Supersaturation control in cooling polymorphic co-crystallization of caffeine and glutaric acid

Crystal Growth and Design

Volumn 11, Issue 10, 2011, Pages 4525-4532

  Yu, Zai Qun ^a   Chow, Pui Shan ^a   Tan, Reginald B H ^a,b   Ang, Wei Han ^a  

^a INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ATR FTIR; ATTENUATED TOTAL REFLECTANCE FOURIER TRANSFORM INFRARED SPECTROSCOPY; CO-CRYSTALS; COCRYSTALLIZATION; GLUTARIC ACID; METASTABLE FORM; VISION MEASUREMENT;

ACETONITRILE; FOURIER TRANSFORM INFRARED SPECTROSCOPY; SUPERSATURATION;

CRYSTALLIZATION;

EID: 80053544222     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg200745q     Document Type: Article

References (39)

1. Friscic, T.; Jones, W. Benefits of cocrystallisation in pharmaceutical materials science: an update J. Pharm. Pharmacol. 2010, 62 (11) 1547-1559
2. Landenberger, K. B.; Matzger, A. J. Cocrystal engineering of a prototype energetic material supramolecular chemistry of 2,4,6-trinitrotoluene Cryst. Growth Des. 2010, 10 (12) 5341-5347
3. Good, D. J.; Rodriguez-Hornedo, N. Solubility advantage of pharmaceutical cocrystals Cryst. Growth Des. 2009, 9 (5) 2252-2264
4. Hickey, M. B.; Peterson, M. L.; Scoppettuolo, L. A.; Morrisette, S. L.; Vetter, A.; Guzman, H.; Remenar, J. F.; Zhang, Z.; Tawa, M. D.; Haley, S.; Zaworotko, M. J.; Almarsson, O. Performance comparison of a co-crystal of carbamazepine with marketed product Eur. J. Pharm. Biopharm. 2007, 67 (1) 112-119 (Pubitemid 46991320)
5. Jung, M. S.; Kim, J. S.; Kim, M. S.; Alhalaweh, A.; Cho, W.; Hwang, S. J.; Velaga, S. P. Bioavailability of indomethacin-saccharin cocrystals J. Pharm. Pharmacol. 2010, 62 (11) 1560-1568
6. Urbanus, J.; Roelands, C. P. M.; Verdoes, D.; Jansens, P. J.; ter Horst, J. H. Co-Crystallization as a separation technology: controlling product concentrations by co-crystals Cryst. Growth Des. 2010, 10 (3) 1171-1179
7. Gonnade, R. G.; Iwama, S.; Mori, Y.; Takahashi, H.; Tsue, H.; Tamura, R. Observation of efficient preferential enrichment phenomenon for a cocrystal of (dl)-phenylalanine and fumaric acid under nonequilibrium crystallization conditions Cryst. Growth Des. 2011, 11 (2) 607-615
8. Sheikh, A. Y.; Rahim, S. A.; Hammond, R. B.; Roberts, K. J. Scalable solution cocrystallization: case of carbamazepine-nicotinamide I CrystEngComm 2009, 11 (3) 501-509
9. Yu, Z. Q.; Chew, J. W.; Chow, P. S.; Tan, R. B. H. Recent advances in crystallization control-An industrial perspective Chem. Eng. Res. Des. 2007, 85 (A7) 893-905 (Pubitemid 47241483)
10. Myerson, A. S., Handbook of Industrial Crystallization, 2nd ed.; Butterworth-Heinemann: New York, 2002.
11. Yu, Z. Q.; Chow, P. S.; Tan, R. B. H. Seeding and constant- supersaturation control by ATR-FTIR in anti-solvent crystallization Org. Process Res. Dev. 2006, 10 (4) 717-722 (Pubitemid 44196602)
12. Bernstein, J.; Dunitz, J. D.; Gavezzotti, A. Polymorphic perversity: crystal structures with many symmetry-independent molecules in the unit cell Cryst. Growth Des. 2008, 8 (6) 2011-2018
13. Fujiwara, M.; Nagy, Z. K.; Chew, J. W.; Braatz, R. D. First-principles and direct design approaches for the control of pharmaceutical crystallization J. Process Control 2005, 15 (5) 493-504 (Pubitemid 40206600)
14. Yu, Z. Q.; Chow, P. S.; Tan, R. B. H. Application of attenuated total reflectance-Fourier transform infrared (ATR-FTIR) technique in the monitoring and control of anti-solvent crystallization Ind. Eng. Chem. Res. 2006, 45 (1) 438-444 (Pubitemid 43075951)
15. Rohani, S.; Sarkar, D.; Jutan, A. Multi-objective optimization of seeded batch crystallization processes Chem. Eng. Sci. 2006, 61 (16) 5282-95 (Pubitemid 43927672)
16. Nagy, Z. K.; Braatz, R. D. Robust nonlinear model predictive control of batch processes AIChE J. 2003, 49 (7) 1776-1786 (Pubitemid 36871177)
17. Chen, Z. P.; Morris, J.; Borissova, A.; Khan, S.; Mahmud, T.; Penchev, R.; Roberts, K. J. On-line monitoring of batch cooling crystallization of organic compounds using ATR-FTIR spectroscopy coupled with an advanced calibration method Chemom. Intell. Lab. Syst. 2009, 96 (1) 49-58
18. Hermanto, M. W.; Chow, P. S.; Tan, R. B. H. Implementation of focused beam reflectance measurement (FBRM) in antisolvent crystallization to achieve consistent product quality Cryst. Growth Des. 2010, 10 (8) 3668-3674
