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Efficient photocatalytic acetalization of furfural to biofuel components using carboxyl-functionalized porphyrin photocatalyst, under visible light irradiations

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Abstract

The carboxyl-functionalized porphyrin entangled with benzimidazolium-based ionic liquid (CFPBIL) was successfully synthesized and characterized by FT-IR, FT-NMR and TGA analysis. The proton level was determined by the Hammett acidity function, and DR spectra have been supported to confirm the band gap of photocatalyst. The present study reveals the metal-free, conventional photocatalytic acetalization of furfural to biofuel components under visible light irradiations using carboxyl-functionalized porphyrin catalyst. The effect of different parameters on the photocatalytic reaction, catalyst loading, ratio of furfural:alcohol, duration and intensity of light were investigated. The model reaction of furfural and ethanol in a home-made photoreactor using a 5-W LED presented that a very high yield of furfural acetal (92%) could be obtained under optimized conditions. Moreover, the eco-friendly method of acetalization reactions with higher alcohols (1-butanol, 1-pentanol, 1-hexanol, 1-octanol) was carried out at optimized reaction conditions which also afforded good to excellent yield of the target products, demonstrating the potential of CFPBIL as a highly active, stable and recyclable heterogeneous photocatalyst. Moreover, physical properties of biodiesel–diesel blends comprising B10, B20 and B30 were determined and furfural acetals were found as a potential fuel additive.

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Acknowledgements

The authors acknowledge the SIF DST-VITFIST, the SEM facility at SBST and RGEMS (VIT, Vellore) for allowing us to use the analytical instruments. We would like to extend our thanks to the ‘Smart Materials Laboratory for Bio-Sensing and Catalysis’ for providing the basic facilities.

Funding

This study received funding from the VIT Vellore through the ‘VIT SEED GRANT’ for carrying out this research work.

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  1. Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore, Tamil Nadu, 632014, India

    Subodh U. Raut & Pundlik R. Bhagat

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Correspondence to Pundlik R. Bhagat.

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Highlights

• Metal-free carboxyl functionalized porphyrin photocatalyst grafted with benzimidazolium base ionic liquid (CFPBIL) was synthesized.

• the acetalization of Furfural performed with 1-butanol 1-pentanol 1-hexanol and 1-octanol at ambient conditions in presence of visible light irradiations (5 W).

• Maximum 92% yield of the 2-(bis(pentyloxy)methyl)furan biofuel component achieved using 15 mg photocatalyst in 16 h in a home-made photoreactor.

• CFPBIL Photocatalyst showed good recyclability upto seven successive runs.

• Furfural acetal 2-(bis(pentyloxy)methyl)furan found promising additive for diesel with comparable results.

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Raut, S.U., Bhagat, P.R. Efficient photocatalytic acetalization of furfural to biofuel components using carboxyl-functionalized porphyrin photocatalyst, under visible light irradiations. Biomass Conv. Bioref. 13, 7737–7754 (2023). https://doi.org/10.1007/s13399-021-01658-9

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