纳米金催化剂的合成及其在二醇氧化制内酯反应中的应用研究
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摘要
内酯杂环化合物由于其具有高沸点、高溶解性、高电导率和稳定性能好的特点,可用作溶剂、萃取剂、吸收剂以及一些聚合物的单体,广泛地应用于石油化工、纺织、香料、农药和医药等领域。本论文采用纳米Au作为催化剂,空气为氧化剂,在较温和的条件下通过二元醇的一步氧化来制备内酯,为内酯类化合物的合成提供了一条绿色、清洁并且高效的途径。
当Au以纳米尺寸分散时,在很多反应如低温CO氧化、醇氧化、水气转换、选择性加氢等反应中表现出高的催化活性,并且由于其具有低温活性和高选择性的特点,近年来越来越受到人们的重视。本论文通过对催化剂上Au的颗粒大小、Au的电子状态和载体效应的研究来揭示Au催化剂的活性位和催化机理。
本文中制得的纳米Au催化剂在催化一系列二醇如1,4-丁二醇、1,5-戊二醇、邻苯二甲醇等的氧化制备γ-丁内酯、6-戊内酯和苯酞中表现出很高的催化活性。通过对负载型Au催化剂的合成条件和催化剂组成的优化,催化剂载体的形貌和晶型的调变,以及复合载体的合成,得到了具有高催化活性、高选择性和稳定性的催化二元醇氧化制备内酯的Au催化剂,同时也对催化剂的活性中心、载体效应以及反应机理进行了探讨,得到的主要结果如下：
1.制备条件和催化剂组成对Au/TiO2催化剂的性质及其在催化空气氧化二醇制备内酯反应中的影响研究
以商业二氧化钛P25为载体,尿素为沉淀剂,采用均匀沉积沉淀法(HDP)合成了具有纳米尺寸的Au/TiO2催化剂,其中Au的平均粒径约5 nm。采用该方法合成的催化剂中Au与载体间有较强的相互作用,在催化空气氧化1,4-丁二醇和1,5-戊二醇生成γ-丁内酯和6-戊内酯反应中表现出较好的催化性能。研究发现,焙烧温度和Au负载量对催化活性均有较大影响,573-673 K焙烧,Au负载量为3-8%的催化剂表现出较好的催化活性。对催化剂进行表征后发现,高温焙烧的催化剂上Au颗粒较大,而低温焙烧的催化剂上Au未完全转变成金属态,仍有氧化态的Au物种(Au3+)存在。负载量大于8%的催化剂,表面Au物种趋向饱和,Au颗粒部分团聚,催化活性下降。据此推测分散在载体表面的0价的小粒径的Au为催化的活性物种。
2.不同氧化物负载的Au催化剂(Au/MOx)的性质及其在催化空气氧化二醇制备内酯反应中的催化性能研究
合成了包括过渡金属和主族金属氧化物为载体的纳米Au催化剂,大部分催化剂在催化空气氧化1,4-丁二醇制备γ-丁内酯反应中都表现出较好的催化活性。
过渡金属氧化物负载的Au催化剂中,Au/TiO2、Au/MnOx、Au/Fe2O3、Au/Co3O4、Au/ZnO、Au/CeO2以及Au/ZrO2在l,4-丁二醇氧化反应中表现出较高的活性和选择性,反应8小时后转化率和选择性都可达90%。其中,TiO2和MnOx负载的Au催化剂在反应4小时即可达80%的转化率,是1,4-丁二醇氧化制备Y-丁内酯的优良催化剂。Au/NiO活性相对较差,在该载体上的Au颗粒较大(-16nm),且由XPS表征可发现该催化剂表面Au含量较低,因此活性较低。
主族金属氧化物中Au/SnO2的活性甚至超过了一些过渡金属氧化物负载的Au催化剂,反应4小时后1,4-丁二醇已转化82%,反应8小时后转化率可达99%。由于Mg(OH)2呈碱性,会促进γ-丁内酯水解,Au/Mg(OH)2催化的1,4-丁二醇氧化中γ-丁内酯选择性较差。而通常被认为是惰性载体的Al2O3则表现出较好的活性,反应4小时和8小时后的转化率分别为58%和99%。
对于上述活性载体负载的Au催化剂,Au颗粒的平均粒径在4-7 nm,载体粒径为10-30 nm,表面Au含量均高于体相Au含量,Au颗粒很好地分散在载体表面。经ICP测试,大部分Au都能够沉淀于载体上,Au颗粒与载体之间形成相互作用。BET测试给出的催化剂孔道信息表明,即使载体的比表面积很小,若Au能较好地分散,也能得到高的催化活性。
