碳纳米管及掺氮碳纳米管液相催化氧化苯甲醇和乙苯
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摘要
碳纳米管具有比表面积高、环境兼容、抗酸碱、易回收活性组分贵金属、在非氧条件下热稳定性高和易对其进行表面改性和功能化等优点，是一种优异的催化新材料，在催化领域日益受到重视，被广泛用作催化剂载体和非金属催化剂。目前，碳纳米管及掺氮碳纳米管作为非金属催化剂在气相氧化脱氢和氧还原等方面的研究较为系统和成熟，然而，在液相选择性催化氧化方面的研究不够深入。因此，拓宽碳纳米管及掺氮碳纳米管在液相选择性催化氧化方面的应用，特别是探索其在不同液相反应体系中的反应机理是一个非常有科学意义与重要应用价值的研究课题。本论文创新性的探索碳纳米管及掺氮碳纳米管在含有自由基或不含自由基的液相选择性氧化反应中的催化性能，发展在温和条件下利用碳纳米管及掺氮碳纳米管在分子氧（氧气）条件下，催化氧化苯甲醇（非自由基反应）和乙苯（自由基反应）制备高附加值化学产品苯甲醛和苯乙酮的绿色催化新方法；针对碳纳米管新材料在液相催化氧化过程中的应用，研究其表面基团、表面结构对液相催化氧化苯甲醇和乙苯的作用规律，提出合理的反应机理，为推动碳材料在液相选择性氧化反应中的应用提供重要理论依据。主要内容如下：
（1）采用化学气相沉积法成功制备了碳纳米管和掺氮碳纳米管并对它们进行了系统表征。结果表明：采用液化气为碳源制备的碳纳米管平均外径和内径分别为20.8nm和6.6nm，而采用二甲苯为碳源制备的碳纳米管平均外径和内径分别为33.5nm和7.7nm。采用二甲苯为碳源、苯胺为氮源制备的掺氮碳纳米管外径和内径分别为29-40nm和10-14nm。掺氮碳纳米管的总掺氮含量随前驱物苯胺量的增加而增加，总掺氮含量在0.3at.%-3.11at.%之间，其中吡啶氮含量和季氮含量随前驱物苯胺量的增加而增加，而吡咯氮含量却随前驱物苯胺量的增加呈先增后减的趋势。向碳纳米管晶格中掺入氮原子并没有破坏其石墨化结构，但增加了其表面缺陷度，且缺陷度随总掺氮含量的增加而增大。掺氮碳纳米管与碳纳米管相比热稳定性稍有下降，但在500oC以下无明显失重，热稳定性好。
（2）研究了碳纳米管催化分子氧液相氧化乙苯生成苯乙酮的反应条件、结构与性能关系以及可能的反应机理。结果表明：(a)在155oC、催化剂与乙苯物质的量的比为0.2和1.5MPa O2条件下反应4h后，碳纳米管能获得38.2%乙苯转化率和60.9%苯乙酮选择性。(b)碳纳米管催化分子氧氧化乙苯反应是一个自由基反应，苯乙基过氧化氢的分解在反应中自由基链的传递和产物苯乙酮的生成起着非常重要的作用，而碳纳米管中石墨片的大π电子转移能力在苯乙基过氧化氢的分解反应过程中可能起着关键的作用。(c)碳纳米管残留的金属Fe杂质不是乙苯氧化反应的活性中心。(d)碳纳米管表面缺陷和羧基对其催化分子氧氧化乙苯反应有不利的影响，且碳纳米管的催化活性随其表面羧基量的增加而迅速降低。这是因为向碳纳米管表面引入羧基后，由于氧原子电负性大于碳原子，表现出吸电子性质，造成局部的π电子不能很好的在石墨片层中离域，从而不利于含有羧基的碳纳米管的大π电子与苯乙基过氧化氢中间体发生π-π共轭作用，故催化活性降低。(e)碳纳米管作为催化剂在选择性催化分子氧氧化乙苯制备苯乙酮反应中表现出较高的稳定性，在连续重复5次后，能获得36.3%乙苯转化率和60.6%苯乙酮选择性，是一种很有应用前景的新型催化剂。(f)向碳纳米管掺杂非金属氮原子对其催化分子氧氧化乙苯反应有不利的影响，这是因为向碳纳米管晶格中掺入非金属的氮原子，增加了其表面缺陷，可能降低了掺氮碳纳米管的导电性和电子流动性，在一定程度上抑制了电子转移能力，不利于碳纳米管的石墨片层和自由基及过氧化物之间的π-π共轭作用，故催化活性降低。
（3）研究了碳纳米管和掺氮碳纳米管在催化分子氧氧化苯甲醇反应中的催化性能与作用机制。结果表明：(a)不论碳纳米管，还是掺氮碳纳米管单独作为催化剂，在常压90oC反应5h后都只能获得低于10%的苯甲醇转化率，活性较低；添加硝酸助剂后，相同条件下碳纳米管能获得96.2%的苯甲醇转化率和88.3%的苯甲醛选择性。但是，在没有碳纳米管的存在下，硝酸本身作为化学计量氧化剂不能高效的催化氧化苯甲醇，只能获得31.4%的苯甲醇转化率和75.3%的苯甲醛选择性。(b)碳纳米管催化分子氧氧化苯甲醇反应是一个非自由基反应，亚硝酸苄酯是硝酸助碳纳米管催化分子氧氧化苯甲醇反应的重要中间体，分子氧是消耗的氧化剂，而硝酸只是引发催化循环的一个引发剂。(c)碳纳米管残留的金属杂质不是苯甲醇氧化反应的活性中心，而碳纳米管中石墨片的大π电子转移能力在反应中起着非常重要的作用。(d)碳纳米管表面缺陷和含氧基团对苯甲醇转化率的影响较小。(e)向碳纳米管晶格中掺入适量的氮原子，能提高其催化活性，但一旦掺入过量的氮原子，反而降低其催化活性。当向碳纳米管晶格中掺入1.02at.%氮原子时，能获得最高的催化活性，即在常压90oC反应3h后能获得78.5%的苯甲醛产率；而未掺氮的碳纳米管在同样条件下只能获得68.2%的苯甲醛产率，这是因为向碳纳米管晶格中掺入适量的带有孤对电子的氮原子在一定程度上能增强碳纳米管中石墨片的大π电子转移能力，进而增强其与反应中间体亚硝酸苄酯的π-π共轭作用，有利于中间体亚硝酸苄酯的分解，从而增强其催化活性。(f)碳纳米管及掺氮碳纳米管作为催化剂在选择性催化分子氧液相氧化苯甲醇制备苯甲醛反应中均表现出较高的稳定性，是一类很有应用前景的新型催化剂。
Carbon nanotubes (CNTs) as catalyst supports and metal-free catalysts have attractedmuch attentions, owing to their unique physicochemical properties such as high specifcsurface areas, environmental acceptability, corrosion resistance, easy recovery of preciousmetals by support burning, thermal stability under nonoxidative condition and readily surfacemodifcation. At present, most of the studies on CNTs and nitrogen-doped carbon nanotubes(NCNTs) as metal-free catalysts have focused on the oxygen reduction reaction and gas phaseoxidative dehydrogenation reaction. However, it is rarely reported on selective liquid phaseoxidation reaction. In order to enlarge their application, the