Cocrystal Formation through Mechanochemistry: from Neat and Liquid-Assisted Grinding to Polymer-Assisted Grinding.

Mechanochemistry is an effective method for the preparation of multicomponent crystal systems. In the present work, we propose an alternative to the established liquid-assisted grinding (LAG) approach. Polymer-assisted grinding (POLAG) is demonstrated to provide a new class of catalysts for improving reaction rate and increasing product diversity during mechanochemical cocrystallization reactions. We demonstrate that POLAG provides advantages comparable to the conventional liquid-assisted process, whilst eliminating the risk of unwanted solvate formation as well as enabling control of resulting particle size. It represents a new approach for the development of functional materials through mechanochemistry, and possibly opens new routes toward the understanding of the mechanisms and pathways of mechanochemical cocrystal formation.

[1]  G. Coquerel,et al.  Inhibition of the spontaneous polymorphic transition of pyrazinamide γ form at room temperature by co-spray drying with 1,3-dimethylurea. , 2015, International journal of pharmaceutics.

[2]  M. Eddleston,et al.  Introductory lecture: Mechanochemistry, a versatile synthesis strategy for new materials. , 2014, Faraday discussions.

[3]  R. Pinal,et al.  Matrix-assisted cocrystallization (MAC) simultaneous production and formulation of pharmaceutical cocrystals by hot-melt extrusion. , 2014, Journal of pharmaceutical sciences.

[4]  F. Emmerling,et al.  Evaluation of the formation pathways of cocrystal polymorphs in liquid-assisted syntheses , 2014 .

[5]  M. Eddleston,et al.  Polymorphs, hydrates and solvates of a co-crystal of caffeine with anthranilic acid. , 2014, Acta crystallographica Section B, Structural science, crystal engineering and materials.

[6]  N. Rodríguez-Hornedo,et al.  Pharmaceutical cocrystals and poorly soluble drugs. , 2013, International journal of pharmaceutics.

[7]  Elena Boldyreva,et al.  Mechanochemistry of inorganic and organic systems: what is similar, what is different? , 2013, Chemical Society reviews.

[8]  Scott L. Childs,et al.  Formulation of a danazol cocrystal with controlled supersaturation plays an essential role in improving bioavailability. , 2013, Molecular pharmaceutics.

[9]  B. Perissutti,et al.  Drug salt formation via mechanochemistry: the case study of vincamine. , 2013, Molecular pharmaceutics.

[10]  Tu Lee,et al.  Continuous Co-Crystallization As a Separation Technology: The Study of 1:2 Co-Crystals of Phenazine–Vanillin , 2012 .

[11]  James Mack,et al.  Mechanochemistry: opportunities for new and cleaner synthesis. , 2012, Chemical Society reviews.

[12]  S. Childs,et al.  The role of solvent in mechanochemical and sonochemical cocrystal formation: a solubility-based approach for predicting cocrystallisation outcome , 2009 .

[13]  William Jones,et al.  Recent Advances in Understanding the Mechanism of Cocrystal Formation via Grinding , 2009 .

[14]  T. Friščić,et al.  Cocrystal architecture and properties: design and building of chiral and racemic structures by solid-solid reactions. , 2007, Faraday discussions.

[15]  T. Friščić,et al.  Screening for pharmaceutical cocrystal hydrates via neat and liquid-assisted grinding. , 2007, Molecular pharmaceutics.

[16]  Andrew V. Trask,et al.  An overview of pharmaceutical cocrystals as intellectual property. , 2007, Molecular pharmaceutics.

[17]  G. Day,et al.  Terahertz time-domain spectroscopy and the quantitative monitoring of mechanochemical cocrystal formation. , 2007, Nature Materials.

[18]  A. Matzger,et al.  Polymer-induced heteronucleation for the discovery of new extended solids. , 2006, Angewandte Chemie.

[19]  A. Matzger,et al.  Crystalline polymorph selection and discovery with polymer heteronuclei. , 2005, Journal of the American Chemical Society.

[20]  D. Braga,et al.  Reactions between or within molecular crystals. , 2004, Angewandte Chemie.

[21]  Dario Braga,et al.  Reaktionen zwischen und in Molekülkristallen , 2004 .

[22]  W. Jones,et al.  Mechanochemistry and co-crystal formation: effect of solvent on reaction kinetics. , 2002, Chemical communications.

[23]  T. Shakhtshneider Phase transformations and stabilization of metastable states of molecular crystals under mechanical activation , 1997 .

[24]  V. Boldyrev,et al.  Mechanochemistry and mechanical activation of solids , 1990 .

[25]  V. Boldyrev Control of the Reactivity of Solids , 1979 .

[26]  M. Gupta,et al.  The crystal structure of mesaconic acid, C5H6O4 , 1972 .

[27]  M. Eddleston,et al.  Screening for polymorphs of cocrystals: a case study , 2013 .

[28]  J. Klinowski,et al.  Crystal engineering using co-crystallisation of phenazine with dicarboxylic acids , 2000 .