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Insight Into the Formation Paths of Methyl Bromide From Syringic Acid in Aqueous Bromide Solutions Under Simulated Sunlight Irradiation

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  • Hui Liu

    (College of Environmental Science and Engineering, Dalian Maritime University, Dalian 116026, China)

  • Tong Tong

    (College of Environmental Science and Engineering, Dalian Maritime University, Dalian 116026, China)

  • Yingying Pu

    (College of Environmental Science and Engineering, Dalian Maritime University, Dalian 116026, China)

  • Bing Sun

    (College of Environmental Science and Engineering, Dalian Maritime University, Dalian 116026, China)

  • Xiaomei Zhu

    (College of Environmental Science and Engineering, Dalian Maritime University, Dalian 116026, China)

  • Zhiyu Yan

    (College of Environmental Science and Engineering, Dalian Maritime University, Dalian 116026, China)

Abstract

Methyl bromide (CH 3 Br) is one of the largest natural sources of bromine in the stratosphere, where it leads to ozone depletion. This paper reported the photochemical production of CH 3 Br from syringic acid (SA) that has been used as an environmentally relevant model compound for terrestrially-derived dissolved organic matter. The formation of CH 3 Br increased with the increase of bromide ion concentration ranging from 0.8 to 80 mmol L −1 . Ferric ions (Fe(III)) enhanced CH 3 Br production, while chloride inhibited it, with or without Fe(III). Meanwhile, methyl chloride (CH 3 Cl) was generated in the presence of chloride and was inhibited by Fe(III). The different effects of Fe(III) on the formation of CH 3 Cl and CH 3 Br indicate their diverse formation paths. Based on the intermediates identified by liquid chromatography-mass spectrometry and the confirmation of the formation of Fe(III)-SA complexes, it was proposed that there were two formation paths of CH 3 Br from SA in the bromide-enriched water under simulated sunlight irradiation. One path was via nucleophilic attack of Br − on the excited state protonation of SA; the other was via the combination of methyl radical and bromine radical when Fe(III) was present. This work suggests that the photochemical formation of CH 3 Br may act as a potential natural source of CH 3 Br in the bromide-enriched environmental matrix, and helps in better understanding the formation mechanism of CH 3 Br.

Suggested Citation

  • Hui Liu & Tong Tong & Yingying Pu & Bing Sun & Xiaomei Zhu & Zhiyu Yan, 2020. "Insight Into the Formation Paths of Methyl Bromide From Syringic Acid in Aqueous Bromide Solutions Under Simulated Sunlight Irradiation," IJERPH, MDPI, vol. 17(6), pages 1-12, March.
    • Handle: RePEc:gam:jijerp:v:17:y:2020:i:6:p:2081-:d:335126
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    References listed on IDEAS

    as
    1. Hui Liu & Yingying Pu & Tong Tong & Xiaomei Zhu & Bing Sun & Xiaoxing Zhang, 2020. "Photochemical Generation of Methyl Chloride from Humic Aicd: Impacts of Precursor Concentration, Solution pH, Solution Salinity and Ferric Ion," IJERPH, MDPI, vol. 17(2), pages 1-13, January.
    2. F. Keppler & R. Eiden & V. Niedan & J. Pracht & H. F. Schöler, 2000. "Halocarbons produced by natural oxidation processes during degradation of organic matter," Nature, Nature, vol. 403(6767), pages 298-301, January.
    3. Robert C. Rhew & Benjamin R. Miller & Ray F. Weiss, 2000. "Natural methyl bromide and methyl chloride emissions from coastal salt marshes," Nature, Nature, vol. 403(6767), pages 292-295, January.
    4. James H. Butler, 2000. "Better budgets for methyl halides?," Nature, Nature, vol. 403(6767), pages 260-261, January.
    5. Alison Butler & Moriah Sandy, 2009. "Mechanistic considerations of halogenating enzymes," Nature, Nature, vol. 460(7257), pages 848-854, August.
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