Measurement and prediction of isothermal vapor–liquid equilibrium of α-pinene + camphene/longifolene + abietic acid + palustric acid + neoabietic acid systems

doi:10.1016/j.cjche.2021.12.030

中国化学工程学报 ›› 2023, Vol. 53 ›› Issue (1): 155-169.DOI: 10.1016/j.cjche.2021.12.030

• Full Length Article • 上一篇下一篇

Measurement and prediction of isothermal vapor–liquid equilibrium of α-pinene + camphene/longifolene + abietic acid + palustric acid + neoabietic acid systems

Youqi Li¹, Xiaopeng Chen¹, Linlin Wang¹, Xiaojie Wei¹, Weijian Nong^2,3, Xuejuan Wei¹, Jiezhen Liang¹

1. Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China;
2. China Academy of Science and Technology Development Guangxi Branch, Nanning 530022, China;
3. Guangxi Sci-Tech Development Forest-like Technology Co. Ltd, Nanning 530022, China

收稿日期:2021-10-15 修回日期:2021-12-21 出版日期:2023-01-28 发布日期:2023-04-08
通讯作者: Jiezhen Liang,E-mail:ljztony01@163.com
基金资助:
We acknowledge the support for this work from the National Natural Science Foundation of China (31960294, 32160349), Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology (2017Z005, 2020Z005), the Project for Cultivating New Century Academic and Technology Leaders of Nanning City (2020010) and the High-Performance Computing Platform of Guangxi University.

Measurement and prediction of isothermal vapor–liquid equilibrium of α-pinene + camphene/longifolene + abietic acid + palustric acid + neoabietic acid systems

Youqi Li¹, Xiaopeng Chen¹, Linlin Wang¹, Xiaojie Wei¹, Weijian Nong^2,3, Xuejuan Wei¹, Jiezhen Liang¹

1. Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China;
2. China Academy of Science and Technology Development Guangxi Branch, Nanning 530022, China;
3. Guangxi Sci-Tech Development Forest-like Technology Co. Ltd, Nanning 530022, China

Received:2021-10-15 Revised:2021-12-21 Online:2023-01-28 Published:2023-04-08
Contact: Jiezhen Liang,E-mail:ljztony01@163.com
Supported by:
We acknowledge the support for this work from the National Natural Science Foundation of China (31960294, 32160349), Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology (2017Z005, 2020Z005), the Project for Cultivating New Century Academic and Technology Leaders of Nanning City (2020010) and the High-Performance Computing Platform of Guangxi University.

摘要/Abstract

摘要： The vapor–liquid equilibrium (VLE) data of α-pinene + camphene + [abietic acid + palustric acid + neoabietic acid] and α-pinene + longifolene + [abietic acid + palustric acid + neoabietic acid] systems at 313.15 K, 333.15 K and 358.15 K were measured by headspace gas chromatography (HSGC). These data was compared with the predictions value by conductor-like screening model for realistic solvation (COSMO-RS). Moreover, the calculated data of COSMO-RS and Non-Random Two-Liquids (NRTL) models showed good agreement with the experimental data. It was found that the three resin acids inhibited the volatility of α-pinene, camphene and longifolene and resulted in the decrease of total pressure. Moreover, H^E(HB) contributes the most to the excess enthalpy and the hydrogen bonding interaction is the dominant intermolecular force of α-pinene, camphene and longifolene with the three resin acids. In addition, the geometric structures optimization and binding energy were obtained by the DFT to further illustrate the hydrogen bonding interaction and the effects of the addition of the three resin acids on the isothermal VLE.

关键词: Isothermal vapor–liquid equilibrium, Headspace gas chromatography, COSMO-RS model, DFT

Abstract: The vapor–liquid equilibrium (VLE) data of α-pinene + camphene + [abietic acid + palustric acid + neoabietic acid] and α-pinene + longifolene + [abietic acid + palustric acid + neoabietic acid] systems at 313.15 K, 333.15 K and 358.15 K were measured by headspace gas chromatography (HSGC). These data was compared with the predictions value by conductor-like screening model for realistic solvation (COSMO-RS). Moreover, the calculated data of COSMO-RS and Non-Random Two-Liquids (NRTL) models showed good agreement with the experimental data. It was found that the three resin acids inhibited the volatility of α-pinene, camphene and longifolene and resulted in the decrease of total pressure. Moreover, H^E(HB) contributes the most to the excess enthalpy and the hydrogen bonding interaction is the dominant intermolecular force of α-pinene, camphene and longifolene with the three resin acids. In addition, the geometric structures optimization and binding energy were obtained by the DFT to further illustrate the hydrogen bonding interaction and the effects of the addition of the three resin acids on the isothermal VLE.

