Aqueous high-temperature chemistry of carbo- and heterocycles. 7. Monosubstituted benzenes with two carbon atom side chains oxygenated at the. alpha. - and. beta. -positions

Journal Article · · Energy and Fuels; (USA)

DOI:https://doi.org/10.1021/ef00023a021· OSTI ID:6123175

Katritzky, A R; Luxem, F J ^[1]; Siskin, M ^[2]

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1. Univ. of Florida, Gainesville (USA)
2. Exxon Research and Engineering Company, Annandale, NJ (USA)

The aquathermolysis of monosubstituted benzenes with two carbon atom side chains oxygenated at both the {alpha}- and {beta}-positions was studied. All the model compounds showed high reactivity in both water and cyclohexane. The {alpha}-keto and {alpha}-hydroxy acids showed mainly decarbonylation and decarboxylation reactions; loss of formic acid was also observed. For the acids, the {alpha}-keto aldehyde, and for the glycol disproportionation products are key intermediates for condensation and cyclization products. Mechanistic pathways are suggested in Schemes I-V for the formation of all products. A section tying together the reactivity trends and implications noted in the monosubstituted benzene series (parts 2 and 5-7) is included at the end of this paper.

• OSTI ID: 6123175
• Journal Information: Energy and Fuels; (USA), Journal Name: Energy and Fuels; (USA) Vol. 4:5; ISSN 0887-0624; ISSN ENFUE
• Country of Publication: United States
• Language: English

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04 OIL SHALES AND TAR SANDS
040200 -- Oil Shales & Tar Sands-- Reserves
Geology
& Exploration
040500* -- Oil Shales & Tar Sands-- Properties & Composition
ALCOHOLS
ALDEHYDES
ALKANES
AROMATICS
AUTOHYDROLYSIS
BENZENE
BITUMINOUS MATERIALS
CARBONACEOUS MATERIALS
CARBOXYLIC ACIDS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHEMISTRY
CYCLOALKANES
CYCLOHEXANE
DECARBOXYLATION
DECOMPOSITION
DIAGENESIS
DISSOCIATION
ENERGY SOURCES
FORMIC ACID
FOSSIL FUELS
FUELS
GEOCHEMISTRY
GLYCOLS
HEAT TREATMENTS
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROLYSIS
HYDROXY ACIDS
HYDROXY COMPOUNDS
KEROGEN
KINETICS
LYSIS
MANDELIC ACID
MASS SPECTROSCOPY
MATERIALS
MATURATION
MONOCARBOXYLIC ACIDS
OIL SHALES
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC MATTER
OXYGEN COMPOUNDS
PYROLYSIS
REACTION KINETICS
SOLVOLYSIS
SPECTROSCOPY
STRUCTURAL CHEMICAL ANALYSIS
THERMOCHEMICAL PROCESSES
WATER