Designing the Head Group of Switchable Surfactants

Abstract

This thesis is an investigation into the development of amidine and guanidine based compounds to be employed as switchable surfactants. The surface activity of these molecules can be triggered by reaction with a benign gas, CO2. The ultimate application of these surfactants was to be used as emulsifying and demulsifying agents of crude oil and water emulsions. Synthesis and characterization of the following desired bases: N’-octyl-N,N-dimethylacetamidine (1), 2-octyl-2-imidazoline (2), 1-methyl-2-octyl-2-imidiazoline (3), N’-(4-heptylphenyl)-N,N-dimethylacetamidine (4), N’-(4-(octyloxy)phenyl)-N,N-dimethylacetamidine (5), N’-(4-(methyloxy)phenyl)-N,N-dimethylacetamidine (6), and N-octyl-N',N',N",N"-tetramethylguanidine (7) was carried out. Their solubility in water was quantified with NMR spectroscopy. All bases were reacted with CO2 and H2O to form bicarbonate salts, of which in situ characterization was achieved by IR and NMR spectroscopy. Percent conversion to the protonated forms at elevated temperatures was determined using NMR spectroscopy. A direct correlation between switchability and basicity was observed, as the strongest bases possessed the largest conversions to the protonated species, even at higher temperatures. The enthalpy of protonation was determined for each base through calorimetry experiments. These compounds were tested as demulsifying surfactants of crude oil and water emulsions. Demulsifying ability was determined to differ greatly with the head group structure of the various surfactants.