由以上结果可以推测,Au颗粒必须足够小才能得到较高催化活性,但催化活性不仅与Au颗粒大小有关,载体的种类对催化活性也有较大影响,载体的比表面积并非催化活性的决定性因素,Au-载体间的相互作用对催化活性影响较大。
3. Au/FeOx催化剂的载体效应及其在催化二醇氧化制备内酯反应中的催化性能研究
采用商业纳米氧化铁γ-Fe2O3、α-Fe2O3和Fe3O4作为Au催化剂的载体,发现Au在Fe3O4上分散最好,平均粒径为4.7 nm,其次是Au/α-Fe2O3 (5.5 nm)和Au/γ-Fe2O3(6.7nm)。该系列纳米氧化铁负载的Au催化剂在催化1,4-丁二醇氧化中的TOF值顺序为：Au/Fe3O4>Au/α-Fe2O3> Au/γ-Fe2O3。尽管Au/Fe3O4有较高的初始活性,但由于Fe3O4易被氧化,在高温高压氧化性条件下反应一段时间后被氧化成Au/γ-Fe2O3,导致最终的1,4-丁二醇转化率和内酯得率下降。在不同的气氛(空气、Ar、H2)下处理的Au/Fe3O4催化剂中,Au/Fe3O4-H2上Au的平均粒径最小(2.7 nm),然而却表现出与Au/Fe3O4-Ar接近的催化性能,由此可以推测,在不同铁的氧化物上负载的Au催化剂中,催化活性的差异主要不是由于粒径效应,而是载体效应所引起的。
采用水热法合成的FeOx-NF在不同温度下焙烧表现出不同的晶型和形貌。室温下干燥的样品主要以Fe3O4存在,经焙烧后氧化成γ-Fe2O3,当焙烧温度高于573 K时γ-Fe2O3向α-Fe2O3转变,氧化铁形貌也由颗粒和片状的混合形态向纳米片状转变。使用这些氧化铁作为Au催化剂的载体,得到的催化剂上Au均匀地分散在载体表面,平均粒径约为5 nm。Au/FeOx-NF在催化空气选择性氧化1,4-丁二醇和1,5-戊二醇反应中表现出很高的催化活性,转化率和选择性均高于商业氧化铁负载的Au催化剂。在1,4-丁二醇氧化反应中,γ-Fe2O3负载的Au催化剂得到了很高的TOF值(Au/FeOx-573的TOF值为624 h-1)。Au/FeOx-NF在1,5-戊二醇氧化中也得到了>90%的转化率。催化剂表征结果显示,载体对Au的粒径和电子性质有显著影响,Au和载体间存在强相互作用。在y-Fe2O3负载的Au催化剂上电子由载体向Au转移,而α-Fe2O3则对氧化态的Au具有稳定作用,导致表面的Au部分以氧化态(Auδ+)存在。载体效应导致Au物种在颗粒大小和氧化态上有所差异,从而表现出二醇氧化反应的活性差别。该Au/γ-Fe2O3催化剂性质不同于商业γ-Fe2O3负载的Au催化剂,商业γ-Fe2O3负载的Au催化剂相比商业α-Fe2O3和Fe3O4负载的Au催化剂表现出差的催化活性；在Au/FeOx-NF中可能是因为γ-Fe2O3的特殊形貌和合成方法导致Au-Fe2O3相互作用增强,催化活性提高。
4.AuAIT催化剂的性质及其在催化空气氧化二醇制备内酯反应中的催化性能研究
在对Au催化剂载体碱性的研究中,我们采用γ-AlOOH和γ-Al2O3作为载体(AlT),载体采用普通的沉淀法制备。从室温到973 K升温处理,载体由γ-AlOOH分解为γ-Al2O3。γ-AlOOH可在573 K以下稳定,当温度达到773 K时,完全转化为γ-Al2O3。由CO2-TPD可知,γ-Al2O3(A1773、A1873、A1973)上只存在大量的弱碱性位和少量中等碱性位,而在γ-AlOOH中,A1573主要为中等碱性位,在A1373中除了中等碱性位还有一定量的强碱性位。用AlT负载的Au催化剂中,γ-Al2O3(A1773、A1873、A1973)上可得到粒径较小的Au颗粒(平均粒径约4 nm),而γ-AlOOH(Al373、Al573)负载的催化剂上Au的平均粒径为5-8 nm。AuAlT催化剂在催化1,4-丁二醇氧化反应中表现出比其他载体负载的Au催化剂更高的催化活性,其中AuAl773在反应1小时即可达到90%的转化率。尽管Au颗粒较大,AuAl373仍表现出较高的催化活性,反应1小时转化率达74%,所有的催化剂在反应8小时后均可达到100%的二醇转化率。由于载体有一定的碱性,而产物内酯在碱性条件下不稳定,容易发生水解,该系列催化剂的选择性较Au/TiO2和Au/FeOx低,且随着时间延长,选择性先升高后降低。由此推论碱性位有利于醇氧化的发生,但会牺牲内酯的选择性。除了用于催化1,4-丁二醇氧化,该催化剂在催化1,5-戊二醇和邻苯二甲醇氧化得到6-戊内酯和苯酞的反应中也表现出很高的活性。
