Alkylated Naphthalenes as High-Performance Synthetic Lubricating Fluids

Hourani, M. J.; Hessell, E. T.; Abramshe, Richard A.; Liang, James

doi:10.1080/10402000601105581

Cited by 26 publications

(4 citation statements)

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“…Compared to the mineral oil being a complex mixture of petroleum-refined liquid hydrocarbons, synthetic base oils have received much more attention because their chemical component is simple and their molecule structure can be rationally designed. Among synthetic base oils, alkylated naphthalene stands out due to its excellent solubility with additives and thermo-oxidative stability related to the combination of naphthalene ring and alkane structure. − It has been successfully applied in many fields, for instance, gear oil, bearing grease, hydraulic oil, heat conduction oil, and automotive lubricant oil …”

Section: Introductionmentioning

confidence: 99%

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Decalin/Naphthalene Alkylation Using an Ionic Liquid Catalyst to Produce a Novel Base Oil and Its Tribological Properties

Zuo,

Han,

Zhao

et al. 2024

Ind. Eng. Chem. Res.

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Alkylnaphthalenes as one of the important lubricating base oils were generally produced by alkylation of naphthalene with olefins, halides, or alcohols. Herein, a totally different alkylating reagent of decalin was studied to react with naphthalene for producing cycloalkylnaphthalene base oils by using the ionic liquid Et 3 NHCl-AlCl 3 as the catalyst. The success for alkylation is attributed to the high reaction activity of the tertiary C−H in decalin under an ionic liquid catalyst. The effect of the two isomers of decalin and reaction conditions on alkylation results was investigated in detail, and it was found that cis-decalin exhibited much higher reactivity than trans-decalin in alkylation. The structure and component of synthetic fluid were confirmed, and their physicochemical properties were tested. Tribological test results demonstrated that cycloalkylnaphthalene exhibits superior friction reduction and antiwear properties compared with commercial alkylated naphthalene base oil AN8.

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Section: Introductionmentioning

confidence: 99%

“…Previous studies revealed that the properties of alkylated aromatics hinge on the number, length, and structure of their side-chain alkyl groups. 1 As lubricating oils, linear alkylated aromatic has been widely researched, while the synthesis and properties of cycloalkylated naphthalene are rarely reported.…”

Section: Introductionmentioning

confidence: 99%

Decalin/Naphthalene Alkylation Using an Ionic Liquid Catalyst to Produce a Novel Base Oil and Its Tribological Properties

Zuo,

Han,

Zhao

et al. 2024

Ind. Eng. Chem. Res.

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“…Even so, the disadvantages of 5P4E, such as relatively poor tribological properties and a high pour point, limit its applications [26]. Despite this, the alkylation of aromatic compounds could potentially generate compounds suitable as lubricants [27]; thus, the tribological properties of PPEs should be improved.…”

Section: Introductionmentioning

confidence: 99%

Alkylated Polyphenyl Ethers as High-Performance Synthetic Lubricants

et al. 2022

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Lubricants exhibiting both thermal and chemical stability that consequently generate less hydrogen during friction are required to avoid the hydrogen embrittlement of moving mechanical components. The present work studied the effects of the length and number of alkyl chains on the tribological properties of polyphenyl ethers (PPEs), which feature good thermal and radiation resistance. PPEs were found to have much lower friction coefficients compared with a poly-alpha-olefin and alkyldiphenyl ether, and the effect of the running-in process on friction appeared to be negligible. The formation of polymers on the friction track evidently decreased the friction coefficients of the lubricants and the wear rates were almost zero for all the PPEs, indicating excellent anti-wear properties. Analyses with a quadrupole mass spectrometer connected to a friction tester under vacuum indicated negligible hydrogen generation from 4P2E, which had no alkyl chains, after the running-in. R1-4P2E, having a C16H33 chain, showed hydrogen desorption similar to that of the alkyldiphenyl ether, which had a C18H37 alkyl chain. R2-4P2E, with two C16H33 chains, produced significant hydrogen, but with a long induction period; thus, it provided good wear protection. Although alkyl chains increased the risk of hydrogen generation, PPEs with such chains may have applications as standard lubricants.

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“…Shubkin [4] introduced PAOs for highperformance lubrication and determined the pour point of several PAOs differing in molecular weight and viscosity. With increasing molecular weight and viscosity, the pour point increases from −70 to −20 • C. Tsvetkov [5] stated that PAOs with molecular weights ranging from 453 to 1056 g mol −1 and kinematic viscosities at 100 • C ranging from 5 to Another lubricating oil type for high-performance lubrication are alkylated naphthalenes, introduced by Hourani et al [6] as well as Hessel and Abramshe [7]. They state that the pour point of naphthalenes rises with increasing substitution and branching [6,7].…”

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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Alkylated Naphthalenes as High-Performance Synthetic Lubricating Fluids

Cited by 26 publications

References 1 publication

Decalin/Naphthalene Alkylation Using an Ionic Liquid Catalyst to Produce a Novel Base Oil and Its Tribological Properties

Decalin/Naphthalene Alkylation Using an Ionic Liquid Catalyst to Produce a Novel Base Oil and Its Tribological Properties

Alkylated Polyphenyl Ethers as High-Performance Synthetic Lubricants

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

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