Measurement and Thermodynamic Modeling of Lamotrigine Solubility in the Presence of Some Choline-Based Ionic Liquids

2023

The mole fraction of 3-amino-6-bromopyridazine in methanol, ethanol, n-propanol, isopropanol, n-butanol, acetone, toluene, propylene glycol (PG), N,Ndimethylformamide (DMF), and water and methanol/ethanol//PG/DMF + water was experimentally measured by the isothermal saturation method from 278.15 to 323.15 K under 101.2 kPa. The solubility range of 3-amino-6-bromopyridazine is from 2.574 × 10 −5 (water, 278.15 K) to 2.415 × 10 −2 (DMF, 323.15 K). Accordingly, under the given conditions, the mixing of DMF and water is superior to other combinations in terms of dissolution. The solubility of 3-amino-6-bromopyridazine in mono-solvents was correlated with Apelblat, van't Hoff, and λh models. Jouyban−Acree (J-A), modified Apelblat−Jouyban−Acree (A-J-A), and van't Hoff−Jouyban−Acree (V-J-A) models were applied to calculate the solubility of 3-amino-6-bromopyridazine in four solvent mixtures. In terms of thermodynamic properties, the fusion enthalpy (Δ fus H = 37.01 kJ mol −1 ) and melting point (T m = 472.15 K) of 3-amino-6-bromopyridazine are obtained by a differential scanning calorimeter. The interaction between the solute and solvent molecules as well as the interaction generated inside the above molecules could be analyzed through the calculation of the extended Hildebrand solubility parameter approach. The results showed that hydrophobic action of intramolecular groups and self-association of solute and solvent occurred in different concentration ranges.

Section: ■ Introductionsupporting

confidence: 89%

Equilibrium Solubility, Modeling, and Extended Hildebrand Solubility Parameter Approach Analysis of 3-Amino-6-bromopyridazine in Four Cosolvent Blends and Ten Pure Solvents at T = 278.15 to 323.15 K

2023

“…Although the polarity of PG is stronger than that of methanol, the solubility of 2-amino-5-bromopyrazine in PG is greater than that in methanol, which may be due to the better fit between the molecular structure of PG and the structure of 2-amino-5-bromopyrazine. For water, its maximum polarity results in its weakest ability to dissolve solutes …”

Section: Resultsmentioning

confidence: 99%

“… a The density of 2-amino-5-bromopyrazine calculated by using Advanced Chemistry Development (ACD/Labs) software V11.02 (1994-2022 ACD/Labs). b The melting point of 2-amino-5-bromopyrazine taken from refs , , , . c High-performance liquid chromatography. d The melting point of 2-amino-5-bromopyrazine measured in this work. e Taken from ref . f Gas chromatography. …”

Section: Methodsmentioning

confidence: 99%

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Solubility Measurement and Correlation of 2-Amino-5-bromopyrazine in Methanol/Ethanol/Isopropanol/Propylene Glycol Plus Water and 10 Pure Solvents at (278.15–323.15) K

Huang

2023

The solubility of 2-amino-5-bromopyrazine in the co-solvent mixtures of methanol, ethanol, isopropanol, and propylene glycol (PG) plus water and 10 monosolvents (methanol, ethanol, isopropanol, N,N-dimethylformamide (DMF), n-propanol, n-butanol, acetone, ethylene glycol (EG), PG, and water) was experimentally measured by the isothermal method at 278.15–323.15 K under 101.2 kPa. The temperature dominated the trend of solubility of 2-amino-5-bromopyrazine in pure and mixed solvents, especially high temperatures had a positive effect on dissolution. For the pure solvent system, the maximum solubility was obtained in DMF. For the mixed systems, isopropanol + water was superior to the other three combinations. The Apelblat model, van’t Hoff model, and NRTL model were used to correlate the solubility of 2-amino-5-bromopyrazine in 10 monosolvents. Furthermore, three thermodynamic co-solvency models including the Jouyban–Acree (JA) model, the Van’t Hoff–Jouyban–Acree (VJA) model, and the modified Apelblat–Jouyban–Acree (AJA) model were used to calculate the solubility data. This study would be helpful to the synthesis and purification processes of the final product.

“… a Melting point of 6-bromo-2-methylquinoline taken from refs –. b Melting point of 6-bromo-2-methylquinoline measured in this work. c Density of 6-bromo-2-methylquinoline calculated by using Advanced Chemistry Development (ACD/Labs) Software V11.02 (1994-2022 ACD/Labs). d Taken from ref . …”

Section: Methodsmentioning

confidence: 99%

Study on 6-Bromo-2-methylquinoline in Ten Monosolvents and Four Binary Blends at 278.15–323.15 K: Solubility, Correlation, and Solvent Effect

Huang

2023

The equilibrium solubility of 6-bromo-2-methylquinoline in various binary blends [ethanol/isopropanol/N,N-dimethylformamide (DMF)/methanol + water] and ten monosolvents (methanol, ethanol, n-propanol, isopropanol, ethyl acetate, toluene, acetone, acetonitrile, DMF, and water) was studied by the isothermal method at 278.15−323.15 K under 101.2 kPa. Among the ten pure solvents, the maximum solubility in mole fraction was obtained in toluene (3.318 × 10 −2 ), followed by ethyl acetate (2.991 × 10 −2 ), acetone (2.764 × 10 −2 ), acetonitrile (2.528 × 10 −2 ), DMF (2.220 × 10 −2 ), n-propanol (9.141 × 10 −3 ), isopropanol (8.123 × 10 −3 ), ethanol (3.896 × 10 −3 ), methanol (9.981 × 10 −4 ), and water (2.888 × 10 −5 ) at 323.15 K. In four solvent mixtures, the maximum and minimum solubilities were obtained in the (DMF + water) and (methanol + water) blends. The solubility of 6-bromo-2-methylquinoline in pure solvents was only affected by temperature and calculated by the Apelblat, van't Hoff, and NRTL models. The Jouyban−Acree (J−A), van't Hoff−Jouyban−Acree (V− J−A), and modified Apelblat−Jouyban−Acree (A−J−A) models were used to evaluate the solubility data in mixed systems. The calculation of solvent effect deeply explored the dissolution behavior of 6-bromo-2-methylquinoline from the molecular point of view, and the results showed that the interaction between the solute and solvent was dominant. The apparent thermodynamic properties of 6-bromo-2-methylquinoline in pure solvents were obtained by van't Hoff plots.