2 0 2019 wu wan 4 journal Original Wu, J.[Jiaxin] Wang, J.[Jian] Farajtabar, A.[Ali] Zhao, H.[Hongkun] J. Chem. Eng. Data 2019 2020-09-29 Solubility and Solution Thermodynamics of 2,6-Dichloro-4-nitroaniline in 12 Pure Solvents at Temperatures from 278.15 to 323.15 K Through the shake-flask method, the solubility of 2,6-dichloro-4-nitroaniline (DCNA) in twelve pure solvents of n-butanol, n-propanol, methanol, ethylene glycol (EG),ethanol, isopropanol, acetonitrile, cyclohexane, 1,4-dioxoane, ethyl acetate, water and N-methyl pyrrolidone (NMP) was achieved over the temperatures from 278.15 to 323.15 K at ambient pressure of p = 101.2 kPa. The mole fraction solubility of DCNA in above solvents increased as the temperature increased and ranked as: NMP greater than 1,4-dioxoane greater than ethyl acetate greater than acetonitrile greater than n-butanol greater than n-propanol greater than ethanol greater than EG greater than isopropanol greater than methanol greater than cyclohexane greater than water. The solvent-solvent and solvent-solute interactions upon the DCNA solubility were investigated using the linear solvation energy relationship on the basis of the solvent descriptors. The acquired solubility was correlated using the NRTL model, h equation, modified Apelblat equation and Wilson model. The obtained maximum relative average deviation and root-mean-square deviation through the four models were 6.53x10-2 and 13.73x10-4, respectively. In general, the relative average deviation values achieved through the modified Apelblat equation were lower than those with the other three equations for a certain solvent. In addition, the mixing properties, reduced excess enthalpy and activity coefficient under infinitesimal concentration were derived based on the Wilson model. 10.1021/acs.jced.9b00778 12 64 5869-5877 1 InChI=1S/C6H4Cl2N2O2/c7-4-1-3(10(11)12)2-5(8)6(4)9/h1-2H,9H2 BIXZHMJUSMUDOQ-UHFFFAOYSA-N 1-amino-2,6-dichloro-4-nitrobenzene 2,6-dichloro-4-nitroaniline 2,6-dichloro-4-nitrobenzenamine 2,6-dichloro-p-nitroaniline 4-nitro-2,6-dichloroaniline aniline, 2,6-dichloro-4-nitro- benzenamine, 2,6-dichloro-4-nitro- dichloran dicloran C6H4Cl2N2O2 1 Commercial source 1 95 3 Stated by supplier 2 Crystallization from solution 3 99.4 3 HPLC 2 InChI=1S/CH4O/c1-2/h2H,1H3 OKKJLVBELUTLKV-UHFFFAOYSA-N methanol methyl alcohol CH4O 1 Commercial source 1 99.5 3 Stated by supplier 3 InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3 LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol ethyl alcohol C2H6O 1 Commercial source 1 99.7 3 Stated by supplier 4 InChI=1S/C3H8O/c1-2-3-4/h4H,2-3H2,1H3 BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol 1-propanol n-propanol n-propyl alcohol C3H8O 1 Commercial source 1 99.4 3 Stated by supplier 5 InChI=1S/C3H8O/c1-3(2)4/h3-4H,1-2H3 KFZMGEQAYNKOFK-UHFFFAOYSA-N propan-2-ol 2-propanol isopropanol isopropyl alcohol sec-propyl alcohol C3H8O 1 Commercial source 1 99.7 3 Stated