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Kinetics, Products, and Brown Carbon Formation by Aqueous-Phase Reactions of Glycolaldehyde with Atmospheric Amines and Ammonium Sulfate
[Image: see text] Glycolaldehyde (GAld) is a C(2) water-soluble aldehyde produced during the atmospheric oxidation of isoprene and many other species and is commonly found in cloudwater. Previous work has established that glycolaldehyde evaporates more readily from drying aerosol droplets containing...
Autores principales: | , , , , , , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9393862/ https://www.ncbi.nlm.nih.gov/pubmed/35925760 http://dx.doi.org/10.1021/acs.jpca.2c02606 |
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author | Rodriguez, Alyssa A. Rafla, Michael A. Welsh, Hannah G. Pennington, Elyse A. Casar, Jason R. Hawkins, Lelia N. Jimenez, Natalie G. de Loera, Alexia Stewart, Devoun R. Rojas, Antonio Tran, Matthew-Khoa Lin, Peng Laskin, Alexander Formenti, Paola Cazaunau, Mathieu Pangui, Edouard Doussin, Jean-François De Haan, David O. |
author_facet | Rodriguez, Alyssa A. Rafla, Michael A. Welsh, Hannah G. Pennington, Elyse A. Casar, Jason R. Hawkins, Lelia N. Jimenez, Natalie G. de Loera, Alexia Stewart, Devoun R. Rojas, Antonio Tran, Matthew-Khoa Lin, Peng Laskin, Alexander Formenti, Paola Cazaunau, Mathieu Pangui, Edouard Doussin, Jean-François De Haan, David O. |
author_sort | Rodriguez, Alyssa A. |
collection | PubMed |
description | [Image: see text] Glycolaldehyde (GAld) is a C(2) water-soluble aldehyde produced during the atmospheric oxidation of isoprene and many other species and is commonly found in cloudwater. Previous work has established that glycolaldehyde evaporates more readily from drying aerosol droplets containing ammonium sulfate (AS) than does glyoxal, methylglyoxal, or hydroxyacetone, which implies that it does not oligomerize as quickly as these other species. Here, we report NMR measurements of glycolaldehyde’s aqueous-phase reactions with AS, methylamine, and glycine. Reaction rate constants are smaller than those of respective glyoxal and methylglyoxal reactions in the pH range of 3–6. In follow-up cloud chamber experiments, deliquesced glycine and AS seed particles were found to take up glycolaldehyde and methylamine and form brown carbon. At very high relative humidity, these changes were more than 2 orders of magnitude faster than predicted by our bulk liquid NMR kinetics measurements, suggesting that reactions involving surface-active species at crowded air–water interfaces may play an important role. The high-resolution liquid chromatography–electrospray ionization–mass spectrometric analysis of filter extracts of unprocessed AS + GAld seed particles identified sugar-like C(6) and C(12) GAld oligomers, including proposed product 3-deoxyglucosone, with and without modification by reactions with ammonia to diimine and imidazole forms. Chamber exposure to methylamine gas, cloud processing, and simulated sunlight increased the incorporation of both ammonia and methylamine into oligomers. Many C(4)–C(16) imidazole derivatives were detected in an extract of chamber-exposed aerosol along with a predominance of N-derivatized C(6) and C(12) glycolaldehyde oligomers, suggesting that GAld is capable of forming brown carbon SOA. |
format | Online Article Text |
