煤液化残渣的组成结构分析和催化加氢
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摘要
深入了解煤液化残渣中有机质的组成结构对实现残渣的定向转化和高效利用具有重要意义。本课题选用黑山煤液化残渣（HSR）和胜利煤液化残渣（SLR）为研究对象，考察其在不同极性溶剂中的溶解性，结果表明：残渣的萃取率与溶剂的介电常数有一定的关系，两种煤液化残渣均在介电常数较大的溶剂中显示出较好的溶解性，在低介电常数范围内，萃取率随溶剂介电常数的增高而增高，在高介电常数范围内，SLR的萃取率随溶剂介电常数的增高而降低，而HSR没有此规律。依次用石油醚、甲醇、环己烷、CS_2、苯和丙酮/CS_2对HSR和SLR进行分级萃取，用GC/MS分析各级萃取物，得到了正构烷烃、长链烯烃、芳烃、酚类、酯类、酮类、醇类和其它类别的化合物（OSs）。前三级萃取物中检测到的化合物种类和含量要远远大于后三级，推测后三级萃取物中主要是大分子的缩合芳烃。
利用钌离子催化氧化（RICO）法对HSR、SLR及其萃余物和各级萃取物进行了温和条件下的氧化解聚，氧化产物经酯化后，用GC/MS和FTIR对酯化产物进行检测分析，通过比较产物组成结构的差别推测HSR和SLR的组成结构及其差异性。HSR、SLR及其萃余物和萃取物氧化反应所得可溶物的GC/MS可检测组分包括脂肪族一元酸、-二元酸、三元酸、芳酸、饱和环脂肪酸、含杂原子（氯、氧和氮）的酸及一些酮类和酯类化合物。芳酸的收率在HSR的氧化产物中占有绝对优势，而SLR的氧化产物中-二元酸的含量最高，说明HSR的缩合程度较高，而SLR中富含短链的二芳基烷烃类化合物。脂肪族一元酸和-二元酸的碳链长度较短，推测碳链较长的烷基芳烃和-二芳基烷烃为易于加氢液化的组分。在HSR和SLR萃余物的氧化产物中均检测到了一系列中长链的烷烃，碳原子分布为C13-C20，而在HSR和SLR的氧化产物中却没有检测到任何的烷烃，推测这部分烷烃化合物以网络嵌入态的形式存在于残渣的大分子结构中。SLR萃余物的氧化产物中卤代烷烃、乙氧基烷烃和短链酮类的含量较高，推测这些小分子化合物同样以网络嵌入态的形式存在于SLR的大分子结构中。前三级萃取物的氧化产物中物种较丰富，而后三级萃取物的氧化产物中主要是苯多酸。
以硅胶柱层析对SLR的CS_2萃取物进行分离分析，得到烷烃、不同缩合程度的芳烃和酯类共五个族组分。这一结果显示，溶剂萃取和柱层析技术相结合对煤液化残渣中的有机质具有良好的分离效果，可为煤液化残渣组成结构的研究和高效利用提供更加丰富的数据和信息。检测到的烷烃主要是正构烷烃，芳烃主要是4-7环的稠环芳烃，酯类主要包括长链脂肪酸甲酯和邻苯二甲酸二烷基酯。还检测到少量含氮和硫的化合物，氮和硫元素主要以环的形式存在。
在微波辐射下对脱矿物质后的HSR和SLR进行催化加氢反应，反应化合物经甲醇继续萃取两周后，用FTIR和GC/MS分析甲醇萃取物。结果表明：Pd/γ-Al2O3能有效地促进两种煤液化残渣的加氢转化；两种煤液化残渣催化加氢反应混合物中氢化芳烃、取代芳烃和非取代芳烃的收率均明显高于非催化加氢反应混合物中相应类别化合物的收率；甲醇萃余物的FTIR谱图中脂肪族成分的特征吸收峰明显减弱，表明在催化剂的作用下含-OH和链烃等官能团的小分子易从煤液化残渣的大分子结构中游离出来。
Investigating the compositions and structures in soluble organic matter from coalliquefaction residue is of great significance for both targeted conversion and efficientutilization of coal liquefaction residue. In order to investigate the organic chemicalcompositions of coal liquefaction residue, Heishan coal liquefaction residue (HSR) and Shenglicoal liquefaction residue (SLR) were selected in this subject. HSR and SLR were extractedwith petroleum ether, methanol, cyclohexane, CS_2, benzene and acetone/CS_2(1:1, V/V)sequentially and the extracts were analyzed with GC/MS. The results shows that theGC/MS-detectable species can be classified into normal alkanes, branched alkanes, alkenes,arenes, hydroxybenzenes, esters, ketones, alcohols and other species organic compounds. Thenumber of GC/MS-detectable compounds in extracts of petroleum ether, methanol andcyclohexane were appreciably more than those in extracts of CS_2, benzene and acetone/CS_2.
