CN109305915A - 对氯苯胺的合成方法 - Google Patents

对氯苯胺的合成方法 Download PDF

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Publication number
CN109305915A
CN109305915A CN201810842345.XA CN201810842345A CN109305915A CN 109305915 A CN109305915 A CN 109305915A CN 201810842345 A CN201810842345 A CN 201810842345A CN 109305915 A CN109305915 A CN 109305915A
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catalyst
carbon
synthetic method
content
nickel
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CN109305915B (zh
Inventor
吴耿煌
荣峻峰
达志坚
宗明生
于鹏
谢婧新
林伟国
纪洪波
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Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
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Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
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Abstract

提供一种对氯苯胺的合成方法，包括：以碳包覆镍纳米复合材料为催化剂，以氢气为氢源，催化对氯硝基苯制备对氯苯胺；其中，所述碳包覆镍纳米复合材料包括碳包覆镍纳米颗粒，其中所述碳包覆镍纳米颗粒由镍纳米颗粒内核和包裹在所述镍纳米颗粒表面的石墨化碳层外壳组成，并且所述石墨烯碳层外壳具有至少一个介孔分布峰。本发明利用碳包覆镍纳米复合材料作为催化剂催化对氯硝基苯加氢制备对氯苯胺的过程中无需使用脱氯抑制剂，反应选择性高，反应条件温和，产物与催化剂分离较为简便。

Description

对氯苯胺的合成方法
技术领域
本发明属于有机化学合成技术领域，具体涉及一种以碳包覆镍纳米复合材料为催化剂，催化对氯硝基苯加氢制备对氯苯胺的方法。
背景技术
对氯苯胺是重要的有机中间体，被广泛应用于染料、医药、农药、香料及合成橡胶等行业。由对氯硝基苯制备对氯苯胺的方法包括金属粉还原法、电化学还原法、水合肼还原法、硼氢化物还原法、催化加氢还原法等。其中催化加氢法因具有工艺先进、操作简便、产品收率高、产品质量好以及环境友好等优点而受到广泛关注。
催化加氢法的催化剂主要有负载型贵金属(Pt，Rh，Ir，Ru，Au)、雷尼镍及非晶态合金等。这些催化剂尽管有着较高的催化活性，但在反应过程中容易导致对氯苯胺发生脱氯副反应，不但降低了产品质量，且生成的氯化氢严重腐蚀设备。添加脱氯抑制剂，虽在一定程度上抑制了脱氯，但增加了抑制剂与产物的分离问题。如何高选择性的催化对氯硝基苯加氢制备对氯苯胺同时抑制脱氢反应是该领域的研究难点。
