- Green solvents from glycerol. Synthesis and physico-chemical properties of alkyl glycerol ethers
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A family of glycerol derivatives, consisting of over sixty 1,3-dialkoxy-2-propanols and 1,2,3-trialkoxypropanes, both symmetrically and unsymmetrically substituted at terminal positions, have been synthesized and the possible role of these glycerol derivatives as substitutive solvents has been evaluated through measurements of their physico-chemical properties. The molecular diversity of the derivatives prepared results in significant variations of polarity properties, facilitating the identification of possible candidates for solvent substitution.
- Garcia, Jose I.,Garcia-Marin, Hector,Mayoral, Jose A.,Perez, Pascual
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- Readily Scalable Methodology for the Synthesis of Nonsymmetric Glyceryl Diethers by a Tandem Acid-/Base-Catalyzed Process
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A useful optimized synthetic methodology has been designed for the synthesis of nonsymmetric glyceryl diethers from epichlorohydrin. A tandem process combining a cheap, heterogeneous, and fully recoverable acid catalyst and alkaline hydroxide is used for the synthesis of a variety of glycerol-derived ethers bearing different alkyl substituents in 1 and 3 positions. Different heterogeneous acid catalysts have been tested for the reaction of epichlorohydrin with several alcohols, the best results being obtained with readily available recoverable and inexpensive montmorillonite-K10 and Nafion NR50. For the second reaction step, potassium hydroxide is used. In all the cases, good yields of the desired glyceryl diethers are obtained in smooth reaction conditions, always with total conversion of epichlorohydrin and without the need of intermediate purification. Scale-up of the tandem process has been carried out with good results.
- Leal-Duaso, Alejandro,Gracia-Barberán, Sara,Mayoral, José A.,Garciá, José I.,Pires, Elisabet
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- An Fe3O4 nanoparticle-supported Mn (II)-azo Schiff complex acts as a heterogeneous catalyst in alcoholysis of epoxides
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In this paper, an azo-containing Schiff base complex of manganese [Mn2+-azo ligand@APTES-SiO2@Fe3O4] immobilized on chemically modified Fe3O4 nanoparticles has been used as a magnetically retrievable catalyst for the alcoholysis of different epoxides to their corresponding alkoxy alcohols with methanol, ethanol and n-propanol. The newly magnetic nanoparticles (MNPs) were characterized by Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX) and vibrating sample magnetometry (VSM).
- Olia, Fahimeh Karami,Sayyahi, Soheil,Taheri, Narges
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- A highly efficient protocol for regioselective ring-opening of epoxides with alcohols, water, acetic acid, and acetic anhydride catalyzed by SbF3
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SbF3as an efficient catalyst has been used for regioselective alcoholysis, acetolysis and hydrolysis of epoxides to the corresponding β-alkoxy, β-acetoxy alcohols, and 1,2-diols in high to excellent yields. This study also represents a convenient synthesis of vic-diacetates from ring-opening of epoxides with acetic anhydride.
- Zeynizadeh, Behzad,Gilanizadeh, Masumeh,Aminzadeh, Farkhondeh Mohammad
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p. 1051 - 1056
(2016/07/06)
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- Investigation of the catalytic activity of an electron-deficient vanadium(IV) tetraphenylporphyrin: A new, highly efficient and reusable catalyst for ring-opening of epoxides
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In this work, the catalytic activity of high-valent tetraphenylporphyrinatovanadium(IV) trifluoromethanesulfonate, [V IV(TPP)(OTf)2], in the nucleophilic ring-opening of epoxides is reported. This new V(IV) catalyst was used as an efficient catalyst for alcoholysis with primary (methanol, ethanol and n-propanol), secondary (iso-propanol) and tertiary alcohols (tert-butanol), hydrolysis and acetolysis of epoxides with acetic acid and also for the conversion of epoxides to 1,2-diacetates with acetic anhydride, conversion of epoxides to thiiranes with ammonium thiocyanate and thiourea, and for conversion of epoxides to acetonides with acetone. The catalyst was reused several times without loss of its activity.