19. Chadwick, K.; Davey, R.; Sadiq, G.; Cross, W.; Pritchard, R. The utility of a ternary phase diagram in the discovery of new co-crystal forms CrystEngComm 2009, 11 (3) 412-414
20. Chiarella, R. A.; Davey, R. J.; Peterson, M. L. Making co-crystals the utility of ternary phase diagrams Cryst. Growth Des. 2007, 7 (7) 1223-1226
21. Gagniere, E.; Mangin, D.; Puel, F.; Bebon, C.; Klein, J. P.; Monnier, O.; Garcia, E. Cocrystal formation in solution: in situ solute concentration monitoring of the two components and kinetic pathways Cryst. Growth Des. 2009, 9 (8) 3376-3383
22. Yu, Z. Q.; Chow, P. S.; Tan, R. B. H. Operating regions in cooling cocrystallization of caffeine and glutaric acid in acetonitrile Cryst. Growth Des. 2010, 10 (5) 2382-2387
23. Mullin, J. W. Crystallization, 4th ed.; Butterworth-Heinemann: Oxford, 2001.
24. Rodriguez-Hornedo, N.; Nehru, S. J.; Seefeldt, K. F.; Pagan-Torres, Y.; Falkiewicz, C. J. Reaction crystallization of pharmaceutical molecular complexes Mol. Pharmaceutics 2006, 3 (3) 362-367 (Pubitemid 44021442)
25. Aher, S.; Dhumal, R.; Mahadik, K.; Paradkar, A.; York, P. Ultrasound assisted cocrystallization from solution (USSC) containing a non-congruently soluble cocrystal component pair: Caffeine/maleic acid Eur. J. Pharmaceut. Sci. 2010, 41 (5) 597-602
26. Aitipamula, S.; Chow, P. S.; Tan, R. B. H. Trimorphs of a pharmaceutical cocrystal involving two active pharmaceutical ingredients: potential relevance to combination drugs CrystEngComm 2009, 11 (9) 1823-1827
27. Trask, A. V.; Motherwell, W. D. S.; Jones, W. Pharmaceutical cocrystallization: Engineering a remedy for caffeine hydration Cryst. Growth Des. 2005, 5 (3) 1013-1021 (Pubitemid 40755572)
28. Trask, A. V.; Motherwell, W. D. S.; Jones, W. Solvent-drop grinding: green polymorph control of cocrystallisation Chem. Commun. 2004, 7, 890-891 (Pubitemid 38530287)
29. Scholl, J.; Bonalumi, D.; Vicum, L.; Mazzotti, M.; Muller, M. In situ monitoring and modeling of the solvent-mediated polymorphic transformation of l -glutamic acid Cryst. Growth Des. 2006, 6 (4) 881-891 (Pubitemid 43672323)
30. Hu, Y. R.; Liang, J. K.; Myerson, A. S.; Taylor, L. S. Crystallization monitoring by Raman spectroscopy: Simultaneous measurement of desupersaturation profile and polymorphic form in flufenamic acid systems Ind. Eng. Chem. Res. 2005, 44 (5) 1233-1240 (Pubitemid 40293444)
31. Nehm, S. J.; Rodriguez-Spong, B.; Rodriguez-Hornedo, N. Phase solubility diagrams of cocrystals are explained by solubility product and solution complexation Cryst. Growth Des. 2006, 6 (2) 592-600 (Pubitemid 43242126)
32. Beckmann, W. Seeding the desired polymorph: Background, possibilities, limitations, and case studies Org. Process Res. Dev. 2000, 4 (5) 372-383
33. Saranteas, K.; Bakale, R.; Hong, Y. P.; Luong, H.; Foroughi, R.; Wald, S. Process design and scale-up elements for solvent mediated polymorphic controlled tecastemizole crystallization Org. Process Res. Dev. 2005, 9 (6) 911-922 (Pubitemid 41784115)
34. Fevotte, G.; Alexandre, C.; Nida, S. O. A population balance model of the solution-mediated phase transition of citric acid AIChE J. 2007, 53 (10) 2578-2589 (Pubitemid 47567850)
35. Kline, B. J.; Saenz, J.; Stankovic, N.; Mitchell, M. B. Polymorph and particle size control of PPAR compounds PF00287586 and AG035029 Org. Process Res. Dev. 2006, 10 (2) 203-211 (Pubitemid 43508431)
36. Aamir, E.; Nagy, Z. K.; Rielly, C. D., Optimal seed recipe design for crystal size distribution control for batch cooling crystallisation processes. Chem. Eng. Sci. 65, (11), 3602-3614.
37. Gron, H.; Borissova, A.; Roberts, K. J. K. In-process ATR-FTIR spectroscopy for closed-loop supersaturation control of a batch crystallizer producing monosodium glutamate crystals of defined size Ind. Eng. Chem. Res. 2003, 42 (1) 198-206 (Pubitemid 36055390)
38. Hatakka, H.; Alatalo, H.; Louhi-Kultanen, M.; Lassila, I.; Haeggstrom, E. Closed-loop control of reactive crystallization PART II: polymorphism control of l-glutamic acid by sonocrystallization and seeding Chem. Eng. Technol. 2010, 33 (5) 751-756
39. Barrett, M.; McNamara, M.; Hao, H. X.; Barrett, P.; Glennon, B. Supersaturation tracking for the development, optimization and control of crystallization processes. Chem. Eng. Res. Des. 88, (8A), 1108-1119.