Sulfurized Methyl Esters of Soya Fatty Acids: Synthesis and Characterization

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

doi:10.1007/s11249-020-01292-y

Cited by 5 publications

(8 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This is because RBT and BBT contain higher percentages (∼50%) of saturated fatty acids compared to HOSuO, which was mainly composed of unsaturated fatty acids (oleic acid) and has less than 10% saturated fatty acids . Polyalphaolefins are well-known for their excellent CP and PP, so it was not surprising that PAO-6 had superior CP and PP than RBT and BBT (Figure ).…”

Section: Results and Discussionmentioning

confidence: 99%

Chemical Modification of Beef Tallow for Lubricant Application

Yosief

Sarker

Bantchev

et al. 2022

Ind. Eng. Chem. Res.

Self Cite

View full text Add to dashboard Cite

The possible application of beef tallow as a biolubricant by improving its physicochemical properties through chemical modification has been explored. The unsaturated fatty acid chain of the regular beef tallow (RBT) was alkylated with isopropyl groups in the presence of ethylaluminum sesquichloride. The alkyl-branched beef tallow (BBT) was characterized using a combination of various analytical techniques, including gas chromatography–mass spectroscopy (GC–MS), nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy, and gel permeation chromatography (GPC). GC–MS and NMR results indicate complete saturation (>95%) of the RBT double bonds with the attachment of isopropyl groups. GPC indicates the presence of oligomers in BBT. The physicochemical and tribological properties of the RBT and BBT as well as their blends with polyalphaolefin (PAO-6) or high-oleic sunflower oil (HOSuO) were evaluated. BBT has better oxidative stability than RBT, due to the elimination of the unsaturation. The introduction of alkyl groups into beef tallow led to improved low-temperature properties compared to RBT, both as neat materials and as blends in HOSuO or PAO-6. The BBT also displayed higher density (0.9030 vs 0.8969 g/mL) and kinematic viscosity (112.7 vs 44.2 mm2/s) than the RBT, possibly due to the presence of oligomers. The introduction of branching was also accompanied by higher solubility in HOSuO and POA-6, but a lower viscosity index (186 vs 149). Both RBT and BBT displayed good lubricity as HOSuO and were effective at improving PAO-6 lubricity at low concentrations (5 wt %). This study indicates that introducing branching into RBT produces new biobased materials, which can be blended into lubricants with improved properties.

show abstract

Section: Results and Discussionmentioning

confidence: 99%

Chemical Modification of Beef Tallow for Lubricant Application

Yosief

Sarker

Bantchev

et al. 2022

Ind. Eng. Chem. Res.

Self Cite

View full text Add to dashboard Cite

show abstract

“…The synthesized unsymmetrical DDODS and symmetrical DDDS were characterized using 1 H NMR, 13 C NMR (Brüker Avance III, 600MHz), and GCMS (Agilent 6890N GC system with 5973N mass selective detector under 70 eV conditions). The results of the NMR data (…”

Section: Characterizationmentioning

confidence: 99%

“…In addition, it is also less toxic and more environmentally friendly compared to phosphorus and zinc elements [10]. Sulfur-based compounds such as molybdenum disul des (MoS 2 ) [11], organic sul des [12], and sulfurized fatty acid [13] have been widely used as EP and AW additives. Unfortunately, the presence of heavy metal, Mo in MoS 2 has led to health and environmental problems [14].…”

Section: Introductionmentioning

confidence: 99%

“…Unfortunately, the presence of heavy metal, Mo in MoS 2 has led to health and environmental problems [14]. The disadvantages of sulfurized fatty acid include high pour point and low thermal oxidation stability have restricted its application under moderate temperature conditions [13]. In addition, heterocyclic sulfur-based compounds including 1,3,4-thiadiazole derivatives possess poor solubility in base oil thus limiting its application as lubricant oil additives [15,16].…”

Section: Introductionmentioning

confidence: 99%

“…1 H and13 C) and GCMS analysis are shown below: DDODS: Colorless oil; Yield: 85%; 1 H NMR (600 MHz, CDCl 3 ) δ 2.69-2.66 (4 H, m), 1.69-1.64 (4 H, m), 1.39-1.35 (4 H, m), 1.3-1.26 (24 H, m), 0.89-0.87 (6 H, t); 13 C NMR (600 MHz, CDCl 3 ) δ 39.38 (2C), 32.07, 31.96, 29.80, 29.78, 29.75, 29.67, 29.50, 29.38 (3C), 29.35, 29.32, 28.69 (2C), 22.83, 22.79, 14.24, 14.22 ppm. Calculated mass for DDODS: 346.2728 (See supplementary data, Fig.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Formation of FeS Tribofilm from Unsymmetrical Disulfides as Effective Extreme Pressure and Antiwear Additives

Ong

Lim

Lai³

et al. 2022

Preprint

View full text Add to dashboard Cite

Sulfur-based additives have excellent extreme pressure (EP) performance. However, a high amount of sulfur causes metal corrosion. The non-corrosive and ashless organo-disulfides have been synthesized via Bunte salt method. The unsymmetrical dodecyl octyl disulfide (DDODS) with good oil-solubility provides better EP and anti-wear (AW) properties. The DDODS shows outstanding EP value (1961 N) and small WSA (9 mm²) in naphthenic base oil (NBO), respectively. This performance is superior compared to symmetrical didodecyl disulfide (DDDS). The outstanding performance of DDODS is due to the good solubility in NBO and the formation of a sulfur film on the metal surface. The formation of iron sulfide (FeS) under EP conditions provides excellent tribofilm compared to iron (III) oxide (Fe2O3) and iron sulfate (FeSO4).

show abstract

Isopropyl‐branched lard and its potential application as a bio‐based lubricant

Yosief,

Sarker,

Bantchev

et al. 2023

Lubrication Science

View full text Add to dashboard Cite

Regular lard (RL) was chemically modified into isopropyl‐branched lard (BL). The isopropyl group was introduced into the triglyceride structure via a reaction of carbon–carbon double with isopropyl bromide in presence of ethylaluminum sesquichloride. The reaction was confirmed with gas chromatography–mass spectroscopy, nuclear magnetic resonance, infrared spectroscopy. The physical, tribological and chemical properties of the RL, BL and their blendings in polyalphaolefin (PAO) and high‐oleic sunflower oil (HOSuO) were investigated. The BL exhibited better solubility both in HOSuO and PAO than RL. Compared to RL, BL exhibited higher density, viscosity, improved oxidative stability and cold flow properties both as a neat material and blendings in HOSuO or PAO. However, BL displayed lower viscosity index (197 vs. 162) compared to RL. Both RL and BL displayed similar lubricity as HOSuO and showed potential such as a good lubricity additive in PAO even in small amounts (~10 wt%). This study reveals introducing alkyl branching into lard can lead to improved physico‐chemical properties and lubrication performance.

show abstract

Sulfurized Methyl Esters of Soya Fatty Acids: Synthesis and Characterization

Cited by 5 publications

References 34 publications

Chemical Modification of Beef Tallow for Lubricant Application

Chemical Modification of Beef Tallow for Lubricant Application

Formation of FeS Tribofilm from Unsymmetrical Disulfides as Effective Extreme Pressure and Antiwear Additives

Isopropyl‐branched lard and its potential application as a bio‐based lubricant

Contact Info

Product

Resources

About