2566-91-8Relevant articles and documents
Proton Nuclear Magnetic Resonance-Based Method for the Quantification of Epoxidized Methyl Oleate
Kaur, Avneet,Bhardwaj, Neha,Kaur, Amanpreet,Abida, Km,Nagaraja, Tejo Prakash,Ali, Amjad,Prakash, Ranjana
, p. 139 - 147 (2021)
Epoxidized methyl esters (EMO) with their high oxirane ring reactivity, acts as a raw material in the synthesis of various industrial chemicals including polymers, stabilizers, plasticizers, glycols, polyols, carbonyl compounds, biolubricants etc. EMO has been generally quantified by the gas chromatography (GC) and high-performance liquid chromatography (HPLC) techniques. Taking into the account of the limitations of these techniques, two qHNMR-based equations have been proposed for the quantification of EMO in the mixture of EMO and methylesters (MO). The validity of the proposed method was determined using standard mixtures of MO and EMO having different molar concentrations. The developed equations have been applied on the samples of EMO prepared from oleic acid in two-step process viz., esterification followed by epoxidation. The qHNMR-based EMO quantification showed acceptable agreement with the results obtained from HPLC analysis.
Oxidations by the system 'hydrogen peroxide-[Mn2L 2O3]2 + (L = 1,4,7-trimethyl-1,4,7- triazacyclononane)-carboxylic acid': Part 13. Epoxidation of methyl oleate in acetonitrile solution [1]
Mandelli, Dalmo,Kozlov, Yuriy N.,Carvalho, Wagner A.,Shul'Pin, Georgiy B.
, p. 93 - 97 (2012)
Methyl oleate can be efficiently (yield and selectivity attain 100%, turnover number is up to 2000) epoxidized with hydrogen peroxide in acetonitrile solution at 25°C using the combination "[Mn2L 2O3](PF6)2 (L = 1,4,7-trimethyl-1,4, 7-triazacyclononane)/oxalic acid" as a catalyst. Kinetic features of the reaction were studied and the conclusion has been made that high-valent oxo-manganese rather than hydroxyl radicals is a crucial oxidizing species in this process.
One-pot conversion of Epoxidized Soybean Oil (ESO) into soy-based polyurethanes by MoCl2O2 catalysis
Pantone, Vincenzo,Annese, Cosimo,Fusco, Caterina,Fini, Paola,Nacci, Angelo,Russo, Antonella,D'Accolti, Lucia
, (2017)
An innovative and eco-friendly one-pot synthesis of bio-based polyurethanes is proposed via the epoxy-ring opening of epoxidized soybean oil (ESO) with methanol, followed by the reaction of methoxy bio-polyols intermediates with 2,6-tolyl-diisocyanate (TDI). Both synthetic steps, methanolysis and polyurethane linkage formation, are promoted by a unique catalyst, molybdenum(VI) dichloride dioxide (MoCl2O2), which makes this procedure an efficient, cost-effective, and environmentally safer method amenable to industrial scale-up.
Tungsten Peroxopolyoxo Complexes as Advanced Catalysts for the Oxidation of Organic Compounds with Hydrogen Peroxide
Baltakhinov, Vladimir P.,Berdnikova, Polina V.,Bukhtiyarov, Valerii I.,Chesalov, Yuriy A.,Khlebnikova, Tatiana B.,Kochubey, Dmitry I.,Pai, Zinaida P.,Uchenova, Yulia V.,Uslamin, Evgeny A.,Yushchenko, Dmitry Yu.
, (2020)
Selective oxidation of organic substrates by environment-friendly oxidizing agents is an important ingredient of the sustainable chemical industry. Here we report a comprehensive study in the field of metal peoroxocomplex catalysis for the selective liqui
INTRAMOLECULAR EPOXIDATION WITH THE H2O2/ORTHO ESTER SYSTEM
Rebek, J.,McCready, Jr. and R.
, p. 2491 - 2492 (1980)
Intramolecular epoxidation is shown to occur when trimethyl ortho oleate is treated with H2O2.
-
Frankel et al.
, p. 901,902,903 (1977)
-
Engineering Multifunctionality in Hybrid Polyoxometalates: Aromatic Sulfonium Octamolybdates as Excellent Photochromic Materials and Self-Separating Catalysts for Epoxidation
Kumar, Ashwani,Gupta, Abhishek Kumar,Devi, Manisha,Gonsalves, Kenneth E.,Pradeep, Chullikkattil P.