research on reaction mechanismof different liquid phase oxidation reactions is of great scientific and practical significance. Inthis thesis, the free radical or not free radical oxidation reactions catalyzed by CNTs andNCNTs were investigated, that is, selective liquid phase oxidation of benzyl alcohol orethylbenzene (EB) catalyzed by CNTs and NCNTs to prepare highly valuable chemicalproducts benzaldehyde or acetophenone (AcPO), respectively, under the mild reactionconditions. This study can reduce traditional catalysis dependency on precious and transitionmetals and reduce environment impact from great quantities of waste. Moreover, the effectsof surface oxygen functional groups and surface structure of carbon materials on the catalyticactivity of selective liquid phase oxidation of benzyl alcohol or EB were investigated andplausible catalytic mechanisms of the benzyl alcohol or EB aerobic oxidation were proposed.These results can provide important theoretical basis for promoting carbon materials’application in selective liquid phase oxidation reactions. The main contents are described asfollows:
(1) CNTs and NCNTs were successfully prepared by the chemical vapor deposition(CVD) method. The results are showed as follows:(a) The CNTs were prepared by CVD withliquefied petroleum gas as carbon source over a Fe-Mo/Al2O3catalyst in a horizontal tubularquartz furnace with4cm inner diameter (i.d.) and their average outer and inner diameter are20.8and6.6nm, respectively. The CNTs were prepared by the same CVD with xylene ascarbon source and their average outer and inner diameter are33.5and7.7nm, respectively.(b)NCNTs were synthesized by the same CVD with xylene as carbon source and aniline asnitrogen source and their outer and inner diameter are29-40and10-14nm, respectively. Thecontents of total nitrogen increase from0.3to3.11at.%with increasing aniline amount inprecursors. The contents of pyridinc nitrogen and quaternary nitrogen increase with increasinganiline amount in precursors, while the pyrrolic nitrogen content reaches its maximum at the aniline amount of50%in precursors and decreases with further increasing aniline amount.The graphitized structure of CNTs is unchanged obviously, while ID/IGratio of CNTsincreases with increasing aniline amount in precursors after the introduction of nitrogen atomsinto the carbon lattice. Moreover, the thermal stability of NCNTs are slightly lower than thatof the CNTs, but they no remarkable weight loss occurs before500oC.
(2) Selective oxidation of EB to AcPO in liquid-phase using oxygen as oxidant wasstudied on the carbon nanotube catalysts, and the effects of reaction conditions on the catalyticactivity of CNTs, the correlation between the performance and structures and probablereaction mechanism were investigated. The results are showed as follows:(a) At155oC,nCNTs/nEB=0.2and1.5MPa O2, EB conversion is38.2%with60.9%selectivity for AcPOafter4h of reaction.