5.Fe-Al-Ox复合载体的合成及其负载的金催化剂在催化空气氧化1,4-丁二醇制备γ-丁内酯反应中的催化性能研究
分别采用包覆法、Al2O3上浸渍Fe2O3以及Fe2O3上浸渍Al2O3的方法得到了FeAOx、Fe2O3/Al2O3和Al2O3/Fe2O3的铁铝复合氧化物载体,经表征发现,Fe2O3/Al2O3和Al2O3/Fe2O3中Fe2O3与Al2O3只是简单的混合,Fe2O3与Al2O3未发生明显相互作用,而FeAlOx中Al2O3包裹在Fe2O3表面,TEM未观察到孤立的Fe2O3颗粒。XPS也表明FeAlOx表面富集Al,其表面Fe／Al比(1：18)最低,远低于体相(1：3.4),同时也比其他两种载体要低。FeAlOx负载的Au催化剂上Au颗粒均匀分散在载体表面,平均粒径为3.5 nm, Fe2O3的晶型为γ-Fe2O3, Au与载体间存在相互作用。FeAlOx负载的Au催化剂在1,4-丁二醇氧化反应中表现出很高的催化活性,比机械混合的Au/Fe2O3和Au／Al2O3要高,甚至接近活性最高的Au/Al2O3催化剂,而选择性要高于Au/Al2O3和Au/Fe2O3。该系列Fe-Al-O负载的Au催化剂的活性顺序为Au/FeAlOx> Au/Fe2O3/Al2O3-Au/Fe2O3+ Au/Al2O3> Au/Al2O3/Fe2O3。
对Au/FeAlOx催化剂的Fe/Al比进行考察后发现,当Fe/Al从1：1变为1：16时,表面Fe／Al比从1：8降低到1：41。当Fe/Al=1：1时,Al2O3的量不足以将所有的Fe203覆盖,由透射电镜图中可以观察到孤立的Fe2O3颗粒,而增加Al含量至Fe／Al=1：4,Al2O3将Fe2O3全部覆盖,继续增加Al含量,Al2O3过多,导致与Fe的作用减弱,不利于催化反应的进行,且由于其碱性较强,对内酯选择性会有不利影响。因此Fe／Al比为1：4的催化剂在1,4-丁二醇氧化反应中表现出最高的催化活性和内酯选择性。
The lactones and their derivatives are widely distributed in nature. The lactone ring exists in the molecules of many bioactive substances and metabolic intermediates. Due to their high boiling point, solubility, conductivity and stability, the lactones are widely used as solvent, extraction agent and also can be used for the synthesis of a variety of polymers. In this dissertation, the nano gold catalysts were used to catalyze the aerobic oxidative dehydrogenation of diols to lactones. The reaction was carried out at low temperature with air as oxidant, which is a clean route in accordance with the demand of green chemistry and sustainable development.
