TY - JOUR
T1 - Solubility determination and thermodynamic model of 6-hydroxy-3,4-dihydro-2(1H)-quinolone in ten pure solvents and four binary solvents at 278.15 to 323.15 K
AU - Zhou, Peng
AU - Wang, Rensong
AU - Yang, Wenge
AU - Chen, Chen
AU - Xu, Hanhan
AU - Zhu, Fu
AU - Hu, Guoxing
AU - Hu, Yonghong
AU - Sun, Wei
AU - Shen, Weiliang
N1 - Publisher Copyright:
© 2021 Elsevier Ltd
PY - 2022/3
Y1 - 2022/3
N2 - 6-hydroxy-3,4-dihydro-2(1H)-quinolone is an important chemical intermediate, which has important application value in the fields of medicinal chemistry and material chemistry. In this paper, the static counterpoise method integrated with HPLC was used to detected the solubility of sample in 10 pure solvents (1-Butanol, methanol, ethanol, isopropanol, tetrahydrofuran, 1-Propanol, methyl acetate, ethyl acetate, acetonitrile and isobutanol) and four binary solvents (ethanol + ethyl acetate, ethanol + acetonitrile, methanol + acetonitrile, and methanol + ethyl acetate). The results reveals that the sample has higher solubility in methanol and ethanol in pure solvents. In binary solvents, the solubility has a maximum value at xA = 0.7. At the same temperature, the binary system can improve the solubility of sample more than pure solvents. At 278.15–323.15 K, themole fraction solubility ranges of the 6-hydroxy-3,4-dihydro-2(1H)-quinolone respectively are 0.0018–0.0062 (1-Butanol), 0.0022–0.0084 (methanol), 0.0021–0.0076 (ethanol), 0.0019–0.0072 (isopropanol), 0.0025–0.0065 (tetrahydrofuran), 0.0017–0.0064 (1-Propanol), 0.0016–0.0039 (methyl acetate), 0.0007–0.0013 (ethyl acetate), 0.0003–0.0012 (acetonitrile), 0.0011–0.0049 (isobutanol), 0.0010–0.0090 (ethanol + ethyl acetate), 0.0006–0.0095 (ethanol + acetonitrile), 0.0007–0.0092 (methanol + acetonitrile), 0.0009–0.0102 (methanol + ethyl acetate). The five models, such as the SUN model, λ h model, CNIBS/R-K model, Jouyban-Acree model and modified Apelblat model, were used to fit the experimental data. The CNIBS/R-K model and modified Apelblat model fit the data better in miscible and single solution respectively. In addition, the KAT-LSER model was used to study the relationship between solute-solvent interaction and sample solubility.
AB - 6-hydroxy-3,4-dihydro-2(1H)-quinolone is an important chemical intermediate, which has important application value in the fields of medicinal chemistry and material chemistry. In this paper, the static counterpoise method integrated with HPLC was used to detected the solubility of sample in 10 pure solvents (1-Butanol, methanol, ethanol, isopropanol, tetrahydrofuran, 1-Propanol, methyl acetate, ethyl acetate, acetonitrile and isobutanol) and four binary solvents (ethanol + ethyl acetate, ethanol + acetonitrile, methanol + acetonitrile, and methanol + ethyl acetate). The results reveals that the sample has higher solubility in methanol and ethanol in pure solvents. In binary solvents, the solubility has a maximum value at xA = 0.7. At the same temperature, the binary system can improve the solubility of sample more than pure solvents. At 278.15–323.15 K, themole fraction solubility ranges of the 6-hydroxy-3,4-dihydro-2(1H)-quinolone respectively are 0.0018–0.0062 (1-Butanol), 0.0022–0.0084 (methanol), 0.0021–0.0076 (ethanol), 0.0019–0.0072 (isopropanol), 0.0025–0.0065 (tetrahydrofuran), 0.0017–0.0064 (1-Propanol), 0.0016–0.0039 (methyl acetate), 0.0007–0.0013 (ethyl acetate), 0.0003–0.0012 (acetonitrile), 0.0011–0.0049 (isobutanol), 0.0010–0.0090 (ethanol + ethyl acetate), 0.0006–0.0095 (ethanol + acetonitrile), 0.0007–0.0092 (methanol + acetonitrile), 0.0009–0.0102 (methanol + ethyl acetate). The five models, such as the SUN model, λ h model, CNIBS/R-K model, Jouyban-Acree model and modified Apelblat model, were used to fit the experimental data. The CNIBS/R-K model and modified Apelblat model fit the data better in miscible and single solution respectively. In addition, the KAT-LSER model was used to study the relationship between solute-solvent interaction and sample solubility.
KW - 6-hydroxy-3,4-dihydro-2(1H)-quinolone
KW - KAT-LSER model
KW - Solubility
KW - Thermodynamic model
UR - http://www.scopus.com/inward/record.url?scp=85121122486&partnerID=8YFLogxK
U2 - 10.1016/j.jct.2021.106694
DO - 10.1016/j.jct.2021.106694
M3 - 文章
AN - SCOPUS:85121122486
SN - 0021-9614
VL - 166
JO - Journal of Chemical Thermodynamics
JF - Journal of Chemical Thermodynamics
M1 - 106694
ER -