Pyrolysis of the Simplest Carbohydrate, Glycolaldehyde (CHO-CH2OH), and Glyoxal in a Heated Microreactor

Porterfield, Jessica P.; Baraban, Joshua H.; Troy, Tyler P.; Ahmed, Musahid; McCarthy, Michael C.; Morgan, Kathleen M.; Daily, John W.; Nguyen, Thanh Lam; Stanton, John F.; Ellison, G. Barney

doi:10.1021/acs.jpca.6b00652

Pyrolysis of the Simplest Carbohydrate, Glycolaldehyde (CHO-CH₂OH), and Glyoxal in a Heated Microreactor

Journal Article · Wed Mar 16 00:00:00 EDT 2016 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.6b00652· OSTI ID:1464135

Porterfield, Jessica P. ^[1]; Baraban, Joshua H. ^[1]; Troy, Tyler P. ^[2]; Ahmed, Musahid ^[2]; McCarthy, Michael C. ^[3]; Morgan, Kathleen M. ^[4]; Daily, John W. ^[5]; Nguyen, Thanh Lam ^[6]; Stanton, John F. ^[6]; Ellison, G. Barney ^[1]

Univ. of Colorado, Boulder, CO (United States). Dept. of Chemistry and Biochemistry
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Chemical Sciences Division
Harvard-Smithsonian Center for Astrophysics, Cambridge, MA (United States)
Xavier Univ. of Louisiana, New Orleans, LA (United States). Dept. of Chemistry
Univ. of Colorado, Boulder, CO (United States). Center for Combustion and Environmental Research and Dept. of Mechanical Engineering,
Univ. of Texas, Austin, TX (United States). Dept. of Chemistry

Both glycolaldehyde and glyoxal were pyrolyzed in a set of flash-pyrolysis microreactors. The pyrolysis products resulting from CHO-CH₂OH and HCO-CHO were detected and identified by vacuum ultraviolet (VUV) photoionization mass spectrometry. Complementary product identification was provided by argon matrix infrared absorption spectroscopy. Pyrolysis pressures in the microreactor were about 100 Torr, and contact times with the microreactors were roughly 100 μs. At 1200 K, the products of glycolaldehyde pyrolysis are H atoms, CO, CH₂=O, CH₂=C=O, and HCO-CHO. Thermal decomposition of HCO-CHO was studied with pulsed 118.2 nm photoionization mass spectrometry and matrix infrared absorption. Under these conditions, glyoxal undergoes pyrolysis to H atoms and CO. Tunable VUV photoionization mass spectrometry provides a lower bound for the ionization energy IE(CHO-CH₂OH) ≥ 9.95 ± 0.05 eV. The gas-phase heat of formation of glycolaldehyde was established by a sequence of calorimetric experiments. The experimental result is Δ_fH₂₉₈(CHO-CH₂OH) = -75.8 ± 1.3 kcal mol^-1. Fully ab initio, coupled cluster calculations predict Δ_fH₀(CHO-CH₂OH) of -73.1 ± 0.5 kcal mol^-1 and Δ_fH₂₉₈(CHO-CH₂OH) of -76.1 ± 0.5 kcal mol^-1. The coupled-cluster singles doubles and noniterative triples correction calculations also lead to a revision of the geometry of CHO-CH₂OH. We have found that the O-H bond length differs substantially from earlier experimental estimates, due to unusual zero-point contributions to the moments of inertia.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: National Science Foundation (NSF); Robert A. Welch Foundation; USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division; Univ. of New Orleans, New Orleans, LA (United States). Advanced Materials Research Inst. (AMRI) Fabrication, Analysis, and Consulting Services (FACS)

Grant/Contract Number:: AC02-05CH11231; FG02-07ER15884

OSTI ID:: 1464135

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: 14 Vol. 120; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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