Effects of a structurally related substance on the crystallization of paracetamol
Effects of a structurally related substance on the crystallization of paracetamol
Ali SALEEMI1, I.I. ONYEMELUKWE1, Zoltan NAGY1,2()
1. Department of Chemical Engineering, Loughborough University, Loughborough, LE11 3TU, UK; 2. School of Chemical Engineering, Purdue University, West Lafayette, Ind. 47907, USA
Paracetamol (PCM) was crystallized from an isopropanol (IPA) solution containing various small amounts of metacetamol as an additive. The effect on the nucleation kinetics was studied by measuring the induction time to nucleation and the metastable zone width using focused beam reflectance measurements (FBRM) and attenuated total reflectance (ATR-UV/Vis) spectroscopy. Both the induction time and the metastable zone width were expressed as functions of the additive concentration. Small amounts of metacetamol (1–4 mol-%) were found to cause significant inhibition to the nucleation by extending both the induction time and the metastable zone width. A progressive change in the morphology of the paracetamol crystals from tabular to columnar habit was observed with increasing metacetamol concentration. The solvent also had a significant effect on the size of the paracetamol crystals as smaller crystals were obtained in IPA than in aqueous solution. The dissolution rate of paracetamol was improved by the incorporation of metacetamol with 4 mol-% having the most effect. A supersaturation control (SSC) approach was implemented for the PCM-IPA system with and without metacetamol in an attempt to control and obtain larger metacetamol-doped paracetamol crystals.
Corresponding Author(s):
NAGY Zoltan,Email:zknagy@purdue.edu
引用本文:
. Effects of a structurally related substance on the crystallization of paracetamol[J]. Frontiers of Chemical Science and Engineering, 2013, 7(1): 79-87.
Ali SALEEMI, I.I. ONYEMELUKWE, Zoltan NAGY. Effects of a structurally related substance on the crystallization of paracetamol. Front Chem Sci Eng, 2013, 7(1): 79-87.
Mullin J W. Industrial Crystallisation. London: Butterworths, 1993, 277-278
2
Klug D L. The influence of impurities and solvents on crystallisation. In: Myerson A, ed. Handbook of Industrial Crystallisation. New York: Butterworths, 1993, 65-87
3
Weissbuch I, Leiserowitz L, Lahav M. Tailor-made additives and impurities. In: Mersmann A, ed. Crystallisation Technology Handbook . New York: Marcel Dekker, 1995, 401-457
4
Prasad K V R, Ristic R I, Sheen D B, Sherwood J N. Crystallization of paracetamol from solution in the presence and absence of impurity. International Journal of Pharmaceutics , 2001, 215(1-2): 29-44 doi: 10.1016/S0378-5173(00)00653-0
5
Thompson C, Davies M C, Roberts C J, Tendler S J B, Wilkinson M J. The effects of additives on the growth and morphology of paracetamol (acetaminophen) crystals. International Journal of Pharmaceutics , 2004, 280(1-2): 137-150 doi: 10.1016/j.ijpharm.2004.05.010
6
Hendriksen B A, Grant D J W. The effect of structurally related substances on the nucleation kinetics of paracetamol (acetaminophen). Journal of Crystal Growth , 1995, 156(3): 252-260 doi: 10.1016/0022-0248(95)00301-0
7
Hendriksen B A, Grant D J W, Meenan P, Green D A. Crystallisation of paracetamol (acetaminophen) in the presence of structurally related substances. Journal of Crystal Growth , 1998, 183(4): 629-640 doi: 10.1016/S0022-0248(97)00488-0
8
Prasad K V R, Ristic R I, Sheen D B, Sherwood J N. Dissolution kinetics of paracetamol single crystals. International Journal of Pharmaceutics , 2002, 238(1-2): 29-41 doi: 10.1016/S0378-5173(02)00053-4
9