Key words: Isothermal vapor–liquid equilibrium, Headspace gas chromatography, COSMO-RS model, DFT

Youqi Li, Xiaopeng Chen, Linlin Wang, Xiaojie Wei, Weijian Nong, Xuejuan Wei, Jiezhen Liang. Measurement and prediction of isothermal vapor–liquid equilibrium of α-pinene + camphene/longifolene + abietic acid + palustric acid + neoabietic acid systems[J]. 中国化学工程学报, 2023, 53(1): 155-169.

参考文献

[1] A. Budiman, T.I. Arifta, diana Diana, S. Sutijan, Continuous production of α-terpineol from α-pinene isolated from Indonesian crude turpentine, Mod. Appl. Sci. 9 (4) (2015) 225.
[2] K. Li, J. Liggio, P. Lee, C. Han, Q.F. Liu, S.M. Li, Secondary organic aerosol formation from α-pinene, alkanes, and oil-sands-related precursors in a new oxidation flow reactor, Atmos. Chem. Phys. 19 (15) (2019) 9715-9731.
[3] C.J.A. Ribeiro, M.M. Pereira, E.F. Kozhevnikova, I.V. Kozhevnikov, E.V. Gusevskaya, K.A. da Silva Rocha, Heteropoly acid catalysts in upgrading of biorenewables:Synthesis of Para-menthenic fragrance compounds from α-pinene oxide, Catal. Today 344 (2020) 166-170.
[4] G.S. Lin, X. Bai, W.G. Duan, B. Cen, M. Huang, S.Z. Lu, High value-added application of sustainable natural forest product α-pinene:Synthesis of myrtenal oxime esters as potential KARI inhibitors, ACS Sustainable Chem. Eng. 7 (8) (2019) 7862-7868.
[5] N. Wijayati, E. Kusumastuti, D. Alighiri, B. Rohmawati, R. A. Lusiana, Heterogeneous zeolite-based catalyst for esterification of α-pinene to α-terpinyl acetate, Orient. J. Chem. 35 (1) (2019) 399
[6] E. Faujdar, H. Negi, R.K. Singh, V.K. Varshney, Study on biodegradable poly(α-olefins-co-α-pinene) architectures as pour point depressant and viscosity index improver additive for lubricating oils, J. Polym. Environ. 28 (11) (2020) 3019-3027.
[7] V.V. Fomenko, S.S. Laev, N.F. Salakhutdinov, Catalytic epoxidation of 3-carene and limonene with aqueous hydrogen peroxide, and selective synthesis of α-pinene epoxide from turpentine, Catalysts 11 (4) (2021) 436.
[8] P.P. Tao, X.H. Lu, H.F. Zhang, R. Jing, F.F. Huang, S. Wu, D. Zhou, Q.H. Xia, Enhanced activity of microwave-activated CoOx/MOR catalyst for the epoxidation of α-pinene with air, Mol. Catal. 463 (2019) 8-15.
[9] J. Meyer-Waßewitz, D. Elyorgun, C. Conradi, A. Drews, Dynamic modeling of the chemo-enzymatic epoxidation of α-pinene and prediction of continuous process performance, Chem. Eng. Res. Des. 134 (2018) 463-475.
[10] S.W. Liu, L. Zhou, S.T. Yu, C.X. Xie, F.S. Liu, Z.Q. Song, Polymerization of α-pinene using Lewis acidic ionic liquid as catalyst for production of terpene resin, Biomass Bioenergy 57 (2013) 238-242.
[11] D.L. Trumbo, C.L. Giddings, L.R.A. Wilson, Terpene-anhydride resins as coating materials, J. Appl. Polym. Sci. 58 (1) (1995) 69-76.
[12] B.J. Mehta, N. Krishnaswamy, Synthetic ion exchange resins from α-pinene, J. Appl. Polym. Sci. 18 (5) (1974) 1585.
[13] A.L.P. de Meireles, K.A. da Silva Rocha, I.V. Kozhevnikov, E.V. Gusevskaya, Esterification of camphene over heterogeneous heteropoly acid catalysts:Synthesis of isobornyl carboxylates, Appl. Catal. A Gen. 409-410 (2011) 82-86.
[14] Y.W. Moon, K.H. Shin, Y.H. Koh, S.W. Yook, C.M. Han, H.E. Kim, Novel ceramic/camphene-based co-extrusion for highly aligned porous alumina ceramic tubes, J. Am. Ceram. Soc. 95 (6) (2012) 1803-1806.
