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Title: Coal. Kinetics of o-alkylation

Abstract

The kinetic reactivities of the acidic hydroxyl groups in coal were measured. The chemical action of quaternary ammonium hydroxide bases in the presence of alkylating agents was used as the probe. Both Illinois No. 6 bituminous and Rawhide subbituminous coals contain aromatic and aliphatic hydroxyls as well as lesser amounts of carboxylic acids. Illinois coal was found to 0-alkylate at a faster rate than Rawhide coal. The reactivities of the acidic functional groups in the coals were correlated to the reactivity of acidic groups in model compounds. This was accomplished by both relative and absolute kinetic rate measurements on each coal and a series of model systems. It was discovered that the activation energy associated with the nucleophilic displacement determined the rate of 0-alkylation of the coal. Therefore, the rate of this reaction is not limited by mass transport of the chemical reagents into the coal structure. In this sense, 0-alkylation of coal is a most unique reaction.

Authors:
;
Publication Date:
Research Org.:
Exxon Research and Engineering Co., Linden, NJ
OSTI Identifier:
6356339
Resource Type:
Journal Article
Journal Name:
J. Am. Chem. Soc.; (United States)
Additional Journal Information:
Journal Volume: 103:7
Country of Publication:
United States
Language:
English
Subject:
01 COAL, LIGNITE, AND PEAT; BITUMINOUS COAL; ALKYLATION; CHEMICAL REACTION KINETICS; HYDROXIDES; QUATERNARY COMPOUNDS; CHEMICAL REACTIONS; EXPERIMENTAL DATA; AMINES; AMMONIUM COMPOUNDS; BLACK COAL; CARBONACEOUS MATERIALS; COAL; DATA; ENERGY SOURCES; FOSSIL FUELS; FUELS; HYDROGEN COMPOUNDS; INFORMATION; KINETICS; MATERIALS; NUMERICAL DATA; ORGANIC COMPOUNDS; OXYGEN COMPOUNDS; REACTION KINETICS; 010600* - Coal, Lignite, & Peat- Properties & Composition

Citation Formats

Liotta, R, and Brons, G. Coal. Kinetics of o-alkylation. United States: N. p., 1981. Web. doi:10.1021/ja00397a025.
Liotta, R, & Brons, G. Coal. Kinetics of o-alkylation. United States. doi:10.1021/ja00397a025.
Liotta, R, and Brons, G. Wed . "Coal. Kinetics of o-alkylation". United States. doi:10.1021/ja00397a025.
@article{osti_6356339,
title = {Coal. Kinetics of o-alkylation},
author = {Liotta, R and Brons, G},
abstractNote = {The kinetic reactivities of the acidic hydroxyl groups in coal were measured. The chemical action of quaternary ammonium hydroxide bases in the presence of alkylating agents was used as the probe. Both Illinois No. 6 bituminous and Rawhide subbituminous coals contain aromatic and aliphatic hydroxyls as well as lesser amounts of carboxylic acids. Illinois coal was found to 0-alkylate at a faster rate than Rawhide coal. The reactivities of the acidic functional groups in the coals were correlated to the reactivity of acidic groups in model compounds. This was accomplished by both relative and absolute kinetic rate measurements on each coal and a series of model systems. It was discovered that the activation energy associated with the nucleophilic displacement determined the rate of 0-alkylation of the coal. Therefore, the rate of this reaction is not limited by mass transport of the chemical reagents into the coal structure. In this sense, 0-alkylation of coal is a most unique reaction.},
doi = {10.1021/ja00397a025},
journal = {J. Am. Chem. Soc.; (United States)},
number = ,
volume = 103:7,
place = {United States},
year = {1981},
month = {4}
}