Vapor-liquid equilibria, density and sound velocity measurements of (water or methanol or ethanol + 1,3-propanediol) binary systems at different temperatures
Graphical abstract
Introduction
Nowadays, it is necessary to make efforts to find replacements of fossil fuels due to the diminishing of petroleum reserves and increasing of the greenhouse gas emissions. For this reason, the interest has been taken in the conversion of biomass resources into biofuels. Biodiesel is one of the promising alternative fuels to meet these problems. Biodiesel, also known as fatty acid methyl or ethyl ester, is commonly derived from the transesterification or esterification of biological feedstocks with alcohol (ethanol or methanol).From the transesterification process; glycerol is the major byproduct, approximately 10 wt.% of the total product [1], [2]. With this enormous generation of the waste stream, it is very important to explore some utilizing glycerol. One of this utilization of glycerol is the microbial conversion into1,3-propanediol (1,3-PDO) [3]. The world production of 1,3-PDO is growing rapidly due to the increasing market demand of its derivatives into highly valuable products. It is achieving over 100 million pounds per year [4]. 1,3-PDO is a colorless, odorless, viscous liquid and have properties such as non-flammable, low toxicity, miscible with water, alcohol and ethers. As a biofunctional organic molecule, 1,3-PDO has several promising properties for many synthetic reactions, such as monomer for polycondensations to produce polyesters [5]. 1,3-PDO can be also formulated into laminates, solvents, adhesives, resins, detergents, cosmetics, deodorants and other uses [6]. 1,3-PDO has a multitude of other applications as shown in Fig. 1.
1,3-PDO is mainly produced from petroleum derivatives such as ethylene oxide and acrolein through chemical processes [7]. The fermentation route to produce 1,3-PDO from a glucose feedstock is estimated to be price competitive with the petrochemical methods. The bioconversion method of glycerol into the 1,3-PDO was demonstrated using several microbial cultures such as klebsiella pneumonia [8], citrobacterfreundii [9], enterobacteragglomerans [10], clostridium butyricum [11], [12], and lactobacillus reuteri [13].
Several methods have been adopted for the separation of 1,3-PDO from the mixture containing water and alcohols. Some of these include liquid–liquid extraction [14], reactive–extractive process [15], aqueous two-phase extraction [16], and molecular distillation [17]. To carry out the recovery of 1,3-PDO, the knowledge of thermophysical properties including the density and sound velocity of water, alcohol and 1,3-PDO presents in the downstream are required. These could also provide important information on the purity of the samples as well as intermolecular interaction between the mixtures and allows developing new predictive/correlative model.
To overcome the lack of information on thermodynamic and thermophysical properties for {water or alcohol (1) + 1,3-PDO (2)} systems, the experimental data, such as vapor-liquid equilibrium, volumetric and acoustic properties for these binary systems were presented by several authors [18], [19], [20], [21], [22], [23], [24], [25], [26], [29]. Sanz et al.[18] have reported VLE data for {water (1) + 1,3-PDO (2)} at 30 kPa. Lai et al. [19] have also studied the isobaric VLE of {water (1) + 1,3-PDO (2)} at 101.3KPa and at temperature interval of (373–487) K. The vapor liquid equilibria for {water (1) + 1,3-PDO (2)} have been also investigated by Mun and Lee [20] in terms of pressure but no comparison was possible. Parsons et al. [21] have reported VLE data for {water (1) + 1,3-PDO (2)} at 25 °C. No data have been found for {methanol (1) + 1,3-PDO (2)} system. The excess molar volume for {water (1) + 1,3-PDO (2)} system were performed by Zemánková et al. [22], Czechowski et al. [26] and Checoni et al. [27] at temperatures between (283.15 and 313.15) K, The molecular interaction of alkanediols in methanol have been explained by Piekarski et al. and Orge et al. [28], [29].
