Processes employing cyclodextrin derivative quaternary salts
OwnerJose R Matosinventor
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Abstract
Chiral salts comprising anionic cyclodextrin derivatives with particular types of non-metal cations are provided. The anionic CD derivative salts can serve as ionic liquids and can possess substantial advantages over currently commercially available ionic liquids particularly for use as chiral phase transfer catalyst, chiral reaction medium, chiral extraction medium, and/or as chiral additive to a chemical process. Methods of preparing the same are provided.
Claims20
An extraction process for the separation of enantiomers or diastereomers, the process comprising:
- a. exposing a solid or liquid containing at least one compound to be extracted to an extraction phase containing a cyclodextrin derivative salt comprising one or more anionic cyclodextrin derivatives and one or more cations independently selected at each occurrence from a phosphonium cation or a quaternary nitrogen-containing cation, wherein the at least one compound is a mixture of Isomer-1 and Isomer-2 of enantiomers or diastereomers, and the salt comprises an anionic cyclodextrin derivative and a quaternary nitrogen-containing cation;
- b. mixing the solid or liquid with the extraction phase for a period of time sufficient to specifically or selectively extract a first portion of Isomer-1 into the extraction phase;
- and
- c. separating the extraction phase from the solid or liquid;
- and
- d. separating the extracted first portion of Isomer-1 from the extraction phase to provide an enantiomerically enriched, enantiomerically pure, diastereomerically-enriched or diastereomerically-pure Isomer-1 of the compound.
A supercritical fluid extraction process for the separation of one or more target compounds from a mass comprising the one or more target compounds, the process comprising:
- a. providing a solid or liquid mass comprising one or more target compounds;
- b. treating the mass with a cyclodextrin derivative salt comprising one or more anionic cyclodextrin derivatives and one or more cations independently selected at each occurrence from a phosphonium cation or a quaternary nitrogen-containing cation and with a supercritical fluid to form an ionic liquid phase and a supercritical fluid phase;
- c. separating the supercritical fluid phase from the phase containing the cyclodextrin derivative salt;
- and
- d. isolating the one or more target compounds from the supercritical fluid phase by removal of the supercritical fluid, e.g. evaporation thereof;
- and/or
- e. isolating the one or more target compounds from the phase containing the cyclodextrin derivative salt by treating the ionic liquid with an aqueous or organic phase into which the one or more compounds is extracted.
A method of separating one or more compounds from a mixture of structurally related compounds, the method comprising:
- a. exposing a solid or liquid containing a mixture of structurally related compounds to an extraction phase containing a cyclodextrin derivative salt, wherein the salt comprises an anionic cyclodextrin derivative and a quaternary nitrogen-containing cation;
- b. mixing the solid or liquid with the extraction phase for a period of time sufficient to specifically or selectively extract one or more compounds from the mixture of structurally related compounds into the extraction phase;
- and
- c. separating the extraction phase from the solid or liquid;
- and
- d. separating the extracted one or more compounds from the extraction phase to provide an enriched or pure one or more compounds.
An extraction process for the separation of a first compound from a mixture of first and second compounds comprising:
- a. exposing a solid or liquid containing at least a first compound and a second compound to an extraction phase containing a cyclodextrin derivative salt, wherein the salt comprises an anionic cyclodextrin derivative and a quaternary nitrogen-containing cation;
- b. mixing the solid or liquid with the extraction phase for a period of time sufficient to specifically or selectively extract a first portion of first compound into the extraction phase;
- c. separating the extraction phase from the solid or liquid;
- and
- d. separating the extracted first portion of first compound from the extraction phase to provide an enriched or pure first compound.
A chemical process comprising:
- a. providing a cyclodextrin derivative salt as a reaction medium, one or more starting materials and optionally one or more catalysts, wherein the salt comprises an anionic cyclodextrin derivative and a quaternary nitrogen-containing cation;
- b. mixing the salt, one or more starting materials and optionally one or more catalysts, whereby the one or more starting materials complexes with the salt in situ, to form a reaction milieu, optionally while heating the reaction milieu, cooling the reaction milieu and/or exposing the reaction milieu to radiation, and causing a chemical reaction to form at least one enantiomerically-enriched, enantiomerically-pure, diastereomerically-pure or diastereomerically-enriched reaction product;
- and
- c. isolating the reaction product.
Dependencies are inferred from the claim text.