近年来，作为新兴的复合材料，碳包覆金属纳米材料由于具有优异的性能及应用前景，对其的制备及应用研究成为了一个研究热点。相关研究表明利用单层或多层石墨包裹金属纳米颗粒可以有效的将两种材料的优点结合在一起并呈现出新的特性。Westerhaus等[Nature Chemistry,2013,5(6):537-543] 以菲啰啉配位的Co为前驱体通过高温裂解制备了碳包覆金属钴及钴氧化物复合材料，在一系列芳香硝基化合物的催化加氢反应表现出了较高的活性与选择性。Fu等[Chinese Journal of Catalysis,2015,36(11):2030-2035]首先制备了氧化铝负载的氧化镍复合材料，通过乙二胺与四氯化碳在间二甲苯溶液中反应，并进一步高温碳化后制备了碳氮化合物包裹的氧化铝负载Ni复合材料。该材料具有高选择性的对氯硝基苯加氢性能。Tang等[RSC Advances, 2017,7(3):1531-1539]以对苯二甲酸为配位，硝酸镍为镍源，N,N-二甲基甲酰胺为溶剂，在高压反应釜中反应制备Ni MOF前驱体，并进一步通过高温碳化制备碳包覆镍复合材料，该材料在对氯硝基苯等芳香硝基化物的加氢反应中同样表现出了较好的选择性。
虽然以上材料在对氯硝基苯加氢制备对氯苯胺的反应中表现出了优异的活性和选择性，但是所使用的催化剂的制备仍存在着配体价格高、制备效率低、步骤繁琐、需要使用大量有机溶剂等缺点。如何简易、高效、绿色环保的制备一种具有良好催化加氢性能的碳包覆镍核壳结构纳米材料，对于促进碳包覆非贵金属纳米材料在对氯苯胺的工业化制备应用具有重要意义。
发明内容
本发明的目的是提供一种以碳包覆镍为催化剂，催化对氯硝基苯加氢制备对氯苯胺的方法。
本发明提供一种对氯苯胺的合成方法，包括：以碳包覆镍纳米复合材料为催化剂，以氢气为氢源，催化对氯硝基苯制备对氯苯胺；其中，所述碳包覆镍纳米复合材料包括碳包覆镍纳米颗粒，其中所述碳包覆镍纳米颗粒由镍纳米颗粒内核和包裹在所述镍纳米颗粒表面的石墨化碳层外壳组成，并且所述所述镍纳米颗粒内核包括面心立方晶格结构和/或六方紧密晶格结构。
根据本发明的一实施方式，其中包括以下步骤：将所述催化剂、溶剂、对氯硝基苯加入高压反应釜内；以氢气置换反应釜内的空气后，保持氢气压力在0.5Mpa～2Mpa；反应温度为60～120℃；反应0.5～3小时。
根据本发明的另一实施方式，其中所述催化剂与所述对氯硝基苯的质量比为1:0.1～500，优选1:3～100。
根据本发明的另一实施方式，其中所述对氯硝基苯与所述溶剂的质量比为1：2～500，优选1:3～100。
根据本发明的另一实施方式，其中所述溶剂为水、甲醇、乙醇、正丙醇和四氢呋喃中的一种或多种。
根据本发明的另一实施方式，其中以所述催化剂的总质量为基准，所述催化剂中Ni的含量为5-80％，C的含量为20-93％，O的含量为0.5-6％，N 的含量为0.5-6％，H的含量为0.1-2.5％。
根据本发明的另一实施方式，其中所述催化剂具有至少一个介孔分布峰。
根据本发明的另一实施方式，所述催化剂具有介孔孔径在2-5nm以及 8-12nm两个分布峰。
根据本发明的另一实施方式，所述催化剂中介孔体积占总孔体积的比例大于90％，优选大于95％。
根据本发明的另一实施方式，所述催化剂中镍纳米颗粒的粒径为2-35 nm。
本发明利用碳包覆镍纳米复合材料作为催化剂催化对氯硝基苯加氢制备对氯苯胺的过程中无需使用脱氯抑制剂，反应选择性高，反应条件温和，产物与催化剂分离较为简便。
附图说明
附图是用来提供对本发明的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一起应用于解释本发明，但并不构成对本发明的限制。在附图中：
图1是实施例1所制备的催化剂的XRD图。
图2A是实施例2所制备的催化剂的XPS全谱。
图2B是实施例2所制备的催化剂的XPS Ni 2p图。
图3A是实施例2所制备的催化剂的N2吸脱附等温曲线图。
图3B是实施例2所制备的催化剂的孔径分布图。
图4是实施例3所制备的催化剂的XRD图。
图5A是实施例3所制备的催化剂的N2吸脱附等温曲线图。
图5B是实施例3所制备的催化剂的孔径分布图。
图6是实施例4所制备的催化剂的XRD图。
图7A是实施例4所制备的催化剂的N2吸脱附等温曲线图。
图7B是实施例4所制备的催化剂的孔径分布图。
图8是实施例4所制备的催化剂的TEM图。
图9是实施例5所制备的催化剂的TEM图。
具体实施方式