In this work, VLE data for the binary systems {water or methanol (1) + 1,3-PDO (2)} are reported. All measurements were performed at atmospheric pressure and at (273.15–343.15 or 363.15) K over the whole range of composition. In addition to this, the measurements of densities and sound velocity are also presented for {water or methanol or ethanol (1) + 1,3-PDO (2)} at (283.15–313.15) K.
Section snippets
Materials
1,3-PDO, methanol and ethanol were high purity grade reagents with greater than 0.99 (mole fraction). Freshly degassed triply distilled water (specific conductance >10−6 S cm−1) has been used for the preparation of mixtures. Table 1, reports the provenance, CAS number, and the purities stated by the suppliers and those obtained by Gas Chromatography, together with the densities (ρ) and the refractive indexes (nD), of pure liquids at 293.15 K. The mass percent water content was determined using a
Pure components
For pure methanol and 1,3-PDO, vapor pressure data available in the literature [54], [55] at investigated temperatures has been used for correlation. Only the vapor pressure of water was determined experimentally within the temperature range of (273.16–363.19) K. The data was fitted to the Antoine Eq. (1):Where P is the vapor pressure, T is the temperature, A, B, and Care constants.
The objective function Q was the sum of the squared relative deviations in pressure
Conclusion
This paper reports vapor-liquid equilibria data for {water or methanol (1) + 1,3- PDO (2)} systems using a static device over the range of temperature from (273.15–363.15) K. The aqueous solution of 1,3-PDO exhibits positive and negative (S shape) values in GE calculated from the vapor pressure values over the temperature range (273.15 ˂ T ˂ 363.15) K. The 1,3-PDO in methanol exhibits negative deviations in GE within the same range of temperature. The results of the binary mixtures were correlated
Acknowledgments
The research was supported by Joint Research Grant under the SA/Algeria (NRF/DGRSDT) Agreement on Cooperation in Science and Technology “Measurement of Thermodynamic and Thermo-physical Data for Fluorinated Organics and Petrochemicals”. Dr. I. Bahadur acknowledge funding from North-West University and Department of Science and Technology and the National Research Foundation (DST/NRF) South Africa grant funded (Grant UID: 92333) This work has been done in the framework of the international
References (72)
- et al.
Critical review on the current scenario and significance of crude glycerol resulting from biodiesel industry towards more sustainable renewable energy industry
Renew. Sustain. Energy Rev.
(2012) - et al.
Glycerol as a by-product of biodiesel production in Brazil: Alternatives for the use of unrefined glycerol
Renew. Energy
(2012) - et al.
Advances in biotechnological production of 1,3-propanediol
Biochem. Eng. J.
(2012) - et al.
Biosynthesis of 1,3-propanediol from glycerol with lactobacillus reuteri: effect of operating variables
J. Biosci. Bioeng.
(2014) - et al.
Extraction of 1,3-propanediol from glycerol-based fermentation broths with methanol/phosphate aqueous two-phase system
Process Biochem.
(2011) - et al.
Isobaric (vapor + liquid) equilibria for the ternary system of (ethanol + water + 1,3-propanediol) and three constituent binary systems at P = 101.3 kPa
J. Chem. Thermodyn.
(2014) - et al.
Excess volumes and excess heat capacities for alkanediol + water systems in the temperature interval (283.15–313.15) K
Fluid Phase Equilib.
(2013) - et al.
Measurement and modeling of volumetric properties and sound speeds of several mixtures of alcohol liquids containing 1-propanol and 2-propanol at T = (298. 15-323.15) K and ambient pressure
Fluid Phase Equilib.
(2014) Experimental study of the excess molar volume of ternary mixtures containing {water + (1,2-propanediol, or 1,3-propanediol, or 1,2-butanediol, or 1,3-butanediol, or 1,4-butanediol, or 2,3-butanediol) + electrolytes} at a temperature of 298.15 K and atmospheric pressure
J. Chem. Thermodyn.
(2010)- et al.
