Engineering Green Lubricants I: Optimizing Thermal and Flow Properties of Linear Diesters Derived from Vegetable Oils

Raghunanan, Latchmi; Narine, Suresh S.

doi:10.1021/acssuschemeng.5b01644

Cited by 27 publications

(32 citation statements)

References 41 publications

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“…Our synthesis strategy was as follows. As recently reported by our group, biolubricants with a highly symmetrical structure have excellent lubricating properties such as a viscosity index higher than 140, a pour point lower than −40 °C, good Noack volatility, and oxidation stability . To prepare new and clean biolubricants with a T-shaped structure, we mainly used HMF, a hydrolysate of glucose or fructose, as the main skeleton.…”

Section: Resultsmentioning

confidence: 99%

“…Biomass resources ( e.g. , lipids) can be used to prepare esters, ethers, and hydrocarbon lubricants. , Lipids can be hydrolyzed to long-chain carboxylic acids and alcohols/polyols, which can be subsequently esterified or etherified to prepare mono/polyol esters or ether biolubricants. , Epoxy ether biolubricants can also be prepared by epoxidizing the CC bonds on the lipid structure. , Although these two lubricant production techniques are simple, the high amount of oxygen involved in the process leads to poor low-temperature fluidity and oxidation stability, high acid value, and viscosity indexes lower than 130, which makes the use of precision instruments unsuitable . To prepare full-carbon biolubricants similar to PAO, Zhao et al synthetized fatty alcohols from coconut oil via selective hydrogenation.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

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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“…The strength and distribution of the hydrogen bonding interactions were assessed from the changes in the position/shift and shape of the peaks associated with the proton‐donating (N─H stretch at approximately 3323 cm −1 ) and proton‐accepting moieties (amide I band (C═O) at approximately 1637 cm −1 ) of the ─CONH─ functional group. This approach has been used for diesters and diamides . One can first note the significant widening of the N─H stretching with the increase of the chain length (FWHM from 23 cm −1 for C26 to 41 cm −1 for C36, inset of Figure A) and the associated blue shift of its peak wavenumber (10 cm −1 , Figure B).…”

Section: Resultsmentioning

confidence: 99%

Lipid‐derived monoamide as phase change energy storage materials

et al. 2019

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Summary One of the major shortcomings of current organic phase change materials (PCMs) is their relatively low melting points, typically below 80°C, which limits their integration into thermal energy storage (TES) systems. The present work was aimed at developing lipid‐derived PCMs with increased melting points which would be suitable for TES applications requiring higher melting points without compromising other key properties such as enthalpy. The introduction of an amide group into the structure of linear saturated fatty acids was used as a means to increase intermolecular interactions and therefore crystallization and melting points. A series of six linear monoamides with differing chain length and symmetry about the amide group were investigated for thermal stability, thermal transition, flow behavior, and crystal structure to establish the structure‐property relationships relevant to TES. The presence of the highly polar amide group in the aliphatic fatty acid–derived molecules resulted in notable improvement in performance compared with the analogous monofunctional molecules: Increases in melting points (79°C‐96°C) and high enthalpies of fusion (155‐201 J/g) were recorded. Fundamental relationships between structure, processing, and macroscopic physicochemical properties, never before elucidated, were revealed in the study. The study revealed a step‐like variation of macroscopic properties: a surprising outcome of the competition between intermolecular attractions, symmetry effects, and mass transfer limitations. The predictive structure‐function relationships established in this work will allow the straightforward engineering of monoamide architectures that can extend the range of organic PCMs and deliver thermal properties desirable for TES applications.

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“…While branched alkyl chains cause amorphous solidification at lower temperatures, long linear alkyl chains cause crystallization at higher temperatures. Since low-temperature viscosity has a decisive influence on nucleation and crystal growth, the crystallization behavior is complex [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Low-Temperature Rheology and Thermoanalytical Investigation of Lubricating Oils: Comparison of Phase Transition, Viscosity, and Pour Point

et al. 2021

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According to the ASTM D97, the pour point is the temperature below which petroleum products cease to flow. To evaluate the relevance of pour point measurements for synthetic lubricating oils, we investigated the crystallization, melting temperature and low-temperature flow behavior of one mineral and five synthetic lubricating oils. The classification of three groups emerged from this process. The formation of paraffin crystals in mineral oils (I) below the crystallization temperature causes shear-thinning behavior and a yield point. The crystallization temperature determined in the thermal analysis and rheology correlates well with the pour point. Synthetic lubricating oils, which solidify glass-like (II), exhibit a steady viscosity increase with falling temperature. The temperature at which viscosity reaches 1000 Pas corresponds well to the pour point. Synthetic oils, especially esters, with complex crystallization behavior (III), exhibit supercooling depending on the shear rate and cooling conditions. For these lubricating oils, the pour point provides no information for low-temperature applicability.

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Engineering Green Lubricants I: Optimizing Thermal and Flow Properties of Linear Diesters Derived from Vegetable Oils

Cited by 27 publications

References 41 publications

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

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

Lipid‐derived monoamide as phase change energy storage materials

Low-Temperature Rheology and Thermoanalytical Investigation of Lubricating Oils: Comparison of Phase Transition, Viscosity, and Pour Point

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