Department of

Computational Biological Chemistry

COST CM1206: "Exchange on ionic liquids"

Working group 2

Working group 2 works on the determination of physico-chemical properties from experiments and computer simulations. We are also interested in IL mixtures with other ionic liquids and neutral co-solvents as well as the behaviour of these pure IL and mixtures at the surface of solutes, electrodes, etc.


Leaders:

  • Christian Schröder (University of Vienna, Austria)
  • Margarida Costa-Gomes (CNRS Clermont-Ferrand, France)


The central objectives of Working group 2 are:

Determination of properties of IL/co-solvent mixtures

Viscous ionic liquids benefit from the mixture with more fluid co-solvents. Furthermore, new nanostructures like micelles and reversed micelles offer new possibilities to perform chemical reaction or processes which are not possible with pure ionic liquids. However, a detailed understanding of the solvation process and the mutual interactions between the solvent molecules is a prerequisite to design adequate mixtures showing desirable properties.

Peer-reviewed results (COST CM1206 members are in bold):

Acetic acid extraction from water using nature-based hydrophobic ionic liquids
M. A. A. Rocha, N. R. Rodríguez, W. Schröer, B. Rathke, M. C. Kroon
Chemical Engineering Science (2017), in preparation
Alternative probe for the determination of the hydrogen-bond acidity of ionic liquids and their aqueous solutions
Pedro P. Madeira, Helena Passos, Joana Gomes, João A. P. Coutinho and Mara G. Freire
Phys. Chem. Chem. Phys. (2017), submitted
Physicochemical properties of fatty acid based ionic liquids
M.A.R. Martins, J.A.P. Coutinho, S.P. Pinho, U. Domanska
J. Chem. Thermodyn. submitted
Enhancement of energy storage efficiency in double layer capacitors by tuning the composition of ionic liquids mixtures
Renata Costa, Iuliia V Voroshylova, M. Natália, D. S. Cordeiro, Carlos M. Pereira, A. Fernando Silva
Electrochimica Acta (2017), submitted
Solvatochromic parameters of deep eutectic solvents formed by ammonium-based salts and carboxylic acids
Ana Rita R. Teles, Emanuel V. Capela, Rafael S. Carmo, João A. P. Coutinho, Armando J. D. Silvestre and Mara G. Freire
Fluid Phase Equilibria (2017), accepted
Thermophysical characterization of ionic liquids based on the perfluorobutanesulfonate anion: experimental and soft-SAFT modelling results
Ana B. Pereiro, Felix Llovell, Joao M. M. Araujo, Andreia S. S. Santos, Luis P. N. Rebelo, Manuel M. Pineiro and L. F. Vega
Chem. Phys. Chem. (2017), DOI: 10.1002/cphc.201700327
Experimental and Theoretical Thermodynamic Study of Distillable Ionic Liquid 1,5-Diazabicyclo[4.3.0]non-5-enium Acetate
A. Ostonen, J. Bervas, P. Uusi-Kyyny, V. Alopaeus, D. H. Zaitsau, V. N. Emel'Yanenko, C. Schick, A. W. T. King, J. Helminen, I. Kilpeläinen, A. A. Khachatrian, M. A. Varfolomeev, S. P. Verevkin
Industrial and Engineering Chemistry Research 55 (2016), 10445
Physicochemical properties of fatty acid based ionic liquids
M. A. A. Rocha, A. van den Bruinhorst, W. Schröer, B. Rathke, M. C. Kroon
J. Chem. Thermodyn. (2016), 100, 156-164
Liquid-liquid equilibria in aqueous 1-alykl-3-methylimidazolium and 1-butyl-3-ethylimidazolium based ionic liquids
A. Dimitrijevic, T. Trtic-Petrovic, M. Vranes, S. Papovic, A. Tot, S. Dozic, S. Gadzuric
J. Chem. Eng. Data, (2016), 61, 549
Properties modification by eutectic formation in mixtures of ionic liquids
Olga Stolarska, Ana Soto, Héctor Rodríguez, Marcin Smiglak
RSC Advances (2015), 5:22178
Measurement and PC-SAFT modelling of three-phase behaviour
I. Rodriguez-Palmeiro, O. Rodriguez, A. Soto, C. Held
Phys. Chem. Chem. Phys. (2015) 17:1800
Measurements of Activity Coefficients at Infinite Dilution of Organic Solutes and Water on Polar Imidazolium-Based Ionic Liquids
Mónia A. R. Martins, João A. P. Coutinho, Simão P. Pinho, Urszula Domanska
Journal of Chemical Thermodynamics (2015) 91:194
Correlation and prediction of dense fluid transport coefficients. IX. Ionic liquids
F. M. Gacino, M.J.P. Comunas, J. Fernandez, S. K. Mylona, M. J. Assael
Int. J. Thermophys. (2014), 25: 812

