Thermodynamics Research Center, ThermoML : Journal of Chemical and Engineering Data

Solubility Determination of 2-Chloronicotinic Acid and Analysis of Solvent Effect

Wu, Y.[Yufang], Wu, C.[Chengmeng], Yan, S.[Suyue], Hu, B.[Bin]
J. Chem. Eng. Data 2019, 64, 12, 5578-5583
ABSTRACT
The objective is to study the effect of solvent properties on solubility. In this work, the solubility of 2-chloronicotinic acid in methanol, ethanol, n-propanol, isopropanol, N,N-dimethylformamide (DMF), 1,4-dioxane, N-methyl pyrrolidone (NMP), ethyl acetate, acetone, water, acetonitrile and cyclohexane at temperatures ranging from 273.15 to 313.15 K was determined by isothermal saturation method under P =101.3 kPa. The maximum solubility value was obtained in pure NMP, and followed by in the DMF greater than ethyl acetate greater than acetone greater than 1,4-dioxane greater than n-propanol greater than isopropanol greater than ethanol greater than methanol greater than acetonitrile greater than cyclohexane greater than water. The obtained solubility data of 2-chloronicotinic acid in twelve pure solvents was correlated with the modified Apelblat equation and h equation. The maximum value of relative average deviations (RAD) and root-mean-square deviation (RMSD) are all no larger than 2.7210-2 and 35.5610-4, respectively, which indicates the experimental data is consistent well with calculated one. Furthermore, the properties of solvent including hydrogen bond acidity ( N w z hydrogen bond basicity ( O), dipolarity/polarizability ( a*) and Hildebrand solubility parameter ( ) were discussed. Compared with the polarity 2H O of the solvent, the hydrogen bond formed between the solvent and solute molecule is the main influencing factor. Understanding some physical properties of 2-chloronicotinic acid in commonly used organic solvents is important to drug crystallization.
Compounds
# Formula Name
1 C6H4ClNO2 2-chloronicotinic acid
2 CH4O methanol
3 C2H6O ethanol
4 C3H8O propan-1-ol
5 C3H8O propan-2-ol
6 C2H3N acetonitrile
7 C3H7NO dimethylformamide
8 C3H6O acetone
9 C4H8O2 ethyl acetate
10 C5H9NO N-methylpyrrolidone
11 C4H8O2 1,4-dioxane
12 C6H12 cyclohexane
13 H2O water
Datasets
The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type Compound-# Property Variable Constraint Phase Method #Points
  • POMD
  • 1
  • 2
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 3
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 4
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 5
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 7
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 11
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 6
  • POMD
  • 1
  • 10
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 9
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 8
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 13
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 6
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 12
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9