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Title: Elucidating the Role of Hydrogen Bond Donor and Acceptor on Solvation in Deep Eutectic Solvents Formed by Ammonium/Phosphonium Salts and Carboxylic Acids

Abstract

Deep eutectic solvents (DESs) constitute a rapidly emerging class of sustainable liquids that have been widely studied and employed in chemical separations, catalysis, and electrochemistry. The unique physicochemical and solvation properties of DESs can be highly tailored by choosing the appropriate hydrogen bond acceptor (HBA) and hydrogen bond donor (HBD). Understanding the role of the HBA and HBD on the multiple solvation interactions in DESs is important to enable their judicious selection for particular applications. As such, this work constitutes the first study to exploit chromatography to measure solute–solvent interactions of DESs using a wide array of known probe molecules. The constituent components of 20 DESs, formed by ammonium and phosphonium-based salts and carboxylic acids, are systematically modulated to delineate the contribution of the HBA and HBD toward individual solvation properties. Solute–solvent interactions measured in this study are used to interpret and explain the performance of DESs in desulfurization of fuels and extraction of natural products. The results from this study can be used to predict and understand the performance of DESs in various chemical processes where solvation interactions heavily influence outcomes.

Authors:
 [1];  [2];  [1]; ORCiD logo [1]
+ Show Author Affiliations
  1. Ames Lab., Ames, IA (United States); Iowa State Univ., Ames, IA (United States)
  2. Iowa State Univ., Ames, IA (United States)
Publication Date:
Research Org.:
Ames Lab., Ames, IA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division
OSTI Identifier:
1735717
Report Number(s):
IS-J-10,370
Journal ID: ISSN 2168-0485
Grant/Contract Number:  
AC02-07CH11358
Resource Type:
Accepted Manuscript
Journal Name:
ACS Sustainable Chemistry & Engineering
Additional Journal Information:
Journal Volume: 8; Journal Issue: 49; Journal ID: ISSN 2168-0485
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; solvation interactions; gas chromatography; separations; extractions; green solvents; desulfurization; natural products

Citation Formats

Farooq, Muhammad Qamar, Odugbesi, Gabriel A., Abbasi, Nabeel Mujtaba, and Anderson, Jared L. Elucidating the Role of Hydrogen Bond Donor and Acceptor on Solvation in Deep Eutectic Solvents Formed by Ammonium/Phosphonium Salts and Carboxylic Acids. United States: N. p., 2020. Web. doi:10.1021/acssuschemeng.0c06926.
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Farooq, Muhammad Qamar, Odugbesi, Gabriel A., Abbasi, Nabeel Mujtaba, & Anderson, Jared L. Elucidating the Role of Hydrogen Bond Donor and Acceptor on Solvation in Deep Eutectic Solvents Formed by Ammonium/Phosphonium Salts and Carboxylic Acids. United States. https://doi.org/10.1021/acssuschemeng.0c06926
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Farooq, Muhammad Qamar, Odugbesi, Gabriel A., Abbasi, Nabeel Mujtaba, and Anderson, Jared L. Mon . "Elucidating the Role of Hydrogen Bond Donor and Acceptor on Solvation in Deep Eutectic Solvents Formed by Ammonium/Phosphonium Salts and Carboxylic Acids". United States. https://doi.org/10.1021/acssuschemeng.0c06926. https://www.osti.gov/servlets/purl/1735717.
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@article{osti_1735717,
title = {Elucidating the Role of Hydrogen Bond Donor and Acceptor on Solvation in Deep Eutectic Solvents Formed by Ammonium/Phosphonium Salts and Carboxylic Acids},
author = {Farooq, Muhammad Qamar and Odugbesi, Gabriel A. and Abbasi, Nabeel Mujtaba and Anderson, Jared L.},
abstractNote = {Deep eutectic solvents (DESs) constitute a rapidly emerging class of sustainable liquids that have been widely studied and employed in chemical separations, catalysis, and electrochemistry. The unique physicochemical and solvation properties of DESs can be highly tailored by choosing the appropriate hydrogen bond acceptor (HBA) and hydrogen bond donor (HBD). Understanding the role of the HBA and HBD on the multiple solvation interactions in DESs is important to enable their judicious selection for particular applications. As such, this work constitutes the first study to exploit chromatography to measure solute–solvent interactions of DESs using a wide array of known probe molecules. The constituent components of 20 DESs, formed by ammonium and phosphonium-based salts and carboxylic acids, are systematically modulated to delineate the contribution of the HBA and HBD toward individual solvation properties. Solute–solvent interactions measured in this study are used to interpret and explain the performance of DESs in desulfurization of fuels and extraction of natural products. The results from this study can be used to predict and understand the performance of DESs in various chemical processes where solvation interactions heavily influence outcomes.},
doi = {10.1021/acssuschemeng.0c06926},
journal = {ACS Sustainable Chemistry & Engineering},
number = 49,
volume = 8,
place = {United States},
year = {Mon Nov 30 00:00:00 EST 2020},
month = {Mon Nov 30 00:00:00 EST 2020}
}
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Journal Article:
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Publisher's Version of Record
https://doi.org/10.1021/acssuschemeng.0c06926
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Works referenced in this record:

