Single-particle experiments measuring humidity and inorganic salt effects on gas-particle partitioning of butenedial

Birdsall, Adam W.; Hensley, Jack C.; Kotowitz, Paige S.; Huisman, Andrew J.; Keutsch, Frank N.

doi:10.5194/acp-19-14195-2019

Cited by 12 publications

(37 citation statements)

References 39 publications

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“…0.55 M butenedial in D2O solution and a six-fold dilution of this solution, resulting in 0.09 M butenedial in D2O, were studied with NMR under acidic conditions. In both solutions, butenedial strongly favored the dihydrate form with only minimal formation of acetal oligomers (see Supplement Section 2, Figure S2 and Table S2), as shown previously (Birdsall et al, 2019).…”

Section: Butenedial In Aqueous Solutions Without Nhxsupporting

confidence: 84%

“…As butenedial is an electron-poor dialdehyde, its chemical reactivity is expected to be more similar to that of glyoxal than methylglyoxal or biacetyl. However, we have shown in a past study that butenedial acetal oligomers are insignificant in water and that it salts out in the presence of anions, behavior that is unlike that of glyoxal and more similar to methylglyoxal (Birdsall et al, 2019).…”

mentioning

confidence: 62%

“…As discussed in a previous study, like glyoxal, the hydration equilibrium of butenedial is strongly shifted toward the dihydrate (>95% of the total butenedial on a molar basis). Birdsall et al (2019) also showed that the ratio of unhydrated or monohydrated to dihydrated butenedial appeared to be unaffected by the availability of water. It is expected that the hydration behavior of butenedial will affect its reactivity, and possibly differentiate it from glyoxal, which has been observed to form a…”

Section: Chemical Schemementioning

confidence: 93%

“…All chemicals were obtained from Sigma Aldrich unless otherwise specified. The synthesis of butenedial is described elsewhere in greater detail (Avenati and Vogel, 1982;Birdsall et al, 2019). Mixtures containing 2.4 M 2,5-dihydro 2,5dimethoxyfuran (TCI America, 98%) and 3.4 M glacial acetic acid (HAc, VWR, 99.7%) were prepared.…”

Section: Materials and Instrumentsmentioning

confidence: 99%

“…10-20% w/w hexaethylene glycol (PEG-6, 99%) was used as an internal standard for MS measurements, as done previously (Birdsall et al, 2018). Previous work demonstrated there is no reaction between butenedial and PEG-6 (Birdsall et al, 2019). Distilled H2O was the solvent for all MS experiments.…”

Section: Materials and Instrumentsmentioning

confidence: 99%

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Revisiting the reaction of dicarbonyls in aerosol proxy solutions containing ammonia: the case of butenedial

Hensley¹,

Birdsall²,

Valtierra³

et al. 2021

Preprint

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Abstract. Reactions in aqueous solutions containing dicarbonyls (especially the α-dicarbonyls methylglyoxal, glyoxal, and biacetyl) and reduced nitrogen (NHx) have been studied extensively. It has been proposed that accretion reactions from dicarbonyls and NHx could be a source of particulate matter and brown carbon in the atmosphere and therefore have direct implications for human health and climate. Other dicarbonyls, such as the 1,4-unsaturated dialdehyde butenedial, are also produced from the atmospheric oxidation of volatile organic compounds, especially aromatics and furans, but their aqueous phase reactions with NHx have not been characterized. In this work, we determine a pH-dependent mechanism of butenedial reactions in aqueous solutions with NHx that is compared to α-dicarbonyls, in particular the dialdehyde glyoxal. Similar to glyoxal, butenedial is strongly hydrated in aqueous solutions. Butenedial reaction with NHx also produces nitrogen-containing rings and leads to accretion reactions that form brown carbon. Despite glyoxal and butenedial both being dialdehydes, butenedial is observed to have three significant differences in its chemical behavior: (1) as previously shown, butenedial does not substantially form acetal oligomers, (2) the butenedial/OH− reaction leads to light-absorbing compounds, and (3) the butenedial/NHx reaction is fast and first order in the dialdehyde. Building off of a complementary study on butenedial gas-particle partitioning, we suggest that the behavior of other reactive dialdehydes and dicarbonyls may not always be adequately predicted by α-dicarbonyls, even though their dominant functionalities are closely related. The carbon skeleton (e.g., its hydrophobicity, length, and bond structure) also governs the fate and climate-relevant properties of dicarbonyls in the atmosphere. If other dicarbonyls behave like butenedial, their reaction with NHx could constitute a regional source of brown carbon to the atmosphere.

