Vapor Pressures, Enthalpies of Vaporization, and Critical Parameters of a Series of Linear Aliphatic Dimethyl Esters of Dicarboxylic AcidsClick to copy article linkArticle link copied!
- Sergey P. Verevkin
- Svetlana A. Kozlova
- Vladimir N. Emel'yanenko
- Eugene D. Nikitin
- Alexander P. Popov
- Eugen L. Krasnykh
Abstract
Vapor pressures and the molar enthalpies of vaporization of the linear aliphatic dimethyl esters of dicarboxylic acids CH3-CO2-(CH2)n-CO2-CH3 with n = (0 to 8) have been determined by the transpiration method. A linear correlation of enthalpies of vaporization (at T = 298.15 K) of the esters studied with the number n and with the Kovat's indices and has been found. The critical temperatures and pressures of the esters with n = (0 to 6) and n = 8 have been measured by the pulse-heating method with the residence times ranging from (0.03 to 1) ms. Experimental data on the critical properties are compared with the estimations by group contribution methods by Constantinou and Gani and by Marrero and Gani. Both methods considerably underestimate the critical temperatures of the esters studied; however, the method by Marrero and Gani provides the prediction of the critical pressures of the esters with an average absolute error approximately equal to the uncertainty of the measurements.
*
Address correspondence concerning vapor pressures to this author. E-mail: [email protected]. Phone: +49-381-498-6508. Fax: +49-381-498-6502. Address correspondence concerning critical properties to this author. E-mail: [email protected]. Phone: +7-343-2678810. Fax: +7-343-2678800.
Cited By
This article is cited by 34 publications.
- Svetlana V. Portnova, Natalia S. Kuzmina, Yulia F. Yamshchikova, Eugene L. Krasnykh. Density and Viscosity of Glycolic, Lactic, and Malic Acid Esters. Journal of Chemical & Engineering Data 2022, 67
(9)
, 2323-2332. https://doi.org/10.1021/acs.jced.2c00267
- Jia Qiu, Di Xie, Yatai Li, Yuekun Qu, Ying Liu, Tong Zhu, Yingjun Liu. Dibasic Esters Observed as Potential Emerging Indoor Air Pollutants in New Apartments in Beijing, China. Environmental Science & Technology Letters 2021, 8
(6)
, 445-450. https://doi.org/10.1021/acs.estlett.1c00198
- Xingchuan Yang, Huanxin Li, Chunmei Cao, Zongpeng Zou, Li Xu, Guoji Liu. Isobaric Vapor–Liquid Equilibrium for the Binary System of Dimethyl Adipate and 1,6-Hexanediol at 10, 20, and 99 kPa. Journal of Chemical & Engineering Data 2019, 64
(10)
, 4256-4263. https://doi.org/10.1021/acs.jced.9b00306
- A. B. Pereiro, A. Rodriguez, M. Blesic, K. Shimizu, J. N. Canongia Lopes, and L. P. N. Rebelo . Mixtures of Pyridine and Nicotine with Pyridinium-Based Ionic Liquids. Journal of Chemical & Engineering Data 2011, 56
(12)
, 4356-4363. https://doi.org/10.1021/je2001446
- Svetlana V. Lipp and Eugenii L. Krasnykh , Sergey P. Verevkin . Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids. Journal of Chemical & Engineering Data 2011, 56
(4)
, 800-810. https://doi.org/10.1021/je100231g
- Sergey P. Verevkin, Vladimir N. Emel’yanenko, Alexey V. Toktonov and Anna S. Leolko, Julia Duwensee and Udo Kragl, Stefan M. Sarge. Thermochemical and Ab Initio Studies of Biodiesel Fuel Surrogates: 1,2,3-Propanetriol Triacetate, 1,2-Ethanediol Diacetate, and 1,2-Ethanediol Monoacetate. Industrial & Engineering Chemistry Research 2009, 48
(15)
, 7388-7399. https://doi.org/10.1021/ie900308u
- Dharmana Chinnarao, Ch V. Padmarao, Ch Beena, M. Srilatha, M.V.V. Ramanjaneyulu, Praveen Choppara, N. Murali, B. Venkateswara Rao. Acoustic, excess thermodynamical, molecular interaction and anti-microbial activity studies on binary liquid mixtures of geranyl acetate and benzyl benzoate in the temperature range of 303.15K–318.15K. Journal of the Indian Chemical Society 2023, 100