by supplier 6 InChI=1S/C2H6O2/c3-1-2-4/h3-4H,1-2H2 LYCAIKOWRPUZTN-UHFFFAOYSA-N 1,2-ethanediol 1,2-dihydroxyethane ethane-1,2-diol ethylene glycol C2H6O2 1 Commercial source 1 99.5 3 Stated by supplier 7 InChI=1S/C2H3N/c1-2-3/h1H3 WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile cyanomethane ethanenitrile ethanonitrile methanecarbonitrile methyl cyanide C2H3N 1 Commercial source 1 99.7 3 Stated by supplier 8 InChI=1S/C6H12/c1-2-4-6-5-3-1/h1-6H2 XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane C6H12 1 Commercial source 1 99.4 3 Stated by supplier 9 InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3 SECXISVLQFMRJM-UHFFFAOYSA-N N-methylpyrrolidone 1-methyl-2-pyrrolidinone 1-methyl-2-pyrrolidone 1-methyl-5-pyrrolidinone 1-methylazacyclopentan-2-one 1-methylpyrrolidin-2-one 1-methylpyrrolidone N-methyl-.alpha.-pyrrolidinone N-methyl-.alpha.-pyrrolidone N-methyl-.gamma.-butyrolactam N-methyl-2-pyrrolidinone N-methyl-2-pyrrolidone N-methylpyrrolidin-2-one NMP C5H9NO 1 Commercial source 1 99.5 3 Stated by supplier 10 InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3 LRHPLDYGYMQRHN-UHFFFAOYSA-N butan-1-ol 1-butanol n-butanol n-butyl alcohol C4H10O 1 Commercial source 1 99.6 3 Stated by supplier 11 InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3 XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate ethyl ethanoate C4H8O2 1 Commercial source 1 99.5 3 Stated by supplier 12 InChI=1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2 RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane 1,4-dioxacyclohexane dioxane p-dioxane tetrahydro-1,4-dioxin C4H8O2 1 Commercial source 1 99.5 3 Stated by supplier 13 InChI=1S/H2O/h1H2 XLYOFNOQVPJJNP-UHFFFAOYSA-N water H2O 1 Commercial source 1 99.9 3 Estimated by the compiler 1 1 1 13 1 Principal objective of the work EP EP 9/30/2019 1 Mole fraction Chromatography 1 Liquid Direct value, X 1 Data file compiler Propagation of evaluated standard uncertainties 95 Liquid Crystal 1 1 Pressure, kPa Liquid 101.2 4 1 Temperature, K Liquid 1 278.15 5 1 1.881e-06 4 1 1.17e-07 1 283.15 5 1 2.527e-06 4 1 1.57e-07 1 288.15 5 1 3.426e-06 4 1 2.13e-07 1 293.15 5 1 4.76e-06 4 1 2.96e-07 1 298.15 5 1 6.431e-06 4 1 3.99e-07 1 303.15 5 1 8.305e-06 4 1 5.15e-07 1 308.15 5 1 1.061e-05 4 1 6.6e-07 1 313.15 5 1 1.369e-05 4 1 8.5e-07 1 318.15 5 1 1.723e-05 4 1 1.07e-06 1 323.15 5 1 2.18e-05 4 1 1.35e-06 2 1 1 2 1 Principal objective of the work EP EP 9/30/2019 1 Mole fraction Chromatography 1 Liquid Direct value, X 1 Data file compiler Propagation of evaluated standard uncertainties 95 Liquid Crystal 1 1 Pressure, kPa Liquid 101.2 4 1 Temperature, K Liquid 1 278.15 5 1 0.0007054 4 1 4.38e-05 1 283.15 5 1 0.0008142 4 1 5.05e-05 1 288.15 5 1 0.0009867 4 1 6.12e-05 1 293.15 5 1 0.00121 4 1 7.5e-05 1 298.15 5 1 0.001498 4 1 9.3e-05 1 303.15 5 1 0.001818 4 1 0.000113 1 308.15 5 1 0.002237 4 1 0.000139 1 313.15 5 1 0.002675 4 1 0.000166 1 318.15 5 1 0.003139 