scholarly journals Improvement of Physicochemical Characteristics of Monoepoxide Linoleic Acid Ring Opening for Biolubricant Base Oil

2011 ◽  
Vol 2011 ◽  
pp. 1-8 ◽  
Author(s):  
Jumat Salimon ◽  
Nadia Salih ◽  
Bashar Mudhaffar Abdullah
Keyword(s):  
Linoleic Acid ◽  
Ring Opening ◽  
Viscosity Index ◽  
Physicochemical Characteristics ◽  
High Yield ◽  
Optimum Conditions ◽  
Base Oil ◽  
New Class ◽  
Ring Opening Reaction ◽  
Toluene Sulfonic Acid

For environmental reasons, a new class of environmentally acceptable and renewable biolubricant based on vegetable oils is available. In this study, oxirane ring opening reaction of monoepoxide linoleic acid (MEOA) was done by nucleophilic addition of oleic acid (OA) with usingp-toluene sulfonic acid (PTSA) as a catalyst for synthesis of 9(12)-hydroxy-10(13)-oleoxy-12(9)-octadecanoic acid (HYOOA) and the physicochemical properties of the resulted HYOOA are reported to be used as biolubricant base oils. Optimum conditions of the experiment using D-optimal design to obtain high yield% of HYOOA and lowest OOC% were predicted at OA/MEOA ratio of 0.30 : 1 (w/w), PTSA/MEOA ratio of 0.50 : 1 (w/w), reaction temperature at 110, and reaction time at 4.5 h. The results showed that an increase in the chain length of the midchain ester resulted in the decrease of pour point (PP) , increase of viscosity index (VI) up to 153, and improvement in oxidative stability (OT) to 180.94.

scholarly journals Diesters Biolubricant Base Oil: Synthesis, Optimization, Characterization, and Physicochemical Characteristics

2012 ◽  
Vol 2012 ◽  
pp. 1-10 ◽  
Author(s):  
Jumat Salimon ◽  
Nadia Salih ◽  
Bashar Mudhaffar Abdullah
Keyword(s):  
Oleyl Alcohol ◽  
Viscosity Index ◽  
Physicochemical Characteristics ◽  
High Yield ◽  
Esterification Reaction ◽  
Optimum Conditions ◽  
Octadecanoic Acid ◽  
Base Oil ◽  
H Nmr ◽  
Oil Synthesis

Diesters biolubricant base oil, oleyl 9(12)-hydroxy-10(13)-oleioxy-12(9)-octadecanoate (OLHYOOD) was synthesized based on the esterification reaction of 9,12-hydroxy-10,13-oleioxy-12-octadecanoic acid (HYOOA) with oleyl alcohol (OL) and catalyzed by sulfuric acid (SA). Optimum conditions of the experiment to obtain high yield % of OLHYOOD were predicted at ratio of OL/HYOOA of 2 : 1 mol/mol, ratio of SA/HYOOA of 0.7 : 1 mol/mol, reaction temperature 110°C, and 7 h of reaction time. At this condition, the yield of OLHYOOD was 88.7%. Disappearance of carboxylic acid (C=O) peak has been observed by FTIR with appearance of ester (C=O) peak at 1738 cm-1.13C, and1H NMR spectra analyses confirmed the result of OLHYOOD with the appearance of carbon-ester (C=O) chemical shift at 173.93 ppm and at 4.05 ppm for13C and1H NMR, respectively. The physicochemical characteristics of the OLHYOOD were also determined, which showed improved low temperature properties (PP) −62°C, viscosity index (VI) at 192 and also increased oxidative stability (OT) up to 215.24°C.

scholarly journals Effect of The Ratio of H-Zeolite Catalyst and Temperature in The Opening Ring Reaction in Bio Lube Base Oil Production from Palm Oil

METANA ◽  
2020 ◽  
Vol 16 (1) ◽  
pp. 1-10
Author(s):  
Abdillah Iman Izzan ◽  
Ary Octaviani ◽  
Purwanto Purwanto
Keyword(s):  
Palm Oil ◽  
Ring Opening ◽  
Zeolite Catalyst ◽  
Viscosity Index ◽  
Weight Ratio ◽  
Acid Number ◽  
Lubricating Oil ◽  
Future Research ◽  
Base Oil ◽  
Ring Opening Reaction