- Taghavi, S. Abdolmanaf,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Tangestaninejad, Shahram,Mirkhani, Valiollah,Khosropour, Ahmad Reza,Ahmadi, Venus
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experimental part
p. 2244 - 2252
(2011/10/03)
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- Mild and efficient ring opening of epoxides catalyzed by potassium dodecatungstocobaltate(III)
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Efficient ring opening of epoxides under mild conditions is reported. Potassium dodecatungstocobaltate(III) trihydrate was used as an efficient catalyst for the alcoholysis and acetolysis of epoxides. Conversion of epoxides to thiiranes was also performed efficiently in the presence of this catalyst. Springer-Verlag 2005.
- Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah,Yadollahi, Bahram,Mirmohammadi, S. Mohammad R.
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p. 235 - 242
(2007/10/03)
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- Rapid and efficient ring opening of epoxides catalyzed by a new electron deficient tin(IV) porphyrin
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The new electron deficient tin(IV) tetraphenylporphyrinato trifluoromethanesulfonate, [SnIV(tpp)(OTf)2], was used as an efficient catalyst for the alcoholysis, hydrolysis and acetolysis of epoxides. Conversion of epoxides to thiiranes and acetonides were also performed efficiently in the presence of this catalyst.
- Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Shaibani, Reza
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p. 6105 - 6111
(2007/10/03)
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- Efficient regio- and stereoselective ring opening of epoxides with alcohols, acetic acid and water catalyzed by ammonium decatungstocerate(IV)
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Epoxides can be cleaved in a regio- and stereoselective manner under neutral conditions with alcohols and acetic acid in the presence of catalytic amounts of decatungstocerate(IV) ion, ([CeW10O36] 8-), affording the corresponding β-alkoxy and β-acetoxy alcohols in high yields. In water, ring opening of epoxides occurs with this catalyst to produce the corresponding diols in good yields.
- Mirkhani, Valiollah,Tangestaninejad, Shahram,Yadollahi, Bahram,Alipanah, Ladan
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p. 8213 - 8218
(2007/10/03)
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- Ferric perchlorate: An efficient reagent for regio- and stereoselective alcoholysis and hydrolysis of epoxides
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Regio- and stereoselective ring opening reaction of epoxides is achieved efficiently by aliphatic alcohols and water in the presence of catalytic amounts of ferric perchlorate.
- Salehi, Peyman,Seddighi, Behnam,Irandoost, Mohsen,Kargar Behbahani, Farahnaz
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p. 2967 - 2973
(2007/10/03)
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- Bismuth(III) chloride (BiCl3); an efficient catalyst for mild, regio- and stereoselective cleavage of epoxides with alcohols, acetic acid and water
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Epoxides can be cleaved in a regio- and stereoselective manner with alcohols, acetic acid and water in the presence of catalytic amounts of bismuth(III) chloride, affording the corresponding β-alkoxy and β-acetoxy alcohols and diols in high yields.
- Mohammadpoor-Baltork,Tangestaninejad,Aliyan,Mirkhani
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p. 2365 - 2374
(2007/10/03)
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- FeCl3·6H2O supported on SiO2 catalysed ring opening of epoxides with alcohols, acetic acid, water, chloride, bromide and nitrate ions
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FeCl3·6H2O absorbed on chromatographic silica gel can act as an efficient catalyst for alcoholysis, hydrolysis and acetolysis of epoxides. Methanolysis of (R)-styrene oxide proceeds with high stereospecificity and in excellent yield. This catalyst can also convert epoxides to their corresponding β-halohydrins and β-nitrato alcohols in the presence of chloride, bromide and nitrate ions respectively.
- Iranpoor, Nasser,Tarrian, Tahere,Movahedi, Zarangiz
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p. 1473 - 1476
(2007/10/03)
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- Highly efficient, regio- and stereoselective alcoholysis of epoxides catalyzed with iron(III) chloride
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An efficient, catalytic, simple and mild method for the conversion of epoxides into their corresponding β-alkoxy alcohols was performed in primary, secondary and tertiary alcohols and in the presence of catalytic amounts of ferric chloride. The β-alkoxy alcohols were obtained with high stereo- and regioselectivity and in good to excellent yields.
- Iranpoor,Salehi
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p. 1152 - 1154
(2007/10/02)
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