Process paths of kinetically controlled crystallization: Enantiomers and polymorphs

Industrial and Engineering Chemistry Research

Volumn 42, Issue 10, 2003, Pages 2230-2244

  Schroer, Joseph W ^a,c   Ng, Ka M ^b  

^a University of Massachusetts   (United States)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^c CWB Technology Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTALS; DISSOLUTION; NUCLEATION; PHASE DIAGRAMS;

KINETIC CONSTANTS;

CRYSTALLIZATION;

ACETYL 2 (4 HYDROXYPHENYL)GLYCINE; ANTIARRHYTHMIC AGENT; ANTIBIOTIC AGENT; GALANTAMINE; HISTIDINE; L 768673; N PHTHALYL 3 AMINO 2 PHENYLPROPANOIC ACID; NAPROXEN; PHENYLGLYCINE; PROLINE; UNCLASSIFIED DRUG;

KINETICS;

ARTICLE; CHEMICAL ANALYSIS; CHIRALITY; CRYSTAL STRUCTURE; CRYSTALLIZATION; DENSITY; DISSOLUTION; ENANTIOMER; EQUILIBRIUM CONSTANT; EVAPORATION; KINETICS; MOLECULAR MODEL; PHASE TRANSITION; REACTION ANALYSIS; SOLUBILITY;

EID: 0038665548     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie020722u     Document Type: Article

References (64)

