Crystallisation of the orthorhombic form of acetaminophen: Combined effect of surface topography and chemistry

Powder Technology

Volumn 236, Issue , 2013, Pages 24-29

  Delmas, Thomas ^a   Shah, Umang V ^a   Roberts, Michael M ^a   Williams, Daryl R ^a   Heng, Jerry Y Y ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Acetaminophen; Colloidal templates; Crystallisation; Heterogeneous nucleation; Orthorhombic form

Indexed keywords

ACETAMINOPHEN; COLLOIDAL TEMPLATES; COMBINED EFFECT; FUNCTIONAL END GROUPS; HETEROGENEOUS NUCLEATION; MONOCLINIC CRYSTALS; ORGANIC MOLECULES; ORTHORHOMBIC FORMS; ORTHORHOMBIC POLYMORPH; RAPID COOLING METHOD; SILANISATION; SILICA NANOPARTICLES; SINGLE-STEP; SURFACE FUNCTIONAL;

CRYSTALLIZATION; SINGLE CRYSTAL SURFACES; SURFACE CHEMISTRY;

SURFACE TOPOGRAPHY;

AMINO GROUP; DODECYL GROUP; FUNCTIONAL GROUP; NANOPARTICLE; ORGANIC COMPOUND; PARACETAMOL; PHENYL GROUP; SILANE DERIVATIVE; SILICON DIOXIDE; TRIFLUOROPROPYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; COLLOID; COOLING; CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG STRUCTURE; ORGANIC CHEMISTRY; PHYSICAL CHEMISTRY; SALINITY; SURFACE PROPERTY;

EID: 84873703072     PISSN: 00325910     EISSN: 1873328X     Source Type: Journal    
DOI: 10.1016/j.powtec.2012.05.053     Document Type: Article

References (33)

