Isobaric vapor–liquid equilibrium of three binary systems containing dimethyl succinate, dimethyl glutarate and dimethyl adipate at 2, 5.2 and 8.3 kPa
Introduction
Dibasic esters containing dimethyl succinate (DMS), dimethyl glutarate (DMG), and dimethyl adipate (DMA), as important chemicals, have been widely used in various fields of human life and production. Detailed information are as follows: DMS not only can be used in the manufacture of synthetic perfumes and food additives, but also, as a chemical intermediate, can be used in the bioengineering field and the preparation of 1,4-Butylene glycol, γ-butyrolactone, tetrahydrofuran, itaconic acid, etc [1], [2]. DMG is an environment-friendly high-boiling point solvent, which can be used extensively in automotive coatings, paint remover, and electrochemical fields and the preparation of ketorolac, 1,5-pentanediol, copolyesters, etc [3], [4]. DMA is also enjoying widely application in the chemical industry, such as in the production of plasticizers, hexanediol, δ-decalactone, etc. Furthermore, high-purity dimethyl succinate and dimethyl glutarate can also be used for the preparation of inks in the production of carbon nanotube electrochemical sensors [5], [6], [7], [8]. As we all know, these three dimethyl esters of dicarboxylic acids are generally obtained from the esterification of corresponding dibasic acids (succinic acid, glutaric acid, adipic acid) with methanol under sulfuric acid or organic acid catalyst [9], [10]. However, due to the high price of succinic acid, glutaric acid and adipic acid, the corresponding dimethyl esters of dicarboxylic acids produced by this method has a higher cost. In addition to above method, using rectification technique to separate mixed dibasic esters (DBE) to get the DMS, DMG and DMA is also a feasible way, in which dibasic acid (DBA) is precursor for DBE production. According to information, DBA, as by-product, will be produced during the production of adipic acid, the approximate mass fraction of which is 25% for succinic acid, 60% for glutaric acid, and 15% for adipic acid [11]. What's more, at least 50,000 ton of DBA are produced every year in China, and the price of DBA is cheaper [12], [13]. So DBE can be directly obtained through the esterification reaction of DBA at a lower cost [14], [15], and afterwards DMS, DMG and DMA will be obtained by the distillation of DBE. Compared with the traditional method, this method producing these three dimethyl esters of dicarboxylic acids not only has low cost, but also improves the utilization value of the by-product DBA.
The physicochemical properties and vapor–liquid equilibrium data (VLE) of DMS, DMG and DMA provide essential information for designing their distillation separation process. To our knowledge, quite a few researches relevant to their physicochemical properties have been reported. Verevkin et al. [16] measured vapor pressures and the molar enthalpies of vaporization of the linear aliphatic dimethyl esters of dicarboxylic acids CH3-CO2-(CH2)n-CO2-CH3 (n = 0–8). And the critical temperatures and pressures of the esters with n = (0–6) and n = 8 have also been measured by the pulse-heating method. Comuñas et al. [17] researched the influence of the molecular structure on the volumetric properties and viscosities of dialkyl adipates and measured the density of DMA over 12 isotherms from 293.15 to 403.15 K and 15 isobars from 0.1 to 140 MPa. Diogo et al. [18] reported viscosity measurements of compressed liquid dimethyl adipate obtained with a vibrating wire sensor at temperatures from 293 to 358 K and up to 20 MPa. Puertas et al. [19] studied the enzymatic aminolysis of DMS and provided a new route for the enzymatic preparation of different kind of optically active heterocycles. In addition, in terms of phase equilibrium, Lee et al. [20] determined isothermal VLE data for methanol + DMA, methanol + DMG and DMG + glutaric acid at 353.15–453.15 K. Moreover, Ince et al. [21], [22] determined the liquid-liquid equilibrium (LLE) of water + ethanol (acetic acid) + DMG at 298.15,308.15, and 318.15 K. At the same time, Krbaslar et al. [23], [24] determined the LLE data of water + butyric acid (or propionic acid) + dibasic esters (DMS, DMG, DMA) at atmospheric pressure and 298.15 K, and the results concluded that the dibasic esters may serve as suitable solvents to extract butyric acid (or propionic acid) from its dilute aqueous solutions. In addition, Altuntepe et al. [25], [26], [27] researched the phase behavior of succinic acid and its esters, for example, isobaric VLE were measured for the binary systems acetonitrile/diethyl succinate, acetonitrile/dibutyl succinate, and tetrahydrofuran/dibutyl succinate at pressures of 10, 20 and 30 kPa. And they used perturbed-chain statistical associating fluid theory (PC-SAFT) to model phase equilibria and predict activity coefficients during the esterification process accurately.
All the works mentioned above provided significant information about the physicochemical properties of relevant esters. Nevertheless, there are rare reports about the VLE between DMS, DMG and DMA. Only Vlasov et al. [28] measured the VLE data of DMG and DMA at approximately 10 kPa, the temperature ranging from 414.6 K to 425.1 K. But they merely measured 10 data points, and the pressure fluctuated greatly during their measurement with narrow temperature range, none of the data being checked or regressed by any thermodynamic models. Therefore, the measurement results cannot provide accurate theoretical guidance for the distillation process. In order to study the VLE of these three esters completely and accurately, we measured isobaric vapor-liquid equilibrium data for DMS + DMG, DMS + DMA, and DMG + DMA systems at 2, 5.2 and 8.3 kPa. The Herington and Van Ness test were employed to check the thermodynamic consistency of the obtained data. Then NRTL, Wilson and UNIQUAC activity coefficient models were used to correlate the measured data, and the binary interaction parameters finally were obtained. This study provides basic data for the distillation design of DBE, making up for the lack of thermodynamic interaction parameters between these three esters.
Section snippets
Materials
The sources, purities and CAS registry numbers of the reagents used in our work are listed in Table 1. The three reagents were detected by gas chromatography (GC 7980, Techcomp LTD, China) with flame ionization detector (FID), and no impurities were detected. Thus, the materials were used without further dehydrating or purification.
Apparatus and procedure
The isobaric VLE data were measured using a commercial all-glass dynamic recirculation apparatus VLE110 (PILODIST GmbH laboratory & process technology, Germany)
Experimental results
Experimental isobaric VLE data for the systems (DMS + DMG), (DMS + DMA) and (DMG + DMA) at 2, 5.2, and 8.3 kPa are reported in Table 3, Table 4, Table 5, temperature ranging from 363.39 to 422.4 K.
And the boiling points of three pure components at 2, 5.2, and 8.3 kPa measured in this work have also been compared to earlier measurements in the other publications [16], [20], [42], [43], [44], [45], [46], [47], [48], [49], [50], [51], which are graphically displayed in Fig. 7, Fig. 8, Fig. 9. In
Conclusion
In this study, isobaric vapor–liquid equilibrium data of three binary systems (DMS + DMG), (DMS + DMA), (DMG + DMA) are determined at 2, 5.2 and 8.3 kPa, temperature ranging from 363.39 to 422.4 K. There is no azeotropic point to be found in the three binary systems, which behave almost ideally with slightly positive deviations. The thermodynamic consistency of the experimental data was checked by the Herington method and point to point method of Van Ness test. The test results indicated that
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