Heteropoly acid-catalyzed β-caryophyllene chemical transformations : synthesis route of value-added commercial products from components found in biorenewable resources.

Abstract

More sustainable catalytic processes applied to different reactions for of biorenewable derivatives production is an important trend in chemical industry, which constantly needs to update its processes for obtaining inputs not produced in sufficient quantity by nature, or with superior physicochemical properties to those of compounds acquaintances. This work reports the chemical transformation of β-caryophyllene, a sesquiterpene present in biorenewable materials, using the commercial heteropoly acid catalyst H3PW12O40. The process performed under conditions technologically and environmentally attractive, using less harmful ketone solvents (2-butanone and acetone). The products obtained were (-)-clovene, β-caryolanol and β-clovanol, at total yield 70–80%, by isomerization reaction associated with hydration reactions. All these products have known applications in different sectors of the fine chemicals industry, whether in isolated forms or as mixtures. (-)-Clovene and β-caryolanol have significantly higher commercial value, compared to β-caryophyllene. There are known applications for β-clovanol, although the compound has not yet been commercialized, making the process described here attractive for its production on an industrial scale. H3PW12O40 showed catalytic performance superior to H2SO4, a conventional mineral acid catalyst.