HSR, SLR, their extracts and extraction residues (acetone/CS_2-insoluble) were subject toruthenium ion-catalyzed oxidation (RICO). After esterification with diazomethane, theproducts were analyzed with FTIR and GC/MS. The results show that main component in theproduct from HSR is benzene carboxylic acids, however, short-chain alkanedioic acids are themost abundant species in the product from SLR, implying that HSR contains large amounts ofcondensed polyaromatic rings, and SLR contains more-diarylalkanes. The lengths ofcarbon chain of monocarboxylic acids and dicarboxylic acids are short, suggesting that theresidues are rich in condensed aromatic rings and the condensed aromatic species are insolubleand inactive toward hydroliquefaction, whereas alkylarenes and-diarylalkanes with longchain are soluble and active components toward hydroliquefaction. A series of alkanes,distribution of carbon atoms in C13-C20, were only detected in the oxidation products fromextraction residue of HSR and SLR. The yields of halogenated alkanes, ethoxy alkanes andshort chain ketones in the products from RICO of extraction residues of HSR and SLR weresignificantly higher than those from RICO of HSR and SLR.
The further separation of CS_2-extractable fraction of SLR by silica-gel columnchromatography achieved five group fractions, including alkanes, arenes (three) and esters.This result demonstrates that solvent extraction combined with column chromatography hasgood separation effect on the organic matter of coal liquefaction residue. This method canprovide more information of the compositions and structures of organic macromolecularcomponents in coal liquefaction residue and reliable theoretical basis for efficient utilization ofcoal liquefaction residue.
Demineralized HSR and SLR were subject to hydroconversion in methanol undermicrowave irradiation followed by products analysis with GC/MS. The results show thatPd/γ-Al2O3possesses good hydrogenation activity and can promote hydroconversion of coalliquefaction residue effectively; The products of hydrogenation reactions from HSR and SLRcan be classified as alkanes, hydroarenes (HAs), substituted arenes (SAs), non-substitutedarenes (NSAs), oxygen-containing organic compounds (OCOCs), and sulfur-containingorganic compounds (SCOCs). The yields of HAs, SAs and NSAs of products from catalytichydrogenations were significantly higher than those from non-catalytic hydrogenations.
利用钌离子催化氧化（RICO）法对HSR、SLR及其萃余物和各级萃取物进行了温和条件下的氧化解聚，氧化产物经酯化后，用GC/MS和FTIR对酯化产物进行检测分析，通过比较产物组成结构的差别推测HSR和SLR的组成结构及其差异性。HSR、SLR及其萃余物和萃取物氧化反应所得可溶物的GC/MS可检测组分包括脂肪族一元酸、-二元酸、三元酸、芳酸、饱和环脂肪酸、含杂原子（氯、氧和氮）的酸及一些酮类和酯类化合物。芳酸的收率在HSR的氧化产物中占有绝对优势，而SLR的氧化产物中-二元酸的含量最高，说明HSR的缩合程度较高，而SLR中富含短链的二芳基烷烃类化合物。脂肪族一元酸和-二元酸的碳链长度较短，推测碳链较长的烷基芳烃和-二芳基烷烃为易于加氢液化的组分。在HSR和SLR萃余物的氧化产物中均检测到了一系列中长链的烷烃，碳原子分布为C13-C20，而在HSR和SLR的氧化产物中却没有检测到任何的烷烃，推测这部分烷烃化合物以网络嵌入态的形式存在于残渣的大分子结构中。SLR萃余物的氧化产物中卤代烷烃、乙氧基烷烃和短链酮类的含量较高，推测这些小分子化合物同样以网络嵌入态的形式存在于SLR的大分子结构中。前三级萃取物的氧化产物中物种较丰富，而后三级萃取物的氧化产物中主要是苯多酸。
以硅胶柱层析对SLR的CS_2萃取物进行分离分析，得到烷烃、不同缩合程度的芳烃和酯类共五个族组分。这一结果显示，溶剂萃取和柱层析技术相结合对煤液化残渣中的有机质具有良好的分离效果，可为煤液化残渣组成结构的研究和高效利用提供更加丰富的数据和信息。检测到的烷烃主要是正构烷烃，芳烃主要是4-7环的稠环芳烃，酯类主要包括长链脂肪酸甲酯和邻苯二甲酸二烷基酯。还检测到少量含氮和硫的化合物，氮和硫元素主要以环的形式存在。
在微波辐射下对脱矿物质后的HSR和SLR进行催化加氢反应，反应化合物经甲醇继续萃取两周后，用FTIR和GC/MS分析甲醇萃取物。结果表明：Pd/γ-Al2O3能有效地促进两种煤液化残渣的加氢转化；两种煤液化残渣催化加氢反应混合物中氢化芳烃、取代芳烃和非取代芳烃的收率均明显高于非催化加氢反应混合物中相应类别化合物的收率；甲醇萃余物的FTIR谱图中脂肪族成分的特征吸收峰明显减弱，表明在催化剂的作用下含-OH和链烃等官能团的小分子易从煤液化残渣的大分子结构中游离出来。
