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Henry's Law Constants

www.henrys-law.org

Rolf Sander

Atmospheric Chemistry Division

Max-Planck Institute for Chemistry
Mainz, Germany

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Henry's Law Constants

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When referring to the compilation of Henry's Law Constants, please cite this publication:

R. Sander: Compilation of Henry's law constants (version 5.0.0) for water as solvent, Atmos. Chem. Phys., 23, 10901-12440 (2023), doi:10.5194/acp-23-10901-2023

The publication from 2023 replaces that from 2015, which is now obsolete. Please do not cite the old paper anymore.

Henry's Law Constants → Organic species with oxygen (O) → Esters (RCOOR) → methyl ethanoate

FORMULA:CH3COOCH3
TRIVIAL NAME: methyl acetate
CAS RN:79-20-9
STRUCTURE
(FROM NIST):
InChIKey:KXKVLQRXCPHEJC-UHFFFAOYSA-N

Hscp d ln Hs cp / d (1/T) References Type Notes
[mol/(m3Pa)] [K]
8.5×10−2 5900 Burkholder et al. (2019) L 1) 500)
2.0×10−2 5000 Burkholder et al. (2015) L 501) 502)
8.5×10−2 5900 Brockbank (2013) L 1)
8.1×10−2 4800 Plyasunov et al. (2004) L
8.1×10−2 4900 Fenclová et al. (2014) M 1)
1.2×10−1 7500 Hiatt (2013) M
6.6×10−2 4500 Arp and Schmidt (2004) M
8.3×10−2 4900 Hovorka et al. (2002) M
4.2×10−2 Kaneko et al. (1994) M 14)
7.7×10−2 Ioffe et al. (1984) M
7.7×10−2 5000 Kieckbusch and King (1979b) M 503)
8.6×10−2 Buttery et al. (1969) M
1.1×10−1 Butler and Ramchandani (1935) M
8.7×10−2 4800 McKeown and Stowell (1927) M
1.1×10−1 Mackay et al. (2006c) V
1.1×10−1 Mackay et al. (1995) V
4.8×10−2 3300 Djerki and Laub (1988) V
1.1×10−1 4800 Bagno et al. (1991) T 475)
1.8×10−1 Yaws (2003) X 259)
9.6×10−2 Dupeux et al. (2022) Q 260)
1.6×10−2 Keshavarz et al. (2022) Q
1.7×10−1 Duchowicz et al. (2020) Q
3.4×10−2 Wang et al. (2017) Q 81) 239)
1.2×10−1 Wang et al. (2017) Q 81) 240)
2.5×10−1 Wang et al. (2017) Q 81) 241)
7.3×10−2 Li et al. (2014) Q 242)
7.8×10−2 Raventos-Duran et al. (2010) Q 244) 272)
7.8×10−2 Raventos-Duran et al. (2010) Q 245)
6.2×10−2 Raventos-Duran et al. (2010) Q 246)
6.4×10−2 Hilal et al. (2008) Q
6.0×10−2 Modarresi et al. (2007) Q 68)
4500 Kühne et al. (2005) Q
8.6×10−2 Yaffe et al. (2003) Q 249) 250)
5.4×10−2 Yao et al. (2002) Q 230)
7.0×10−2 English and Carroll (2001) Q 231) 232)
3.8×10−2 Katritzky et al. (1998) Q
5.6×10−2 Suzuki et al. (1992) Q 233)
3.9×10−2 Nirmalakhandan and Speece (1988) Q
8.6×10−2 Duchowicz et al. (2020) ? 21) 186)
4900 Kühne et al. (2005) ?
1.4×10−1 Yaws (1999) ? 12) 21)
8.0×10−2 Abraham et al. (1990) ?

Data

The first column contains Henry's law solubility constant Hscp at the reference temperature of 298.15 K.
The second column contains the temperature dependence d ln Hs cp / d (1/T), also at the reference temperature.