Deep Eutectic Solvents Formed between Choline Chloride and Carboxylic Acids:  Versatile Alternatives to Ionic Liquids
journal, July 2004

  • Abbott, Andrew P.; Boothby, David; Capper, Glen
  • Journal of the American Chemical Society, Vol. 126, Issue 29
  • DOI: 10.1021/ja048266j

Deep Eutectic Solvents (DESs) and Their Applications
journal, October 2014

  • Smith, Emma L.; Abbott, Andrew P.; Ryder, Karl S.
  • Chemical Reviews, Vol. 114, Issue 21
  • DOI: 10.1021/cr300162p

Quantification of the liquid window of deep eutectic solvents
journal, January 2018

  • Kollau, Laura J. B. M.; Vis, Mark; van den Bruinhorst, Adriaan
  • Chemical Communications, Vol. 54, Issue 95
  • DOI: 10.1039/C8CC05815F

Quest for Green‐Solvent Design: From Hydrophilic to Hydrophobic (Deep) Eutectic Solvents
journal, April 2019

  • Florindo, Catarina; Branco, Luís C.; Marrucho, Isabel M.
  • ChemSusChem, Vol. 12, Issue 8
  • DOI: 10.1002/cssc.201900147

Natural Deep Eutectic Solvents – Solvents for the 21st Century
journal, March 2014

  • Paiva, Alexandre; Craveiro, Rita; Aroso, Ivo
  • ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 5
  • DOI: 10.1021/sc500096j

Natural deep eutectic solvents as new potential media for green technology
journal, March 2013

p -Toluenesulfonic Acid-Based Deep-Eutectic Solvents for Solubilizing Metal Oxides
journal, January 2019

  • Rodriguez Rodriguez, Nerea; Machiels, Lieven; Binnemans, Koen
  • ACS Sustainable Chemistry & Engineering, Vol. 7, Issue 4
  • DOI: 10.1021/acssuschemeng.8b05072

Deep Eutectic Solvents as Efficient Solvents in Biocatalysis
journal, September 2019

Effect of deep eutectic solvent mixtures on lipase activity and stability
journal, June 2016

Dihydrogen-bonding deep eutectic solvents as reaction media for lipase-catalyzed transesterification
journal, February 2019

Carbon Dioxide Solubilities in Decanoic Acid-Based Hydrophobic Deep Eutectic Solvents
journal, March 2018

  • Zubeir, Lawien F.; van Osch, Dannie J. G. P.; Rocha, Marisa A. A.
  • Journal of Chemical & Engineering Data, Vol. 63, Issue 4
  • DOI: 10.1021/acs.jced.7b00534

Intermolecular interactions upon carbon dioxide capture in deep-eutectic solvents
journal, January 2018

  • Shukla, Shashi Kant; Mikkola, Jyri-Pekka
  • Physical Chemistry Chemical Physics, Vol. 20, Issue 38
  • DOI: 10.1039/C8CP03724H

Application of deep eutectic solvents as catalysts for the esterification of oleic acid with glycerol
journal, December 2017

Glycerol eutectics as sustainable solvent systems
journal, January 2011

  • Abbott, Andrew P.; Harris, Robert C.; Ryder, Karl S.
  • Green Chem., Vol. 13, Issue 1
  • DOI: 10.1039/C0GC00395F

A novel phosphonium-based deep eutectic catalyst for biodiesel production from industrial low grade crude palm oil
journal, April 2013

110th Anniversary: Distribution Coefficients of Furfural and 5-Hydroxymethylfurfural in Hydrophobic Deep Eutectic Solvent + Water Systems: Experiments and Perturbed-Chain Statistical Associating Fluid Theory Predictions
journal, February 2019

