1842-70-2Relevant articles and documents
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Teeter et al.
, p. 2302 (1951)
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Fatty ketones from the rearrangement of epoxidized vegetable oils
Rios, Luis A.,Llano, Biviana A.,Hoelderich, Wolfgang F.
, p. 346 - 350 (2012)
The rearrangement of epoxidized vegetable oils to produce fatty ketones, catalyzed by acidic resins, is disclosed. The non-microbial production of fatty ketones from epoxidized vegetable oils has not been previously reported. Some of the variables affecti
Diethylene Glycol/NaBr Catalyzed CO2 Insertion into Terminal Epoxides: From Batch to Continuous Flow
Rigo, Davide,Calmanti, Roberto,Perosa, Alvise,Selva, Maurizio,Fiorani, Giulia
, p. 2005 - 2016 (2021)
CO2 insertion reactions on terminal epoxides (styrene oxide, 1,2-epoxyhexane and butyl glycidyl ether) were performed in a binary homogeneous mixture comprising NaBr as the nucleophilic catalyst and diethylene glycol (DEG) as both solvent and catalyst activator (cation coordinating agent). The reaction protocol was initially studied under batch conditions either in autoclaves and glass reactors: quantitative formation of the cyclic organic carbonate products (COCs) were achieved at T=100 °C and p0(CO2)=1–40 bar. The process was then transferred to continuous-flow (CF) mode. The effects of the reaction parameters (T, p(CO2), catalyst loading, and flow rates) were studied using microfluidic reactors of capacities variable from 7.85 ? 10?2 to 0.157 cm3. Albeit the CF reaction took place at T=220 °C and 120 bar, CF improved the productivity and allowed catalyst recycle through a semi-continuous extraction procedure. For the model case of 1,2-epoxyhexane, the (non-optimized) rate of formation of the corresponding carbonate, 4-butyl-1,3-dioxolan-2-one, was increased up to 27.6 mmol h?1 equiv.?1, a value 2.5 higher than in the batch mode. Moreover, the NaBr/DEG mixture was reusable without loss of performance for at least 4 subsequent CF-tests.
Synthesis of fatty ketoesters by tandem epoxidation-rearrangement with heterogeneous catalysis
Dorado, Vicente,Fraile, José M.,Gil, Lena,Herrerías, Clara I.,Mayoral, José A.
, p. 1789 - 1795 (2020/04/09)
Unsaturated fatty esters can be easily transformed into ketoesters through a two-step process. The highly efficient epoxidation is carried out with tert-butyl hydroperoxide (TBHP) in α,α,α-trifluorotoluene (TFT) using a Ti-silica heterogeneous catalyst. The formed epoxide is easily rearranged by a heterogeneous Br?nsted acid, with Nafion-silica SAC13 as the most efficient one. Both reactions can be combined in a tandem process, with separation of the Ti-silica catalyst by filtration from the reaction medium and addition of the second acid catalyst to perform the second reaction. Each catalyst is separated individually and can be reused, with or without re-activation, under the same conditions to maximize the productivity.
