Solubility and Hansen Solubility Parameters of N-Benzyloxycarbonyl-l-serine in 12 Monosolvents from 283.15 to 323.15 K

The solid-liquid equilibrium solubility and solventeffectsof N-benzyloxycarbonyl-l-serine in 12 monosolventsystems (water, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, n-pentanol, acetonitrile, 2-butanone, acetone, methyl acetate,and ethyl acetate) were reported in this work. All of the solubilitydata were measured at 283.15-323.15 K (5 K interval) by thestatic gravimetric method at a pressure of 101.2 kPa. Among the 12monosolvents, the solubility increased with the increase of absolutetemperature; the order is acetone > isopropanol > n-propanol > sec-butanol > n-butanol> 2-butanone > isobutanol & AP; n-pentanol> methylacetate > ethyl acetate > acetonitrile > water. The solubilityisthe largest in acetone (0.2055 mol & BULL;mol(-1) at323.15 K) and the smallest in water (9.737 x 10(-4) mol & BULL;mol(-1) at 283.15 K). According to thesolubility data analysis results, the solubility of N-benzyloxycarbonyl-l-serine is positively correlated withthe polarity of the solvent. However, its solubility could be affectedby other factors, such as propensity for hydrogen bonding acceptorfor isopropanol, structural similarity for acetone, cohesive energydensity for water, acetonitrile, and sec-butanol,which lead to different dissolution behavior. In addition, the Hansensolubility parameters (HSPs) were used to further analyze its solubilitybehavior. The Yaws model and the modified Apelblat model were employedto correlate the experimental solubility, and the fitting resultsof the two models were both well. In addition, through the comparisonof the AIC values and Akaike weights of the two models, the modifiedApelblat model yielded a more satisfactory correlation result. Theresults may provide a theoretical basis for the preparation and applicationof N-benzyloxycarbonyl-l-serine.