One-Pot Synthesis of Menthol from Citral over Ni/H-β-38 Extrudates Containing Bentonite Clay Binder in Batch and Continuous Reactors

Irina L. Simakova, Zuzana Vajglová, Mark Martínez-Klimov, Kari Eränen, Markus Peurla, Päivi Mäki-Arvela, Dmitry Yu Murzin*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

3 Citations (Scopus)
35 Downloads (Pure)

Abstract

Optimization of bifunctional Ni catalysts was performed to enhance the catalytic performance in the one-pot synthesis of commercially valuable menthol from citral. The effect of nickel precursors (nitrate, chloride, acetate, and sulfate) and the addition of bentonite clay was investigated in citral transformations in a batch reactor at 70 °C and 10 bar hydrogen, demonstrating higher activity for the Ni-H-β-38-bentonite composite derived from a nickel nitrate precursor, which can be attributed to a higher surface area, optimal Brønsted to Lewis acidity and metal particle size, as well as the egg-shell distribution of Ni particles. H-β-38 impregnated with nickel nitrate, followed by calcination and reduction, was shaped with bentonite as a binder to give extrudates for exploring the citral transformations in the trickle-bed reactor at 50-70 °C and 10 bar hydrogen. The highest selectivity to the desired menthols of 45% was obtained with 70% stereoselectivity to the menthol isomer at 70 °C. The apparent activation energy for citral transformations to menthols of 18.6 kJ/mol indicated the presence of mass transfer limitations. Catalytic activity was linked with the physical-chemical properties, which were characterized by transmission electron microscopy, X-ray diffraction, temperature-programmed reduction, Fourier transform infrared spectroscopy with pyridine, N2 physisorption, and inductively coupled plasma-optical emission spectrometry methods.

Original languageEnglish
Pages (from-to)295-310
Number of pages16
JournalOrganic Process Research and Development
Volume27
Issue number2
DOIs
Publication statusPublished - 17 Feb 2023
MoE publication typeA1 Journal article-refereed

Keywords

  • citral
  • clay binder
  • menthol
  • Ni precursors
  • shaped catalyst
  • trickle-bed

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