胜利褐煤和新疆长焰煤中可溶有机物的分离与分析
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摘要
低阶煤的非燃料利用需要解决的主要化学问题是要对煤中有机质的组成结构有一个确切的认识。从煤的可溶物中分离和鉴定低分子量的化合物是一个非常有效的方法，通过这种方法可以更好的认识煤的结构并高效利用煤资源。为研究低阶煤中可溶物的组成，本课题选用胜利褐煤（SL）和新疆长焰煤（XCC）为原料，首先探讨了SL的苯/甲醇热溶（TD）及热溶物的分离与分析。在此基础上，选用对环境较为友好的混合溶剂甲苯/乙醇分别对SL和XCC进行超声萃取和热溶，可溶物GC/MS分析后采用柱层析和中压制备色谱的方法进行分离，分离后的各馏分通过GC/MS分析推断其组成和化合物的结构，其中从SL的苯/甲醇热溶物中分离得到的一个具有抗炎活性的化合物结合LC/MS分析进一步确证化合物的纯度和结构。
SL的甲苯/乙醇超声萃取物和热溶物的收率分别为1.7%和40.5%；XCC的超声萃取物和热溶物的收率分别为3.1%和52.4%。从两种低阶煤的可溶物的收率可以看出，以甲苯/乙醇为溶剂，不同的煤种之间XCC的超声萃取物和热溶物的收率均高于SL；而针对同一煤种的不同溶解条件，热溶物的收率远高于超声萃取物的收率，主要原因是330oC条件下SL和XCC中的大分子结构单元发生了断裂而生成了在甲苯/乙醇中易溶的小分子。
对SL和XCC各不同条件下得到的可溶物的GC/MS分析结果表明，除了在SL的苯/甲醇热溶物中只检测到9种化合物，在SL的甲苯/乙醇超声萃取物和热溶物中分别检测到41种和109种化合物，在XCC的甲苯/乙醇超声萃取物和热溶物中都检测出63种化合物，以上组成复杂的混合物尤其是热溶物中的化合物的显著特点是含氧化合物（OOCs）的相对含量占突出优势：在SL的甲苯/乙醇热溶物检测到71种OOCs，相对含量高达64.24%；XCC的甲苯/乙醇热溶物检测到37种OOCs，相对含量为53.10%。以上发现为从低阶煤中富集和分离高附加值的OOCs提供了重要的理论依据。此外，还从可溶物中发现了罕见的含磷、氯、氟和硅原子的有机物。
对各不同条件下得到的可溶物进行分离与纯化，结果从可溶组分的复杂混合物中成功分离出7种纯度较高的化合物，分别为：从SL的苯/甲醇热溶物中分离到环八硫和具有抗炎活性的6-羟基-7-异丙基-1,1,4a-三甲基-2,3,4,4a,10,10a-六氢菲-9(1H)-酮（HIPTMHHP）；从SL的甲苯/乙醇超声萃取物和热溶物中都分离得到高纯度的邻苯二甲酸二(6-甲基庚基)酯；从SL的甲苯/乙醇超声萃取物和热溶物中分别得到磷酸三丁酯和二萘甲烷；从XCC的热溶物中得到1-甲基-7-异丙基-菲和9,10-二氢-9,10,11-三甲基-9,10-亚甲基蒽-11-醇。
此外还富集到各种类型的族组分，主要包括：从各条件下得到的SL和XCC的可溶组分中都富集到一系列C14-C32范围内连续分布的正构烷烃；从SL的苯/甲醇热溶物、XCC的甲苯/乙醇超声萃取物和热溶物中都富集到主要以苯环、萘环和菲环为母体的芳烃和含氮、磷杂原子镶嵌在环内的芳香族化合物；从SL的苯/甲醇热溶物中得到15种碳数分布范围为C15-C27的长链甲基酮、12种碳数分布范围为C17-C28的长链脂肪酸乙酯、2种长链脂肪酸和4种长链脂肪酰胺；从SL的甲苯/乙醇超声萃取物中富集到3种互为同分异构体的苯甲基苯甲酸酯、18种从己基苯基碳酸酯到二十三碳烷基苯基碳酸酯连续分布的苯基碳酸酯和3种OOCs；从SL的甲苯/乙醇热溶物中富集到和其超声萃取物中相同种类的18种苯基碳酸酯以及21种从辛烷酸乙酯到二十八碳烷酸乙酯连续分布的直链脂肪酸乙酯；从XCC的超声萃取物中富集到大黄素甲醚为主成分的7种含氧化合物和结构较为复杂的3种含氮化合物（ONCs）；从XCC的甲苯/乙醇热溶物中富集到25种脂肪酸乙酯类化合物，除了20种从壬烷酸乙酯到二十八碳烷酸乙酯连续分布的直链脂肪酸乙酯，还包括3种带有甲基支链的碳烷酸乙酯和2种带有支链的烯酸乙酯。
从本论文的研究成果可以推测：选用合适的溶剂和较为温和的条件溶解低阶煤中的有机质，不仅可以从中获得高附加值的有机化学品，还可以有效的去除煤中含有的杂原子，以减少原煤直接燃烧对环境造成的污染，为低阶煤的洁净和非燃料利用都提供了切实有效的理论依据。此外，深入了解低阶煤中直接分离到和大分子断裂后的小分子的结构，可以为低阶煤的大分子结构研究提供可靠的证据。
Main chemical problem for none-fuel use of low-rank coals is to know the composition oforganic matter in the coals. Isolating and identifying the low molecular weight compound fromthe soluble fraction in coal is an effective approach for better understanding coal structure andmaking full use of coals in the future. In order to investigate the compositions of solubleorganic molecules in low-rank coals, Shengli lignite (XL), and Xinjiang Changyan Coal (XCC)were selected in this subject. Firstly, we researched the thermal dissolution (TD) of SL in abenzene/methanol then separation and analysis of its soluble matter. On this basis, SL and XCCwere undergoing ultrasonic extraction (UE) and TD in a mixed solvent toluene/ethanol friendlyto the environment. The soluble mixture was analyzed with GC/MS, and then separated bygelatin column chromatography (GCC) and medium pressure liquid chromatography (MPLC).All the subfractions after separation were analyzed with GC/MS analysis to identify theircomposition and structure. The high purity and molecular mass of a compound withanti-inflammatory activity separated from TDSL with benzene/methanol were furtherconfirmed by HPLC/MS analysis.