以下结合附图通过具体的实施例对本发明作出进一步的详细描述，应当理解的是，此处所描述的具体实施方式仅用于说明和解释本发明，但不以任何方式限制本发明。
本发明中术语“核壳结构”是指内核为镍纳米颗粒，壳层为氮、氧掺杂的石墨化碳层。术语“石墨化碳层”是指在高分辨透射电镜下可明显观察到层状结构的碳结构，而非无定型结构，且层间距约为0.34nm。该石墨化碳层包覆过渡金属纳米颗粒后形成的复合材料呈球形或类球形。
术语“介孔”定义为孔径在2～50nm范围的孔。孔径小于2nm的孔定义为微孔，大于50nm的孔定义为大孔。
术语“介孔分布峰”是指根据Barrett-Joyner-Halenda(BJH)方法对脱附曲线进行计算得到的孔分布曲线上的介孔分布峰。
术语“酸洗损失率”是指制备完成的碳包覆过渡金属的纳米复合材料产品经酸洗后过渡金属的损失比例。其反映了石墨化碳层对过渡金属包覆的严密程度。如果石墨化碳层对过渡金属包覆不严密，则在酸处理后，内核的过渡金属会被酸溶解从而流失。酸洗损失率越大，表明石墨化碳层对过渡金属包覆的严密程度越低，酸洗损失率越小，表明石墨化碳层对过渡金属包覆的严密程度越高。
所述的“酸洗损失率”按以下方式测量并计算：
按20mL硫酸水溶液(1mol/L)投加1g样品的比例，在90℃下对样品处理 8h，然后用去离子水洗涤至中性，干燥后称重、分析，按下式计算酸洗损失率。
酸洗损失率＝[1-(酸洗后复合材料中过渡金属的质量分数×酸洗后复合材料的质量)÷(待酸洗复合材料中过渡金属的质量分数×待酸洗复合材料的质量)]×100％。
通过XRD获得材料的成分、材料内部原子或分子的结构或形态等信息。所采用XRD衍射仪的型号为XRD-6000型X射线粉末衍射仪(日本岛津)， XRD测试条件为：Cu靶，Kα射线(波长λ＝0.154nm)，管电压为40kV，管电流为200mA，扫描速度为10°(2θ)/min。
通过扫描电镜(SEM)表征材料的表面形貌。所采用的扫描电镜的型号为HitachiS-4800冷场扫描发射电镜，扫描电镜的测试条件为：将粉末样品通过导电胶固定在样品台观察，加速电压为5kV。通过高分辨透射电镜 (HRTEM)表征材料的表面形貌。所采用高分辨透射电镜的型号为JEM-2100 (日本电子株式会社)，高分辨透射电镜测试条件为：加速电压为200kV。样品中纳米颗粒的粒径通过电镜图片测量得到。
通过X射线光电子能谱分析仪(XPS)检测材料表面的元素。所采用X射线光电子能谱分析仪为VG Scientifc公司生产配备有Avantage V5.926软件的 ESCALab220i-XL型射线电子能谱仪，X射线光电子能谱分析测试条件为：激发源为单色化A1KαX射线，功率为330W，分析测试时基础真空为 3×10-9mbar。
通过BET测试方法检测材料的孔结构性质。具体采用Quantachrome AS-6B型分析仪测定，催化剂的比表面积由Brunauer-Emmett-Taller(BET)方法得到，孔分布曲线根据Barrett-Joyner-Halenda(BJH)方法对脱附曲线进行计算得到。
碳(C)、氢(H)、氧(O)、氮(N)四种元素的分析在Elementar Micro Cube元素分析仪上进行。具体操作方法和条件如下：样品在锡杯中称量1-2mg，放入自动进样盘，通过球阀进入燃烧管燃烧，燃烧温度为1000℃(为了去除进样时大气干扰，采用氦气吹扫)，然后用还原铜对燃烧后的气体进行还原，形成氮气、二氧化碳和水。混合气体通过三根解吸柱进行分离，依次进TCD检测器检测。氧元素的分析是利用高温分解，在碳催化剂的作用下，将样品中的氧转化为CO，然后采用TCD检测CO。
金属元素含量为材料扣除碳、氢、氧、氮含量后归一化结果。
本发明的对氯苯胺的合成方法，包括：以碳包覆镍纳米复合材料为催化剂，以氢气为氢源，催化对氯硝基苯选择性加氢制备对氯苯胺；其中，碳包覆镍纳米复合材料包括碳包覆镍纳米颗粒，碳包覆镍纳米颗粒由镍纳米颗粒内核和包裹在镍纳米颗粒表面的石墨化碳层外壳组成，并且石墨烯碳层外壳具有至少一个介孔分布峰。