1. Haisa M., Kashino S., Maeda H. The orthorhombic form of p-hydroxyacetanilide. Acta Crystallogr. B Struct. Sci. 1974, 30(10):2510-2512.
2. Perrin M.-A., Neumann M.A., Elmaleh H., Zaske L. Crystal structure determination of the elusive paracetamol form III. Chem. Commun. 2009, 22:3181-3183.
3. Di Martino P., Conflant P., Drache M., Huvenne J.P., Guyot-Hermann A.M. Preparation and physical characterization of forms II and III of paracetamol. J. Therm. Anal. Calorim. 1997, 48(3):447-458.
4. Di Martino P., Guyot-Hermann A.M., Conflant P., Drache M., Guyot J.C. A new pure paracetamol for direct compression: the orthorhombic form. Int. J. Pharm. 1996, 128(1-2):1-8.
5. Joiris E., Martino P.D., Berneron C., Guyot-Hermann A.-M., Guyot J.-C. Compression behavior of orthorhombic paracetamol. Pharm. Res. 1998, 15(7):1122-1130.
6. Nichols G., Frampton C.S. Physicochemical characterization of the orthorhombic polymorph of paracetamol crystallized from solution. J. Pharm. Sci. 1998, 87(6):684-693.
7. Mikhailenko M.A. Growth of large single crystals of the orthorombic paracetamol. J. Cryst. Growth 2004, 265:616-618.
8. Di Profio G., Tucci S., Curcio E., Drioli E. Controlling polymorphism with membrane-based crystallizers: Application to form I and II of paracetamol. Chem. Mater. 2007, 19(10):2386-2388.
9. Capes J.S., Cameron R.E. Contact line crystallization to obtain metastable polymorphs. Cryst. Growth Des. 2006, 7(1):108-112.
10. Thomas L.H., Wales C., Zhao L., Wilson C.C. Paracetamol form II: an elusive polymorph through facile multicomponent crystallization routes. Cryst. Growth Des. 2011, 11(5):1450-1452.
11. Lang M., Grzesiak A.L., Matzger A.J. The use of polymer heteronuclei for crystalline polymorph selection. J. Am. Chem. Soc. 2002, 124(50):14834-14835.
12. Price C.P., Grzesiak A.L., Matzger A.J. Crystalline polymorph selection and discovery with polymer heteronuclei. J. Am. Chem. Soc. 2005, 127(15):5512-5517.
13. Chadwick K., Myerson A., Trout B. Polymorphic control by heterogeneous nucleation - a new method for selecting crystalline substrates. CrystEngComm 2011, 13(22):6625-6627.
14. Stöber W., Fink A., Bohn E. Controlled growth of monodisperse silica spheres in the micron size range. J. Colloid Interface Sci. 1968, 26(1):62-69.
15. Delmas T., Roberts M.M., Heng J.Y.Y. Nucleation and crystallization of lysozyme: Role of substrate surface chemistry and topography. J. Adhes. Sci. Technol. 2011, 25:357-366.
16. Micheletto R., Fukuda H., Ohtsu M. A simple method for the production of a two-dimensional, ordered array of small latex particles. Langmuir 1995, 11(9):3333-3336.
17. Granberg R.A., Rasmuson Å.C. Solubility of paracetamol in pure solvents. J. Chem. Eng. Data 1999, 44(6):1391-1395.
18. Dushkin C.D., Lazarov G.S., Kotsev S.N., Yoshimura H., Nagayama K. Effect of growth conditions on the structure of two-dimensional latex crystals: Experiment. Colloid. Polym. Sci. 1999, 277(10):914-930.
19. Kuai S.-L., Hu X.-F., Haché A., Truong V.-V. High-quality colloidal photonic crystals obtained by optimizing growth parameters in a vertical deposition technique. J. Cryst. Growth 2004, 267(1-2):317-324.
20. 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(5):363-370.
21. Kim K.-J., Mersmann A. Estimation of metastable zone width in different nucleation processes. Chem. Eng. Sci. 2001, 56(7):2315-2324.
22. Di Profio G., Tucci S., Curcio E., Drioli E. Selective glycine polymorph crystallization by using microporous membranes. Cryst. Growth Des. 2007, 7(3):526-530.
23. He G., Bhamidi V., Tan R.B.H., Kenis P.J.A., Zukoski C.F. Determination of critical supersaturation from microdroplet evaporation experiments. Cryst. Growth Des. 2006, 6(5):1175-1180.
24. Cardew P.T., Davey R.J. The kinetics of solvent-mediated phase transformations. Proc. R. Soc. Lond. Ser. A 1985, 398(1815):415-428.
25. Ha J.-M., Hamilton B.D., Hillmyer M.A., Ward M.D. Phase behavior and polymorphism of organic crystals confined within nanoscale chambers. Cryst. Growth Des. 2009, 9(11):4766-4777.
26. Ha J.-M., Wolff J.H., Hillmyer M.A., Ward M.D. Polymorph selectivity under nanoscopic confinement. J. Am. Chem. Soc. 2004, 126(11):3382-3383.
27. Hamilton B.D., Hillmyer M.A., Ward M.D. Glycine polymorphism in nanoscale crystallization chambers. Cryst. Growth Des. 2008, 8(9):3368-3375.
28. Shah U.V., Williams D.R., Heng J.Y.Y. Selective crystallization of proteins using engineered nanonucleants. Cryst. Growth Des. 2012, 12(3):1362-1369.
29. Beiner M., Rengarajan, Pankaj S., Enke D., Steinhart M. Manipulating the crystalline state of pharmaceuticals by nanoconfinement. Nano Lett. 2007, 7(5):1381-1385.
30. Mullin J.W. Crystallization 2001, Elsevier Butterworth-Heinemann, Oxford.
31. Söhnel O., Mullin J.W. Interpretation of crystallization induction periods. J. Colloid Interface Sci. 1988, 123(1):43-50.
32. Tosi G., Fermani S., Falini G., Gavira J.A., Garcia Ruiz J.M. Hetero- vs homogeneous nucleation of protein crystals discriminated by supersaturation. Cryst. Growth Des. 2011, 11(5):1542-1548.
33. Shah U.V., Allenby M.C., Williams D.R., Heng J.Y.Y. Crystallization of proteins at ultralow supersaturations using novel three-dimensional nanotemplates. Cryst. Growth Des. 2012, 12(4):1772-1777.