Characterization of Tar Acids from Coal-Hydrogenation Oils Page: III
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CONTENTS
Page
Preface----------------------------------------------1
Introduction ------------------------------------------------------------------ 2
Summary --------------------------------------- 3
Acknowledgments-- 4
History of previous work 5
Characterization of coal-carbonization products 5
Previous investigations of coal-hydrogenation products -- 6
Preliminary investigations of experimental techniques - 7
Partition studies on model compounds- 7
Measurement of partition coefficients - - 7
Relationship between partition coefficient and ionization constant - __ _-- 8
Distribution of HA when association occurs in the organic phase 9----------- - 9
Calculation of ionization constant from partition measurements _ 9
Relationship between ionization constant and molecular structure - 9
Effect of "true" partition coefficient (k) and ionization constant on observed partition coefficient
(k') _. . 10
Relationship between "true" partition coefficient (k) and molecular structure ___10
Extractibility of phenols 11
Countercurrent distribution studies on model compounds ---------------------------------------11
Homogeneity studies- _ _--13
Separation of isomers ------------------------------------------------------- 14
Methylation of phenols ----------------------------------------------------------- 15
With diazomethane_ ----------------------------------------- 15
With dimethyl sulfate -15
Demethylation of methyl ethers--- - - 16
2-Fluorenylisocyanate as a reagent for phenols -- 16
Preparation of 2-fluorenylisocyanate ---------------------------16
Preparation of N-(2-fluorenyl)carbamates ---- 17
Chromatographic absorption studies_ --17
Use of fluorescent derivatives in chromatography- _ --- -17
Use of fluorescent absorbents in chromatography -- 17
Infrared spectra of phenols- ____ -17
Relationship between infrared spectrum and CH and OH bond stretching 17
Quantitative analysis of phenols by infrared absorption -21
Ultraviolet spectra of phenols - --23
Source of tar acids investigated - - - -- ---24
Production of oil by hydrogenation of Bruceton coal ----------24
Preliminary fractionation - _-_24
Extraction of tar acids with Claisen alkali- -- -24
Fractional distillation of crude phenols _ _ 24
Preliminary distillation at reduced pressure-- 25
Precise fractional distillation at reduced pressure 25
Isolation and identification of individual phenols-__ 27
Phenol ---------------27
o-cresoL ------------------27
m- and p-cresol ----- 27
2,5-xylenol --------------------------------------- 28
Attempted separation of xylenols by fractional precipitation _ 28
2,4-xylenol 28
Separation of phenols in the xylenol range by distillation of their methyl ethers_ _-28
2,3-xylenol -----------29
Mesitol. Oxidation of methyl ethers-_ _________29
Attempted preparation of methoxytrimesic acid-trimethyl ester- __- 30
3,5-xylenol ----------------30
m-ethylphenol _____-_--- - - - -30
o- and p-ethylphenol _ _____- - -__- -_30
3-methyl-5-ethylphenoL - _______--30
III
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Woolfolk, E. O.; Golumbic, C.; Friedel, R. A.; Orchin, Milton & Storch, H. H. Characterization of Tar Acids from Coal-Hydrogenation Oils, report, 1950; Washington D.C.. (https://digital.library.unt.edu/ark:/67531/metadc12646/m1/3/: accessed July 15, 2024), University of North Texas Libraries, UNT Digital Library, https://digital.library.unt.edu; crediting UNT Libraries Government Documents Department.