Valorisation of plant oil derivatives via metathesis reactions: Study of the cross-metathesis of methyl oleate with cinnamaldehyde

Nieres, Pablo Daniel; Trasarti, Andrés Fernando; Apesteguı́a, C.R.

doi:10.1016/j.mcat.2018.06.010

Molecular Catalysis

2020

DOI: 10.1016/j.mcat.2018.06.010

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Valorisation of plant oil derivatives via metathesis reactions: Study of the cross-metathesis of methyl oleate with cinnamaldehyde

Pablo Daniel Nieres

Andrés Fernando Trasarti

C.R. Apesteguı́a

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Cited by 5 publications

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“…Value of the data The cross metathesis of methyl oleate with cinnamaldehyde is an attractive route for the synthesis of various useful intermediates and compounds for fine chemistry and polymer industry [1] . Equilibrium data for MO/cinnamaldehyde reaction (unpublished to date) are relevant to improve the yield in cross-metathesis products, in competition with the MO self-metathesis reaction.…”

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Equilibrium data for the cross-metathesis of methyl oleate with cinnamaldehyde

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Here we present equilibrium data for the cross-metathesis of methyl oleate (MO) with cinnamaldehyde (CA) obtained experimentally from liquid-phase catalytic tests conducted at 323 K. The reaction was carried out in batch reactors, using different reactant molar ratios and the 2nd generation Ru Hoveyda-Grubbs complex as catalyst. Reaction mixtures at the equilibrium were analyzed by gas chromatography. Equilibrium constants were determined by assuming unitary activity coefficients for a cinnamaldehyde/methyl oleate equimolar ratio, and the validity of that approximation was evaluated by calculating the equilibrium conversions for different reactant molar ratios.

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confidence: 99%

“…The cross metathesis of methyl oleate with cinnamaldehyde is an attractive route for the synthesis of various useful intermediates and compounds for fine chemistry and polymer industry [1] .…”

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confidence: 99%

Equilibrium data for the cross-metathesis of methyl oleate with cinnamaldehyde

2018

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Two highly sensitive fluorescent probes based on cinnamaldehyde with large Stokes shift for sensing of HSO3− in pure water and living cells

et al. 2020

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Looking for the Noncyclic(amino)(alkyl)carbene Ruthenium Catalyst for Ethenolysis of Ethyl Oleate: Selectivity Is on Target

et al. 2018

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A wide set of 65 diverse Ru metathesis catalysts was investigated in the ethenolysis reaction of biosourced ethyl oleate to allow the comparison between the catalyst structure and its activity and selectivity. Handling of the oleic substrate, weighing of the catalysts, and charging the reactor were done in air, with exclusion of a glovebox or Schlenk techniques. A catalyst bearing the unsymmetrical N-heterocyclic ligand featuring a thiophene fragment ( Ru-63 ) was selected to offer the best combination between high selectivity and sufficient activity under conditions mimicking oil industry practice. A proof-of-concept large-scale ethenolysis experiment was also done with the selected catalyst to prove its high selectivity at the 1 L scale reaction with a 90% pure non-distilled substrate.

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Valorisation of plant oil derivatives via metathesis reactions: Study of the cross-metathesis of methyl oleate with cinnamaldehyde

Cited by 5 publications

References 26 publications

Equilibrium data for the cross-metathesis of methyl oleate with cinnamaldehyde

Equilibrium data for the cross-metathesis of methyl oleate with cinnamaldehyde

Two highly sensitive fluorescent probes based on cinnamaldehyde with large Stokes shift for sensing of HSO3− in pure water and living cells

Looking for the Noncyclic(amino)(alkyl)carbene Ruthenium Catalyst for Ethenolysis of Ethyl Oleate: Selectivity Is on Target

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