Skip to main content
SpringerLink
Log in

Effect of High Pressure on the Polymorphs of Paracetamol

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript

Abstract

Effect of hydrostatic pressure on the two (I – monoclinic and II – orthorhombic) polymorphs of paracetamol was studied by X-ray diffraction in the diamond anvil cell at pressures up to 4.5 GPa (for the monoclinic form) and up to 5.5 GPa (for the orthorhombic form). The two groups of phenomena were studied: (i) the anisotropic structural distortion of the same polymorph, (ii) transitions between the polymorphs induced by pressure.

The anisotropy of structural distortion of polymorphs I and II was well reproducible from sample to sample, also from powder samples to single crystals. The bulk compressibility of the two forms was shown to be practically the same. However, a noticeable qualitative difference in the anisotropy of structural distortion was observed: with increasing pressure the structure of polymorph II contracted in all the directions showing isotropic compression in the planes of hydrogen-bonded molecular layers, whereas the layers in the structure of the polymorph I expanded in some directions. Maximum compression in both polymorphs I and II was observed in the directions normal to the molecular layers.

The transitions between the polymorphs induced by pressure were poorly reproducible and depended strongly on the sample and on the procedure of increasing/decreasing pressure. No phase transitions were induced in the single crystals of the monoclinic polymorph at pressures at least up to 4GPa, although a partial transformation of polymorph I into polymorph II was observed at increased pressure in powder samples. Polymorph II transformed partly into the polymorph I during grinding. The transformation could be hindered if grinding was carried out in CCl4.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. http://www.pharmweb.net/pwmirror/pwy/paracetamol

  2. J. von Mering, Therap. Monatschefte, 7 (1893) 577.

    Google Scholar 

  3. Merck Index, 9th ed. Rathway, N. Y. 1976.

  4. J. E. Fairbrother (1974) In: K. Florey (Ed.) Analytical Profiles of Drug Substances, vol. 3. Academic Press, N. Y., p. 1.

    Google Scholar 

  5. S. R. Byrn, Solid State Chemistry of Drugs, Academic Press, N. Y. 1982.

    Google Scholar 

  6. J. Bernstein, in: Computer-Assisted Modeling of Receptor-Ligand Interactions. Theoretical Aspects and Applications to Drug Design, A. Golombek, ed. Alan R. Liss, New York 1989, p. 203.

    Google Scholar 

  7. T. P. Shakhtshneider and V. V. Boldyrev, In: E. V. Boldyreva, V. V. Boldyrev (Eds) Reactivity of Molecular Solids, Molecular Solid State Series, vol 3. Wiley, 1999, Chichester, p. 271.

    Google Scholar 

  8. G. Winter, In: E. V. Boldyreva, V. V. Boldyrev (Eds), Reactivity of Molecular Solids, Molecular Solid State, vol 3. Wiley, 1999, Chichester, p. 241.

    Google Scholar 

  9. E. Marti, E. Kaisersberger, G. Kaiser (Eds), Thermoanalytical Characterization of Pharmaceuticals, Netzsch Annual 2000, Netzsch-Geraetebau GmbH, 12 (2000), Selb, p. 29.

  10. M. Haisa, S. Kashino, R. Kawai and H. Maeda, Acta Cryst., B32 (1976) 1283.

    CAS  Google Scholar 

  11. Y. T. Sohn, J. Korean Pharm. Sci., 20 (1990) 97.

    CAS  Google Scholar 

  12. B. S. Nath and S. S. Khali, Indian J. Pharm. Sci., 46 (1984) 106.

    CAS  Google Scholar 

  13. G. Nichols and C. S. Frampton, J. Pharm. Sci., 87 (1998) 684.

    Article  CAS  Google Scholar 

  14. D. Y. Naumov, M. A. Vasilchenko and J. A. K. Howard, Acta Cryst., C54 (1998) 653.

    CAS  Google Scholar 

  15. M. Haisa, S. Kashino and H. Maeda, Acta Cryst., B30 (1974) 2510.

    Google Scholar 

  16. J. D. Dunitz and J. Bernstein, Acc. Chem. Res., 28 (1995) 193.

    Article  CAS  Google Scholar 

  17. T. P. Shakhtshneider, V. V. Boldyrev, D. Y. Naumov and M. A. Vasilchenko, J. Pharm. Sci., 85 (1996) 929.

    Article  Google Scholar 

  18. V. V. Boldyrev, M. A. Vasilchenko, T. P. Shakhtshneider, D. Y. Naumov and E. V. Boldyreva, Solid State Ionics, 101-103 (1997) 869.

