Abstract
The solubility of dehydroabietic acid in (−)-α-pinene, p-cymene, (−)-β-caryophyllene, (−)-α-pinene + p-cymene, (−)-β-caryophyllene + p-cymene and (−)-α-pinene + (−)-β-caryophyllene were determined using the laser monitoring method at atmospheric pressure. The solubility of dehydroabietic acid was positively correlated with temperature from 295.15 to 339.46 K. (−)-α-pinene, p-cymene, and (−)-β-caryophyllene were found to be suitable for the solubilization of dehydroabietic acid. In addition, the non-random two liquid (NRTL), universal quasi-chemical (UNIQUAC), modified Apelblat, modified Wilson, modified Wilson–van’t Hoff, and λh models were applied to correlate the determined solubility data. The modified Apelblat model gave the minor deviation for dehydroabietic acid in monosolvents, while the λh equation showed the best result in the binary solvents. A comparative analysis of compatibility between solutes and solvents was carried out using Hansen solubility parameters. The thermodynamic functions of ΔsolH0, ΔsolS0, ΔsolG0 were calculated according to the van’t Hoff equation, indicating that the dissolution was an entropy-driven heat absorption process. The Conductor-like Screening Model for Real Solvents (COSMO-RS) combined with an experimental value was applied to predict the reasonable solubility data of dehydroabietic acid in the selected solvents systems. The interaction energy of the dehydroabietic acid with the solvent was analyzed by COSMO-RS.
Highlights
Pine resin is an inexpensive and biodegradable natural resource, which is abundant in pine and coniferous trees [1]
The onset melting temperature of dehydroabietic acid (Tm) is 443.22 K, which is in general agreement with the literature values [15] (442.65 to 443.55 K in the literature)
The solubility of dehydroabietic acid was investigated in three monosolvents ((−)-α-pinene, (−)-β-caryophyllene, and p-cymene) and three mixed solvents ((−)-α-pinene + p-cymene, (−)-β-caryophyllene + p-cymene, and (−)-α-pinene + (−)-βcaryophyllene)
Summary
Pine resin is an inexpensive and biodegradable natural resource, which is abundant in pine and coniferous trees [1]. It is commonly used as an antimicrobial agent [2], paint, ink toner, and for coatings [3,4]. The most important products of pine resin are rosin and turpentine obtained via distillation [5]. Turpentine is a terpene mixture mainly composed of monoterpenes such as (−)-α-pinene, β-pinene, camphene, p-cymene, and sesquiterpenes such as longifolene and (−)-β-caryophyllene. The monoterpenes are volatile components in a boiling point range of 155–175 ◦C at atmospheric pressure, while the boiling points of sesquiterpenes are in a range of 254–256 ◦C at atmospheric pressure
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