References

  • Abraham, M. H., Whiting, G. S., Fuchs, R., & Chambers, E. J.: Thermodynamics of solute transfer from water to hexadecane, J. Chem. Soc. Perkin Trans. 2, pp. 291–300, doi:10.1039/P29900000291 (1990).
  • Arp, H. P. H. & Schmidt, T. C.: Air–water transfer of MTBE, its degradation products, and alternative fuel oxygenates: the role of temperature, Environ. Sci. Technol., 38, 5405–5412, doi:10.1021/ES049286O (2004).
  • Bagno, A., Lucchini, V., & Scorrano, G.: Thermodynamics of protonation of ketones and esters and energies of hydration of their conjugate acids, J. Phys. Chem., 95, 345–352, doi:10.1021/J100154A063 (1991).
  • Brockbank, S. A.: Aqueous Henry’s law constants, infinite dilution activity coefficients, and water solubility: critically evaluated database, experimental analysis, and prediction methods, Ph.D. thesis, Brigham Young University, USA, URL https://scholarsarchive.byu.edu/etd/3691/ (2013).
  • Burkholder, J. B., Sander, S. P., Abbatt, J., Barker, J. R., Huie, R. E., Kolb, C. E., Kurylo, M. J., Orkin, V. L., Wilmouth, D. M., & Wine, P. H.: Chemical Kinetics and Photochemical Data for Use in Atmospheric Studies, Evaluation No. 18, JPL Publication 15-10, Jet Propulsion Laboratory, Pasadena, URL https://jpldataeval.jpl.nasa.gov (2015).
  • Burkholder, J. B., Sander, S. P., Abbatt, J., Barker, J. R., Cappa, C., Crounse, J. D., Dibble, T. S., Huie, R. E., Kolb, C. E., Kurylo, M. J., Orkin, V. L., Percival, C. J., Wilmouth, D. M., & Wine, P. H.: Chemical Kinetics and Photochemical Data for Use in Atmospheric Studies, Evaluation No. 19, JPL Publication 19-5, Jet Propulsion Laboratory, Pasadena, URL https://jpldataeval.jpl.nasa.gov (2019).
  • Butler, J. A. V. & Ramchandani, C. N.: The solubility of non-electrolytes. Part II. The influence of the polar group on the free energy of hydration of aliphatic compounds, J. Chem. Soc., pp. 952–955, doi:10.1039/JR9350000952 (1935).
  • Buttery, R. G., Ling, L. C., & Guadagni, D. G.: Volatilities of aldehydes, ketones, and esters in dilute water solutions, J. Agric. Food Chem., 17, 385–389, doi:10.1021/JF60162A025 (1969).
  • Djerki, R. A. & Laub, R. J.: Solute retention in column liquid chromatography. X. Determination of solute infinite-dilution activity coefficients in methanol, water, and their mixtures, by combined gas-liquid and liquid-liquid chromatography, J. Liq. Chromatogr., 11, 585–612, doi:10.1080/01483918808068333 (1988).
  • Duchowicz, P. R., Aranda, J. F., Bacelo, D. E., & Fioressi, S. E.: QSPR study of the Henry’s law constant for heterogeneous compounds, Chem. Eng. Res. Des., 154, 115–121, doi:10.1016/J.CHERD.2019.12.009 (2020).
  • Dupeux, T., Gaudin, T., Marteau-Roussy, C., Aubry, J.-M., & Nardello-Rataj, V.: COSMO-RS as an effective tool for predicting the physicochemical properties of fragrance raw materials, Flavour Fragrance J., 37, 106–120, doi:10.1002/FFJ.3690 (2022).
  • English, N. J. & Carroll, D. G.: Prediction of Henry’s law constants by a quantitative structure property relationship and neural networks, J. Chem. Inf. Comput. Sci., 41, 1150–1161, doi:10.1021/CI010361D (2001).
  • Fenclová, D., Blahut, A., Vrbka, P., Dohnal, V., & Böhme, A.: Temperature dependence of limiting activity coefficients, Henry’s law constants, and related infinite dilution properties of C4-C6 isomeric n-alkyl ethanoates/ethyl n-alkanoates in water. Measurement, critical compilation, correlation, and recommended data, Fluid Phase Equilib., 375, 347–359, doi:10.1016/J.FLUID.2014.05.023 (2014).
  • Hiatt, M. H.: Determination of Henry’s law constants using internal standards with benchmark values, J. Chem. Eng. Data, 58, 902–908, doi:10.1021/JE3010535 (2013).
  • Hilal, S. H., Ayyampalayam, S. N., & Carreira, L. A.: Air-liquid partition coefficient for a diverse set of organic compounds: Henry’s law constant in water and hexadecane, Environ. Sci. Technol., 42, 9231–9236, doi:10.1021/ES8005783 (2008).
  • Hovorka, Š., Dohnal, V., Roux, A. H., & Roux-Desgranges, G.: Determination of temperature dependence of limiting activity coefficients for a group of moderately hydrophobic organic solutes in water, Fluid Phase Equilib., 201, 135–164, doi:10.1016/S0378-3812(02)00087-0 (2002).
  • Ioffe, B. V., Kostkina, M. I., & Vitenberg, A. G.: Preparation of standard vapor-gas mixtures for gas chromatography: discontinuous gas extraction, Anal. Chem., 56, 2500–2503, doi:10.1021/AC00277A053 (1984).
