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Physicochemical Properties of Terebic Acid, MBTCA, Diaterpenylic Acid Acetate, and Pinanediol as Relevant ?-Pinene Oxidation Products.

ABSTRACT: The physicochemical properties and the synthesis of four ?-pinene oxidation products, terebic acid, 3-methyl-1,2,3-butanetricarboxylic acid (MBTCA), diaterpenylic acid acetate (DTAA), and pinanediol, are presented in this study. The physicochemical properties encompass thermal properties, solubility in water, and dissociation constant (pK a) for the investigated compounds. It was found that terebic acid exhibits a relatively high melting temperature of 449.29 K, whereas pinanediol revealed a low melting temperature of 329.26 K. The solubility in water was determined with the dynamic method and the experimental results were correlated using three different mathematical models: Wilson, NRTL, and UNIQUAC equations. The results of the correlation indicate that the Wilson equation appears to work the best for terebic acid and pinanediol. The calculated standard deviation was for 3.79 for terebic acid and 1.25 for pinanediol. In contrast, UNIQUAC was the best mathematical model for DTAA and MBTCA. The calculated standard deviation was 0.57 for DTAA and 2.21 for MBTCA. The measured water solubility increased in the following order: pinanediol > DTAA ? MBTCA > terebic acid, which affects their multiphase aging chemistry in the atmosphere. Moreover, acidity constants (pK a) at 298, 303, and 308 K were determined for DTAA with the Bates-Schwarzenbach spectrophotometric method. The pK a values obtained at 298, 303, and 308 K were found to be 3.76, 3.85, and 3.88, respectively.

SUBMITTER: Kolodziejczyk A

PROVIDER: S-EPMC7160834 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Physicochemical Properties of Terebic Acid, MBTCA, Diaterpenylic Acid Acetate, and Pinanediol as Relevant α-Pinene Oxidation Products.

Kołodziejczyk Agata A Pyrcz Patryk P Błaziak Kacper K Pobudkowska Aneta A Sarang Kumar K Szmigielski Rafał R

ACS omega 20200331 14

The physicochemical properties and the synthesis of four α-pinene oxidation products, terebic acid, 3-methyl-1,2,3-butanetricarboxylic acid (MBTCA), diaterpenylic acid acetate (DTAA), and pinanediol, are presented in this study. The physicochemical properties encompass thermal properties, solubility in water, and dissociation constant (p<i>K</i> <sub>a</sub>) for the investigated compounds. It was found that terebic acid exhibits a relatively high melting temperature of 449.29 K, whereas pinaned ...[more]

PMID: 32309701

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Project description:The formation of atmospheric cloud droplets due to secondary organic aerosol (SOA) particles is important for quantifying the Earth's radiative balance under future, possibly warmer, climates, yet is only poorly understood. While cloud activation may be parametrized using the surface tension depression that coincides with surfactant partitioning to the gas-droplet interface, the extent to which cloud activation is influenced by both the chemical structure and reactivity of the individual molecules comprising this surfactant pool is largely unknown. We report herein considerable differences in the surface tension depression of aqueous pendant droplets that contain synthetically prepared ozonolysis products derived from α-pinene and β-caryophyllene, the most abundant of the monoterpenes and sesquiterpenes, respectively, that are emitted over the planet's vast forest ecosystems. Oxidation products derived from β-caryophyllene were found to exhibit significantly higher surface activity than those prepared from α-pinene, with the critical supersaturation required for cloud droplet activation reduced by 50% for β-caryophyllene aldehyde at 1 mM. These considerable reductions in the critical supersaturation were found to coincide with free energies of adsorption that exceed ∼25 kJ/mol, or just one hydrogen bond equivalent, depending on the ammonium sulfate and oxidation product concentration in the solution. Additional experiments showed that aldehyde-containing oxidation products exist in equilibrium with hydrated forms in aqueous solution, which may modulate their bulk solubility and surface activity. Equilibration time scales on the order of 10-5 to 10-4 s calculated for micrometer-sized aerosol particles indicate instantaneous surface tension depression in the activation processes leading to cloud formation in the atmosphere. Our findings highlight the underlying importance of molecular structure and reactivity when considering cloud condensation activity in the presence of SOA particles.

Dataset Information

Physicochemical Properties of Terebic Acid, MBTCA, Diaterpenylic Acid Acetate, and Pinanediol as Relevant ?-Pinene Oxidation Products.

Publications

Physicochemical Properties of Terebic Acid, MBTCA, Diaterpenylic Acid Acetate, and Pinanediol as Relevant α-Pinene Oxidation Products.

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