Molecular interactions of alkanediols in methanol and in water: density and heat capacity measurements
J. Mol. Liq.
(2005)
Volume properties of liquid mixture of water + glycerol over the temperature range from 278.15 to 348.15 K at atmospheric pressure
Thermochim. Acta
Experimental (vapour + liquid) equilibrium data of (methanol + water), (water + glycerol) and (methanol + glycerol) systems at atmospheric and sub-atmospheric pressures
J. Chem.Thermodyn.
Densities refractive indices and excess molar volumes for binary mixtures of protic ionic liquids with methanol at T = 293.15 to 313.15 K
J. Mol. Liq.
Experimental vapor pressures of alkyl and aryl sulfides Prediction by a group contribution method
Fluid Phase Equilib.
Density speed of sound and refractive index measurements for the binary systems (butanoic acid + propanoic acid or 2-methyl-propanoic acid) at T = (293. 15-313.15) K
J. Chem. Thermodyn.
Volumetric properties of binary mixtures of acetonitrile and alcohols at different temperatures and atmospheric pressure
J. Mol. Liq.
Influence of alkyl group and temperature on thermo-physical properties of carboxylic acid and their binary mixtures
Thermochim. Acta
Advanced calibration adjustment, and operation of a density and sound speed analyzer
J. Chem.Thermodyn.
Densities, excess molar volumes, speeds of sound and isothermal compressibilities for {2-(2-hexyloxyethoxy)ethanol + n-alkanol} systems at temperatures between (288.15 and 308.15) K
J. Chem. Thermodyn.
Speed of sound measurements of liquid C1–C4 alkanols
J. Chem. Thermodyn.
Speed of sound measurements in mixtures of H2O and D2O
J. Chem. Thermodyn.
Thermodynamic properties of organic oxygen compounds XXV. Vapour pressures and normal boiling temperatures of aliphatic alcohols
J. Chem. Thermodyn.
Ultrasonic speeds and isentropic compressibilities for (decan-1-ol + n-alkane) at 298.15 K
J. Chem.Thermodyn.
Microbial conversion of glycerol to 1,3-propanediol: recent progress. Fuels and chemicals from biomass
Am. Chem. Soc.
Synthetic methods for the preparation of 1,3-propanediol
Clean
Tools and applications of biochemical engineering science
Adv. Biochem. Eng. Biotechnol.
New diol processes: 1,3-propanediol and 1,4-butanediol
Appl. Catal. A: Gen.
Microbial fedbatch production of 1,3-propanediol by Klebsiella pneumoniae under microaerobic conditions
Appl. Microbiol. Biotechnol.
Fermentation of glycerol to 1,3-propanediol in continuous cultures of Citrobacter freundii
Appl. Microbiol. Biotechnol.
Glycerol fermentation of 1,3-propanediol producing microorganism: Enterobacter. Agglomerans
Appl. Microbiol. Biotechnol.
Glycerol dehydratase activity: the limiting step for 1,3-ropanediol production by Clostridium butyricum
Lett. Appl. Microbiol.
Glycerol fermentation to 1,3-propanediol by Clostridium butyricum: measurement of product inhibition by use of a pH-auxostat
Appl. Microbiol. Biotechnol.
Evaluation of liquid extraction potentials for downstream separation of 1,3-propanediol
J. Technol.
Study on reactive extraction kinetics of 1,3-propanediol in dilute aqueous solutions
Sep. Sci. Technol.
Studies on purification of 1,3-propanediol by molecular distillation
Biotechnol. Biopro. Eng.
Vapor liquid equilibria of binary and ternary systems with water, 1,3-propanediol, and glycerol
J. Chem. Eng. Data
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2020, Journal of Chemical ThermodynamicsCitation Excerpt :The minima are located at xi ≈ 0.4. Considering only mixtures of ethanol with compounds with alcohol function, this behavior has been also reported for mixtures of ethanol with diols [28–31] or glycerol [32] or glycols or glycol derivatives [17,33]. Negative values of excess molar volume have been also obtained when compounds similar to carvacrol such as cresols (methylphenols) have been mixed with alkanols [34–37].