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Sulfurized Methyl Esters of Soya Fatty Acids: Synthesis and Characterization

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Abstract

Soy-based fatty acid methyl ester disulfide (FAME-S2) was synthesized in good yield by oxidation of polymercaptanized soybean oil fatty acid methyl ester (PM-FAME). The chemical structure of FAME-S2 is of interest because of its potential as a biobased multi-functional additive in lubricant formulations. Neat FAME-S2 and their blends (1–10% w/w) in polyalphaolefin (PAO-6) and high oleic sunflower oil (HOSuO) were characterized for its chemical, physical and tribological properties. Blends of FAME-S2 in HOSuO relative to similar blends of PM-FAME displayed higher oxidation onset temperature (> 15 °C) that remained constant with increasing concentration. Evaluation of FAME-S2 as an extreme pressure (EP) additive on a 4-ball tribometer showed increasing weld point (WP) with increasing concentration to a maximum of 220 and 180 kgf in HOSuO and PAO-6, respectively, at 10% w/w concentration. The results indicate that FAME-S2 has both anti-oxidant and EP properties and can be applied as a multi-functional biobased additive in lubricant formulation. This work demonstrates an encouraging progress towards the development of effective biobased lubricant additives.

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Acknowledgements

The authors are very grateful to Ms. Linda Cao, Ms. Linda Manthey, Mr. Dan Knetzer and Dr. Karl Vermillion for their technical assistance.

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Authors and Affiliations

  1. Bio-Oils Research Unit, Agricultural Research Service, United States Department of Agriculture, National Center for Agricultural Utilization Research, 1815 N. University Street, Peoria, IL, 61604, USA

    Girma Biresaw, Grigor B. Bantchev, James Lansing, Rogers E. Harry-O’kuru & Yunzhi Chen

  2. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, China

    Yunzhi Chen

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  1. Girma Biresaw
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  2. Grigor B. Bantchev
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  3. James Lansing
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  4. Rogers E. Harry-O’kuru
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Correspondence to Girma Biresaw.

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Biresaw, G., Bantchev, G.B., Lansing, J. et al. Sulfurized Methyl Esters of Soya Fatty Acids: Synthesis and Characterization. Tribol Lett 68, 61 (2020). https://doi.org/10.1007/s11249-020-01292-y

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