Facile reaction/extraction of coal with supercritical fluids. Quarterly technical progress report, January 1-March 31, 1984

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Arylmethyl phenyl ethers undergo competing reactions when treated with Lewis acids in benzene solvent. Apparently, benzene is insufficiently reactive to compete with intramolecular (intrapolymer) nucleophiles and, consequently, no increase in solubility accompanies the cleavages of ether links upon addition of benzene. When better nucleophiles, naphthalene and phenanthene, are provided, carbonium ions generated from ether cleavages are capped and the product is lower in molecular weight and more soluble. It is worth noting that the naphthalene (k/sub rel/ = 300) is nearly as good a trap as the phenol (k/sub rel/ = 450). Since hydroxylic solvents will level the acid strength … continued below

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9 pages

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Venier, C. G. & Squires, T. G. April 20, 1984.

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Arylmethyl phenyl ethers undergo competing reactions when treated with Lewis acids in benzene solvent. Apparently, benzene is insufficiently reactive to compete with intramolecular (intrapolymer) nucleophiles and, consequently, no increase in solubility accompanies the cleavages of ether links upon addition of benzene. When better nucleophiles, naphthalene and phenanthene, are provided, carbonium ions generated from ether cleavages are capped and the product is lower in molecular weight and more soluble. It is worth noting that the naphthalene (k/sub rel/ = 300) is nearly as good a trap as the phenol (k/sub rel/ = 450). Since hydroxylic solvents will level the acid strength of BF/sub 3/ to that of ROBF/sub 3//sup -/H/sup +/ and hydrocarbons would not, the acid-catalyzed bond cleavages necessary for unlinking coal may in fact be faster in BF/sub 3/-arene than in BF/sub 3/-phenol. While we have not yet extended these results to coals, we believe that the combination of a relatively mild Lewis acid catalyst, BF/sub 3/, with a good carbonium ion trap, naphthalene, will allow selective cleavage and capping of aryl alkyl ether bonds. 3 references, 2 figures, 3 tables.

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9 pages

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NTIS, PC A02/MF A01; 1.

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  • April 20, 1984

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Thumbnail image of item number 1 in: 'Facile reaction/extraction of coal with supercritical fluids. Quarterly technical progress report, January 1-March 31, 1984'.
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Venier, C. G. & Squires, T. G. Facile reaction/extraction of coal with supercritical fluids. Quarterly technical progress report, January 1-March 31, 1984, report, April 20, 1984; United States. (https://digital.library.unt.edu/ark:/67531/metadc1058700/: accessed May 29, 2024), University of North Texas Libraries, UNT Digital Library, https://digital.library.unt.edu; crediting UNT Libraries Government Documents Department.

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