Analysis of oil obtained from mild hydrogenation of coal. 1. structural analysis of fractionated oil

Shin Yubari coal (86.7% C) was mildly hydrogenated repeatedly at 340–385°C under an initial hydrogen pressure of 10 MPa for 1 h, using Adkins catalyst. The product was extracted with benzene at 200°C and the residue was again reacted. Finally, benzene solubles were extracted with n-hexane, and n-hexane insolubles were hydrogenated under similar conditions at 380°C; the product was then extracted with n-hexane. The yield of total n-hexane solubles was 52.5%. Acid and base were extracted with sulfuric acid and NaOH, and the neutral part (50.2%) was chromatographed using an alumina column with 2.5% water and separated into 12 fractions. UV and IR spectra, ultimate analysis and ¹H-NMR spectra were obtained for each fraction and a structural analysis was carried out to obtain an image of each average structure. The aromatic ring numbers estimated from UV spectra and from structural analysis for each fractions agree well with each other; the average value was 3.2.