Conference proceedings:

Thermodynamic Characterization of Fluorinated Ionic Liquids to be used as Artificial Oxygen Carriers Ana B. Pereiro, Margarida L. Ferreira, Felix Llovell, Joao M. M. Araujo, Luis Paulo N. Rebelo, Manuel M. Pineiro, Lourdes F. Vega
16th European Meeting on Supercritical Fluids, EMSF 2017, Lisbon (Portugal) page 184, ISSN/ISBN: 978-989-20-7507-5
Solubility of Respiratory Gases in Fluorinated Ionic Liquids Ana B. Pereiro, Margarida L. Ferreira, João M. M. Araujo, Luis Paulo N. Rebelo, Lourdes F. Vega and Felix Llovell
26th EUCHEM Conference on Molten Salts and Ionic Liquids 2016, Vienna (Austria) 141-OP-73, ISSN/ISBN: 978-3-9504017-4-5
Fine-Tuning of Phase and Self-Aggregation Behaviour of Fluorinated Ionic Liquids in Aqueous Solutions Ana B. Pereiro, Felix Llovell, Joao M. M. Araujo, Luis Paulo N. Rebelo, Manuel M. Pineiro and Lourdes F. Vega
PPEPPD 2016 - 14th International Conference on Properties and Phase Equilibria for Product and Process Design, Porto (Portugal) P69, ISSN/ISBN: 978-989-20-6695-0
Theoretical-Experimental Study of Aqueous Fluorinated Ionic Liquids Felix Llovell, Ana B. Pereiro, Joao M. M. Araujo, Luis Paulo N. Rebelo, Manuel M. Pineiro, Lourdes F. Vega
Iberoamerican Meeting on Ionic Liquids- IMIL 2015, Madrid (Spain) page 117, ISSN/ISBN: 978-84-606-8652-1

Short term missions

Darius YeadonInteraction between Ionic Liquids and Water
Alberto RiveraDynamics of ionic liquids by solvation and photon correlation spectroscopy
Felix Marino GacinoViscosimetric characterisation of ionic liquids at high pressures
Isabel Vazquez FernandezStructure and bonding of pure protic ionic liquids and their mixtures
Olatunde JogunolaEstimation of thermodynamic properties of novel ionic liquids and ionc liquid related reactions
Sofia MylonaLight scattering investigation of protic ionic liquid alkanol mixtures
Marisa Alves da RochaPhase behaviour of mixtures of nature based ionic liquids with volatile fatty acids
Hector Rodriguez MartinezThermal analyses of eutectic mixtures of ionic liquids
Alexandr OstonenNovel vapor pressure and ethalpy of vaporization measurement methods for ionic liquids
David PatinhaStrategies to obtain polymeric ionic liquids for high temperature applications
Felix LlovellPhase behaviour of selected fluorinated ionic liquids in aqueous solutions.
Marcus StuckenholzVapor liquid equilibrium of mixtures of ionic liquids with volatile solvent
Nebojsa ZecThermodynamic properties of dicyanamide based ionic liquids with molecular solvents.
Renato TomasStudies of molecular interactions of some imidazolium chloride ionic liquds in water by viscometric and volumetric measurements at different temperatures



Modelling of ILs and mixtures

Existing non-polarizable force field on ionic liquids resulted in retarded dynamics compared to experimental data. Currently, most non-polarizable simulations use reduced partial charges to work around this problem. On the one hand, the dynamics of the simulation is accelerated (and may match experimental data) but inherent features of liquids, e.g. hydrogen bonding, are more or less completely shut down. Furthermore, force fields including partial charge scaling are not transferable anymore, since each combination of cations and anions has its own scaling factor. Consequently, exchanging cations or anions result in a different scaling factor which necessitates in principle a reparametrization of all other force field parameters.

