Liquid–liquid equilibria for systems of water + methanol + methyl anthranilate at several temperatures
Highlights
► We measure LLE data for two systems including methyl anthranilate. ► We determine the reliability of experimental tie-line data through Bachman plots. ► We use the NRTL and UNIQUAC models to correlate the experimental data. ► The correlated results are in agreement with the experiment data. ► Average deviations from UNIQUAC are slightly smaller than those from NRTL.
Introduction
Methyl anthranilate (MA) is a very important chemical intermediate used as an artificial flavor and scent in foods and cosmetics [1], [2], [3], [4]. It is also a safe repellent against birds [5], [6], [7], [8] in agriculture and an intermediate in the saccharin production process. A number of procedures to produce methyl anthranilate have been reported [4], [9], [10]. The current practice is to use various acids as catalysts in the manufacture of methyl anthranilate either starting with isatoic anhydride and methanol or by the esterification of anthranilic acid with methanol [11]. Though most of MA could be separated from reaction mixtures by traditional separation methods, a part of methanol and MA still remain in the large quantity of waste water generated in the reaction. In recent years, MA has received increasing attention [12], [13]. It is known that LLE data are essential for the design of extraction equipment and/or for the calculation of the thermodynamic limit of a given separation. However, to our knowledge, with respect to the liquid–liquid equilibria data of the systems including MA, no literature data were available.
The purpose of this work is to measure LLE data for the systems of water + MA and water + methanol + MA under atmospheric pressure over the temperature range of 298.15–323.15 K. The experimental tie-line data were correlated to test consistency with the Bachman equations [14]. The NRTL [15] and UNIQUAC [16] models were used to correlate the experimental data for the systems studied in the research. The influence of methanol on the mutual solubility of MA and water was discussed. The experimental data provide a basis for influence of methanol on the mutual solubility of MA and water, which can serve for separation and processes design in industrial applications.
Section snippets
Materials
All chemicals were purchased from Tianjin Reagent Company (China), and distilled water was used. MA was dried using molecular sieves with a pore diameter of 0.5 nm and purified by vacuum distillation processing. The purity of the chemicals was examined using an Agilent 6820 gas chromatography. No impurity peaks were detected. Densities were measured with Anton Paar density meter (Model 4500). Refractive indexes were measured with an Abbe refractometer with an accuracy of ±5 × 10−4. The measured
Results and discussion
At liquid–liquid equilibrium, the composition of two phases can be determined from the following Eqs. (1), (2):Here and are the corresponding activity coefficients of component i in phases 1 and 2, and are the mole fractions of component i in the system in phases 1 and 2, respectively. The calculation procedure was detailed in Walas [21].
Bachman correlation Eq. (3) was used to ensure the quality of the obtained experimental tie-line data.
Conclusion
Liquid–liquid equilibrium data for the systems of water + MA and water + methanol + MA were measured under atmospheric pressure in the temperature range of 298.15–323.15 K. It was observed that the temperature has a slight influence on the size of the immiscibility region for the system of water + methanol + MA in the investigated temperature range. The LLE data were correlated using the NRTL and UNIQUAC activity coefficient models. Regarding the system water + methanol + MA, the UNIQUAC and NRTL models
References (24)
- et al.
Crop. Prot.
(1995) - et al.
J. Supercrit. Fluids
(2000) - et al.
J. Ind. Eng. Chem.
(2008) Perfum Flavor
(1997)- et al.
J. Agric. Food Chem.
(2002) - et al.
J. AOAC Int.
(2001) - et al.
J. Agric. Food Chem.
(2000) - C.S. Malhi, R. Kaur, Research Information, Burnham, Royaume-Uni, 2003, pp....
- et al.
J. Chem. Ecol.
(2000) J. Med. Entomol.
(2009)
Appl. Microbiol. Biotechnol.
J. Agric. Food Chem.
Cited by (5)
Thermochemical study of anthranilate derivatives: Effect of the size of the alkyl substituent
2021, Journal of Chemical ThermodynamicsCitation Excerpt :Thus, they can be found in several perfumes, essential oils and cosmetics [10]. Methyl anthranilate odor properties allows it to be used as bird and larvae repellent, but it can also be used as sunscreen agent as it possesses ultraviolet absorbent behaviour [11–13]. Butyl anthranilate can also be used as insect repellent [14,15].
Interaction parameter estimation in liquid-liquid phase equilibrium modeling using stochastic and hybrid algorithms
2012, Fluid Phase EquilibriaCitation Excerpt :In the fluid phase equilibria [1–4], the estimation of physical properties and the equilibrium prediction of chemical systems require accurate methods of optimisation dealing with parameter estimation [4–8].
Liquid-Liquid Equilibria for the Ternary System n-Butyl Acetate + Pyrocatechol + Water at Different Temperatures at 101.3 kPa
2016, Journal of Chemical and Engineering DataTernary and quaternary liquid-liquid equilibria for systems of water + methanol + methylanthranilate + toluene at different temperatures
2012, Journal of Chemical and Engineering Data