Modeling crystal shapes of organic materials grown from solution

AIChE Journal

Volumn 46, Issue 7, 2000, Pages 1348-1367

  Winn, Daniel ^a   Doherty, Michael F ^a  

^a University of Massachusetts at Amherst   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; CRYSTALLIZATION; MATHEMATICAL MODELS; MORPHOLOGY; SOLUTIONS;

CRYSTAL SHAPE; CRYSTALLINE ORGANIC SOLID; IMPURITY EFFECTS;

ORGANIC COMPOUNDS;

ADIPIC ACID; HEXANE; IBUPROFEN; METHANOL; ORGANIC COMPOUND; SOLVENT; WATER;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; KINETICS; MODEL; PREDICTION;

EID: 0034233568     PISSN: 00011541     EISSN: None     Source Type: Journal    
DOI: 10.1002/aic.690460709     Document Type: Article

References (99)

1. Bennema, P., and G. H. Gilmer, "Kinetics of Crystal Growth," Crystal Growth: An Introduction, P. Harman, ed., North-Holland, Amsterdam (1973).
2. Bennema, P., "On the Crystallographic and Statistical Mechanical Foundations of the Forty-Year Old Hartman-Perdok Theory," J. Crystal Growth, 166, 17 (1996).
3. Boek, E. S., W. J. Briels, and D. Feil, "Interfaces between a Saturated Aqueous Urea Solution and Crystalline Urea: A Molecular Dynamics Study," J. Phys. Chem., 98, 1674 (1994).
4. Berkovitch-Yellin, Z., "Toward an ab Initio Derivation of Crystal Morphology," J. Am. Chem. Soc., 107, 8239 (1985).
5. Berkovitch-Yellin, Z., J. van Mil, L. Addadi, M. Idelson, M. Lahav and L. Leiserowitz, "Crystal Morphology Engineering by Taylor-Made Inhibitors: A New Probe to Fine Intermolecular Interactions," J. Am. Chem. Soc., 107, 3111 (1985).
6. Bermingham, S. K., A. M. Neumann, H. J. M. Kramer, P. J. T. Verheijen, G. M. van Rosmalen, and J. Grievink, "A Design Procedure and Predictive Models for Solution Crystallization Processes," Fifth Int. Conf. on Foundations of Computer-Aided Process Design, Breckenridge, CO. M. F. Malone and J. A. Trainham, eds., AIChE, New York (2000).
7. Bravais, A., Etudes Crystallographiques, Gauthier-Villars, Paris (1866).
8. Bunyan, J. M. E., N. Shankland, and D. B. Sheen, "Solvent Effects on the Morphology of Ibuprofen," Particle Design Via Crystallization, Ramanarayanan, R. W. Kern, M. Larson, and S. Sikdar, eds., AIChE, New York (1991).
9. Burton, W. K., N. Cabrera, and F. C. Frank, "The Growth of Crystals and the Equilibrium Structure of their Surfaces," Phil. Trans. Roy Soc., A243, 299 (1951).
10. Cabrera, N., and M. Levine, "On the Dislocation Theory of Evaporation of Crystals," Phil. Mag., 1, 450 (1956).
11. Cahn, J. W., J. E. Taylor, and C. A. Handwerker, "Evolving Crystal Forms: Frank's Characteristics Revisited," Sir Charles Frank, OBE, FRS, An Eightieth Birthday Tribute, R. G. Chambers, J. E. Enderby, and A. Keller, eds., Hilger, New York (1991).
12. Chan, H., and D. J. W. Grant, "Influence of Compaction on the Intrinsic Dissolution Rate of Modified Acetaminophen and Adipic Acid Crystals," Int. J. Pharm., 57, 117 (1989).
13. Chernov, A. A., "The Kinetics of the Growth Forms of Crystals," Sov. Phys. Cryst., 7, 728 (1963).
14. Chernov, A. A., Modern Crystallography III, Springer-Verlag, New York (1984).
15. Clydesdale, G., R. Docherty, and K. J. Roberts, "HABIT - A Program for Predicting the Morphology of Molecular Crystals," Comp. Phys. Comm., 64, 311 (1991).