(b) In our catalytic system, the oxidation of EB proceeds by a free-radical mechanism, and the1-phenylethyl hydroperoxide (PEHP) is the most importantintermediate and the main chain propagator in the oxidation of EB, and the CNTs play animportant role in the decomposition of PEHP, owing to π-π interactions between the peroxideand the graphene sheets of the CNTs.(c) The contain residual Fe species of CNTs may notplay an active role in the oxidation of EB under our reaction conditions.(d) Surfacecarboxylic groups and defects of the CNTs are unfavorable to EB oxidation, it is probablycaused by the localization of electrons as a result of the introduction of carboxylic groups anddefects, which may be adverse to the π-π interaction between the PEHP or radical andgraphene sheets.(e) The CNTs catalyst shows outstanding recyclability, EB conversion is36.3%with60.6%selectivity for AcPO after six consecutive usages.(f) Doping nitrogenatoms into the carbon lattice are unfavorable to EB oxidation, it is probably attributed to theincreased defects in CNTs, resulting in a decrease of conductivity and electron mobility, thecharge transfer is suppressed, thus decrease π-π interaction between the radical or PEHP andthe graphene sheets of the CNTs.
(3) The catalytic performance and probable mechanism of CNTs and NCNTs in theselective liquid phase oxidation of benzyl alcohol were investigated. The results are showedas follows:(a) Neither CNTs nor NCNTs as a alone catalyst has lower catalytic activity forbenzyl alcohol oxidation with conversion of less than10%. HNO3is the most effectivepromoter achieving a benzyl alcohol conversion of96.2%and a benzaldehyde selectivity of88.3%after5h of reaction. However, HNO3alone cannot effectively improve the oxidationof benzyl alcohol in the absence of CNTs, and only obtained a benzyl alcohol conversion of31.4%and a benzaldehyde selectivity of75.3%after5h of reaction.(b) It is not free-radicaloxidation reaction. In our catalytic system, it is clarified that benzyl nitrite is an important intermediate, O2is the really terminal oxidant, while HNO3only initiates the oxidation cycle.(c) The contain residual Fe species of CNTs do not play an active role in the oxidation ofbenzyl alcohol under our reaction conditions, while electron transfer in graphene sheets playsan important role in the decomposition of benzyl nitrite.(d) The surface carboxylic groupsand defects of the CNTs have hardly influence on the benzyl alcohol conversion.(e) Propernitrogen doping indeed enhances the catalytic activity of CNTs in benzyl alcohol oxidation,probably arising from the enhanced electron transfer due to nitrogen dopant, thus enhances π-π interaction between the the intermediate and the graphene sheets of the CNTs. When thecontents of total nitrogen is1.02at.%, the NCNTs can obtain a benzaldehyde yield of78.5%after3h of reaction, while that is68.2%on CNTs catalyst under the same conditions.(f) TheCNTs and NCNTs catalysts have outstanding recyclability showing an excellent potential forindustrial application of benzyl alcohol oxidation to benzaldehyde.
