling factor of polymorphism in crystallization process. J. Cryst. Growth 2002, 237, 2205-2214.
16. Davey, R. J.; Blagden, N.; Potts, G. D.; Docherty, R. Polymorphism in molecular crystals: Stabilization of a metastable form by conformational mimicry. J. Am. Chem. Soc. 1997, 119 (7), 1767-1772.
17. Trovao, M. C. N.; Cavaleiro, A. M. V.; de Jesus, J. D. P. Preparation of polymorphic crystalline phases of D-mannitol: influence of keggin heteropolyanions. Carbohydr. Res. 1998, 309 (4), 363-366.
18. Davey, R.; Garside, J. From molecules to crystallizers; Oxford University Press: Oxford, 2000;¢¢ p 81.
19. Al-Zoubi, N.; Kachrimanis, K.; Malamataris, S. Effects of harvesting and cooling on crystallization and transformation of orthorhombic paracetamol in ethanolic solution. Eur. J. Pharm. Sci. 2002, 17 (1-2), 13-21.
20. Bürger, A. Zur Interpretation von Polymorphie-Untersuchungen. Acta Pharm. Technol. 1982, 28 (1), 1-20.
21. Randolph, A. D.; Larson, M. A. Theory of particulate processes: analysis and techniques of continuous crystallization, 2nd ed.; Academic Press: San Diego, 1988.
22. Worlitschek, J.; Mazzotti, M. Model-based optimization of particle size distribution in batch-cooling crystallization of paracetamol. Cryst. Growth Des. 2004, 4 (5), 891-903.
23. Granberg, R. A.; Rasmuson, A. C. Solubility of paracetamol in pure solvents. J. Chem. Eng. Data 1999, 44 (6), 1391-1395.
24. Mendez del Rio, J. R.; Solubility and phase transitions in batch and laminar-flow tubular crystallizers. M.S. Thesis, Georgia Institute of Technology, 2004.