煤在NaOCl水溶液中的选择性氧化和产物的精细分离
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摘要
煤是重要的重质碳资源,其清洁和高效利用对于我国国民经济的可持续发展具有重要意义,而清洁和高效利用的关键是对其结构的充分了解。氧化解聚是研究煤的有机质大分子网络结构及从中获取有机化合物的重要技术。在温和条件下适度和选择性地氧化解聚煤,尽可能多的将其所含有机质转化为组成比较简单的有机化合物,并揭示氧化解聚反应的机理,是全面了解煤的组成结构特征、建立有效分离和分析反应混合物的科学方法,最终实现对煤的高附加值利用的关键。而NaOCl水溶液不但是廉价、易得、环境友好的氧化剂,更为重要的是它对煤中有机质具有良好的解聚活性和较高选择性,因此煤的NaOCl氧化解聚是一条值得探索的煤高效利用之路。
本课题研究了4种不同变质程度的煤和一系列煤模型化合物(CRMCs)在NaOCl水溶液中的氧化解聚反应,通过对反应过程的优化、产物的分离和分析及反应机理的考察,为煤的高附加值利用提供可靠的理论依据和技术支撑,并得出以下主要结论:通过对煤与NaOCl水溶液用量的配比、反应温度、反应时间及pH值等多种因素对煤氧化解聚的影响,发现褐煤较烟煤易反应。确定褐煤的最佳氧化解聚条件为:煤/NaOCl用量的配比为1/100(g/mL),初始pH值为12.0左右于30 oC下反应24h左右;烟煤的最佳氧化解聚条件为煤/NaOCl用量配比为1/120(g/mL),初始pH值为10.5左右于40oC下反应36h左右。
利用GC/MS对煤氧化解聚产物进行分析,发现煤的解聚产物非常复杂,氯代物、脂肪酸和芳酸是煤氧化的典型物质。通过依次用五种不同极性溶剂对煤氧化所得水溶物的萃取,实现了氧化产物族组分的初步分离。乙醚和EA可以对极性较大的含氧及含氯有机物进行富集;CS_2可以有效萃取有机硫化合物和烷烃,PE对极性小的烃类化合物萃取率较高,苯对烃和酯的萃取率均较高;在盐中苯环上羧基数超过4个的苯多酸含量较高。
依次用乙醚、CS_2和甲醇对三种煤氧化所得固体酸(FC_2)进行超声萃取,结果表明对FC_2的萃取率按甲醇、乙醚和CS_2的顺序递减。用NaOCl水溶液对FC_2进行二次氧化,发现氧化产物与其原煤的氧化产物相比,所得产物主要是苯环上含4个羧基以上的苯多酸,同时化合物种类大大减少,这说明FC_2结构以高度缩合的芳环为主。
依次用PE、CS_2、丙酮和甲醇4种溶剂对4种煤的氧化残煤(FC1)进行索式萃取,发现甲醇的萃取率最高。利用GC/MS对各级萃取物进行分析,发现东滩和黑岱沟煤FC1的PE萃取物及所有丙酮和甲醇萃取物中均无GC/MS可检测信息。其余萃取物中所检测到的化合物主要以含氧化合物、芳烃和烷烃为主。
通过“分级萃取-柱层析分离-重结晶”对煤的NaOCl水溶液氧化解聚产物进行了精细分离,得到了8种苯多酸甲酯纯品,并且其同分异构体也得到了有效分离。实现了煤氧化部分产物的精细分离,为从天然大分子化合物中制备苯多酸提供了一种新的切实可行的方法,同时也为实现煤的高附加值利用提供了重要的技术手段。
通过考察CRMCs与NaOCl水溶液的反应,发现NaOCl水溶液几乎可以与各种类型化合物发生反应,反应机理比较复杂,存在氧化、加成、取代和自由基等多种竞争反应。苯环较稳定不易被氧化,侧链比苯环更易氧化;稠环芳烃(包括萘环)比苯环活泼,而且比侧链具有更强的反应性;同时稠芳环上的取代基对其氧化开环方式起重要的影响作用;烷烃与NaOCl的反应性较弱,CCl_4的加入能大大提高其反应性,因此推断烷烃与NaOCl反应可能以自由基反应机理进行;含氧化合物与NaOCl比较容易反应;含氮和硫化合物中的氮和硫原子易被氧化为相应的氮氧和硫氧化合物,且与其相连的键易发生氧化断裂。并在此基础上进一步探讨了煤的反应机理。
该论文有图132幅,表67个,参考文献230篇
As important heavy carbon resource, efficient utilization of coal is very important to thesustainable development of our national economy, while the key to effective use is ofknowledgeofitsstructure.Coaloxidationisanimportantapproachforbothunderstandingcoalorganic matter macromolecular network structure and obtaining organic chemicals. Theresearches of under mild conditions in moderate and selective depolymerization of organicmatter in coal as much as possible for the composition of simple organic compounds andoxidativedepolymerizationmechanism are helpfultounderstandcoalstructuralcharacteristics,establish an scientific method of separation and analysis for products and prepare highvalue-added products from coal.Comparedtoother oxidants,NaOClhas someobvious merits,such as cheaper, easy availability, environmental friendly, and higher reactivity toward coaloxidative degradation. These merits, especially for the high reactivity toward coal oxidativedegradation, possibly make coal oxidated under mild conditions, thereforecoal oxidation withNaOClisaworthwhilewaytoexploretheefficientuseofcoal.
