Abstract
A homogeneous process for the formation of various cellulose esters using the ionic liquid [EMIM]OAc and vinyl esters is described.
Highlights
Cellulose as a part of plant cell walls is the most abundant biopolymer on Earth
Vinyl ester-based synthesis in [EMIM]OAc As a model reaction for initial parameter optimisation, glucose laurates were synthesised based on vinyl esters in [EMIM]OAc and product identification was carried out by LC-MS/Electronic supplementary information (ESI) analysis
In addition to glucose as a model substrate, the esterification of cellulose with different vinyl esters, especially vinyl laurate, in [EMIM]OAc was investigated (Fig. 1). 3% w/w of cellulose, solubilised in [EMIM]OAc, was esterified with different amounts of vinyl laurate (2–5 mol per anhydroglucose units (AGU)) at 80 °C for 4 hours under continuous stirring
Summary
Cellulose as a part of plant cell walls is the most abundant biopolymer on Earth. With an estimated annual biosphere production of 9 × 1010 tons, cellulose is a remarkable natural resource, which is nowadays mainly used for the production of paper and pulp or is burned in order to produce heat.[1]. A variety of cellulose esters using long chain fatty acids, aromatic, branched and sterically challenging substrates, like pivalate, as acyl donors are accessible This process leads to a high DS requiring a low amount of acyl donor, it ensures a constant high degree of polymerisation and allows significantly lower acetate activation in comparison with the anhydride based synthesis in [EMIM]OAc. This process leads to a high DS requiring a low amount of acyl donor, it ensures a constant high degree of polymerisation and allows significantly lower acetate activation in comparison with the anhydride based synthesis in [EMIM]OAc Apart from these facts the vinyl esterbased synthesis shows benefits like high conversion rates, volatile side products, no need for acid scavengers, reusability of [EMIM]OAc, mild reaction conditions, low toxicity and biodegradable solvents
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