（1）采用化学气相沉积法成功制备了碳纳米管和掺氮碳纳米管并对它们进行了系统表征。结果表明：采用液化气为碳源制备的碳纳米管平均外径和内径分别为20.8nm和6.6nm，而采用二甲苯为碳源制备的碳纳米管平均外径和内径分别为33.5nm和7.7nm。采用二甲苯为碳源、苯胺为氮源制备的掺氮碳纳米管外径和内径分别为29-40nm和10-14nm。掺氮碳纳米管的总掺氮含量随前驱物苯胺量的增加而增加，总掺氮含量在0.3at.%-3.11at.%之间，其中吡啶氮含量和季氮含量随前驱物苯胺量的增加而增加，而吡咯氮含量却随前驱物苯胺量的增加呈先增后减的趋势。向碳纳米管晶格中掺入氮原子并没有破坏其石墨化结构，但增加了其表面缺陷度，且缺陷度随总掺氮含量的增加而增大。掺氮碳纳米管与碳纳米管相比热稳定性稍有下降，但在500oC以下无明显失重，热稳定性好。
（2）研究了碳纳米管催化分子氧液相氧化乙苯生成苯乙酮的反应条件、结构与性能关系以及可能的反应机理。结果表明：(a)在155oC、催化剂与乙苯物质的量的比为0.2和1.5MPa O2条件下反应4h后，碳纳米管能获得38.2%乙苯转化率和60.9%苯乙酮选择性。(b)碳纳米管催化分子氧氧化乙苯反应是一个自由基反应，苯乙基过氧化氢的分解在反应中自由基链的传递和产物苯乙酮的生成起着非常重要的作用，而碳纳米管中石墨片的大π电子转移能力在苯乙基过氧化氢的分解反应过程中可能起着关键的作用。(c)碳纳米管残留的金属Fe杂质不是乙苯氧化反应的活性中心。(d)碳纳米管表面缺陷和羧基对其催化分子氧氧化乙苯反应有不利的影响，且碳纳米管的催化活性随其表面羧基量的增加而迅速降低。这是因为向碳纳米管表面引入羧基后，由于氧原子电负性大于碳原子，表现出吸电子性质，造成局部的π电子不能很好的在石墨片层中离域，从而不利于含有羧基的碳纳米管的大π电子与苯乙基过氧化氢中间体发生π-π共轭作用，故催化活性降低。(e)碳纳米管作为催化剂在选择性催化分子氧氧化乙苯制备苯乙酮反应中表现出较高的稳定性，在连续重复5次后，能获得36.3%乙苯转化率和60.6%苯乙酮选择性，是一种很有应用前景的新型催化剂。(f)向碳纳米管掺杂非金属氮原子对其催化分子氧氧化乙苯反应有不利的影响，这是因为向碳纳米管晶格中掺入非金属的氮原子，增加了其表面缺陷，可能降低了掺氮碳纳米管的导电性和电子流动性，在一定程度上抑制了电子转移能力，不利于碳纳米管的石墨片层和自由基及过氧化物之间的π-π共轭作用，故催化活性降低。
（3）研究了碳纳米管和掺氮碳纳米管在催化分子氧氧化苯甲醇反应中的催化性能与作用机制。结果表明：(a)不论碳纳米管，还是掺氮碳纳米管单独作为催化剂，在常压90oC反应5h后都只能获得低于10%的苯甲醇转化率，活性较低；添加硝酸助剂后，相同条件下碳纳米管能获得96.2%的苯甲醇转化率和88.3%的苯甲醛选择性。但是，在没有碳纳米管的存在下，硝酸本身作为化学计量氧化剂不能高效的催化氧化苯甲醇，只能获得31.4%的苯甲醇转化率和75.3%的苯甲醛选择性。(b)碳纳米管催化分子氧氧化苯甲醇反应是一个非自由基反应，亚硝酸苄酯是硝酸助碳纳米管催化分子氧氧化苯甲醇反应的重要中间体，分子氧是消耗的氧化剂，而硝酸只是引发催化循环的一个引发剂。(c)碳纳米管残留的金属杂质不是苯甲醇氧化反应的活性中心，而碳纳米管中石墨片的大π电子转移能力在反应中起着非常重要的作用。(d)碳纳米管表面缺陷和含氧基团对苯甲醇转化率的影响较小。(e)向碳纳米管晶格中掺入适量的氮原子，能提高其催化活性，但一旦掺入过量的氮原子，反而降低其催化活性。当向碳纳米管晶格中掺入1.02at.%氮原子时，能获得最高的催化活性，即在常压90oC反应3h后能获得78.5%的苯甲醛产率；而未掺氮的碳纳米管在同样条件下只能获得68.2%的苯甲醛产率，这是因为向碳纳米管晶格中掺入适量的带有孤对电子的氮原子在一定程度上能增强碳纳米管中石墨片的大π电子转移能力，进而增强其与反应中间体亚硝酸苄酯的π-π共轭作用，有利于中间体亚硝酸苄酯的分解，从而增强其催化活性。(f)碳纳米管及掺氮碳纳米管作为催化剂在选择性催化分子氧液相氧化苯甲醇制备苯甲醛反应中均表现出较高的稳定性，是一类很有应用前景的新型催化剂。
Carbon nanotubes (CNTs) as catalyst supports and metal-free catalysts have attractedmuch attentions, owing to their unique physicochemical properties such as high specifcsurface areas, environmental acceptability, corrosion resistance, easy recovery of preciousmetals by support burning, thermal stability under nonoxidative condition and readily surfacemodifcation. At present, most of the studies on CNTs and nitrogen-doped carbon nanotubes(NCNTs) as metal-free catalysts have focused on the oxygen reduction reaction and gas phaseoxidative dehydrogenation reaction. However, it is rarely reported on selective liquid phaseoxidation reaction. In order to enlarge their application, the research on reaction