1. Wibowo, C.; Ng, K. M. Systems Engineering Approach to Chemical-Based Consumer Product Manufacture. AIChE J. 2002, 48, 1212.
2. Wibowo, C.; Ng, K. M. Unified Approach for Synthesizing Crystallization-Based Separation Processes. AIChE J. 2000, 46, 1400.
3. Samant, K. D.; Ng, K. M. Representation of High-Dimensional Solid-Liquid Phase Diagrams for Ionic Systems. AIChE J. 2001, 47, 861.
4. Schroer, J.; Wibowo, W., C.; Ng, K. M. Synthesis of Chiral Crystallization Processes. AIChE J. 2001, 47, 369.
5. Wibowo, C.; Samant, K. D.; Ng, K. M. High-Dimensional Solid-Liquid Phase Diagrams Involving Compounds and Polymorphs. AIChE J. 2002, 48, 2179.
6. Matsuoka, M.; Garside, J. The Significance of Mass and Heat Transfer during Crystal Growth. J. Cryst. Growth 1993, 129, 385.
7. Kelkar, V. V.; Ng, K. M. Design of Reactive Crystallization Systems Incorporating Kinetics and Mass Transfer Effects. AIChE J. 1999, 45, 69.
8. Spruijtenburg, R. Examples of the Selective Preparation of a Desired Crystal Modification by an Appropriate Choice of Operating Parameters. Org. Process Res. Dev. 2000, 4, 403.
9. Bada, J. L. Racemization of Amino Acids. In Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: New York, 1985.
10. Söhnel, O.; Garside, J. Precipitation: Basic Principles and Industrial Applications; Butterworth-Heinemann: Oxford, U.K., 1992.
11. Tavare, N. S. Industrial Crystallization: Process Simulation Analysis and Design; Plenum Press: New York, 1995.
12. Mahajan, A. J.; Orella, C. J.; Kirwan, D. J. Analysis of Size Distribution and Growth Kinetics during the Batch Crystallization of L-Asparagine. AIChE Symp. Ser. 1991, 284, 143.
13. Zipp, G. L.; Rodríguez-Hornedo, N. pH Effects on the Crystallization Kinetics of Phenytoin, a Monoprotic Acid. AIChE Symp. Ser. 1991, 284, 197.
14. Saska, M.; Garandet, J.-P. Kinetics of Sucrose Crystallization from Impure Solutions. AIChE Symp. Ser. 1987, 253, 42.
15. Johns, M. R.; Judge, R. A.; White, E. T. Kinetics of the Ethanolic Crystallization of Fructose. ACS Symp. Ser. 1989, 438, 198.
16. Yokota, M.; Oguchi, T.; Arai, K.; Toyokura, K.; Inoue, C.; Naijyo, H. Growth Rate of S-Carboxymethyl-D-cysteine and Its Optical Resolution. ACS Symp. Ser. 1989, 438, 271.
17. Kitamura, M.; Furukawa, H.; Asaeda, M. Solvent Effect of Ethanol on Crystallization and Growth Process of L-Histidine Polymorphs. J. Cryst. Growth. 1994, 141, 193.
18. Kitamura, M.; Sumi, Y. Growth Process and Morphological Change of β-Glutamic Acid in the Presence of L-Phenylalanine. ACS Symp. Ser. 1997, 667, 92.
19. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates, and Resolutions; John Wiley & Sons: New York, 1981.
20. Ebbers, E. J.; Ariaans, G. J. A.; Houbiers, J. P. M.; Bruggink, a.; Zwanenburg, B. Controlled Racemization of Optically Active Organic Compounds: Prospects for Asymmetric Transformation. Tetrahedron 1997, 53, 9417.
21. Tavare, S. N. Batch Crystallizers. Rev. Chem. Eng. 1991, 7, 211.
22. Mullin, J. W. Crystallization; Butterworth-Heinemann Ltd.: London, 1993.
23. Nývlt, J. The Kinetics of Industrial Crystallization; Elsevier: New York, 1985.
24. Randolph, A. D.; Larson, M. A. Theory of Particulate Processes; Academic Press: New York, 1971.
25. Chung, S. H.; Ma, D. L.; Braatz, R. D. Optimal Seeding in Batch Crystallization. Can. J. Chem. Eng. 1999, 77, 590.
26. Tucker, G. J. Sourcing Chiral Compounds for the Pharmaceutical Industry. In Handbook of Chiral Chemicals; Ager, D. J., Ed.; Marcel Dekker: New York, 1999.
