Atmospheric chemistry of isopropyl formate and tert-butyl formate
Formates are produced in the atmosphere as a result of the oxidation of a number of species, notably dialkyl ethers and vinyl ethers. This work describes experiments to define the oxidation mechanisms of isopropyl formate, HC(O)OCH(CH3)2, and tert‐butyl formate, HC(O)OC(CH3)3. Product distributions...
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| Published in: | International journal of chemical kinetics Vol. 42; no. 8; pp. 479 - 498 |
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| Main Authors: | , , , , , , , |
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| Abstract | Formates are produced in the atmosphere as a result of the oxidation of a number of species, notably dialkyl ethers and vinyl ethers. This work describes experiments to define the oxidation mechanisms of isopropyl formate, HC(O)OCH(CH3)2, and tert‐butyl formate, HC(O)OC(CH3)3. Product distributions are reported from both Cl‐ and OH‐initiated oxidation, and reaction mechanisms are proposed to account for the observed products. The proposed mechanisms include examples of the α‐ester rearrangement reaction, novel isomerization pathways, and chemically activated intermediates. The atmospheric oxidation of isopropyl formate by OH radicals gives the following products (molar yields): acetic formic anhydride (43%), acetone (43%), and HCOOH (15–20%). The OH radical initiated oxidation of tert‐butyl formate gives acetone, formaldehyde, and CO2 as major products. IR absorption cross sections were derived for two acylperoxy nitrates derived from the title compounds. Rate coefficients are derived for the kinetics of the reactions of isopropyl formate with OH (2.4 ± 0.6) × 10−12, and with Cl (1.75 ± 0.35) × 10−11, and for tert‐butyl formate with Cl (1.45 ± 0.30) × 10−11 cm3 molecule−1 s−1. Simple group additivity rules fail to explain the observed distribution of sites of H‐atom ion for simple formates. © 2010 Wiley Periodicals, Inc. Int J Chem Kinet 42: 479–498, 2010 |
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| AbstractList | Formates are produced in the atmosphere as a result of the oxidation of a number of species, notably dialkyl ethers and vinyl ethers. This work describes experiments to define the oxidation mechanisms of isopropyl formate, HC(O)OCH(CH
3
)
2
, and
tert
‐butyl formate, HC(O)OC(CH
3
)
3
. Product distributions are reported from both Cl‐ and OH‐initiated oxidation, and reaction mechanisms are proposed to account for the observed products. The proposed mechanisms include examples of the α‐ester rearrangement reaction, novel isomerization pathways, and chemically activated intermediates. The atmospheric oxidation of isopropyl formate by OH radicals gives the following products (molar yields): acetic formic anhydride (43%), acetone (43%), and HCOOH (15–20%). The OH radical initiated oxidation of
tert
‐butyl formate gives acetone, formaldehyde, and CO
2
as major products. IR absorption cross sections were derived for two acylperoxy nitrates derived from the title compounds. Rate coefficients are derived for the kinetics of the reactions of isopropyl formate with OH (2.4 ± 0.6) × 10
−12
, and with Cl (1.75 ± 0.35) × 10
−11
, and for
tert
‐butyl formate with Cl (1.45 ± 0.30) × 10
−11
cm
3
molecule
−1
s
−1