  • Dietz, Carin H. J. T.; Gallucci, Fausto; van Sint Annaland, Martin
  • Industrial & Engineering Chemistry Research, Vol. 58, Issue 10
  • DOI: 10.1021/acs.iecr.8b06234

Extraction desulfurization process of fuels with ammonium-based deep eutectic solvents
journal, January 2013

  • Li, Changping; Li, Dan; Zou, Shuangshuang
  • Green Chemistry, Vol. 15, Issue 10
  • DOI: 10.1039/c3gc41067f

Green Carboxylic Acid-Based Deep Eutectic Solvents as Solvents for Extractive Desulfurization
journal, June 2016

Theoretical Study of Oil Desulfuration by Ammonium-Based Deep Eutectic Solvents
journal, June 2018

Tunable Hydrophobic Eutectic Solvents Based on Terpenes and Monocarboxylic Acids
journal, May 2018

  • Martins, Mónia A. R.; Crespo, Emanuel A.; Pontes, Paula V. A.
  • ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 7
  • DOI: 10.1021/acssuschemeng.8b01203

Properties and thermal behavior of natural deep eutectic solvents
journal, March 2016

Role of Hydrophilic Ammonium-Based Deep Eutectic Solvents in SO 2 Absorption
journal, October 2019

Deep eutectic solvents: overcoming 21st century challenges
journal, August 2019

  • Florindo, Catarina; Lima, Filipa; Ribeiro, Bernardo Dias
  • Current Opinion in Green and Sustainable Chemistry, Vol. 18
  • DOI: 10.1016/j.cogsc.2018.12.003

How polar are choline chloride-based deep eutectic solvents?
journal, January 2014

  • Pandey, Ashish; Rai, Rewa; Pal, Mahi
  • Phys. Chem. Chem. Phys., Vol. 16, Issue 4
  • DOI: 10.1039/C3CP53456A

Solvatochromic parameters of deep eutectic solvents formed by ammonium-based salts and carboxylic acids
journal, September 2017

A closer look into deep eutectic solvents: exploring intermolecular interactions using solvatochromic probes
journal, January 2018

  • Florindo, C.; McIntosh, A. J. S.; Welton, T.
  • Physical Chemistry Chemical Physics, Vol. 20, Issue 1
  • DOI: 10.1039/C7CP06471C

Application of Deep Eutectic Solvents (DES) for Phenolic Compounds Extraction: Overview, Challenges, and Opportunities
journal, April 2017

  • Ruesgas-Ramón, Mariana; Figueroa-Espinoza, Maria Cruz; Durand, Erwann
  • Journal of Agricultural and Food Chemistry, Vol. 65, Issue 18
  • DOI: 10.1021/acs.jafc.7b01054

Solvatochromic Probe Behavior within Choline Chloride-Based Deep Eutectic Solvents: Effect of Temperature and Water
journal, December 2014

  • Pandey, Ashish; Pandey, Siddharth
  • The Journal of Physical Chemistry B, Vol. 118, Issue 50
  • DOI: 10.1021/jp510420h

Hybrid green nonaqueous media: tetraethylene glycol modifies the properties of a (choline chloride + urea) deep eutectic solvent
journal, January 2016

  • Kadyan, Anu; Behera, Kamalakanta; Pandey, Siddharth
  • RSC Advances, Vol. 6, Issue 36
  • DOI: 10.1039/C6RA03726G

Synthesis of a Novel Allyl-Functionalized Deep Eutectic Solvent to Promote Dissolution of Cellulose
journal, August 2016

Solvatochromic Parameters of Deep Eutectic Solvents: Effect of Different Carboxylic Acids as Hydrogen Bond Donor
journal, October 2019

  • Dwamena, Amos K.; Raynie, Douglas E.
  • Journal of Chemical & Engineering Data, Vol. 65, Issue 2
  • DOI: 10.1021/acs.jced.9b00872

Metal-Free Deep Eutectic Solvents: Preparation, Physical Properties, and Significance
journal, November 2019

  • Gurkan, Burcu; Squire, Henry; Pentzer, Emily
  • The Journal of Physical Chemistry Letters, Vol. 10, Issue 24
  • DOI: 10.1021/acs.jpclett.9b01980

Deep Eutectic Solvents as Efficient Media for the Extraction and Recovery of Cynaropicrin from Cynara cardunculus L. Leaves
journal, October 2017