To provide a reliable theoretical basis and technical support for high value-added utilizationofcoal,oxidativedegradationbehaviors offourdifferent rankcoals anda series ofcoal relatedmodel compounds (CRMCs) with aqueous NaOCl solution, including the reaction processoptimization, separation and analysis of oxidation products and the reaction mechanism, wereinvestigatedinthisstudy.Themainresultsinthisworkareasfollows:
The effects of ratio of NaOCl to coal, reaction temperature, pH value and reaction time onthe coal oxidative degradation were investigated. The results show that lignite was more easilyreactive than bituminous coal. The optimum operation conditions for lignite oxidativedegradation are 30 oC, pH, 12.0, NaOCl/coal 1/100 (g/mL) and 24 h and forbituminous coaloxidativedegradationare 40oC,pH10.5,NaOCl/coal1:120(g/mL)and 36h.
Coal oxidation products were analyzed with GC/MS. The results indicated that the productswere very complex, and chlorinated compounds, fatty acids, aromatic acids were typical coaloxidation substances. Oxidative product was sequentially extracted with five different polarsolvents and achieved a simple group separation. Oxygen-containing and chlorine-containingorganic compounds could be enriched with ether and ethyl acetate, and the extracts of CS_2contained a large amounts of organic sulfur compounds and alkanes, and hydrocarbons withsmall polar were the main components of petroleum ether, and benzene on the extraction ofhydrocarbons and esters were high extracts, and the content of benzene polycarboxylic acidswithmorethanfourcarboxylicgroupsattachedtobenzenewerehighinsalt.
Three solid acids (FC_2) produced from coal oxidation were extracted with ether, CS_2 and methanol sequentially under ultrasonic. It is found that the extraction yield of methanolon thethreesolidacidswashighest,followedbyether,andCS_2 wasminimum.FC_2wasoxidized withNaOCl. The results showed that the kinds of compounds in the oxidative products of FC_2greatly reduced compared with those of raw coal. The compounds were mainly benzenepolycarboxylic acids with more than four carboxy. It is indicated that the structure of FC_2 wasahighercondensedaromaticrings.
Four coal oxidation residues (FC1) were extracted with petroleum ether, CS_2, acetone andmethanol underSoxhlet,sequentially.Theextractionyieldofmethanolishighest.BasedontheGC/MS anaysis ofextracts, it is foundthat nonecompounds weredetected from theextracts ofpetroleum ether from Dongtan and Heidaigou oxidation residues and the extracts of acetoneand methanol from all four oxidation residues. The main compounds detected in other extractswereoxygen-containingcompounds,aromaticsandalkanes.
Using graded extraction-separation with column chromatography-crystallization technologyto subtly separate the oxidation products, eight kinds of pure methyl benzene polycarboxylicacids were obtained, and their isomers were also effective separated. It is achieved partialoxidation products of the fine coal separation, which provides a new feasible method forobtainingbenzenepolycarboxylicacidsfromnaturalmacromoleculesmaterials, andprovidesanimportanttechnologyforhighvalue-addeduseofcoal.
It was found that NaOCl can react with almost all types of compounds by examiningCRMCs reaction with NaOCl. The reaction mechanism is complex due to the presence ofmany competitive reactions, such as oxidation, addition, substitution, and free radicals. Theside chain on the benzene ring is oxidized rather than the benzene ring itself; polycyclicaromatic hydrocarbons (including naphthalene) are more reactive toward NaOCl than sidechain; substituentsonthearomaticringplaysanimportantwaytoinfluenceontheoxidationofaromatic ring; the reactivity of alkane with NaOCl is weak, while it is greatly enhanced byCCl4 addded, so the mechanism of alkane reaction with NaOCl may be by free radical;oxygenated compounds easily react with NaOCl; organic nitrogen and sulfur compounds areeasily oxidized to the corresponding nitrogen oxide and sulfur oxides, and their associatedbondswereeasilybroken.ThemechanismsofcoaloxidationwithNaOClwerealsodiscussed.
