1,3-Dioxolane compounds (DOXs) as biobased reaction media

Melchiorre, Massimo; Budzelaar, Peter H. M.; Cucciolito, Maria Elena; Esposito, Roberto; Santagata, Emanuela; Ruffo, Francesco

doi:10.1039/d3gc00227f

Cited by 2 publications

(2 citation statements)

References 64 publications

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“…The resulting Δ cr l H m o is still quite low corresponding to a fusion entropy of 9.5 J·K –1 ·mol –1 , which is, however, not outside the range of values reported for some other asymmetric oxygen-containing compounds. No literature values were found for comparison, except for a recently published melting temperature of 255 K measured using a “cold bath” without specifying any additional details on uncertainty or measurement procedure …”

Section: Resultsmentioning

confidence: 99%

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Thermodynamic Properties and Phase Equilibria of Dihydrolevoglucosenone and Its Mixtures with Hydrocarbons

Jeřábek,

Štejfa,

Klajmon

et al. 2023

J. Chem. Eng. Data

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Thermodynamic and computational study of a biomass-derived solvent dihydrolevoglucosenone (DLG) and its mixtures with hydrocarbons is presented in this work. Density and dynamic viscosity of DLG were measured within the temperature range of 293.15−353.15 K. Phase behavior of DLG above 183 K was analyzed using heat-flux differential scanning calorimetry, providing data on its melting temperature and enthalpy of fusion. Heat capacity of DLG was measured using a Tian-Calvet calorimeter at temperatures between 253 and 353 K. Two static apparatuses were utilized to measure the vapor pressure of DLG in the temperature range of 253−363 K. A thermodynamically consistent description was achieved by simultaneous correlation of experimental values of phase behavior, heat capacities, vapor pressures, and theoretical calculations. Liquid−liquid equilibria (LLE) data in four binary DLG and hydrocarbons (n-hexane, cyclohexane, n-decane, and ntetradecane) systems were determined using a combination of volumetric, cloud-point, and direct analytical methods. The obtained LLE data were employed to thermodynamically describe the binary mixtures using the nonrandom two-liquid (NRTL) equation and estimate critical points using the Extended-Scaling Law (ESL) equation. Furthermore, the pure-component data developed in this work were used to determine two new sets of parameters for DLG within the perturbed-chain statistical associating fluid theory (PC-SAFT) equation of state: one with and one without the explicit inclusion of the dipole moment of DLG in the model theory. In addition, one more set of parameters for DLG developed earlier by other authors was included. PC-SAFT with all three parameter sets was then examined in terms of its performance regarding the description of the LLE in the systems studied. Both correlations (with optimized k ij ) and pure predictions (k ij = 0) were considered and discussed. Interestingly, it appears that the better PC-SAFT with a particular parameter set for DLG performs for the properties of pure DLG, the worse are the results for the LLE in the DLG + hydrocarbon systems. For example, PC-SAFT with the nonpolar parameters for DLG provided more accurate results for pure DLG than its polar counterparts, while it quantitatively failed for the LLE.

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Section: Resultsmentioning

confidence: 99%

“…No literature values were found for comparison, except for a recently published melting temperature of 255 K measured using a "cold bath" without specifying any additional details on uncertainty or measurement procedure. 75…”

Section: Phase Behaviormentioning

confidence: 99%

Thermodynamic Properties and Phase Equilibria of Dihydrolevoglucosenone and Its Mixtures with Hydrocarbons

Jeřábek,

Štejfa,

Klajmon

et al. 2023

J. Chem. Eng. Data

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Xylose Acetals ‐ a New Class of Sustainable Solvents and Their Application in Enzymatic Polycondensation

Komarova,

Warne,

Pétremand

et al. 2024

ChemSusChem

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The use of organic solvents in academic research and industry applications is facing increasing regulatory pressure due to environmental and health concerns. Consequently, there is a growing demand for sustainable solvents, particularly in the enzymatic synthesis and processing of polyesters. Biocatalysts offer a sustainable method for producing these materials; however, achieving high molecular weights often necessitates use of solvents. In this work, we introduce a new class of alternative aprotic solvents with medium polarity produced directly from agricultural waste biomass in up to 83 mol% yield (on xylan basis). The new solvents have a largely unmodified xylose core and acetal functionality, yet they show no peroxide formation and provide reduced flammability risk. We also demonstrate their successful application in enzymatic polycondensation reactions with Candida antarctica lipase B (CaLB). In particular, the solvent dibutylxylose (DBX) outperformed the hazardous solvent diphenyl ether and facilitated polycondensation of the lignin‐derived diester pyridine‐2,4‐dicarboxylate, yielding polyesters with a Mn of >15 kDa. Computational modelling studies provided further insight into the molecular structure and dynamics of CaLB in the presence of new solvents. Lastly, up to 98 wt% of the new xylose acetals were successfully recovered and recycled, further contributing to the sustainability of the overall process.

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1,3-Dioxolane compounds (DOXs) as biobased reaction media

Abstract: Solvents constitute around 80 % of the total volume of chemicals used in a process, and contribute significantly to its environmental impact and hazard profile. Thus, there is a strong...

Cited by 2 publications

References 64 publications

Thermodynamic Properties and Phase Equilibria of Dihydrolevoglucosenone and Its Mixtures with Hydrocarbons

Thermodynamic Properties and Phase Equilibria of Dihydrolevoglucosenone and Its Mixtures with Hydrocarbons

Xylose Acetals ‐ a New Class of Sustainable Solvents and Their Application in Enzymatic Polycondensation

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