    Article  CAS  Google Scholar 

  19. M. A. Vasilchenko, T. P. Shakhtshneider, D. Y. Naumov and V. V. Boldyrev, J. Therm. Anal. Cal., 57 (1999) 157.

    Article  CAS  Google Scholar 

  20. P. DiMartino, A.-M. Guyot-Hermann, P. Conflant, M. Drache and J.-C. Guyot, Int. J. Pharm., 128 (1996) 1.

    Article  Google Scholar 

  21. E. von Nuernberg and A. Hopp, Pharm. Ind., 44 (1982) 1081.

    Google Scholar 

  22. F. N. deWet, J. J. Gerber, A. P. Loetter, J. G. van der Watt and T. G. Dekker, Drug Dev. Ind. Pharm., 24 (1998) 447.

    Article  CAS  Google Scholar 

  23. M. Kuhnert-Brandstaetter, Thermomicroscopy in the Analysis of Pharmaceuticals, Pergamon Press, Oxford 1971.

    Google Scholar 

  24. A. Burger, Acta Pharm. Technol., 28 (1982) 1.

    CAS  Google Scholar 

  25. P. Conflant and A.-M. Guyot-Hermann, Eur. J. Pharm. Biopharm., 40 (1994) 388.

    CAS  Google Scholar 

  26. J. Barra, F. Kubel and E. Doelker, Book of Abstracts, 3rd Symposium on Pharmacy and Thermal Analysis, 1997, Ascona, Switzerland, 2PO.

  27. P. DiMartino, P. Conflant, M. Drache, J.-P. Huvenne and A.-M. Guyot-Hermann, J. Thermal Anal., 48 (1997) 447.

    Article  CAS  Google Scholar 

  28. S. Cianferani, A. P. Hard, U. C. Hofmeier, C. Marcolli, M. Szelagiewicz and A. Zilian, Book of Abstracts, PhandTA-4, Karlsruhe, Germany 1999.

  29. S. Cianferani, M. Szelagiewicz, S. Walter and E. Marti, Proceed. 23rd Annual Calorimetrie et d’Analyse Thermique (AFCAT), Bale Meeting, Switzerland 1998.

  30. M. Szelagiewicz, C. Marcolli, S. Cianferani, A. P. Hard, A. Vit, A. Burkhard, M. von Raumer, U. C. Hofmeier, A. Zilian, E. Francotte and R. Schenker, J. Therm. Anal. Cal., 57 (1999) 23.

    Article  CAS  Google Scholar 

  31. J.-M. Fachaux, A.-M. Guyot-Hermann, J.-C. Guyot, P. Conflant, M. Drache, S. Veesler and R. Boistelle, Powder Techn., 82 (1995) 123.

    Article  CAS  Google Scholar 

  32. J.-M. Fachaux, A.-M. Guyot-Hermann, J.-C. Guyot, P. Conflant, M. Drache, S. Veesler and R. Boistelle, Powder Techn., 82 (1995) 129.

    Article  CAS  Google Scholar 

  33. E. V. Boldyreva and V. V. Boldyrev, Eds. Reactivity of Molecular Solids, Molecular Solid State Series, Vol. 3, Wiley, Chichester 1999.

    Google Scholar 

  34. T. P. Shakhtshneider, E. V. Boldyreva, M. A. Vasilchenko, H. Ahsbahs and H. Uchtmann, Dokl. RAN, 363 (1998) 783.

    CAS  Google Scholar 

  35. T. P. Shakhtshneider, E. V. Boldyreva, M. A. Vasilchenko, H. Ahsbahs and H. Uchtmann, Russ. J. Struct. Chem., 40 (1999) 1101.

