Thermodynamic properties of solubility of 2-methyl-5-arylfuran-3-carboxylic acids in organic solvents

2017;
: pp. 397–404
Received: November 22, 2016
Revised: December 15, 2016
Accepted: January 27, 2017
1
Lviv Polytechnic National University
2
Lviv Polytechnic National University
3
Ivan Franko National University of Lviv
4
Institute of Macromolecular Chemistry AS CR
5
Lviv Polytechnic National University
6
Ivan Franko National University of Lviv

The temperature dependencies of both acids solubility in acetonitrile, dimethylketone, isopropanol, ethylacetate and benzene were investigated. The results were represented by Shredder’s equation according to which enthalpies, entropies and Gibbs energy of solubility at 298 K were determined. Fusion heats of the acids were determined using differential thermal analysis. In accordance with obtained values the enthalpies, entropies and Gibbs energy of mixing were calculated. The compensating effect of mixing was observed for al solvents with carboxy group.

[1] Fürstner A., Castanet A., Radkowski K., Lehmann C.: J. Org. Chem., 2003, 68, 1521. https://doi.org/10.1021/jo026686q

[2] Holla B., Akberali P., Shivananda M.: Farmaco, 2000, 55, 256. https://doi.org/10.1016/S0014-827X(00)00030-6

[3] Williams D., Lee M.-R., Song Y.-A. et al.: J. Am. Chem. Soc., 2007, 129, 9258. https://doi.org/10.1021/ja072817z

[4] Obushak N., Gorak Yu., Matiichuk V., Lytvyn R.: Russ. J. Org. Chem., 2008, 44, 1689. https://doi.org/10.1134/S1070428008110213

[5] Obushak N., Gorak Yu., Matiichuk V., Lytvyn R.: Russ. J. Org. Chem., 2009, 45, 541. https://doi.org/10.1134/S1070428009090103

[6] Obushak N., Lesyuk A., Gorak Yu., Matiichuk V.: Russ. J. Org. Chem., 2009, 45, 1375. https://doi.org/10.1134/S1070428009090103

[7] Obushak N., Lesyuk A., Ganushchak N. et al.: J. Org. Chem. USSR (Engl. Transl.), 1986, 22, 2093.

[8] Obushak N., Ganushchak N., Lesyuk A. et al.: J. Org. Chem. USSR (Engl. Transl.), 1990, 26, 748.

[9] Zhu J., Bienayme H. (Eds.): Multicomponent Reactions. Wiley-VCH, Weinheim 2005.

[10] Sobechko I., Van-Chin-Syan Yu., Gorak Yu. et al.: Rus. J. Phys. Chem., 2015, 89, 919. https://doi.org/10.1134/S003602441506028X

[11] Sobechko I., Gorak Yu., Van-Chin-Syan Yu. et al.: Izv. Vys. Ucheb. Zaved., 2015, 58, 45.

[12] Sobechko I., Prokop R., Gorak Yu. et al.: Voprosy Khimii i Khim. Techn., 2013, 4, 12.

[13] Sobechko I.: Voprosy Khimii i Khim. Techn., 2014, 5-6, 48.

[14] Serheyev V.: Chem. Chem. Technol., 2012, 6, 15.

[15] Serheyev V.: Chem. Chem. Technol., 2015, 9, 1.

[16] Serheyev V.: Rus. J. Phys. Chem., 2016, 90, 575. https://doi.org/10.1134/S0036024416030274

[17] Han S., Meng L., Du C. et al.: J. Chem. Thermodyn., 2017, 97, 17. https://doi.org/10.1016/j.jct.2015.11.025

[18] Li X., Du C., Cong Y., Zhao H.: J. Chem. Thermodyn., 2017, 104, 189. https://doi.org/10.1016/j.jct.2016.09.033

[19] Chickos J., Acree W. Jr.: J. Phys. Chem. Ref. Data, 2003, 32, 519. https://doi.org/10.1063/1.1529214

[20] http://webbook.nist.gov (March 18th, 2015)

[21] Vasil’ev I., Petrov V.: Thermodynamicheskie Svoistva Kislorod-soderzhashih Organicheskih Veshestv. Khimiya, Leningrad 1984.