HIGHLY EFFICIENT SEPARATIVE REFINING OF USEFUL COMPOUNDS IN COAL TAR

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Useful compounds such as polyaromatic hydrocarbons (naphthalene, methylnaphthalenes, anthracene, pyrene, fluoranthene and so on) and hetercoyclic compounds (quinoline, isoquinoline, acridine, benzothiophene and so on) were separated from coal tar fractions by combining solvent extraction and adsorption techniques using supported metal sulfates and a series of extraction solvents such as hexane, benzene, methanol and supercritical CO^2.Main research results are as follows ;1) Crude methylnaphthalene oil (CMNO) was effectively denitrogenated by adsorptive separation with 10 wt% Al^2(SO^4)^3 supported on silica gel of high surface area(Al/Si) and fractional extraction wiht hexane and benzene. Nitrogen compounds of quinoline and isoquinoline were concentrated and recovered in the benzene-eluted fraction at the same time.2) The same techniques as described above were applied to the selective separation of acridine from crude anthracene oil, providing an important starting material for preparing 1,2,3,4-tetrahydro-9-aminoacridine of expected remedy for Altzheimer-like senile dementia.3) CMNO was more selectively and effectively denitrogenated by using the Al/Si adsorbent under supercritical CO^2 extraction conditions of 50ﾟC and 70 atm than the conventional extraction methods. Nitrogen compounds of quinoline and isoquinoline were more easily and efficiently recovered by higher pressure supercritical CO^2 and methanol washing.4) Benzothiophene (BT) was more selectively dimerized over tha Al/Si catalyst under supercritical CO^2 conditions of 100ﾟC and 70 atm than its catalytic reaction in atmospheric n-octane solutions. The dimer of BT can be separated from crude naphthalene fraction under the supercritical CO^2 conditions followed by selective dedimerization and etraction.