The yields of UESL, TDSL, UEXCC and TDXCC matter with toluene/ethanol are1.7%,40.5%,3.1%and52.4%, respectively. Seeing from the yields of the soluble matter from twodifferent low-rank coals, the yields of UEXCC and TDXCC are all obviously higher than thoseof SL’s. However, the yields of TD mixture are far greater than UE matter for the same coalunder different soluble conditions. The main reason is that soluble small molecules wereobtained after the bonds break of the macromolecule in toluene/ethanol at330oC.
The results of GC/MS analysis indicate that all kinds of compounds were detected in thesoluble matter from SL and XCC under different dissolution conditions except that only9compounds detected in TDSL with benzene/methanol.41and109compounds were detectedfrom the UESL and TDSL in toluene/ethanol, respectively. The same number,63compoundswere both detected from the UEXCC and TDXCC with toluene/ethanol. The obvious characterof the above complex mixture especially the TD matter is that the relactive content oforganoxygen compounds (OOCs) is noticably high.71OOCs were decteted and the relativecontent are64.24%from TDSL with toluene/ethanol.37OOCs were decteted and the relativecontent are53.10%from TDXCC with toluene/ethanol. This gave us important theoreticalevidence to investigate the possibility for separating and enriching some OOCs from low-rankcoals. What’s more, some unusual phosphorus, fluorine and silicon-containing compoundswere detected in the soluble matter.
With further isolation and purification of each soluble matter,7compounds with highpurity were separated successfully and identified as octathiocane and6-hydroxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,4a,10,10a-hexahydrophenanthren-9(1H)-one(HIPTMHHP) with anti-inflammatory activity from TDSL in benzene/methanol,bis(6-methylheptyl)phthalate from UESL and TDSL in toluene/ethanol, tributyl phosphate and(naphthalen-1-yl)(naphthalen-2-yl) methane from UESL and TDSL with toluene/ethanol,respectively,1-methyl-7-isopropylphenanthrene and9,10-dihydro-9,10,11-trimethyl-9,10-methanoanthracen-11-ol from XCCTD.
Further more, all kinds of group fractions were enriched and they mainly include: a seriesof normal normal alkanes in the range of C14-C32from every soluble matter of SL and XCC,various types of aromatics mainly including parent body of benzene-, naphthalene-andphenanthrene-ring and some heteratom atoms like nitrogen and phosphorus from TDSL withbenzene/methanol and XCCUE and TDXCC with toluene/ethanol,15methyl alkanones in rherange of C15-C27, methyl alkanoates of C17-C28,2alkanoic acids and4fatty acid amides fromTDSL with benzene/ethanol,18phenylcarbonates of C6-C23from UESL and TDSL withtoluene/ethanol,3tolyl benzoates isomers of each other and3OOCs from UESL withtoluene/ethanol,7OOCs mainly including physcion from UEXCC,3organonitrogencompounds (ONCs) with complex structure from UEXCC,21straight-chain ethyl alkanoatesfrom TDSL with toluene/ethanol,25ethyl alkanoates including20straight-chain ethylalkanoates,3side-chain ethyl alkanoates and2side-chain ethyl esters olefine acid fromTDXCC with toluene/ethanol.
