Thermal alteration of oleic acid in the presence of clay catalysts with co‐catalysts

Nakano, Yasuhiko; Foglia, Thomas A.; Kohashi, Hitoshi; Perlstein, Theodore; Serota, Samuel

doi:10.1007/bf02541752

Cited by 20 publications

(4 citation statements)

References 11 publications

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“…[45][46][47] As MoBUFA are interesting compounds as lubricants and for their use in cosmetics, 48 there exists a need for more selective processes. While some clays give moderate yields, [49][50][51][52] zeolites are used with more success [53][54][55][56][57][58] due to their relative small channels and pores. 47 As the zeolite pores are already blocked at the beginning of the reaction due to cokes formation, 47 the isomerisation takes place solely at the entrance of the micropores (Fig.…”

Section: Conversion Of Fats and Oilsmentioning

confidence: 99%

Potential and challenges of zeolite chemistry in the catalytic conversion of biomass

et al. 2016

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Increasing demand for sustainable chemicals and fuels has pushed academia and industry to search for alternative feedstocks replacing crude oil in traditional refineries. As a result, an immense academic attention has focused on the valorisation of biomass (components) and derived intermediates to generate valuable platform chemicals and fuels. Zeolite catalysis plays a distinct role in many of these biomass conversion routes. This contribution emphasizes the progress and potential in zeolite catalysed biomass conversions and relates these to concepts established in existing petrochemical processes. The application of zeolites, equipped with a variety of active sites, in Brønsted acid, Lewis acid, or multifunctional catalysed reactions is discussed and generalised to provide a comprehensive overview. In addition, the feedstock shift from crude oil to biomass involves new challenges in developing fields, like mesoporosity and pore interconnectivity of zeolites and stability of zeolites in liquid phase. Finally, the future challenges and perspectives of zeolites in the processing of biomass conversion are discussed.

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Section: Conversion Of Fats and Oilsmentioning

confidence: 99%

Potential and challenges of zeolite chemistry in the catalytic conversion of biomass

et al. 2016

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“…Several research groups have reported that UFA such as oleic acid (OA) can be converted to bc-isomers in the presence of clay catalysts such as bentonite and montmorillonite. In 1983, Foglia et al [1] reported that OA could be converted to a mixture of methyl bc-FA at up to 50% conversion when using a bentonite clay and dichloroethane as a co-catalyst [1,2]. In 1994, Neuss et al [3] reported that, with a montmorillonite clay catalyst in combination with an active carbon, sunflower oil FA/ esters could be converted to bc-isomers in yields between 30 and 40%.…”

Section: Introductionmentioning

confidence: 99%

Zeolite‐catalyzed isomerization of oleic acid to branched‐chain isomers

Ngo

Núñez

Lin

et al. 2007

Euro J Lipid Sci & Tech

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Zeolite-catalyzed isomerization of oleic acid to branched-chain isomers*Branched-chain (bc) saturated fatty acids (SFA) have potential as oleochemical intermediates since they have better oxidative stability than linear unsaturated fatty acids (UFA) and have better low-temperature properties than linear SFA. Previous studies in converting UFA to bc-FA using clay catalysts have resulted in only modest yields and conversions. Recent reports, however, have suggested that certain zeolites can be effective catalysts for converting UFA to bc-FA in higher yields and conversions. In this work, we examined the scope and potential of the zeolite-catalyzed synthesis of bc-FA starting from readily available monounsaturated linear FA. Our results show that common UFA such as oleic acid can be converted to bc-isomers using modified Ferrierite zeolite catalysts with high conversions (98%) and high selectivity (85%) and that the zeolite catalysts are reusable for at least three cycles. The positions of branching (methyl) on the FA chain were determined from the GC-MS spectra of the picolinyl esters of the bc-FA.

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“…Spiteller et al examined the positions of the methyl branches obtained from the monomeric fraction of the dimerization of pure oleic acid [18][19][20]. The formation of the methylbranched fatty acids can be rationalized by the protonation of the C,C double bond and following reactions of the adduct carbenium ions with other products of the dimerization, by transfer of a hydride ion [18] on the one hand or by cyclization and following ring opening of the three-membered ring carbocation intermediate on the other hand [21]. Isostearic acids with a branching at C2-C5 were not observed because carbenium ions with the positive charge in these positions cyclize to give the respective lactones [18].…”

Section: Heterogeneously Catalyzed Isomerization Reactionsmentioning

confidence: 99%

Synthesis of alkyl‐branched fatty acids

Biermann

Metzger

2008

Euro J Lipid Sci & Tech

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Alkyl-branched fatty compounds are of interest for industrial products in the cosmetics and lubricant areas. In this review, clay-and zeolite-catalyzed isomerizations of unsaturated fatty compounds, especially of oleic acid, are discussed. While clay-catalyzed reactions give most complex mixtures of dimeric fatty acids and of monomeric so-called "isostearic acid", the zeolite-catalyzed process yields preferentially an isomeric mixture of isostearic acids having the methyl branch on the 8-14 positions of the alkyl chain. Synthetically useful additions of alkyl radicals can only be performed on o-unsaturated fatty compounds, whereas perfluoroalkyl iodides were added to fatty compounds with terminal as well as internal double bonds using electron transfer-initiated radical addition reactions. Electrophilic additions of alkyl carbenium ions generated by decomposition of alkyl chloroformates by ethylaluminum sesquichloride give welldefined alkyl-branched oleochemicals with good yields.

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Thermal alteration of oleic acid in the presence of clay catalysts with co‐catalysts

Cited by 20 publications

References 11 publications

Potential and challenges of zeolite chemistry in the catalytic conversion of biomass

Potential and challenges of zeolite chemistry in the catalytic conversion of biomass

Zeolite‐catalyzed isomerization of oleic acid to branched‐chain isomers

Synthesis of alkyl‐branched fatty acids

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