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Densities, Vapor Pressures, and Surface Tensions of Selected Terpenes

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Abstract

The knowledge of physico-chemical properties of terpenes and terpenoids are necessary for understanding of formation of cloud condensation nuclei. In this work properties of \(\upalpha\)-pinene and \(\upbeta\)-pinene, namely liquid densities, saturated vapor pressure, surface tension and interfacial tension in mixtures with water were measured in the temperature range between 300 and 370 K. Saturated vapor pressures were also modelled by COSMO-RS and compared both with our mesurements and literature values measured at lower temperatures. A modern nonstatistical technique based on mathematical gnostics was used for data analysis.

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References

  1. Andreae, M.O., Rosenfeld, D.: Aerosol–cloud–precipitation interactions. Part 1. The nature and sources of cloud-active aerosols. Earth-Sci. Rev. 89(1–2), 13–41 (2008)

    Article  Google Scholar 

  2. Andresová, A., Bendová, M., Schwarz, J., Wagner, Z., Feder-Kubis, J.: Influence of the alkyl side chain length on the thermophysical properties of chiral ionic liquids with a (1R,2S,5R)-(–)-menthol substituent and data analysis by means of mathematical gnostics. J. Mol. Liq. 242, 336–348 (2017)

    Article  CAS  Google Scholar 

  3. Barth, M., McFadden, J.P., Sun, J., Wiedinmyer, C., Chuang, P., Collins, D., Griffin, R., Hannigan, M., Karl, T., Kim, S.W., Lasher-Trapp, S., Levis, S., Litvak, M., Mahowald, N., Moore, K., Nandi, S., Nemitz, E., Nenes, A., Potosnak, M., Raymond, T.M., Smith, J., Still, C., Stroud, C.: Coupling between land ecosystems and the atmospheric hydrologic cycle through biogenic aerosol pathways. Bull. Am. Meteor. Soc. 86(12), 1738–1742 (2005)

    Article  Google Scholar 

  4. Bayala, B., Bassole, I.H.N., Scifo, R., Gnoula, C., Morel, L., Lobaccaro, J.M.A., Simpore, J.: Anticancer activity of essential oils and their chemical components—a review. Am. J. Cancer Res. 4, 591–607 (2014)

    CAS  PubMed  PubMed Central  Google Scholar 

  5. Beck, J.V., Arnold, K.J.: Parameter Estimation in Engineering and Science. Wiley, New York (1977)

    Google Scholar 

  6. Chirico, R.D., Frenkel, M., Magee, J.W., Diky, V., Muzny, C.D., Kazakov, A.F., Kroenlein, K., Abdulagatov, I., Hardin, G.R., Acree Jr., W.E., Brenneke, J.F., Brown, P.L., Cummings, P.T., de Loos, T.W., Friend, D.G., Goodwin, A.R.H., Hansen, L.D., Haynes, W.M., Koga, N., Mandelis, A., Marsh, K.N., Mathias, P.M., McCabe, C., O’Connell, J.P., Pádua, A., Rives, V., Schick, C., Trusler, J.P.M., Vyazovkin, S., Weir, R.D., Wu, J.: Improvement of quality in publication of experimental thermophysical property data: challenges, assessment tools, global implementation, and online support. J. Chem. Eng. Data. 58, 2699–2716 (2013). https://doi.org/10.1021/je400569s

    Article  CAS  Google Scholar 

  7. Clarke, E.C.W., Glew, D.N.: Evaluation of thermodynamic functions from equilibrium constants. Trans. Faraday Soc. 62, 539–547 (1966). https://doi.org/10.1039/TF9666200539

    Article  CAS  Google Scholar 

  8. COSMOlogic GmbH & Co. KG: COSMOthermX User Guide (2017). www.cosmologic.de. Accessed 1 Apr 2019

  9. da Silva, A.C.R., Lopes, P.M., de Azevedo, M.M.B., Costa, D.C.M., Alviano, C.S., Alviano, D.S.: Biological activities of \(\upalpha\)-pinene and \(\upbeta\)-pinene enantiomers. Molecules 17, 6305–6316 (2012). https://doi.org/10.3390/molecules17066305

    Article  CAS  PubMed  Google Scholar 

  10. Daisey, J., Hopke, P.: Potential for ion-induced nucleation of volatile organic compounds by radon decay in indoor environments. Aerosol Sci. Technol. 19, 80–93 (1993)

    Article  CAS  Google Scholar 

  11. Eckert, F., Klamt, A.: Fast solvent screening via quantum chemistry: COSMO-RS approach. AIChE J. 48(2), 369–385 (2002)

