Further Observations on the Guerbet Reaction

Weizmann, Ch.; Bergmann, Ernst D.; Sulzbacher, M.

doi:10.1021/jo01147a010

Cited by 28 publications

(10 citation statements)

References 1 publication

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“…94,97,100 Finally, at least one of both reacting alcohols requires an α-methylene group in order to undergo Guerbet condensation, a requisite for the formation of the aldol condensation product, which cannot form should both alcohols lack an α-hydrogen atom. 98 Together with the specific α-alkyl branching of Guerbet alcohols, these findings support an aldol-type coupling mechanism. An Ellingham-type plot in Fig.…”

Section: Reaction Mechanisms and Thermodynamic Considerationsmentioning

confidence: 69%

“…This mechanism involving aldolization is supported by several arguments. Intermediate products of the pathway are often observed 92,[94][95][96][97][98] and can be reduced to the product alcohol under the same conditions. 70,96 The conditions applied in the Guerbet reaction are suitable for aldol condensation.…”

Section: Reaction Mechanisms and Thermodynamic Considerationsmentioning

confidence: 99%

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Review of catalytic systems and thermodynamics for the Guerbet condensation reaction and challenges for biomass valorization

Gabriëls

Hernández

Sels

et al. 2015

Catal. Sci. Technol.

243

233

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The Guerbet condensation reaction is an alcohol coupling reaction that has been known for more than a century. Because of the increasing availability of bio-based alcohol feedstock, this reaction is of growing importance and interest in terms of value chains of renewable chemical and biofuel production. Due to the specific branching pattern of the alcohol products, the Guerbet reaction has many interesting applications. In comparison to their linear isomers, branched-chain Guerbet alcohols have extremely low melting points and excellent fluidity. This review provides thermodynamic insights and unravels the various mechanistic steps involved. A comprehensive overview of the homogeneous, heterogeneous and combined homogeneous and heterogeneous catalytic systems described in published reports and patents is also given. Technological considerations, challenges and perspectives for the Guerbet chemistry are discussed.

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Section: Reaction Mechanisms and Thermodynamic Considerationsmentioning

confidence: 69%

Section: Reaction Mechanisms and Thermodynamic Considerationsmentioning

confidence: 99%

Review of catalytic systems and thermodynamics for the Guerbet condensation reaction and challenges for biomass valorization

Gabriëls

Hernández

Sels

et al. 2015

Catal. Sci. Technol.

243

233

View full text Add to dashboard Cite

show abstract

“…16 Finally, Weizmann et al confirmed the requirement of a hydrogen atom on the α-carbon as a prerequisite for the aldol condensation step through feeding different types of alcohols over the Guerbet reaction catalyst. 22 Guerbet reaction catalysts must be multifunctional, having metal or electron-deficient metal oxide surface sites for dehydrogenation and hydrogenation, and basic and acidic sites for aldol condensation. heterogeneous catalysts to date include Mg−Al mixed oxides, 17,20,23−32 hydroxyapatites (HAPs), 33−37 metal-containing CeO 2 supports, 1,38,39 and other metal combinations.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Gines et al included 13 C-labeled acetaldehyde in their ethanol feed and noticed an improved n -butanol yield through incorporation of the labeled carbon atoms . Finally, Weizmann et al confirmed the requirement of a hydrogen atom on the α-carbon as a prerequisite for the aldol condensation step through feeding different types of alcohols over the Guerbet reaction catalyst …”

Section: Introductionmentioning

confidence: 99%

Condensed-Phase Ethanol Conversion to Higher Alcohols over Bimetallic Catalysts

Nezam

Zak

Miller

2020

Ind. Eng. Chem. Res.

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The catalytic condensation of ethanol to n-butanol and higher alcohols, known collectively as Guerbet reactions, has attracted attention in recent years as ethanol becomes increasingly available as a biorenewable feedstock. Results are presented here for the continuous, condensed-phase conversion of ethanol to higher alcohols using Ni/La2O3/γ-Al2O3 catalysts and for catalysts containing a second metal (Cu, Co, Pd, Pt, Fe, Mo) in addition to nickel. Detailed characterization of the catalyst surface and bulk properties has been carried out and is correlated to catalyst activity and selectivity. The best results obtained for nickel catalysts are a selectivity to higher alcohols of 75–80% and a turnover frequency of 200 mol ethanol/mol Ni site/h at 230 °C. The addition of cobalt nearly doubles the ethanol conversion rate relative to Ni alone, with only a slight reduction in higher alcohol selectivity. Results of catalyst characterization, a simple kinetic model, and experiments with reaction intermediates support the initial dehydrogenation of ethanol as the rate-limiting step of the condensed-phase reaction.

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“…The Guerbet reaction was studied by using various catalysts including Raney Ni [11], U.O.P. nickel [12], copper-bronze [17], copper chromite, manganese chromite, copper-magnesium chromite, zinc chromite. Various basic reagents like magnesium oxide [18], potassium carbonate, calcium carbonate, sodium carbonates have been tried [11].…”

Section: Introductionmentioning

confidence: 99%

Synthetic Base Stock Based on Guerbet Alcohols

Waykole¹,

Bhowmick²,

Pratap³

2014

J Americ Oil Chem Soc

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Guerbet (b branched) alcohols of varying chain length of even carbon numbers were synthesized by using single linear fatty alcohols ranging from 1-octanol to 1-dodecanol. All Guerbet alcohols having fewer than 28 carbon atoms and are liquid at 0°C due to b branching. Synthetic base oils were prepared by reacting commonly available unsaturated fatty acids and dicarboxylic acids with Guerbet alcohols using p-toluenesulfonic acid as a catalyst. These base oils were characterized by physical and tribological properties like viscosity, viscosity index, pour point, flash point, wear scar, weld load, coefficient of friction etc. and compared with commercially available 150 and 500 N base oils.

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Further Observations on the Guerbet Reaction

Cited by 28 publications

References 1 publication

Review of catalytic systems and thermodynamics for the Guerbet condensation reaction and challenges for biomass valorization

Review of catalytic systems and thermodynamics for the Guerbet condensation reaction and challenges for biomass valorization

Condensed-Phase Ethanol Conversion to Higher Alcohols over Bimetallic Catalysts

Synthetic Base Stock Based on Guerbet Alcohols

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