The kinetics and mechanism of an aqueous phase isoprene reaction with hydroxy radical
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1 The kinetics and mechanism of an aqueous phase isoprene reaction with hydroxy radical D. Huang, X. Zhang, Z. M. Chen, Y. Zhao and X. L. Shen State Key Laboratory of Environmental Simulation and Pollution Control, College of Environmental Sciences and Engineering, Peking University, Beijing , China Supplementary material Table S1. Mechanisms for the OH oxidation of isoprene in the box model. Fig. S1. Time series of products in the aqueous isoprene-oh reaction under the condition of 1.5 L top space in the.1 L reactor. Fig.S. Experiments 1 and (green and blue) for the kinetics of aqueous OH-initiated oxidation of isoprene (ISO), methacrolein (MACR), and methyl vinyl ketone (MVK) relative to salicylic acid at 8 K. (a) ISO/SA; (b) MACR/SA; (c) MVK/SA. Correspondence to: Z.M. Chen (zmchen@pku.edu.cn)
2 Table S1. Mechanisms for the OH oxidation of isoprene in the box model. Initial Adjusted Rate Rate NO Reaction constant constant (M -1 s -1 ) (M -1 s -1 ) 1 O + hv OH H (s -1 ) (s -1 ) O + OH HO H O H + HO + H O H O + O + OH HO + HO H O + O isoprene + OH R1O isoprene + OH RO isoprene + OH RO isoprene + OH R4O isoprene + OH R5O
3 10 isoprene + OH R6O R1O + R1O R1O + R1O + O RO + RO RO + RO + O RO + RO RO + RO + O R4O + R4O R4O + R4O + O R5O + R5O R5O + R5O + O R6O + R6O R6O + R6O + O R1O + RO R1O + RO + O R1O + RO R1O + RO + O R1O + R4O R1O + R4O + O R1O + R5O R1O + R5O + O R1O + R6O R1O + R6O + O RO + RO RO + RO + O
4 RO + R4O RO + R4O + O RO + R5O RO + R5O + O RO + R6O RO + R6O + O RO + R4O RO + R4O + O RO + R5O RO + R5O + O RO + R6O RO + R6O + O R4O + R5O R4O + R5O + O R4O + R6O R4O + R6O + O R5O + R6O R5O + R6O + O R1O + R1O RO + RO R4O + R4O R5O + R5O
5 6 R6O + R6O R1O + RO R1O + RO R1O + R4O R1O + R5O R1O + R6O RO + RO RO + R4O RO + R5O RO + R6O RO + R4O RO + R5O RO + R6O
6 49 R4O + R5O R4O + R6O R5O + R6O R1O + HO R1OOH + O RO + HO ROOH + O RO + HO ROOH + O R4O + HO R4OOH + O R5O + HO R5OOH + O R6O + HO R6OOH + O MVKAOO + R1O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MVKAOO + RO 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MVKAOO + RO 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MVKAOO + R4O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO
7 6 MVKAOO + R5O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MVKAOO + R6O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MVKBOO + R1O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MVKBOO + RO 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MVKBOO + RO 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MVKBOO + R4O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MVKBOO + R5O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MVKBOO + R6O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MACRAOO + R1O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MACRAOO + RO 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MACRAOO + RO 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MACRAOO + R4O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MACRAOO + R5O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO
8 75 MACRAOO + R6O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MACRBOO + R1O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MACRBOO + RO 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MACRBOO + RO 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MACRBOO + R4O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MACRBOO + R5O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO MACRBOO + R6O 0. * MACR + 0. * MVK * MG + HCHO + 1. * HO R1O H8O R5O H8O R1OOH+ OH H8O + OH R5OOH+ OH H8O + OH R1OOH H8O + HO + OH R5OOH H8O + HO + OH
9 C5H8O + OH 0.5 * C5H9O C H9O5 0.7* MG 0.7* GL C5H9O5 + HO H9O5H C5H9O5H + OH H9O C H O H 0.5* MG 0.5* GL R1O + O carbonyl + HO R1O carbonyl + HO RO + O MVK + HCHO + HO RO MVK + HCHO + HO RO + O HMVK + CHO RO HMVK+ CH O RO + O MVK + HCHO + HO RO MVK + HCHO + HO
10 101 RO + O MF + HCHO + HO RO MF + HCHO + HO R4O + O MACR + HCHO + HO R4O MACR + HCHO + HO R4O + O MF + HCHO + HO R4O MF + HCHO + HO R5O + O carbonyl + HO R5O carbonyl + HO R6O + O MACR + HCHO + HO R6O MACR + HCHO + HO CH O + O HO + HCHO R1O + CHO R1O + CHO + O R1O + CHO alcohol+ C5 carbonyl+ HCHO+ O
11 RO + CHO RO + CHO + O RO + CHO alcohol+ C5 carbonyl+ HCHO+ O RO + CHO RO + CHO + O RO + CHO alcohol+ C5 carbonyl+ HCHO+ O R4O + CHO R4O + CHO + O R4O + CHO alcohol+ C5 carbonyl+ HCHO+ O R5O + CHO R5O + CHO + O R5O + CHO alcohol+ C5 carbonyl+ HCHO+ O R6O + CHO R6O + CHO + O R6O + CHO alcohol+ C5 carbonyl+ HCHO+ O CH O + CHO CHO + CHO + O CH O + CHO alcohol+ C5 carbonyl+ HCHO+ O MACR + OH 0.5 CH (OH)C (CH )CHO CH C(OH)(CH )CHO
12 17 MVK + OH 0.7 CH (OH)C HC(O)CH + 0. CH CH(OH)C(O) CH CH (OH)C (CH )CHO + O CH (OH)C(OO )(CH )CHO CH C(OH)(CH )CHO + O OOCH C(OH)(CH )CHO CH (OH)C HC(O)CH + O CH (OH)C(OO)HC(O)CH CH CH(OH)C(O)CH + O OOCH CH(OH)C(O) CH CH (OH)C(OO )(CH )CHO O CH C(O)CHO + CH OH + 0. CH (OH)C(O)CHO + 0. CH CH (OH)C(O)CH CHO OOCH C(OH)(CH )CHO OHCC(OH)(CH )CHO + H O OOCH C(OH)(CH )CHO OHCC(OH)(CH )CHO + CH (OH)C(OH)(CH )CHO + O OOCH C(OH)(CH)CHO HCHO + CH C (OH)CHO + O CHO + O CO + OH CHO HCHO + HCOOH CH C (OH)CHO + O CH C(OO)(OH)CHO
13 19 CH C(OO )(OH)CHO 0.8 CH COOH CHO OHCCOOH CH + 0. CH C(O)CHO + 0. OH CH (OH)C(OO )HC(O)CH CH (OH)C(O)C(O)CH + H O CH (OH)C(OO )HC(O)CH CH (OH)C(O)C(O)CH + CH (OH)CH(OH)C(O)CH + O CH 1.4 CH (OH)C(OO )HC(O)CH O (OH)CHO CH CO CH OH CH C(O)CHO OOCH CH(OH)C(O)CH OHCCH(OH)C(O)CH + H O OOCH CH(OH)C(O)CH OHCCH(OH)C(O)CH + CH (OH)CH(OH)C(O)CH + O OOCH CH(OH)C(O)CH HCHO + CH C(O)C H(OH) + O CH CO + O CH CO CH CO O + CO + CH CH CO + OH CH COOH CH CO CH COCOCH CH CO + CH O O + HCHO + CH COOH
14 151 CH (OH)CHO + OH CH (OH)COOH + HO + H O CH (OH)COOH+ OH CH(OH)COOH+ H O CH(OH)COOH+ O OOCH(OH)COOH OOCH(OH)CO OH + H O CH(OH) COOH + HO CH(OH) COOH + OH HOOCCOOH + HO + H O CH (OH)CHO + OH (OH) CHCH(OH) + HO CH(OH) COOH + HO HCOOH+ CO + HO (OH) CHCH(OH) + OH CHOCOOH + HO CH C(O)CH(OH) + O CH C(O)CH(OH) OO CH C(O)CH(OH)OO CH C(O)CHO + HO CH C(O)CH(OH)OO CH C(O)COOH + H O CHOCOOH + OH HOOCCOOH+ HO + H O HCHO + H O CH (OH) 0.18 (F) (F)