    Article  CAS  Google Scholar 

  12. Eckert, F., Klamt, A.: COSMOtherm, Version C3.0, Release 16.01. COSMOlogic GmbH & Co. KG, Leverkusen, Germany (2014)

  13. Ehn, M., Thornton, J.A., Kleist, E., Sipila, M., Junninen, H., Pullinen, I., Springer, M., Rubach, F., Tillmann, R., Lee, B., Lopez-Hilfiker, F., Andres, S., Acir, I.H., Rissanen, M., Jokinen, T., Schobesberger, S., Kangasluoma, J., Kontkanen, J., Nieminen, T., Kurten, T., Nielsen, L.B., Jorgensen, S., Kjaergaard, H.G., Canagaratna, M., Maso, M.D., Berndt, T., Petaja, T., Wahner, A., Kerminen, V.M., Kulmala, M., Worsnop, D.R., Wildt, J., Mentel, T.F.: A large source of low-volatility secondary organic aerosol. Nature 506, 476–479 (2014). https://doi.org/10.1038/nature13032

    Article  CAS  PubMed  Google Scholar 

  14. Fedora. https://getfedora.org/. Accessed 1 Apr 2019

  15. Gaiolas, C., Belgacem, M.N., Silva, L., Thielemans, W., Costa, A.P., Nunes, M., Silva, M.J.S.: Green chemicals and process to graft cellulose fibers. J. Colloid Interface Sci. 330(2), 298–302 (2009)

    Article  CAS  PubMed  Google Scholar 

  16. Guggenheim, E.A.: Modern Thermodynamics. Menthuen and Co., Ltd., London (1933)

    Google Scholar 

  17. Guzmán-Gutiérrez, S.L., Gómez-Cansino, R., García-Zebadúa, J.C., Jiménez-Pérez, N.C., Reyes-Chilpa, R.: Antidepressant activity of litsea glaucescens essential oil: identification of \(\upbeta\)-pinene and linalool as active principles. J. Ethnoparm. 143, 673–679 (2012). https://doi.org/10.1016/j.jep.2012.07.026

    Article  CAS  Google Scholar 

  18. Hawkins, J.E., Armstrong, G.T.: Physical and thermodynamic properties of terpenes. III. The vapor pressures of \(\upalpha\)-pinene and \(\upbeta\)-pinene. J. Am. Chem. Soc. 76, 3756–3758 (1954). https://doi.org/10.1021/ja01643a051

    Article  CAS  Google Scholar 

  19. Heiberger, R.M., Becker, R.A.: Design of an S function for robust regression using iteratively reweighted least squares. J. Comp. Graph. Stat. 1, 181–196 (1992)

    Google Scholar 

  20. Hritz, A., Raymond, T., Dutcher, D.: A method for the direct measurement of surface tension of collected atmospherically relevant aerosol particles using atomic force microscopy. Atmos. Chem. Phys. 16, 9761–9769 (2016)

    Article  CAS  Google Scholar 

  21. Huh, C., Mason, S.G.: A rigorous theory of ring tensiometry. Colloid Polym. Sci. 253, 566–580 (1975). https://doi.org/10.1007/bf01753960

    Article  CAS  Google Scholar 

  22. Jacobson, M.C., Hansson, H.C., Noone, K.J., Charlson, R.J.: Organic atmospheric aerosols: review and state of the science. Rev. Geophys. 38(2), 267–294 (2000)

    Article  CAS  Google Scholar 

  23. Jang, M., Kamens, R.M.: Newly characterized products and composition of secondary aerosols from the reaction of \(\upalpha\)-pinene with ozone. Atmos. Environ. 33, 459–474 (1999)

    Article  CAS  Google Scholar 

  24. Jasper, J.: The surface tension of pure liquid compounds. J. Phys. Chem. Ref. Data 1, 841–1009 (1972)

    Article  CAS  Google Scholar 

  25. Jenkin, M.E., Shallcross, D.E., Harvey, J.N.: Development and application of a possible mechanism for the generation of cis-pinic acid from the ozonolysis of \(\upalpha\)- and \(\upbeta\)-pinene. Atmos. Environ. 34, 2837–2850 (2000)

    Article  CAS  Google Scholar 

  26. Kanakidou, M., Seinfeld, J.H., Pandis, S.N., Barnes, I., Dentener, F.J., Facchini, M.C., Dingenen, R.V., Ervens, B., Nenes, A., Nielsen, C.J., Swietlicki, E., Putaud, J.P., Balkanski, Y., Fuzzi, S., Horth, J., Moortgat, G.K., Winterhalter, R., Myhre, C.E.L., Tsigaridis, K., Vignati, E., Stephanou, E.G., Wilson, J.: Organic aerosol and global climate modelling: a review. Atmos. Chem. Phys. 5, 1053–1123 (2005)

    Article  CAS  Google Scholar 

  27. Klamt, A.: Conductor-like screening model for real solvents: a new approach to the quantitative calculation of solvation phenomena. J. Phys. Chem. 99(7), 2224–2235 (1995). https://doi.org/10.1021/j100007a062

    Article  CAS  Google Scholar 

  28. Koch, S., Winterhalter, R., Uherek, E., Kollo, A., Neeb, P., Moortgat, G.K.: Formation of new particles in the gas-phase ozonolysis of monoterpenes. Atmos. Environ. 34, 4031–4042 (2000)

    Article  CAS  Google Scholar 

  29. Kovanic, P., Humber, M.B.: The Economics of Information (Mathematical Gnostics for Data Analysis). https://www.math-gnostics.eu/books/ (2015). Accessed 1 Apr 2019

