Glycerol to renewable fuel oxygenates. Part I: Comparison between solketal and its methyl ether

Samoilov, Vadim O.; Maximov, A. L.; Stolonogova, T. I.; Чернышева, Е. А.; Капустин, В. М.; Karpunina, A.O.

doi:10.1016/j.fuel.2019.02.098

Cited by 34 publications

(26 citation statements)

References 35 publications

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“…The equilibrium yield values for the reactions of 2,3-BD and 1,2-PD ketalization are close to the values measured for glycerol ketalization under the similar conditions [52,53]. Pure TMD and ETMD samples were obtained via the direct ketalization under the same ketone molar excess (6:1) conditions.…”

Section: The Ketalization Of 12-pd and 23-bd With Acetone And Meksupporting

confidence: 75%

“…It is of big concern that the molecular structure of TMD resembles the solketal molecule but without an OH-group. The methylation of the solketal OH-group was shown earlier to result in a dramatic ON decrease [53], and it was the OH-group (not the 2,2-dimethyl-1,3-dioxolane moiety) which was responsible for the good antiknock performance. In the present case, the octane rating of the 2,2-dimethyl-1,3-dioxolane derivative is obviously quite high.…”

Section: The Characterization Of the Productsmentioning

confidence: 87%

“…The determination of equilibrium compositions was carried out under the conditions employed earlier for the ketalization between acetone and glycerol [52,53]. During the analysis of the reaction mixtures, no byproducts were observed.…”

Section: The Ketalization Of 12-pd and 23-bd With Acetone And Mekmentioning

confidence: 99%

“…As the tested oxygenates' boiling points are inside the gasoline boiling range • C), their volatilities can be considered acceptable. The main concern here is that the "excessively heavy" oxygenates can decrease the overall gasoline volatility, what could be particularly relevant for high-boiling solketal [53], γ-valerolactone [63], methyl pentanoate and alkyl levulinates [64]. The results of the fractional composition, namely, the 5 and 10 vol.…”

Section: The Characterization Of the Productsmentioning

confidence: 99%

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Bio-Based Solvents and Gasoline Components from Renewable 2,3-Butanediol and 1,2-Propanediol: Synthesis and Characterization

Samoilov

Goncharova

et al. 2020

Molecules

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In this study approaches for chemical conversions of the renewable compounds 1,2-propanediol (1,2-PD) and 2,3-butanediol (2,3-BD) that yield the corresponding cyclic ketals and glycol ethers have been investigated experimentally. The characterization of the obtained products as potential green solvents and gasoline components is discussed. Cyclic ketals have been obtained by the direct reaction of the diols with lower aliphatic ketones (1,2-PD + acetone → 2,2,4-trimethyl-1,3-dioxolane (TMD) and 2,3-BD + butanone-2 → 2-ethyl-2,4,5-trimethyl-1,3-dioxolane (ETMD)), for which the ΔH0r, ΔS0r and ΔG0r values have been estimated experimentally. The monoethers of diols could be obtained through either hydrogenolysis of the pure ketals or from the ketone and the diol via reductive alkylation. In the both reactions, the cyclic ketals (TMD and ETMD) have been hydrogenated in nearly quantitative yields to the corresponding isopropoxypropanols (IPP) and 3-sec-butoxy-2-butanol (SBB) under mild conditions (T = 120–140 °C, p(H2) = 40 bar) with high selectivity (>93%). Four products (TMD, ETMD, IPP and SBB) have been characterized as far as their physical properties are concerned (density, melting/boiling points, viscosity, calorific value, evaporation rate, Antoine equation coefficients), as well as their solvent ones (Kamlet-Taft solvatochromic parameters, miscibility, and polymer solubilization). In the investigation of gasoline blending properties, TMD, ETMD, IPP and SBB have shown remarkable antiknock performance with blending antiknock indices of 95.2, 92.7, 99.2 and 99.7 points, respectively.