The nano gold is a catalyst with high performance in the low temperature CO oxidation, oxidation of alcohols, water-gas shift reaction and selective hydrogenation ofα,β-unsaturated aldehydes or ketones. Due to their low temperature activity and high selectivity, the gold catalysts are becoming more and more important. The gold particle size, gold electronic state and support effect was studied in this dissertation to investigate the active sites of gold catalyst and the reaction mechanism.
Gold catalysts prepared in this dissertation showed high activity in the oxidative dehydrogenation of a series of diols such as 1,4-butanediol,1,5-pentanediol and 1,2-benzenedimethanol to y-butyrolactone,δ-valerolactone and phthalanone. The preparation conditions of the catalysts, support compositions, support morphology and support crystal phase were optimized, and finally multi-component oxide support were prepared to give catalysts with high activity, selectivity and stability. At the same time, the active sites of the gold catalysts, as well as the support effect were discussed and the following results were obtained.
1. Influence of the preparation conditions and catalyst compositions on the catalytic performance of Au/TiO2 catalysts in the oxidative dehydrogenation of diols to lactones
The commercial Degussa P25 was utilized as support, and the gold catalysts were prepared by the homogeneous deposition-precipitation method (HDP) using urea as precipitation agent. Nano sized gold particles were obtained with average particle size of about 5 nm. There was interaction between gold and the support. The catalysts showed high activity in the oxidation of 1,4-butanediol and 1,5-pentanediol to the corresponding lactones. Calcination temperature had significant effect on the catalytic activity of the catalysts, and it was found that the catalyst with 3-8% gold loading calcined at 573-673 K gave high activity. From the characterization results it can be found that when calcined at high temperature, gold particles tended to aggregate and form large particles, but when the calcination temperature was below 573 K, gold species were not completely reduced, and there were still some oxidized gold (Au3+). For catalysts with gold loading higher than 8%, gold particles tended to aggregate and catalytic activity dropped. From the above results it can be concluded that the surface metallic gold species with small particle size were the active species.
2. Properties and catalytic performance of gold catalysts on different oxide support (Au/MOx)
The transition metal oxides and main group metal oxides were used as support for gold catalysts, and most of them showed high activity in the oxidative dehydrogenation of 1,4-butanediol to y-butyrolactone.
Among the transition metal oxide supported gold catalysts, Au/TiO2, Au/MnOx, Au/Fe2O3, Au/Co3O4, Au/ZnO, Au/CeO2 and Au/ZrO2 were highly active with both diol conversion and lactone selectivity above 90% after 8 hours'reaction, especially Au/TiO2 and Au/MnOx, whose conversion were above 80% after 4 hours'reaction. Due to its large gold particle size and low surface gold content, Au/NiO showed much lower activity.
Activity of Au/SnO2 was even superior to some of the transition metal oxide supported gold catalysts, with conversion of 82% after 4 hours'reaction and 99% after 8 hours'reaction. When catalyzed by Au/Mg(OH)2, the formed y-butyrolactone would be hydrolyzed due to the basicity of Mg(OH)2. Although A12O3 was always considered as inert in gold catalysis, Au/Al2O3 showed high activity with 4 hour and 8 hour conversion of 58% and 99%, respectively.