Therefore, we will combine the expertise of various computational groups within CM1206 to develop a transferable, polarizable force field based on the non-polarizable force field of Canongia Lopes and Padua. In the upcoming budget period a new research action “Conversion of force fields” will deal with the harmonization and exchange of existing force fields on a XML basis. In this context, we will also develop a guideline of “good practise in (polarizable) simulations”.

First efforts for a polarizable force field have also been undertaken in our research action “Electrostatics in ionic liquids and their mixtures”. Here, we plan several STSM to transfer the knowledge and extend the current database to new ionic liquid compounds. Last budget period we already applied for several H2020 calls including industrial partners. These efforts will be intensified for the upcoming budget year. For further information please contact Prof. Varela.

Furthermore, we plan to initiate a new research call “Mixtures of protic ionic liquids in various solvents”. Here, the mechanism of charge transport and the correlation of charge transfer and polarizability will be major issues.


Software acknowledging COST CM1206:

ForConX
converts (polarizable) force field fiels between AMBER, CHARMM, DLPOLY, GROMACS and LAMMPS. Developed during the short term mission V. Lesch.

Peer-reviewed results:

Influence of the Alkyl Side Chain Length on the Thermophysical Properties of Chiral Ionic Liquids with a (1R,2S,5R)-(–)-Menthol Substituent and Data Treatment by Means of Mathematical Gnostics
A. Andresova, M. Bendova, Z. Wagner, J. Schwarz, J. Feder-Kubis J. Mol. Liq. accepted
ForConX: A forcefield conversion tool based on XML
V. Lesch, D. Diddens, C. E. S. Bernardes, B. Golub, A. Dequidt, V. Zeindlhofer, M. Sega, C. Schröder
J. Comp. Chem. (2017) 38:629
Molecular dynamics simulation of the behaviour of water in nano-confined ionic liquid–water mixtures
B. Docampo-Álvarez, V. Gómez-González, H. Montes-Campos, J. M. Otero-Mato, T. Méndez-Morales, O. Cabeza, L. J. Gallego, R. M. Lynden-Bell, V. B. Ivaništšev, M. V. Fedorov, L. M. Varela
J. Phys.: Condens. Matter. (2016), 28, 464001
Interactions in the ionic liquid [EMIM][FAP]: a coupled experimental and computational analysis
I.V. Voroshylova, F. Teixeira, R. Costa, C.M. Pereira, M.N.D.S. Cordeiro
Phys. Chem. Chem. Phys, 18, 2617-2628 (2016)
Capacitance of Nanoporous Carbon-Based Supercapacitors Is a Trade-Off between the Concentration and the Separability of the Ions
R. Burt, K. Breitsprecher, B. Daffos, P.-L. Taverna, P. Simon, G. Birkett, X. S. Zhao, C. Holm and M. Salanne
J. Phys. Chem. Lett. (2016) 7:4015
Additive polarizabilities in ionic liquids
C.E.S. Bernardes, K. Shimizu, J. N. Canongia Lopes, P. Marquetand, E. Heid, O. Steinhauser, C. Schröder
Phys. Chem. Chem. Phys. (2016) 18:1665
Improved Force Field Model for the Deep Eutectic Solvent Ethaline: Reliable Physicochemical Properties
E.S. Ferreira, I.V. Voroshylova, C.M. Pereira, M.N.D.S. Cordeiro
J. Phys. Chem. B, 120 (38), pp 10124–10137 (2016)
Comparing induced point-dipoles and Drude oscillators
M. Schmollngruber, V. Lesch, C. Schroeder, A. Heuer, O. Steinhauser
Phys. Chem. Chem. Phys. (2015) 17:14297
Thermal Properties of Alkyl-triethylammonium bis(trifluoromethyl)sulfonylimide Ionic Liquids
K. Machanová, Z. Wagner, A. Andresová, J. Rotrekl, A. Boisset, J. Jacquemin, M. Bendová
J. Solution Chemistry (2015) 44:790
Association in ethylammonium nitrate-dimethyl sulfoxide mixtures: First structural and dynamical evidences
O. Russina, M. Macchiagodena, B. Kirchner, A. Mariani, B. Aoun, M. Russina, R. Caminiti, A. Triolo
J. non-crystalline solids (2015) 407:333
Domain Analysis in Nanostructured Liquids: A Post-Molecular Dynamics Study at the Example of Ionic Liquids
M. Brehm, H. Weber, M. Thomas, O. Holluczki, B. Kirchner
Chem. Phys. Chem. (2015) 16:3271
Triphilic Ionic-Liquid Mixtures: Fluorinated and Non-fluorinated Aprotic Ionic-Liquid Mixtures
O. Holloczki, M. Macchiagodena, H. Weber, M. Thomas, M. Brehm, A. Stark, O. Russina, A. Triolo, B. Kirchner
Chem. Phys. Chem. (2015) 16:3325