16. Clydesdale, G., K. J. Roberts and R. Docherty, "Modeling the Morphology of Molecular Crystals in the Presence of Disruptive Tailor-Made Additives," J. Crystal Growth, 135, 331 (1994).
17. Curry, J. E., and J. H. Cushman, "Nanophase Coexitence and Sieving in Binary Mixures Confined Between Corrugated Walls," J. Chem. Phys., 103, 2132 (1995).
18. Davey, R., W. Fila, and J. Garside, "The Influence of Biuret on the Growth Kinetics of Urea Crystal from Aqueous Solutions," J. Crystal Growth, 79, 607 (1986).
19. Davey, R. J., S. N. Black, D. Logan, S. J. Maginn, J. E. Fairbrother and D. J. W. Grant, "Structural and Kinetic Features of Crystal Growth Inhibition: Adipic Acid Growing in the Presence of n-Alkanoic Acids," J. Chem. Soc. Faraday Trans., 88, 3461 (1992).
20. Davey, R. J., "Looking Into Crystal Chemistry," The Chemical Engineer, (Dec. 1991).
21. Docherty, R., and K. J. Roberts, "Morang - A Computer Program Designed to Aid in the Determination of Crystal Morphology," Comp. Phys. Comm., 51, 423 (1988a).
22. Docherty, R., and K. J. Roberts, "Modelling the Morphology of Molecular Crystals; Application to Anthracene, Biphenyl and β-Succinic Acid," J. Crystal Growth, 88, 159 (1988b).
23. Docherty, R., K. J. Roberts, V. Saunders, S. Black, and R. J. Davey, "Theoretical Analysis of the Polar Morphology and Absolute Polarity of Crystalline Urea," Faraday Discuss., 95, 11 (1993).
24. Donnay, J. D. H., and D. Harker, "A New Law of Crystal Morphology Extending the Law of Bravais," Amer. Min., 22, 446 (1937).
25. Frank, F. C., "On the Kinematic Theory of Crystal Growth and Dissolution Processes," Growth and Perfection of Crystals, R. H. Doremus, B. W. Roberts, and D. Turnbull, eds., Wiley, New York (1958).
26. Frank, F. C., "On the Kinematic Theory of Crystal Growth and Dissolution Processes, II," Z. Phys. Chem., 77, 84 (1972).
27. Friedel, M. G., "Etudes Sur la loi de Bravais," Bull. Soc. Franc. Miner., 9, 326 (1907).
28. Gavezzotti, A., G. Filippini, J. Kroon, B. P. van Eijck, and P. Klewinghaus, "The Crystal Polymorphism of Tetrolic Acid: A Molecular Dynamics Study of Precursors in Solution, and Crystal Structure Generation," Chem. Eur. J., 3, 893 (1997).
29. Geertman, R. M., and A. E. D. M. van der Heijden, "On the Morphology of Caprolactam," J. Crystal Growth, 125, 363 (1992).
30. Gibbs, J. W., The Collected Works of J. Willard Gibbs, Yale University Press, New Haven (1928).
31. Gilli, G., "Molecules and Molecular Crystals," Fundamentals of Crystallography, C. Giacovazzo, ed., Oxford University Press, Oxford (1992).
32. Gilmer, G. H., and P. Bennema, "Simulation of Crystal Growth with Surface Diffusion," J. Appl. Phys., 43, 1347 (1972).
33. Girifalco, L. A., and R. J. Good, "A Theory for the Estimation of Surface and Interfacial Energies: I. Derivation and Application to Interfacial Tension," J. Phys. Chem., 61, 904 (1957).
34. Glasstone, S., K. J. Laidler, and H. Eyring, The Theory of Rate Processes, McGraw-Hill, New York (1941).
35. Gordon, R. E., and S. I. Amin, "Crystallization of Ibuprofen," U.S. Patent Number 4,476,248 (1984).