Investigating the compositions and structures in soluble organic matter from coalliquefaction residue is of great significance for both targeted conversion and efficientutilization of coal liquefaction residue. In order to investigate the organic chemicalcompositions of coal liquefaction residue, Heishan coal liquefaction residue (HSR) and Shenglicoal liquefaction residue (SLR) were selected in this subject. HSR and SLR were extractedwith petroleum ether, methanol, cyclohexane, CS_2, benzene and acetone/CS_2(1:1, V/V)sequentially and the extracts were analyzed with GC/MS. The results shows that theGC/MS-detectable species can be classified into normal alkanes, branched alkanes, alkenes,arenes, hydroxybenzenes, esters, ketones, alcohols and other species organic compounds. Thenumber of GC/MS-detectable compounds in extracts of petroleum ether, methanol andcyclohexane were appreciably more than those in extracts of CS_2, benzene and acetone/CS_2.
HSR, SLR, their extracts and extraction residues (acetone/CS_2-insoluble) were subject toruthenium ion-catalyzed oxidation (RICO). After esterification with diazomethane, theproducts were analyzed with FTIR and GC/MS. The results show that main component in theproduct from HSR is benzene carboxylic acids, however, short-chain alkanedioic acids are themost abundant species in the product from SLR, implying that HSR contains large amounts ofcondensed polyaromatic rings, and SLR contains more-diarylalkanes. The lengths ofcarbon chain of monocarboxylic acids and dicarboxylic acids are short, suggesting that theresidues are rich in condensed aromatic rings and the condensed aromatic species are insolubleand inactive toward hydroliquefaction, whereas alkylarenes and-diarylalkanes with longchain are soluble and active components toward hydroliquefaction. A series of alkanes,distribution of carbon atoms in C13-C20, were only detected in the oxidation products fromextraction residue of HSR and SLR. The yields of halogenated alkanes, ethoxy alkanes andshort chain ketones in the products from RICO of extraction residues of HSR and SLR weresignificantly higher than those from RICO of HSR and SLR.
The further separation of CS_2-extractable fraction of SLR by silica-gel columnchromatography achieved five group fractions, including alkanes, arenes (three) and esters.This result demonstrates that solvent extraction combined with column chromatography hasgood separation effect on the organic matter of coal liquefaction residue. This method canprovide more information of the compositions and structures of organic macromolecularcomponents in coal liquefaction residue and reliable theoretical basis for efficient utilization ofcoal liquefaction residue.
Demineralized HSR and SLR were subject to hydroconversion in methanol undermicrowave irradiation followed by products analysis with GC/MS. The results show thatPd/γ-Al2O3possesses good hydrogenation activity and can promote hydroconversion of coalliquefaction residue effectively; The products of hydrogenation reactions from HSR and SLRcan be classified as alkanes, hydroarenes (HAs), substituted arenes (SAs), non-substitutedarenes (NSAs), oxygen-containing organic compounds (OCOCs), and sulfur-containingorganic compounds (SCOCs). The yields of HAs, SAs and NSAs of products from catalytichydrogenations were significantly higher than those from non-catalytic hydrogenations.
引文
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