Short term missions

Iris Sancho SanzFormation of different frustated Lewis pairs within ionic liquids. Energetical study and molecular dynamics simulations
Daniel Moreno FernandezA COSMO-based study of properties and applications of zwitterions compared with traditional ionic liquids
Meeri LembinenMD simulations of ionic liquid mixtures with polarizable force fields
Benjamin GolubProtic Ionic Liquids: Polarizable Force Fields and Proton Transfer
Paulo SerraEffect of branched alcohols on the phase behaviour of imidazolium-based ionic liquids
Alain DequidtHeterogeneous dynamics of ionic liquids studied with polarizable molecular dynamics simulations
Volker LeschHow to bring induced point-dipoles and Drude oscillators together for ionic liquids
Marina MacchiagodenaInvestigation of the structure of ethylammonium nitrate-dimethylsulfoxide mixtures
Christian SchröderPolarisabilities in ionic liquids
Borja DocampoKinetic depolarization of aqueous ionic liquid mixtures
Konrad BreitsprecherElectrode models for confined ionic liquids
Iris Sancho SanzTrispentafluorophenyl borane in trihexyltetradecylphosphonium chloride. Do FLP systems build up among ionic liquids?
Iago Rodriguez PalmeiroAutomated MD simulations of ionic liquid properties at charged interfaces
Vladislav IvanistsevAutomated MD simulations of ionic liquid properties at charged interfaces
Alexandr OstonenNovel vapor pressure and enthalpy of vaporization measurement methods for ionic liquids
Aleksandr TotExperimental and computational study of newly synthesized ether and hydroxyl functionalized ILs



Interactions between ionic liquids and solutes and structures at interfaces

Although pure ionic liquids are an interesting material to study, true applications always involve the contact with solutes, electrodes, nano-materials or surfaces. Within our research action “Electrostatics in ionic liquids and their mixtures” several ionic liquids are tested to improve the electrochemical behavior of ionic liquids at certain electrodes.

In addition to experiments, computational methods to model the surface potentials are developed. In a joint workshop “Interfaces of ionic liquids” of working group 2 and 3 in Belek from Oct 3rd-5th 2015, experimenter and theoreticians discussed and reported their recent findings of particular ionic liquids at interfaces to other materials.

Peer-reviewed results:

