Issue 7, 2013
From the journal:

New Journal of Chemistry

The effect of carboxylic acids on glycine polymorphism, salt and co-crystal formation. A comparison of different crystallisation techniques†

Evgeniy A. Losev,*ab   Mikhail A. Mikhailenko,ab   Andrey F. Achkasovb  and  Elena V. Boldyreva*ab  

* Corresponding authors

a Institute of Solid State Chemistry and Mechanochemistry SB RAS, Kutateladze 18, Novosibirsk, Russia

b REC-008, Novosibirsk State University, Pirogova 2, Novosibirsk, Russia
E-mail: losev.88@mail.ru, eboldyreva@yahoo.com
Fax: +7 8 383 363 41 32
Tel: +7 8 383 363 42 06

Abstract

The effect of carboxylic acids on glycine polymorphism, salt and co-crystal formation was compared for slow evaporation of solutions at ambient conditions, spray drying, “fast” and “slow” anti-solvent crystallisation and dry co-grinding. Different phases were found to crystallise from the same starting components, depending on the preparative technique. Small amounts of most carboxylic acids (glutaric acid being the only exception) promoted crystallisation of the γ-polymorph in solution and as a result of co-grinding. When added in equimolar quantities, the same carboxylic acids formed salts with glycine (addition of glutaric acid resulted in co-crystal formation) on slow evaporation of solutions and on co-grinding. Neither succinic nor L-malic acids produced glycine salts, but instead promoted formation of γ-glycine when present in any amount. Anti-solvent crystallisation and spray drying of solutions containing small or large amounts of carboxylic acids produced a variety of glycine polymorphs as both pure phases and their mixtures, whereas only oxalic acid yielded salts. The ability to synthesise glycinium semi-oxalate form II by spray drying was demonstrated.

Graphical abstract: The effect of carboxylic acids on glycine polymorphism, salt and co-crystal formation. A comparison of different crystallisation techniques

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Article information

DOI
https://doi.org/10.1039/C3NJ41169A
Article type
Paper
Submitted
26 Dec 2012
Accepted
25 Mar 2013
First published
26 Mar 2013

New J. Chem., 2013,37, 1973-1981

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The effect of carboxylic acids on glycine polymorphism, salt and co-crystal formation. A comparison of different crystallisation techniques

E. A. Losev, M. A. Mikhailenko, A. F. Achkasov and E. V. Boldyreva, New J. Chem., 2013, 37, 1973 DOI: 10.1039/C3NJ41169A

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