• Applied Chemistry for Engineering
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• v.23 no.4
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• pp.421-427
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• 2012

To improve the lubricity of ultra low sulfur diesel, vegetable oil-based alkanol amide derivatives were prepared and their lubricity properties were studied. To synthesize the alkanol amides, we conducted the amidation reaction of diethaolamine High Frequency Reciprocating Rig (HFRR) and the fatty acid methyl esters, obtained by the continuous transesterification of methanol and several vegetable oil, such as soybean oil, palm oil and coconut oil. The synthesized amides were soluble in ultra low sulfur diesel in the concentration range of ca. 1 wt%; the lubricating properties of ultra low sulfur diesel containing 120 ppm of amides were measured using an HFRR method. It was found that the wear scar diameter in the pure ultra low sulfur diesel decreased significantly from 581 ${\mu}m$ to 305~323 ${\mu}m$ upon the addition of the amides, indicating that lubricating properties of the diesel were improved. On the other hand, the types of vegetable oils did not affect the wear scar diameters, implying that lubricating properties of the diesel did not depend strongly on the structures of alkyl groups of alkanol amide derivatives. When we measured the lubricating properties of the one type of diesels containing various amounts of alkanol amide, we observed that the wear scar diameter decreased drastically with increasing the amide concentration, meaning that the lubricity improved with the amide concentration.

• Applied Chemistry for Engineering
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• v.19 no.1
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• pp.51-58
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• 2008

A series of oleic acid esters containing mercaptobenzothiazole and dialkylenedithiocarbamate, which are potential environmentally friendly lubricating grease additives, were synthesized as 90% yield through several method such as nucleophilic substitution of dialkyl amine and carbon disulfide, reduction reaction, and condensation reaction. The structures of the additives were confirmed by $^1H$-NMR, FT-IR and EA analysis. The additives (1 wt%) were soluble in 100 N BO except C4-DTC-OE and soluble in soybean oil. The tribological properties as lubricating additives in 100 N BO were evaluated using 4-ball tester and the results showed as follows: Bz-thia-OE < C4-DTC-OE < Pyrro-DTC-OE < C8-DTC-OE. Whereas, the 4-ball anti-wear properties were not shown in soybean oil.

• Applied Chemistry for Engineering
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• v.24 no.5
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• pp.530-536
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• 2013

Vegetable oil-based dimer acid derivatives were prepared through a two-step procedure and their lubricating properties for diesel fuel were evaluated using high frequency reciprocating ring (HFRR) method to investigate wear scar diameter (WSD). Diels-Alder reaction at an elevated temperature transformed fatty acid to dimer acid, subsequently converted into dimer acid derivatives by esterification with methanol. It should be noted that the derivatives were dissolved well in diesel oil up to 1 wt%. After adding 120 ppm of the derivatives to pure diesel, the WSD significantly decreased to $300{\sim}05{\mu}m$, compared to $552{\mu}m$ of WSD in pure diesel. Dimer acid derivatives having carboxylic acid show superb in lubricating property which does not depend on the alkyl group in the derivatives.

• Tribology and Lubricants
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• v.31 no.5
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• pp.195-204
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• 2015

Several researches are focused on improving the value of fine chemicals based on biomass resources due to environmental and other concerns associated with the use of petroleum-based products. Therefore, the synthesis and application of estolides derived from plant-based waste oil materials and their application as lubricants and as processing oil for butyl rubber products have been studied. Four kinds of estolide were prepared with conversions of 71~92% over 24h using various vegetable oils, as determined by size exclusion chromatography (SEC) and nuclear magnetic resonance (NMR) spectroscopy. FT-IR spectroscopy determines the esterification of estolides using 2-ethylhexyl alcohol. The estolides have iodine values of 35~90, α-ester/α-acid ratios of 0.45~0.55, and total acid number of 114~134 mg KOH g^–1. Four ball wear tests show that the wear scar diameters (WSDs) of estolides as base oil significantly decreased to 0.328~0.494 mm, compared to WSDs of 0.735 and 0.810 mm of WSD for 150N and Yubase 6, respectively, as general base oil. Thus, the estolides have better wear resistance and satisfying design objectives for the engineering of a variety of lubricant base oils.

• Tribology and Lubricants
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• v.30 no.5
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• pp.256-264
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• 2014

Enhancing the value of fine chemicals based on biomass resources is an important objective for addressing environmental and other concerns such as demand for renewable or green products, as well as from the political perspective to reduce dependence on fossil feedstock associated with the use of petroleum-based products. Based on these considerations, we studied the synthesis of estolide using waste plant-based oil materials and their application as lubricants and pour point depressants. Five estolides were prepared by varying molar ratio of palmitic acid (PA) to oleic acid (OA) using a reaction time of 48 h. The estolides were characterized by size exclusion chromatography (SEC) and nuclear magnetic resonance (NMR). The isolated yields were in the range of 57-78 % and purity was 93-97%, showing iodine values of 18.2-37.8, total acid numbers (TANs) of 75.6-94.2 mg KOH/g and estolide numbers (ENs) of 1.2-1.8. Increasing the ratio of OA to PA in the synthesis decreased the kinematic viscosity and clouding point of the estolides. Four ball wear test of the estolides as a base oil demonstrated that the wear scar diameter (WSD) of the estolides was significantly lower (0.320-0.495 mm) than the WSD of general base oils such as 150N and Yubase (0.735 and 0.810 mm, respectively), indicating better wear resistance of the estolides. However, the lubricant property was found to be independent of the amount of OA in the estolides. These new materials are prospective candidates for application as a lubricant base oil.

• Applied Chemistry for Engineering
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• v.22 no.2
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• pp.196-202
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• 2011

In this paper, a series of alkyl succinic acid esters for base oil were synthesized by condensation reaction of succinic anhydride and fatty alcohol. The structures of the synthesized esters were confirmed by $^1H-NMR$, FT-IR spectrum and GC analysis. Basic properties of esters such as kinematic viscosity (KV), refractive index (RI), total acid number (TAN) and pour points were measured and lubricating properties such as SRV wear scar diameter (SRV WSD), fraction coefficient (COF) and 4-ball wear (4-ball WSD) were also evaluated. As the results of basic properties, KV, RI and pour point of synthetic esters increased as the carbon chain of the esters increased. Measurement value of total acid number (TAN) was indicated between 0.2~4 mgKOH/g, and that metal working fluids and pressure working oils are acceptable to use as base oil. Also, lubricating properties of the esters showed as follows: 0.391~0.689 mm of SRV WSD, 0.110~0.138 of SRV COF and 0.49~0.55 mm of 4-ball WSD depended on the structure of the esters. In a comparison on the lubrication capacity of the SRV test based on polyester TMPTO, SRV WSD result showed that a better performance caused by the alkyl group. On the other hand, SRV COF test was not influenced of the alkyl group which the capacity of the lubricant was sightly diminished than the comparison material, regardless of the alkyl group.