36. Grant, D. J. W., K. Y. Chow, and H. Chan, "Modification of the Physical Properties of Adipic Acid by Crystallization in the Presence of n-Alkanoic Acids," Particle Design Via Crystallization, Ramanarayanan, R. W. Kern, M. Larson, and S. Sikdar, eds., AICHE, New York (1991).
37. Grimbergen, R. F. P., and P. Bennema, "An Automated Method for PBC Analyses Applied to Benzoic Acid: A Comparison Between the Monomer and Dimer Analysis," Crystal Growth of Organic Materials, A. S. Myerson, D. A. Green, and P. Meenan, eds., ACS, Washington (1996).
38. Hagler, A. T., E. Huler, and S. Lifson, "Energy Functions for Peptides and Proteins. I.," J. Am. Chem. Soc., 96, 5319 (1974).
39. Hahn, T., International Tables for Crystallography, 4th ed., Dordrecht, Boston (1995).
40. Hartman, P., "Relations between Structure and Morphology of Crystals," PhD Diss., University of Groningen, The Netherlands (1953).
41. Hartman, P., and W. G. Perdok, "On the Relations Between Structure and Morphology of Crystals. I," Acta. Cryst., bf 8, 49 (1955).
42. Hartman, P., "Crystal Form and Crystal Structure," Physics and Chemistry of the Organic Solid State, D. Fox, M. M. Labes, and A. Weissberger, eds., Wiley, New York (1963).
43. Herring, C., "Some Theorems on the Free Energies of Crystal Surfaces," Phys. Rev., 82, 87 (1951).
44. Herring, C., "The Use of Classical Macroscopic Concepts in Surface Energy Problems," Structure and Properties of Solid Surfaces, R. Gomer and C. S. Smith, eds., University of Chicago Press, Chicago (1953).
45. Hoffman, D. W., and J. W. Cahn, "A Vector Thermodynamics for Anisotropic Surfaces," Surf. Sci., 31, 389 (1972).
46. Housty, J., and M. Hospital, "Localisation des Atomes d'Hydrogène dans l'Acide Adipique," Acta Cryst., 18, 693 (1965).
47. Jackson, K. A., "Mechanism of Growth," Liquid Metals and Solidification, American Society for Metals, Cleveland (1958).
48. Jetten, L. A. M. J., H. J. Hunan, P. Bennema, and J. P. van der Eerden, "On the Observation of the Roughening Transition of Organic Crystals Growing from Solution," J. Crystal Growth, 68, 503 (1984).
49. John, F., Partial Differential Equations, 2nd ed., Springer, New York (1975).
50. Kaelble, D. H., Physical Chemistry of Adhesion, Wiley-Interscience, New York (1971).
51. Kaichew, R., and I. N. Stranski, "Zur Theorie der linearen Kristallisationsgeschwindigkeit," Z. Phys. Chem., A170, 295 (1934).
52. Karger, B. L., L. R. Snyder, and C. Eon, "An Expanded Solubility Parameter Treatment for Classification and Use of Chromatographic Solvents and Adsorbents," J. Chromatography, 125 89 (1976).
53. Kitaigorodsky, A. I., K. V. Mirskaya, and A. B. Tovbis, "Lattice Energy of Crystalline Benzene in the Atom-Atom Approximation," Sov. Phys. Cryst., bf 13, 176 (1968).
54. Kitaigorodsky, A. I., Molecular Crystals and Molecules, Academic Press, New York (1973).
55. Klug, D. L., and J. H. van Mil, "Adipic Acid Purification," United States Patent Number 5,296,639 (1994).
56. Koolman, H. C., and R. W. Rousseau, "Effects of Isomorphic Compounds on the Purity and Morphology of L-Isoleucine Crystals," AIChE J., 42, 147 (1996).
57. Lahav, M., and L. Leiserowitz, "Tailor-Made Auxiliaries for the Control of Nucleation, Growth and Dissolution of Two- and Three-Dimensional Crystals," J. Phys. D, 26, B22 (1993).
