Synthesis of model compounds for coal liquefaction research
The objectives of this project are to develop feasible synthetic routes to produce (1) 4(4{prime}-hydroxy-5{prime},6{prime},7{prime},8{prime}-tetrahydro-1{prime}-naphthylmethyl)-6-methyldibenzothiophene, and (2) a 1-hydroxynaphthalene-dibenzothiophene polymer. These compounds are thought to be representative of sulfur containing molecules in coal. The program is divided into three tasks, the first of which is a project work plan that has already been submitted. There are several possible synthetic routes to the target molecule (1). The authors are now investigating two general synthetic approaches: coupling of a dialkylated dibenzothiophene fragment with the phenol, and coupling of a monoalkylated dibenzothiophene fragment with a monoalkylated phenol fragment. This quarter they developed syntheses for the reaction fragments and conducted some preliminary coupling experiments. They found that polymerization of the fragments is a problem; however, using an acidic resin as catalyst they believe to have controlled the polymerization reactions and formed coupling products, although their identities have not yet been confirmed. During this quarter the authors prepared the dibromodibenzothiophene starting material for (2) which they plan to convert to bis(hydroxymethyl)dibenzothiophene. Also during the next quarter, they will examine conditions for acid-catalyzed formation of an oligomer of 1-hydroxynaphthalene and formaldehyde containing five to twelve naphthyl units. 6 refs., 18 figs.
- Research Organization:
- SRI International, Menlo Park, CA (USA)
- Sponsoring Organization:
- DOE; USDOE, Washington, DC (USA)
- DOE Contract Number:
- AC22-90PC90036
- OSTI ID:
- 5993584
- Report Number(s):
- DOE/PC/90036-T2; ON: DE91010542
- Country of Publication:
- United States
- Language:
- English
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Synthesis of model compounds for coal liquefaction research: Final report, June 21, 1990--July 30, 1993
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Related Subjects
010405* -- Coal
Lignite
& Peat-- Hydrogenation & Liquefaction
ALDEHYDES
ALKANES
ALKENES
AROMATICS
CATALYSTS
CHEMICAL BONDS
CHEMICAL PREPARATION
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
COAL LIQUEFACTION
COAL LIQUIDS
CYCLOALKANES
DESULFURIZATION
DOCUMENT TYPES
ELEMENTS
ETHYLENE
FLUIDS
FORMALDEHYDE
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROGEN TRANSFER
HYDROGENATION
HYDROXY COMPOUNDS
KINETICS
LIQUEFACTION
LIQUIDS
METHYLENE RADICALS
NONMETALS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXYGEN
PHENOLS
POLYCYCLIC SULFUR HETEROCYCLES
POLYMERIZATION
PROGRESS REPORT
RADICALS
REACTION INTERMEDIATES
REACTION KINETICS
REDUCTION
RESEARCH PROGRAMS
SYNTHESIS
THERMOCHEMICAL PROCESSES