2462-84-2Relevant articles and documents
Gibson,Strassburger
, p. 791 (1976)
Rhodium-catalyzed nonisomerizing hydroformylation of methyl oleate applying lactame-based phosphoramidite ligands
Benetskiy, Eduard,Luehr, Susan,Vilches-Herrera, Marcelo,Selent, Detlef,Jiao, Haijun,Domke, Lutz,Dyballa, Katrin,Franke, Robert,Boerner, Armin
, p. 2130 - 2136 (2014)
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
Han, Mingjuan,Gu, Zheng,Chen, Chong,Wu, Zuowang,Que, Yigen,Wang, Qiang,Wan, Hui,Guan, Guofeng
, p. 37110 - 37117 (2016)
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.
In Situ Generation of Ru-Based Metathesis Catalyst. A Systematic Study
Müller, Daniel S.,Raoul, Yann,Le N?tre, Jér?me,Baslé, Olivier,Mauduit, Marc
, p. 3511 - 3518 (2019/04/01)
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.
Method for synthesizing oleic acid low-alcohol ester
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Page/Page column 4-6, (2019/11/12)
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.
Bleaching Earths as Powerful Additives for Ru-Catalyzed Self-Metathesis of Non-Refined Methyl Oleate at Pilot Scale
Allard, Jessica,Curbet, Idriss,Chollet, Guillaume,Tripoteau, Fabien,Sambou, Sophie,Caijo, Frédéric,Raoul, Yann,Crévisy, Christophe,Baslé, Olivier,Mauduit, Marc
supporting information, p. 12729 - 12734 (2017/09/25)
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.