58. Land, T. A., A. J. Malkin, Yu. G. Kutzensov, A. McPherson, and J. J. DeYoreo, "Mechanism of Protein and Virus Crystal Growth: An Atomic Force Microscopy Study of Canavalin and STMV Crystallization," J. Crystal Growth, 166, 893 (1996).
59. Lewis, B., "The Growth of Crystals of Low Supersaturation, II. Comparison with Experiment," J. Crystal Growth, 21, 40 (1974).
60. Lifson, S., A. T. Habler, and P. Dauber, "Consistent Force Field Studies of Intermolecular Forces in Hydrogen-Bonded Crystals. 1.," J. Am. Chem. Soc., bf 101, 5111 (1979).
61. Liu, X. Y., and P. Bennema, "Self-Consistent Field Calculation of Structures and Static Properties of the Solid-Fluid Interface; Paraffinlike Molecule Systems," Phys. Rev. E, 48, 2006 (1993a).
62. Liu, X. Y., and P. Bennema, "The Relationship Between Macroscopic Quantities and the Solid-Fluid Interfacial Structure," J. Chem. Phys., 98, 5863 (1993b).
63. Liu, X. Y., and P. Bennema, "Morphology of Crystal: Internal and External Habit Controlling Factors," Phys. Rev. B, 49, 765 (1994).
64. Liu, X. Y., E. S. Boek, W. J. Briels, and P. Bennema, "Prediction of Crystal Growth Morphology Based on Structural Analysis of the Solid-Fluid Interface," Nature, 374, 342 (1995).
65. Liu, X. Y., and P. Bennema, "Theoretical Consideration of the Growth Morphology of Crystals," Phys. Rev. B, 53, 2314 (1996a).
66. Liu, X. Y., and P. Bennema, "An Inhomogeneous Cell Model and the Growth of Crystals," J. Crystal Growth, 166, 112 (1996b).
67. Liu, X. Y., and P. Bennema, "Growth Morphology of Crystals and the Influence of Fluid Phase," Crystal Growth of Organic Materials, A. S. Myerson, D. A. Green, and P. Meenan, eds., ACS, Washington (1996c).
68. Manne, S., J. P. Cleveland, G. D. Stucky, and P. K. Hansma, "Lattice Resolution and Solution Kinetics and Surfaces of Amino Acid Crystals: An Atomic Force Microscopy Study," J. Crystal Growth, 130, 133 (1993).
69. Mason, R., "The Crystallography of Anthracene 95°K and 290°K," Acta Cryst., 17, 547 (1964).
70. Markov, I. V., Crystal Growth for Beginners, World Scientific, Singapore (1995).
71. Mayo, S. L., B. D. Olafson, and W. A. Goddard, III, "DREIDING: A Generic Force Field for Molecular Simulations," J. Phys. Chem., 94, 8897 (1990).
72. McConnell, J. F., "2-(4-Isobutylpheny) Propionic Acid,"Cryst. Struct. Comm., 3, 73 (1974).
73. Michaels, A. S., and A. R. Colville, Jr., "The Effect of Surface Active Agents on Crystal Growth Rate and Crystal Habit," J. Phys. Chem., 64, 13 (1960).
74. Momany, F. A., L. M. Curuthers, R. F. McGuire, and H. A. Scheraga, "Intermolecular Potentials from Crystal Data," J. Phys. Chem., 78, 1595 (1974).
75. Myerson, A. S., and M. Saska, "Calculation of Crystal Habit and Solvent-Accessible Areas of Sucrose and Adipic Acid Crystals," Crystallization as a Separations Process, A. S. Myerson and K. Toyokura, eds., ACS, Washington (1990).
76. Myerson, A. S., and R. Ginde, "Crystals, Crystal Growth, and Nucleation," Handbook of Crystal Growth, A. S. Myerson, ed., Butterworth-Heinemann, Boston (1993).
77. Ohara, M., and R. C. Reid, Modeling Crystal Growth Rates from Solution, Prentice-Hall, Englewood Cliffs, NJ (1973).
