79-91-4Relevant articles and documents
Farmer,Ingold
, p. 1372 (1920)
Sunlight-induced C–C bond formation reaction: Radical addition of alcohols/ethers/acetals to olefins
Hayakawa, Mamiko,Shirota, Hisashi,Hirayama, Souta,Yamada, Ryuusei,Aoyama, Tadashi,Ouchi, Akihiko
, (2021/04/09)
A sunlight-induced C–C bond formation reactions upon the addition of alcohols/ethers/acetals to olefins proceeded efficiently using di-tert-butyl peroxide (DTBP). The reactions proceeded faster than many of the previously reported sunlight and many conventional lamp photolyses, typically in 3–4 h under irradiation with sunlight, in excellent yield using olefins bearing two electron withdrawing groups (EWGs) (product yield > 95 %) and in good to fair yield with olefins bearing one EWG. The yields observed for some products were ～20 % higher than those obtained using a conventional Xe lamp as the light source, which was confirmed to be due to a light intensity effect. Gram-scale experiments showed similar yields to those observed in their corresponding small-scale experiments.
Continuous-Flow Preparation of γ-Butyrolactone Scaffolds from Renewable Fumaric and Itaconic Acids under Photosensitized Conditions
Gérardy, Romaric,Winter, Marc,Horn, Clemens R.,Vizza, Alessandra,Van Hecke, Kristof,Monbaliu, Jean-Christophe M.
supporting information, p. 2012 - 2017 (2017/12/26)
The method and results described herein concern the photosensitized addition of various alcohols to renewable platform fumaric and itaconic acids under scalable continuous-flow conditions in glass micro- and mesofluidic reactors. Alcohols were used both as reagents and as solvents, thus contributing to a reduced environmental footprint. Process parameters such as the temperature, light intensity, and the nature as well as amount of the photosensitizer were assessed under microfluidic conditions and, next, transposed to a lab-scale mesofluidic reactor connected with an in-line NMR spectrometer for real-time reaction monitoring. Substituted γ-butyrolactones, including spiro derivatives with unique structural features, were obtained with quantitative conversion of the starting materials and in 47-76% isolated yields. The model photoaddition of isopropanol to fumaric acid was next successfully transposed in a pilot-scale continuous-flow photoreactor to further demonstrate scalability.
Microflow photochemistry - A reactor comparison study using the photochemical synthesis of terebic acid as a model reaction
Aida, Shin,Terao, Kimitada,Nishiyama, Yasuhiro,Kakiuchi, Kiyomi,Oelgem?ller, Michael
, p. 5578 - 5581 (2012/11/13)
The continuous-microflow photochemical synthesis of terebic acid from maleic acid was investigated in two different microreactor set-ups. The results were subsequently compared to analogue experiments in a conventional chamber reactor. Based on conversion rates, reactor design and energy efficiency calculations, the simple microcapillary reactor showed the best overall performance.