Chow A H L, Chow P K K, Zhongshan W, Grant D J W. Modification of acetaminophen crystals: influence of growth in aqueous solutions containing p-acetoxyacetanilide on crystal properties. International Journal of Pharmaceutics , 1985, 24(2-3): 239-258 doi: 10.1016/0378-5173(85)90024-9
10
Femi-Oyewo M N, Spring M S. Studies on paracetamol crystals produced by growth in aqueous solutions. International Journal of Pharmaceutics , 1994, 112(1): 17-28 doi: 10.1016/0378-5173(94)90257-7
11
Shekunov B Y, Grant D J W. In situ optical interferometric studies of the growth and dissolution behavior of paracetamol (acetaminophen). 1. Growth kinetics. Journal of Physical Chemistry B , 1997, 101(20): 3973-3979 doi: 10.1021/jp9639298
12
Becker R, D?ring W. Kinetische Behandlung der Keimbildung in übers?ttigten D?mpfen. Annals of Physics , 1935, 24: 719-752
13
Nielsen A E. Kinetics of Precipitation. Oxford: Pergamon, 1964, 15-25
14
Nielsen A E, S?hnel O. Interfacial tensions electrolyte crystal-aqueous solution, from nucleation data. Journal of Crystal Growth , 1971, 11(3): 233-242 doi: 10.1016/0022-0248(71)90090-X
15
Van Hook A, Bruno A J. Nucleation and growth in sucrose solutions. Discussions of the Faraday Society , 1949, 5: 112-117 doi: 10.1039/df9490500112
16
Sangwal K. Effect of impurities on the metastable zone width of solute-solvent systems. Journal of Crystal Growth , 2009, 311(16): 4050-4061 doi: 10.1016/j.jcrysgro.2009.06.045
17
Nyvlt J, Sohnel O, Matuchova M, Broul M. Kinetics of Industrial Crystallisation. Amsterdam: Elsevier, 1985, 82
Dhanaraj P V, Bhagavannarayana G, Rajesh N P. Effect of amino acid additives on crystal growth parameters and properties of ammonium dihydrogen orthophosphate crystals. Materials Chemistry and Physics , 2008, 112(2): 490-495 doi: 10.1016/j.matchemphys.2008.06.003
20
Saleemi A N, Rielly C D, Nagy Z K. Comparative investigation of supersaturation and automated direct nucleation control of crystal size distributions using ATR-UV/Vis spectroscopy and FBRM. Crystal Growth & Design , 2012, 12(4): 1792-1807 doi: 10.1021/cg201269c
21
Gutwald T, Mersmann A. Batch cooling crystallization at constant supersaturation: technique and experimental results. Chemical Engineering & Technology , 1990, 13(1): 229-237 doi: 10.1002/ceat.270130131
22
Fujiwara M, Chow P S, Ma D L, Braatz R D. Paracetamol crystallization using laser backscattering and ATR-FTIR spectroscopy: metastability, agglomeration, and control. Crystal Growth & Design , 2002, 2(5): 363-370 doi: 10.1021/cg0200098
23
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. Crystal Growth & Design , 2009, 9(3): 1378-1384 doi: 10.1021/cg800595v
24
Hojjati H, Rohani S. Measurement and prediction of solubility of paracetamol in water-isopropanol solution. Part 1. Measurement and data analysis. Organic Process Research & Development , 2006, 10(6): 1101-1109 doi: 10.1021/op060073o
25
Cabrera N, Vermilyea D A. The growth of crystals from solution. In: Doremus R H, Turnbull D, eds. Growth and Perfection of Crystals . New York: Wiley, 1958, 393-410
26
Ristic R I, Finnie S, Sheen D B, Sherwood J N. Macro- and micromorphology of monoclinic paracetamol grown from pure aqueous solution. Journal of Physical Chemistry B , 2001, 105(38): 9057-9066 doi: 10.1021/jp003757l
27
Finnie S, Prasad K R, Sheen D, Sherwood J. Microhardness and dislocation identification studies on paracetamol single crystals. Pharmaceutical Research , 2001, 18(5): 674-681 doi: 10.1023/A:1011093612868
28
Lahav M, Leiserowitz L. The effect of solvent on crystal growth and morphology. Chemical Engineering Science , 2001, 56(7): 2245-2253 doi: 10.1016/S0009-2509(00)00459-0
29
Finnie S, Kennedy A R, Prasad K V R, Ristic R I, Sheen D B, Sherwood J N. para-Acetoxyacetanilide. Acta Crystallographica , 1999, Section C, 55(2): 234-236