10215-30-2Relevant articles and documents
Catalytic deoxygenation of 1,2-propanediol to give n-propanol
Schlaf, Marcel,Ghosh, Prasenjit,Fagan, Paul J.,Hauptman, Elisabeth,Morris Bullock
, p. 789 - 800 (2009)
Deoxygenation of 1,2-propanediol (1.0M in sulfolane) catalyzed by bis(dicarbonyl)(μhydrido)(pentamethylcyclopentadiene)ruthenium trifluoromethanesulfonate ({[Cp*Ru(CO)2]2(μ.-H)} +OTf-) (0.5 mol%) at 110°C under hydrogen (750 psi) in the presence of trifluoromethanesulfonic acid (HOTf) (60 mM) gives n-propanol as the major product, indicating high selectivity for deoxygenation of the internal hydroxy group over the terminal hydroxy group of the diol. The deoxygenation of 1,2-propanediol is strongly influenced by the concentration of acid, giving faster rates and proceeding to higher conversions as the concentration of HOTf is increased. Propionaldehyde was observed as an intermediate, being formed through acid-catalyzed dehydration of 1,2-propanediol. This aldehyde is hydrogenated to n-propanol through an ionic pathway involving protonation of the aldehyde, followed by hydride transfer from the neutral hydride, dicarbonyl(pentamethylcyclopentadiene)ruthenium hydride [Cp*Ru(CO)2H]. The proposed mechanism for the deoxygenation/hydrogenation reaction involves formation of a highly acidic dihydrogen complex [Cp*Ru(CO)2(η2-H 2)]+ OTf-.
MBA-cross-linked poly(N-vinyl-2-pyrrolidone)/ferric chloride macromolecular coordination complex as a novel and recyclable Lewis acid catalyst: Synthesis, characterization, and performance toward for regioselective ring-opening alcoholysis of epoxides
Rahmatpour, Ali,Zamani, Maryam
, (2021/09/30)
A novel macromolecular-metal coordination complex, MBA-cross-linked PNVP/FeCl3 material was fabricated by immobilization of water intolerant ferric chloride onto the porous cross-linked poly(N-vinyl-2-pyrrolidone) carrier beads as a macromolecular ligand or carrier which was prepared by suspension free-radical copolymerization of N-vinyl-2-pyrrolidone (NVP) and N,N′-methylene bis-acrylamide (MBA) as a crosslinking agent in water. The obtained PNVP/FeCl3 was characterized by UV/vis and FT-IR spectroscopies, TGA, FE-SEM, EDX, and ICP techniques. This heterogenized version of ferric chloride is a convenient and safe alternative to highly water intolerant ferric chloride. The catalytic performance of (PNVP/FeCl3) as an efficient and recyclable polymeric Lewis acid catalyst was appropriately probed in the regio-and stereoselective nucleophilic ring opening of various epoxides with various alcohols in excellent yields with TOF up to 182.48 h?1 without generating any waste. The activity data indicate that this heterogeneous catalyst is very active and could be easily recovered, and reused at least six times without appreciable loss of activity indicating its stability under experimental conditions.
METHODS OF CONVERTING POLYOLS
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Paragraph 0091-0092, (2015/01/06)
Methods for converting polyols are provided. The methods provided can include using a metal pincer catalyst (e.g., an iridium pincer catalyst) to remove at least one alcohol group from a polyol. The methods provided can include converting glycerol to 1,3-propanediol.
Metal-catalyzed selective deoxygenation of diols to alcohols
Schlaf, Marcel,Ghosh, Prasenjit,Fagan, Paul J.,Hauptman, Elisabeth,Morris Bullock
, p. 3887 - 3890 (2007/10/03)
The internal OH group of 1,2-propanediol is selectively removed in the deoxygenation catalyzed by [{Cp*Ru(CO)2}2(μ-H)]+OTf - (1, Cp=C3Me5, OTf=trifluoromethanesulfonate; see scheme). This reaction provides a model for deoxygenation of polyols derived from carbohydrates, for use in alternative, biomass-based feedstock applications. An ionic mechanism is proposed that involves the dihydrogen complex [Cp*Ru(CO)2(η2-H2)]+.
The Use of Proton-exchanged X-Type Zeolite in Catalysing Ring-opening Reactions of 2-Substituted Epoxides with Nucleophiles and its Effect on Regioselectivity
Takeuchi, Hiroshi,Kitajima, Kunio,Yamamoto, Yasuhiro,Mizuno, Kiyokazu
, p. 199 - 203 (2007/10/02)
The use of proton-exchanged X-type zeolite in catalysing ring-opening reactions of 2-alkyl substituted epoxides with nucleophiles gives a high regioselectivity and functional-selective catalysis giving allylic products from allylic nucleophiles.Mechanistic aspects are discussed.