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Effective utilization of green synthesized CuO nanoparticles for the preparation of keto-1,2,3-triazole analogues of protected amino acids/dipeptide acids and recyclable catalyst for the optimization and kinetic study of biodiesel production

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Abstract

Heterogeneous nano-copper oxide catalyst was prepared via a simple eco-friendly, solution combustion method using novel seed extract of Terminalia bellirica and characterized by various techniques like powder X-ray diffraction, Fourier transform infrared spectroscopy, scanning electron microscopy, ultraviolet–visible spectroscopy, and Brunauer–Emmett–Teller analysis. The prepared catalyst demonstrated a greater catalytic activity towards the synthesis of Nα-protected amino keto-1,2,3-triazoles analogues via the three-component reaction among amino acyl chloride derivatives of protected amino acids/dipeptide acids, phenylacetylene and sodium azide. Further, synthesized CuO nanoparticles were evaluated for their antibacterial activity against Escherichia coli, Pseudomonas aeruginosa, Salmonella typhimurium and Bacillus subtilis, revealed that nano-CuO have significant activity. In addition, nano-CuO showed an excellent catalytic activity in biodiesel production optimization from Terminalia bellirica oil and achieved 97% yield of Terminalia bellirica methyl ester/biodiesel with optimum conditions of 3.5 wt% catalyst loading, 9:1 methanol-to-oil molar ratio, 65 °C temperature and 60 min reaction time. From the kinetic study of biodiesel production at different temperatures activation energy (Ea) of 38.06 kJ/mol and frequency factor (A) of 2.2 × 104 min−1 was observed. The fuel properties of produced biodiesel were in the range of ASTM standards.

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Data Availability Statement

This manuscript has associated data in a data repository. [Authors’ comment: The data provided in the manuscript are available in the request by contacting with the corresponding author.]

Abbreviations

PXRD:

Powder X-ray diffraction

UV–visible:

Ultraviolet–visible spectroscopy

BET:

Brunauer–Emmett–Teller

CuO NPs:

Copper oxide nanoparticles

TBME:

Terminalia bellirica Methyl ester

FTIR:

Fourier transform infrared spectroscopy

SEM:

Scanning electron microscopy

Ea:

Activation energy

A:

Frequency factor

CuSO4 :

Copper sulphate

Cu(NO3)2 :

Cupric nitrate

Fe2O3 :

Ferric oxide

ZnO:

Zinc oxide

Ag/ZnO:

Silver doped zinc oxide

Mg/ZnO:

Magnesium doped zinc oxide

BJH:

Barrett–Joyner–Halenda

1H NMR:

Proton Nuclear Magnetic Resonance Spectroscopy

13C NMR:

Carbon-13 Nuclear Magnetic Resonance Spectroscopy

DMSO:

Dimethylsulphoxide

TLC:

Thin-layer chromatography

FFA:

Free fatty acids

JCPDS:

Joint Committee on Powder Diffraction Standards

MIC:

Minimum Inhibitory Concentration

MBC:

Minimum Bacterial Concentration

HPLC:

High-performance liquid chromatography

R:

Universal gas constant (8.314 J mol−1 K−1)

ASTM:

American Society for Testing and Materials

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Acknowledgements

We thank the Principal, CEO and Director of Siddaganga Institute of Technology, Tumakuru, Karnataka, for the research facilities. One of the authors (HSL) is thankful to the Vision Group of Science and Technology, Department of Information Technology, Biotechnology and Science & Technology, Govt. of Karnataka, for providing funds under CISEE programme (VGST-GRD No. 472) to carry out the present research work by means of a sponsored project.

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Authors and Affiliations

  1. Department of Chemistry, Siddaganga Institute of Technology, Tumakuru, Karnataka, 572 103, India

    M. Raghavendra & H. S. Lalithamba

  2. Centre for Nano and Material Sciences, Jain University, Bangalore, Karnataka, 562 112, India

    K. V. Yatish

  3. Department of Mechanical Engg., Siddaganga Institute of Technology, Tumakuru, Karnataka, 572 103, India

    B. R. Omkaresh

  4. Department of Chemistry, Channabasaveshwara Institute of Technology, Tumakuru, Karnataka, 572216, India

    M. Raghavendra

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  1. M. Raghavendra
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Correspondence to H. S. Lalithamba.

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Raghavendra, M., Yatish, K.V., Lalithamba, H.S. et al. Effective utilization of green synthesized CuO nanoparticles for the preparation of keto-1,2,3-triazole analogues of protected amino acids/dipeptide acids and recyclable catalyst for the optimization and kinetic study of biodiesel production. Eur. Phys. J. Plus 136, 1156 (2021). https://doi.org/10.1140/epjp/s13360-021-02137-w

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