Antisolvent crystallization of biapenem: Estimation of growth and nucleation kinetics

Journal of Chemical and Engineering Data

Volumn 58, Issue 3, 2013, Pages 588-597

  Luo, Yang Hui ^a   Wu, Guo Gan ^a   Sun, Bai Wang ^a  

^a SOUTHEAST UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-SOLVENT CRYSTALLIZATION; ATTENUATED TOTAL REFLECTION FOURIER TRANSFORM INFRARED; CHORD LENGTH DISTRIBUTION; CRYSTAL SIZE DISTRIBUTIONS; EXPERIMENTAL DATUM; FOCUSED BEAM REFLECTANCE MEASUREMENT; NUCLEATION KINETICS; SOLUTE CONCENTRATIONS;

ESTIMATION; EXPERIMENTS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; KINETICS; MATHEMATICAL MODELS; NUCLEATION;

GROWTH KINETICS;

EID: 84875140151     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je3011997     Document Type: Article

References (46)

1. Abu Bakar, M. R.; Nagy, Z. K.; Saleemi, A. N.; Rielly, C. D. The Impact of Direct Nucleation Control on Crystal Size Distribution in Pharmaceutical Crystallization Processes Cryst. Growth Des. 2009, 9 (3) 1378-1384
2. Luo, Y. H.; Zhang, C. G.; Xu, B.; Sun, B. W. A cocrystal strategy for the precipitation of liquid 2,3-dimethyl pyrazine with hydroxyl substituted benzoic acid and a Hirshfeld surfaces analysis of them CrystEngComm 2012, 14 (20) 6860-6868
3. Yu, L. X.; Lionberger, R. A.; Raw, A. S.; D'Costa, R.; Wu, H.; Hussain, A. S. Applications of process analytical technology to crystallization processes Adv. Drug Delivery Rev. 2004, 56, 349-369
4. Luo, Y. H.; Wu, G. G.; Mao, S. L.; Sun, B. W. Complexation of different metals with a novel N-donor bridging receptor and Hirshfeld surfaces analysis. Inorg. Chim. Acta 2012, http://dx.doi.org/10.1016/j.ica.2012.11.010.
5. Reutzel-Edens, S. M. Achieving polymorph selectivity in the crystallization of pharmaceutical solids: basic considerations and recent advances Drug Discovery Dev. 2006, 9, 806-815
6. Luo, Y. H.; Ma, Y. T.; Bao, Q. Q.; Sun, B. W. Syntheses, Crystal Structure and Properties of Two 1-D Coordination Polymers Bridged by Dicyanamides J. Chem. Crystallogr. 2012, 42, 628-632
7. Kitamura, M. Strategy for control of crystallization of polymorphs CrystEngComm 2009, 11, 949-964
8. Howard, K. S.; Nagy, Z. K.; Saha, B.; Robertson, A. L.; Steele, G.; Martin, D. A Process Analytical Technology Based Investigation of the Polymorphic Transformations during the Antisolvent Crystallization of Sodium Benzoate from IPA/Water Mixture Cryst. Growth Des. 2009, 9, 3964-3975
9. Nagy, Z. K.; Fujiwara, M.; Braatz, R. D. Modelling and control of combined cooling and antisolvent crystallization processes J. Process Control 2008, 18, 856-864
10. Nowee, S. M.; Abbas, A.; Romagnoli, A. Antisolvent crystallization: Model identification, experimental validation and dynamic simulation Chem. Eng. Sci. 2008, 63, 5457-5467
11. 13+ complex family J. Chem. Res. 2012, 36 (9) 505-508
12. O'Grady, D.; Barrett, M.; Casey, E.; Glennon, B. The Effect of Mixing on the Metastable Zone Width and Nucleation Kinetics in the Anti-Solvent Crystallization of Benzoic Acid Chem. Eng. Res. Des. 2007, 85, 945-952
13. Luo, Y. H.; Xu, J.; Sun, B. W. Synthesis, crystal structure and Hirshfeld surfaces of a CuII complex with an ICL670-related ligand J. Chem. Res. 2012, 697-700
14. Mullin, J. W. In Crystallisation, 4 th ed.; Butterworth Heinemann: Woburn, MA, 2001.
15. Schöll, J.; Lindenberg, C.; Vicum, L.; Brozio, J.; Mazzotti, M. Precipitation of α L-glutamic acid: determination of growth kinetics Faraday Discuss. 2007, 136, 247-264
16. Worlitschek, J.; Mazzotti, M. Model-Based Optimization of Particle Size Distribution in Batch-Cooling Crystallization of Paracetamol Cryst. Growth Des. 2004, 4, 891-903
17. Luo, Y. H.; Pan, M. L. 4-Nitroisophthalic acid Acta Crystallogr. 2012, E68, o206
18. Togkalidou, T.; Tung, H. H.; Sun, Y.; Andrews, A. T.; Braatz, R. D. Parameter Estimation and Optimization of a Loosely Bound Aggregating Pharmaceutical Crystallization Using in Situ Infrared and Laser Backscattering Measurements Ind. Eng. Chem. Res. 2004, 43, 6168-6181
19. Luo, Y. H.; Xu, J.; Pan, M. L.; Li, J. F. 2,4-Dibromo-6-[(hydroxyimino) methyl]-phenol Acta Crystallogr. 2011, E67, o2099
20. Miller, S. M.; Rawlings, J. B. Model identification and control strategies for batch cooling crystallizers AIChE J. 1994, 40, 1312-1327
21. Fujiwara, M.; Chow, P. S.; Ma, D. L.; Braatz, R. D. Paracetamol Crystallization Using Laser Backscattering and ATR-FTIR Spectroscopy: Metastability, Agglomeration, and Control Cryst. Growth Des. 2002, 2, 363-370
