18652-40-9

Upstream product

• 112-63-0 Methyl linoleate 
• 60-33-3 linoleic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 29907-56-0 (E)-(9R,12R,13R)-9,12,13-Trihydroxy-octadec-10-enoic acid 
• 948310-68-7 12-13-monoepoxy-9-octadecenoic acid 
• 263399-35-5 12,13-dihydroxy-9Z-octadecenoic acid 
• 403619-53-4 Benzoic acid (2E,4Z)-(R)-12-methoxycarbonyl-1-pentyl-dodeca-2,4-dienyl ester 
• 98524-17-5 methyl 13(S)-(benzoyloxy)octadeca-9(Z),11(E)-dienoate 
• 10219-70-2 (13R)-hydroxylinoleic acid methyl ester 
• 96700-36-6 benzoate of 13-hydroxy-(Z)-9-(E)-11-octadecadienonic acid methylester 
• 6410-93-1 methyl coriolate 

Relevant academic research and scientific papers

Influence of alkenyl structures on the epoxidation of unsaturated fatty acid methyl esters and vegetable oils

Epoxidation of vegetable oils or fatty acid methyl esters (FAMEs) produce important monomers which are widely used as plasticizers or stabilizers in the polymer industry. However, little attention has been focused on the influence of the alkenyl structure of the fatty acid on the efficiency and selectivity of their epoxidation. In this work, the influence of the alkenyl structure (the number of double bonds) of the FAMEs on the epoxidation reaction has been investigated. Three model FAMEs with 1 to 3 double bonds were epoxidized using both a weak (formic acid) and a strong (sulfuric acid/acetic acid) acid system. It was found that FAMEs with more double bonds have higher reactivities toward the epoxidation reaction. In addition, the electron-donating effect of the double bonds on the fatty acid chain tends to stabilize the resulting epoxide adjacent to it with the weak acid system. Furthermore, FAMEs with more double bonds easily undergo side reactions with the strong acid system (H2SO4). Epoxidation of two vegetable oils with different fatty acid compositions were carried out with the same two acid catalyst systems. And the results were in agreement with those from the FAMEs. The current findings could provide useful guidance for the epoxidation of different vegetable oils with different alkenyl structure compositions.

Autoxidation of Polyunsaturated Fatty Acids, an Expanded Mechanistic Study

The autoxidation of four isomeric methyl 9,12-octadecadienoates in benzene/1,4-cyclohexadiene has been investigated.Autoxidation of the isomers 9-Z,12-Z (methyl linoleate); 9-Z,12-E;9-E,12-Z; and 9-E,12-E (methyl linoelaidate) octadecadienoates was studied.With no cyclohexadiene or with low cyclohexadiene solvent composition, the distribution of product hydroperoxides from the various isomeric precursors was equivalent or nearly so.With higher cyclohexadiene solvent composition, the product mixtures became nonequivalent and reflected the stereochemistry of the particular diene precursor.A steady-state and iterative computer kinetic analysis is reported, and a scheme for diene fatty acid autoxidation involving reversible oxygen addition to intermediate pentadienyl carbon radicals is proposed.

Factors affect on the synthesis of silica-pillared zirconium phosphate with template-directing self-assembly method and its epoxidation catalytic performance

A series of silica-pillared zirconium phosphate materials with ordered structure were synthesized using hexadecylamine (HDA) as expanding agent, dodecyl dimethyl benzyl ammonium chloride (DDBAC) as template agent and tetraethyl orthosilicate (TEOS) as silica source. The textural properties of the materials can be effectively controlled by adjusting the dosage of HDA, DDBAC and TEOS. Furthermore, a template-directing self-assembly mechanism was proposed based on the synthesis. In the epoxidation of methyl soyate, the prepared materials showed excellent performance with 95.9 % conversion of double bonds and 84.7 % epoxy selectivity. This result is determined by the large surface area and the ordered interlayer structure. Graphical Abstract: Series silica-pillared zirconium phosphate materials with ordered structure were synthesized. The textural properties of the materials can be effectively controlled by adjusting the dosage of each reaction species. A template-directing self-assembly mechanism was proposed based on the synthesis. The materials show excellent catalytic performance on the epoxidation of methyl soyate.[Figure not available: see fulltext.]