Lubricants are materials that can reduce friction between two components. Lubricants are very important to keep the engine from being damaged quickly. Currently lubricants on the market generally comes from petroleum derivatives with limited availability. Therefore, technology needs to be developed to look for other raw materials as a substitute for petroleum based lubricating oil, namely by utilizing the potential of existing vegetable oils, one of which is palm oil. Biolubricant made from palm oil will be made using the method of transesterification, epoxidation and ring opening reaction. To increase yield and high product quality, a catalyst in the form of H-Zeolite is used. So that this study aims to determine the effect of the ratio of H-Zeolite catalyst to ring opening reactions. The quality of lube base oil could be indicated from density, viscosity index and acid number. Acid number will smaller in presence higher content in 10% weight ratio of H-Zeolite as catalyst and EPOME also higher temperature of ring-opening reaction because the catalyst H-Zeolit will work more effective in temperature 75oC. Other evidence is of density and viscosity index would show good value than smaller amount of H-Zeolit and lower temperature of reaction. Advices for the future research are the purification needs to be done not only physically but also chemically to maximize the results obtained. Preferably on the reaction of opening the epoxides rings used a long chain alcohol compounds that have a high viscosity and boiling point to obtain a better viscosities value

scholarly journals Optimization of the oxirane ring opening reaction in biolubricant base oil production

2016 ◽  
Vol 9 ◽  
pp. S1053-S1058 ◽  
Author(s):  
Jumat Salimon ◽  
Bashar Mudhaffar Abdullah ◽  
Nadia Salih
Keyword(s):  
Ring Opening ◽  
Oil Production ◽  
Oxirane Ring ◽  
Base Oil ◽  
Ring Opening Reaction

scholarly journals Attempted Synthesis and Unexpected β-Fragmentation of a Hindered β-Keto Nitroxide

2017 ◽  
Vol 70 (10) ◽  
pp. 1106 ◽  
Author(s):  
Chris Edwards ◽  
Peter C. Healy ◽  
W. Ken Busfield ◽  
Ezio Rizzardo ◽  
San H. Thang ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Ring Opening ◽  
Sodium Tungstate ◽  
Crystallographic Analysis ◽  
High Yield ◽  
Fragmentation Mechanism ◽  
Pentanoic Acid ◽  
X Ray ◽  
Ring Opening Reaction

The attempted synthesis of a β-keto imidazolidinone nitroxide by oxidation of the β-hydroxy imidazolidinone precursor with hydrogen peroxide and sodium tungstate led to an unexpected ring-opening reaction to produce 1,4-diazaspiro[4.5]dec-1-en-3-oxo-2-pentanoic acid 1-oxide (13) in high yield. The structure of 13 was confirmed by X-ray crystallographic analysis. A β-fragmentation mechanism is suggested for the oxidative ring-opening reaction.

scholarly journals Selenium-Epoxy ‘Click’ Reaction and Se-Alkylation—Efficient Access to Organo-Selenium and Selenonium Compounds

Chemistry ◽  
2020 ◽  
Vol 2 (4) ◽  
pp. 827-836
Author(s):  
Taejun Eom ◽  
Anzar Khan
Keyword(s):  
Red Blood Cells ◽  
Blood Cells ◽  
Ring Opening ◽  
Click Reaction ◽  
Oxirane Ring ◽  
New Class ◽  
Ring Opening Reaction ◽  
Efficient Access ◽  
High Concentrations ◽  
Cationic Materials

This work establishes the ‘click’ nature of the base-catalyzed oxirane ring opening reaction by the selenolate nucleophile. The ‘click’-generated ß-hydroxy selenide can be alkylated to afford cationic selenium species. Hemolytic studies suggest that selenonium cations do not lyse red blood cells even at high concentrations. Overall, these results indicate the future applicability of the developed organo-selenium chemistry in the preparation of a new class of cationic materials based on the seleno-ether motif.

ChemInform Abstract: Unravelling a New Class of Chiral Organocatalyst for Asymmetric Ring-Opening Reaction of meso Epoxides with Anilines.

ChemInform ◽  
2014 ◽  
Vol 45 (46) ◽  
pp. no-no
Author(s):  
Manish Kumar ◽  
Rukhsana I. Kureshy ◽  
S. Saravanan ◽  
Shailesh Verma ◽  
Ajay Jakhar ◽  
...  
Keyword(s):  
Ring Opening ◽  
New Class ◽  
Ring Opening Reaction ◽  
Asymmetric Ring Opening ◽  
Asymmetric Ring Opening Reaction

scholarly journals Towards Thermally Reversible Networks Based on Furan-Functionalization of Jatropha Oil

Molecules ◽  
2020 ◽  
Vol 25 (16) ◽  
pp. 3641
Author(s):  
Frita Yuliati ◽  
Peter J. Deuss ◽  
Hero J. Heeres ◽  
Francesco Picchioni
Keyword(s):  
Ring Opening ◽  
Alder Reaction ◽  
Diels Alder ◽  
Epoxide Ring ◽  
Cross Linking ◽  
Jatropha Oil ◽  
Optimum Conditions ◽  
Epoxide Ring Opening ◽  
Diels Alder Reaction ◽  
Ring Opening Reaction