具体包括以下步骤：将催化剂、溶剂、对氯硝基苯加入高压反应釜内；以氢气置换反应釜内的空气后，保持氢气压力在0.5Mpa～2Mpa；反应温度为60～120℃；反应0.5～3小时。可以分几次通入氢气，例如分3次通入氢气。
反应过程催化剂与对氯硝基苯的质量比为1:0.1～500，优选1:3～100。
对氯硝基苯与溶剂的质量比为1：2～1001：2～500，优选1:3～100。
溶剂为水、甲醇、乙醇、正丙醇和四氢呋喃中的一种或多种。
碳包覆镍纳米复合材的催化剂，以催化剂的总质量为基准，催化剂中Ni 的含量为5-80％，C的含量为20-93％，O的含量为0.5-6％，N的含量为0.5-6％， H的含量为0.1-2.5％。催化剂的内核包括面心立方晶格结构和/或六方紧密晶格结构。催化剂具有介孔孔径在2-5nm以及8-12nm两个分布峰。
实施例1
称取8.77g(30mmol)乙二胺四乙酸和1.39g(15mmol)氢氧化镍加入300 mL去离子水中，在90℃下搅拌得到均相溶液，并继续加热蒸干，将固体研磨后得到前驱体。
将得到的前驱体至于瓷舟内，然后将瓷舟置于管式炉的恒温区，通入氮气，流量100mL/min，并以5℃/min的速率升温至450℃，恒温30min后停止加热，在氮气气氛下冷却至室温，得到碳包覆纳米材料作为催化剂。
对制得的催化剂进行表征，图1是制得的催化剂的的X射线衍射谱图。从图1可以看出衍射角27°附近存在碳材料的衍射峰，其余衍射峰对应了 hcp-Ni和fcc-Ni两种晶相的Ni纳米材料。元素分析仪测定纳米材料C含量为36.32％，H含量为0.75％，N含量为1.79％，O含量为1.96％，归一化后 Ni含量为59.18％。按术语部分所述方法测量、计算，本实施例制得的复合材料的酸洗损失率为45％。在术语部分所述方法的基础上，继续增加酸洗时间，酸洗损失率基本保持不变。此外，BET测试表明，该纳米复合材料的比表面积为265m2/g，孔体积为0.353cm3/g，其中介孔体积占总孔体积的98.7％。
对氯苯胺的制备：将对氯硝基苯10g，无水乙醇150mL，制得的催化剂 3g，加入高压反应釜内，通氢气置换3次后保留氢气分压2MPa。加热反应釜并维持110℃搅拌反应2h，对氯苯胺收率为96.4％。
实施例2
称取4.38g(10mmol)乙二胺四乙酸、1.33g亚氨基二乙酸(10mol)和 3.76g(10mmol)四水合碱式碳酸镍加入100mL去离子水中，在80℃下搅拌得到均相溶液，并继续加热蒸干，将固体研磨后得到前驱体。
将得到的前驱体至于瓷舟内，然后将瓷舟置于管式炉的恒温区，通入氮气，流量150mL/min，并以5℃/min的速率升温至520℃，恒温2h后停止加热，在氮气气氛下冷却至室温，得到碳包覆纳米材料。
将得到的碳包覆纳米材料加入50mL 1mol/L HCl溶液中，在85℃下搅拌并回流4h后将溶液进行抽滤，并用去离子水洗至中性后将粉末置于100℃烘箱干燥2h，得到纯化的碳包覆纳米材料作为催化剂。
对制得的催化剂进行表征，图2是制得的催化剂的X射线光电子能谱 (XPS)。从图2A可以看到明显存在这C、N、O、Ni的XPS峰，证明了N、 O元素的有效掺杂。从图2B可以看出，其中Ni的价态为0价，充分证明了这种核壳结构有效的将高活性的Ni纳米粒子与空气隔绝，核壳结构完整。图 3A是制得的催化剂的N2吸附脱附等温曲线图。图3B是制得的催化剂的孔径分布图。从图3A可以看出这种材料在p/p0＝0.4～1.0之间出现明显的滞后环。从图3B可以看出，这种材料的孔径分布在直径为3.8nm与10.3nm的地方出现了两个分布峰。该纳米复合材料的比表面积为241m2/g，孔体积为0.489 cm3/g，其中介孔体积占总孔体积的99.4％。元素分析仪测定纳米材料C含量为37.96％，H含量为0.68％，N含量为1.50％，O含量为3.61％，归一化后 Ni含量为56.25％。按术语部分所述方法测量、计算，本实施例制得的纯化前的复合材料的酸洗损失率为15％，纯化后的材料的酸洗损失率小于2％。在术语部分所述方法的基础上，继续增加酸洗时间，酸洗损失率基本保持不变。对氯苯胺的制备：将对氯硝基苯10g，无水乙醇300mL，制得的催化剂 4g，加入高压反应釜内，通氢气置换3次后保留氢气分压1.5MPa。加热反应釜并维持120℃搅拌反应2h，对氯苯胺收率为99.2％。