Heterogeneous catalysis with an organic-inorganic hybrid based on MoO3chains decorated with 2,2′-biimidazole ligands

The discovery of selective heterogeneous catalytic systems for industrial oxidation processes remains a challenge. Molybdenum oxide-based polymeric hybrid materials have been shown to be oxidation catalysts under mild reaction conditions, although difficulties remain with catalyst recovery/reuse since most perform as homogeneous catalysts or possess low activity. The present study shows that the hybrid material [MoO3(2,2′-biimidazole)]·H2O (1) is a superior catalyst regarding these issues. The structure of1was confirmed (by single crystal and synchrotron X-ray powder diffraction) to comprise one-dimensional chains of corner-sharing {MoO4N2} octahedra. Strong MoO?H-N hydrogen bonds separate adjacent chains to afford parallel channels that are occupied by disordered water molecules. Hybrid1was additionally characterised by FT-IR spectroscopy,1H and13C MAS NMR, scanning electron microscopy and thermogravimetric analysis. The catalytic studies highlighted the versatility of1for oxidation reactions withtert-butylhydroperoxide as oxidant. By complementing with characterisation studies, it was verified that the reaction occurs in the heterogeneous phase, the catalyst has good stability and is recoverableviasimple procedures. The chemical reaction scope covered epoxidation and sulfoxidation, and the substrate scope included biomass-deriveddl-limonene and fatty acid methyl esters to give renewable bio-products, as well as thiophene and thioanisole substrates.

A silicododecamolybdate/pyridinium-tetrazole hybrid molecular salt as a catalyst for the epoxidation of bio-derived olefins

The hybrid polyoxometalate (POM) salt (Hptz)4[SiMo12O40]?nH2O (1) (ptz = 5-(2-pyridyl)tetrazole) has been prepared, characterized by X-ray crystallography, and examined as a catalyst for the epoxidation of cis-cyclooctene (Cy) and bio-derived olefins, namely dl-limonene (Lim; a naturally occurring monoterpene found in the rinds of citrus fruits), methyl oleate and methyl linoleate (fatty acid methyl esters (FAMEs) obtained by transesterification of vegetable oils). The crystal structure of 1 consists of α-Keggin-type heteropolyanions, [SiMo12O40]4-, surrounded by space-filling and charge-balancing 2-(tetrazol-5-yl)pyridinium (Hptz+) cations, as well as by a large number of water molecules of crystallization (n = 9). The water molecules mediate an extensive three-dimensional (3D) hydrogen-bonding network involving the inorganic anions and organic cations. For the epoxidation of the model substrate Cy in a nonaqueous system (tert-butylhydroperoxide as oxidant), the catalytic performance of 1 (100% epoxide yield at 24 h, 70 °C) was superior to that of the tetrabutylammonium salt (Bu4N)4[SiMo12O40] (2) (63% epoxide yield at 24 h), illustrating the role of the counterion Hptz+ in enhancing catalytic activity. The hybrid salt 1 was effective for the epoxidation of Lim (69%/85% conversion at 6 h/24 h) and the FAMEs (87–88%/100% conversion at 6 h/24 h), leading to useful bio-based products (epoxides, diepoxides and diol products).

Selective Epoxidation of Fatty Acids and Fatty Acid Methyl Esters by Fungal Peroxygenases

Recently discovered fungal unspecific peroxygenases from Marasmius rotula and Chaetomium globosum catalyze the epoxidation of unsaturated fatty acids (FA) and FA methyl esters (FAME), unlike the well-known peroxygenases from Agrocybe aegerita and Coprinopsis cinerea. Reactions of a series of unsaturated FA and FAME with cis-configuration revealed high (up to 100 %) substrate conversion and selectivity towards epoxidation, although some significant differences were observed between enzymes and substrates with the best results being obtained with the C. globosum enzyme. This and the M. rotula peroxygenase appear as promising biocatalysts for the environmentally-friendly production of reactive FA epoxides given their self-sufficient monooxygenase activity and the high conversion rate and epoxidation selectivity.

Enzymatic synthesis and chemical inversion provide both enantiomers of bioactive epoxydocosapentaenoic acids

Epoxy PUFAs are endogenous cytochrome P450 (P450) metabolites of dietary PUFAs. Although these metabolites exert numerous biological effects, attempts to study their complex biology have been hampered by difficulty in obtaining the epoxides as pure regioi

Ionic ammonium and anilinium based polymolybdate hybrid catalysts for olefin epoxidation