mechanismof different liquid phase oxidation reactions is of great scientific and practical significance. Inthis thesis, the free radical or not free radical oxidation reactions catalyzed by CNTs andNCNTs were investigated, that is, selective liquid phase oxidation of benzyl alcohol orethylbenzene (EB) catalyzed by CNTs and NCNTs to prepare highly valuable chemicalproducts benzaldehyde or acetophenone (AcPO), respectively, under the mild reactionconditions. This study can reduce traditional catalysis dependency on precious and transitionmetals and reduce environment impact from great quantities of waste. Moreover, the effectsof surface oxygen functional groups and surface structure of carbon materials on the catalyticactivity of selective liquid phase oxidation of benzyl alcohol or EB were investigated andplausible catalytic mechanisms of the benzyl alcohol or EB aerobic oxidation were proposed.These results can provide important theoretical basis for promoting carbon materials’application in selective liquid phase oxidation reactions. The main contents are described asfollows:
(1) CNTs and NCNTs were successfully prepared by the chemical vapor deposition(CVD) method. The results are showed as follows:(a) The CNTs were prepared by CVD withliquefied petroleum gas as carbon source over a Fe-Mo/Al2O3catalyst in a horizontal tubularquartz furnace with4cm inner diameter (i.d.) and their average outer and inner diameter are20.8and6.6nm, respectively. The CNTs were prepared by the same CVD with xylene ascarbon source and their average outer and inner diameter are33.5and7.7nm, respectively.(b)NCNTs were synthesized by the same CVD with xylene as carbon source and aniline asnitrogen source and their outer and inner diameter are29-40and10-14nm, respectively. Thecontents of total nitrogen increase from0.3to3.11at.%with increasing aniline amount inprecursors. The contents of pyridinc nitrogen and quaternary nitrogen increase with increasinganiline amount in precursors, while the pyrrolic nitrogen content reaches its maximum at the aniline amount of50%in precursors and decreases with further increasing aniline amount.The graphitized structure of CNTs is unchanged obviously, while ID/IGratio of CNTsincreases with increasing aniline amount in precursors after the introduction of nitrogen atomsinto the carbon lattice. Moreover, the thermal stability of NCNTs are slightly lower than thatof the CNTs, but they no remarkable weight loss occurs before500oC.
