- Regioselective Ring-Opening of Glycidol to Monoalkyl Glyceryl Ethers Promoted by an [OSSO]-FeIII Triflate Complex
-
A FeIII-triflate complex, bearing a bis-thioether-di-phenolate [OSSO]-type ligand, was discovered to promote the ring-opening of glycidol with alcohols under mild reaction conditions (0.05 mol % catalyst and 80 °C). The reaction proceeded with high activity (initial turnover frequency of 1680 h?1 for EtOH) and selectivity (>95 %) toward the formation of twelve monoalkyl glyceryl ethers (MAGEs) in a regioselective fashion (84–96 % yield of the non-symmetric regioisomer). This synthetic approach allows the conversion of a glycerol-derived platform molecule (i.e., glycidol) to high-value-added products by using an Earth-crust abundant metal-based catalyst.
- Monica, Francesco Della,Ricciardi, Maria,Proto, Antonio,Cucciniello, Raffaele,Capacchione, Carmine
-
-
Read Online
- Heterogeneous catalytic conversion of glycerol with n-butyl alcohol
-
The etherification of glycerol with n-butyl alcohol at 140°C in the presence of sulfonated cation-exchange resins and zeolite catalysts in an autoclave reactor has been studied. It has been shown that styrene - divinylbenzene ion-exchange resins are effective catalysts for the production of glycerol n-butyl ethers: the glycerol conversion is about 98% with an n-butyl ether selectivity of about 88 mol % (140°C, 5 h, 5 wt % Amberlyst 36 catalyst, and 10 wt % glycerol in n-butanol). Zeolites Y and β in the H+ form exhibit comparable specific activity (glycerol conversion of no more than 25% under similar conditions) in combination with high selectivity for glycerol di-n-butyl ethers (up to 28%).
- Samoilov,Ramazanov,Nekhaev,Maksimov
-
-
Read Online
- Synthesis of Monoalkyl Glyceryl Ethers by Ring Opening of Glycidol with Alcohols in the Presence of Lewis Acids
-
The present work deals with the production of monoalkyl glyceryl ethers (MAGEs) through a new reaction pathway based on the reaction of glycidol and alcohols catalyzed by Lewis acid-based catalysts. Glycidol is quantitatively converted with high selectivity (99 %) into MAGEs under very mild reaction conditions (80 °C and 0.01 mol % catalyst loading) in only 1 h using Al(OTf)3 or Bi(OTf)3 as catalyst. The proposed method enhances the choice of possible green synthetic approaches for the production of value-added products such as MAGEs.
- Cucciniello, Raffaele,Ricciardi, Maria,Vitiello, Rosa,Di Serio, Martino,Proto, Antonio,Capacchione, Carmine
-
p. 3272 - 3275
(2016/12/16)
-
- Thermodynamic characteristics of the sorption of glycerol ethers on stationary phase OV-101
-
Retention characteristics, temperature dependences of the retention characteristics, and thermodynamic characteristics of sorption on the nonpolar OV-101 phase are determined for 33 glycerol mono-, di-, and triethers with linear and branched monobasic alc
- Zhabina,Krasnykh,Levanova
-
p. 1590 - 1593
(2014/10/16)
-
- Catalytic etherification of glycerol with short chain alkyl alcohols in the presence of Lewis acids
-
Here we report the homogeneously-catalyzed etherification of glycerol with short chain alkyl alcohols. Among the large variety of Bronsted and Lewis acids tested, we show here that metal triflates are not only the most active but are also capable of catalyzing this reaction with an unprecedented selectivity. In particular, in the presence of Bi(OTf)3, the targeted monoalkylglyceryl ethers were obtained with up to 70% yield. Although tested Bronsted acids were also capable of catalyzing the etherification of glycerol with alkyl alcohols, they were found however less active and less selective than Bi(OTf)3. By means of counter experiments, we highlighted that the high activity and selectivity of Bi(OTf)3 may rely on a synergistic effect between Bi(OTf)3 and triflic acid, a Bronsted acid that can be released by in situ glycerolysis of Bi(OTf)3. The scope of this methodology was also extended to other polyols and, in all cases, the monoalkylpolyol ethers were conveniently obtained with fair to good yields.
- Liu, Fei,De Oliveira Vigier, Karine,Pera-Titus, Marc,Pouilloux, Yannick,Clacens, Jean-Marc,Decampo, Floryan,Jerome, Francois
-
p. 901 - 909
(2013/07/26)
-
- PRODUCTION OF HYDROXY ETHER HYDROCARBONS BY LIQUID PHASE HYDROGENOLYSIS OF CYCLIC ACETALS OR CYCLIC KETALS
-
A liquid phase hydrogenolysis of acetal compounds such as cyclic acetals and cyclic ketals are fed to a reaction zone and reacted in the presence of a noble metal catalyst supported on a carbon or silica support to make hydroxy ether mono-hydrocarbons in high selectivity, without the necessity to use acidic co-catalysts such as phosphorus containing acids or stabilizers such as hydroquinone.
- -
-
Page/Page column 9
(2013/02/28)
-
- PROCESS FOR MAKING POLYOL ETHERS
-
The present invention generally relates to a process for making polyol ethers by reacting a polyol and a carbonyl compound together in the presence of hydrogen gas and a palladium hydrogenation catalyst on an acidic mesoporous carbon support.
- -
-
Page/Page column 15
(2011/09/16)
-
- Acid-catalyzed etherification of glycerol with long-alkyl-chain alcohols
-
Rubbing the right way: The direct etherification of glycerol with long-chain alcohols typically suffers from poor contact between the reaction phases. A dodecylbenzene sulfonic acid catalyst enables a better contact between the glycerol and alcohol phases, enhancing the yield of monoalkyl glyceryl ethers and offering a direct route for the synthesis of these surfactants. Copyright
- Gaudin, Pierrick,Jacquot, Roland,Marion, Philippe,Pouilloux, Yannick,Jér?me, Fran?ois
-
experimental part
p. 719 - 722
(2012/05/20)
-
- POLYOL ETHERS AND PROCESS FOR MAKING THEM
-
New polyol ether compounds and a process for their preparation. The process comprises reacting a polyol, a carbonyl compound, and hydrogen in the presence of hydrogenation catalyst, to provide the polyol ether. The molar ratio of polyol to carbonyl compound in the process is greater than 5:1.
- -
-
Page/Page column 8
(2010/03/31)
-