Two series of anionic surfactants (endo‐5‐O‐alkyl isosorbide‐2‐O‐propyl sulfonic acid sodium salt and exo‐2‐O‐alkyl isosorbide‐5‐O‐propyl sulfonic acid sodium salt) with straight alkyl chains (hexyl, octyl, decyl, and dodecyl) were synthesized from isosorbide derived from biomass, through steps of allylation, alkylation, and sulfonation. The selectivity and efficiency of the reactions were optimized by adjusting the solvent, catalyst, reactant molar ratio, and temperature. The product 2‐O‐allyl isosorbide was obtained with a yield of 81% and selectivity of 23:1 (endo:exo), and 2‐O‐alkyl isosorbide was obtained with a yield of 72% and selectivity of 24:1 (exo:endo). The synthesized anionic surfactants were characterized using the critical micelle concentration (CMC), surface activity, emulsion stability, foaming height, and the Turbiscan Stability Index. The CMC decreased with increasing alkyl chain length. The properties of endo form and exo form were compared.
Lubricant additives including zinc dialkyldithiophosphate (ZDDP) containing metal have been widely used due to the advantage of very low cost, but they can generate impurities such as ash. In this work, ZDDP containing metals was partially replaced with bis[3-(dialkyloxyphosphorothionyl) thio-2-methylpropanyloxy] butane (BAP4s) which was synthesized conveniently and effectively from alkanediol without any metal components. Also, the wear resistance property of synthesized BAP4s were studied. Wear scar diameter (WSD) values of BAP4s with butyl, octyl, decyl, dodecyl or tetradecyl groups were also measured by four-ball test. As the length of the alkyl group increased from 4 to 8, the WSD value of BAP4s decreased rapidly from 0.59 to 0.45 mm, but from 8 to 14, the value increased very slowly from 0.45 to 0.50 mm. Thus, among all BAP4s, B8P4 having BAP4 with the octyl group, showed the lowest WSD value. Furthermore, the WSD values were measured in a lubricant base oil mixed with a 0.50 percent concentration (w/w) of either BAP4 or ZDDP. The former was 0.55 mm, and the latter was 0.45 mm. The thermal stability and tribofilm formation peroperty were also measured by thermogravimetric analyzer (TGA) and energy-dispersive X-rays spectroscopy (EDS), respectively.
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