Dual functionality of amphiphilic 1-alykl-3-methylimidazolium hydrogen sulfate ionic liquids: surfactants with catalytic function
J. Nowicki, J. Luczak, D. Staczyk RSC Advances submitted
Molecular dynamics simulation of the structure and interfacial free energy barriers of mixtures of ionic liquids and divalent salts near a graphene wall
V. Gómez-González, B. Docampo-Álvarez, T. Méndez-Morales, O. Cabeza, V. B. Ivaništšev, M. V. Fedorov, L. J. Gallego, L. M. Varela
Phys. Chem. Chem. Phys. (2017), 19, 846
Role of the anion on the Interfacial Structure of Ionic Liquids Binary Mixtures at Mercury Interfaces
Renata Costa, Carlos M. Pereira, A. Fernando Silva
Electrochimica Acta (2016), 195, 150
Molecular origin of high free energy barriers for alkali metal ion transfer through ionic liquid-graphene electrode interfaces
V. Ivanistsev, T. Mendez-Morales, R. M. Lynden-Bell, O. Cabeza, L. J. Gallego, L. M. Varela, M. Fedorov
Phys. Chem. Chem. Phys. (2016) 18:1302
Selection of Ionic Liquids to be used as Separation Agents for Terpenes and Terpenoids
M.A.R. Martins, U. Domanska, B. Schröder, J.A.P. Coutinho, S.P. Pinho
ACS Sustainable Chemistry & Engineering (2016), 4, 548
Enhanced extraction of proteins using cholinium-based ionic liquids as phase-forming components of aqueous biphasic systems
M. V. Quental, M. Caban, M. M. Pereira, P. Stepnowski, J.A.P. Coutinho, M.G. Freire
Biotechnology Journal (2015) 19:1457
Measurements of Activity Coefficients at Infinite Dilution of Organic Solutes and Water on Polar Imidazolium-Based Ionic Liquids
M.A.R. Martins, J.A.P. Coutinho, S.P. Pinho, U. Domanska
J. Chem. Thermodyn. (2015) 91:194
Absorption of Flue-Gas components by ionic liquids
H. Kolding, P- Thomassen, S. Mossin, S. Kegnaes, A. Riisager, J. Rogez, G. Mikaelian, R. Fehrmann
ECS Transactions (2014) 64:97
Ionic Liquids Based on Phosphonium Cations As Neat Lubricants or Lubricant Additives for a Steel/Steel Contact
I. Otero, E. R. Lopez, M. Reichelt, M. Villanueva, J. Salgado, J. Fernandez
ACS Applied Materials & Interfaces (2014) 6:13115

Short term missions

Iago Rodriguez PalmeiroAutomated MD simulations of ionic liquid properties at charged interfaces
Anna PawlowskaCellulose dissolution in eutectic mixtures of ionic liquids and determination of their physical properties
Aleksandra DimitrijevicAqueous biphasic systems based on cholinium-based ionic liquids for the simultaneous extraction, concentration and purification of cancer biomarkers from biological fluids
Catarina FlorindoCharacterization of Ionic Liquids and Deep Eutectic Solvents using solvatochromic probes
Nikola ZdolsekAqueous biphasic systems based on ionic liquid for extraction of the selected radionuclides
Interaction between Ionic Liquids and WaterInteractions and structure in ionic liquid solutions
Ctirad CervinkaIonic Liquids for Novel Porous Materials
Sandra Cristina da Silva BernardoDetermination of osmotic virial coefficients: evaluation of their applicability on the prediction of the behaviour of Immunoglobulin Y in aqueous biphasic systems composed of ionic liquids
Martin WildCO2 solubility in different ionic liquids containing [C2mim] cation
Emilie BordesInteractions and structure in ionic liquid solutions
Meike LeuSolubility of CO2 and CH4 in C4mim FeCl4
Ines Otero FernandezX-ray photoelectron spectroscopy XPS of worm surfaces lubricated with ionic liquids
Tatsiana LiavitskayaCO2 solubility in the mixture of two ionic liquids
Martin HübnerExtraction of proteins using IL containing aqueous biphasic systems
Monia MartinsActivity coefficients at infinite dilution of terpenes and terpenoids in ionic liquids
Sonja PlatzerLiquid-liquid extraction of europium and americium by task-specific ionic liquids
Isabel MachadoSelection of single stranded DNA-aptamers in unconventional ionic liquid solutions
Martin WildChemi- and physisorption of CO2 in ionic liquids
Snezana PapovicStudy on interactions of imidazolium based ionic liquids with selected lactones
Madga CabanPartition of mandelic acid by applying ABS based in chiral ionic liquids
Christina ApostolidouDissolving of complex molecules: Effect of the ionic liquid structure on keratin dissolution
Ana Paula TavaresPartition of oxidative enzymes using ionic liquid based aqueous biphasic systems
Ctirad CervinkaInterfacial layer of ionic liquids near electrode materials
Marlene ScheuermeyerSolvation structure of two transition metal (II)ions in [NTf2]-based low temperature molten salts investigated by Raman spectroscopy
Snezana PapovicStudy on interactions of imidazolium based ionic liquids with selected lactons
Imprint: (as stipulated by austrian law, MedienG 2005): S. Boresch / C. Schroder,
Institut für Computergestützte Biologische Chemie, Währinger Strasse 17, 1090 Wien, Austria