实施例3
称取4.38g(15mmol)乙二胺四乙酸和1.85g(20mmol)氢氧化镍加入150 mL去离子水中，在75℃下搅拌得到均相溶液，并继续加热蒸干，将固体研磨后得到前驱体。
将得到的前驱体至于瓷舟内，然后将瓷舟置于管式炉的恒温区，通入氮气，流量80mL/min，并以3℃/min的速率升温至600℃，恒温3h后停止加热，在氮气气氛下冷却至室温，得到碳包覆纳米材料。
将得到碳包覆纳米材料加入60mL 0.5mol/L H2SO4溶液中，在80℃下搅拌并回流6h后将溶液进行抽滤，并用去离子水洗至中性后将粉末置于100℃烘箱干燥2h，得到纯化的碳包覆纳米材料作为催化剂。
对制得的催化剂进行表征，图4是制得的催化剂的X射线衍射谱图。与图1类似，图4同样只存在碳材料的衍射峰以及hcp-Ni和fcc-Ni的衍射峰。图5A是制得的催化剂的N2吸脱附等温曲线图。图5B是制得的催化剂的孔径分布图。图5表明催化剂的孔径分布在在直径为3.7nm与10.0nm的地方出现了两个分布峰。该纳米复合材料的比表面积为224m2/g，孔体积为0.457 cm3/g，其中介孔体积占总孔体积的99.7％。元素分析仪测定纳米材料C含量为37.42％，H含量为0.54％，N含量为1.45％，O含量为1.86％，归一化后 Ni含量为58.73％。按术语部分所述方法测量、计算，本实施例制得的纯化前的复合材料的酸洗损失率为12％。在术语部分所述方法的基础上，继续增加酸洗时间，酸洗损失率基本保持不变。
对氯苯胺的制备：将对氯硝基苯10g，无水乙醇400mL，制得的催化剂 4g，加入高压反应釜内，通氢气置换3次后保留氢气分压1MPa。加热反应釜并维持120℃搅拌反应2h，对氯苯胺收率为98.1％。
实施例4
称取2.92g(10mmol)乙二胺四乙酸、1.53g(5mmol)1,3-丙二胺四乙酸和 1.85g(20mmol)氢氧化镍加入120mL去离子水中，在80℃下搅拌得到均相溶液，并继续加热蒸干，将固体研磨后得到前驱体。
将得到的前驱体至于瓷舟内，然后将瓷舟置于管式炉的恒温区，通入氮气，流量80mL/min，并以2.5℃/min的速率升温至725℃，恒温3.5h后停止加热，在氮气气氛下冷却至室温，得到碳包覆纳米材料。
将得到碳包覆纳米材料加入50mL 0.5mol/L H2SO4溶液中，在90℃下搅拌并回流6h后将溶液进行抽滤，并用去离子水洗至中性后将粉末置于100℃烘箱干燥2h，得到纯化的碳包覆纳米材料作为催化剂。
对制得的催化剂进行表征，图6是制得的催化剂的X射线衍射谱图。图 6同样只存在碳材料的衍射峰以及hcp-Ni和fcc-Ni的衍射峰，与图1及图4 的不同之处在于hcp-Ni的峰强度下降，尤其是在42°和62°的衍射峰近乎消失。图7A是制得的催化剂的N2吸脱附等温曲线图。图7B是制得的催化剂的孔径分布图。表明制得的催化剂的孔径分布在在直径为3.8nm与10.1nm 的地方出现了两个分布峰。该纳米复合材料的比表面积为303m2/g，孔体积为0.581cm3/g，其中介孔体积占总孔体积的99.3％。图8是制得的催化剂的 TEM图。从图8可以看到明显的石墨壳层与金属内核直接证明了纳米颗粒的核壳结构。元素分析仪测定纳米材料C含量为46.91％，H含量为0.42％，N含量为1.54％，O含量为1.83％，归一化后Ni含量为49.30％。按术语部分所述方法测量、计算，本实施例制得的纯化前的复合材料的酸洗损失率为40％。在术语部分所述方法的基础上，继续增加酸洗时间，酸洗损失率基本保持不变。
