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Henry's Law Constants of Some β-, γ-, and δ-Hydroxy Alkyl Nitrates of Atmospheric Interest

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    Article

    Henry's Law Constants of Some β-, γ-, and δ-Hydroxy Alkyl Nitrates of Atmospheric Interest
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    Department of Environmental Sciences, Weizmann Institute, Rehovot 76100, Israel
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    Environmental Science & Technology

    Cite this: Environ. Sci. Technol. 2000, 34, 7, 1197–1203
    Click to copy citationCitation copied!
    https://doi.org/10.1021/es990558a
    Published February 19, 2000
    Copyright © 2000 American Chemical Society
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    Abstract

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    Organic nitrates form via the photodegradation of hydrocarbons in the troposphere in the presence of NO and NO2. This process competes with the chemical cycle leading to ozone production since it sequesters both nitrogen oxides and organic radicals. Hydroxy nitrates form via the atmospheric reactions of alkanes and alkenes and are thought to be an important nitrogen oxides reservoir. In this study, new synthetic methods to produce β-, γ-, and δ-hydroxy nitrates of atmospheric interest were developed. NMR and IR spectroscopies were used to characterize these compounds. Henry's law coefficients of C4 and C5 hydroxy nitrates at 291 ± 2 K were measured using a dynamic equilibrium system. The solubility decreases with the organic chain length and increases with increasing distance between the nitrooxy and hydroxy groups. Due to their large Henry's law coefficients these species will partition into droplets in the presence of clouds and fogs. Measurements of the OH reaction and photolysis rate coefficients are needed for an accurate assessment of the atmospheric lifetimes of these compounds.

    Copyright © 2000 American Chemical Society

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     Corresponding author phone:  972-8-934-4237; fax:  972-8-934-4124; e-mail:  [email protected].

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    4. Geoffrey K. Yeh, Megan S. Claflin, and Paul J. Ziemann . Products and Mechanism of the Reaction of 1-Pentadecene with NO3 Radicals and the Effect of a −ONO2 Group on Alkoxy Radical Decomposition. The Journal of Physical Chemistry A 2015, 119 (43) , 10684-10696. https://doi.org/10.1021/acs.jpca.5b07468
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    6. A. E. Perring, S. E. Pusede, and R. C. Cohen . An Observational Perspective on the Atmospheric Impacts of Alkyl and Multifunctional Nitrates on Ozone and Secondary Organic Aerosol. Chemical Reviews 2013, 113 (8) , 5848-5870. https://doi.org/10.1021/cr300520x
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    Cite this: Environ. Sci. Technol. 2000, 34, 7, 1197–1203
    Click to copy citationCitation copied!
    https://doi.org/10.1021/es990558a
    Published February 19, 2000
    Copyright © 2000 American Chemical Society
    Request reuse permissions

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