Recovery of pure products from ionic liquids using supercritical carbon dioxide as a co-solvent in extractions or as an anti-solvent in precipitations

M.C. Kroon, J. Spronsen, van, C.J. Peters, R.A. Sheldon, G.J. Witkamp

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    Abstract

    In this paper two advanced methods for separation and purification of products from ionic liquids by using supercritical carbon dioxide as a co-solvent in extractions or as an anti-solvent in precipitations are demonstrated. As an example, the recovery of the product N-acetyl-(S)-phenylalanine methyl ester (APAM) from the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]) was studied experimentally. APAM is the product of the asymmetric hydrogenation of methyl-(Z)-a-acetamidocinnamate (MAAC). For extraction of the product, the solubility of APAM in CO2 should be sufficiently high. This solubility is 1.78 g kg-1 at 12.0 MPa and 323 K, whereas [bmim][BF4] has a negligible solubility in scCO2. The extracted product was found to contain no detectible amount of ionic liquid. The solubility of the reactant MAAC in scCO2 is five times lower than the solubility of APAM, which means that a selectivity towards extraction of APAM exists. The product APAM was also precipitated out of the ionic liquid phase using scCO2 as an anti-solvent, enabled by the lower solubility of APAM in ionic liquid/scCO2 mixtures compared to the solubility in the pure ionic liquid at atmospheric conditions (650 g l-1). For example, the solubility of APAM in ionic liquid + scCO2 (1:1.34 g g-1) at 313 K and 18.0 MPa is 162 g l-1. After precipitation the formed crystals can be washed using CO2 to obtain pure product.
    LanguageEnglish
    Pages246-249
    Number of pages4
    JournalGreen Chemistry
    Volume8
    Issue number3
    DOIs
    StatePublished - 2006

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    Ionic Liquids
    Ionic liquids
    Carbon Dioxide
    Carbon dioxide
    solubility
    Solubility
    carbon dioxide
    Recovery
    ionic liquid
    product
    ester
    Hydrogenation
    Purification
    purification
    Esters
    crystal
    Crystals

    Cite this

    @article{2795ea8e270641bbb98b3daf5dfe82bc,
    title = "Recovery of pure products from ionic liquids using supercritical carbon dioxide as a co-solvent in extractions or as an anti-solvent in precipitations",
    abstract = "In this paper two advanced methods for separation and purification of products from ionic liquids by using supercritical carbon dioxide as a co-solvent in extractions or as an anti-solvent in precipitations are demonstrated. As an example, the recovery of the product N-acetyl-(S)-phenylalanine methyl ester (APAM) from the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]) was studied experimentally. APAM is the product of the asymmetric hydrogenation of methyl-(Z)-a-acetamidocinnamate (MAAC). For extraction of the product, the solubility of APAM in CO2 should be sufficiently high. This solubility is 1.78 g kg-1 at 12.0 MPa and 323 K, whereas [bmim][BF4] has a negligible solubility in scCO2. The extracted product was found to contain no detectible amount of ionic liquid. The solubility of the reactant MAAC in scCO2 is five times lower than the solubility of APAM, which means that a selectivity towards extraction of APAM exists. The product APAM was also precipitated out of the ionic liquid phase using scCO2 as an anti-solvent, enabled by the lower solubility of APAM in ionic liquid/scCO2 mixtures compared to the solubility in the pure ionic liquid at atmospheric conditions (650 g l-1). For example, the solubility of APAM in ionic liquid + scCO2 (1:1.34 g g-1) at 313 K and 18.0 MPa is 162 g l-1. After precipitation the formed crystals can be washed using CO2 to obtain pure product.",
    author = "M.C. Kroon and {Spronsen, van}, J. and C.J. Peters and R.A. Sheldon and G.J. Witkamp",
    year = "2006",
    doi = "10.1039/b512303h",
    language = "English",
    volume = "8",
    pages = "246--249",
    journal = "Green Chemistry",
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    publisher = "Royal Society of Chemistry",
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    }

    Recovery of pure products from ionic liquids using supercritical carbon dioxide as a co-solvent in extractions or as an anti-solvent in precipitations. / Kroon, M.C.; Spronsen, van, J.; Peters, C.J.; Sheldon, R.A.; Witkamp, G.J.

