Improving the separation of guaiacol from n-hexane by adding choline chloride to glycol extracting agents

Arroyo-Avirama, Andrés F.; Ormazábal-Latorre, Sebastián; Jogi, Ramakrishna; Gajardo‐Parra, Nicolás F.; Pazo-Carballo, César; Ascani, Moreno; Virtanen, Pekka; Garrido, José Matías; Held, Christoph; Mäki‐Arvela, Päivi; Canales, Roberto I.

doi:10.1016/j.molliq.2022.118936

Cited by 16 publications

(8 citation statements)

References 85 publications

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“…However, as the viscosity of the solvents is on the same order of magnitude as isoeugenol, a parabolic behavior can be observed in each case for isoeugenol + ethylene glycol (Figure B), isoeugenol + diethylene glycol (Figure C), and isoeugenol + 1,3-propanediol (Figure D). Such behavior was observed before for another methoxyphenol, i.e., guaiacol, mixed with glycols Figure also compares the capacity of PC-SAFT to predict the viscosity of isoeugenol + solvent systems using entropy scaling theory.…”

Section: Resultssupporting

confidence: 68%

“…Such behavior was observed before for another methoxyphenol, i.e., guaiacol, mixed with glycols. 34 Figure 4 also compares the capacity of PC-SAFT to predict the viscosity of isoeugenol + solvent systems using entropy scaling theory. As we can see in the quoted figure, the quality of the prediction of the entropy scaling and PC-SAFT varies in the middle range of concentrations for isoeugenol and ethylene glycol (Figure 4B), given the convoluted behavior of the molecules in the mixture.…”

Section: ∞Smentioning

confidence: 99%

“…32 In previous works, our group studied the liquid−liquid equilibrium of guaiacol + aliphatic compounds + acetone, short-chain alcohols, glycols, and glycol-based deep eutectic solvents. 33,34 However, due to the complexity of bio-oil, extensive studies are necessary to ensure the correct choice of solvent for the separation process. Tao et al 35 performed a multiple-stage extraction using NaOH to separate the light and heavy fractions and then separate the compounds by distillation.…”

Section: ■ Introductionmentioning

confidence: 99%

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Separation of Isoeugenol from Methylcyclohexane as a Model Mixture of Biojet Fuel Purification: Solvent Selection and Liquid–Liquid Equilibrium

Espinoza-Cartagena,

Ormazábal-Latorre,

Pazo-Carballo

et al. 2023

Ind. Eng. Chem. Res.

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The biorefinery concept emerged as an opportunity to reduce the negative effects of climate change and as a potential source of products for the fuel industry, where jet fuel produced by hydrodeoxygenation of bio-oil (denominated as biojet fuel) is of special interest. However, the presence of highly oxygenated species makes this kind of jet fuel unsuitable as a final product. Thus, it is necessary to remove phenolic compounds from its complex matrix, but the study of solvent extraction of phenolic compounds as an upgrading of a bio-oil matrix requires a thermodynamic framework to reduce the experimental effort. In this work, isoeugenol was selected as a model phenolic molecule from biojet fuel, while methylcyclohexane was selected as a representative cyclic alkane solvent from jet fuel. Three solvents were selected by a screening based on a conductor-like screening model for real solvents (COSMO-RS) to test their capability to extract isoeugenol from methylcyclohexane. The selected solvents were ethylene glycol, diethylene glycol, and 1,3-propanediol. The density and viscosity were measured for all pure compounds and the mixtures of isoeugenol + (methylcyclohexane or extracting solvent) at 101.3 kPa and temperatures from 293.15 to 333.15 K. The liquid−liquid equilibrium was also measured for all the systems of isoeugenol + methylcyclohexane + extracting solvent at 101.3 kPa and 313.15 K. Density and liquid−liquid equilibrium data were modeled with perturbed-chain statistical associating fluid theory (PC-SAFT). Viscosity was modeled using the PC-SAFT + entropy scaling theory. The results indicate that isoeugenol has a higher affinity with the selected extracting solvents than methylcyclohexane, since the excess volume for binary mixtures of isoeugenol + extracting solvent exhibits negative values, while isoeugenol + methylcyclohexane exhibits mainly positive values. The selectivity and distribution coefficient values obtained support the idea that selected solvents are good for extracting isoeugenol, where diethylene glycol is the best alternative. PC-SAFT accurately represents the liquid−liquid equilibrium with only binary interaction parameters between methylcyclohexane and the selected solvents. Then, this model can be used as a tool for the analysis and simulation of processes of isoeugenol separation in more complex liquid mixtures.

