- Catalytic Hydrogenolysis of Solketal on Bifunctional Catalysts with Production of High Octane Components of Motor Fuels
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The possibility of implementing the concept of converting bioglycerin into a blend of oxygenates, potentially applicable as components of gasoline by ketalization with acetone (T = 30°C–40°C, atmospheric pressure), accompanied by mild hydrogenolysis of ketal [T = 100°C–140°C, p(H2) = 2 MPa] to obtain a mixture of of glycerol and solketal isopropyl ethers was demonstrated. Results showed that the preferred method of conversion was the separate performing of ketalization and hydrogenolysis, since when these stages are combined, the side reaction of the formation of free isopropyl alcohol was highly selective. The regularities in the influence of the composition of the catalytic system (Pd/C + para-toluenesulfonic acid) on its activity were observed in the reaction of catalytic hydrogenation of solketal to a mixture of glycerol and solketal isopropyl ethers (optimal ratio of Pd/para-toluenesulfonic acid = 0.811 mol). The addition of 4%–5% glycerol to raw materials increased the yield of target hydrogenation products from 25% to 36%. Using a flow unit, the catalytic hydrogenation of solketal was optimized. In the optimal mode [T = 170°C, p(H2) = 4 MPa, v = 0.5 h?1, H2/feedstock = 660 nL L?1], the conversion of solketal to a mixture of target products (glycerol monoisopropyl ether, glycerol diisopropyl ethers, and solketal isopropyl ether) reached 98%. The possibility of carrying out the reaction on heterogeneous bifunctional catalysts of the Pd/sulfonated coal type was shown.
- Goncharova, A. V.,Knyazeva, M. I.,Maksimov, A. L.,Ni, D. S.,Ramazanov, D. N.,Samoilov, V. O.
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- Glycerol Isopropyl Ethers: Direct Synthesis from Alcohols and Synthesis by the Reduction of Solketal
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The catalytic reduction of solketal ((2,2-dimethyl-1,3-dioxolan-4-yl)methanol) over bifunctional heterogeneous palladium catalysts is proposed as an alternative to the synthesis of glycerol isopropyl ethers by the etherification of glycerol. The direct synthesis of glycerol isopropyl ethers from isopropanol and glycerol requires severe conditions (T=130–150 °C, p(H2)=20–35 bar) and a large excess of isopropanol to reach a considerable yield. The main reaction products in the catalytic reduction of solketal are glycerol mono- and di-isopropyl ethers and solketal isopropyl ether. Solketal conversion over Al-HMS-supported palladium catalysts (T=120 °C and p(H2)=20 bar) affords a mixture of ethers with a high degree of conversion (87 %), 78 % selectivity, and excellent regioselectivity between isomeric ethers. Zeolite-BEA-supported palladium catalysts also exhibit high activity but much lower selectivity because of intense acetone aldol condensation. The effects of Si/Al ratios in BEA zeolites and Al-HMS aluminosilicates and the amounts of supported palladium (1 and 2 wt %) on the properties of the catalysts at different reaction temperatures and hydrogen pressures are considered.
- Samoilov, Vadim O.,Onishchenko, Maria O.,Ramazanov, Dzhamalutdin N.,Maximov, Anton L.
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p. 2839 - 2849
(2017/07/28)
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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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- Ecotoxicity studies of glycerol ethers in Vibrio fischeri: checking the environmental impact of glycerol-derived solvents
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The toxicities of a series of glycerol mono-, di-, and trialkyl ethers against Vibrio fischeri bacteria have been determined. A systematic study has been carried out and the possible structure-toxicity relationships have been discussed using different QSAR models. Inhibition of bioluminescence after 30 minutes of exposure shows relatively low toxicity of many of the glycerol derived chemicals studied. Results indicate that, as a general rule, the ecotoxicity increases with the length and number of substituents. However, if the size of the molecule increases, an extra substituent at position 2 makes the toxicity lower than that of the corresponding analogues.
- Garca,Pires,Aldea,Lomba,Perales,Giner
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supporting information
p. 4326 - 4333
(2015/08/11)
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- Thermodynamic characteristics of the sorption of glycerol ethers on stationary phase OV-101
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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
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p. 1590 - 1593
(2014/10/16)
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- Surfactant compositions and use for aqueous compositions
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A surfactant composition selected from the group consisting of: (R1O)CH2CH(OCH2CH2)1-20OHCH2(OR2) and mixtures thereof, wherein at least one of R1 and R2 are secondary alkyl groups including from 3 to 9 Carbon atoms; an aqueous coating composition including an aqueous polymeric dispersion; and certain other compositions including the surfactant composition are provided. Also provided is a method for forming a coating.
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Page/Page column
(2014/04/03)
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- SURFACTANT COMPOSITIONS AND USE FOR AQUEOUS COMPOSITIONS
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A surfactant composition selected from the group consisting of; (R1O)CH2CH(OCH2CH2)1-20OHCH2(OR2) and mixtures thereof; wherein at least one of R1 and R2 are secondary alkyl groups including from 3 to 9 Carbon atoms; an aqueous coating composition including an aqueous polymeric dispersion; and certain other compositions including the surfactant composition are provided. Also provided is a method for forming a coating.
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Paragraph 0030
(2014/04/03)
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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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- 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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experimental part
p. 426 - 434
(2010/08/07)
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- POLYOL ETHERS AND PROCESS FOR MAKING THEM
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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.
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Page/Page column 10
(2010/03/31)
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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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- Synthesis of 2,5-dihydrofurans via alkylidene carbene insertion reactions
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The insertion reaction of alkylidene carbenes is demonstrated to be an effective method for the synthesis of 2,5-dihydrofuran ring systems. The best results have been obtained on substrates containing electron-withdrawing substituents, which appear less prone to the competing rearrangement reaction. This insight has led to the development of a new method for the synthesis of the core structure of the squalestatin-zaragozic acid natural products.
- Walker, Louise F.,Bourghida, Ahmed,Connolly, Stephen,Wills, Martin
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p. 965 - 981
(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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