Reactions of the toluene-insoluble, pyridine-soluble fraction of Illinois No. 6 coal

Technical Report · Mon Jan 01 04:00:00 EST 1979

DOI:https://doi.org/10.2172/6099030· OSTI ID:6099030

Mayo, F. R.; Buchanan, D. H.; Pavelka, L. A.

Illinois No. 6 coal was extracted with pyridine at 100/sup 0/ and the toluene-insoluble, pyridine-soluble (TIPS) fraction of the extract was used as a model for the 84% of insoluble coal. Various TIPS fractions had number-average molecular weights (anti M/sub n/) in pyridine of 980 to 1380 but were insoluble or only partly soluble in most other solvents. Elemental and /sup 1/H and /sup 13/C NMR analyses indicate an H/C ratio of only 1.3 in the aliphatic portions of the TIPS molecules. The TIPS fraction was treated with a variety of reagents and their abilities to cleave ether and ester bonds were measured by decreases in anti M/sub n/: ZnCl/sub 2/ > LiI.H/sub 2/O > ZnBr/sub 2/ > pyridine.HI > methyl iodide > benzylamine > alcoholic KOH > toluene sulfonic acid. Evidence for ester groups comes from saponification equivalents and the effects of alcoholic KOH and amines on anti M/sub n/. HI appears to cleave all the bonds that Na cleaves and more, suggesting that there are few diaryl ether bonds and more phenyl alkyl and benzyl ether than dialkyl ether bonds.

• Research Organization: SRI International, Menlo Park, CA (USA)
• DOE Contract Number: AC22-78ET11423
• OSTI ID: 6099030
• Report Number(s): DOE/ET/11423-T2; ON: DE82003859
• Country of Publication: United States
• Language: English

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01 COAL, LIGNITE, AND PEAT
010407 -- Coal & Coal Products-- Solvent Extraction-- (-1987)
010600* -- Coal
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AMINES
AROMATICS
AZINES
BROMIDES
BROMINE COMPOUNDS
CARBONACEOUS MATERIALS
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
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COAL EXTRACTS
ENERGY SOURCES
ESTERS
EXTRACTION
FOSSIL FUELS
FRACTIONATION
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GREAT LAKES REGION
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
HYDRIODIC ACID
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXIDES
ILLINOIS
INORGANIC ACIDS
INORGANIC PHOSPHORS
IODIDES
IODINATED ALIPHATIC HYDROCARBONS
IODINE COMPOUNDS
LITHIUM COMPOUNDS
LITHIUM HALIDES
LITHIUM IODIDES
MAGNETIC RESONANCE
MATERIALS
METHYL IODIDE
MOLECULAR WEIGHT
NORTH AMERICA
NUCLEAR MAGNETIC RESONANCE
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXYGEN COMPOUNDS
PHOSPHORS
POTASSIUM COMPOUNDS
POTASSIUM HYDROXIDES
PYRIDINE
PYRIDINES
RESONANCE
SEPARATION PROCESSES
SOLVENT EXTRACTION
STRUCTURAL CHEMICAL ANALYSIS
SULFONIC ACID ESTERS
TOLUENE
USA
ZINC BROMIDES
ZINC CHLORIDES
ZINC COMPOUNDS
ZINC HALIDES