Separation of arenols from a high-temperature coal tar

Intemational Joumal of Mining Science and Technology 22(2012)243-244Contents lists available at Sciverse ScienceDirectInternational Journal of Mining Science and technologyELSEVIERjournalhomepagewww.elsevier.com/locate/ijmstSeparation of arenols from a high-temperature coal tarTing Yao. Zhi-Min Zong Zhe Wen, Robert Mukasa, Nan-Hua Yuan, Xian-Yong Weiation( Mimistry of Educanon] China University of Mining G Technology. Xuzhou 221008, ChinaPanzhihua Coal Corportation Coking Co, Ltd. Panzhihua 617016. ChinaARTICLE INFOABSTRACTA high-temperature coal tar collected from Xuzhou Coking Plant, Saint-Gobain Pipelines(Xuzhou)Co,July 2011Ltd was exhaustively extracted with petroleum ether(PE) The extract was sequentially eluted through三29 September 2011silica gel with PE and PE/ethyl acetate(EA)mixed solvents (volume ratio 2: 1) to afford two eluted fracnline 20 March 2012tions. The extract and eluted fractions were analyzed with gas chromatography/mass spectrometry. Intotal. 14 arenols were detected, including phenol, cresols. xylenols, tluorenols, phenanthren-3-ol andpyren-1-oLe 2012 Published by Elsevier B.V. on behalf of China University of Mining TechnologyIdentificationGC/MS analysis1 Introductionthe contents of ash and water are <4.0, 1.98 g/cm, <0. 13% andCoal tars are obtained by condensation of vapors released duringSolvents methanol, petroleum ether(PE)and ethyl acetate(EA)al carbonization [1]. High-temperature coal tar (HTCT)is produced are analytical-pure reagents and were distilled prior to use.during coke making at ca 1000C. Main components in hTCt arecondensed arenes( CAs)along with small amounts of heteroatomic 2.2. Solvent extraction, silica-gel column chromatography (SGCc) andrganic compounds (HAOCs) Most of the AOCs are value-added GC/Ms analysishemicals. Among the HAOCs, arenols are relatively abundant [21Arenols, especially phenols, are broadly used in medicines, plasAs Fig. 1 shows, ca. 4 gof the htCT and 100 mLof PE were put intocs pesticides and as feed stock for preparing other chemicalsa 250 mL round-bottom flask and subject to ultrasonic irradiationThe largest use of phenol is as an intermediate in the production of (USi)for 0. 5 h followed by filtration through a membrane filter olphenolic resins, synthetic fibers or epoxy resin precursors [3]. Wang Teflon with pore size of 0. 45 um to afford filtrate and filter cakeet al. extracted phenols from a low-temperature coal tar(ltct)by a( FC) The FC was separated to extraction solution 1(ES,)and residuesoda wash method 5 Zhang et al. studied polar compounds in coal(R,)by extraction with PE in a Soxhlet extractor ( SE)for 24 h.Aftertars using HPLC and identified 2, 4-xylenol and p-phenylphenol [6]. being sampled for analysis with a Hewlett-Packard 6890/5973 GC/Tiruta-Barna et al. investigated the release of phenols and CAs MS, the filtrate and ES, were incorporated as incorporated solutioncontained in a coal tar that was in contact with water 71-(ICS) which was transferred into a silica gel (SG)-packed columnLittle attention was paid to arenols in HTCT because of their (3 cm i.d. and 60 cm height of SG packed)and eluted with I L of PImuch lower contents compared to arenols in LtoT. In the present to afford eluted fraction 1(EF1)and retentate 1(R1). The Ri wasork, we tried to develop a convenient approach for separateluted with 0.5 L of PE/EA(volume ratio 2: 1) mixed solvent to affordnd enriching arenols from htct.eluted fraction 2(EF2)and retentate 2(R'2) The R, was extractedith 120 mL of methanol in the se to afford extraction solution 22.E(ES2)and residue 2(R2)The EF EF2 and ESz were also analyzed withthe GC/ MS but no compounds were detected in ES22.1. Sample and solvents3. Results and discussionThe hTct was collected from the Xuzhou Coking Plant. saint-Gobain Pipelines(Xuzhou)Co, Ltd. Its Engler viscosity, density, 3. 1. Identification of arentsrresponding author. TeL: +86 13685190472AsILICNMHG1, 14 phenols with 1-trate, ES and EF2. Nosee front matter o 2012 Published by elsevier B V. on behalf of China Universityg101016/jmt201100o244Y. Ting et aL/Intemational Joumal of Mining Sdence and Technology 22(43-24ITCT 4gArenols detected in ICS, ES, and EFxracton with PE under UsIFiltrateon with PE in SI甲√√5sGcc withtraction with mothanol in S2,4-xylenol7√v图E(则|es(RsGCC with PE/EA24. 6.Trimethylphenolhenanthren3-olFlg. 1. Procedure for the HrCT separation and subsequent GC MS analysis3.2. Mechanistic examination for the elution of arenols with PE/EAEA is a polar solvent and arenols are strongly polar compoundsas well. the most conceivable reason for the observed result is that⊥hunds with similar polarity are mutually soluble. Hydgen bonds ( HBs)played important roles in the formation of amono-hydrate [8] and in the extraction of NCOcs from coals 9The HBs of H-oo-c between the arenols and Ea should be predominantly responsible for the elution of arenols from the htctduring column chromatography with PE/EA4. ConclusionsNo HAvOcThe htCt was successfully separated to arenes and arenols byextraction with PE and subsequent column chromatograntially with PE and Pe/EA Such a separation facilitates bothA⊥catalytic hydroconversion of the arenes and subsequent fineseparation of the arenolsThis work was subsidized by the Fund from the Natural ScienceFoundation of China for Innovative Research Group(Grant50921002)and the Priority Academic Program Development ofJiangsu Higher Education Institutions.Retention time(min)Fig 2 Total ion chromatograms of the ICS. ESt. EF and EFReferences[1I Philippe C, Ronald B, Pierre E. Effect of polar components on the physico-heteroatom-containingcompounds(HAcocs)were de- (21 Zhu sY, Che FY. Wang Y. rudy on tar property from coal mild gasification Fueltected in Ef and mainThese facts indicate thatseparation of the htct tocarbon fraction and arenols-enriched fraction can be achieved by5c1M知a由AMmmsolvent extraction and subsequent column chromraphy with (41 Jia YZ Jia L The hydroxybenzene using and pick-up inCatalytic hydroconversion of coal tar to liquid fuels are being[5] wang RC, Sun M, Liu QX. Ma YX. Feng G Shangarenols and nitrogen-containing organic species(NCOCs) severely (61 2011: 34(1)34-8 temperature coal ur from Shanbei Coal Conversextensively developed in China. However, the HACOCs, includingng polar compounds in coalhnol inrum 2008: 5(1)vating the catalysts, On the other hand. most of the arenols areCJ以yL1mQ8:x273of the multi-compound non-equilibrium dissolution behaviour of avalue-added chemicals. Therefore, effective separation of the HTCTto arenes and arenols-enriched fraction(AEF) facilitates both 8 Oleg vcatalytic hydroconversion of the arenes and value-addedutilization of the AEF by subsequent fine separation.中国煤化工2x044s1mMCNMHG