Hydrolysis of chitosan to yield levulinic acid and 5-hydroxymethylfurfural in water under microwave irradiation

Kerton, Francesca M. and Omari, Khaled Walid Baker and Besaw, Jessica E. (2012) Hydrolysis of chitosan to yield levulinic acid and 5-hydroxymethylfurfural in water under microwave irradiation. Green Chemistry, 14 (5). pp. 1480-1487. ISSN 1463-9270

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Abstract

A novel route has been developed that yields levulinic acid (4-oxopentanoic acid, LA) and 5-hydroxymethylfurfural (5-HMF) from chitosan. Hydrolysis of chitosan was performed in the presence of a range of Lewis acids with SnCl4·5H2O providing the best results. All reactions were performed in sealed vessels under microwave irradiation at 200 °C for 30 min. Typical pressures achieved were 17 to 19 bar. 23.9 wt% LA was produced from 100 mg chitosan using 0.24 mmol SnCl4·5H2O and 4 mL water. Under more dilute conditions, 10.0 wt% 5-HMF was obtained using 0.12 mmol SnCl4·5H2O and 15 mL water. We propose that under more concentrated reaction conditions the 5-HMF formed reacts further to produce LA. When chitin is treated similarly, no 5-HMF is produced but up to 12.7 wt% LA can be obtained. For comparison, 32.0 wt% LA was produced from 100 mg glucosamine hydrochloride using 0.26 mmol SnCl4·5H2O and 20 mL water. This corresponds to a yield of 59.4%. The SnCl4 forms SnO2 and HCl in solution and under similar conditions using SnO2 and HCl, chitosan formed 27.4 wt% LA.

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