4740-78-7Relevant articles and documents
An efficient method for the refinement of 1,3-methyleneglycerol via bridged acetal exchange and the synthesis of a symmetrically branched glycerol trimer
Hattori, Hatsuhiko,Matsushita, Tsuyoshi,Yoshitomi, Kohsuke,Katagiri, Ayato,Nemoto, Hisao
, p. 2365 - 2373 (2012)
Acid-catalyzed equilibrium of a mixture of 1,2- and 1,3-methyleneglycerol in 1,4-dioxane affords predominantly the 1,3-isomer via bridged acetal exchange. The minor 1,2-isomer is removed via sequential pivaloylation and tritylation to afford the desired 1,3-isomer in >99.5% purity. A symmetrically branched triglycerol is efficiently synthesized starting from the purified 1,3-isomer. Georg Thieme Verlag Stuttgart · New York.
Mesoporous Zr-SBA-16 catalysts for glycerol valorization processes: Towards biorenewable formulations
Gonzalez-Arellano, Camino,Parra-Rodriguez, Leticia,Luque, Rafael
, p. 2287 - 2292 (2014)
Zr-containing SBA-16 materials were utilized in glycerol valorization for the production of esters (via reaction with levulinic acid) and glycerol formal (GF) via acetalisation with paraformaldehyde. The materials were found to be highly active and selective for the production of valuable compounds from glycerol using benign by design solventless protocols which employ mild reaction conditions. Certain materials were also found to be highly reusable and stable under the investigated conditions.
Interaction of triols with formaldehyde and acetone: Experimental and theoretical study
Sultanova, Rimma,Borisevich, Sophia,Raskil'dina, Gulnara,Borisova, Julianna,Baykova, Irina,Spirikhin, Leonid,Khursan, Sergey,Zlotsky, Simon
, p. 1144 - 1151 (2020/02/25)
Experimental and theoretical aspects of the condensation of glycerol and its homologs (1,2,3- and 1,2,4-butanetriols) with formaldehyde and acetone are studied under conditions of acid catalysis. Calculation of the thermodynamic parameters of the resulting products by the composite method CBS-QB3 shows that the six-membered heterocycles, the products of the interaction of triols with formaldehyde, are thermodynamically more stable than the five-membered acetals, while the reaction of the same triols with acetone is preferable for the formation of the five-membered acetals. This is due to the fact that the regioselectivity of the studied reactions is determined by the structural features and reactivity of the carbocations formed in a condensed medium during the course of the reaction. According to the theoretical data obtained experimentally, during the condensation of glycerol and 1,2,4-butanetriol with formaldehyde in the most stable form of the six-membered cyclic carbocation, intramolecular hydrogen bonding and anomeric stabilization due to the axially oriented hydroxyl group take place. As a result, cation 1b–1 is 1.2–1.6 kJ/mol more stable than its five-membered isomers (1a–1 and 1b–2). It leads to the predominant formation of 1,3-dioxane (3b). However, upon condensation of butanetriol-1,2,3 with formaldehyde, the intermediate cation 4a–1 turns out to be significantly more stable than the other isomers due to the strong intramolecular hydrogen bond in the six-membered ring with the participation of the hydroxyl group of the substituent and the hydroxyl group of the cationic center, leading to the predominant formation of the dioxolane 6a.
Method for preparing glycerolformal
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Paragraph 0029-0034, (2019/04/11)
The invention discloses a method for preparing glycerolformal. According to the invention, SO42-/Fe2O3-CNTS super acid is used as a catalyst for compounding glycerolformal, so that the method has theadvantages that reaction temperature is low, catalyst activity is high, no new water-carrying agent is brought, yield of reaction products is 95% or above and hexatomic ring products are high in proportion.