, p. 10325 - 10336 (2017)
Engineering multifunctionality in hybrid polyoxometalates (hybrid POMs) is an interesting but scarcely explored topic. Herein, we set about engineering two important materials properties, viz., photochromism and self-separating catalysis, in a hybrid POM by modulating the counterion motif. A series of six aromatic sulfonium counterions have been developed on the basis of an aromatic sulfonium counterion motif that allows structural and electronic fine-tuning by changing substituents at multiple locations. Using the aromatic sulfonium counterions and sodium molybdate, six new aromatic sulfonium octamolybdate hybrids (1-6) having formulas (HPDS)4[Mo8O26] (1), (HMPDS)4[Mo8O26] (2), (MPDS)4[Mo8O26] (3), (APDS)4[Mo8O26] (4), (AMPDS)4[Mo8O26] (5), and (MAPDS)4[Mo8O26] (6) (where HPDS = (4-hydroxyphenyl)dimethylsulfonium, HMPDS = (4-hydroxy-2-methylphenyl)dimethylsulfonium, MPDS = (4-methoxyphenyl)dimethylsulfonium, APDS = (4-(allyloxy)phenyl)dimethylsulfonium, AMPDS = (4-(allyloxy)-2-methylphenyl)dimethylsulfonium and MAPDS = (4(methacryloyloxy)phenyl)dimethylsulfonium) have been synthesized, and their structures were confirmed by single crystal X-ray diffraction and ESI-MS analyses. Hybrids 1-6 acted as good solid-state photochromic materials exhibiting color change from white to purple under UV illumination (350 nm), and we show here that the photochromic properties of hybrids 1-6 could be modulated by changing the substitutions on the counterion motif. A coloration kinetic half-life (t1/2) of 0.33 min was achieved with this class of hybrid POMs. Hybrids 1-6 exhibited excellent self-separating catalytic properties toward the epoxidation of olefins, yielding up to 99% epoxide product with good selectivity in short time. The substituents on the aromatic sulfonium counterions helps to fine-tune the electronic, lipophilic, and solubility properties of the hybrids and thereby their catalytic properties. Moreover, we used ESI-MS analyses to understand the mechanism of catalysis exhibited by octamolybdates 1-6 in the presence of H2O2, and we succeeded in identifying a hitherto undetected intermediate, tetraperoxo-octamolybdates, shedding more light on the epoxidation mechanism.
Copper mediated epoxidation of high oleic natural oils with a cumene-O2 system
Scotti, Nicola,Ravasio, Nicoletta,Psaro, Rinaldo,Evangelisti, Claudio,Dworakowska, Sylwia,Bogdal, Dariusz,Zaccheria, Federica
, p. 80 - 85 (2015)
The epoxidation of methyl oleate or high oleic FAMEs from different vegetable oils was carried out in a one-pot reaction over supported copper catalysts by using cumene as oxygen carrier. Cumene firstly reacts with O2 generating cumene hydroperoxide, that by reaction with methyl oleate forms the epoxide. By using 8% Cu catalysts supported on alumina or on a polymer yields up to 87% could be obtained in a single pot at 100 °C.
Spongy titanosilicate promotes the catalytic performance and reusability of WO3 in oxidative cleavage of methyl oleate
Huang, Zuoxin,Lin, Min,Peng, Xinxin,Shu, Xingtian,Xia, Changjiu,Xin, Shihao,Zhang, Yao,Zheng, Aiguo,Zhu, Bin
, p. 5135 - 5144 (2022/02/25)
A tungsten containing catalyst catalyzed oxidative cleavage of methyl oleate (MO) by employing H2O2 as an oxidant and is known as an efficient approach for preparing high value-added chemicals, however, the tungsten leaching problem remains unresolved. In this work, a binary catalyst consisting of tungsten oxide (WO3) and spongy titanosilicate (STS) zeolite is proposed for MO oxidative cleavage. The function of STS in this catalyst is investigated. On the one hand, STS converts MO to 9,10-epoxystearate (MES), which further forms nonyl aldehyde (NA) and methyl azelaaldehydate (MAA) with the catalysis of WO3. In this way, MO oxidation and hydrolysis that generates unwanted diol product 9,10-dihydroxystearate (MDS) decreases obviously. On the other hand, STS decomposes peroxide and promotes the conversion of soluble peroxotungstate to insoluble polytungstate. Meanwhile, these tungsten species are allowed to precipitate on its surface instead of remaining in the liquid phase owing to its relative large specific area. Therefore, tungsten leaching can be reduced from 37.0% to 1.2%. Due to the cooperation of WO3 and STS, 94.4% MO conversion and oxidative cleavage product selectivity of 63.1% are achieved, and the WO3-STS binary catalyst maintains excellent catalytic performance for 8 recycling reactions.
Synthesis of Imidazoles from Fatty 1,2-Diketones
Bouchakour, Mansouria,Daaou, Mortada,Duguet, Nicolas
, p. 1647 - 1652 (2021/03/16)
Unsaturated vegetable oils and their corresponding fatty acid derivatives constitute interesting renewable platforms for the preparation of heterocycles, notably through the formation of oxygenated intermediates. In this work, fatty imidazoles were prepared from the corresponding 1,2-diketones through Debus-Radziszewski reaction. The reaction was optimized under microwave irradiation using a 1,2-diketone derived from methyl oleate and ammonium acetate as a nitrogen source. Using benzaldehyde as a model substrate, the reaction occurs at 180 °C for 5 min and the desired imidazole was formed in 96 % GC yield. A range of aldehydes was tested under the optimized conditions and the corresponding imidazoles were obtained in 33–99 % isolated yields (20 examples).
