2462-84-2

Usage

Uses

Used in Biodiesel Industry:
ELAIDIC ACID METHYL ESTER is used as a component in the synthesis of biodiesel, specifically from rocket seed oil. It contributes to the overall fuel properties and performance of the biodiesel blend.
Used in Lubricant Industry:
ELAIDIC ACID METHYL ESTER is used as a lubricant in the soap industry, providing a smooth and consistent texture to the final product.
Used in Environmental and Food Contamination Studies:
ELAIDIC ACID METHYL ESTER is also recognized as an environmental and food contaminant, which makes it a subject of interest in studies related to environmental and food safety. Understanding its presence and effects in these areas is crucial for maintaining a sustainable and healthy ecosystem and food supply chain.

InChI:InChI=1/C19H36O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h10-11H,3-9,12-18H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 112-79-8 Elaidic acid 
• 112-62-9 Methyl oleate 
• 112-63-0 Methyl linoleate 
• 18287-20-2 methyl linoleate 
• 25456-04-6 erythro-9,10-dibromooctadecanoic acid 
• 25456-04-6 threo-9,10-dibromooctadecanoic acid methyl ester 
• 14959-86-5 (Z)-7-dodecenyl acetate 
• 74-88-4 methyl iodide 
• 25456-04-6 (+/-)-threo-9,10-dibromo-octadecanoic acid methyl ester 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 2597-44-6 formyl radical 
• 2500-59-6 (E)-9,10-epoxyoctadecanoic acid methyl ester 
• 29680-62-4 Tris(phenylseleno)borane 

Downstream Products

• 506-42-3 (E)-9-octadecen-1-ol 
• 112-62-9 Methyl oleate 
• 112-61-8 Methyl stearate 
• 1931-63-1 methyl ester of azelaic acid aldehyde 
• 2566-91-8 epoxidized methyl oleate 
• 7206-34-0 cis-6-octadecene 
• 7206-22-6 trans-6-octadecene 
• 13481-97-5 dimethyl (Z)-octadec-9-ene-1,18-dioate 
• 24753-49-9 Dimethyl (E)-octadec-9-enedioate 
• 120-87-6 erythro-9,10-dihydroxystearic acid 
• 2443-39-2 trans-9,10-epoxystearic acid 
• 2500-59-6 (E)-9,10-epoxyoctadecanoic acid methyl ester 
• 872-05-9 1-Decene 
• 25601-41-6 methyl 9-decenoate 

Relevant academic research and scientific papers

Rhodium-catalyzed nonisomerizing hydroformylation of methyl oleate applying lactame-based phosphoramidite ligands

The rhodium-catalyzed hydroformylation of methyl oleate (MO) with new monodentate phosphoramidite ligands 1a-d is investigated here. The ligands are characterized by lactam rings of different size (four-to seven-membered rings). In mild conditions (synthesis gas pressure: 30 bar, 80°C), the rhodium catalysts based on the P-azetidinone phosphoramidite 1a gave within 6 h complete conversion and produced mainly methyl 9-and 10-formylstearate (MFS) with 99% chemoselectivity. In the hydrolysis test, phosphoramidite 1a was also the most stable. This was additionally confirmed by density functional theory calculations.

Efficient confinement of ionic liquids in MIL-100(Fe) frameworks by the "impregnation-reaction-encapsulation" strategy for biodiesel production

A new, simple and effective strategy to confine dicationic acid ionic liquids (DAILs, 1,4-bis[3-(propyl-3-sulfonate) imidazolium] butane hydrogen sulfate) in the cages of MIL-100(Fe) frameworks was constructed. The target catalyst, defined as MIL-100(Fe)@DAILs, was characterized by XRD, FTIR, SEM, TEM, EA, TGA and N2 adsorption-desorption. Meanwhile, the catalytic activity of the MIL-100(Fe)@DAILs catalyst was evaluated by the esterification reaction with oleic acid and methanol. The results indicated that the DAILs had been effectively encapsulated within the cages of the MIL-100(Fe) frameworks. Moreover, the influence of reaction time, reaction temperature, molar ratio of methanol to oleic acid and catalyst dosage on the conversion of oleic acid was studied by univariate analysis. The conversion of oleic acid decreased from 93.5% to 86.0% when the catalyst was reused five times, which indicated that the target catalyst possessed higher catalytic activity and superior catalytic activity. Finally, an esterification mechanism catalyzed by this novel catalyst was illustrated.

Initiation of radical chain reactions of thiol compounds and alkenes without any added initiator: Thiol-catalyzed cis/trans isomerization of methyl oleate

A kinetic study of the dodecanethiol-catalyzed cis/trans isomerization of methyl oleate (cis-2) without added initiator was performed by focusing on the initiation of the radical chain reaction. The reaction orders of the rate of isomerization were 2 and 0.5 for 1 and cis-2, respectively, and an overall kinetic isotope effect kH/kD of 2.8 was found. The initiation was shown to be a complex reaction. The electron-donor/-acceptor (EDA) complex of dodecanethiol (1) and cis-2 formed in a pre-equilibrium reacts with thiol 1 to give a stearyl and a sulfuranyl radical through molecule-assisted homolysis (MAH) of the sulfur-hydrogen bond. Fragmentation of the latter gives the thiyl radical, which catalyzes the cis/trans isomerization. A computational study of the EDA complex, MAH reaction, and the sulfuranyl radical calculated that the activation energy of the isomerization was in good agreement with the experimental result of EA=82 kJ M-1. Overall, the results may explain that the thermal generation of thiyl radicals without any initiator is responsible for many well-known thermally initiated addition reactions of thiol compounds to alkenes and their respective polymerizations and for the low shelf-life stability of cis-unsaturated thiol compounds and of mixtures of alkenes and thiol compounds. Copyright

Method for synthesizing oleic acid low-alcohol ester

The invention relates to the technical field of organic synthesis and particularly discloses a method for synthesizing oleic acid low-alcohol ester. According to the method, specific Bronsted-Lewis acidic ionic liquid is taken as a catalyst, catalytic oleic acid and low alcohols are subjected to an esterification reaction, and thus corresponding oleate is obtained. The selected ionic liquid has high selectivity to the esterification reaction of the oleic acid and the low alcohols, the use amount is small, and the catalytic efficiency is high.