. Simple group additivity rules fail to explain the observed distribution of sites of H‐atom abstraction for simple formates. © 2010 Wiley Periodicals, Inc. Int J Chem Kinet 42: 479–498, 2010 Formates are produced in the atmosphere as a result of the oxidation of a number of species, notably dialkyl ethers and vinyl ethers. This work describes experiments to define the oxidation mechanisms of isopropyl formate, HC(O)OCH(CH3)2, and tert‐butyl formate, HC(O)OC(CH3)3. Product distributions are reported from both Cl‐ and OH‐initiated oxidation, and reaction mechanisms are proposed to account for the observed products. The proposed mechanisms include examples of the α‐ester rearrangement reaction, novel isomerization pathways, and chemically activated intermediates. The atmospheric oxidation of isopropyl formate by OH radicals gives the following products (molar yields): acetic formic anhydride (43%), acetone (43%), and HCOOH (15–20%). The OH radical initiated oxidation of tert‐butyl formate gives acetone, formaldehyde, and CO2 as major products. IR absorption cross sections were derived for two acylperoxy nitrates derived from the title compounds. Rate coefficients are derived for the kinetics of the reactions of isopropyl formate with OH (2.4 ± 0.6) × 10−12, and with Cl (1.75 ± 0.35) × 10−11, and for tert‐butyl formate with Cl (1.45 ± 0.30) × 10−11 cm3 molecule−1 s−1. Simple group additivity rules fail to explain the observed distribution of sites of H‐atom ion for simple formates. © 2010 Wiley Periodicals, Inc. Int J Chem Kinet 42: 479–498, 2010 |
| Author | Wallington, Timothy J. Pimentel, Andre Silva Hurley, Michale D. Sulbaek Andersen, Mads P. Orlando, John J. Dibble, Theodore S. Tyndall, Geoffrey S. Marshall, Paul |
| Author_xml | – sequence: 1 givenname: Andre Silva surname: Pimentel fullname: Pimentel, Andre Silva organization: Departamento de Química, Pontificia Universidade Católica do Rio de Janeiro, Gávea 22453-900, Rio de Janeiro, RJ, Brazil – sequence: 2 givenname: Geoffrey S. surname: Tyndall fullname: Tyndall, Geoffrey S. email: tyndall@ucar.edu organization: National Center for Atmospheric Research, P. O. Box 3000, Boulder, CO 80307 – sequence: 3 givenname: John J. surname: Orlando fullname: Orlando, John J. organization: National Center for Atmospheric Research, P. O. Box 3000, Boulder, CO 80307 – sequence: 4 givenname: Michale D. surname: Hurley fullname: Hurley, Michale D. organization: Physical & Environmental Sciences Department, Ford Motor Company, Mail Drop SRL-3083, Dearborn, MI 48121 – sequence: 5 givenname: Timothy J. surname: Wallington fullname: Wallington, Timothy J. organization: Physical & Environmental Sciences Department, Ford Motor Company, Mail Drop SRL-3083, Dearborn, MI 48121 – sequence: 6 givenname: Mads P. surname: Sulbaek Andersen fullname: Sulbaek Andersen, Mads P. organization: Department of Chemistry, University of California, Irvine, Irvine, CA 92697 – sequence: 7 givenname: Paul surname: Marshall fullname: Marshall, Paul organization: Center for Advanced Scientific Computing and Modeling, Department of Chemistry, University of North Texas, 1155 Union Circle, #305070, Denton, TX 76203-5017 – sequence: 8 givenname: Theodore S. surname: Dibble fullname: Dibble, Theodore S. organization: Chemistry Department, State University of New York-Environmental Science and Forestry, Syracuse, NY 13210 |
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| CitedBy_id | crossref_primary_10_1002_kin_21172 crossref_primary_10_1039_C8RA09627A crossref_primary_10_1016_j_jphotochem_2018_04_052 crossref_primary_10_1021_acs_est_1c04177 crossref_primary_10_1007_s13762_014_0686_9 crossref_primary_10_1246_cl_210015 crossref_primary_10_1021_acs_jpca_9b08410 crossref_primary_10_5194_acp_19_7691_2019 crossref_primary_10_1021_es404771d crossref_primary_10_1021_acs_jpca_1c03814 crossref_primary_10_1039_c2cs35070j crossref_primary_10_1021_acs_jpca_8b11294 crossref_primary_10_1016_j_cplett_2014_04_020 crossref_primary_10_1039_c2cp23711c |
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| Snippet | Formates are produced in the atmosphere as a result of the oxidation of a number of species, notably dialkyl ethers and vinyl ethers. This work describes... |
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| Title | Atmospheric chemistry of isopropyl formate and tert-butyl formate |
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