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Section: Butenedial In Aqueous Solutions Without Nhxsupporting

confidence: 84%

mentioning

confidence: 62%

Section: Chemical Schemementioning

confidence: 93%

Section: Materials and Instrumentsmentioning

confidence: 99%

Section: Materials and Instrumentsmentioning

confidence: 99%

See 3 more Smart Citations

Revisiting the reaction of dicarbonyls in aerosol proxy solutions containing ammonia: the case of butenedial

Hensley¹,

Birdsall²,

Valtierra³

et al. 2021

Preprint

Self Cite

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Online headspace monitoring of volatile organic compounds using proton transfer reaction-mass spectrometry: Application to the multiphase atmospheric fate of 2,4-hexadienedial

Brun,

González-Sánchez,

Ravier

et al. 2024

Talanta

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Multiphase Atmospheric Chemistry in Liquid Water: Impacts and Controllability of Organic Aerosol

et al. 2020

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Conspectus Liquid water is a dominant and critical tropospheric constituent. Over polluted land masses low level cumulus clouds interact with boundary layer aerosol. The planetary boundary layer (PBL) is the lowest atmospheric layer and is directly influenced by Earth’s surface. Water–aerosol interactions are critical to processes that govern the fate and transport of trace species in the Earth system and their impacts on air quality, radiative forcing, and regional hydrological cycling. In the PBL, air parcels rise adiabatically from the surface, and anthropogenically influenced hygroscopic aerosols take up water and serve as cloud condensation nuclei (CCN) to form clouds. Water-soluble gases partition to liquid water in wet aerosols and cloud droplets and undergo aqueous-phase photochemistry. Most cloud droplets evaporate, and low volatility material formed during aqueous phase chemistry remains in the condensed phase and adds to aerosol mass. The resulting cloud-processed aerosol has different physicochemical properties compared to the original CCN. Organic species that undergo multiphase chemistry in atmospheric liquid water transform gases to highly concentrated, nonideal ionic aqueous solutions and form secondary organic aerosol (SOA). In recent years, SOA formation modulated by atmospheric waters has received considerable interest. Key uncertainties are related to the chemical nature of hygroscopic aerosols that become CCN and their interaction with organic species. Gas-to-droplet or gas-to-aqueous aerosol partitioning of organic compounds is affected by the intrinsic chemical properties of the organic species in addition to the pre-existing condensed phase. Environmentally relevant conditions for atmospheric aerosol are nonideal. Salt identity and concentration, in addition to aerosol phase state, can dramatically affect organic gas miscibility for many compounds, in particular when ionic strength and salt molality are outside the bounds of limiting laws. For example, Henry’s law and Debye–Hückel theory are valid only for dilute aqueous systems uncharacteristic of real atmospheric conditions. Chemical theory is incomplete, and at ambient conditions, this chemistry plays a determining role in total aerosol mass and particle size, controlling factors for air quality and climate-relevant aerosol properties. Accurate predictive skill to understand the impacts of societal choices and policies on air quality and climate requires that models contain correct chemical mechanisms and appropriate feedbacks. Globally, SOA is a dominant contributor to the atmospheric organic aerosol burden, and most mass can be traced back to precursor gas-phase volatile organic compounds (VOCs) emitted from the biosphere. However, organic aerosol concentrations in the Amazon Rainforest, the largest emitter of biogenic VOCs, are generally lower than in U.S. national parks. The Interagency Monitoring of Protected Visual Environments (IMPROVE) air quality network, with sites located predominantly in national parks, provides the longest...

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Single-particle experiments measuring humidity and inorganic salt effects on gas-particle partitioning of butenedial

Cited by 12 publications

References 39 publications

Revisiting the reaction of dicarbonyls in aerosol proxy solutions containing ammonia: the case of butenedial

Revisiting the reaction of dicarbonyls in aerosol proxy solutions containing ammonia: the case of butenedial

Online headspace monitoring of volatile organic compounds using proton transfer reaction-mass spectrometry: Application to the multiphase atmospheric fate of 2,4-hexadienedial

Multiphase Atmospheric Chemistry in Liquid Water: Impacts and Controllability of Organic Aerosol

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