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Brønsted acid functionalized melamine-supported porphyrin trimer for one-step synthesis of alkyl-12-hydroxyoctadecanoate under irradiation of LED light

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Abstract

Biodiesel obtained from castor oil is considered a green renewable resource and is an admirable substitute for petro-based diesel, which originated from non-renewable energy sources. In this investigation, the transformation of castor oil to alkyl-12-hydroxyoctadecanoate, biodiesel was attained using a separable and reusable heterogeneous Brønsted acid functionalized melamine-supported porphyrin trimer photocatalyst (BAFMsPPc). This BAFMsPPc was scrutinized by using NMR, FT-IR, and SEM/EDAX. Moreover, a UV-visible spectrophotometer was employed for measuring the optical band gap (1.15 eV) and Hammett acidity (H0=0.74). The ethyl-12-hydroxyoctadecanoate was acquired using 15 mg of BAFMsPPc photocatalyst under the luminance of visible light (5W/9W/12W) in a home-made photoreactor consisting of a temperature sensor and controller. The ethyl-12-hydroxyoctadecanoate was evidenced by 1H, 13C NMR. Furthermore, BAFMsPPc photocatalyst was competent for the simultaneous reduction and transesterification of castor oil to produce alkyl-12-hydroxyoctadecanoate under irradiation of visible light by means of formic acid as a hydrogen source and validated by 1H and 13C NMR. The direct conversion of castor oil to alkyl-12-hydroxyoctadecanoate by simultaneous transesterification and reduction beneath optimized conditions in the presence of photocatalyst and formic acid is the most feasible method. Moreover, the gram-scale reaction succeeded to get ethyl-12-hydroxyoctadecanoate under optimized conditions. The ethyl-12-hydroxyoctadecanoate was blended with commercial diesel at 10 and 15% (v/v), exhibiting comparable cetane no. of 10% blended sample with the marketed diesel sample. Furthermore, the recyclability and stability of BAFMsPPc were confirmed by Fourier transform-infrared red spectroscopy and nuclear magnetic resonance after the 6th run obeying the principle of green chemistry supporting environmentally benign procedure.

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Acknowledgements

The authors would like to thank VIT-SIF SAS and the SEM facility at SBST VIT, Vellore, for providing the instrumentation. The authors would also like to thank VIT for sponsoring a “VIT SEED GRANT” to carry out this research. We gratefully appreciate VIT management, the Department of Chemistry (SAS), and the “Smart Materials Laboratory for Bio-sensing and Catalysis” for their assistance with fundamental research facilities for doing research.

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Authors and Affiliations

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

    Shubham Avinash Deshmukh, Bhairav Chandroday Mataghare, Vijay Shivaji Patil, Subodh Uttamrao Raut, Piyush Radheshyam Yadav, Rutuja Ganesh Maske & Pundlik Rambhau Bhagat

  2. Department of Chemistry, Arts, Commerce and Science College, Arvi Affiliated to RTMNU, Nagpur, Maharashtra, India

    Kamlesh Rudreshwar Balinge

  3. Chemical Engineering Department, Motilal Nehru National Institute of Technology, Allahabad, Uttar Pradesh, 211004, India

    Dipesh S. Patle

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  1. Shubham Avinash Deshmukh
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Contributions

All authors contributed to the conception and design. Material preparation, data collection, and analysis were performed by Shubham A. Deshmukh, Bhairav C. Mataghare, Vijay S. Patil, and Pundlik R. Bhagat. The draft of the manuscript is written by Shubham A. Deshmukh, Kamlesh R. Balinge, Piyush Radheshyam Yadava, Rutuja Ganesh Maskea, Dipesh S. Patle, and Pundlik R. Bhagat. Subodh U. Raut contributed to the data analysis and interpretation. The resources and conceptualizations of the protocol are supervised by Pundlik R. Bhagat. All authors read and approved the final manuscript. All authors are aware of the submission and agree to its publication.

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Highlights

➢ Brønsted acid functionalized melamine-supported porphyrin trimer for one-step synthesis of alkyl-12-hydroxyoctadecanote under irradiation of LED light.

➢ BAFMsPPc photocatalyst has shown efficient transesterification of castor oil with alcohol.

➢ A probable mechanism for the transesterification of castor oil and ethyl alcohol was proposed.

➢ Methyl ricinoleate has shown remarkable physicochemical properties with 10% blending using commercial diesel.

➢ A scavenger study indicated the formation of active species during photocatalytic conversion.

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Deshmukh, S.A., Mataghare, B.C., Patil, V.S. et al. Brønsted acid functionalized melamine-supported porphyrin trimer for one-step synthesis of alkyl-12-hydroxyoctadecanoate under irradiation of LED light. Biomass Conv. Bioref. (2023). https://doi.org/10.1007/s13399-023-04642-7

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