Cocrystallization out of the blue: DL-mandelic acid/ethyl-DL-mandelate cocrystal

Natalia Tumanova, Ricky Payen, Géraldine Springuel, Bernadette Norberg, Koen Robeyns, Cécile Le Duff, Johan Wouters, Tom Leyssens

Research output: Contribution to journalArticle

Abstract

This work focuses on a peculiar behavior of racemic mandelic acid in ethanol solution. Dissolution of racemic mandelic acid in ethanol followed by evaporation to dryness results in a DL-mandelic acid/ethyl-DL-mandelate cocrystal. This behavior indicates that racemic mandelic acid tends not only to transform into an ester in ethanol, but also to cocrystallize with untransformed acid molecules. Cocrystal formation for mandelic acid in ethanol was found to be reproducible under various conditions. DL-tropic acid and DL-phenyllactic acid that contain similar functional groups and that were tested as well, on the other hand, showed no cocrystal formation: DL-phenyllactic acid partly converted into an ester, whereas DL-tropic acid mostly recrystallized.

Original languageEnglish
Pages (from-to)397-402
Number of pages6
JournalJournal of molecular structure
Volume1127
DOIs
Publication statusPublished - 5 Jan 2017

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Ethanol
Acids
Esters
Functional groups
Dissolution
Evaporation
mandelic acid
Molecules
tropic acid

Keywords

  • Cocrystallization
  • Esterification
  • Mandelic acid

Cite this

Tumanova, N., Payen, R., Springuel, G., Norberg, B., Robeyns, K., Le Duff, C., ... Leyssens, T. (2017). Cocrystallization out of the blue: DL-mandelic acid/ethyl-DL-mandelate cocrystal. Journal of molecular structure, 1127, 397-402. https://doi.org/10.1016/j.molstruc.2016.07.109
Tumanova, Natalia ; Payen, Ricky ; Springuel, Géraldine ; Norberg, Bernadette ; Robeyns, Koen ; Le Duff, Cécile ; Wouters, Johan ; Leyssens, Tom. / Cocrystallization out of the blue : DL-mandelic acid/ethyl-DL-mandelate cocrystal. In: Journal of molecular structure. 2017 ; Vol. 1127. pp. 397-402.
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Tumanova, N, Payen, R, Springuel, G, Norberg, B, Robeyns, K, Le Duff, C, Wouters, J & Leyssens, T 2017, 'Cocrystallization out of the blue: DL-mandelic acid/ethyl-DL-mandelate cocrystal', Journal of molecular structure, vol. 1127, pp. 397-402. https://doi.org/10.1016/j.molstruc.2016.07.109

Cocrystallization out of the blue : DL-mandelic acid/ethyl-DL-mandelate cocrystal. / Tumanova, Natalia; Payen, Ricky; Springuel, Géraldine; Norberg, Bernadette; Robeyns, Koen; Le Duff, Cécile; Wouters, Johan; Leyssens, Tom.

In: Journal of molecular structure, Vol. 1127, 05.01.2017, p. 397-402.

Research output: Contribution to journalArticle

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T2 - DL-mandelic acid/ethyl-DL-mandelate cocrystal

AU - Tumanova, Natalia

AU - Payen, Ricky

AU - Springuel, Géraldine

AU - Norberg, Bernadette

AU - Robeyns, Koen

AU - Le Duff, Cécile

AU - Wouters, Johan

AU - Leyssens, Tom

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AB - This work focuses on a peculiar behavior of racemic mandelic acid in ethanol solution. Dissolution of racemic mandelic acid in ethanol followed by evaporation to dryness results in a DL-mandelic acid/ethyl-DL-mandelate cocrystal. This behavior indicates that racemic mandelic acid tends not only to transform into an ester in ethanol, but also to cocrystallize with untransformed acid molecules. Cocrystal formation for mandelic acid in ethanol was found to be reproducible under various conditions. DL-tropic acid and DL-phenyllactic acid that contain similar functional groups and that were tested as well, on the other hand, showed no cocrystal formation: DL-phenyllactic acid partly converted into an ester, whereas DL-tropic acid mostly recrystallized.

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KW - Esterification

KW - Mandelic acid

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