Optical Resolution of Mandelic Acid by Complexation with (<i>S</i>)-(+)-Alanine

Tanaka, Kōichi; Fukuoka, Takatumi; Shiro, M.

doi:10.3184/030823402103172608

Cited by 7 publications

(2 citation statements)

References 2 publications

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“…[20,23] Mandelic acid is often used as a model molecule in investigations targeting chiral separation. [24][25][26][27][28] It is a frequently applied resolving agent itself. The diastereomeric salt of mandelic acid and (R)-1-phenylethanamine has already been the subject of resolution experiments with gas antisolvent precipitation from a dimethyl-sulphoxide -ethyl-acetate mixture, by half-equivalent, equivalent methods as well and by in situ salt formation too.…”

Section: Introductionmentioning

confidence: 99%

Gas Antisolvent Fractionation: a New Method to Obtain Enantiopure Compounds, a Case Study on Mandelic Acid

Kőrösi

Sedon

Komka

et al. 2018

Period. Polytech. Chem. Eng.

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Micronization processes involving supercritical carbon dioxide are rapid methods to produce fine particles. They also might offer the possibility of using less organic solvent than conventional crystallization methods leading to an environmentally friendlier processing. The separation capabilities of such processes are now demonstrated on the diastereomeric resolution of mandelic acid using (R)-1-phenylethanamine as a resolving agent, utilizing the batch type gas antisolvent fractionation as the separation method. A detailed study was conducted on the effects of the operational parameters pressure (12-20 MPa), temperature (35-55 °C) and co-solvent concentration (33-99 mg/ml). At 12 MPa, 35 °C and 99 mg/ml methanol concentration, a selectivity of 0.52 and a diastereomeric excess of 62% was reached. The same operational parameters were applied during the investigation of the recrystallization-based further purification of the diastereomeric salts, applying the resolving agent in molar equivalent quantity to a non-racemic mixture of mandelic acid. It has been found that the more stable (R)-1-phenylethylammonium-(R)-mandelate salt can be purified to de>98% through four additional recrystallization steps following the initial, half-molar equivalent resolution step.

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Section: Introductionmentioning

confidence: 99%

Gas Antisolvent Fractionation: a New Method to Obtain Enantiopure Compounds, a Case Study on Mandelic Acid

Kőrösi

Sedon

Komka

et al. 2018

Period. Polytech. Chem. Eng.

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“…[124] Betaine esters have also been explored for the development of cleavable surfactants. [127,128] The hydrolysis of the betaine esters is strongly pHdependent [124,125,129] and, as a consequence of their micelleforming properties, further increased by micellar catalysis. [128] Betaine ester 56, for example, is completely hydrolyzed within about 20 minutes under alkaline conditions (pH > 8) and only by about 20 % after one hour under acidic conditions (pH < 6).…”

Section: Carboxylatesmentioning

confidence: 99%

Controlled Release of Volatiles under Mild Reaction Conditions: From Nature to Everyday Products

2007

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Volatile organic compounds serve in nature as semiochemicals for communication between species, and are often used as flavors and fragrances in our everyday life. The quite limited longevity of olfactive perception has led to the development of pro-perfumes or pro-fragrances--ideally nonvolatile and odorless fragrance precursors which release the active volatiles by bond cleavage. Only a limited amount of reaction conditions, such as hydrolysis, temperature changes, as well as the action of light, oxygen, enzymes, or microorganisms, can be used to liberate the many different chemical functionalities. This Review describes the controlled chemical release of fragrances and discusses additional challenges such as precursor stability during product storage as well as some aspects concerning toxicity and biodegradability. As the same systems can be applied in different areas of research, the scope of this Review covers fragrance delivery as well as the controlled release of volatiles in general.

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Optical Resolution of Mandelic Acid by Complexation with (S)‐(+)‐Alanine.

2003

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Optical Resolution of Mandelic Acid by Complexation with (S)-(+)-Alanine

Abstract: Racemic mandelic acid (2) was resolved efficiently by complexation with (S)-(+)-alanine (1) and the crystal structure of 2:2:1 complex of (S)-(+)-alanine (1), (R)-(-)-mandelic acid (2) and H 2 O was determined characterizing the hydrogen bond network in the solid state.

Cited by 7 publications

References 2 publications

Gas Antisolvent Fractionation: a New Method to Obtain Enantiopure Compounds, a Case Study on Mandelic Acid

Gas Antisolvent Fractionation: a New Method to Obtain Enantiopure Compounds, a Case Study on Mandelic Acid

Controlled Release of Volatiles under Mild Reaction Conditions: From Nature to Everyday Products

Optical Resolution of Mandelic Acid by Complexation with (S)‐(+)‐Alanine.

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