Mechanism and kinetic study of the reaction of benzoic acid with OH, NO3 and SO4− radicals in the atmosphere

Zhang, Xianghe; Zhang, Chenxi; Sun, Xiaomin; Yang, Jiaoxue; Zhu, Caixia

doi:10.1039/c9ra02457c

Cited by 14 publications

(5 citation statements)

References 37 publications

(36 reference statements)

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“…Benzoic acid is one of the most common organic acids in the Earth’s atmosphere; it is an important organic aerosol that reacts with OH, NO 3 , and SO 4 radicals in the atmosphere . This simple aromatic acid is a weak acid (p K a = 4.2) with irritating fumes at elevated temperatures.…”

Section: Resultsmentioning

confidence: 99%

Inherently Functionalized Carbon from Algae to Adsorb Precursors of Secondary Organic Aerosols in Noncombustion Sources

Mousavi

Martis

Fini

2021

ACS Sustainable Chem. Eng.

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Recent findings have opened a new window on a hidden source of volatile and semivolatile organic compounds that are released into the atmosphere in the form of gas or aerosol. Asphalt pavement and bituminous composites in general have been found to be noncombustion sources that emit gas-phase precursors of submicron atmospheric aerosols that have serious impacts on human health as well as the climate. This study highlights the merits of using an inherently functionalized carbon (IFC) derived from an algal feedstock to selectively adsorb some potentially hazardous bitumen emissions, alleviating the side effects of intense sun exposure and high temperatures on air quality. With the use of density functional theory (DFT), six organic compounds emitted from bitumen that are precursors to secondary organic aerosols were modeled, then their adsorption to the active zones of a model surface of the IFC containing N-functional groups of amide, amine, pyrrole, and pyridine was measured. In a laboratory experiment, the adsorption properties of the functionalized carbon were also evaluated by a vapor sorption analyzer, supporting the DFT results that indicate the IFC's potential to retain these volatile compounds in the matrix of bitumen. Of the organic molecules studied, benzofuran showed the least interaction with functional groups of the IFC surface (ΔE = −8.3 kcal/mol) and the most total adsorption uptake (2.443 wt %) by the IFC. Dibenzo-thiophene showed the most surface adsorption (ΔE = −18.1 kcal/mol) and the least total adsorption uptake (0.018 wt %) by the IFC. This could be explained by the extent of mobility and penetration of target volatile organic molecules into the IFC's pores. The strong interactions of the IFC's functional groups with organic molecules limit their penetration into the IFC's pores, leading to a decreased total adsorption and vice versa.

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Section: Resultsmentioning

confidence: 99%

Inherently Functionalized Carbon from Algae to Adsorb Precursors of Secondary Organic Aerosols in Noncombustion Sources

Mousavi

Martis

Fini

2021

ACS Sustainable Chem. Eng.

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“…Zhao et al studied the reactive uptake coefficients of NO 3 with four unsaturated fatty acid species using a mixed‐phase relative rates technique [21]. Zhang et al published mechanism and kinetics of the reaction of benzoic acid with NO 3 by quantum chemistry calculations [22]. Acrylic acid would be emitted into atmosphere during the production of floor polish, emulsion polymers, paint formulations, and paper coatings [23].…”

Section: Introductionmentioning

confidence: 99%

Theoretical study of the mechanism and kinetics of the atmospheric reaction of acrylic acid with NO₃ radical

Sun

Xiao

Tang

et al. 2022

Int J of Quantum Chemistry

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The nitrate radical is one of the most significant oxidants in troposphere at the nighttime. Furthermore, acrylic acid is reported to be one of 189 hazardous air pollutants.In order to investigate the atmospheric chemistry and environmental impact of acrylic acid with nitrate radical, in this work, the atmospheric reaction mechanisms of acrylic acid by NO 3 radical have been discussed by the CCSD(T)/cc-pVTZ// M06-2X/6-311++G(d, p) dual-level of theory at the first time. The energy barriers of NO 3 and CH 2 CHCOOH reaction have also been calculated accurately. The additions between NO 3 with CH 2 CHCOOH would produce the dominant intermediates CH 2 NO 3 CHCOOH and CH 2 CHNO 3 COOH via low barriers. All hydrogen abstraction channels have higher barriers than that of additions. Therefore, addition pathways play an important role in this reaction. The total and branching rate constants have been computed by conventional transition state theory via the Variflex code. These rate constants of NO 3 and acrylic acid reaction would be useful to complete structure-activity relationships of reaction rate. The calculated atmospheric lifetime of acrylic acid by NO 3 is about 3.66 days at night. All findings will help us gain a better understanding of atmospheric chemistry of acrylic acid.