132figures,67tables,230 references.
本课题研究了4种不同变质程度的煤和一系列煤模型化合物(CRMCs)在NaOCl水溶液中的氧化解聚反应,通过对反应过程的优化、产物的分离和分析及反应机理的考察,为煤的高附加值利用提供可靠的理论依据和技术支撑,并得出以下主要结论:通过对煤与NaOCl水溶液用量的配比、反应温度、反应时间及pH值等多种因素对煤氧化解聚的影响,发现褐煤较烟煤易反应。确定褐煤的最佳氧化解聚条件为:煤/NaOCl用量的配比为1/100(g/mL),初始pH值为12.0左右于30 oC下反应24h左右;烟煤的最佳氧化解聚条件为煤/NaOCl用量配比为1/120(g/mL),初始pH值为10.5左右于40oC下反应36h左右。
利用GC/MS对煤氧化解聚产物进行分析,发现煤的解聚产物非常复杂,氯代物、脂肪酸和芳酸是煤氧化的典型物质。通过依次用五种不同极性溶剂对煤氧化所得水溶物的萃取,实现了氧化产物族组分的初步分离。乙醚和EA可以对极性较大的含氧及含氯有机物进行富集;CS_2可以有效萃取有机硫化合物和烷烃,PE对极性小的烃类化合物萃取率较高,苯对烃和酯的萃取率均较高;在盐中苯环上羧基数超过4个的苯多酸含量较高。
依次用乙醚、CS_2和甲醇对三种煤氧化所得固体酸(FC_2)进行超声萃取,结果表明对FC_2的萃取率按甲醇、乙醚和CS_2的顺序递减。用NaOCl水溶液对FC_2进行二次氧化,发现氧化产物与其原煤的氧化产物相比,所得产物主要是苯环上含4个羧基以上的苯多酸,同时化合物种类大大减少,这说明FC_2结构以高度缩合的芳环为主。
依次用PE、CS_2、丙酮和甲醇4种溶剂对4种煤的氧化残煤(FC1)进行索式萃取,发现甲醇的萃取率最高。利用GC/MS对各级萃取物进行分析,发现东滩和黑岱沟煤FC1的PE萃取物及所有丙酮和甲醇萃取物中均无GC/MS可检测信息。其余萃取物中所检测到的化合物主要以含氧化合物、芳烃和烷烃为主。
通过“分级萃取-柱层析分离-重结晶”对煤的NaOCl水溶液氧化解聚产物进行了精细分离,得到了8种苯多酸甲酯纯品,并且其同分异构体也得到了有效分离。实现了煤氧化部分产物的精细分离,为从天然大分子化合物中制备苯多酸提供了一种新的切实可行的方法,同时也为实现煤的高附加值利用提供了重要的技术手段。
通过考察CRMCs与NaOCl水溶液的反应,发现NaOCl水溶液几乎可以与各种类型化合物发生反应,反应机理比较复杂,存在氧化、加成、取代和自由基等多种竞争反应。苯环较稳定不易被氧化,侧链比苯环更易氧化;稠环芳烃(包括萘环)比苯环活泼,而且比侧链具有更强的反应性;同时稠芳环上的取代基对其氧化开环方式起重要的影响作用;烷烃与NaOCl的反应性较弱,CCl_4的加入能大大提高其反应性,因此推断烷烃与NaOCl反应可能以自由基反应机理进行;含氧化合物与NaOCl比较容易反应;含氮和硫化合物中的氮和硫原子易被氧化为相应的氮氧和硫氧化合物,且与其相连的键易发生氧化断裂。并在此基础上进一步探讨了煤的反应机理。
该论文有图132幅,表67个,参考文献230篇
As important heavy carbon resource, efficient utilization of coal is very important to thesustainable development of our national economy, while the key to effective use is ofknowledgeofitsstructure.Coaloxidationisanimportantapproachforbothunderstandingcoalorganic matter macromolecular network structure and obtaining organic chemicals. Theresearches of under mild conditions in moderate and selective depolymerization of organicmatter in coal as much as possible for the composition of simple organic compounds andoxidativedepolymerizationmechanism are helpfultounderstandcoalstructuralcharacteristics,establish an scientific method of separation and analysis for products and prepare highvalue-added products from coal.Comparedtoother oxidants,NaOClhas someobvious merits,such as cheaper, easy availability, environmental friendly, and higher reactivity toward coaloxidative degradation. These merits, especially for the high reactivity toward coal oxidativedegradation, possibly make coal oxidated under mild conditions, thereforecoal oxidation withNaOClisaworthwhilewaytoexploretheefficientuseofcoal.