[15] A. Mukai, K. Takahashi, T. Ashitani, Natural autoxidation of longifolene and anti-termite activities of the products, J. Wood Sci. 63 (4) (2017) 360-368.
[16] X.P. Liu, W. Chen, Q.X. Liu, J.G. Dai, Abietic acid suppresses non-small-cell lung cancer cell growth via blocking IKKβ/NF-κB signaling, Onco. Targets Ther. 12 (2019) 4825-4837.
[17] V. Cuzzucoli Crucitti, L.M. Migneco, A. Piozzi, V. Taresco, M. Garnett, R.H. Argent, I. Francolini, Intermolecular interaction and solid state characterization of abietic acid/chitosan solid dispersions possessing antimicrobial and antioxidant properties, Eur. J. Pharm. Biopharm. 125 (2018) 114-123.
[18] Y. Ito, T. Ito, K. Yamashiro, F. Mineshiba, K. Hirai, K. Omori, T. Yamamoto, S. Takashiba, Antimicrobial and antibiofilm effects of abietic acid on cariogenic Streptococcus mutans, Odontology 108 (1) (2020) 57-65.
[19] R. Tanaka, H. Tokuda, Y. Ezaki, Cancer chemopreventive activity of "rosin" constituents of Pinus spez. and their derivatives in two-stage mouse skin carcinogenesis test, Phytomedicine 15 (11) (2008) 985-992.
[20] E. Wenkert, J.R. Mahajan, M. Nussim, F. Schenker, Conversion of neoabietic acid into manool, Can. J. Chem. 44 (21) (1966) 2575-2579.
[21] C.A. Elliger, D.F. Zinkel, B.G. Chan, A.C. Waiss Jr, Diterpene acids as larval growth inhibitors, Experientia 32 (11) (1976) 1364-1366.
[22] J.Z. Wu, L.L. Wang, X.P. Chen, X.J. Wei, J.Z. Liang, G.Y. Yao, P. Zheng, Measurement and correlation of vapor-liquid equilibrium data for binary systems composed of camphene, (+)-3-carene, (-)-β-caryophyllene, p-cymene, and α-pinene at 101.33 kPa, Thermochimica Acta 679 (2019) 178318.
[23] F. X. Ruan, J. K. Che, J. Hu, Y. Wang, B. Yuan, L. C. Zhou, Vapor-liquid equilibrium of α-pinene-pinane-longifolene system and its excess Gibbs free energy and excess enthalpy, J. Chem. Eng. Chin. Univ. 29 (6) (2015) 1306-1312.(in Chinese)
[24] N.H. Snow, G.C. Slack, Head-space analysis in modern gas chromatography, Trac Trends Anal. Chem. 21 (9-10) (2002) 608-617.
[25] M. Ayuso, A.M. Palma, M. Larriba, N. Delgado-Mellado, J. García, F. Rodríguez, J.A.P. Coutinho, P.J. Carvalho, P. Navarro, Experimental and CPA EoS description of the key components in the BTX separation from gasolines by extractive distillation with tricyanomethanide-based ionic liquids, Ind. Eng. Chem. Res. 59 (33) (2020) 15058-15068.
[26] Zheng P, Wang L. L, Chen X. P., X. J. Wei, J. Z. Liang, J. Z. Wu, Excess Gibbs Energies and Isothermal Vapor-Liquid Equilibrium for Citral + Linalool, Citral + α-Pinene, and Linalool + α-Pinene Systems Using Headspace Gas Chromatography, J. Chem. Eng. Data. 65 (7) (2020) 3593-3604.
[27] A. Klamt, Conductor-like screening model for real solvents:A new approach to the quantitative calculation of solvation phenomena, J. Phys. Chem. 99 (7) (1995) 2224-2235.
[28] A. Klamt, F. Eckert, Erratum to "COSMO-RS:A novel and efficient method for the a priori prediction of thermophysical data of liquids, Fluid Phase Equilib. 172 (1) (2000) 43-72.
[29] A. Klamt, G.J.P. Krooshof, R. Taylor, COSMOSPACE:Alternative to conventional activity-coefficient models, AIChE J. 48 (10) (2002) 2332-2349.
[30] A. Klamt, The COSMO and COSMO-RS solvation models, Wires Comput. Mol. Sci. 1 (5) (2011) 699-709.
