Kinetics and mathematical modeling of isomerization of methyl linoleate on ruthenium catalyst. 1. Conjugation and hydrogenation

Doble, Mukesh; Narasimhan, S.; Gadkari, R. G.; Deshpande, V. M.

doi:10.1021/i300018a028

Cited by 13 publications

(5 citation statements)

References 3 publications

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“…The reaction kinetics were found to be further complicated by polymer formation at low solvent concentrations. The kinetics and mathematical modeling of isomerization of methyl linoleate on ruthenium on carbon were also reported by Mukesh et al (1985). It was observed that polymers form in the presence of small amounts of solvent and that isomerization and polymerization are parallel competing reactions.…”

Section: Heterogeneous Transition Metal Catalysis By Metal Particles ...mentioning

confidence: 85%

Strategies for Producing and Incorporating Conjugated Linoleic Acid–Rich Oils in Foods

Shinn

Ruan

Proctor

2017

Annu. Rev. Food Sci. Technol.

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Conjugated linoleic acid (CLA) is in ruminant-derived foods and is known to combat obesity-related diseases. However, CLA levels in a healthy diet are too low to produce a clinical effect. Therefore, CLA has been produced by linoleic isomerization through fermentation and chemical catalysis. Many of these techniques are not practical for food production, but a recent development has enabled production of CLA-rich triglyceride vegetable oils from high linoleic acid oils by a minor modification of conventional food-oil processing techniques. These oils were used to produce common lipid-based food, such as margarine, shortenings, and salad dressings, whose quality was enhanced by the presence of CLA-rich oil and provided a significant CLA source. Meat and egg CLA content and subsequent food quality can also be increased by addition of dietary CLA. However, consumer awareness of CLA benefits needs to increase prior to commercial-scale production of CLA-rich oil.

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Section: Heterogeneous Transition Metal Catalysis By Metal Particles ...mentioning

confidence: 85%

Strategies for Producing and Incorporating Conjugated Linoleic Acid–Rich Oils in Foods

Shinn

Ruan

Proctor

2017

Annu. Rev. Food Sci. Technol.

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“…2.2). On the other hand, the isomerization of methyl linoleate over heterogeneous catalysts has been reported earlier, and the catalysts applied were rhodium and ruthenium on activated carbon [32,33], as well as bimetallic supported ruthenium nickel catalysts [34].…”

Section: Conjugated Linoleic Acids As Health Promoting Agents: Their mentioning

confidence: 84%

Catalytic Transformations for Production of Fine Chemicals and Pharmaceuticals from Wood‐Derived Raw Materials

et al. 2007

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Wood is a valuable raw material for the production of fine chemicals. However, since wood extractives cannot be used directly, their chemical transformation is required. Catalytic processes, in particular, possess the advantages of being environmentally friendly and industrially attractive. The use of sugars for the production of sugar alcohols and terpene transformations, are well known examples. In contrast, catalytic processes for the utilization of fatty acids, phytosterols and lignans as raw materials are very rarely reported. The products obtained from these materials exhibit health promoting properties. The present mini-review is focused on recent activities devoted to catalytic transformations of fatty acids, phytosterols and lignans derived from wood.

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“…15 A mechanism involving hydride transfer could also be operative. Hydride transfer from the solvent has been discussed in the literature 21 in the case of isomerization of methyl linoleate (the methyl ester of linoleic acid) on carbonsupported ruthenium catalyst. Moreover, hydride-transfer reactions, in which the olefin itself acts as a hydrogen donor, might take place on acidic catalysts in the case of hydrocarbons.…”

Section: Discussionmentioning

confidence: 99%

Heterogeneous Catalytic Production of Conjugated Linoleic Acid

Bernas

Kumar

Mäki‐Arvela

et al. 2004

Org. Process Res. Dev.

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Kinetic experiments in selective isomerization of technical grade (∼55%) linoleic acid to cis-9,trans-11-conjugated linoleic acid (B) and trans-10,cis-12-conjugated linoleic (E) acid isomers were performed batchwise at 165 °C over two series of supported metal catalysts, i.e., hydrogen preactivated and nonpreactivated. Activated carbon- and aluminium oxide-supported Ru, Pd, Os, Ir, and Pt−Rh catalysts with 5 wt % metal loading were screened. Catalyst characterization was done by X-ray powder diffraction (XRD), X-ray photoelectron spectroscopy (XPS), scanning electron microscopy−energy-dispersive X-ray analysis (SEM−EDX), temperature-programmed desorption of hydrogen (H2-TPD), direct current plasma atomic emission spectrometry (DCP-AES), and nitrogen adsorption techniques. Over such catalysts, the reaction scheme involves six steps: (1) double bond migration of linoleic acid to conjugated linoleic acid, (2) positional and geometric isomerization of conjugated linoleic acid, (3) double bond hydrogenation of linoleic acid to monoenoic acids, (4) double bond hydrogenation of conjugated linoleic acid to monoenoic acids, (5) positional and geometric isomerization of monoenoic acids, and (6) double bond hydrogenation of monoenoic acids to stearic acid. Over Ru/C catalyst, chemisorbed hydrogen on the metal surface dramatically increased the linoleic acid isomerization rate in a diluted system as an astoichiometric component-enhancing double bond migration but decreased the isomerization rate by promoting deactivation in a solvent-free system. Over Ru/Al2O3 catalyst, on the other hand, dissociated hydrogen increased the isomerization rate for both the diluted and nondiluted systems. The effect of eliminating the solvent was an increase of the turnover frequency (TOF) at 165 °C by a factor of 12 with respect to that shown in a diluted system. At the same conversion carbon- and aluminium oxide-supported Ru catalyst showed higher selectivity toward B and E than carbon-supported Pd, Os, Ir, and Pt−Rh catalysts.

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Kinetics and mathematical modeling of isomerization of methyl linoleate on ruthenium catalyst. 1. Conjugation and hydrogenation

Abstract: extraction of the esterified product over the intact triglycerides.

Cited by 13 publications

References 3 publications

Strategies for Producing and Incorporating Conjugated Linoleic Acid–Rich Oils in Foods

Strategies for Producing and Incorporating Conjugated Linoleic Acid–Rich Oils in Foods

Catalytic Transformations for Production of Fine Chemicals and Pharmaceuticals from Wood‐Derived Raw Materials

Heterogeneous Catalytic Production of Conjugated Linoleic Acid

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