Branched Bio‐Lubricant Base Oil Production through Aldol Condensation

Norton, Angela M.; Liu, Sibao; Saha, Basudeb; Vlachos, Dionisios G.

doi:10.1002/cssc.201901838

Cited by 30 publications

(28 citation statements)

References 18 publications

(36 reference statements)

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“…Their properties can outperform commercial products. 20,[28][29][30] Fig. 5a shows a pathway to renewable base oils using alkylfurans and fatty 20,[28][29][30] Fig.…”

Section: Reaction Chemistry and Engineering Perspectivementioning

confidence: 99%

“…20,[28][29][30] Fig. 5a shows a pathway to renewable base oils using alkylfurans and fatty 20,[28][29][30] Fig. 6 Strategy to produce branched benzene lubricant (BBL) base oils and branched cyclic lubricant (BCL) base oils via Brønsted acid-catalyzed hydroxyalkylation/alkylation (HAA) of lignin-derived monomers (hydroxyphenyls, guaiacols, and syringols) with an aldehyde and the and hydrodeoxygenation (HDO) of the BBL product, respectively.…”

Section: Reaction Chemistry and Engineering Perspectivementioning

confidence: 99%

“…5 (a) Production of three classes of lubricants from alkyl furans and long-chain aldehydes. (b) Examples of base oil lubricant structures from different chemistry paths and starting chemicals 20,[28][29][30].…”

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confidence: 99%

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Accelerating manufacturing for biomass conversion via integrated process and bench digitalization: a perspective

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“…Their properties can outperform commercial products. 20,[28][29][30] Fig. 5a shows a pathway to renewable base oils using alkylfurans and fatty 20,[28][29][30] Fig.…”

Section: Reaction Chemistry and Engineering Perspectivementioning

confidence: 99%

Section: Reaction Chemistry and Engineering Perspectivementioning

confidence: 99%

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Accelerating manufacturing for biomass conversion via integrated process and bench digitalization: a perspective

et al. 2022

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“…Starting with cellulose or hemicellulose-derived small molecules containing furan rings or short-chain carboxylic acids, researchers have achieved C–C coupling and promoted carbon chain growth by a number of chemistries including aldol condensation, − ketonization, hydroxyalkylation/alkylation (HAA), reductive etherification reaction, acylation reaction, pinacol coupling, and Diels–Alder reaction . Thus, highly branched specific structural intermediates have been synthetized and subsequently used to prepare biolubricants by hydrogenation/hydrodeoxygenation.…”

Section: Introductionmentioning

confidence: 99%

Production of Highly Symmetrical and Branched Biolubricants from Lignocellulose-Derived Furan Compounds

Chen

Zhao

2021

ACS Sustainable Chem. Eng.

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With the aim to prepare a high-performance biolubricant equivalent to poly-α-olefin, we created a T-shaped biolubricant base oil by multisite C−C coupling of small molecules containing furan rings. The aldehyde and hydroxyl groups on cellulose-derived 5-hydroxymethylfurfural (HMF) were used as active functional groups. Activated carbocations were generated via solvent-free protonation of the aldehyde and hydroxyl groups on the acid. Then, one-pot triple C−C couplings were achieved to extend the carbon chain through hydroxyalkylation/alkylation with hemicellulosederived C 8 −C 10 2-alkylfuran. Highly branched C 30 , C 33 , and C 36 precursors with furan rings were obtained (yield: 91−93%). Side reactions included self-polymerization of alkylfuran and ring-opening isomerization of furan rings. In situ Fourier transform infrared spectroscopy and kinetic studies showed that the reaction between HMF and alkylfuran conformed to firstorder reaction kinetics, with a reaction constant (k) of 0.2 min −1 and an activation energy (E a ) of 61.2 kJ/mol. The obtained precursor either underwent selective hydrogenation of the furan rings to yield a highly branched epoxy ether biolubricant or was converted into a highly branched and symmetric T-shaped full-carbon biolubricant by complete hydrodeoxygenation. This strategy provides a simple and feasible solution for the ingenious design of long-chain symmetrical biolubricant alkanes through one-pot multisite C−C coupling of small furan ring molecules starting from lignocellulose. In addition, the proposed route for the development of high-quality biolubricant base oil is highly innovative and economically feasible.

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“…Liu et al [12,13] prepared C 30 intermediate by CÀ C coupling with substituted furan and fatty aldehyde using an acidic ion exchange resin as catalyst, which was subsequently hydrodeoxygenated (by IrRe/SiO 2 or IrMo/SiO 2 ) to obtain biolubricant base oil. Later, the same research team condensed furanaldehyde and long-chain ketones to C 33 ketone-furan ring intermediates, [14] or the hydroxyalkylation of alkane furans and long-chain alkenals to C 25 -C 33 intermediates, which were then subjected to HDO reaction via IrRe/SiO 2 to obtain biolubricant base oil. [15] The synthesis of cycloalkane biolubricant base oil used the self-condensation of long-chain methyl ketone catalyzed by magnesium aluminum hydrotalcite followed by HDO.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Branched Biolubricant Base Oil from Oleic Acid

Chen

Zhao

2020

ChemSusChem

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The mature manufacturing of synthetic lubricants (poly-αolefins, PAO) proceeds through oligomerization, polymerization, and hydrogenation reactions of petrochemical ethylene. In this work, we utilize the inexpensive bio-derived oleic acid as raw material to synthesize a crotch-type C 45 biolubricant base oil via a full-carbon chain synthesis without carbon loss. It contains several cascade chemical processes: oxidation of oleic acid to azelaic acid (further esterification to dimethyl azelate) and nonanoic acid (both C 9 chains). The latter is then selectively hydrogenated to nonanol and brominated to the bromo-Grignard reagent. In a next step, a C 45 biolubricant base oil is formed by nucleophilic addition (NPA) of excessive C 9 bromo-Grignard reagent with dimethyl azelate, followed by subsequent hydrodeoxygenation. The specific properties of the prepared biolubricant base oil are almost equivalent to those of the commercial lubricant PAO6 (ExxonMobil). This process provides a new promising route for the production of valueadded biolubricant base oils.

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Branched Bio‐Lubricant Base Oil Production through Aldol Condensation

Abstract: This is the author manuscript accepted for publication and has undergone full peer review but has not been through the copyediting, typesetting, pagination and proofreading process, which may lead to differences between this version and the Version of Record.

Cited by 30 publications

References 18 publications

Accelerating manufacturing for biomass conversion via integrated process and bench digitalization: a perspective

Accelerating manufacturing for biomass conversion via integrated process and bench digitalization: a perspective

Production of Highly Symmetrical and Branched Biolubricants from Lignocellulose-Derived Furan Compounds

Synthesis of Branched Biolubricant Base Oil from Oleic Acid

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