Optical Resolution of Racemic Alcohols via Diastereoisomeric Supramolecular Compound Formation with O,O′-Dibenzoyl-(2R,3R)-tartaric Acid

Kassai, Csaba; Juvancz, Zoltán; Bálint, József; Fogassy, Elemér; Kozma, Dávid

doi:10.1016/s0040-4020(00)00776-6

Cited by 40 publications

(24 citation statements)

References 13 publications

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“…In hexane insoluble reagent contacting the dissolved racemic menthol forms crystalline diastereomeric molecular complex. 59 (as was shown earlier at the crystallization of diastereomers from melt). From the crystalline diastereomer could be isolated the L-MEN with a good enantiomeric purity (ee: 83%).…”

Section: Resolving Agents Forming Diastereomer Complexessupporting

confidence: 54%

Separation of the Mixtures of Chiral Compounds by Crystallization

Pálovics¹,

Faigl²,

Fogassy³

2012

Advances in Crystallization Processes

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Section: Resolving Agents Forming Diastereomer Complexessupporting

confidence: 54%

Separation of the Mixtures of Chiral Compounds by Crystallization

Pálovics¹,

Faigl²,

Fogassy³

2012

Advances in Crystallization Processes

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“…L-(-)-DBTA ( Figure 1) has been known as a chiral selector of enantiomers, such as ephedrine, chiral alcohols, 14 N-methylamphetamine 15 and amino acids. 13 Although L-(-)-DBTA has the ability to resolute enantiomers, the enantioselectivity is still relatively low, especially its extraction capacity is also very low.…”

Section: Introductionmentioning

confidence: 99%

Extractive Resolution of racemic mandelic acid through a bulk liquid membrane containing binary chiral carrier

Yang¹,

Chen²,

Jiao³

2009

J. Braz. Chem. Soc.

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Um método empregando "bulk liquid membrane" (BLM) e o complexo ácido di(2-etilhexil) fosfórico (D2EHPA) e ácido O,O'-dibenzoil-(2R, 3R)-tartárico (L-(-)-DBTA) foi desenvolvido para a separação por extração do ácido mandélico racêmico (rac MA). Os efeitos de tempo de resolução, concentração de D2EHPA na fase orgânica, concentração de rac MA na fase doadora, velocidade de agitação e temperatura sobre a separação por extração foram estudados. Os resultados experimentais evidenciaram que o maior fator de separação (α) 2,74 e o valor do excesso enantiomérico (ee, %) 46,47% foram obtidos quando o tempo de resolução foi de aproximadamente 4 h, a razão de concentração molar de rac MA, D2EHPA e L-(-)-DBTA foi 0,05:0,2:0,3, a velocidade de agitação, 400 r min -1 e a temperatura, 35 °C. O método desenvolvido é útil para a otimização do transporte de sistemas BLM e para a produção em grande escala de enantiômero puro. A method of bulk liquid membrane (BLM) using complex of di(2-ethylhexyl) phosphoric acid (D2EHPA) and O,O'-dibenzoyl-(2R, 3R)-tartaric acid (L-(-)-DBTA) was developed forthe extractive resolution of racemic mandelic acid (rac MA). The effects of resolution time, concentration of D2EHPA in the organic phase, concentration of rac MA in the feed phase, stirring speed and temperature on extractive resolution were studied. The experimental results have shown that the greatest separation factor (α) 2.74 and the enantiomeric excess value (ee, %) 46.47% were obtained when the resolution time was about 4 h, the molar concentration ratio of rac MA, D2EHPA and L-(-)-DBTA 0.05:0.2:0.3, the stirring speed 400 r min -1 and the temperature 35 °C. The developed method is helpful for optimizing the transport of BLM systems and for large-scale production of pure enantiomer.Keywords: D2EHPA, L-(-)-DBTA, bulk liquid membrane, extraction resolution, mandelic acid IntroductionThe production of single-enantiomer drugs is one of the hot-topics in the world. 1-3 Extractive separation of liquid membrane, a new type of extractive separation technology, 4 originated in the 1960´s is widely used in chiral separation process 5,6 due to their cost effectiveness, low energy demand, set-up simplicity and the possibility to be used in continuous mode. Bulk liquid membrane (BLM) is one of the types of liquid membranes. In a BLM, a relatively thick layer of immiscible fluid is used to separate the feed and strip phases. There is no means of support for the membrane phase and it is kept apart from the external phases only by means of its immiscibility. A recent development of chiral resolution in bulk liquid membranes is the incorporation of single enantioselective carrier within the liquid membrane phase, chemically facilitating the transport of a specific compound across the membrane. [7][8][9][10][11] However, the enantioselectivity of the single carrier is somehow low, therefore the use of binary chiral carrier was introduced while looking for new unitary chiral carrier with high separation capacity and large separation scale. Binary chiral c...

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“…6 Moreover, it was also observed that (+)-DBTA can form complexes with some anilides. 7 Since the good complex forming abilities of (+)-DBTA arise from a number of facts. The carboxylic acid groups of (+)-DBTA can donate protons for hydrogen bonding, while it can also behave as a proton acceptor due to the eight oxygen atoms it contains.…”

Section: O O 'mentioning

confidence: 99%

Enantioselective transport of R-clenbuterol through a bulk liquid membrane containing O,O'-dibenzoyl-(2S, 3S)-tartaric

Jiao

Chen

et al. 2007

J. Braz. Chem. Soc.

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Um método de membrana líquida (BLM) usando O, O'-dibenzoil-(2S, 3S)-ácido tartárico foi desenvolvido para o transporte enantioseletivo do clenbuterol racêmico. A influência do pH tampão e da relação entre as concentrações do veículo quiral e do clenbuterol racêmico foi estudada. Verificou-se que as escolhas de pH 7 em solução aquosa e a relação entre as concentrações de 1:4 foram apropriadas. O modelo de transporte cinético estabelecido envolveu duas reações consecutivas irreversíveis de primeira ordem e foram determinadas as constantes de reação aparente de pseudo-primeira ordem. Esse modelo foi adequado para a otimização dos sistemas BLM de transporte visando à produção em larga escala do enantiômero puro.A method of bulk liquid membrane (BLM) using O, O'-dibenzoyl-(2S, 3S)-tartaric acid was developed for the enantioselective transport of racemic clenbuterol. The influence of buffer pH, concentration ratio of chiral carrier to clenbuterol were studied. It was an appropriate choice of such as pH 7 in aqueous solution and concentration ratio of 1:4. The model of kinetic transport was established by means of a kinetic model involving two consecutive irreversible first order reactions. The pseudo-first order apparent rate constants were determined. It is helpful for optimizing the transport of BLM systems and realizing the large-scale production of pure enantiomer.

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Optical Resolution of Racemic Alcohols via Diastereoisomeric Supramolecular Compound Formation with O,O′-Dibenzoyl-(2R,3R)-tartaric Acid

Cited by 40 publications

References 13 publications

Separation of the Mixtures of Chiral Compounds by Crystallization

Separation of the Mixtures of Chiral Compounds by Crystallization

Extractive Resolution of racemic mandelic acid through a bulk liquid membrane containing binary chiral carrier

Enantioselective transport of R-clenbuterol through a bulk liquid membrane containing O,O'-dibenzoyl-(2S, 3S)-tartaric

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