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“…The environmental chemistry of aromatic substances is of great importance because they influence Earth’s carbon cycle. − Among the variety of species associated with hydrocarbon transformation, nitrite has been intensively highlighted owing to its importance in photochemistry as a source of nitric oxide and hydroxyl radicals, as well as its inherent reactivity when protonated to form nitrous acid. − Generally, most studies on nitrite chemistry have focused on aqueous and gaseous phase reactions. However, its unique behavior during freezing has also been identified and analyzed. − This unique behavior is the significant acceleration of the reaction during freezing compared with the liquid phase when the pH is ∼4. , …”

Section: Introductionmentioning

confidence: 99%

“…In this study, we propose a novel chemical reaction mechanism, i.e., the accelerated oxidation of aromatic substances in the frozen hydrogen peroxide and nitrite solution. We tested the oxidation of benzoic acid (BA) as a representative aromatic compound because its structure is ubiquitous in various organic compounds in the environment and drugs, and it resists the oxidative attack of HONO, as shown in our experiment. This negligible reactivity is important because many studies on aromatic nitration have discussed nitration-prone compounds, such as phenol, to analyze the role of nitrous acid. ,,,, However, we also need to consider nitration-resistant compounds under certain conditions.…”

Section: Introductionmentioning

confidence: 99%

Frozen Hydrogen Peroxide and Nitrite Solution: The Acceleration of Benzoic Acid Oxidation via the Decreased pH in Ice

Ahn

Kim

2021

Environ. Sci. Technol.

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We investigated benzoic acid oxidation via the reaction of hydrogen peroxide (H2O2) and nitrite (NO2 –). The oxidation of benzoic acid by reactive nitrous acid (HONO) was negligible, and the reactivity of the H2O2/NO2 – system decreased with a decrease in temperature under aqueous conditions. However, freezing markedly accelerated the chemical reaction. Based on Raman microscope measurements, concentrated species were confirmed in certain regions of the ice. We proposed that the change in nitrite speciation (accordingly, a decrease in the pH below pK a), derived from the freezing concentration effect, was the reason for the accelerated reactions. The oxidation characteristics of the system were monitored under varying conditions, such as initial pH, dosage ratio, benzoic acid concentration, and reaction with various benzene derivatives. The ultrahigh-performance liquid chromatography/electrospray ionization/mass spectrometry (UHPLC/ESI/MS) measurement showed that peroxynitrous acid (HOONO)-mediated oxidation generated hydroxylated and nitrated byproducts. Additionally, decarboxylated products were detected, indicating direct electron transfer from the organic compounds to HOONO. As freezing is a global phenomenon, and H2O2 and NO2 – are ubiquitous in the environment, the transformation of aromatic compounds with H2O2/NO2 – in cold environments must be considered in environmental chemistry.

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Mechanism and kinetic study of the reaction of benzoic acid with OH, NO₃ and SO₄⁻ radicals in the atmosphere

Abstract: We present a study of benzoic acid with OH, NO3 and SO4− radicals in the atmospheric environment.

Cited by 14 publications

References 37 publications

Inherently Functionalized Carbon from Algae to Adsorb Precursors of Secondary Organic Aerosols in Noncombustion Sources

Inherently Functionalized Carbon from Algae to Adsorb Precursors of Secondary Organic Aerosols in Noncombustion Sources

Theoretical study of the mechanism and kinetics of the atmospheric reaction of acrylic acid with NO₃ radical

Frozen Hydrogen Peroxide and Nitrite Solution: The Acceleration of Benzoic Acid Oxidation via the Decreased pH in Ice

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Mechanism and kinetic study of the reaction of benzoic acid with OH, NO3 and SO4− radicals in the atmosphere

Abstract: We present a study of benzoic acid with OH, NO3 and SO4− radicals in the atmospheric environment.

Cited by 14 publications

References 37 publications

Inherently Functionalized Carbon from Algae to Adsorb Precursors of Secondary Organic Aerosols in Noncombustion Sources

Inherently Functionalized Carbon from Algae to Adsorb Precursors of Secondary Organic Aerosols in Noncombustion Sources

Theoretical study of the mechanism and kinetics of the atmospheric reaction of acrylic acid with NO3 radical

Frozen Hydrogen Peroxide and Nitrite Solution: The Acceleration of Benzoic Acid Oxidation via the Decreased pH in Ice

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Mechanism and kinetic study of the reaction of benzoic acid with OH, NO₃ and SO₄⁻ radicals in the atmosphere

Theoretical study of the mechanism and kinetics of the atmospheric reaction of acrylic acid with NO₃ radical