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Acetalization of β-citronellal Over a Renewable Carbon Catalyst Obtained from Bio-Oil Sulfonation: A Green Route to Obtain Valuable Feedstocks

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Abstract

In this work, an efficient renewable carbon catalyst obtained by bio-oil sulfonation was used for the first time to produce terpene acetals by condensation of β-citronellal with alkyl alcohols (methyl, ethyl, propyl, butyl, isopropyl) at room temperature. The catalyst was obtained by a simple bio-oil reaction with sulfuric acid at 393 K for different times (15, 30, 60, 90, 120, and 240 min). Potentiometric titrations and FT-IR analyses showed the formation of very strong acid sites, likely -SO3H, with surface concentrations reaching 0.35 and 0.50 mmol/ g. catalyst, for the catalyst obtained with reactions 120 and 240 min. These catalysts were used for β-citronellal condensation with alkyl alcohols to acetals with conversion and selectivity higher than 90%, at room temperature, using a 3.96 wt.% catalyst and 2 h reaction time. The effects of temperature, time, different alcohols, and catalyst load were evaluated. The catalyst can be recovered and reused four times without significant activity loss. The use of renewable origin solid catalysts, recyclable, and active in acetalization reactions at room temperature are positive aspects of this process.

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Acknowledgements

The authors are grateful for the financial support from CNPq and FAPEMIG (Brasil). This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior—Brasil (CAPES)—Finance Code 001.

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Authors and Affiliations

  1. Chemistry Department, Federal University of Vicosa, University Campus, Avenue P.H. Rolfs, Vicosa, Minas Gerais State, Zipcode 36570-000, Brazil

    Neide Paloma Gonçalves Lopes & Márcio José da Silva

  2. Chemistry Department, Federal University of Minas Gerais, Belo Horizonte, Zip-Code: 31270-901, Minas Gerais, Brasil

    Fabiane Carvalho Ballotin, Ana Paula de Carvalho Teixeira & Rochel Montero Lago

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  1. Neide Paloma Gonçalves Lopes
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  3. Ana Paula de Carvalho Teixeira
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  4. Rochel Montero Lago
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  5. Márcio José da Silva
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Contributions

All authors contributed to the study's conception and design. Material preparation, data collection and analysis were performed by Neide Paloma Gonçalves Lopes and Fabiane Carvalho Ballotin. The first draft of the manuscript was written by Márcio José da Silva, Rochel Montero Lago, and Ana Paula de Carvalho Teixeira. All authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

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Correspondence to Márcio José da Silva.

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Lopes, N.P.G., Ballotin, F.C., de Carvalho Teixeira, A.P. et al. Acetalization of β-citronellal Over a Renewable Carbon Catalyst Obtained from Bio-Oil Sulfonation: A Green Route to Obtain Valuable Feedstocks. Waste Biomass Valor 15, 1369–1377 (2024). https://doi.org/10.1007/s12649-023-02216-2

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