By dissolving the low-rank coals with suitable solvents at mild conditions, we can obtainsome high-valued organic chemicals and effectively remove the heteratom-containing organiccompounds to reduce their pollutions to the environment when coals are combusted directly.This could provide effective theoretical basis for clean and non-fuel use of low-rank coals.Further, probing deeply into the structure of small moleculars from direction separation andbonds break of the macromolecule could also give reliable evidences for research on thestructure of macromolecule in low-rank coals.
SL的甲苯/乙醇超声萃取物和热溶物的收率分别为1.7%和40.5%；XCC的超声萃取物和热溶物的收率分别为3.1%和52.4%。从两种低阶煤的可溶物的收率可以看出，以甲苯/乙醇为溶剂，不同的煤种之间XCC的超声萃取物和热溶物的收率均高于SL；而针对同一煤种的不同溶解条件，热溶物的收率远高于超声萃取物的收率，主要原因是330oC条件下SL和XCC中的大分子结构单元发生了断裂而生成了在甲苯/乙醇中易溶的小分子。
对SL和XCC各不同条件下得到的可溶物的GC/MS分析结果表明，除了在SL的苯/甲醇热溶物中只检测到9种化合物，在SL的甲苯/乙醇超声萃取物和热溶物中分别检测到41种和109种化合物，在XCC的甲苯/乙醇超声萃取物和热溶物中都检测出63种化合物，以上组成复杂的混合物尤其是热溶物中的化合物的显著特点是含氧化合物（OOCs）的相对含量占突出优势：在SL的甲苯/乙醇热溶物检测到71种OOCs，相对含量高达64.24%；XCC的甲苯/乙醇热溶物检测到37种OOCs，相对含量为53.10%。以上发现为从低阶煤中富集和分离高附加值的OOCs提供了重要的理论依据。此外，还从可溶物中发现了罕见的含磷、氯、氟和硅原子的有机物。
对各不同条件下得到的可溶物进行分离与纯化，结果从可溶组分的复杂混合物中成功分离出7种纯度较高的化合物，分别为：从SL的苯/甲醇热溶物中分离到环八硫和具有抗炎活性的6-羟基-7-异丙基-1,1,4a-三甲基-2,3,4,4a,10,10a-六氢菲-9(1H)-酮（HIPTMHHP）；从SL的甲苯/乙醇超声萃取物和热溶物中都分离得到高纯度的邻苯二甲酸二(6-甲基庚基)酯；从SL的甲苯/乙醇超声萃取物和热溶物中分别得到磷酸三丁酯和二萘甲烷；从XCC的热溶物中得到1-甲基-7-异丙基-菲和9,10-二氢-9,10,11-三甲基-9,10-亚甲基蒽-11-醇。
此外还富集到各种类型的族组分，主要包括：从各条件下得到的SL和XCC的可溶组分中都富集到一系列C14-C32范围内连续分布的正构烷烃；从SL的苯/甲醇热溶物、XCC的甲苯/乙醇超声萃取物和热溶物中都富集到主要以苯环、萘环和菲环为母体的芳烃和含氮、磷杂原子镶嵌在环内的芳香族化合物；从SL的苯/甲醇热溶物中得到15种碳数分布范围为C15-C27的长链甲基酮、12种碳数分布范围为C17-C28的长链脂肪酸乙酯、2种长链脂肪酸和4种长链脂肪酰胺；从SL的甲苯/乙醇超声萃取物中富集到3种互为同分异构体的苯甲基苯甲酸酯、18种从己基苯基碳酸酯到二十三碳烷基苯基碳酸酯连续分布的苯基碳酸酯和3种OOCs；从SL的甲苯/乙醇热溶物中富集到和其超声萃取物中相同种类的18种苯基碳酸酯以及21种从辛烷酸乙酯到二十八碳烷酸乙酯连续分布的直链脂肪酸乙酯；从XCC的超声萃取物中富集到大黄素甲醚为主成分的7种含氧化合物和结构较为复杂的3种含氮化合物（ONCs）；从XCC的甲苯/乙醇热溶物中富集到25种脂肪酸乙酯类化合物，除了20种从壬烷酸乙酯到二十八碳烷酸乙酯连续分布的直链脂肪酸乙酯，还包括3种带有甲基支链的碳烷酸乙酯和2种带有支链的烯酸乙酯。
从本论文的研究成果可以推测：选用合适的溶剂和较为温和的条件溶解低阶煤中的有机质，不仅可以从中获得高附加值的有机化学品，还可以有效的去除煤中含有的杂原子，以减少原煤直接燃烧对环境造成的污染，为低阶煤的洁净和非燃料利用都提供了切实有效的理论依据。此外，深入了解低阶煤中直接分离到和大分子断裂后的小分子的结构，可以为低阶煤的大分子结构研究提供可靠的证据。
Main chemical problem for none-fuel use of low-rank coals is to know the composition oforganic matter in the coals. Isolating and identifying the low molecular weight compound fromthe soluble fraction in coal is an effective approach for better understanding coal structure andmaking full use of coals in the future. In order to investigate the compositions of solubleorganic molecules in low-rank coals, Shengli lignite (XL), and Xinjiang Changyan Coal (XCC)were selected in this subject. Firstly, we researched the thermal dissolution (TD) of SL in abenzene/methanol then separation and analysis of its soluble matter. On this basis, SL and XCCwere undergoing ultrasonic extraction (UE) and TD in a mixed solvent toluene/ethanol friendlyto the environment. The soluble mixture was analyzed with GC/MS, and then separated bygelatin column chromatography (GCC) and medium pressure liquid chromatography (MPLC).All the subfractions after separation were analyzed with GC/MS analysis to identify theircomposition and structure. The high purity and molecular mass of a compound withanti-inflammatory activity separated from TDSL with benzene/methanol were furtherconfirmed by HPLC/MS analysis.