对氯苯胺的制备：将对氯硝基苯10g，无水乙醇200mL，制得的催化剂 3g，加入高压反应釜内，通氢气置换3次后保留氢气分压2MPa。加热反应釜并维持120℃搅拌反应2h，对氯苯胺收率为98.5％。
实施例5
称取2.92g(10mmol)乙二胺四乙酸和1.49g(20mmol)氧化镍加入100 mL去离子水中，在85℃下搅拌得到均相溶液，并继续加热蒸干，将固体研磨后得到前驱体。
将得到的前驱体至于瓷舟内，然后将瓷舟置于管式炉的恒温区，通入氮气，流量80mL/min，并以2.5℃/min的速率升温至625℃，恒温2h后停止加热，在氮气气氛下冷却至室温，得到碳包覆纳米材料。
将得到碳包覆纳米材料加入60mL 1mol/L HCl溶液中，在90℃下搅拌并回流6h后将溶液进行抽滤，并用去离子水洗至中性后将粉末置于100℃烘箱干燥2h，得到纯化的碳包覆纳米材料作为催化剂。
对制得的催化剂进行表征，图9是制得的催化剂的HRTEM图片。从图 9(b)可以看出对应hcp-Ni(101)的晶格条纹。此外，BET测试表明，该酸洗纯化后纳米复合材料的比表面积为256m2/g，孔体积为0.513cm3/g，其中介孔体积占总孔体积的98.6％。元素分析仪测定纳米材料C含量为36.70％，H 含量为0.52％，N含量为1.30％，O含量为1.82％，归一化后Ni含量为 59.44％。按术语部分所述方法测量、计算，本实施例制得的纯化前的复合材料的酸洗损失率为18％。在术语部分所述方法的基础上，继续增加酸洗时间，酸洗损失率基本保持不变。
对氯苯胺的制备：将对氯硝基苯10g，无水乙醇200mL，制得的催化剂 3g，加入高压反应釜内，通氢气置换3次后保留氢气分压2MPa。加热反应釜并维持120℃搅拌反应2h，对氯苯胺收率为99.4％。
本发明利用碳包覆镍纳米复合材料作为催化剂催化对氯硝基苯加氢制备对氯苯胺的过程中无需使用脱氯抑制剂，反应选择性高，反应条件温和，产物与催化剂分离较为简便。
当然，本发明还可有其它多种实施例，在不背离本发明精神及其实质的情况下，熟悉本领域的技术人员当可根据本发明作出各种相应的改变和变形，但这些相应的改变和变形都应属于本发明所附的权利要求的保护范围。

Claims (10)

1.一种对氯苯胺的合成方法，包括：
以碳包覆镍纳米复合材料为催化剂，以氢气为氢源，催化对氯硝基苯制备对氯苯胺；
其中，所述碳包覆镍纳米复合材料包括碳包覆镍纳米颗粒，其中所述碳包覆镍纳米颗粒由镍纳米颗粒内核和包裹在所述镍纳米颗粒表面的石墨化碳层外壳组成，并且所述镍纳米颗粒内核包括面心立方晶格结构和/或六方紧密晶格结构。
2.根据权利要求1所述的合成方法，其中包括以下步骤：将所述催化剂、溶剂、对氯硝基苯加入高压反应釜内；以氢气置换反应釜内的空气后，保持氢气压力在0.5Mpa～2Mpa；反应温度为60～120℃；反应0.5～3小时。
3.根据权利要求2所述的合成方法，其中所述催化剂与所述对氯硝基苯的质量比为1:0.1～500，优选1:3～100。
4.根据权利要求2所述的合成方法，其中所述对氯硝基苯与所述溶剂的质量比为1：2～500，优选1:3～100。
5.根据权利要求2所述的合成方法，其中所述溶剂为水、甲醇、乙醇、正丙醇和四氢呋喃中的一种或多种。
6.根据权利要求1所述的合成方法，其中以所述催化剂的总质量为基准，所述催化剂中Ni的含量为5-80％，C的含量为20-93％，O的含量为0.5-6％，N的含量为0.5-6％，H的含量为0.1-2.5％。
7.根据权利要求1所述的合成方法，其中所述催化剂具有至少一个介孔分布峰。
8.根据权利要求1所述的合成方法，所述催化剂具有介孔孔径在2-5nm以及8-12nm两个分布峰。
9.根据权利要求1所述的合成方法，所述催化剂中介孔体积占总孔体积的比例大于90％，优选大于95％。
10.根据权利要求1所述的合成方法，其中所述复合材料的酸洗损失率小于50％，优选小于20％，更优选小于10％，最优选小于2％。
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