(5)
, 100969. https://doi.org/10.1016/j.jics.2023.100969
- E. Kiumarsian, S.M. Hosseini, M.M. Alavianmehr. Modeling thermophysical properties of several liquid adipates. Journal of Molecular Liquids 2022, 367 , 120350. https://doi.org/10.1016/j.molliq.2022.120350
- J. Udayaseelan, M. Aravinthraj, F. Liakath Ali Khan, C.P. Devipriya. The non-covalent interaction studies of o-nitrophenol and methyl acetate in benzene: By ultrasonics, FTIR and DFT methods. Materials Today: Proceedings 2021, 47 , 4527-4532. https://doi.org/10.1016/j.matpr.2021.05.420
- Chunli Zhi, Yang Tang, Jinru Wan, Xingming Liu, Honglin Chen, Xunqiu Wang. Determination and correlation of ternary isobaric vapour-liquid equilibrium data of (dimethyl succinate + dimethyl glutarate + dimethyl adipate) at 2, 5 and 8 kPa. The Journal of Chemical Thermodynamics 2020, 143 , 106047. https://doi.org/10.1016/j.jct.2019.106047
- Pinar Cay-Durgun, Sofia C. Herrera, Mary Laura Lind. Filler materials to prevent polymer intrusion into mesoporous substrates during thin film formation. Microporous and Mesoporous Materials 2020, 296 , 109956. https://doi.org/10.1016/j.micromeso.2019.109956
- Aizat A. Samatov, Ruslan N. Nagrimanov, Evgeniy A. Miroshnichenko, Boris N. Solomonov. Vaporization/sublimation enthalpies of mono- and dimethyl-esters estimated by solution calorimetry method. Thermochimica Acta 2020, 685 , 178529. https://doi.org/10.1016/j.tca.2020.178529
- Zeyu Zhang, Xianyang Meng, Ke Zhang, Jiangtao Wu. Viscosity Measurements of Dialkyl Adipates in the Temperature Range of (283 to 363) K and up to 40 MPa. International Journal of Thermophysics 2019, 40
(12)
https://doi.org/10.1007/s10765-019-2573-6
- R. Rajalakshmi, S. Ravikumar, Rekha Gaba, V. Pandiyan. Thermodynamic properties and IR studies of binary mixtures of benzyl amine with alkyl esters at different temperatures. Chemical Data Collections 2019, 24 , 100278. https://doi.org/10.1016/j.cdc.2019.100278
- Honglin Chen, Lei Zhang, Yulan Huang, Jingjing Lu, Zhijian Zhao, Xunqiu Wang. Isobaric vapor–liquid equilibrium of three binary systems containing dimethyl succinate, dimethyl glutarate and dimethyl adipate at 2, 5.2 and 8.3 kPa. The Journal of Chemical Thermodynamics 2019, 133 , 100-110. https://doi.org/10.1016/j.jct.2019.02.006
- Mariana Fortunatti Montoya, Francisco A. Sánchez, Selva Pereda. Equilibrium in Pressurized Systems (Sub and Supercritical). 2019, 385-418. https://doi.org/10.1016/B978-0-12-811556-5.00009-0
- Mariana Fortunatti Montoya, Francisco A. Sánchez, Pablo E. Hegel, Selva Pereda. Phase equilibrium engineering of glycerol acetates fractionation with pressurized CO2. The Journal of Supercritical Fluids 2018, 132 , 51-64. https://doi.org/10.1016/j.supflu.2017.02.026
- Eugene D. Nikitin, Alexander P. Popov. Vapor-liquid critical temperatures and pressures of dicarboxylic acid diethyl esters. The Journal of Chemical Thermodynamics 2018, 116 , 130-133. https://doi.org/10.1016/j.jct.2017.09.004
- P. Bhanuprakash, N.V.V. Jyothi, C. Narasimharao, M. Raveendra, K. Sivakumar. Elucidation of molecular interactions in the mixtures of benzylalcohol with (C 2 –C 4 ) alkylacetates through volumetric, ultrasonic, theoretical and ATR-FTIR spectroscopic studies at T = (298.15, 303.15, 308.15 and 313.15) K. Journal of Molecular Liquids 2017, 234 , 49-63. https://doi.org/10.1016/j.molliq.2017.03.056
- William Acree, James S. Chickos. Phase Transition Enthalpy Measurements of Organic and Organometallic Compounds and Ionic Liquids. Sublimation, Vaporization, and Fusion Enthalpies from 1880 to 2015. Part 2. C11–C192. Journal of Physical and Chemical Reference Data 2017, 46
