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Sulfonated Expanded Polystyrene Waste Promotes the (+)-Citronellal Cyclization Reaction: A Sustainable Alternative Process for Biomass Valorization

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Abstract

In this work, sulfonated expanded polystyrene waste (WEPS), obtaining from recycling of the expanded polystyrene (EPS) waste by low-cost sulfonation reaction, were successfully applied as environmentally benign acid solid in the liquid-phase cyclization of (+)-citronellal (1), under mild reaction conditions. (-)-Isopulegol (2) and (+)-neoisopulegol (3) were obtained with a total yield equal to 80%. Products 2 and 3 have direct industrial application in the composition of fragrances and flavorings. (-)-Isopulegol is also used as a synthesis intermediate of (-)-menthol. It was not observed the leaching of acid sites from WEPS to reaction solution, thereby, this process presented heterogeneuos nature. The WEPS was stable in the reaction medium and presented little significant loss of its performance in consecutive reactions of its reuse. In addition, WEPS showed better performance than commercial resin Amberlyst-15, in the same reaction conditions. The use of WPES as acid solid in reactions of industrial interest is an attractive, low-cost and environmentally friendly alternative for application of this material, obtained by recycling EPS waste, for adding value to natural ingredients obtained from biomass.

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Acknowledgements

We acknowledge Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG), Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), Pró-Reitoria de Pesquisa, Pós-Graduação e Inovação da Universidade Federal de Ouro Preto (PROPP-UFOP) for the financial support, CAPES for the access to the virtual library containing international journals and Laboratory of Organometallic Catalysis at Universidade Federal de Minas Gerais by GC-MS analysis. The authors wish to thank Maria Helena Araújo for kindly share the WEPS for the studies herein presented.

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  1. Departamento de Química, Universidade Federal de Ouro Preto, Campus Morro do Cruzeiro s/n, Ouro Preto, Minas Gerais, 35400-000, Brazil

    Maria Stella Palhares Ribeiro, Rayane Rocha Silva Pinto, Kelly A. da Silva Rocha & Camila Grossi Vieira

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  1. Maria Stella Palhares Ribeiro
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Ribeiro, M.S.P., Pinto, R.R.S., da Silva Rocha, K.A. et al. Sulfonated Expanded Polystyrene Waste Promotes the (+)-Citronellal Cyclization Reaction: A Sustainable Alternative Process for Biomass Valorization. Waste Biomass Valor 12, 4695–4702 (2021). https://doi.org/10.1007/s12649-020-01319-4

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