High value products derived from coal-based feedstocks

Example 1: PAH Content

[0075]Two types of solvent extraction were investigated to produce coal extracts: (i) using dimethylformamide (dmf) as a low reactivity solvent to physically extract some coal molecules at either ambient temperature or under Soxhlet extraction conditions; and (ii) exposing the coal to the hydrogen donor solvent tetralin at elevated temperatures in a flow through system. Tetralin donates hydrogen to the coal structure and extract smaller fragments from the coal. During this process naphthalene and other tetralin dehydrogenation products are formed.

[0076]After tetralin extraction, and as the extracted liquid begins to cool, precipitates (tetralin-insoluble=TI) are formed at different temperatures. Precipitation continues to occur until the liquid reaches ambient temperature. The precipitate at different temperatures have different chemical functionalities as measured by FTIR, elemental analysis, thermogravimetric analysis, proton nuclear magnetic resonance spectrosc

Example 2: Tetralin Extraction

[0084]In some embodiments, the TI material and some derivatives can be used to impart similar effects to air blowing and other processes to make multigrade bitumen and therefore may be amenable for formulation hard grade asphalt (or bitumen).

[0085]Without wishing to be bound by theory, it is believed that during liquefaction of coal, in the presence of a hydrogen donor solvent, like tetralin, some bonds in the coal macromolecular structure are degraded to produce smaller molecular fragments. During this process, hydrogen is transferred from the hydrogen donor tetralin molecules to the coal facilitating the formation of these smaller molecule fragments, while producing various forms of dehydrogenated tetralin species. It was found that after the liquefaction process, and as the extracted liquid begins to cool, precipitates are formed at different temperatures (tetralin-insoluble=TI). Precipitation continues to occur until the liquid reaches ambient temperat

Example 3: DMF Extract with Esterification Using Acyl Chloride and Organic Base

[0095]A Soxhlet apparatus was set up and dimethylformamide (DMF) was used under ambient atmosphere to extract coal material. After removal of the DMF, this material was insoluble in toluene and dichloromethane but mostly soluble in pyridine. As shown in Table 1, GCMS analysis of this material showed that it contained very little smaller PAHs. Phenanthrene was detected at 17 ppm and no other smaller (≤4 rings) PAHs were observed above 10 ppm. Some larger PAHs were detected: benzo[b]fluoranthene and benzo[k]fluoranthene together were 82 ppm, benzo[a]pyrene was 62 ppm, Indeno[1,2,3-cd]pyrene was 80 ppm, and Benzo[g,h,i]perylene was 107 ppm. In contrast a standard paving grade coal tar pitch contained all of the major PAHs found in the EPA mix consisting of acenaphthylene, fluorine, phenanthrene, anthracene, pyrene, benzo[a]anthracene, chrysene, benzo[b]fluoranthrene, benzo[k]fluoranthene, benzo[a]pyrene, benzo[