Branched Biobased Diesters with Exceptional Low Temperature and Flow Properties for Use in Lubricant Formulations

Raghunanan, Latchmi; Narine, Suresh S.

doi:10.1021/acssuschemeng.5b01686

Cited by 15 publications

(24 citation statements)

References 40 publications

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“…The viscosity of ester lubricants is highly dependent on molecular weight and amount of branching. As the structure becomes more branched, the molecule becomes bulkier (steric geometric hindrance) which makes it more difficult to bend around and flow over itself compared to its linear counterpart. Based on ISO Viscosity Grade (ISO VG)–ISO 3448 classification, these esters can be categorized as ISO VG 68 lubricant base stocks.…”

Section: Resultsmentioning

confidence: 99%

Excellent Properties of Dimer Fatty Acid Esters as Biolubricant Produced by Catalyst‐ and Solvent‐Free Esterification

Armylisas

Fauzi

Mohd

et al. 2019

Euro J Lipid Sci & Tech

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Currently most technologies available to produce esters require acid or base catalysts for esterification or transesterification reactions. Production of dimerate esters (DE) exhibiting potential as a biolubricant for low temperature applications using catalyst‐ and solvent‐free approaches is presented in this article. Hydrogenated C36 dimer acid and alcohol are reacted under the following conditions: dimer acid/alcohol (1:4.5 molar ratio), 150–200 °C, 24 h, 3Å molecular sieve (15% w/w). The performances of four DE species—dibutyl, dihexyl, di‐(2‐ethylhexyl), and dioctyl dimerate—as lubricant base stocks are evaluated by kinematic viscosity, viscosity index, cloud and pour point (cold flow properties) as well as oxidative stability, and compared with commercial synthetic lubricant base stock and DE, Radialube 7121. High viscosity indexes ranging between 129 and 138 are observed for the synthesized DEs, which are comparable with two commercial base stock, polyalpha olefin (PAO), and polyolester (POE). Significantly low pour point, less than −42 °C, is observed for di‐(2‐ethylhexyl) dimerate attributed to the branching of the side chain. The DEs are categorized as ISO VG 68 based on their viscosity according to ISO 3448 classification and show potential as biolubricant with high viscosity index and excellent cold flow properties. Practical Applications: DFAE obtained have high potential to be used as lubricant base stock for equipment and machinery operating at extremely low temperature.

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Section: Resultsmentioning

confidence: 99%

Excellent Properties of Dimer Fatty Acid Esters as Biolubricant Produced by Catalyst‐ and Solvent‐Free Esterification

Armylisas

Fauzi

Mohd

et al. 2019

Euro J Lipid Sci & Tech

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“…These effects result in less energy loss, reduced friction, and minimized fuel waste. As shown in Table 2, all the biolubricant samples in this work had a kinematic viscosity (KV) of below 100 cSt at 40 °C, which is common for ester-based biolubricants reported in the literature, 4,7,19,26 and thus, these biolubricants could be applied for some ISO viscosity grades (VGs), such as ISO VG 32, VG 46, or VG 68. The decrease in the KV observed in the BL1 (80 cSt) to BL5 (37 cSt) series seemed noticeable as the amount of dihydroxy stearyl ester decreased from 29% in BL1 to a complete absence in BL5.…”

Section: Resultsmentioning

confidence: 88%

Catalytic Conversion of Epoxidized Palm Fatty Acids through Oxirane Ring Opening Combined with Esterification and the Properties of Palm Oil-Based Biolubricants

Ob-eye

Chaiendoo

Itthibenchapong

2021

Ind. Eng. Chem. Res.