(1)
https://doi.org/10.1063/1.4970519
- William Acree, James S. Chickos. Phase Transition Enthalpy Measurements of Organic and Organometallic Compounds. Sublimation, Vaporization and Fusion Enthalpies From 1880 to 2015. Part 1. C
1
− C
10. Journal of Physical and Chemical Reference Data 2016, 45
(3)
, 033101. https://doi.org/10.1063/1.4948363
- E. L. Krasnykh, S. V. Portnova. Prediction of enthalpies of vaporization based on modified Randič indices. Esters. Journal of Structural Chemistry 2016, 57
(3)
, 437-445. https://doi.org/10.1134/S0022476616030033
- S. V. Portnova, E. L. Krasnykh, S. V. Levanova. Temperature dependences of saturated vapor pressure and the enthalpy of vaporization of n-pentyl esters of dicarboxylic acids. Russian Journal of Physical Chemistry A 2016, 90
(5)
, 990-993. https://doi.org/10.1134/S0036024416050253
- Eugene D. Nikitin, Alexander P. Popov. Critical temperatures and pressures of some dicarboxylic acid diethyl esters. Fluid Phase Equilibria 2016, 412 , 57-61. https://doi.org/10.1016/j.fluid.2015.12.031
- João C.F. Diogo, Helena M.N.T. Avelino, Fernando J.P. Caetano, João M.N.A. Fareleira. Density measurements of compressed dipropyl, dibutyl, bis(2-ethylhexyl) adipates from (293 to 373K) at pressures up to about 68MPa. Fluid Phase Equilibria 2014, 374 , 9-19. https://doi.org/10.1016/j.fluid.2014.04.018
- Marie Spiandore, Anne Piram, Alexandre Lacoste, Denis Josse, Pierre Doumenq. Hair analysis as a useful procedure for detection of vapour exposure to chemical warfare agents: simulation of sulphur mustard with methyl salicylate. Drug Testing and Analysis 2014, 6
(S1)
, 67-73. https://doi.org/10.1002/dta.1659
- João C.F. Diogo, Fernando J.P. Caetano, João M.N.A. Fareleira. Viscosity and density measurements of compressed liquid dimethyl adipate using oscillating body techniques. Fluid Phase Equilibria 2014, 367 , 85-94. https://doi.org/10.1016/j.fluid.2014.01.030
- E. L. Krasnykh. Prediction of vaporization enthalpies based on modified Randič indices. Aldehydes and ketones. Journal of Structural Chemistry 2013, 54
(4)
, 792-796. https://doi.org/10.1134/S0022476613040203
- Artemiy A. Samarov, Alyanus G. Nazmutdinov, Sergey P. Verevkin. Vapour pressures and enthalpies of vaporization of aliphatic esters. Fluid Phase Equilibria 2012, 334 , 70-75. https://doi.org/10.1016/j.fluid.2012.08.003
- Alexei K. Baev. Specific Intermolecular Interactions and H-bonds in Aldehydes and Esters. 2012, 277-324. https://doi.org/10.1007/978-3-642-21622-0_6
- Svetlana V. Portnova, Eugen L. Krasnykh, Sergey P. Verevkin. Vapour pressure and enthalpy of vaporization of di-iso-propyl and di-tert-butyl esters of dicarboxylic acids. Fluid Phase Equilibria 2011, 309
(2)
, 114-120. https://doi.org/10.1016/j.fluid.2011.07.007
- Vasiliy A. Pozdeev, Sergey P. Verevkin. Vapor pressure and enthalpy of vaporization of linear aliphatic alkanediamines. The Journal of Chemical Thermodynamics 2011, 29 https://doi.org/10.1016/j.jct.2011.06.008
- José M.S. Fonseca, Ralf Dohrn, Stephanie Peper. High-pressure fluid-phase equilibria: Experimental methods and systems investigated (2005–2008). Fluid Phase Equilibria 2011, 300
(1-2)
, 1-69. https://doi.org/10.1016/j.fluid.2010.09.017
- A. S. Maslakova, E. L. Krasnykh, S. V. Levanova. Saturated vapor pressures and enthalpies of evaporation of esters of glycerol and lower carboxylic acids. Russian Journal of Physical Chemistry A 2010, 84
(2)
, 163-168. https://doi.org/10.1134/S0036024410020032
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.