78. Pfefer, G., and R. Boistelle, "Control of Molecular Crystal Morphology," Trans. IChemE., 74, 744 (1996).
79. Reynolds, G. F., "Crystal Growth," Physics and Chemistry of the Organic Solid State, D. Fox, M. M. Labes, and A. Weissberger, eds., Wiley, New York (1963).
80. Romero, A. J., G. Lucas, and C. T. Rhodes, "Influence of Different Sources on the Processing and Biopharamaceutical Properties of High-dose Ibuprofen Formulations," Pharm. Acta Helv., 66, 34 (1991).
81. Sandler, S. I., Chemical and Engineering Thermodynamics, 2nd ed., Wiley, New York (1989).
82. Saska, M., and A. S. Myerson, "The Theoretical Shape of Sucrose Crystals from Solution," J. Crystal Growth, 61, 546 (1983).
83. Schwinn, T., H. E. Gaub, and J. P. Rabe, "Supramolecular Structures and Dynamics of Organic Adsorbate Layers at the Solid-Liquid Interface," Supramolecul Sci., 1, 85 (1994).
84. Storey, R. A., "The Nucleation, Growth and Solid-State Properties of Particulate Pharmaceuticals," Ph.D. Thesis, University of Bradford, U.K. (1997).
85. Swendson, R. H., P. J. Kortman, D. P. Landau, and H. Muller-Krumbhaar, "Spiral Growth of Crystals: Simulation on a Stochastic Model," J. Crystal Growth, 35, 73 (1976).
86. Tanguy, D., and P. Marchal, "Relations between the Properties of Particles and their Process of Manufacture," Trans IChemE, 74, 715 (1996).
87. Tavare, N. S., Industrial Crystallization, Plenum, New York (1994).
88. Taylor, J. E., "Crystalline Variational Problems," Bull. Am. Math. Soc., 84, 568 (1978).
89. Taylor, J. E., J. W. Cahn, and C. A. Handwerker, "I - Geometric Models of Crystal Growth," Acta. Metall. Mater., 40, 1443 (1992).
90. Volmer, M., and M. Marder, "Zur Theorie der linearen Kristallisations-geschwindigkeit unterkuhlter Schemlzen und unterkuhlter fester Modifikationen," Z. Phys. Chem., A154, 97 (1931).
91. Walker, E., and K. J. Roberts, Molecular Simulations Application Notes, CGR 10, Biosym/Molecular Simulations Inc. (1993).
92. Wells, A. F., "Crystal Habit and Internal Structures - I," Phil. Mag., 37, 184 (1946).
93. Wells, A. F., "Crystal Growth and Chemical Structure," Structure and Properties of Solid Surfaces, R. Gomer and C. S. Smith, eds., University of Chicago Press, Chicago (1953).
94. Williams, D. E., "Nonbonded Potential Parameters Derived from Crystalline Aromatic Hydrocarbons," J. Chem. Phys., 45, 3770 (1966).
95. Winn, D., and M. F. Doherty, "A New Technique for Predicting the Shape of Solution-Grown Organic Crystals," AIChE J., 44, 2501 (1998).
96. Winn, D., and M. F. Doherty, "Predicting the Shape of Organic Crystals Grown from Polar Solvents," Proc. of the 14th Int. Symp. on Ind. Crystallization, Institution of Chemical Engineers, London, U.K. (1999).
97. Wulff, G., "Zur Frage der Geschwindigkeit des Wachsthums und der Auflösung der Krystallflächen," Z. Kryst., 34, 449 (1901).
98. Yip, C. M., and M. D. Ward, "Atomic Force Microscopy of Insulin Single Crystal: Direct Visualization of Molecules and Crystal Growth," Biophys. J., 71, 1071 (1996).
99. York, P., "Solid-State Properties of Powders in the Formulation and Processing of Solid Dose Forms," Int. J. Pharm., 14, 1071 (1983).