Identification and cleavage of breakable single bonds by selective oxidation, reduction, and hydrolysis. Quarterly report No. 16, July 1-October 31, 1982
Efforts were made to establish the presence of diarylmethane groups in coal by oxidations of the corresponding ketones with m-chloroperbenzoic acid. No evidence of such groups was found. Black acids from a nitric acid oxidation of EDA/DMSO-extracted coal were examined for ketone groups, using the oxime and infrared absorption; no ketone or oxime was found. Reactions of a TIPS fraction with pyridine hydroiodide in pyridine, hydrogen iodide (HI) in toluene, and by aqueous hydrogen iodide were examined using molecular weight changes, vapor-phase osmometry (VPO), gel permeation chromatography (GLC), and iodine incorporation. Reactions with pyridine hydroiodide were complete and fairly consistent, with incorporation of about one iodine atom for each new molecule formed. Reactions in toluene and water were incomplete. Reaction of TIPS with benzylamine (BnNH/sub 2/) resulted in less cleavage than with pyridine hydroiodide, as measured by VPO, and inconclusive results by GPC. Exhaustive extractions of eight coals with BnNH/sub 2/ at 100/sup 0/C show that the beneficiated PSOC 25 lot of Illinois No. 6 coal gives 45% of soluble material. A plot of the ratio, BnNH/sub 2/ solubility/pyridine solubility, against %C dmmf in the coals gives a smooth curve. A TIPS fraction has been fractionated into smaller fractions by GPC, and molecular weights have been estimated; results agree reasonably well. The 96.6% of a BnNH/sub 2/ extract that is soluble in pyridine was compared with a whole TIPS fraction by GPC. Molecular weights range from 300 to 4000, with the BnNH/sub 2/ fraction averaging significantly higher than the TIPS fractions. Attempts to increase the solubility of black acids were unsuccessful.
- Research Organization:
- SRI International, Menlo Park, CA (USA)
- DOE Contract Number:
- AC22-78ET11423
- OSTI ID:
- 6519072
- Report Number(s):
- DOE/ET/11423-T6; ON: DE83005312
- Country of Publication:
- United States
- Language:
- English
Similar Records
Identification and cleavage of breakable single bonds by selective oxidation, reduction, and hydrolysis. Quarterly report No. 12, June 1-September 30, 1981
Identification and cleavage of breakable single bonds by selective oxidation, reduction, and hydrolysis. Quarterly report No. 15, April 1-June 30, 1982
Related Subjects
010600* -- Coal
Lignite
& Peat-- Properties & Composition
AMINES
AZINES
BITUMINOUS COAL
BLACK COAL
CARBONACEOUS MATERIALS
CHEMICAL BONDS
CHEMICAL REACTIONS
CHROMATOGRAPHY
COAL
ENERGY SOURCES
EXTRACTION
FOSSIL FUELS
FRACTIONATION
FUELS
HALOGEN COMPOUNDS
HETEROCYCLIC COMPOUNDS
HYDRIODIC ACID
HYDROGEN COMPOUNDS
INORGANIC ACIDS
IODINE COMPOUNDS
MATERIALS
MOLECULAR WEIGHT
NITRIC ACID
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIDATION
PYRIDINES
RESEARCH PROGRAMS
SEPARATION PROCESSES
SOLUBILITY
SOLVENT EXTRACTION
STRUCTURAL CHEMICAL ANALYSIS