# Subcritical Extraction of Coal Tar Slag and Analysis of Extracts and Raffinates
## 3 Results and Discussion
### GC-MS Testing of Coal Tar Slag Extracts
 } \\  & 1-Decanol, 2-hexyl- & C\({}_{16}\)H\({}_{3}\)O & 242.30 & \\  & Tetracosyl pentafluoropropionate & C\({}_{27}\)H\({}_{48}\)F\({}_{5}\)O\({}_{2}\) & 500.70 & 1.01 \\  & Heptacosyl trifluoracetate & C\({}_{29}\)H\({}_{58}\)F\({}_{3}\)O\({}_{2}\) & 492.70 & \\  & 4a,7,7,10a- & & & & \\  & Tetramethyldodecanoyl drobenz[fchromen-3-ol & C\({}_{17}\)H\({}_{30}\)O\({}_{2}\) & 266.40 & \\  & 17-Pentaticornet & C\({}_{35}\)H\({}_{70}\) & 490.90 & 0.14 \\  & 2-Dodecen-1-yl(-)succincinic anhydride & C\({}_{16}\)H\({}_{32}\)O\({}_{3}\) & 266.38 & \\  & **Esters** & & & \\  & Succinic acid, 4-methylhept-3-ylonyl ester & C\({}_{21}\)H\({}_{49}\)O\({}_{4}\) & 356.50 & \\
31 & Tetracosyl pentafluoropropionate & C\({}_{27}\)H\({}_{48}\)F\({}_{5}\)O\({}_{2}\) & 500.70 & 0.28 \\  & 1-Decanol, 2-hexyl- & C\({}_{16}\)H\({}_{34}\)O\({}_{2}\) & 242.44 & \\  & Palmitic acid vinyl ester & C\({}_{18}\)H\({}_{34}\)O\({}_{2}\) & 282.50 & \\
36 & 17-Pentaticornet & C\({}_{35}\)H\({}_{70}\) & 490.90 & 0.27 \\  & E-10,13,13-Trimethyl-11-tetradecom-1-ol acetate & C\({}_{19}\)H\({}_{30}\)O\({}_{2}\) & 296.50 & \\  & Palmitic acid 2-nonanol ester & C\({}_{27}\)H\({}_{48}\)O\({}_{2}\) & 410.70 & \\
45 & 1-Decanol, 2-hexyl- & C\({}_{16}\)H\({}_{34}\)O & 242.44 & 0.25 \\  & Tetracosyl pentafluoropropionate & C\({}_{27}\)H\({}_{48}\)F\({}_{5}\)O\({}_{2}\) & 500.70 & \\
46 & 1-Decanol, 2-hexyl- & C\({}_{16}\)H\({}_{34}\)O\({}_{2}\) & 242.44 & 0.69 \\  & Tetracosyl pentafluoropropionate & C\({}_{27}\)H\({}_{48}\)F\({}_{5}\)O\({}_{2}\) & 500.70 & \\  & Phytyl, 2-methylguonate & C\({}_{25}\)H\({}_{48}\)O\({}_{2}\) & 380.60 & \\
54 & E-10,13,13-Trimethyl-11-tetradecom-1-ol acetate & C\({}_{19}\)H\({}_{36}\)O\({}_{2}\) & 296.50 & 0.39 \\  & Tetracosyl pentafluoropropionate & C\({}_{27}\)H\({}_{48}\)F\({}_{5}\)O\({}_{2}\) & 500.70 & \\
**Ketones** & & & & \\  & 2-(2-Indanylidene)-1-indanone & C\({}_{18}\)H\({}_{41}\)O & 246.30 & \\
26 & 2-(2-Indanylidene)-1-indanone & C\({}_{18}\)H\({}_{41}\)O & 246.30 & 1.46 \\  & Undec-10-ynoic acid, tetradecyl ester & C\({}_{25}\)H\({}_{46}\)O\({}_{2}\) & 378.60 & \\  & **Phenols** & & & \\  & 1-Hydroxypreme & C\({}_{16}\)H\({}_{10}\)O & 218.25 & \\
13 & 1-Hydroxypreme & C\({}_{16}\)H\({}_{10}\)O & 218.25 & 1.87 \\  & Clean-12-ene & C\({}_{30}\)H\({}_{50}\) & 410.70 & \\
**Ethers** & & & & \\  & Nonyl tetracosyl ether & C\({}_{33}\)H\({}_{68}\)O & 480.90 & \\
33 & 1-Decanol, 2-hexyl- & C\({}_{16}\)H\({}_{34}\)O & 242.44 & 0.48 \\  & 5-Methyl-Z-5-docosenes & C\({}_{29}\)H\({}_{46}\) & 322.60 & \\ \hline \multirow{4}{*}{20} & \multicolumn{4}{c}{**Nitrogen compounds**} \\  & Naphthalene-2-ol, 1-(4-morphol)(phenyl)methyl- & C\({}_{21}\)H\({}_{21}\)NO\({}_{2}\) & 319.40 & \\
20 & 2-[1-(2-1,3]Dithian-2-yl-ethyl)-pent-4-carboxylyl- & C\({}_{16}\)H\({}_{28}\)O\({}_{2}\)S\({}_{2}\) & 316.50 & 1.52 \\  & tetralhydroxyman & C\({}_{22}\)H\({}_{25}\)Cl\({}_{4}\)O\({}_{4}\) & 498.30 & \\  & & & \\  & & & \\  & & & \\  & 25 & Fumaric acid, heptadecyl octyl ester & C\({}_{29}\)H\({}_{5}\)O\({}_{2}\) & 466.70 & 1.70 \\  & Tetracacanoic acid, hexadecyl ester & C\({}_{30}\)H\({}_{69}\)O\({}_{2}\) & 452.80 & \\  & **Sulfuronus compounds** & & & \\  & & & \\  & & & \\  & & & \\  & & & \\  & & & \\  & & & \\  & & & \\  & & & \\  & & & \\  & &  
As can be seen in the total ion flow chromatogram 10 and Table 5 of the substance composition, a total of 16 substances were detected in the second extract, including 7 aliphatic hydrocarbons, with a relative content of 37.11%; 1 carboxylic acid, with a relative content of 1.96%; 1 alcohol, with a relative content of 3.55%; 1 aldehyde, with a relative content of 1.36%; 3 esters, with a relative content of 18.50%; 1 sulfur-containing compound with a relative content of 11.26%; and 2 other compounds with a relative content of 7.24%.