The yields of UESL, TDSL, UEXCC and TDXCC matter with toluene/ethanol are1.7%,40.5%,3.1%and52.4%, respectively. Seeing from the yields of the soluble matter from twodifferent low-rank coals, the yields of UEXCC and TDXCC are all obviously higher than thoseof SL’s. However, the yields of TD mixture are far greater than UE matter for the same coalunder different soluble conditions. The main reason is that soluble small molecules wereobtained after the bonds break of the macromolecule in toluene/ethanol at330oC.
The results of GC/MS analysis indicate that all kinds of compounds were detected in thesoluble matter from SL and XCC under different dissolution conditions except that only9compounds detected in TDSL with benzene/methanol.41and109compounds were detectedfrom the UESL and TDSL in toluene/ethanol, respectively. The same number,63compoundswere both detected from the UEXCC and TDXCC with toluene/ethanol. The obvious characterof the above complex mixture especially the TD matter is that the relactive content oforganoxygen compounds (OOCs) is noticably high.71OOCs were decteted and the relativecontent are64.24%from TDSL with toluene/ethanol.37OOCs were decteted and the relativecontent are53.10%from TDXCC with toluene/ethanol. This gave us important theoreticalevidence to investigate the possibility for separating and enriching some OOCs from low-rankcoals. What’s more, some unusual phosphorus, fluorine and silicon-containing compoundswere detected in the soluble matter.
With further isolation and purification of each soluble matter,7compounds with highpurity were separated successfully and identified as octathiocane and6-hydroxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,4a,10,10a-hexahydrophenanthren-9(1H)-one(HIPTMHHP) with anti-inflammatory activity from TDSL in benzene/methanol,bis(6-methylheptyl)phthalate from UESL and TDSL in toluene/ethanol, tributyl phosphate and(naphthalen-1-yl)(naphthalen-2-yl) methane from UESL and TDSL with toluene/ethanol,respectively,1-methyl-7-isopropylphenanthrene and9,10-dihydro-9,10,11-trimethyl-9,10-methanoanthracen-11-ol from XCCTD.
Further more, all kinds of group fractions were enriched and they mainly include: a seriesof normal normal alkanes in the range of C14-C32from every soluble matter of SL and XCC,various types of aromatics mainly including parent body of benzene-, naphthalene-andphenanthrene-ring and some heteratom atoms like nitrogen and phosphorus from TDSL withbenzene/methanol and XCCUE and TDXCC with toluene/ethanol,15methyl alkanones in rherange of C15-C27, methyl alkanoates of C17-C28,2alkanoic acids and4fatty acid amides fromTDSL with benzene/ethanol,18phenylcarbonates of C6-C23from UESL and TDSL withtoluene/ethanol,3tolyl benzoates isomers of each other and3OOCs from UESL withtoluene/ethanol,7OOCs mainly including physcion from UEXCC,3organonitrogencompounds (ONCs) with complex structure from UEXCC,21straight-chain ethyl alkanoatesfrom TDSL with toluene/ethanol,25ethyl alkanoates including20straight-chain ethylalkanoates,3side-chain ethyl alkanoates and2side-chain ethyl esters olefine acid fromTDXCC with toluene/ethanol.
By dissolving the low-rank coals with suitable solvents at mild conditions, we can obtainsome high-valued organic chemicals and effectively remove the heteratom-containing organiccompounds to reduce their pollutions to the environment when coals are combusted directly.This could provide effective theoretical basis for clean and non-fuel use of low-rank coals.Further, probing deeply into the structure of small moleculars from direction separation andbonds break of the macromolecule could also give reliable evidences for research on thestructure of macromolecule in low-rank coals.
引文
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