  • Kaneko, T., Wang, P. Y., & Sato, A.: Partition coefficients of some acetate esters and alcohols in water, blood, olive oil, and rat tissues, Occup. Environ. Med., 51, 68–72, doi:10.1136/OEM.51.1.68 (1994).
  • Katritzky, A. R., Wang, Y., Sild, S., Tamm, T., & Karelson, M.: QSPR studies on vapor pressure, aqueous solubility, and the prediction of water-air partition coefficients, J. Chem. Inf. Comput. Sci., 38, 720–725, doi:10.1021/CI980022T (1998).
  • Keshavarz, M. H., Rezaei, M., & Hosseini, S. H.: A simple approach for prediction of Henry’s law constant of pesticides, solvents, aromatic hydrocarbons, and persistent pollutants without using complex computer codes and descriptors, Process Saf. Environ. Prot., 162, 867–877, doi:10.1016/J.PSEP.2022.04.045 (2022).
  • Kieckbusch, T. G. & King, C. J.: An improved method of determining vapor liquid equilibria for dilute organics in aqueous solution, J. Chromatogr. Sci., 17, 273–276, doi:10.1093/CHROMSCI/17.5.273 (1979b).
  • Kühne, R., Ebert, R.-U., & Schüürmann, G.: Prediction of the temperature dependency of Henry’s law constant from chemical structure, Environ. Sci. Technol., 39, 6705–6711, doi:10.1021/ES050527H (2005).
  • Li, H., Wang, X., Yi, T., Xu, Z., & Liu, X.: Prediction of Henry’s law constants for organic compounds using multilayer feedforward neural networks based on linear salvation energy relationship, J. Chem. Pharm. Res., 6, 1557–1564 (2014).
  • Mackay, D., Shiu, W. Y., & Ma, K. C.: Illustrated Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals, vol. IV of Oxygen, Nitrogen, and Sulfur Containing Compounds, Lewis Publishers, Boca Raton, ISBN 1566700353 (1995).
  • Mackay, D., Shiu, W. Y., Ma, K. C., & Lee, S. C.: Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals, vol. III of Oxygen Containing Compounds, CRC/Taylor & Francis Group, doi:10.1201/9781420044393 (2006c).
  • McKeown, A. & Stowell, F. P.: XVI.—The vapour pressures of mixtures of (a) methyl acetate and water ; (b) methyl acetate, sucrose, and water, J. Chem. Soc., pp. 97–103, doi:10.1039/JR9270000097 (1927).
  • Modarresi, H., Modarress, H., & Dearden, J. C.: QSPR model of Henry’s law constant for a diverse set of organic chemicals based on genetic algorithm-radial basis function network approach, Chemosphere, 66, 2067–2076, doi:10.1016/J.CHEMOSPHERE.2006.09.049 (2007).
  • Nirmalakhandan, N. N. & Speece, R. E.: QSAR model for predicting Henry’s constant, Environ. Sci. Technol., 22, 1349–1357, doi:10.1021/ES00176A016 (1988).
  • Plyasunov, A. V., Plyasunova, N. V., & Shock, E. L.: Group contribution values for the thermodynamic functions of hydration of aliphatic esters at 298.15 K, 0.1 MPa, J. Chem. Eng. Data, 49, 1152–1167, doi:10.1021/JE049850A (2004).
  • Raventos-Duran, T., Camredon, M., Valorso, R., Mouchel-Vallon, C., & Aumont, B.: Structure-activity relationships to estimate the effective Henry’s law constants of organics of atmospheric interest, Atmos. Chem. Phys., 10, 7643–7654, doi:10.5194/ACP-10-7643-2010 (2010).
  • Suzuki, T., Ohtaguchi, K., & Koide, K.: Application of principal components analysis to calculate Henry’s constant from molecular structure, Comput. Chem., 16, 41–52, doi:10.1016/0097-8485(92)85007-L (1992).
  • Wang, C., Yuan, T., Wood, S. A., Goss, K.-U., Li, J., Ying, Q., & Wania, F.: Uncertain Henry’s law constants compromise equilibrium partitioning calculations of atmospheric oxidation products, Atmos. Chem. Phys., 17, 7529–7540, doi:10.5194/ACP-17-7529-2017 (2017).
  • Yaffe, D., Cohen, Y., Espinosa, G., Arenas, A., & Giralt, F.: A fuzzy ARTMAP-based quantitative structure-property relationship (QSPR) for the Henry’s law constant of organic compounds, J. Chem. Inf. Comput. Sci., 43, 85–112, doi:10.1021/CI025561J (2003).
  • Yao, X., aand X. Zhang, M. L., Hu, Z., & Fan, B.: Radial basis function network-based quantitative structure-property relationship for the prediction of Henry’s law constant, Anal. Chim. Acta, 462, 101–117, doi:10.1016/S0003-2670(02)00273-8 (2002).
  • Yaws, C. L.: Chemical Properties Handbook, McGraw-Hill, Inc., ISBN 0070734011 (1999).
  • Yaws, C. L.: Yaws’ Handbook of Thermodynamic and Physical Properties of Chemical Compounds, Knovel: Norwich, NY, USA, ISBN 1591244447 (2003).