27. Yamada, S.; Hongo, C.; Yoshioka, R.; Chibata, I. Method for the Racemization of Optically Active Amino Acids. J. Org. Chem. 1983, 48, 843.
28. Kawamura, K.; Yukioka, M. Kinetics of the Racemization of Amino Acids at 225-275 °C Using a Real-Time Monitoring Method of Hydrothermal Reactions. Thermochim. Acta 2001, 375, 9.
29. Shiraiwa, T.; Sakata, S.; Fujishima, K.; Kurokawa, H. Asymmetric Transformation of (R,S)-2-Phenylglycine via Formation of Salt with (1S)-10-Camphorsulfonic Acid. Bull. Chem. Soc. Jpn. 1991a, 64, 191.
30. Shiraiwa, T.; Shinjo, K.; Kurokawa, H. Asymmetric Transformation of Proline and 2-Piperidinecarboxylic Acid via Formation of Salts with Optically Active Tartaric Acid. Bull. Chem., Soc. Jpn. 1991b, 64, 3251.
31. Shiraiwa, T.; Shinjo, K.; Masui, Y.; Ohta, A.; Natsuyama, H.; Miyazaki, H.; Kurokawa, H. Facile Production of D-Histidine by Asymmetric Transformation of L-Histidine. Bull. Chem. Soc. Jpn. 1991c, 64, 3741.
32. Shiraiwa, T.; Sakata, S.; Fujishima, K.; Natsuyama, H.; Miyazaki, H.; Kubo, S.; Nitta, T.; Kurokawa, H. Racemization of Optically Active Aromatic N-Acetylamino Acids and Asymmetric Transformation of N-Acetyl-2-(4-hydroxyphenyl)glycine via Salt Formation with Optically Active (R)-Methylbenzylamine. Bull. Chem. Soc. Jpn. 1992, 65, 965.
33. Shiraiwa, T.; Baba, Y.; Miyazaki, H.; Sakata, S.; Kawamura, S.; Uehara, M.; Kurokawa, H. Optical Resolution and Asymmetric Transformation of (R,S)-N-Alkyl- and (R,S)-N,N-Dialkyl-2-phenylglycines. Bull. Chem. Soc. Jpn. 1993, 66, 1430.
34. Baum, R.; Smith, G. G. Systematic pH Study on the Acid-and Base-Catalyzed Racemization of Free Amino Acids to Determine the Six Constants, One for Each of the Three Ionic Species. J. Am. Chem. Soc. 1986, 108, 7325.
35. Toyokura, K.; Kurotani, M.; Fujinawa, J. Concentration Change of L-SCMC [(S)-(Carboxymethyl)-L-cysteine] in a Super-saturated Solution of DL-SCMC with Suspended L-SCMC Seeds in a Batch Operation. ACS Symp. Ser. 1997, 667, 46.
36. Matsuoka, M. Purity Drop in Optical Resolution of Racemic Mixtures. ACS Symp. Ser. 1997, 667, 59.
37. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: New York, 1989.
38. Yu, L.; Reutzel, S. M.; Stephenson, G. A. Physical Characterization of Polymorphic Drugs: an Integrated Characterization Strategy. Pharm. Sci. Technol. Today 1998, 1, 118.
39. Seddon, K. R. Crystal Engineering: A Case Study. In Crystal Engineering; NATO ASI Series C; Seddon, K. R., Zaworotko, M., Eds.; Kluwer Academic Publishers: Dordecht, The Netherlands, 1999; Vol. 539.
40. Nass, K. K. Process Implications of Polymorphism in Organic Compounds. AIChE Symp. Ser. 1991, 87 (284), 72.
41. Kawakita, T. Amino Acids, Glutamate. In The Encyclopedia of Bioprocess Technology: Fermentation, Biocatalysis, and Bioseparation; Flickinger, M. C., Drew, S. W., Eds.; Wiley: New York, 1999.
42. Kitamura, M.; Ueno, S.; Sato, K. Molecular Aspects of the Polymorphic Crystallization of Amino Acids and Lipids. In Crystallization Processes; Ohtaki, H., Ed.; Wiley: New York, 1998.
43. Yu, L.; Reutzel-Edens, S. M.; Mitchell, C. A. Crystallization and Polymorphism of Conformationally Flexible Molecules: Problems, Patterns, and Strategies. Org. Process Res. Dev. 2000b, 4, 396.
44. Beckmann, W.; Nickisch, K.; Budde, U. Development of a Seeding Technique for the Crystallization of the Metastable A Modification of Abecarnil. Org. Process Res. Dev. 1998, 2, 298.
45. Ibrahim, H. G.; Pisano, F.; Bruno, A. Polymorphism of Phenylbutazone: Properties and Compressional Behavior of Crystals. J. Pharm. Sci. 1977, 66, 669.
