Mercury Capture from Petroleum Using Deep Eutectic Solvents. Supporting Information

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1 Mercury Capture from Petroleum Using Deep Eutectic Solvents Supporting Information Samah E. E. Warrag a,b, Evgenii O. Fetisov c, Dannie J.G.P. van Osch b, David B. Harwood c, Maaike C. Kroon a,b, J. Ilja Siepmann c,* and Cor J. Peters a,d,* a Khalifa University of Science and Technology, Petroleum Institute, Chemical Engineering Department, P. O. Box 2533, Abu Dhabi, United Arab Emirates b Eindhoven University of Technology, Department of Chemical Engineering and Chemistry, P. O. Box 513, 5600 MB Eindhoven, The Netherlands c University of Minnesota, Department of Chemistry and Chemical Theory Center, Minneapolis, MN 55455, United States d Colorado School of Mines, Chemical and Biological Engineering Department and Center for Hydrate Research, Golden, CO 80401, United States Corresponding Authors: J. Ilja Siepmann siepmann@umn.edu and Cor J. Peters cpeters@pi.ac.ae 1

2 Content 1. DES Structure Experimental Density and Viscosity Data DES Structure NMR analyses were performed to investigate if the constituents of the DES reacted with each other. For all four DESs deuterated water (D 2 O) was used as NMR solvent. Precision tubes (8 ) from the brand Wilmad with an outer diameter of 5 mm were used. The 1 H NMRs were recorded in 64 scans with a relaxation time of 3s. The 13 C NMRs were taken in 1024 scans with a relaxation time of 5s. Fourier transformation was automatically performed with the recording software VnmrJ, and MestreNova (version ) was used for the analysis of the spectra. The spectra were analyzed as measured. All 13 C NMR spectra showed the same number of peaks at the approximate position as theoretically predicted with Chembiodraw (version ). The 1 H NMR spectra showed the proper peaks except for the peaks of the acids and alcohol. These could not be measured since these hydrogens will be exchanged with the deuteriums of the deuterated water. Predictions made with Chembiodraw were used to check the shifts if condensations would occur. No big shifts were observed. From the combination of only small shifts in the 1 H NMR spectra and no extra peaks in the 13 C NMR spectra, it is concluded that no reaction between the constituents of the DES has occurred. 2

3 1.1. Choline chloride: Urea (1:2) (DES-1) Carbon (DES-1) Figure S1: 13 C NMR spectrum of DES-1 constituted of choline chloride and urea in a 1:2 molar ratio 3

4 Proton (DES-1) Figure S2: 1 H NMR spectrum of DES-1 constituted of choline chloride and urea in a 1:2 molar ratio 4

5 1.2. Choline chloride: ethylene glycol (1:2) (DES-2) Carbon (DES-2) Figure S3: 13 C NMR of DES-2 constituted of choline chloride and ethylene glycol in a 1:2 molar ratio 5

6 Proton (DES-2) Figure S4: 1 H NMR spectrum of DES-2 constituted of choline chloride and ethylene glycol in a 1:2 molar ratio 6

7 1.3. Choline chloride: levulinic acid (1:2) (DES-3) Carbon (DES-3) Figure S5: 13 C NMR spectrum of DES-3 constituted of choline chloride and levulinic acid in a 1:2 molar ratio 7

8 Proton (DES-3) Figure S6: 1 H NMR spectrum of DES-3 constituted of choline chloride and levulinic acid in a 1:2 molar ratio 8

9 1.4 Betaine: levulinic acid (1:2) (DES-4) Carbon (DES-4) Figure S7: 13 C NMR spectrum of DES-4 constituted of betaine and levulinic acid in a 1:2 molar ratio 9

10 Proton (DES-4) Figure S8: 1 H NMR spectrum of DES-4 constituted of betaine and levulinic acid in a 1:2 molar ratio 10

11 2. Experimental Density and Viscosity Data Table S1: Numerical values for the experimental densities and viscosities of DES-3 and DES-4 at different temperatures and at atmospheric pressure. The standard deviations are estimated from replicate measurements. DES-3 DES-4 T ρ η ρ η [K] [kg m 3 ] [mpa s] [kg m 3 ] [mpa s] ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ±

Supporting information

Electronic Supplementary Material (ESI) for Chemical Communications. This journal is The Royal Society of Chemistry 2016 Supporting information Removal of Alkali and Transition Metal Ions from Water with