Type

Table entries are sorted according to reliability of the data, listing the most reliable type first: L) literature review, M) measured, V) VP/AS = vapor pressure/aqueous solubility, R) recalculation, T) thermodynamical calculation, X) original paper not available, C) citation, Q) QSPR, E) estimate, ?) unknown, W) wrong. See Section 3.1 of Sander (2023) for further details.

Notes

1) A detailed temperature dependence with more than one parameter is available in the original publication. Here, only the temperature dependence at 298.15 K according to the van 't Hoff equation is presented.
12) Value at T = 293 K.
14) Value at T = 310 K.
21) Several references are given in the list of Henry's law constants but not assigned to specific species.
68) Modarresi et al. (2007) use different descriptors for their calculations. They conclude that a genetic algorithm/radial basis function network (GA/RBFN) is the best QSPR model. Only these results are shown here.
81) Value at T = 288 K.
186) Experimental value, extracted from HENRYWIN.
230) Yao et al. (2002) compared two QSPR methods and found that radial basis function networks (RBFNs) are better than multiple linear regression. In their paper, they provide neither a definition nor the unit of their Henry's law constants. Comparing the values with those that they cite from Yaws (1999), it is assumed that they use the variant Hvpx and the unit atm.
231) English and Carroll (2001) provide several calculations. Here, the preferred value with explicit inclusion of hydrogen bonding parameters from a neural network is shown.
232) Value from the training dataset.
233) Calculated with a principal component analysis (PCA); see Suzuki et al. (1992) for details.
239) Calculated using linear free energy relationships (LFERs).
240) Calculated using SPARC Performs Automated Reasoning in Chemistry (SPARC).
241) Calculated using COSMOtherm.
242) Temperature is not specified.
244) Calculated using the GROMHE model.
245) Calculated using the SPARC approach.
246) Calculated using the HENRYWIN method.
249) Yaffe et al. (2003) present QSPR results calculated with the fuzzy ARTMAP (FAM) and with the back-propagation (BK-Pr) method. They conclude that FAM is better. Only the FAM results are shown here.
250) Value from the training set.
259) Value given here as quoted by Dupeux et al. (2022).
260) Calculated using the COSMO-RS method.
272) Value from the validation dataset.
475) Calculated under the assumption that ∆G and ∆H are based on [mol L−1] and [atm] as the standard states.
500) The H298 and A, B, C data listed in Table 5-4 of Burkholder et al. (2019) are inconsistent, with 6 % difference.
501) The formula of methyl ethanoate is incorrectly given as "CH3C(O)CH3" by Burkholder et al. (2015).
502) The H298 and A, B data listed in Table 5-4 of Burkholder et al. (2015) are inconsistent, with 74 % difference.
503) The same data were also published in Kieckbusch and King (1979a).

The numbers of the notes are the same as in Sander (2023). References cited in the notes can be found here.

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