Synthetic Base Stock Based on Guerbet Alcohols

Waykole, Chetan; Bhowmick, D. N.; Pratap, Amit P.

doi:10.1007/s11746-014-2484-4

Cited by 10 publications

(3 citation statements)

References 11 publications

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“…More recently, Waykole and co-workers 137 have prepared Guerbet alcohols by self-condensation of linear fatty alcohols ranging from n-octanol to n-dodecanol. Instead of a transition metal catalyst, heptanal was added to the reaction medium functioning as a carbonyl promoter.…”

Section: Catalysis Science and Technology Minireviewmentioning

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

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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: Catalysis Science and Technology Minireviewmentioning

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

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“…The branched structure of methylenealkanes offers hope for superior viscosity characteristics of their derivatives, for example, esters. The prospects of structurally-similar Guerbet alcohols in the synthesis of the Group 5 oils have been demonstrated earlier [38][39][40]. Thus, the synthetic approach to obtain homologs of these alcohols using methylenealkanes seems to be highly prospective, bearing in mind only moderate product yields in the dimerization of 1-alkanols according to a Guerbet reaction [41,42] (Scheme 2a).…”

Section: Introductionmentioning

confidence: 95%

Methylenealkane-Based Low-Viscosity Ester Oils: Synthesis and Outlook

et al. 2020

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Both Group 4 poly-α-olefin (PAO) and Group 5 ester oil basestocks are used in formulations of synthetic engine oils, transmission fluids, and lubricants with leading characteristics such as low viscosity (providing fuel saving), high stability, and environmental safety. The modern technologies of the production of PAOs use catalytic oligomerization of α-olefins, which is complicated by the formation of low-molecular-weight α-olefin dimers (methylenealkanes) as imminent side products. The use of methylenealkanes as raw materials for the synthesis of Group 5 base stocks appears to be highly promising. In the present work, we report the use of methyl 3-butylnonanoate and methyl 3-hexylundecanoate, the products of catalytic methoxycarbonylation of hex-1-ene and oct-1-ene dimers, in the synthesis of two series of branched isomeric esters. These esters demonstrated excellent rheological behavior and may be considered as low-viscosity engine oils with leading characteristics.

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“…The so-called Guerbet alcohol − is a primary alcohol with asymmetric double alkyl chains, where one alkyl chain is longer than the other by two carbon atoms. In general, this structure is similar to that of dialkyl glyceryl ether, and the Guerbet alcohol is therefore good material for deriving double-chain single-head surfactants.…”

Section: Introductionmentioning

confidence: 99%

Performances of Guerbet Alcohol Ethoxylates for Surfactant–Polymer Flooding Free of Alkali

Yan

Cui

et al. 2017

Energy Fuels

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Two series of double-chain single-head nonionic surfactants, Guerbet alcohol ethoxylates (C m GA–E n ; m = 16 and 20, n = 5.7–24.0), were synthesized, and their performances as surfactants for surfactant–polymer (SP) flooding free of alkali were evaluated. The products have relatively low critical micelle concentrations [(6.8 × 10–7)–(1.0 × 10–5 mol/L)] and a wide range of surface tensions at the critical micelle concentration (γcmc) values (30.3–38.0 mN/m) at 25 °C, depending on both the alkyl-chain length and the number of ethylene oxide (EO) units. When used alone, these nonionic surfactants are not efficient for reducing crude oil/connate water interfacial tension (IFT), but their binary mixtures with a highly hydrophobic zwitterionic surfactant, didodecylmethyl hydroxylpropyl sulfobetaine (diC12HSB), are very efficient in reducing Daqing crude oil/connate water IFTs. Ultralow IFTs can be achieved in a wide total concentration range (0.3–10 mM) at 45 °C, and the low limit (0.3 mM) can be further reduced to 0.15 mM by adding an anionic surfactant, α-olefin sulfonate (AOS), to the binary mixtures at a small mole fraction (0.1). Both the binary and ternary mixtures display good resistance against adsorption by Daqing sandstone, and when dissolved in connate water, they prefer to keep the negatively charged rock surface water-wet and produce a crude-oil-in-water emulsion. In addition, the incorporation of AOS into the binary mixtures was found to be beneficial for preventing crystallization of zwitterionic surfactant and flocculation of nonionic surfactants, as reported previously. Comparatively, for SP flooding free of alkali, the Guerbet alcohol ethoxylates are as excellent as the glyceryl ether ethoxylates, nonionic surfactants with a similar double-alkyl single-head structure, but are far superior to the conventional nonionic surfactants with monoalkyl single-head structures.

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Synthetic Base Stock Based on Guerbet Alcohols

Cited by 10 publications

References 11 publications

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

Methylenealkane-Based Low-Viscosity Ester Oils: Synthesis and Outlook

Performances of Guerbet Alcohol Ethoxylates for Surfactant–Polymer Flooding Free of Alkali

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