id | pubmed-9393862 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-93938622022-08-23 Kinetics, Products, and Brown Carbon Formation by Aqueous-Phase Reactions of Glycolaldehyde with Atmospheric Amines and Ammonium Sulfate Rodriguez, Alyssa A. Rafla, Michael A. Welsh, Hannah G. Pennington, Elyse A. Casar, Jason R. Hawkins, Lelia N. Jimenez, Natalie G. de Loera, Alexia Stewart, Devoun R. Rojas, Antonio Tran, Matthew-Khoa Lin, Peng Laskin, Alexander Formenti, Paola Cazaunau, Mathieu Pangui, Edouard Doussin, Jean-François De Haan, David O. J Phys Chem A [Image: see text] Glycolaldehyde (GAld) is a C(2) water-soluble aldehyde produced during the atmospheric oxidation of isoprene and many other species and is commonly found in cloudwater. Previous work has established that glycolaldehyde evaporates more readily from drying aerosol droplets containing ammonium sulfate (AS) than does glyoxal, methylglyoxal, or hydroxyacetone, which implies that it does not oligomerize as quickly as these other species. Here, we report NMR measurements of glycolaldehyde’s aqueous-phase reactions with AS, methylamine, and glycine. Reaction rate constants are smaller than those of respective glyoxal and methylglyoxal reactions in the pH range of 3–6. In follow-up cloud chamber experiments, deliquesced glycine and AS seed particles were found to take up glycolaldehyde and methylamine and form brown carbon. At very high relative humidity, these changes were more than 2 orders of magnitude faster than predicted by our bulk liquid NMR kinetics measurements, suggesting that reactions involving surface-active species at crowded air–water interfaces may play an important role. The high-resolution liquid chromatography–electrospray ionization–mass spectrometric analysis of filter extracts of unprocessed AS + GAld seed particles identified sugar-like C(6) and C(12) GAld oligomers, including proposed product 3-deoxyglucosone, with and without modification by reactions with ammonia to diimine and imidazole forms. Chamber exposure to methylamine gas, cloud processing, and simulated sunlight increased the incorporation of both ammonia and methylamine into oligomers. Many C(4)–C(16) imidazole derivatives were detected in an extract of chamber-exposed aerosol along with a predominance of N-derivatized C(6) and C(12) glycolaldehyde oligomers, suggesting that GAld is capable of forming brown carbon SOA. American Chemical Society 2022-08-04 2022-08-18 /pmc/articles/PMC9393862/ /pubmed/35925760 http://dx.doi.org/10.1021/acs.jpca.2c02606 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Rodriguez, Alyssa A. Rafla, Michael A. Welsh, Hannah G. Pennington, Elyse A. Casar, Jason R. Hawkins, Lelia N. Jimenez, Natalie G. de Loera, Alexia Stewart, Devoun R. Rojas, Antonio Tran, Matthew-Khoa Lin, Peng Laskin, Alexander Formenti, Paola Cazaunau, Mathieu Pangui, Edouard Doussin, Jean-François De Haan, David O. Kinetics, Products, and Brown Carbon Formation by Aqueous-Phase Reactions of Glycolaldehyde with Atmospheric Amines and Ammonium Sulfate |
title | Kinetics, Products,
and Brown Carbon Formation by
Aqueous-Phase Reactions of Glycolaldehyde with Atmospheric Amines
and Ammonium Sulfate |
title_full | Kinetics, Products,
and Brown Carbon Formation by
Aqueous-Phase Reactions of Glycolaldehyde with Atmospheric Amines
and Ammonium Sulfate |
title_fullStr | Kinetics, Products,
and Brown Carbon Formation by
Aqueous-Phase Reactions of Glycolaldehyde with Atmospheric Amines
and Ammonium Sulfate |
title_full_unstemmed | Kinetics, Products,
and Brown Carbon Formation by
Aqueous-Phase Reactions of Glycolaldehyde with Atmospheric Amines
and Ammonium Sulfate |
title_short | Kinetics, Products,
and Brown Carbon Formation by
Aqueous-Phase Reactions of Glycolaldehyde with Atmospheric Amines
and Ammonium Sulfate |
title_sort | kinetics, products,
and brown carbon formation by
aqueous-phase reactions of glycolaldehyde with atmospheric amines
and ammonium sulfate |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9393862/ https://www.ncbi.nlm.nih.gov/pubmed/35925760 http://dx.doi.org/10.1021/acs.jpca.2c02606 |
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