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Objectives: development of supercritical diastereomer crystallization methods competitive in efficiency to the traditional solvent based crystallizations and having lower environmental effects.

Tasks and methodology:

  • Literature survey
  • Screening of promising resolving agents for all racemates (4 to 6). Selection of the two best pairs.
  • Measurement of solubility of the selected racemate(s) in CO2 and in CO2-solvent mixtures.
  • Development of the high pressure diastereomeric salt precipitation processes. (separately for the two pairs)
  • Critical evaluation and simple mathematical modelling of results. 

Results:

  • racemate – resolving agent pairs grouped to no salt / no enantioselectivity / poor enantioselectivity / good enantioselectivity groups
  • timeframe of salt formation mapped and analytical methodology developed
  • high pressure diastereomeric salt formation process developed and optimised

Selected publications: 

Amit D Zodge, Petra Bombicz, Edit Székely, György Pokol, János Madarász, Structural, analytical and DSC references to resolution of 2-methoxy-2-phenylacetic acid with chiral 1-cyclohexylethylamines through gas-antisolvent precipitation THERMOCHIMICA ACTA 648: pp. 23-31. (2017)

A Zodge, M Kőrösi, M Tárkányi, J Madarász, I M Szilágyi, T Sohajda, E Székely, Gas Antisolvent Approach for the Precipitation of -Methoxyphenylacetic Acid – (R)-1-Cyclohexylethylamine Diateromeric Salt CHEMICAL AND BIOCHEMICAL ENGINEERING QUARTERLY 31:(3) (2017)

László Lőrincz, György Bánsághi, Máté Zsemberi, Sandra de Simon Brezmes, Imre Miklós Szilágyi, János Madarász, Tamás Sohajda, Edit Székely, Diastereomeric salt precipitation based resolution of ibuprofen by gas antisolvent method, JOURNAL OF SUPERCRITICAL FLUIDS 118: pp. 48-53. (2016)

   
© BME, Research Group on Supercritical Fluids, 2015