Mineral oils: processes and products – Chemical conversion of hydrocarbons
Patent
1979-08-23
1981-03-31
Gantz, Delbert E.
Mineral oils: processes and products
Chemical conversion of hydrocarbons
208 8LE, 208 9, 208 14, 208 22, C10G 100, C10G 106
Patent
active
042591724
ABSTRACT:
Increased solubility of heavy fractions of coal (e.g., coal liquefaction bottoms and coal solubilization bottoms) is obtained by oxygen-alkylation or oxygen-acylation of weakly acidic protons such as phenolic and carboxylic functionalities by means of a phase transfer reaction. Phenolic and carboxylic functional substituents, which are very polar, are converted to relatively nonpolar ethers and esters, respectively. The O-alkylation or O-acylation is carried out in a binary liquid phase solution (organic and water phases with a solid phase suspended in the medium). A quaternary ammonium or phosphonium salt is reacted with alkali or alkaline earth base to produce the corresponding quaternary ammonium or phosphonium base (an example of a phase transfer reagent). This quaternary base is non-nucleophilic and readily removes the phenolic and carboxylic protons but does little else to the coal structures. After the removal of the weakly acidic protons by the quaternary base, the phenoxides and carboxylates which are produced then undergo O-alkylation or O-acylation. The alkylating or acylating agent comprises a carbon-bearing functionality and a displaceable leaving group. The O-alkylation or O-acylation reduces hydrogen bonding and polarity, thereby rendering heavy coal fractions more soluble in common organic solvents and petroleum liquids.
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Collins D. W.
Exxon Research and Engineering Co.
Gantz Delbert E.
Naylor Henry E.
Wright William G.
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