Heteropoly acid catalysts in upgrading of biorenewables: Cycloaddition of aldehydes to monoterpenes in green solvents

Cotta, Rafaela F, da Silva Rocha, Kelly A, Kozhevnikova, Elena F, Kozhevnikov, Ivan V ORCID: 0000-0003-2453-5256 and Gusevskaya, Elena V (2017) Heteropoly acid catalysts in upgrading of biorenewables: Cycloaddition of aldehydes to monoterpenes in green solvents. APPLIED CATALYSIS B-ENVIRONMENTAL, 217. pp. 92-99.

Text Gusevskaya Cycloaddition in green solvents - IK corr (2).pdf - Author Accepted Manuscript Download (328kB)

Abstract

Acidic Cs salt of tungstophosphoric heteropoly acid, Cs2.5H0.5PW12O40 (CsPW), is excellent solid acid catalyst for liquid-phase cycloaddition reactions of biomass-based and easily available from essential oils monoterpenic compounds, such as limonene, α-terpineol, α-pinene, β-pinene and nerol, with aldehydes, including benzaldehyde, crotonaldehyde as well as biomass-derived cuminaldehyde and trans-cinnamaldehyde. The reactions give oxabicyclo[3.3.1]nonene compounds potentially useful for the fragrance and pharmaceutical industries in good to excellent yields. The process is environmentally benign and can be performed in biomass-derived solvent 2-methyltetrahydrofuran and eco-friendly “green” organic solvents such as dimethylcarbonate and diethylcarbonate under mild conditions at low catalyst loadings without leaching problems. The solid CsPW catalyst can be easily separated from the reaction media and low-boiling solvents can be removed by distillation. Silica-supported H3PW12O40 also demonstrated good performance in these reactions.

Item Type:	Article
Uncontrolled Keywords:	Biomass-based feedstock, Cycloaddition, Green solvents, Heterogeneous acid catalysis, Monoterpenes
Depositing User:	Symplectic Admin
Date Deposited:	12 Feb 2019 14:55
Last Modified:	19 Jan 2023 07:02
DOI:	10.1016/j.apcatb.2017.05.055
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3008020