  30. Landolt-Börnstein: Neue Serie, Band 5, Molekularakustik Temperaturskala von 1990 (1990)

  31. Lim, P.F.C., Liu, X.Y., Kang, L., Ho, P.C.L., Chan, S.Y.: Physicochemical effects of terpenes on organogel for transdermal drug delivery. Int. J. Pharm. 358(1–2), 102–107 (2008)

    Article  CAS  PubMed  Google Scholar 

  32. Lim, P.F.C., Liu, X.Y., Kang, L., Ho, P.C.L., Chan, Y.W., Chan, S.Y.: Limonene GP1/PG organogel as a vehicle in transdermal delivery of haloperidol. Int. J. Pharm. 311(1–2), 157–164 (2006)

    Article  CAS  PubMed  Google Scholar 

  33. NIST WebBook Chemistry: Chloroform. https://webbook.nist.gov/cgi/cbook.cgi?Name=chloroform&Units=SI&cTP=on#Thermo-Phase. Accessed 1 Apr 2019

  34. Nozière, B., Ekström, S., Alsberg, T., Holmström, S.: Radical-initiated formation of organosulfates and surfactants in atmospheric aerosols. Geophys. Res. Lett. 37(5), L05806 (2010). https://doi.org/10.1029/2009GL041683

    Article  CAS  Google Scholar 

  35. Pavlíček, J., Bogdanič, G., Wichterle, I.: Circulation micro-ebulliometer for determination of pressure above mixtures containing solvent and non-volatile component. Fluid Phase Equilib. 297, 142–148 (2010). https://doi.org/10.1016/j.fluid.2010.05.022

    Article  CAS  Google Scholar 

  36. Trujillo-Cayado, L., Ramírez, P., Alfaro, M., Ruíz, M., Muñoz, J.M.: Adsorption at the biocompatible \(\upalpha\)-pinene–water interface and emulsifying properties of two eco-friendly surfactants. Colloids Surf. B 122, 623–629 (2014)

    Article  CAS  Google Scholar 

  37. Štejfa, V., Fulem, M., Růžička, K., Červinka, C., Rocha, M.A.A., Santos, L.M.N.B.F., Schröder, B.: Thermodynamic study of selected monoterpenes. J. Chem. Thermodyn. 60, 117–125 (2013). https://doi.org/10.1016/j.jct.2013.01.009

    Article  CAS  Google Scholar 

  38. Voges, A.B., Stokes, G.Y., Gibbs-Davis, J.M., Lettan, R.B., Bertin, P.A., Pike, R.C., Nguyen, S.T., Scheidt, K.A., Geiger, F.M.: Insights into heterogeneous atmospheric oxidation chemistry: development of a tailor-made synthetic model for studying tropospheric surface chemistry. J. Phys. Chem. C 111(4), 1567–1578 (2007)

    Article  CAS  Google Scholar 

  39. Wagner, W.: New vapour pressure measurements for argon and nitrogen and a new method for establishing rational vapour pressure equations. Cryogenics 13(8), 470–482 (1973). https://doi.org/10.1016/0011-2275(73)90003-9

    Article  CAS  Google Scholar 

  40. Wagner, Z., Bendová, M., Rotrekl, J., Andresová, A., Čanji, M.: Advanced analysis of long time stability of density measurement by vibrating tube density meter. In: 10th World Congress of Chemical Engineering, Book of Abstracts (2017)

  41. Wagner, Z., Bendová, M., Rotrekl, J., Velisek, P., Storch, J., Uchytil, P., Setnickova, K., Reznickova, J.: Advanced analysis of isobaric heat capacities by mathematical gnostics. J. Solution Chem. 46, 1836–1853 (2017). https://doi.org/10.1007/s10953-017-0676-x

    Article  CAS  Google Scholar 

  42. Wagner, Z., Kovanic, P.: Advanced data analysis for industrial applications. Conference Modelling Smart Grids, Prague (2015). https://doi.org/10.13140/RG.2.1.3073.8808

  43. Wang, W., Li, N., Luo, M., Zu, Y., Efferth, T.: Antibacterial activity and anticancer activity of Rosmarinus officinalis l. essential oil compared to that of its main components. Molecules 17, 2704–2713 (2015). https://doi.org/10.3390/molecules17032704

    Article  CAS  Google Scholar 

  44. Wexler, A.: Vapor pressure formulation for water in range 0 to 100 °C. A revision. J. Res. Nat. Bur. Stand. 80A, 775 (1976)

    Article  CAS  Google Scholar 

  45. Zwenger, S., Basu, C.: Plant terpenoids: applications and future potentials. Biotechnol. Mol. Biol. Rev. 3(1), 1–7 (2008)

    Google Scholar 

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Acknowledgements

Financial support of the Czech Science Foundation under Grant Number 17-19798S is acknowledged.

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Wagner, Z., Bendová, M., Rotrekl, J. et al. Densities, Vapor Pressures, and Surface Tensions of Selected Terpenes. J Solution Chem 48, 1147–1166 (2019). https://doi.org/10.1007/s10953-019-00900-3

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