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Section: The Ketalization Of 12-pd and 23-bd With Acetone And Meksupporting

confidence: 75%

Section: The Characterization Of the Productsmentioning

confidence: 87%

Section: The Ketalization Of 12-pd and 23-bd With Acetone And Mekmentioning

confidence: 99%

Section: The Characterization Of the Productsmentioning

confidence: 99%

See 2 more Smart Citations

Bio-Based Solvents and Gasoline Components from Renewable 2,3-Butanediol and 1,2-Propanediol: Synthesis and Characterization

Samoilov

Goncharova

et al. 2020

Molecules

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“…The reaction between acetone and glycerol is presented in Scheme 1, where (1) solketal (2,2-dimethyl-1, 3-dioxolone-4-methanol), (2) acetal (1,3-dioxan-5-ol) and water are formed over an acid catalyst [10]. Solketal is used as a solvent, low-temperature heat-transfer fluid, surfactant and as an oxygenated additive to improve biofuel properties, such as cold flow, viscosity, or octane index, as an alternative to commercial trialkylethers (MTBE and ETBE) [11]. As has been reported in the literature [12], the production of cyclic acetals or ketals is favored in the presence of Brönsted acid catalysts.…”

Section: Introductionmentioning

confidence: 99%

Continuous-Flow Process for Glycerol Conversion to Solketal Using a Brönsted Acid Functionalized Carbon-Based Catalyst

et al. 2019

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The acetalization of glycerol with acetone represents a strategy for its valorization into solketal as a fuel additive component. Thus, acid carbon-based structured catalyst (SO3H-C) has been prepared, characterized and tested in this reaction. The structured catalyst (L = 5 cm, d = 1 cm) showed a high surface density of acidic sites (2.9 mmol H+ g−1) and a high surface area. This catalyst is highly active and stable in the solketal reaction production in a batch reactor system and in a continuous downflow reactor, where several parameters were studied such as the variation of time of reaction, temperature, acetone/glycerol molar ratio (A/G) and weight hourly space velocity (WHSV). A complete glycerol conversion and 100% of solketal selectivity were achieved working in the continuous flow reactor equipped with distillation equipment when WHSV is 2.9 h−1, A/G = 8 at 57 °C in a co-solvent free operation. The catalyst maintained its activity under continuous flow even after 300 min of reaction.

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Thermodynamic equilibrium analysis on the dehydration of glycerol with monohydric alcohols to alkyl glyceryl ethers

Jia

et al. 2022

AIChE Journal

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Under the conditions of the feed of 400 moles of alcohol + 100 moles of glycerol, 313-573 K and 0.1 MPa, based on Gibbs free energy global minimization, an improved genetic algorithm was used for the thermodynamic equilibrium analysis on the synthesis processes of alkyl glyceryl ethers, respectively, from methanol + glycerol, ethanol + glycerol, isobutanol + glycerol, and tert-butanol + glycerol. The columnar stacking charts and three-dimensional contour graphs were used to compare the effects of temperature, pressure, and the feed ratio to the equilibrium conversion, product selectivity, and equilibrium composition. The basic laws of the synthesis processes of alkyl glycerol ethers in homogeneous and heterogeneous states were investigated in a wide temperature range. Through comparison, it was found that the isopropanol + glycerol system is easier to convert into alkyl glycerol ethers, followed by the ethanol + glycerol system. The methanol + glycerol system and tert-butanol + glycerol system are greatly affected by pressure and temperature, and their conversions and selectivities are relatively low.

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Glycerol to renewable fuel oxygenates. Part I: Comparison between solketal and its methyl ether

Cited by 34 publications

References 35 publications

Bio-Based Solvents and Gasoline Components from Renewable 2,3-Butanediol and 1,2-Propanediol: Synthesis and Characterization

Bio-Based Solvents and Gasoline Components from Renewable 2,3-Butanediol and 1,2-Propanediol: Synthesis and Characterization

Continuous-Flow Process for Glycerol Conversion to Solketal Using a Brönsted Acid Functionalized Carbon-Based Catalyst

Thermodynamic equilibrium analysis on the dehydration of glycerol with monohydric alcohols to alkyl glyceryl ethers

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