22. Feng, L. L.; Berglund, K. A. ATR-FTIR for Determining Optimal Cooling Curves for Batch Crystallization of Succinic Acid Cryst. Growth Des. 2002, 2, 449-452
23. Schöll, J. Ph.D. Thesis, ETH Zurich, 2006.
24. Luo, Y. H.; Tu, Y. R.; Ge; Sun, B. W. Monitoring the Crystallization Process of Methylprednisolone Hemisuccinate (MPHS) From Ethanol Solution by Combined ATR-FTIR-FBRM-PVM. Sep. Sci. Technol. 2013, accepted.
25. 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
26. Shaikh, A. A.; Salman, A. D.; Mcnamara, S.; Littlewood, G.; Ramsay, F.; Hounslow, M. J. In Situ Observation of the Conversion of Sodium Carbonate to Sodium Carbonate Monohydrate in Aqueous Suspension Ind. Eng. Chem. Res. 2005, 44 (26) 9921-9930
27. Garside, J.; Mersmann, A. Measurement of crystal growth and nucleation rates; Institution of Chemical Engineers: Rugby, U.K., 2002.
28. Schöll, J.; Lindenberg, C.; Vicum, L.; Mazzotti, M. Antisolvent Precipitation of PDI 747: Kinetics of Particle Formation and Growth Cryst. Growth Des. 2007, 7 (9) 1653-1661
29. Granberg, R. A.; Bloch, D. G.; Rasmuson, A. C. Crystallization of paracetamol in acetone-water mixtures J. Cryst. Growth 1999, 199, 1287-1293
30. Zhou, G. X.; Fujiwara, M.; Woo, X. Y.; Rusli, E.; Tung, H. H.; Starbuck, C.; Davidson, O.; Ge, Z.; Braatz, R. D. Direct Design of Pharmaceutical Antisolvent Crystallization through Concentration Control Cryst. Growth Des. 2006, 6 (4) 892
31. Kumagai, T.; Tamai, S.; Abe, T.; Matsunaga, H.; Hayashi, K.; Kishi, I.; Shiro, M.; Nagao, Y. New Straightforward Synthesis and Characterization of a Unique 1β-Methylcarbapenem Antibiotic Biapenem Bearing a σ-Symmetric Bicyclotriazoliumthio Group as the Pendant Moiety J. Org. Chem. 1998, 63, 8145-8149
32. Dunuwila, D. D.; Carroll, L. B.; Berglund, K. A. 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 1994, 137, 561-568
33. Ruf, A.; Worlitschek, J.; Mazzotti, M. Modeling and Experimental Analysis of PSD Measurements through FBRM Part. Part. Syst. Charact. 2000, 17, 167-179
34. Worlitschek, J.; Mazzotti, M. Choice of the Focal Point Position Using Lasentec FBRM Part. Part. Syst. Charact. 2003, 20, 12-17
35. Birch, M.; Fussell, S. J.; Higginson, P. D.; McDowall, N.; Marziano, I. Towards a PAT-Based Strategy for Crystallization Development Org. Process. Res. Dev. 2005, 9, 360-364
36. Lin, Z. H.; Zhou, L. L.; Mahajan, A.; Song, S.; Wang, T.; Ge, Z. H.; Ellison, D. Real-time endpoint monitoring and determination for a pharmaceutical salt formation process with in-line FT-IR spectroscopy J. Pharm. Biomed. Anal. 2006, 41, 99-104
37. Tadayyon, A.; Rohani, S. Determination of Particle Size Distribution by Par-Tec 100: Modeling and Experimental Results Part. Part. Syst. Charact. 1998, 15, 127-135
38. Hukkanen, E. J.; Braatz, R. D. Measurement of particle size distribution in suspension polymerization using in situ laser backscattering Sens. Actuators, B 2003, 96, 451-459
39. Li, M.; Wilkinson, D.; Patchigolla, K. Measuring Size Distribution of Organic Crystals of Different Shapes Using Different Technologies Part. Part. Syst. Charact. 2006, 23, 170-174
40. Borissova, A.; Dashova, Z.; Lai, X.; Roberts, K. J. Examination of the Semi-Batch Crystallization of Benzophenone from Saturated Methanol Solution via Aqueous Antisolvent Drowning-Out as Monitored In-Process Using ATR FTIR Spectroscopy Cryst. Growth Des. 2004, 4 (5) 1053-1060
41. Glade, H.; Ilyaskarov, A. M.; Ulrich, J. Determination of Crystal Growth Kinetics Using Ultrasonic Technique Chem. Eng. Technol. 2004, 27 (7) 736-740
42. Sohnel, O.; Mullin, J. W. Interpretation of crystallization induction periods J. Colloid Interface Sci. 1988, 123, 43-50
43. Hulburt, H. M.; Katz, S. Some problems in particle technology: A statistical mechanical formulation Chem. Eng. Sci. 1964, 19, 555-574
44. Randolph, A. D.; Larson, M. A. Theory of Particulate Processes, 2 nd ed.; Academic Press: San Diego, 1988.
45. Wynn, E. J. W. Relationship between particle-size and chord-length distributions in focused beam reflectance measurement: stability of direct inversion and weighting Powder Technol. 2003, 133, 125-133
46. Vaccaro, A.; Sefcik, J.; Morbidelli, M. Modeling focused beam reflectance measurement and its application to sizing of particles of variable shape Part. Part. Syst. Charact. 2007, 23, 360-373