  • de Faria, Emanuelle; do Carmo, Rafael; Cláudio, Ana Filipa
  • International Journal of Molecular Sciences, Vol. 18, Issue 11
  • DOI: 10.3390/ijms18112276

Scales of solute hydrogen-bonding: their construction and application to physicochemical and biochemical processes
journal, January 1993

Hydrogen bonding. Part 34. The factors that influence the solubility of gases and vapours in water at 298 K, and a new method for its determination
journal, January 1994

  • Abraham, Michael H.; Andonian-Haftvan, Jenik; Whiting, Gary S.
  • Journal of the Chemical Society, Perkin Transactions 2, Issue 8
  • DOI: 10.1039/p29940001777

Characterizing Ionic Liquids On the Basis of Multiple Solvation Interactions
journal, November 2002

  • Anderson, Jared L.; Ding, Jie; Welton, Thomas
  • Journal of the American Chemical Society, Vol. 124, Issue 47
  • DOI: 10.1021/ja028156h

Chemometric evaluation of the solvent properties of liquid organic salts
journal, January 1995

Characterization of Some GLC Chiral Stationary Phases:  LFER Analysis
journal, February 1997

Evaluation of fatty acid/alcohol-based hydrophobic deep eutectic solvents as media for extracting antibiotics from environmental water
journal, September 2018

  • Tang, Weiyang; Dai, Yunliang; Row, Kyung Ho
  • Analytical and Bioanalytical Chemistry, Vol. 410, Issue 28
  • DOI: 10.1007/s00216-018-1346-6

Efficient and Selective Extraction of 99m TcO 4 – from Aqueous Media Using Hydrophobic Deep Eutectic Solvents
journal, October 2018

  • Phelps, Tim E.; Bhawawet, Nakara; Jurisson, Silvia S.
  • ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 11
  • DOI: 10.1021/acssuschemeng.8b03950

A Static Coating Procedure for Glass Capillary Columns
journal, October 1968

Solvent–solute interactions in ionic liquids
journal, January 2003

  • Crowhurst, Lorna; Mawdsley, Philip R.; Perez-Arlandis, Juan M.
  • Phys. Chem. Chem. Phys., Vol. 5, Issue 13
  • DOI: 10.1039/B303095D

Characterization of phosphonium ionic liquids through a linear solvation energy relationship and their use as GLC stationary phases
journal, February 2008

  • Breitbach, Zachary S.; Armstrong, Daniel W.
  • Analytical and Bioanalytical Chemistry, Vol. 390, Issue 6
  • DOI: 10.1007/s00216-008-1877-3

Enhanced stabilization of the Tobacco mosaic virus using protic ionic liquids
journal, January 2012

  • Byrne, Nolene; Rodoni, Brendan; Constable, Fiona
  • Physical Chemistry Chemical Physics, Vol. 14, Issue 29
  • DOI: 10.1039/c2cp41625e

Natural Deep Eutectic Solvents as a New Extraction Media for Phenolic Metabolites in Carthamus tinctorius L.
journal, June 2013

  • Dai, Yuntao; Witkamp, Geert-Jan; Verpoorte, Robert
  • Analytical Chemistry, Vol. 85, Issue 13
  • DOI: 10.1021/ac400432p

A simple and cost-effective extractive desulfurization process with novel deep eutectic solvents
journal, January 2016

  • Wang, Xin; Jiang, Wei; Zhu, Wenshuai
  • RSC Advances, Vol. 6, Issue 36
  • DOI: 10.1039/C5RA27266A

Cynaropicrin: A Comprehensive Research Review and Therapeutic Potential As an Anti-Hepatitis C Virus Agent
journal, December 2016

  • Elsebai, Mahmoud F.; Mocan, Andrei; Atanasov, Atanas G.
  • Frontiers in Pharmacology, Vol. 7
  • DOI: 10.3389/fphar.2016.00472

Palladium catalysed hydroxycarbonylation of 1-phenylethanol in molten salt media
journal, June 2006

  • Lapidus, Albert; Eliseev, Oleg; Bondarenko, Tatyana
  • Journal of Molecular Catalysis A: Chemical, Vol. 252, Issue 1-2
  • DOI: 10.1016/j.molcata.2006.02.061

Notes. Salt Effects in the Solvolysis of Benzhydryl Chloride
journal, February 1961

  • McMichael, Kirk; Clement, Robert
  • The Journal of Organic Chemistry, Vol. 26, Issue 2
  • DOI: 10.1021/jo01061a622
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