    In: Green Chemistry, Vol. 8, No. 3, 2006, p. 246-249.

    Research output: Contribution to journalArticleAcademicpeer-review

    TY - JOUR

    T1 - Recovery of pure products from ionic liquids using supercritical carbon dioxide as a co-solvent in extractions or as an anti-solvent in precipitations

    AU - Kroon,M.C.

    AU - Spronsen, van,J.

    AU - Peters,C.J.

    AU - Sheldon,R.A.

    AU - Witkamp,G.J.

    PY - 2006

    Y1 - 2006

    N2 - In this paper two advanced methods for separation and purification of products from ionic liquids by using supercritical carbon dioxide as a co-solvent in extractions or as an anti-solvent in precipitations are demonstrated. As an example, the recovery of the product N-acetyl-(S)-phenylalanine methyl ester (APAM) from the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]) was studied experimentally. APAM is the product of the asymmetric hydrogenation of methyl-(Z)-a-acetamidocinnamate (MAAC). For extraction of the product, the solubility of APAM in CO2 should be sufficiently high. This solubility is 1.78 g kg-1 at 12.0 MPa and 323 K, whereas [bmim][BF4] has a negligible solubility in scCO2. The extracted product was found to contain no detectible amount of ionic liquid. The solubility of the reactant MAAC in scCO2 is five times lower than the solubility of APAM, which means that a selectivity towards extraction of APAM exists. The product APAM was also precipitated out of the ionic liquid phase using scCO2 as an anti-solvent, enabled by the lower solubility of APAM in ionic liquid/scCO2 mixtures compared to the solubility in the pure ionic liquid at atmospheric conditions (650 g l-1). For example, the solubility of APAM in ionic liquid + scCO2 (1:1.34 g g-1) at 313 K and 18.0 MPa is 162 g l-1. After precipitation the formed crystals can be washed using CO2 to obtain pure product.

    AB - In this paper two advanced methods for separation and purification of products from ionic liquids by using supercritical carbon dioxide as a co-solvent in extractions or as an anti-solvent in precipitations are demonstrated. As an example, the recovery of the product N-acetyl-(S)-phenylalanine methyl ester (APAM) from the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]) was studied experimentally. APAM is the product of the asymmetric hydrogenation of methyl-(Z)-a-acetamidocinnamate (MAAC). For extraction of the product, the solubility of APAM in CO2 should be sufficiently high. This solubility is 1.78 g kg-1 at 12.0 MPa and 323 K, whereas [bmim][BF4] has a negligible solubility in scCO2. The extracted product was found to contain no detectible amount of ionic liquid. The solubility of the reactant MAAC in scCO2 is five times lower than the solubility of APAM, which means that a selectivity towards extraction of APAM exists. The product APAM was also precipitated out of the ionic liquid phase using scCO2 as an anti-solvent, enabled by the lower solubility of APAM in ionic liquid/scCO2 mixtures compared to the solubility in the pure ionic liquid at atmospheric conditions (650 g l-1). For example, the solubility of APAM in ionic liquid + scCO2 (1:1.34 g g-1) at 313 K and 18.0 MPa is 162 g l-1. After precipitation the formed crystals can be washed using CO2 to obtain pure product.

    U2 - 10.1039/b512303h

    DO - 10.1039/b512303h

    M3 - Article

    VL - 8

    SP - 246

    EP - 249

    JO - Green Chemistry

    T2 - Green Chemistry

    JF - Green Chemistry

    SN - 1463-9262

    IS - 3

    ER -