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In this work, biolubricants were produced by a two-step catalytic conversion of a palm-based fatty acid mixture. First, the epoxidation of fatty acids with H2O2 solution was performed at 45 °C for 4 h; it was catalyzed by performic acid generated in situ, and the reaction produced epoxidized fatty acids in >98% yield. Subsequently, the ester-based biolubricant product was obtained through a dual process of oxirane ring opening and esterification with 2-ethyl-1-hexanol in a temperature range of 70–130 °C and a reaction time of 2–6 h, with tetrafluoroboric acid used as a catalyst. The optimal synthesis temperature was 110 °C at a reaction time of at least 4 h, as these conditions resulted in 100% conversion. The highest yield of monoesters, one of the main products, was 70.5%. The catalytic performance remained consistent for 6 h, with a total ester-based biolubricant yield of 97.6%. The mono- and di-esters, the main components of the biolubricant, exhibited kinematic viscosities of 46.6 cSt (40 °C) and 7.6 cSt (100 °C), a viscosity index (VI) of 128, and a pour point (PP) of −43 °C. Ketone esters became the main components of the biolubricant products when high-temperature synthesis conditions were used. The viscosity and flow properties of ketone esters were strongly modified: they had an excellent VI of 159 and a PP of 3 °C. Biolubricants with these desirable and tunable properties can potentially be used as a base stock for wide temperature range utilization and as biodegradable-grade lubricants for industrial applications such as hydraulic fluids, turbine oils, and compressor oils.

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“…At the Trent Center for Biomaterials Research, we have already reported on the low temperature flow properties of several series of linear and branched monoesters and diesters with the aim of understanding and predicting the molecular features that result in superior lubricants. − Notably, we have found that branched diesters possess exceptional low temperature and flow properties, whereas the crystallization and melting points of the diesters scale predictably as functions of the total chain length and diol chain length. , Our reports, however, have thus far not systematically reported on the thermal stability of these materials. Similarly, although the thermal stabilities of many biobased materials can be found in the literature, predictable correlations between molecular structures of vegetable oil-derived materials and their thermal stability are still lacking.…”

Section: Introductionmentioning

confidence: 99%

“…The synthesis and structural characterization of the linear (>99% purity) and branched (>95% purity) diesters investigated in this work have already been reported. 15,16,20 All samples were dried to <1% weight loss at 150 °C prior to analysis.…”

Section: ■ Introductionmentioning

confidence: 99%

Engineering Green Lubricants IV: Influence of Structure on the Thermal Behavior of Linear and Branched Aliphatic Fatty Acid-Derived Diesters

Raghunanan

Narine

2016

ACS Sustainable Chem. Eng.

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Fatty acid-derived aliphatic diesters and their branched derivatives are lubricating compounds that demonstrate predictable viscosity temperature profiles and remain fluid at extremely low temperatures. In this work, the influence of molecular structure on the high temperature thermal behavior of several series of aliphatic fatty acid-based diesters was investigated using thermogravimetric analyses (TGA). Evaporation behavior was determined as a function of molecular weight, saturation, symmetry and double bond position, and decomposition behavior as a function of molecular weight, branching, saturation and symmetry. The results revealed that the diol-derived diesters underwent predictable molecular weight-mediated evaporation, and that further refinement of the predicted evaporation temperatures could be obtained by accounting for saturation in the fatty acid moieties. Double bond position and symmetry did not measurably influence the evaporation temperatures of the diesters. Evaporation was successfully suppressed with increasing molecular weight, with the fatty acid chain length and the nature of the branched group being most important in the linear and branched diesters, respectively. Overall, these results are fundamentally significant because they provide the background necessary to make informed changes to molecular structure so as to effect the desired high temperature behavior in renewably sourced specifically engineered materials for lubricant applications.

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Branched Biobased Diesters with Exceptional Low Temperature and Flow Properties for Use in Lubricant Formulations

Cited by 15 publications

References 40 publications

Excellent Properties of Dimer Fatty Acid Esters as Biolubricant Produced by Catalyst‐ and Solvent‐Free Esterification

Excellent Properties of Dimer Fatty Acid Esters as Biolubricant Produced by Catalyst‐ and Solvent‐Free Esterification

Catalytic Conversion of Epoxidized Palm Fatty Acids through Oxirane Ring Opening Combined with Esterification and the Properties of Palm Oil-Based Biolubricants

Engineering Green Lubricants IV: Influence of Structure on the Thermal Behavior of Linear and Branched Aliphatic Fatty Acid-Derived Diesters

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