Enhanced Extraction of Phenol from Model Oils Using Ionic Liquids Elucidated with Neutron Diffraction

Adam H. Turner; Emily L. Byrne; Thaise Pereira; John D. Holbrey

doi:10.1039/D0CP01013H

Enhanced Extraction of Phenol from Model Oils Using Ionic Liquids Elucidated with Neutron Diffraction

Adam H. Turner^*, Emily L. Byrne, Thaise Pereira, John D. Holbrey

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

178 Downloads (Pure)

Abstract

Aromatic cation ionic liquids (ILs) based on alkylpyridiniums are shown to be good phenol extractants from model oils (hexane/toluene). ILs with hard basic anions are found to have best extraction efficiency consistent with tetraalkylammonium salts ([NR₄]X). Key extraction interactions were analysed using small angle neutron diffraction. Trifluoromethanesulfonate ([OTf]^- or triflate) anions provide the synergistic effects of reduced cation-phenol centre of mass (COM) distances and increased hydrogen bonding that are linked to the improved extraction efficiency. Increases in cation electron density (methyl-pyridinium ([Me-Py]⁺) vs methyl-picolinium ([Me-3-Pic]⁺)) also reduce cation-phenol COM interaction lengths consistent with small increases in extraction efficiency for the same ionic liquids.

Original language	English
Pages (from-to)	10219-20226
Number of pages	8
Journal	Physical Chemistry Chemical Physics (PCCP)
Volume	22
Issue number	18
DOIs	https://doi.org/10.1039/D0CP01013H
Publication status	Published - 08 Apr 2020

Keywords

ionic liquids
phenol extraction
Neutron Scattering

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry

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10.1039/D0CP01013HLicence: Unspecified

Enhanced Extraction of Phenol from Model Oils Using Ionic Liquids Elucidated with Neutron Diffraction
Copyright 2020 RSC. This work is made available online in accordance with the publisher’s policies. Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 2.61 MBLicence: Unspecified

Designing functional liquids
Byrne, E. (Author), Swadzba-Kwasny, M. (Supervisor) & Holbrey, J. (Supervisor), Dec 2021
Student thesis: Doctoral Thesis › Doctor of Philosophy

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11 Citations
1 Article

Phenol recovery from aromatic-rich oils by formation of eutectic liquids with trialkyl-2,3-dihydroxypropylammonium chloride salts
Holbrey, J. & Byrne, E., 09 Jun 2020, In: Sustainable Chemistry. 1, 1, p. 49-61 13 p.
Research output: Contribution to journal › Article › peer-review

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7 Citations (Scopus)

161 Downloads (Pure)

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title = "Enhanced Extraction of Phenol from Model Oils Using Ionic Liquids Elucidated with Neutron Diffraction",

abstract = "Aromatic cation ionic liquids (ILs) based on alkylpyridiniums are shown to be good phenol extractants from model oils (hexane/toluene). ILs with hard basic anions are found to have best extraction efficiency consistent with tetraalkylammonium salts ([NR4]X). Key extraction interactions were analysed using small angle neutron diffraction. Trifluoromethanesulfonate ([OTf]- or triflate) anions provide the synergistic effects of reduced cation-phenol centre of mass (COM) distances and increased hydrogen bonding that are linked to the improved extraction efficiency. Increases in cation electron density (methyl-pyridinium ([Me-Py]+) vs methyl-picolinium ([Me-3-Pic]+)) also reduce cation-phenol COM interaction lengths consistent with small increases in extraction efficiency for the same ionic liquids.",

keywords = "ionic liquids, phenol extraction, Neutron Scattering",

author = "Turner, \{Adam H.\} and Byrne, \{Emily L.\} and Thaise Pereira and Holbrey, \{John D.\}",

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doi = "10.1039/D0CP01013H",

language = "English",

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pages = "10219--20226",

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publisher = "Royal Society of Chemistry",

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T1 - Enhanced Extraction of Phenol from Model Oils Using Ionic Liquids Elucidated with Neutron Diffraction

AU - Turner, Adam H.

AU - Byrne, Emily L.

AU - Pereira, Thaise

AU - Holbrey, John D.

PY - 2020/4/8

Y1 - 2020/4/8

N2 - Aromatic cation ionic liquids (ILs) based on alkylpyridiniums are shown to be good phenol extractants from model oils (hexane/toluene). ILs with hard basic anions are found to have best extraction efficiency consistent with tetraalkylammonium salts ([NR4]X). Key extraction interactions were analysed using small angle neutron diffraction. Trifluoromethanesulfonate ([OTf]- or triflate) anions provide the synergistic effects of reduced cation-phenol centre of mass (COM) distances and increased hydrogen bonding that are linked to the improved extraction efficiency. Increases in cation electron density (methyl-pyridinium ([Me-Py]+) vs methyl-picolinium ([Me-3-Pic]+)) also reduce cation-phenol COM interaction lengths consistent with small increases in extraction efficiency for the same ionic liquids.

AB - Aromatic cation ionic liquids (ILs) based on alkylpyridiniums are shown to be good phenol extractants from model oils (hexane/toluene). ILs with hard basic anions are found to have best extraction efficiency consistent with tetraalkylammonium salts ([NR4]X). Key extraction interactions were analysed using small angle neutron diffraction. Trifluoromethanesulfonate ([OTf]- or triflate) anions provide the synergistic effects of reduced cation-phenol centre of mass (COM) distances and increased hydrogen bonding that are linked to the improved extraction efficiency. Increases in cation electron density (methyl-pyridinium ([Me-Py]+) vs methyl-picolinium ([Me-3-Pic]+)) also reduce cation-phenol COM interaction lengths consistent with small increases in extraction efficiency for the same ionic liquids.

KW - ionic liquids

KW - phenol extraction

KW - Neutron Scattering

U2 - 10.1039/D0CP01013H

DO - 10.1039/D0CP01013H

M3 - Article

SN - 1463-9076

VL - 22

SP - 10219

EP - 20226

JO - Physical Chemistry Chemical Physics (PCCP)

JF - Physical Chemistry Chemical Physics (PCCP)

IS - 18

ER -

Enhanced Extraction of Phenol from Model Oils Using Ionic Liquids Elucidated with Neutron Diffraction

Abstract

Keywords

ASJC Scopus subject areas

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Student theses

Designing functional liquids

Research output

Phenol recovery from aromatic-rich oils by formation of eutectic liquids with trialkyl-2,3-dihydroxypropylammonium chloride salts

Cite this