Over Design and Applications of Hydrophobic Deep Eutectic Solvents

Design and Applications of Hydrophobic Deep Eutectic Solvents

Avondlezing door Ir. Dannie J.G.P. van Osch, georganiseerd door de Rotterdamsche Chemische Kring. 

In 2003 a new class of innovative solvents, deep eutectic solvents (DESs), were presented into the literature.1 A DES is the combination of two or more solid components, which upon mixing self-associate, lowering the melting point. It is hypothesized that hydrogen bonding and presumably Van der Waals interactions give rise to the melting point depression, introducing the liquid DES.2 In comparison with ionic liquids (ILs), DESs have two main advantages. First, a DES is easy to prepare since it is merely mixing of the two components of the DES at room or moderate temperatures. Second, by selection of the components the sustainability and physicochemical properties can be tuned.2

Until 2015 all the presented DESs were hydrophilic, due to the high amount of hydrogen bonding groups on the components of these DESs. In 2015 we presented hydrophobic DESs for the first time. This hydrophobic variant of DESs was based on decanoic acid and quaternary ammonium salts.3 Upon their discovery they already showed their value as a solvent immiscible with water for the extraction of volatile fatty acids from water.

As a follow up these hydrophobic DESs composed of decanoic acid and various quaternary ammonium salts were used for the capture of carbon dioxide (CO2).4 The results showed capture ability comparable with the second best IL.

Furthermore, a DES composed of decanoic acid and lidocaine was used for the removal of transition and alkali metal ions from water.5 The results showed that within 10 seconds all transition metal ions could be extracted with high extraction efficiencies, even for low DES/water mass ratios and high Co2+ concentrations.

Despite that the previously mentioned DESs already show promise, it was our opinion that improvements in the sustainability of these hydrophobic DESs was still possible. Thus, it was decided to screen into more hydrophobic DESs based on various plant extracts (terpenoids). The results showed some very promising new and more sustainable hydrophobic DESs that had a low viscosity and large density differences with water. Furthermore, these DESs induced no change in the pH of the water phase and had only minor loss of organics to the water phase upon mixing with water.

One of this new hydrophobic DESs was used for the production of DES in H2O emulsions for the first time. The surfactant sodium dodecyl sulfate was used to stabilize the DES droplets in the water phase. It was specifically chosen to use a surfactant to investigate whether this two component system would also induce droplet growth. The results show that the droplet growth was comparable with the one component solvent decane. Both solvents show a linear correlation between the d3 and time. However, the DES showed an overall lower growth rate.


  1. A. P. Abbott, G. Capper, D. L. Davies, R. K. Rasheed, and V. Tambyrajah, Chemical Communications, 2003, 70–71.
  2. M. Francisco, A. van den Bruinhorst, and M. C. Kroon, Angewandte Chemie, 2013, 52, 3074–85.
  3. D. J. G. P. van Osch, L. F. Zubeir, A. van den Bruinhorst, M. A. Rocha, and M. C. Kroon, Green Chemistry, 2015, 17, 4518–4521.
  4. C. H. J. T. Dietz, D. J. G. P. van Osch, M. C. Kroon, G. Sadowski, M. van Sint Annaland, F. Gallucci, L. F. Zubeir, and C. Held, Fluid Phase Equilibria, 2017.
  5. D. J. G. P. van Osch, D. Parmentier, C. H. J. T. Dietz, A. van den Bruinhorst, R. Tuinier, and M. C. Kroon, Chemical Communications, 2016, 52, 11987–11990.

Curriculum vitae
Dannie van Osch was born on the 29th of June, 1990 in Geleen, the Netherlands. After finishing his pre-university college from Trevianum Scholengroep in Sittard in 2008, he started a BSc education in Chemical Engineering at Eindhoven University of Technology. During his BSc research project he investigated the Claisen rearrangement under high temperature and pressure in a microreactor, in which he was supervised by dr. Timothy Noël. He obtained his BSc degree in 2012. His BSc research project was selected for a workshop presentation for the student research award at the VSNU Student Research Conference 2013.

In 2012 he started his MSc education in Chemical Engineering with a specialization in process engineering at Eindhoven University of Technology. During his master education Ferdinand C. Leeger and he were finalists at the Huntsman design contest at the ECCE9-ECAB2 congress. They obtained a 4th place. For his master thesis he investigated metal free photocatalytic perfluoroalkylation of pyrroles and indoles in microreactors and a study towards the distance-to-time transformation in microreactors under the supervision of dr. Timothy Noël. During his internship he performed thermodynamic modeling of the NH3-CO2-H2O system with the extended UNIQUAC model. Dannie received his Master degree with the judicium cum laude in 2014.

Dannie started his PhD in September 2014 under the supervision of prof. dr. Kroon. When she left at the start of 2016 the supervision of his PhD project was transferred to prof. dr. R. Tuinier, dr. J. van Spronsen and dr. A.C.C. Esteves. In the separation technology group of professor Kroon he worked on the discovery of hydrophobic deep eutectic solvents and their use for the capture of CO2. Cooperation between the separation technology group and the physical chemistry group of professor Tuinier led to investigation of metal ion extraction with hydrophobic DESs and a screening into new, more sustainable hydrophobic DESs. During his time in the physical chemistry group he worked on hydrophobic DES in H2O emulsions and surfactant based deep eutectic solvents for the production of emulsions. Most of this work is presented in this thesis. The work on metal ion extraction removal from water with hydrophobic DESs gained widespread attention in the Dutch news, including an article in ‘De Volkskrant’ and an interview on NPO radio 1 in the show ‘Nieuws en Co’. Next to presenting his work on scientific congresses, he also presented his work on multiple conferences for secondary school teachers and amanuenses and for high school students. Dannie has contributed to teaching thermodynamics (work classes and occasionally a lecture) for BSc students. During one year of his PhD he was in the board of the physical chemistry group, in which he represented the PhDs and Postdocs.

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