Limonene derived lyotropic liquid crystals: synthesis and structure

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Background: In 2020 it was estimated that were 90 million tonnes of bio-chemicals and biopolymers produced, while petrol chemical sources are estimated to be the source of a further 330 million tonnes of chemicals and polymers. Surfactants have a wide array of applications, with global demand in 2018 of around 16.5 million megatons with an annual growth rate of around 3%. Lyotropic liquid crystals are states of matter in which an amphiphile (e.g. a surfactant) is dissolved at a certain concentration, at a certain temperature and concentration. Globally citrus is the largest fruit crop in the world, and their essential oils contain numerous useful compounds. One such compound is limonene, making up more than 85% of the essential oil content of oranges. Limonene can also obtained from the pyrolysis of waste rubber tyres, and is currently being studied as a feedstock material jet fuel additives and plasticisers. Project Objectives: The initial aim of this project are to synthesise novel surfactants using limonene as a feedstock, adhering to the 12 principles of green chemistry where possible. The differing reactivity of the endo- and exo-cyclic olefins will be exploited to produce hydrophilic (e.g. diol) and hydrophobic (e.g. alkyl) regions. Following synthesis, we will map the phase diagram with water as a function of concentration and temperature. We will utilise 2D SAXS/WAXS to obtain structural information. Atomistic MD simulations will be utilised to rationalise experimental trends. Ultimately, a family of materials will be prepared - initially using limonene but with the possibility of expanding to alternate terpenoids - and the differences in observed lyotropic behaviour will be related back to molecular structure.