In Situ Generation of Ru-Based Metathesis Catalyst. A Systematic Study

A systematic study for the in situ generation of Ru-based metathesis catalysts was described. Assembly of commercially available and inexpensive reagents [Ru(p-cymene)Cl2]2, SIPr·HCl, and n-BuLi led to the formation of 18 electron arene-ruthenium complexes that, in the presence of additives such as alkynes, cyclopropenes, and diazoesters, generated highly selective and efficient catalytic systems applicable to a variety of olefin metathesis transformations. Notably, we were able to achieve a productive TON of 4500 for the self-metathesis of methyl oleate, a reaction which could be easily upscaled to 2 kg.

Supported Ru olefin metathesis catalysts: Via a thiolate tether

Thiolate-coordinated ruthenium alkylidene complexes can give high Z-selectivity and stereoretentivity in olefin metathesis. To investigate their applicability as heterogeneous catalysts, we have successfully developed a methodology to easily immobilize prototype ruthenium alkylidenes onto hybrid mesostructured silica via a thiolate tether. In contrast, the preparation of the corresponding molecular complexes appeared very challenging in solution. These prototype supported complexes contain small thiolates but still, they are slightly more Z-selective than their molecular analogues. These results open the door to more active and selective heterogeneous catalysts by supporting more advanced thiolate Ru-complexes.

Fatty acid based biocarbonates: Al-mediated stereoselective preparation of mono-, di- and tricarbonates under mild and solvent-less conditions

A catalytic method for the preparation of a series of fatty acid derived biocarbonates has been developed using a binary Al-complex/PPNCl catalyst. This catalyst system allows conversion of fatty acid derived epoxides under comparatively mild reaction conditions (70-85 °C, 10 bar) while maintaining high levels of diastereospecificity with cis/trans ratios of up to 97:3 in the products. The comparative catalysis data obtained for the reactions catalysed only by the nucleophilic halide based components show that the presence of the Al-complex is crucial for the retention of the original stereochemistry.

Bleaching Earths as Powerful Additives for Ru-Catalyzed Self-Metathesis of Non-Refined Methyl Oleate at Pilot Scale

A practical and cost-effective ruthenium-catalyzed self-metathesis of non-refined methyl oleate (85 %) derived from very high oleic sunflower oils was demonstrated at pilot scale using a robust and kg-scale commercially available SIPr-M71 pre-catalyst. The simple addition of 1 wt % bleaching earths (Tonsil 110FF) to a thermally pretreated oil could efficiently prevent catalyst deactivation. Remarkably, without the need for filtration, the catalytic system was able to achieve a turnover number (TON) of more than 744 000 at a catalyst loading of only 1 ppm. At large scale (up to 200 kg), the equilibrium of the self-metathesis reaction was reached within 1 hour at 50 °C under neat conditions at a very low 5 ppm catalyst loading to produce the expected primary metathesis products (PMP), that is, 9-octadecene and dimethyl-9-octadecenoate, with a productive TON of 94900.

A magnetically recoverable nanocatalyst based on functionalized mesoporous silica

A magnetically separable 2D-hexagonally ordered thiol functionalized mesoporous silica material (Fe@TFMS) has been synthesized through co-condensation reaction of 3-mercaptopropyltriethoxysilane (MPTES) and tetraethylorthosilicate (TEOS) using cetyltrimethylammonium bromide (CTAB) as a cationic surfactant followed by immobilization of Fe3O4 nanocrystallies at the functionalized mesopore surface. Powder X-ray diffraction (XRD), N2 adsorption/desorption analysis, FT-IR, TEM, FE-SEM, TGA/DTA, CHNS, XPS and NH3-TPD tools are employed to characterize the materials. This functionalized mesoporous material exhibited high catalytic activity in the biodiesel production from a wide range of long chain fatty acids and soybean oil. The material showed high Lewis acidity of 1.02 mmolg-1 with a good Brunauer-Emmett-Teller (BET) surface area of 411 m2 g-1. Fe@TFMS exhibited excellent catalytic efficiency for this esterification reaction using methanol as a solvent cum reactant under eco-friendly and mild reaction conditions (room temperature, 25 °C).

Epoxidized fatty acid ester plasticizer epoxidized fatty acid ester plasticizer and manufacturing method

Epoxidized fatty acid alkyl ester and methods for making epoxidized fatty acid alkyl ester. The epoxidized fatty acid alkyl ester is prepared from a fatty acid alkyl ester starting material comprising at least one of mono-unsaturated and di-unsaturated fatty acid alkyl ester molecules in a combined amount of at least 85 weight percent. Such epoxidized fatty acid alkyl esters can be employed in plasticizer compositions, either alone or in combination with other plasticizers, such as epoxidized natural oils. Such plasticizers in turn may be used in the formation of polymeric compositions.