Experimental Determination and Computational Prediction of Dehydroabietic Acid Solubility in (−)-α-Pinene + (−)-β-Caryophyllene + P-Cymene System

Yanmin Qin; Xiaopeng Chen; Linlin Wang; Xiaojie Wei; Weijian Nong; Xuejuan Wei; Jiezhen Liang

doi:10.3390/molecules27041220

Molecules (Feb 2022)

Experimental Determination and Computational Prediction of Dehydroabietic Acid Solubility in (−)-α-Pinene + (−)-β-Caryophyllene + P-Cymene System

Yanmin Qin,
Xiaopeng Chen,
Linlin Wang,
Xiaojie Wei,
Weijian Nong,
Xuejuan Wei,
Jiezhen Liang

Affiliations

Yanmin Qin: Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China
Xiaopeng Chen: Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China
Linlin Wang: Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China
Xiaojie Wei: Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China
Weijian Nong: China Academy of Science and Technology Development Guangxi Branch, Nanning 530022, China
Xuejuan Wei: Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China
Jiezhen Liang: Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China

DOI: https://doi.org/10.3390/molecules27041220
Journal volume & issue: Vol. 27, no. 4
p. 1220

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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