1,4-Pentanediol: Vapor Pressure, Density, Viscosity, Refractive Index, and Its Isobaric Vapor–Liquid Equilibrium with 2-Methyltetrahydrofurane

Abstract

1,4-Pentanediol (1,4-PDO) can be utilized as a renewable building block for the polymer industry. 2-Methyltetrahydrofuran (2-MeTHF) can be utilized as a renewable fuel additive, a component of P-fuel, and an alternative solvent for synthesis and catalysis. Both 1,4-PDO and 2-MeTHF can be synthesized from either levulinic acid or γ-valerolactone, resulting in their mixture. In this sense, the corresponding vapor–liquid equilibrium data of these compounds is important to model and design related separation processes such as vacuum distillation. First, the temperature-dependent vapor pressure of 1,4-PDO was determined in the range of 413.1–496.5 K and correlated by three-parameter Antoine and Clark–Glew equations. The temperature-dependent viscosity and density as well as refractive index were measured in the temperature ranges of 293.1–363.1 and 291.1–333.1 K, respectively. The isobaric vapor–liquid equilibrium (VLE) of 1,4-PDO and 2-MeTHF was determined at atmospheric (p = 101.3 kPa) and reduced (p = 50.7 kPa) pressures. The experimental data were evaluated by the L–W thermodynamic consistency test developed by Wisniak and correlated with Wilson, NRTL, and UNIQUAC activity coefficient models, which were analyzed by the Van Ness test. The applied models were found suitable for representing the VLE data.

Isobaric Vapor–Liquid Equilibria for Binary Mixtures of Biomass-Derived Gamma-Valerolactone + 1,4-Pentanediol and 1,2-Ethanediol

“…The obtained Antoine parameters are as follows: A = 6.4314 ± 0.0291, B = 1888.0173 ± 22.8921, and C = −53.9478 ± 2.3781 with a root-mean-square-deviation (RMSD, eq ) of 0.04 and Δ p % value of 0.08. The Antoine constants of 1,4 PDO were determined in our previous study, and those for 1,2-EDO were obtained from the PURE37 database of Aspen Plus Software. log false( p 0 / normalk normalP normala false) = A − B C + T / K Δ p % = 100 N ∑ i = 1 N false| p i , normalm normale normala normals 0 − p i , normalc normala normall normalc 0 false| p i , m e a s 0 R M S D = 1 N − m ∑ i = 1 N false( p i , normalm normale normala normals 0 − p i , normalc normala normall <...…”

“…The measurements of vapor pressure and the vapor–liquid equilibria were performed by the use of a modified Gillespie still (Figure 1 in ref ). The experimental setup and procedure, which has routinely been used in our previous studies, − was verified by the successful reproduction of vapor–liquid equilibrium of a ethylene glycol–ethanol binary mixture . The apparatus and the description and details of VLE measurements were given in our previous paper …”

“…In spite of the development of numerous catalyst systems for the production of 1,4-PDO, according to the best of our knowledge, only one study was focused on its appropriate isolation technique, for example distillation, which could have industrial significance for its large-scale production. While there are available VLE data for GVL’s binary mixtures such as GVL–H 2 O, GVL–linear C 1 –C 3 alcohols, GVL–toluene, GVL–furanes, , and GVL–HCOOH, only a very recent work reported VLE data for 1,4-PDO with 2-MeTHF . In order to investigate and design efficient distillation unit(s) for its separation, the determination of reliable experimental VLE data and binary interaction parameters (BIPs) of 1,4-PDO and GVL is highly desired.…”

“…While there are available VLE data for GVL's binary mixtures such as GVL− H 2 O, 32 GVL−linear C 1 −C 3 alcohols, 33 GVL−toluene, 34 GVL− furanes, 35,36 and GVL−HCOOH, 37 only a very recent work reported VLE data for 1,4-PDO with 2-MeTHF. 31 In order to investigate and design efficient distillation unit(s) for its separation, the determination of reliable experimental VLE data and binary interaction parameters (BIPs) of 1,4-PDO and GVL is highly desired. In addition, the phase behavior of GVL with other diols could also be interesting for its separation and purification, as its use as industrial solvent was also proposed.…”

“…1,4-Pentanediol was prepared according to the published method. 31 The CAS numbers, purification method, purity of components, and refractive indices of GVL, 1,4-PDO, and 1,2-EDO are summarized in Table 1.…”