    Article  Google Scholar 

  36. E. V. Boldyreva, T. P. Shakhtshneider, M. A. Vasilchenko, H. Ahsbahs and H. Uchtmann, Acta Cryst., B56 (2000) 299.

    CAS  Google Scholar 

  37. C. E. Weir, S. Block and G. J. Piermarini, J. Res. Nat. Bur. Stand., 69C (1965) 275.

    Google Scholar 

  38. R. A. Forman, G. J. Piermarini and J. D. Barnett, S. Block, Science, 176 (1972) 284.

    Google Scholar 

  39. G. J. Piermarini, S. Block, J. D. Barnett and R. A. Forman, J. Appl. Phys., 46 (1975) 2774.

    Article  CAS  Google Scholar 

  40. R. Brueggemann, B. Mueller, T. Debaerdemaeker, G. Schmid and U. Thewalt, Computing program complex ULM for X-ray crystallography, University of Ulm, Germany 1992.

    Google Scholar 

  41. R. Hazen and L. Finger, Comparative Crystal Chemistry. Temperature, Pressure, Composition and Variation of the Crystal Structure, Wiley, N. Y. 1982.

    Google Scholar 

  42. W. Kraus and G. Nolze, PowderCell for Windows, Vers. 2.3, http://www.bam.de/a_v/v_1/powder/e_cell.html.

  43. T. Beyer and S. L. Price, Book of Abstracts, of the 19th European Crystallographic Meeting (ECM-19), Nancy, France, 2000, o.m6.o5, p. 160.

  44. I. G. Binev, P. Vassileva-Boyadjieva and Y. I. Binev, J. Mol. Struct., 447 (1998) 235.

    Article  CAS  Google Scholar 

  45. A. A. Politov, V. G. Kostrovsky and V. V. Boldyrev, Russ. J. Phys. Chem., 75 (2001) 2065.

    Google Scholar 

  46. P. W. Bridgman, Recent work in the field of high pressures, Rev. Modern Phys., 18 (1946) 1.

    Article  CAS  Google Scholar 

  47. A. Katrusiak, Acta Cryst., B51 (1995) 873.

    CAS  Google Scholar 

  48. E. V. Boldyreva, H. Ahsbahs, N. E. Kashcheeva and H. Uchtmann, High Press. Res., 17 (2000) 79.

    Google Scholar 

  49. E. V. Boldyreva, In: E. V. Boldyreva, V. V. Boldyrev (Eds), Reactivity of Molecular Solids, Molecular Solid State, Vol. 3, Wiley, Oxford 1999, p. 1.

    Google Scholar 

  50. A. V. Dzyabchenko, E. V. Boldyreva, Book of Abstracts, of the 19th European Crystallographic Meeting (ECM-19), Nancy, France 2000, s6.m2.p2, p. 215.

  51. E. B. Burgina, V. P. Baltakhinov, E. V. Boldyreva, T. P. Shakhtshneider, H. Ahsbahs and H. Uchtmann, unpublished results.

Download references

Author information

Authors and Affiliations

  1. Institute of Solid State Chemistry, Siberian Department of Russian Academy of Sciences, Kutateladze, 18, Novosibirsk, 630128, Russia

    E. V. Boldyreva & T. P. Shakhtshneider

  2. Center of Advanced Education ‘Molecular Design and Ecologically Advanced Technologies’, Novosibirsk State University, Pirogova, 2, Novosibirsk, 630090, Russia

    E. V. Boldyreva & T. P. Shakhtshneider

  3. Center of Materials Sciences, Philips-Universität Marburg/Lahn, Hans-Meerwein Strasse, Marburg/Lahn, Germany

    H. Ahsbahs, H. Sowa & H. Uchtmann

Authors
  1. E. V. Boldyreva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. P. Shakhtshneider
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. H. Ahsbahs
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. H. Sowa
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. H. Uchtmann
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Boldyreva, E.V., Shakhtshneider, T.P., Ahsbahs, H. et al. Effect of High Pressure on the Polymorphs of Paracetamol. Journal of Thermal Analysis and Calorimetry 68, 437–452 (2002). https://doi.org/10.1023/A:1016079400592

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1016079400592

Search

Navigation