(2) Selective oxidation of EB to AcPO in liquid-phase using oxygen as oxidant wasstudied on the carbon nanotube catalysts, and the effects of reaction conditions on the catalyticactivity of CNTs, the correlation between the performance and structures and probablereaction mechanism were investigated. The results are showed as follows:(a) At155oC,nCNTs/nEB=0.2and1.5MPa O2, EB conversion is38.2%with60.9%selectivity for AcPOafter4h of reaction.(b) In our catalytic system, the oxidation of EB proceeds by a free-radical mechanism, and the1-phenylethyl hydroperoxide (PEHP) is the most importantintermediate and the main chain propagator in the oxidation of EB, and the CNTs play animportant role in the decomposition of PEHP, owing to π-π interactions between the peroxideand the graphene sheets of the CNTs.(c) The contain residual Fe species of CNTs may notplay an active role in the oxidation of EB under our reaction conditions.(d) Surfacecarboxylic groups and defects of the CNTs are unfavorable to EB oxidation, it is probablycaused by the localization of electrons as a result of the introduction of carboxylic groups anddefects, which may be adverse to the π-π interaction between the PEHP or radical andgraphene sheets.(e) The CNTs catalyst shows outstanding recyclability, EB conversion is36.3%with60.6%selectivity for AcPO after six consecutive usages.(f) Doping nitrogenatoms into the carbon lattice are unfavorable to EB oxidation, it is probably attributed to theincreased defects in CNTs, resulting in a decrease of conductivity and electron mobility, thecharge transfer is suppressed, thus decrease π-π interaction between the radical or PEHP andthe graphene sheets of the CNTs.
(3) The catalytic performance and probable mechanism of CNTs and NCNTs in theselective liquid phase oxidation of benzyl alcohol were investigated. The results are showedas follows:(a) Neither CNTs nor NCNTs as a alone catalyst has lower catalytic activity forbenzyl alcohol oxidation with conversion of less than10%. HNO3is the most effectivepromoter achieving a benzyl alcohol conversion of96.2%and a benzaldehyde selectivity of88.3%after5h of reaction. However, HNO3alone cannot effectively improve the oxidationof benzyl alcohol in the absence of CNTs, and only obtained a benzyl alcohol conversion of31.4%and a benzaldehyde selectivity of75.3%after5h of reaction.(b) It is not free-radicaloxidation reaction. In our catalytic system, it is clarified that benzyl nitrite is an important intermediate, O2is the really terminal oxidant, while HNO3only initiates the oxidation cycle.(c) The contain residual Fe species of CNTs do not play an active role in the oxidation ofbenzyl alcohol under our reaction conditions, while electron transfer in graphene sheets playsan important role in the decomposition of benzyl nitrite.(d) The surface carboxylic groupsand defects of the CNTs have hardly influence on the benzyl alcohol conversion.(e) Propernitrogen doping indeed enhances the catalytic activity of CNTs in benzyl alcohol oxidation,probably arising from the enhanced electron transfer due to nitrogen dopant, thus enhances π-π interaction between the the intermediate and the graphene sheets of the CNTs. When thecontents of total nitrogen is1.02at.%, the NCNTs can obtain a benzaldehyde yield of78.5%after3h of reaction, while that is68.2%on CNTs catalyst under the same conditions.(f) TheCNTs and NCNTs catalysts have outstanding recyclability showing an excellent potential forindustrial application of benzyl alcohol oxidation to benzaldehyde.
引文
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