To provide a reliable theoretical basis and technical support for high value-added utilizationofcoal,oxidativedegradationbehaviors offourdifferent rankcoals anda series ofcoal relatedmodel compounds (CRMCs) with aqueous NaOCl solution, including the reaction processoptimization, separation and analysis of oxidation products and the reaction mechanism, wereinvestigatedinthisstudy.Themainresultsinthisworkareasfollows:
The effects of ratio of NaOCl to coal, reaction temperature, pH value and reaction time onthe coal oxidative degradation were investigated. The results show that lignite was more easilyreactive than bituminous coal. The optimum operation conditions for lignite oxidativedegradation are 30 oC, pH, 12.0, NaOCl/coal 1/100 (g/mL) and 24 h and forbituminous coaloxidativedegradationare 40oC,pH10.5,NaOCl/coal1:120(g/mL)and 36h.
Coal oxidation products were analyzed with GC/MS. The results indicated that the productswere very complex, and chlorinated compounds, fatty acids, aromatic acids were typical coaloxidation substances. Oxidative product was sequentially extracted with five different polarsolvents and achieved a simple group separation. Oxygen-containing and chlorine-containingorganic compounds could be enriched with ether and ethyl acetate, and the extracts of CS_2contained a large amounts of organic sulfur compounds and alkanes, and hydrocarbons withsmall polar were the main components of petroleum ether, and benzene on the extraction ofhydrocarbons and esters were high extracts, and the content of benzene polycarboxylic acidswithmorethanfourcarboxylicgroupsattachedtobenzenewerehighinsalt.
Three solid acids (FC_2) produced from coal oxidation were extracted with ether, CS_2 and methanol sequentially under ultrasonic. It is found that the extraction yield of methanolon thethreesolidacidswashighest,followedbyether,andCS_2 wasminimum.FC_2wasoxidized withNaOCl. The results showed that the kinds of compounds in the oxidative products of FC_2greatly reduced compared with those of raw coal. The compounds were mainly benzenepolycarboxylic acids with more than four carboxy. It is indicated that the structure of FC_2 wasahighercondensedaromaticrings.
Four coal oxidation residues (FC1) were extracted with petroleum ether, CS_2, acetone andmethanol underSoxhlet,sequentially.Theextractionyieldofmethanolishighest.BasedontheGC/MS anaysis ofextracts, it is foundthat nonecompounds weredetected from theextracts ofpetroleum ether from Dongtan and Heidaigou oxidation residues and the extracts of acetoneand methanol from all four oxidation residues. The main compounds detected in other extractswereoxygen-containingcompounds,aromaticsandalkanes.
Using graded extraction-separation with column chromatography-crystallization technologyto subtly separate the oxidation products, eight kinds of pure methyl benzene polycarboxylicacids were obtained, and their isomers were also effective separated. It is achieved partialoxidation products of the fine coal separation, which provides a new feasible method forobtainingbenzenepolycarboxylicacidsfromnaturalmacromoleculesmaterials, andprovidesanimportanttechnologyforhighvalue-addeduseofcoal.
It was found that NaOCl can react with almost all types of compounds by examiningCRMCs reaction with NaOCl. The reaction mechanism is complex due to the presence ofmany competitive reactions, such as oxidation, addition, substitution, and free radicals. Theside chain on the benzene ring is oxidized rather than the benzene ring itself; polycyclicaromatic hydrocarbons (including naphthalene) are more reactive toward NaOCl than sidechain; substituentsonthearomaticringplaysanimportantwaytoinfluenceontheoxidationofaromatic ring; the reactivity of alkane with NaOCl is weak, while it is greatly enhanced byCCl4 addded, so the mechanism of alkane reaction with NaOCl may be by free radical;oxygenated compounds easily react with NaOCl; organic nitrogen and sulfur compounds areeasily oxidized to the corresponding nitrogen oxide and sulfur oxides, and their associatedbondswereeasilybroken.ThemechanismsofcoaloxidationwithNaOClwerealsodiscussed.
132figures,67tables,230 references.
引文
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