Manipulating crystal size shape, and structure

IEEE Control Systems

Volumn 26, Issue 4, 2006, Pages 70-80

  Larsen, Paul A ^a   Patience, Daniel B ^a   Rawlings, James B ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85008040101     PISSN: 1066033X     EISSN: None     Source Type: Journal    
DOI: 10.1109/MCS.2006.1657878     Document Type: Article

References (59)

1. R.W. Hartel, “Crystallization in foods,” in Handbook of Industrial Crystallization, 2nd ed., A.S. Myerson, Ed. Butterworth-Heinemann, 2002, pp. 287–304.
2. D.A. Green, Du Pont Magazine, Nov./Dec. 1988.
3. Semiconductor Industry Association, “Total semiconductor world market sales and shares,” 2005 [Online]. Available: http://www.sia-online.org.
4. Milken Institute, “Biopharmaceutical industry contributions to state and U.S. economies,” 2004 [Online]. Available: http://www.milkeninstitute.org
5. M. Birch, S.J. Fussell, P.D. Higginson, N. McDowall, and I. Marziano, “Towards a PAT-based strategy for crystallization development,” Org. Process Res. Dev., vol. 9, no. 3, pp. 360–364,2005.
6. R.D. Braatz and S. Hasebe, “Particle size and shape control in crystallization processes,” in Proc. Chemical Process Control—CPC 6, Tucson, Arizona, Jan. 2001, pp. 307–327.
7. J.B. Rawlings, S.M. Miller, and W.R. Witkowski, “Model identification and control of solution crystallization processes: A review,” Ind. Eng. Chem. Res., vol. 32, no. 7, pp. 1275–1296, July 1993.
8. J. Bauer, S. Spanton, R. Henry, J. Quick, W. Dziki, W. Porter, and J. Morris, “Ritonavir: An extraordinary example of conformational polymorphism,” Pharm. Res., vol. 18, no. 6, pp. 859–866,2001.
9. L.X. Yu, R.A. Lionberger, A.S. Raw, R. D’Costa, H. Wu, and A.S. Hussain, “Applications of process analytical technology to crystallization processes,” Adv. Drug Delivery Rev., vol. 56, no. 3, pp. 349–369,2004.
10. D.D. Dunuwila, L.B. Carroll II, and K.A. Berglund, “An investigation of the applicability of attenuated total reflection infrared spectroscopy for measurement of solubility and supersaturation of aqueous citric acid solutions,” J. Cryst. Growth, vol. 137, no. 3–4, pp. 561-568,1994.
11. D.D. Dunuwila and K.A. Berglund, “ATR FTIR spectroscopy for in situ measurement of supersaturation,” J. Cryst. Growth, vol. 179, no. 1–2, pp. 185-193,1997.
12. F. Lewiner, J.P. Klein, F. Puel, and G. Fevotte, “Online ATR FTIR measurement of supersaturation during solution crystallization processes. Calibration and applications on three solute/solvent systems,” Chem. Eng. Sci., vol. 56, no. 6, pp. 2069–2084, 2001.
13. T. Togkalidou, M. Fujiwara, S. Patel, and R.D. Braatz, “Solute concentration prediction using chemometrics and ATR-FTIR spectroscopy,” J. Cryst. Growth, vol. 231, no. 4, pp. 534-543,2001.
14. G. Fevotte, “New perspectives for the online monitoring of pharmaceutical crystallization processes using in situ infrared spectroscopy,” Int. J. Pharm., vol. 241, no. 5, pp. 263–278, 2002.
15. W. Doyle, “Technical note AN-923. A user's guide to: Spectroscopic analysis for industrial applications,” Axiom Analytical, Inc., Irvine, CA, Tech. Rep., Jan. 2005.
16. C. Deeley, R. Spragg, and T. Threlfall, “A comparison of Fourier-transform infrared and near-infrared Fourier-transform Raman-spectroscopy for quantitative measurements—an application in polymorphism,” Spectrochimi-ca Acta A, vol. 47, no. 9–10, pp. 1217-1223,1991.
17. F. Wang, J.A. Wachter, F.J. Antosz, and K.A. Berglund, “An investigation of solvent-mediated polymorphic transformation of progesterone using in situ Raman spectroscopy,” Org. Process Res. Dev., vol. 4, no. 5, pp. 391–395, 2000.
18. C. Starbuck, A. Spartalis, L. Wai, J. Wang, P. Fernandez, C.M. Lindemann, G.X. Zhou, and Z. Ge, “Process optimization of a complex pharmaceutical polymorphic system via in situ Raman spectroscopy,” Cryst. Growth Des., vol. 2, no. 6, pp. 515-522,2002.