A novel biobased monomer for the preparation of thermally reversible networks based on the Diels-Alder reaction was synthesized from jatropha oil. The oil was epoxidized and subsequently reacted with furfurylamine to attach furan groups via an epoxide ring opening reaction. However, furfurylamine also reacted with the ester groups of the triglycerides via aminolysis, thus resulting in short-chain molecules that ultimately yielded brittle thermally reversible polymers upon cross-linking via a Diels-Alder reaction. A full-factorial experimental design was used in finding the optimum conditions to minimize ester aminolysis and to maximize the epoxide ring opening reaction as well as the number of furans attached to the modified oil. The optimum conditions were determined experimentally and were found to be 80 °C, 24 h, 1:1 molar ratio, with 50 mol % of LiBr with respect to the modified oil, resulting in 35% of ester conversion, 99% of epoxide conversion, and an average of 1.32 furans/triglyceride. Ultimately, further optimization by a statistical approach led to an average of 2.19 furans per triglyceride, which eventually yielded a flexible network upon cross-linking via a Diels-Alder reaction instead of the brittle one obtained when the furan-functionalization reaction was not optimized.

Unravelling a New Class of Chiral Organocatalyst for Asymmetric Ring-Opening Reaction of Meso Epoxides with Anilines

2014 ◽  
Vol 16 (11) ◽  
pp. 2798-2801 ◽  
Author(s):  
Manish Kumar ◽  
Rukhsana I. Kureshy ◽  
S. Saravanan ◽  
Shailesh Verma ◽  
Ajay Jakhar ◽  
...  
Keyword(s):  
Ring Opening ◽  
New Class ◽  
Ring Opening Reaction ◽  
Asymmetric Ring Opening ◽  
Asymmetric Ring Opening Reaction

scholarly journals Production of Chemoenzymatic Catalyzed Monoepoxide Biolubricant: Optimization and Physicochemical Characteristics

2012 ◽  
Vol 2012 ◽  
pp. 1-11 ◽  
Author(s):  
Jumat Salimon ◽  
Nadia Salih ◽  
Bashar Mudhaffar Abdullah
Keyword(s):  
Linoleic Acid ◽  
Carboxylic Acid ◽  
Immobilized Lipase ◽  
Viscosity Index ◽  
Oxidative Degradation ◽  
Oxirane Oxygen ◽  
Physicochemical Characteristics ◽  
Novozym 435 ◽  
Consecutive Reactions ◽  
Acid Catalyzed

Linoleic acid (LA) is converted to per-carboxylic acid catalyzed by an immobilized lipase fromCandida antarctica(Novozym 435). This per-carboxylic acid is only intermediate and epoxidized itself in good yields and almost without consecutive reactions. Monoepoxide linoleic acid 9(12)-10(13)-monoepoxy 12(9)-octadecanoic acid (MEOA) was optimized using D-optimal design. At optimum conditions, higher yield% (82.14) and medium oxirane oxygen content (OOC) (4.91%) of MEOA were predicted at 15 μL of H2O2, 120 mg of Novozym 435, and 7 h of reaction time. In order to develop better-quality biolubricants, pour point (PP), flash point (FP), viscosity index (VI), and oxidative stability (OT) were determined for LA and MEOA. The results showed that MEOA exhibited good low-temperature behavior with PP of−41°C. FP of MEOA increased to128°Ccomparing with115°Cof LA. In a similar fashion, VI for LA was 224 generally several hundred centistokes (cSt) more viscous than MEOA 130.8. The ability of a substance to resist oxidative degradation is another important property for biolubricants. Therefore, LA and MEOA were screened to measure their OT which was observed at 189 and168°C, respectively.

Rheometric Studies of New Class Ionic Liquid Nanolubricants

2017 ◽  
Author(s):  
Sayavur I. Bakhtiyarov ◽  
Dennis A. Siginer
Keyword(s):  
Ionic Liquid ◽  
Vapor Pressure ◽  
Viscosity Index ◽  
High Viscosity ◽  
Parallel Plates ◽  
Space Applications ◽  
Base Oil ◽  
Mineral Oils ◽  
New Class ◽  
Materials Used

The traditional lubricating materials used in space, such as mineral oils, polyol ester, PFPE, Pennzane, etc. have limited lifetimes in vacuum due to the catalytic degradation on metal surfaces, high vaporization at high temperatures, dewetting, and other disadvantages. The lubricants for the space applications must have vacuum stability (i.e. low vapor pressure), high viscosity index (wide liquid range), low creep tendency, good elastohydrodynamic and boundary lubrication properties, radiation atomic oxygen resistance, optical or infrared transparency. Thermophysical and chemical analyses are another important required set of tests for the newly developed space lubricants. Some of these properties for liquid lubricants are base oil and additive volatility, creep, surface tension, viscosity, chemical composition, weight loss, density, vapor pressure, etc. Unfortunately, the properties such as non-linearity in the rheological behavior of the lubricants were not studied well for newly developed systems. The rheological properties are crucial to analyzing thermodynamic and energy dissipative aspects of the lubrication process. The rheological measurements for the newly developed ionic liquid nanolubricant were conducted using rotational rheometer AES G-2 of “parallel-plates” mode.

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