[31] P. Pullumbi, COSMO-RS, from quantum chemistry to fluid phase thermodynamics and drug design, AIChE J. 9(2006)3328.
[32] P.C. Petris, P. Becherer, J.G.E.M. Fraaije, Alkane/water partition coefficient calculation based on the modified AM1 method and internal hydrogen bonding sampling using COSMO-RS, J. Chem. Inf. Modeling 61 (7) (2021) 3453-3462.
[33] J. Warnau, K. Wichmann, J. Reinisch, COSMO-RS predictions of logP in the SAMPL7 blind challenge, J. Comput. Aided Mol. Des. 35 (7) (2021) 813-818.
[34] Z.H. Wang, S.L. Liu, Y.F. Jiang, Z.G. Lei, J. Zhang, R.S. Zhu, J.W. Ren, Methyl chloride dehydration with ionic liquid based on COSMO-RS model, Green Energy Environ. 6 (3) (2021) 413-421.
[35] I.C. Hwang, S.J. Park, S.Y. Lee, H.S. Ahn, Isothermal vapor-liquid equilibrium at 333.15 K and excess molar volumes at 298.15 K for the ternary system di-isopropyl ether + n-propyl alcohol + toluene and its binary subsystems, Fluid Phase Equilibria 270 (1-2) (2008) 103-108.
[36] A. Klamt, F. Eckert, Prediction of vapor liquid equilibria using COSMOtherm, Fluid Phase Equilibria 217 (1) (2004) 53-57.
[37] Z.M. Bai, H.H. Liu, Y.S. Liu, L.H. Wu, Prediction of the vapor-liquid equilibrium of chemical reactive systems containing formaldehyde using the COSMO-RS method, Fluid Phase Equilibria 415 (2016) 125-133.
[38] H.H.Y. Chien, H.R. Null, Generalized multicomponent equation for activity coefficient calculation, AIChE J. 18 (6) (1972) 1177-1183.
[39] B.S. Jhaveri, G.K. Youngren, Three-parameter modification of the Peng-Robinson equation of state to improve volumetric predictions, SPE Reserv. Eng. 3 (3) (1988) 1033-1040.
[40] E. Ruiz, V.R. Ferro, J. Palomar, J. Ortega, J.J. Rodriguez, Interactions of ionic liquids and acetone:Thermodynamic properties, quantum-chemical calculations, and NMR analysis, J. Phys. Chem. B 117 (24) (2013) 7388-7398.
[41] G. Y. Yao, L. L. Wang, X. P. Chen, D. Q. Liao, Z. F. Tong, F. H. Lei, P. F. Li, Excess enthalpies of binary systems of β-strophanthrene, p-cymene and 3-carene, J. Chem. Eng. Chin. Univ. 32 (4) (2018) 779-784.(in Chinese)
[42] P.B. Armentrout, E.I. Armentrout, A.A. Clark, T.E. Cooper, E.M.S. Stennett, D.R. Carl, An experimental and theoretical study of alkali metal cation interactions with cysteine, J. Phys. Chem. B 114 (11) (2010) 3927-3937.
[43] V.N. Bowman, A.L. Heaton, P.B. Armentrout, Metal cation dependence of interactions with amino acids:Bond energies of Rb+ to Gly, Ser, Thr, and Pro, J. Phys. Chem. B 114 (11) (2010) 4107-4114.
[44] S. Huang, Z.H. Wang, S.L. Liu, R.S. Zhu, Z.G. Lei, Measurement and prediction of vapor pressure in binary systems containing the ionic liquid[EMIM] [DCA, J. Mol. Liq. 309 (2020) 113126.
[45] S.L. Liu, Z.H. Wang, R.S. Zhu, Z.G. Lei, J.Q. Zhu, EMIM] [DCA]as an entrainer for the extractive distillation of methanol-ethanol-water system, Green Energy Environ. 6 (3) (2021) 363-370.

Measurement and prediction of isothermal vapor–liquid equilibrium of α-pinene + camphene/longifolene + abietic acid + palustric acid + neoabietic acid systems

Measurement and prediction of isothermal vapor–liquid equilibrium of α-pinene + camphene/longifolene + abietic acid + palustric acid + neoabietic acid systems

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