19. P. Agarwal and K.A. Berglund, “In situ monitoring of calcium carbonate polymorphs during batch crystallization in the presence of polymeric additives using Raman spectroscopy,” Cryst. Growth Des., vol. 3, no. 6, pp. 941–946, 2003.
20. T. Ono, J. Ter Horst, and P. Jansens, “Quantitative measurement of the polymorphic transformation of L-glutamic acid using in-situ Raman spectroscopy,” Cryst. Growth Des., vol. 4, no. 3, pp. 465-469,2004.
21. L.E. O’Brien, P. Timmins, A.C. Williams, and P. York, “Use of in situ FT-Raman spectroscopy to study the kinetics of the transformation of carba-mazepine polymorphs,” J. Pharm. Biomed. Anal., vol. 36, no. 2, pp. 335–340, 2004.
22. J.A. Falcon and K.A. Berglund, “Monitoring of antisolvent addition crystallization with Raman spectroscopy,” Cryst. Growth Des., vol. 3, no. 6, pp. 947-952,2003.
23. Y. Hu, J.K. Liang, A.S. Myerson, and L.S. Taylor, “Crystallization monitoring by Raman spectroscopy: Simultaneous measurement of desupersatu-ration profile and polymorphic form in ufenamic acid systems,” Ind. Eng. Chem. Res., vol. 44, no. 5, pp. 1233-1240,2005.
24. B. O'sullivan, P. Barrett, G. Hsiao, A. Carr, and B. Glennon, “In situ monitoring of polymorphic transitions,” Org. Process Res. Dev., vol. 7, no. 6, pp. 977-982,2003.
25. T. Norris, P.K. Aldridge, and S.S. Sekulic, “Determination of end-points for polymorph conversions of crystalline organic compounds using online near-infrared spectroscopy,” Analyst, vol. 122, no. 6, pp. 549-552,1997.
26. G. Fevotte, J. Calas, F. Puel, and C. Hoff, “Applications of NIR spectroscopy to monitoring and analyzing the solid state during industrial crystallization processes,” Int. J. Pharm., vol. 273, no. 1–2, pp. 159-169,2004.
27. P. Barrett and B. Glennon, “In-line FBRM monitoring of particle size in dilute agitated suspensions,” Part. Part. Syst. Charact., vol. 16, no. 5, pp. 207-211,1999.
28. P. Barrett and B. Glennon, “Characterizing the metastable zone width and solubility curve using Lasentec FBRM and PVM,” Chem. Eng. Res. Des., vol. 80, no. A7, pp. 799–805, 2002.
29. M. Li and D. Wilkinson, “Determination of nonspherical particle size distribution from chord length measurements. Part 1: Theoretical analysis,” Chem. Eng. Sci., vol. 60, no. 12, pp. 3251-3265,2005.
30. J. Worlitschek, T. Hocker, and M. Mazzotti, “Restoration of PSD from chord length distribution data using the method of projections onto convex sets,” Part. Part. Syst. Charact., vol. 22, no. 2, pp. 81–98, Aug. 2005.
31. J. Calderon De Anda, X. Wang, X. Lai, and K. Roberts, “Classifying organic crystals via in-process image analysis and the use of monitoring charts to follow polymorphic and morphological changes,” J. Proc. Contr., vol. 15, no. 7, pp. 785–797, 2005.
32. I. Weissbuch, L. Addadi, M. Lahav, and L. Leiserowitz, “Molecular recognition at crystal interfaces,” Science, vol. 253, no. 5020, pp. 637-645,1991.
33. N. Blagden, R. Davey, R. Rowe, and R. Roberts, “Disappearing poly-morphs and the role of reaction by-products: The case of sulphathiazole,” Int. J. Pharm., vol. 172, no. 1–2, pp. 169-177,1998.
34. I. Weissbuch, M. Lahav, and L. Leiserowitz, “Toward stereochemical control, monitoring, and understanding of crystal nucleation,” Cryst. Growth Des., vol. 3, no. 2, pp. 125–150, 2003.
35. C.A. Mitchell, L. Yu, and M.D. Ward, “Selective nucleation and discovery of organic polymorphs through epitaxy with single crystal substrates,” J. Amer. Chem. Soc., vol. 123, no. 44, pp. 10830–10839, 2001.
36. M. Wulkow, A. Gerstlauer, and U. Nieken, “Modeling and simulation of crystallization processes using PARSIVAL,” Chem. Eng. Sci., vol. 56, no. 7, pp. 2575–2588, 2001.
37. D.L. Marchisio, R.D. Vigil, and R.O. Fox, “Quadrature method of moments for aggregation-breakage processes,” J. Colloid Interface Sci., vol. 258, no. 2, pp. 322–334, 2003.
38. S. Motz, S. Mannal, and E.-D. Gilles, “Integral approximation—an approach to reduced models for particulate processes,” Chem. Eng. Sci., vol. 59, no. 25, pp. 987–1000, 2004.