Ionic polymolybdate hybrids (IPH) are interesting catalysts for liquid phase olefin epoxidation with tert-butylhydroperoxide; (tbhp), e.g. conversion of terpenic and fatty acid methyl ester (FAME) components of biomass to useful bio-products. IPHs may be easily prepared, under clean, mild, aqueous phase conditions. The type of organic precursor and the synthesis conditions influence the structural features of the IPHs. In this work, IPH epoxidation catalysts possessing one- (1-D) or two-dimensional (2-D) structures were investigated, which included the new materials 1-D methylammonium ammonium trimolybdate [Mo3O10?CH3NH3·NH4] (1) and 2-D bis(2,5-dimethylanilinium) pentamolybdate [Mo5O16?2(NH3C6H3(CH3)2)] (4) with solved structures, and 1-D bis(3,5-dimethylanilinium) trimolybdate [Mo3O10·2(NH3C6H3(CH3)2)] (2), bis(4-methylanilinium) trimolybdate [Mo3O10·2(NH3C6H4CH3)] (3), 2-D bis(anilinium) pentamolybdate [Mo5O16?2(NH3C6H5)] (5), bis(4-methylanilinium) pentamolybdate [Mo5O16?2(NH3C6H4CH3)] (6) and bis(4-ethylanilinium) pentamolybdate [Mo5O16?2(NH3C6H4C2H5)] (7). Systematic characterisation and catalytic studies helped gain insights into structure-activity relationships. The best-performing catalyst (2) was effective for the epoxidation of the FAMEs such as, methyl oleate which gave 92% methyl 9,10-epoxyoctadecanoate yield, at 99% conversion, at 70 °C. The reaction conditions (temperature, type of cosolvent and oxidant) influenced the catalytic reaction. Catalytic performance in consecutive batch runs was steady, and the structural features were essentially preserved.

Chemistry and Catalytic Performance of Pyridyl-Benzimidazole Oxidomolybdenum(VI) Compounds in (Bio)Olefin Epoxidation

The chemistry and catalytic performance of the dichlorido complex [MoO2Cl2(pbim)] (1) [pbim = 2-(2-pyridyl)-benzimidazole] in the epoxidation of olefins is reported. Complex 1 acts as a precatalyst and is more effective with tert-butylhydroperoxide (TBHP) as the oxidant than with aq. hydrogen peroxide: the cis-cyclooctene (Cy) reaction with TBHP gave 98 % epoxide yield at 70 °C/24 h. Catalyst characterization showed that 1 is transformed in situ to the oxidodiperoxido complex [MoO(O2)2(pbim)] (2), with H2O2 and a hybrid molybdenum(VI) oxide solid formulated as [MoO3(pbim)] (3) with TBHP. The hybrid material 3 was prepared on a larger scale and explored for the epoxidation of the biorenewable olefins methyl oleate, methyl linoleate, and (R)-(+)-limonene. With TBHP as the oxidant, 3 acts as a source of soluble active species of the type 2. A practical method for recycling oxidodiperoxidomolybdenum(VI) catalysts for the Cy/TBHP reaction is demonstrated by using an ionic liquid as the solvent for the molecular catalyst 2.

Triazolyl, Imidazolyl, and Carboxylic Acid Moieties in the Design of Molybdenum Trioxide Hybrids: Photophysical and Catalytic Behavior

Three organic ligands bearing 1,2,4-triazolyl donor moieties, (S)-4-(1-phenylpropyl)-1,2,4-triazole (trethbz), 4-(1,2,4-triazol-4-yl)benzoic acid (trPhCO2H), and 3-(1H-imidazol-4-yl)-2-(1,2,4-triazol-4-yl)propionic acid (trhis), were prepared to evaluate their coordination behavior in the development of molybdenum(VI) oxide organic hybrids. Four compounds, [Mo2O6(trethbz)2]·H2O (1), [Mo4O12(trPhCO2H)2]·0.5H2O (2a), [Mo4O12(trPhCO2H)2]·H2O (2b), and [Mo8O25(trhis)2(trhisH)2]·2H2O (3), were synthesized and characterized. The monofunctional tr-ligand resulted in the formation of a zigzag chain [Mo2O6(trethbz)2] built up from cis-{MoO4N2} octahedra united through common μ2-O vertices. Employing the heterodonor ligand with tr/-CO2H functions afforded either layer or ribbon structures of corner- or edge-sharing {MoO5N} polyhedra (2a or 2b) stapled by tr-links in axial positions, whereas -CO2H groups remained uncoordinated. The presence of the im-heterocycle as an extra function in trhis facilitated formation of zwitterionic molecules with a protonated imidazolium group (imH+) and a negatively charged -CO2- group, whereas the tr-fragment was left neutral. Under the acidic hydrothermal conditions used, the organic ligand binds to molybdenum atoms either through [N-N]-tr or through both [N-N]-tr and μ2-CO2- units, which occur in protonated bidentate or zwitterionic tetradentate forms (trhisH+ and trhis, respectively). This leads to a new zigzag subtopological motif (3) of negatively charged polyoxomolybdate {Mo8O25}n2n- consisting of corner- and edge-sharing cis-{MoO4N2} and {MoO6} octahedra, while the tetradentate zwitterrionic trhis species connect these chains into a 2D net. Electronic spectra of the compounds showed optical gaps consistent with semiconducting behavior. The compounds were investigated as epoxidation catalysts via the model reactions of achiral and prochiral olefins (cis-cyclooctene and trans-β-methylstyrene) with tert-butylhydroperoxide. The best-performing catalyst (1) was explored for the epoxidation of other olefins, including biomass-derived methyl oleate, methyl linoleate, and prochiral dl-limonene.