Highly efficient synthesis of alkyl levulinates from α-angelica lactone, catalysed with Lewis acidic trifloaluminate ionic liquids supported on carbon nanotubes

Piotr Latos, Anna Szelwicka, Slawomir Boncel, Sebastian Jurczyk, Malgorzata Swadzba-Kwasny, Anna Chrobok

Research output: Contribution to journalArticle

Abstract

Levulinic acid esters (LAEs) were synthesized from α-angelica lactone and alcohols, in a reaction catalyzed by a new family of chloride-free Lewis acidic ionic liquids, containing trifloaluminate anions, [Al(OTf)3+n]n−. Changing the catalyst from poorly soluble Al(OTf)3 (used as suspension) to fully homogeneous trifloaluminate ionic liquids resulted in shorter reaction times required for full α-AL conversion (60 min at 60 °C for 0.1 mol % catalyst loading) and unprecedented selectivities to LAEs, reaching >99%. Supporting the trifloaluminate ionic liquid on multiwalled carbon nanotubes gave an easily recyclable system, with no leaching observed over six cycles. Mechanistic considerations suggest that the propensity of Al(OTf)3 to undergo very slow hydrolysis results in the correct balance of Brønsted and Lewis acidic sites in the system, which inhibit byproduct formation.
Original languageEnglish
Pages (from-to)5184-5191
Number of pages8
JournalACS Sustainable Chemistry & Engineering
Volume7
Issue number5
Early online date08 Feb 2019
DOIs
Publication statusPublished - 2019

Fingerprint

Ionic Liquids
Carbon Nanotubes
Ionic liquids
Carbon nanotubes
ester
Esters
catalyst
Catalysts
Acids
Catalyst selectivity
Multiwalled carbon nanotubes (MWCN)
acid
Leaching
Anions
Byproducts
Chlorides
anion
alcohol
hydrolysis
Hydrolysis

Keywords

  • Angelica lactone
  • Carbon nanotubes
  • Ionic liquids
  • Levulinic acid esters
  • Lewis acids
  • Supported ionic liquid phase
  • Trifloaluminate ionic liquids

Cite this

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title = "Highly efficient synthesis of alkyl levulinates from α-angelica lactone, catalysed with Lewis acidic trifloaluminate ionic liquids supported on carbon nanotubes",
abstract = "Levulinic acid esters (LAEs) were synthesized from α-angelica lactone and alcohols, in a reaction catalyzed by a new family of chloride-free Lewis acidic ionic liquids, containing trifloaluminate anions, [Al(OTf)3+n]n−. Changing the catalyst from poorly soluble Al(OTf)3 (used as suspension) to fully homogeneous trifloaluminate ionic liquids resulted in shorter reaction times required for full α-AL conversion (60 min at 60 °C for 0.1 mol {\%} catalyst loading) and unprecedented selectivities to LAEs, reaching >99{\%}. Supporting the trifloaluminate ionic liquid on multiwalled carbon nanotubes gave an easily recyclable system, with no leaching observed over six cycles. Mechanistic considerations suggest that the propensity of Al(OTf)3 to undergo very slow hydrolysis results in the correct balance of Br{\o}nsted and Lewis acidic sites in the system, which inhibit byproduct formation.",
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author = "Piotr Latos and Anna Szelwicka and Slawomir Boncel and Sebastian Jurczyk and Malgorzata Swadzba-Kwasny and Anna Chrobok",
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journal = "ACS Sustainable Chemistry & Engineering",
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Highly efficient synthesis of alkyl levulinates from α-angelica lactone, catalysed with Lewis acidic trifloaluminate ionic liquids supported on carbon nanotubes. / Latos, Piotr; Szelwicka, Anna; Boncel, Slawomir; Jurczyk, Sebastian; Swadzba-Kwasny, Malgorzata; Chrobok, Anna.

In: ACS Sustainable Chemistry & Engineering, Vol. 7, No. 5, 2019, p. 5184-5191.

Research output: Contribution to journalArticle

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T1 - Highly efficient synthesis of alkyl levulinates from α-angelica lactone, catalysed with Lewis acidic trifloaluminate ionic liquids supported on carbon nanotubes

AU - Latos, Piotr

AU - Szelwicka, Anna

AU - Boncel, Slawomir

AU - Jurczyk, Sebastian

AU - Swadzba-Kwasny, Malgorzata

AU - Chrobok, Anna

PY - 2019

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AB - Levulinic acid esters (LAEs) were synthesized from α-angelica lactone and alcohols, in a reaction catalyzed by a new family of chloride-free Lewis acidic ionic liquids, containing trifloaluminate anions, [Al(OTf)3+n]n−. Changing the catalyst from poorly soluble Al(OTf)3 (used as suspension) to fully homogeneous trifloaluminate ionic liquids resulted in shorter reaction times required for full α-AL conversion (60 min at 60 °C for 0.1 mol % catalyst loading) and unprecedented selectivities to LAEs, reaching >99%. Supporting the trifloaluminate ionic liquid on multiwalled carbon nanotubes gave an easily recyclable system, with no leaching observed over six cycles. Mechanistic considerations suggest that the propensity of Al(OTf)3 to undergo very slow hydrolysis results in the correct balance of Brønsted and Lewis acidic sites in the system, which inhibit byproduct formation.

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