Impurity exclusion and retention during crystallisation and recrystallisation - the phenacetin by ethylation of paracetamol process

Science Foundation Ireland (05/PICA/B802/EC07, 07/SRC/B1158 and 12/RC/227505); Irish Research Council (Enterprise Partnership Scheme (IRSCET-Clarochem-2010-02)); University College Cork (UCC 2013 Strategic Research Fund); Clarochem (Ireland) Ltd

[1]  D. Allan,et al.  The formation of paracetamol (acetaminophen) adducts with hydrogen-bond acceptors. , 2002, Acta crystallographica. Section B, Structural science.

[2]  S. Clissold,et al.  Paracetamol and Phenacetin , 2012, Drugs.

[3]  L. Addadi,et al.  Resolution of conglomerates with the assistance of tailor-made impurities. Generality and mechanistic aspects of the "rule of reversal". A new method for assignment of absolute configuration , 1982 .

[4]  Taking Advantage of Polymorphism To Effect an Impurity Removal: Development of a Thermodynamic Crystal Form of (R,R)-Formoterol Tartrate , 2002 .

[5]  T. Koetzle,et al.  Reduction in crystal symmetry of a solid solution: a neutron diffraction study at 15 K of the host/guest system asparagine/aspartic acid , 1989 .

[6]  C. C. Seaton,et al.  Ordered Aggregation of Benzamide Crystals Induced Using a “Motif Capper” Additive , 2005 .

[7]  M. Andreeta.  CRYSTALLIZATION SCIENCE AND TECHNOLOGY , 2012 .

[8]  A. Bauer-Brandl,et al.  Redetermination of p-ethoxyacetanilide (phenacetin) , 2006 .

[9]  C. Hough,et al.  Drugs in the chemistry laboratory: The conversion of acetaminophen into phenacetin , 1979 .

[10]  H. Illias,et al.  Molecular Crystals and Liquid Crystals , 2011 .

[11]  Alfred Y Lee,et al.  Influence of Impurities on the Solution-Mediated Phase Transformation of an Active Pharmaceutical Ingredient , 2005 .

[12]  A. Myerson,et al.  Purification of Structurally Similar Compounds by the Formation of Impurity Co-Former Complexes in Solution , 2013 .

[13]  Geoffrey P. F. Wood,et al.  Quantitative Solution Measurement for the Selection of Complexing Agents to Enable Purification by Impurity Complexation , 2014 .

[14]  S. Rohani,et al.  Polymorphic Behavior and Crystal Habit of an Anti-Viral/HIV Drug: Stavudine , 2006 .

[15]  Phenacetin Crystallization: Cooling Regimes and Crystal Morphology , 2012 .

[16]  Margaret C. Etter,et al.  Encoding and decoding hydrogen-bond patterns of organic compounds , 1990 .

[17]  A. Bond,et al.  Influence of impurities on the crystallisation of 5-X-aspirin and 5-X-aspirin anhydride polymorphs (X = Cl, Br, Me) , 2011 .

[18]  S. P. Stokes,et al.  Utilizing Sulfoxide...Iodine Halogen Bonding for Cocrystallization , 2012 .

[19]  J. Ulrich,et al.  Predicting the effect of impurity adsorption on crystal morphology , 2007 .

[20]  M. Haisa,et al.  The Monoclinic Form of p‐Hydroxyacetanilide , 1976 .

[21]  Masatoshi Kawahata,et al.  Novel pharmaceutical cocrystal consisting of paracetamol and trimethylglycine, a new promising cocrystal former. , 2014, International journal of pharmaceutics.

[22]  M. Idelson,et al.  Controlled Modification of Crystal Habit via “Tailor‐Made” Impurities. Application to Benzamide , 1982 .