Chemical, Physical and Tribological Investigation of Polymercaptanized Soybean Oil

Biresaw, Girma; Lansing, James C.; Bantchev, Grigor B.; Murray, Rex E.; Harry-O’kuru, Rogers E.

doi:10.1007/s11249-017-0866-0

Cited by 8 publications

(7 citation statements)

References 36 publications

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“…. The data show that increasing the concentrations of iso ‐oleic and oleic acid up to 10% w/w produced no change in the PP and CP values of the blends, and remained close to the values for neat HOSuO, which were −20 and −6 °C, respectively (Biresaw et al, ), much lower than the values for the neat fatty acids shown in Table . The fact that the blend cold flow values were dominated by that of the HOSuO is in contrast to the blend oxidation stability values where the fatty acids had an influence (Fig.…”

Section: Resultsmentioning

confidence: 53%

“…Both OT and PT decreased with increasing concentration. The observed blend OT and PT values were between those for neat HOSuO, 184 and 197 °C, respectively (Biresaw et al, ), and the values for the neat fatty acids are shown in Table . Thus blending of iso ‐oleic acid in HOSuO will not result in improving oxidation stability but can cause slight deterioration.…”

Section: Resultsmentioning

confidence: 70%

“…It also displays the less‐desirable properties of vegetable oils such as poor thermal oxidation and hydrolytic stability; poor bioresitance; and poor cold flow (high PP and CP) (Biresaw, ). HOSuO was selected as the model biobased base oil for this study because it displays improved oxidation and cold flow properties relative to commodity vegetable oils such as soybean oil (Biresaw et al, ). However, further improvements in these properties of HOSuO are needed for it to be applied in high‐demanding lubrication applications such as in engine oils.…”

Section: Resultsmentioning

confidence: 99%

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Investigation of the Physical and Tribological Properties of Iso‐Oleic Acid

Biresaw

Ngo

Dunn

2018

J Americ Oil Chem Soc

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Oleic acid was isomerized into iso-oleic acid using a modified ferrite zeolite catalyst. The isomerization produced a mixture of iso-oleic acid isomers, with a methyl branching at the double bond, whose position has been randomly distributed along the fatty-acid chain. The effect of isomerization on the physical and tribological properties of iso-oleic acid relative to oleic acid was investigated. The neat fatty acids and their blends in polyalphaolefin (PAO-6) and high-oleic sunflower oil (HOSuO) base oils were used in the investigations. Relative to neat oleic acid, neat iso-oleic acid displayed: higher kinematic viscosity but lower viscosity index (VI) and acid number; lower pour point (PP) and cloud point (CP); better oxidation stability; similar four-ball (4-ball) antiwear friction and wear; and similar 4-ball extreme pressure weld point. Blends (0-10%, w/w) of iso-oleic and oleic acid in PAO-6 displayed the following similar trends with increasing concentration: mildly decreasing kinematic viscosity at 40 and 100 C; increasing VI; lower coefficient of friction; and no change in wear. Blends (0-10%, w/w) of iso-oleic and oleic acid in HOSuO displayed the following similar trends: decreasing oxidation stability with increasing concentration; constant PP and CP with increasing concentration. Keywords Cloud point Á Coefficient of friction (COF) Á High-oleic sunflower oil Á iso-oleic acid Á Kinematic viscosity Á Oleic acid Á Oxidation stability Á Polyalphaolefin Á Pour point Á Viscosity index (VI) Á Wear scar diameter (WSD) Á Zeolite catalyst J Am Oil Chem Soc (2019) 96: 189-199.

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Section: Resultsmentioning

confidence: 53%

Section: Resultsmentioning

confidence: 70%

Section: Resultsmentioning

confidence: 99%

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Investigation of the Physical and Tribological Properties of Iso‐Oleic Acid

Biresaw

Ngo

Dunn

2018

J Americ Oil Chem Soc

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“…Based on GC–MS analysis, the average triglyceride in PMSO contains 2.2 thiol groups, 1.0 double bonds, and 0.76 sulfide cyclic structures before treatment . The structure in Scheme can be used as a close approximation of the average composition of the monomeric triglycerides.…”

Section: Resultsmentioning

confidence: 99%

“…PMSO was used to prepare thermoset networks with high glass temperature for aluminum and powder coatings . PMSO was also investigated for use as a lubricant additive . There is a potential for PMSO to be used as a component of epoxy resins.…”

Section: Introductionmentioning

confidence: 99%

Heat‐ and light‐induced thiol‐ene oligomerization of soybean oil‐based polymercaptan

Bantchev

Vermillion

Lansing

et al. 2018

J of Applied Polymer Sci

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Polymercaptanized soybean oil (PMSO), the product of a thiol-ene reaction between soybean oil and hydrogen sulfide, is a material of interest as a lubricant additive and polymer precursor. We investigated with gel permeation chromatography, nuclear magnetic resonance (one-dimensional and two-dimensional), gas chromatography-mass spectrometry, and viscometry the changes that occur with PMSO upon heating or ultraviolet irradiation. The observed changes were due to a further thiol-ene reaction between the thiol groups and the residual unsaturation. The formation of oligomers was a result of new sulfide bridges. Additionally, tetrahydrothiophene moieties were detected. An almost linear increase of the average molecular weight (MW) and the polydispersity index (PDI) was observed upon heat treatment [number-average MW (M n ) 5 1180 Da, PDI 5 1.32 for PMSO, M n 5 1720 Da, PDI 5 2.17 for PMSO that was heated for 1000 h at 130 8C]. PDI correlated best with the z-average MW. The M n was the best predictor of the viscosity. For samples with close M n , the higher PDI corresponded to a higher viscosity index. V C 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46150.

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