4 1 0.000195 1 323.15 5 1 0.003772 4 1 0.000234 3 1 1 3 1 Principal objective of the work EP EP 9/30/2019 1 Mole fraction Chromatography 1 Liquid Direct value, X 1 Data file compiler Propagation of evaluated standard uncertainties 95 Liquid Crystal 1 1 Pressure, kPa Liquid 101.2 4 1 Temperature, K Liquid 1 278.15 5 1 0.0008791 4 1 5.45e-05 1 283.15 5 1 0.001018 4 1 6.3e-05 1 288.15 5 1 0.001232 4 1 7.6e-05 1 293.15 5 1 0.001487 4 1 9.2e-05 1 298.15 5 1 0.001831 4 1 0.000114 1 303.15 5 1 0.002221 4 1 0.000138 1 308.15 5 1 0.002677 4 1 0.000166 1 313.15 5 1 0.00325 4 1 0.000202 1 318.15 5 1 0.003839 4 1 0.000238 1 323.15 5 1 0.004552 4 1 0.000282 4 1 1 4 1 Principal objective of the work EP EP 9/30/2019 1 Mole fraction Chromatography 1 Liquid Direct value, X 1 Data file compiler Propagation of evaluated standard uncertainties 95 Liquid Crystal 1 1 Pressure, kPa Liquid 101.2 4 1 Temperature, K Liquid 1 278.15 5 1 0.001017 4 1 6.3e-05 1 283.15 5 1 0.001227 4 1 7.6e-05 1 288.15 5 1 0.001464 4 1 9.1e-05 1 293.15 5 1 0.001759 4 1 0.000109 1 298.15 5 1 0.002159 4 1 0.000134 1 303.15 5 1 0.002575 4 1 0.00016 1 308.15 5 1 0.003073 4 1 0.000191 1 313.15 5 1 0.003643 4 1 0.000226 1 318.15 5 1 0.004412 4 1 0.000274 1 323.15 5 1 0.005459 4 1 0.000339 5 1 1 5 1 Principal objective of the work EP EP 9/30/2019 1 Mole fraction Chromatography 1 Liquid Direct value, X 1 Data file compiler Propagation of evaluated standard uncertainties 95 Liquid Crystal 1 1 Pressure, kPa Liquid 101.2 4 1 Temperature, K Liquid 1 283.15 5 1 0.0009301 4 1 5.77e-05 1 288.15 5 1 0.001107 4 1 6.9e-05 1 293.15 5 1 0.001326 4 1 8.2e-05 1 298.15 5 1 0.001617 4 1 0.0001 1 303.15 5 1 0.001952 4 1 0.000121 1 308.15 5 1 0.00234 4 1 0.000145 1 313.15 5 1 0.002808 4 1 0.000174 1 318.15 5 1 0.003381 4 1 0.00021 1 323.15 5 1 0.004126 4 1 0.000256 6 1 1 10 1 Principal objective of the work EP EP 9/30/2019 1 Mole fraction Chromatography 1 Liquid Direct value, X 1 Data file compiler Propagation of evaluated standard uncertainties 95 Liquid Crystal 1 1 Pressure, kPa Liquid 101.2 4 1 Temperature, K Liquid 1 278.15 5 1 0.00121 4 1 7.5e-05 1 283.15 5 1 0.001477 4 1 9.2e-05 1 288.15 5 1 0.001723 4 1 0.000107 1 293.15 5 1 0.002158 4 1 0.000134 1 298.15 5 1 0.002597 4 1 0.000161 1 303.15 5 1 0.003081 4 1 0.000191 1 308.15 5 1 0.003782 4 1 0.000235 1 313.15 5 1 0.004459 4 1 0.000277 1 318.15 5 1 0.005425 4 1 0.000337 1 323.15 5 1 0.006383 4 1 0.000396 7 1 1 6 1 Principal objective of the work EP EP 9/30/2019 1 Mole fraction Chromatography 1 Liquid Direct value, X 1 Data file compiler Propagation of evaluated standard uncertainties 95 Liquid Crystal 1 1 Pressure, kPa Liquid 101.2 4 1 Temperature, K Liquid 1 278.15 5 1 0.0008145 4 1 5.05e-05 1 283.15 5 1 0.0009688 4 1 6.01e-05 1 288.15 5 1 0.001165 4 1 7.2e-05 1 293.15 5 1 0.001387 4 1 8.6e-05 1 298.15 5 1 0.00167 4 1 0.000104 1 303.15 5 1 0.001954 4 1 0.000121 1 308.15 5 1 0.002362 4 1 0.000147 1 313.15 5 1 0.002805 