15 (B) (B) 164 CH (OH) + OH H O + HO + HCOOH HCOOH HCOO + H (F) (B) (F) (B) 166 HCOOH + OH H O + HO + CO HCOO + OH OH + HO + CO CH C(O)CHO + H O CH C(O)CH(OH) 1.5 (F) 0.5 (B) 1.5 (F) 0.5 (B) 169 CH C(O)CH(OH) + OH CH C(O)C(OH) + H O CH C(O)C(OH) + O CH C(O)C(OH) OO CH C(O)C(OH) OO CH C(O)COOH + HO CH C(O)COOH CH C(O)COO CH - - C(O)COO + hv CH COO - + H (F) (B) (s -1 ) (F) (B) (s -1 )
16 CH C(O)COO + H O CH COO + H O + CO CH C(O)COOH + OH CH C(O)COOH + H O CH C(O)COOH + O O CH C(O)COOH O CH C(O)COOH OHCC(O)COOH + H O CH COOH CH COO - + H (F) (B) (F) (B) 179 CH COOH + OH HOOCCOOH CH COO HOOCCOO OH HOOCCOOH + OH CO + H O + HO HOOCCOO + OH CO + H O + O HOOCCOOH HOOCCOO + H (F) (B) (F) (B) 184 CH + O CH O
17 185 CH O + CH O CH OH + HCHO + O CH OH + O OOCHOH OOCH OH CH OH + HCHO + O The formula or description of the simplified name in Table.1 are as follows: Name Formula/description Name Formula/description R1O HOCH C(CH ) = CHCH OO R5O OCH C(CH ) = CHCH OH RO HOCH C(CH )(OO )CH = CH R6O CH = C(CH )CH(O )CH OH RO R4O R5O R6O CH = CHC(CH )(OH)CH OO MACAOO CH (OH)C(OO )(CH )CHO CH = C(CH )CH(OH)CH OO MACBOO OOCH C(OH)(CH )CHO OOCH C(CH ) = CHCH OH MVKAOO CH (OH)C(OO)HC(O)CH CH = C(CH )CH(OO )CH OH MVKBOO OOCH CH(OH)C(O) CH R1O HOCH C(CH ) = CHCH O HMVK CH CH (OH)C HC(O)CH CH(OH)C(O)CH RO HOCH C(CH )(O )CH = CH C5H 8O Carbonyls (internal double bond)
18 RO CH = CHC(CH )(OH)CH O C 5H 9O 5 Peroxy radicals from C 5 -hydroxy aldehydes R4O CH = C(CH )CH(OH)CH O C 5 H 9O 5H Hydroperoxides from C 5H 9O 5 References: Bell, R. P. and Evans, P. G.: Kinetics of the dehydration of methylene glycol in aqueous solution, Proc. R. Soc., 91, 97, Betterton, E. A. and Hoffmann, M. R.: Henry s law constants of some environmentally important aldehydes, Environ. Sci. Technol.,, , Bothe, E., Schuchmann, M. N., Schulte-Frohlinde, D., and von Sonntag, C.: HO elimination from a-hydroxalkyl-peroxyl radicals in aqueous solution. Photochem. Photobiol., 8, , Buxton, G. V., Greenstock, C. L., Helman, W. P., and Ross, A. B.: Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals, (OH, O ) in aqueous solution, J. Phys. Chem. Ref. Data 17, , Carlton, A. G., Lim, H. J., Altieri, K., Seitinger, S., and Turpin, B. J.: Link between isoprene and secondary organic aerosol (SOA): pyruvic acid oxidation yields low volatility organic acids in clouds, Geophys. Res. Lett.,, L068, doi: /005GL0574, 006.
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23 Fig.S1. The time series of products in the aqueous isoprene-oh reaction under the condition of 1.5 L top space in the.1 L reactor.
24 0.6 -a- -b- -c- ln ([ISO]0/[ISO]t) y = 0.75x r = ln ([MACR]0/[MACR]t) y = 0.779x r = ln ([MVK]0/[MVK]t) y = 0.760x r = ln ([SA] 0 /[SA] t ) ln ([SA] 0 /[SA] t ) ln ([SA] 0 /[SA] t ) Fig.S. Experiments 1 and (green and blue) for the kinetics of aqueous OH-initiated oxidation of isoprene (ISO), methacrolein (MACR), and methyl vinyl ketone (MVK) relative to salicylic acid at 8 K. (a) ISO/SA; (b) MACR/SA; (c) MVK/SA.
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