Hydroxyacetone production from C3 Criegee intermediates

Taatjes, Craig A.; Liu, Fang; Rotavera, Brandon; Kumar, Manoj; Caravan, Rebecca; Osborn, David L.; Thompson, Ward H.; Lester, Marsha I.

doi:10.1021/acs.jpca.6b07712

Hydroxyacetone production from C₃ Criegee intermediates

Journal Article · Wed Dec 21 00:00:00 EST 2016 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.6b07712· OSTI ID:1340694

Taatjes, Craig A. ^[1]; Liu, Fang ^[2]; Rotavera, Brandon ^[1]; Kumar, Manoj ^[3]; Caravan, Rebecca ^[1]; Osborn, David L. ^[1]; Thompson, Ward H. ^[4]; ^[2]

Sandia National Lab. (SNL-CA), Livermore, CA (United States)
Univ. of Pennsylvania, Philadelphia, PA (United States)
Univ. of Nebraska, Lincoln, NE (United States)
Univ. of Kansas, Lawrence, KS (United States)

Hydroxyacetone (CH₃C(O)CH₂OH) is observed as a stable end product from reactions of the (CH₃)₂COO Criegee intermediate, acetone oxide, in a flow tube coupled with multiplexed photoionization mass spectrometer detection. In the experiment, the isomers at m/z = 74 are distinguished by their different photoionization spectra and reaction times. Hydroxyacetone is observed as a persistent signal at longer reaction times at a higher photoionization threshold of ca. 9.7 eV than Criegee intermediate and definitively identified by comparison with the known photoionization spectrum. Complementary electronic structure calculations reveal multiple possible reaction pathways for hydroxyacetone formation, including unimolecular isomerization via hydrogen atom transfer and –OH group migration as well as self-reaction of Criegee intermediates. Varying the concentration of Criegee intermediates suggests contributions from both unimolecular and self-reaction pathways to hydroxyacetone. As a result, the hydroxyacetone end product can provide an effective, stable marker for the production of transient Criegee intermediates in future studies of alkene ozonolysis.

View Accepted Manuscript (DOE)

Research Organization:: Sandia National Laboratories (SNL-CA), Livermore, CA (United States); Univ. of Pennsylvania, Philadelphia, PA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC04-94AL85000; FG02-87ER13792

OSTI ID:: 1340694

Alternate ID(s):: OSTI ID: 1598276

Report Number(s):: SAND--2017-0649J; 650605

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Journal Name: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory Journal Issue: 1 Vol. 121; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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