The distribution of hydrogen types in the soluble fractions from the depolymerization of a series of coals has been determined by NMR analysis. The aromatic hydrogen content varies from 20 to 32% of the total hydrogen, and no simple relationship exists with coal rank. β-Paraffinic plus naphthenic hydrogens, the major type, exceed the α-hydrogens and comprise 38-66% of the nonaromatic hydro gens. The most striking variation in the structure of the six coals is the number of methylene bridges. The degree of depolymerization with phenol-BF 3 can be correlated directly with the number of methylene bridges found in the soluble fractions. A general coal structure in accord with our results consists of large units (MW > 4000) and smaller units (MW, 300-600) connected by methylene bridges.Jhe distribution of hydrogen types in coals continues to be a subject of con siderable interest in coal structure studies. Published data indicate that the fraction of aromatic hydrogens usually increases with increasing rank, but the absolute values depend on the specific analytical method used (7). Hydrogen type analysis of a single coal based on the application of NMR spectroscopy to the soluble fraction from depolymerization with phenol-BFa has been re ported by us (3). The conversion of coal to soluble fragments in substantial yields under very mild conditions permits a reliable determination of the hydrogen types by NMR analysis, and these results can be extrapolated to the parent coal with considerable confidence.This procedure has now been extended to a series of coals varying in rank from lignite (70% C) to a low volatile bituminous coal (91% C). In addition to determining the amount of aromatic and aliphatic hydrogens, the aromatic group will be further subdivided into monocyclic and polycyclic types. A more 493 Downloaded by KTH ROYAL INST OF TECHNOLOGY on August 11, 2015 |

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Caustic soda extraction of tar acids from tar distillates has the disadvantages of batch operation and consumption of reagents. A review of the literature showed that continuous solvent extraction methods had been explored using oxygenated solvents. These processes were not too satisfactory, owing to the production of impure tar acids or the necessity of recycling a substantial fraction of the tar acids to obtain a satisfactory recovery.

To a solution of 8.2 g (0.046 mol) of III-24, 2.8 g of dry CjHsN, and 80 ml of dry PhMe, at -10°, was added dropwise 47 ml of a 15% w/v of COCli in PhMe. The work-up of this reaction mixture and the subsequent reaction of the intermediate carbamoyl chloride with EtOH-NIL followed the published procedure.Zc The yield of crude III-27 was 1.45 g; chromatography, in CeHe solution, on 60 g of alumina (Harshaw, Chromatographic Grade), followed by successive elutions with C«H6 and (-PrOH, and repeated recrystallizations from ß 6 were required to give pure III-28.8 5-Acetyl-7-chloro-5,ll-dihydrodibenz[b,e] [l,4]oxazepine (III-10).-A solution of 2.0 g (0.0087 mole) of 7-chloro-5,1 l-dihydro-' urm, < l at. dibenz]f),<:j [ 1,4] oxazepine,2* 25 ml of Ae-O, and 0.4 g of p-toluenesulfonic acid was heated under reflux for 2 hr, coned to dryness, and the residue distributed between 50 ml of Et»<) and 25 ml of said aq NaHCO». The Et»0 layer was sepd, washed with said a<[ NaCl, dried, and coned to give 2.4 g of 111-1(1.6-[ (o-Bromobenzy 1 )oxy] -Qf,a,a-trifluoro-»i-acetotoluidide . A mixture of 20.0 g (0.052 mol) of II-2. 8.6 g (0.1 1 mol) of anhyd AcONa, and 120 ml of glacial AeOH was heated under reflux for 3 hr, cooled somewhat, and poured into 300 ml of HiO. The oil, that sepd initially, solidified, and was filtered and dried to give 10.4 g of II-4.(8) The difficulties encountered in this synthesis are similar to those previously described in the oxazepine series, and are involved in the reaction of tiie heterocycle with phosgene."c Synthesis and Hypocholesterolemic Activity of Alkylidenedithio Bisphenols .

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