46. Cardew, P. T.; Davey, R. J. The Kinetics of Solvent-Mediated Phase Transformations. Proc. R. Soc. London 1985, A398, 415.
47. Sato, K.; Suzuki, K.; Okada, M. Solvent Effects on Kinetics of Solution-Mediated Transition of Stearic Acid Polymorphs. J. Cryst. Growth 1985, 72, 699.
48. Davey, R. J.; Richards, J. A Solvent Mediated Phase Transformation in an Aqueous Suspension of an Azo Dye. J. Cryst. Growth 1985, 71, 597.
49. Davey, R. J.; Cardew, P. T.; McEwan, D.; Sadler, D. E. Rate Controlling Processes in Solvent-Mediated Phase Transformations. J. Cryst. Growth 1986, 79, 648.
50. Maruyama, S.; Ooshima, H. Mechanism of the Solvent-Mediated Transformation of Taltirelin Polymorphs Promoted by Methanol. Chem. Eng. J. 2001, 81, 1.
51. Berry, D. A.; Dye, S. R.; Ng, K. M. Synthesis of Drowning-Out Crystallization-Based Separations. AIChE J. 1997, 43, 91.
52. Shi, Y.-J.; Wells, K. M.; Pye, P. J.; Choi, W.-B.; Churchill, H. R. O.; Lynch, J. E.; Maliakal, A.; Sager, J. W.; Rossen, K.; Volante, R. P.; Reider, P. J. Crystallization-Induced Asymmetric Transformation: Stereospecific Synthesis of L-768,673. Tetrahedron 1999, 55, 909.
53. Alabaster, R. J.; Gibson, A. W.; Johnson, S. A.; Edwards, J. S.; Cottrell, I. F. Synthesis of N-Benzyl-3-(S)-(+)-(4-fluorophenyl)-1,4-oxazin-2-one via a Crystallization Induced Asymmetric Transformation. Tetrahedron: Asymmetry 1997, 8, 447.
54. Czollner, L.; Frantsits, W.; Küenburg, B.; Hedenig, U.; Fröhlich, J.; Jordis, U. New Kilogram-Synthesis of the Anti-Alzheimer Drug (-)-Galanthamine. Tetrahedron Lett. 1998, 39, 2087.
55. Küenburg, B.; Czollner, L.; Fröhlich, J.; Jordis, U. Development of a Pilot Scale Process for the Anti-Alzheimer Drug (-)-Galanthamine Using Large-Scale Phenolic Oxidative Coupling and Crystallisation-Induced Chiral Conversion. Org. Process Res. Dev. 1999, 3, 425.
56. Lopez, F. J.; Ferriño, S. A.; Reyes, M. S.; Román, R. Asymmetric Transformation of the Second Kind of Racemic Naproxen. Tetrahedron: Asymmetry 1997, 8, 2497.
57. Calmes, M.; Escale, F. New Synthesis of Enantiomerically Pure (S)-3-Amino-2-phenyl Propanoic Acid via the Asymmetric Transformation of its Racemic N-Phthaloyl Derivative. Tetrahedron: Asymmetry 1998, 9, 2845.
58. Maryanoff, C. A.; Scott, L.; Shah, R. D.; Villani, F. J., Jr. A Crystallization-Induced Asymmetric Transformation to Prepare (R)-4-Chlorophenylalanine Methyl Ester. Tetrahedron: Asymmetry 1998, 9, 3247.
59. Bhattacharya A.; Araullomcadams, C.; Meier, M. B. Crystallization Induced Asymmetric Transformation Synthesis of D-p-Hydroxyphenylglycine. Synth. Commun. 1994, 24, 2449.
60. Hongo, C.; Yamada, S.; Chibata, I. Asymmetric Transformation of N-Acetyl-D,L-Leucine. Bull. Chem. Soc. Jpn. 1981, 54, 3291.
61. Vedejs, E.; Fields, S. C.; Schrimpf, M. R. Asymmetric Transformation in Synthesis: Chiral Amino Acid Enolate Equivalents. J. Am. Chem. Soc. 1993, 115, 11612.
62. Yu, L.; Stephenson, G. A.; Mitchell, C. S.; Bunnell, C. A.; Snorek, S. V.; Bowyer, J. J.; Borchardt, T. B.; Stowell, J. G.; Byrn, S. R. Thermochemistry and Conformational Polymorphism of a Hexamorphic Crystal System. J. Am. Chem. Soc. 2000a, 122, 585.
63. Wang, F.; Wachter, J. A.; Antosz, F. J.; Berglund, K. A. An Investigation of Solvent-Mediated Polymorphic Transformation of Progesterone Using in Situ Raman Spectroscopy. Org. Process Res. Dev. 2000, 4, 391.
64. McCauley, J. A. Detection and Characterization of Polymorphism in the Pharmaceutical Industry. AIChE Symp. Ser. 1991, 87 (284), 58.