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Section: Resultssupporting

confidence: 68%

Section: ∞Smentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Separation of Isoeugenol from Methylcyclohexane as a Model Mixture of Biojet Fuel Purification: Solvent Selection and Liquid–Liquid Equilibrium

Espinoza-Cartagena,

Ormazábal-Latorre,

Pazo-Carballo

et al. 2023

Ind. Eng. Chem. Res.

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“…A summary of all calculated absolute deviations (AD) and average absolute deviations is given in Tables S2, S3, and S4, respectively, for the solubility measurements of the BHET monomer, the BHET dimer, and PET, in the Supporting Information. The pure-component parameters for the solvents DMSO, GVL, EG, and H 2 O were retrieved from the literature. − Given the structural similarities among the BHET monomer, the BHET dimer, and PET, particularly with respect to the terephthalic acid segment group, the binary interaction parameter k ij between one of these molecules with the same solvent was assumed to be equal. The melting temperatures and enthalpies were taken from Table .…”

Section: Resultsmentioning

confidence: 99%

Measurement and PC-SAFT Modeling of the Solubility of the BHET Monomer, the BHET Dimer, and PET in Single Solvents

Schlüter,

Bhutani,

Bahr

et al. 2024

J. Chem. Eng. Data

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Poly(ethylene terephthalate) (PET) glycolysis is a chemical recycling method to depolymerize PET with ethylene glycol (EG) into the monomer bis(2-hydroxyethyl) terephthalate (BHET). The BHET monomer to BHET dimer formation might occur as well. Solubility is a key property for the depolymerization process, but comprehensive investigations on the solubilities of the BHET monomer, the BHET dimer, and PET are still scarce. Therefore, this study aimed at determining the solubility of the BHET monomer in dimethyl sulfoxide (DMSO), γ-valerolactone (GVL), EG, and H 2 O between 20 and 86 °C. Additionally, the solubility of the BHET dimer was measured in DMSO, GVL, and EG between 23 and 125 °C, while the solubility of PET was determined in DMSO and GVL between 168 and 192 °C. These measurements were conducted at 1 bar. Besides, the solubility of PET in EG was measured at 4 bar between 225 and 235 °C. Perturbed-chain statistical associating fluid theory (PC-SAFT) was used to model the solubilities accurately. In summary, this research seeks to shed light on the solubility behavior of key components involved in PET glycolysis, whereby PC-SAFT turned out to be a reliable tool with semipredictive character toward PET modeling.

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“…Regarding LLE, few researchers have used organic solvents to extract bio-oil components [1,3,[20][21][22][23][24][25], much less for bio-oil from TAG biomass, aiming at its upgrading. In addition, the few studies that use LLE with organic solvents to separate oxygenated compounds use it to purify the aqueous phase, not the crude bio-oil itself.…”

Section: Introductionmentioning

confidence: 99%

Upgrading/Deacidification of Bio-Oils by Liquid–Liquid Extraction Using Aqueous Methanol as a Solvent

Machado,

Mota,

Leão

et al. 2024

Energies

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Oxygenated compounds such as acids in bio-oils (BO) have been related to the corrosion of metals and their storage instability when applied as fuels. Therefore, upgrading BO by removing acids (deacidification) can be a valuable technique to reduce corrosivity using specific separation processes. Therefore, the objective of this paper was to evaluate the effect of the water content in the solvent (aqueous methanol), the carboxylic acid content in the BO and extraction temperature on the deacidification process by liquid–liquid extraction (LLE), as well as the effect of the same parameters on the quality of the deacidified BO through physical–chemical and GC-MS analyses. The results show that an increase in the water content (5 to 25%) in the solvent and an increase in the carboxylic acids content (24.38 to 51.56 mg KOH/g) in the BO reduce the solvent’s capacity to extract carboxylic acids while increasing the temperature (25 to 35 °C) of the deacidification process promoted an increase in its capacity to remove them. Consequently, the highest deacidification efficiency (72.65%) is achieved with 5% water in methanol at 25 °C for BO1 (TAN = 24.38 mg KOH/g). Therefore, the deacidification process through LLE using aqueous methanol contributed significantly to BO upgrading.

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Improving the separation of guaiacol from n-hexane by adding choline chloride to glycol extracting agents

Cited by 16 publications

References 85 publications

Separation of Isoeugenol from Methylcyclohexane as a Model Mixture of Biojet Fuel Purification: Solvent Selection and Liquid–Liquid Equilibrium

Separation of Isoeugenol from Methylcyclohexane as a Model Mixture of Biojet Fuel Purification: Solvent Selection and Liquid–Liquid Equilibrium

Measurement and PC-SAFT Modeling of the Solubility of the BHET Monomer, the BHET Dimer, and PET in Single Solvents

Upgrading/Deacidification of Bio-Oils by Liquid–Liquid Extraction Using Aqueous Methanol as a Solvent

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