4 1 0.000174 1 318.15 5 1 0.003381 4 1 0.00021 1 323.15 5 1 0.004124 4 1 0.000256 8 1 1 7 1 Principal objective of the work EP EP 9/30/2019 1 Mole fraction Chromatography 1 Liquid Direct value, X 1 Data file compiler Propagation of evaluated standard uncertainties 95 Liquid Crystal 1 1 Pressure, kPa Liquid 101.2 4 1 Temperature, K Liquid 1 278.15 5 1 0.001519 4 1 9.4e-05 1 283.15 5 1 0.001758 4 1 0.000109 1 288.15 5 1 0.002111 4 1 0.000131 1 293.15 5 1 0.002494 4 1 0.000155 1 298.15 5 1 0.00293 4 1 0.000182 1 303.15 5 1 0.003525 4 1 0.000219 1 308.15 5 1 0.004106 4 1 0.000255 1 313.15 5 1 0.004871 4 1 0.000302 1 318.15 5 1 0.005769 4 1 0.000358 1 323.15 5 1 0.006653 4 1 0.000413 9 1 1 8 1 Principal objective of the work EP EP 9/30/2019 1 Mole fraction Chromatography 1 Liquid Direct value, X 1 Data file compiler Propagation of evaluated standard uncertainties 95 Liquid Crystal 1 1 Pressure, kPa Liquid 101.2 4 1 Temperature, K Liquid 1 278.15 5 1 0.0001194 4 1 7.4e-06 1 283.15 5 1 0.0001474 4 1 9.1e-06 1 288.15 5 1 0.0001849 4 1 1.15e-05 1 293.15 5 1 0.0002361 4 1 1.47e-05 1 298.15 5 1 0.0003013 4 1 1.87e-05 1 303.15 5 1 0.0003894 4 1 2.42e-05 1 308.15 5 1 0.0005006 4 1 3.11e-05 1 313.15 5 1 0.0006168 4 1 3.83e-05 1 318.15 5 1 0.0007396 4 1 4.59e-05 1 323.15 5 1 0.0009056 4 1 5.62e-05 10 1 1 12 1 Principal objective of the work EP EP 9/30/2019 1 Mole fraction Chromatography 1 Liquid Direct value, X 1 Data file compiler Propagation of evaluated standard uncertainties 95 Liquid Crystal 1 1 Pressure, kPa Liquid 101.2 4 1 Temperature, K Liquid 1 293.15 5 1 0.02513 4 1 0.00156 1 298.15 5 1 0.02923 4 1 0.00181 1 303.15 5 1 0.03369 4 1 0.00209 1 308.15 5 1 0.03894 4 1 0.00242 1 313.15 5 1 0.0447 4 1 0.00277 1 318.15 5 1 0.05133 4 1 0.00318 1 323.15 5 1 0.05979 4 1 0.00371 11 1 1 11 1 Principal objective of the work EP EP 9/30/2019 1 Mole fraction Chromatography 1 Liquid Direct value, X 1 Data file compiler Propagation of evaluated standard uncertainties 95 Liquid Crystal 1 1 Pressure, kPa Liquid 101.2 4 1 Temperature, K Liquid 1 278.15 5 1 0.008496 4 1 0.000527 1 283.15 5 1 0.009381 4 1 0.000582 1 288.15 5 1 0.0109 4 1 0.00068 1 293.15 5 1 0.01263 4 1 0.00078 1 298.15 5 1 0.01529 4 1 0.00095 1 303.15 5 1 0.01774 4 1 0.0011 1 308.15 5 1 0.02079 4 1 0.00129 1 313.15 5 1 0.02501 4 1 0.00155 1 318.15 5 1 0.02914 4 1 0.00181 1 323.15 5 1 0.03363 4 1 0.00209 12 1 1 9 1 Principal objective of the work EP EP 9/30/2019 1 Mole fraction Chromatography 1 Liquid Direct value, X 1 Data file compiler Propagation of evaluated standard uncertainties 95 Liquid Crystal 1 1 Pressure, kPa Liquid 101.2 4 1 Temperature, K Liquid 1 278.15 5 1 0.1347 4 1 0.0084 1 283.15 5 1 0.1415 4 1 0.0088 1 288.15 5 1 0.1493 4 1 0.0093 1 293.15 5 1 0.1591 4 1 0.0099 1 298.15 5 1 0.1689 4 1 0.0105 1 303.15 5 1 0.1789 4 1 0.0111 1 308.15 5 1 0.1888 4 1 0.0117 1 313.15 5 1 0.1992 4 1 0.0124 1 318.15 5 1 0.2113 4 1 0.0131 1 323.15 5 1 0.2271 4 1 0.0141