39. J. Sanyal, D.L. Marchisio, R.O. Fox, and K. Dhanasekharan, “On the comparison between population balance models for CFD simulation of bubble columns,” Ind. Eng. Chem. Res., vol. 44, no. 14, pp. 5063–5072, 2005.
40. G. Clydesdale, R. Docherty, and K.J. Roberts, “HABIT—a program for predicting the morphology of molecular crystals,” Comput. Phys. Commun., vol. 64, no. 2, pp. 311-328,1991.
41. D. Winn and M. Doherty, “A new technique for predicting the shape of solution-grown organic crystals,” AIChE J., vol. 44, no. 11, pp. 2501–2514, 1998.
42. S. Boerrigter, G. Josten, J. van de Streek, F. Hollander, J. Los, H. Cuppen, P. Bennema, and H. Meekes, “MONTY: Monte Carlo crystal growth on any crystal structure in any crystallographic orientation; application to fats,” J. Phys. Chem. A., vol. 108, no. 27, pp. 5894–5902, 2004.
43. A.L. Rohl, “Computer prediction of crystal morphology,” Current Opinion Solid State Material Sci., vol. 7, no. 7, pp. 21–26, 2003.
44. S.L. Price, “The computational prediction of pharmaceutical crystal structures and polymorphism,” Advanced Drug Delivery Revs., vol. 56, no. 3, no. 1, pp. 301–319, Feb. 2004.
45. S. Datta and D.J.W. Grant, “Crystal structure of drugs: Advances in determination, prediction and engineering,” Nature Revs. Drug Discovery, vol. 3, no. 1, pp. 42–57, Jan. 2004.
46. V. Liotta and V. Sabesan, “Monitoring and feedback control of supersaturation using ATR-FTIR to produce an active pharmaceutical ingredient of a desired crystal size,” Org. Process Res. Dev., vol. 8, no. 3, pp. 488–494, 2004.
47. H. Gron, A. Borissova, and K. Roberts, “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., vol. 42, no. 1, pp. 198–206, 2003.
48. L. Feng and K.A. Berglund, “ATR-FTIR for determining optimal cooling curves for batch crystallization of succinic acid,” Cryst. Growth Des., vol. 2, no. 5, pp. 449–452, 2002.
49. M. Fujiwara, P.S. Chow, D.L. Ma, and R.D. Braatz, “Paracetamol crystallization using laser backscattering and ATR-FTIR spectroscopy: Metastability, agglomeration, and control,” Cryst. Growth Des., vol. 2, no. 5, pp. 363–370, 2002.
50. N. Doki, H. Seki, K. Takano, H. Asatani, M. Yokota, and N. Kubota, “Process control of seeded batch cooling crystallization of the metastable—form glycine using an in-situ ATR-FTIR spectrometer and an in-situ FBRM particle counter,” Cryst. Growth Des., vol. 4, no. 5, pp. 949–953, 2004.
51. D.B. Patience and J.B. Rawlings, “Particle-shape monitoring and control in crystallization processes,” AIChE J., vol. 47, no. 9, pp. 2125–2130, 2001.
52. S.M. Miller and J.B. Rawlings, “Model identification and control strategies for batch cooling crystallizers,” AIChE J., vol. 40, no. 8, pp. 1312–1327, Aug. 1994.
53. S.H. Chung, D.L. Ma, and R.D. Braatz, “Optimal seeding in batch crystallization,” Can. J. Chem. Eng., vol. 77, no. 3, pp. 590-596,1999.
54. J. Worlitschek and M. Mazzotti, “Model-based optimization of particle size distribution in batch-cooling crystallization of paracetamol,” Cryst. Growth Des., vol. 4, no. 5, pp. 891–903, 2004.
55. S. Rohani and G. Zhang, “Online optimal control of a seeded batch cooling crystallizer,” Chem. Eng. Sci., vol. 58, no. 9, pp. 1887–1896, 2003.
56. D. Shi, N.H. El-Farra, M. Li, P. Mhaskar, and P.D. Christofides, “Predictive control of particle size distribution in particulate processes,” Chem. Eng. Sci., vol. 61, no. 1, pp. 268–281, 2006.
57. U. Vollmer and J. Raisch, “Population balance modelling and H-infinity—controller design for a crystallization process,” Chem. Eng. Sci., vol. 57, no. 20, pp. 4401-414, 2002.
58. J.B. Rawlings, C.W. Sink, and S.M. Miller, “Control of crystallization processes,” in Handbook of Industrial Crystallization, 2nd ed., A.S. Myerson, Ed. Butterworth-Heinemann, pp. 201–230, 2002.
59. P.A. Larsen, J.B. Rawlings, and N.J. Ferrier, “An algorithm for analyzing noisy, in situ images of high-aspect-aspect ratio crystals to monitor particle size distribution,” Chem. Eng. Sci., to be published.