For the above gold catalysts on active support, the average gold particle size was in the range of 4-7 nm, and the support particle diameter was about 10-30 nm. The surface gold content was higher than that in bulk, and gold particles were highly dispersed on the surface of the support. Most of the gold can be deposited onto the support to form gold-support interaction. From the BET results it can be inferred that although surface area of some support oxides were low, gold catalysts with high activity can still be obtained on them.
From the above results, it can be concluded that gold particle size must be small enough to give high activity. However, the gold particle size was not the decisive factor and the type of the support was also important. Pore properties were not as important as support effect, and there was interaction between gold species and the support.
3. Support effect of Au/FeOx catalysts and their catalytic performance in the oxidative dehydrogenation of diols
The commercial nano iron oxidesγ-Fe2O3,α-Fe2O3 and Fe3O4 were utilized as support for gold catalysts, and it was found that the smallest gold particles were obtained on Fe3O4 with average gold diameter of 4.7 nm, and then the Au/α-Fe2O3 (5.5 nm), and the largest gold particles were got on Au/γ-Fe2O3 (6.7 nm). TOF values of the catalysts were in the order:Au/Fe3O4> Au/α-Fe2O3> Au/γ-Fe2O3. Although Au/Fe3O4 had the highest initial activity, Fe3O4 would be oxidized toγ-Fe2O3 during the reaction with high temperature and oxidative atmosphere, leading to the loss in activity and final lactone yield. For Au/Fe3O4 catalysts treated under different atmospheres, Au/Fe3O4-H2 had the smallest gold particle size (2.7 nm), but its catalytic behavior was similar to that of Au/Fe3O4-Ar. Therefore it was inferred that the different activity of the Au/FeOx with different crystal phase was due to the variation in support properties other than the gold particle size.
FeOx-NF was synthesized by a hydrothermal method, and showed different crystal phase and morphology when calcined at different temperatures. The room temperature treated sample was in the form of Fe3O4, and it was oxidized toγ-Fe2O3 when calcined at 573 K in air. Further increase in calcination temperature led to the crystal transformation fromγ-Fe2O3 toα-Fe2O3, and the simultaneous transformation of iron oxide particles to nano flakes. The FeOx-NF supported gold catalysts were more active than those supported on commercial iron oxides. When FeOx-NF in the. form ofγ-Fe2O3 was used as support for gold catalysts, it showed high TOF value (624 h-1 for Au/FeOx-573). According to the characterization results, the gold particles were evenly distributed on the support with average particle size about 5 nm, and the support had significant influence on the gold particle size distributions and electronic properties. There was strong gold-support interaction, and on Au/γ-Fe2O3, electrons were transferred from the support to gold, leading to the formation of negatively charged gold (Auδ-). On contrary,α-Fe2O3 can stabilize the oxidized gold species. Support was responsible for the variation in gold particle size and oxidation state, and thus the differences in catalytic activity. In contrast to commercial iron oxide supported gold catalysts, the Au/γ-Fe2O3 showed higher activity than Au/α-Fe2O3, and this may be due to the morphology change and support synthetic method utilized in this dissertation.
4. Catalytic properties of AuAlT catalysts in the oxidative dehydrogenation of diols to lactones
γ-AlOOH andγ-Al2O3 (AIT) were utilized as support for gold catalysts to investigate the influence of support basicity. The support was prepared by a simple deposition method, and by elevating pretreating temperature from room temperature to 973 K, AIT dehydroxylated fromγ-AlOOH toγ-Al2O3.γ-AlOOH was stable below 573 K, and then transformed toγ-Al2O3 at 773 K. According to the CO2-TPD results, there were mainly weak basic sites onγ-Al2O3 (A1773, A1873 and A1973), while forγ-AlOOH, there were medium basic sites on A1573 and strong basic sites on A1373. Small gold particle size can be obtained onγ-Al2O3 with average diameter about 4nm. Larger gold particles were got on y-AlOOH (A1373, A1573), and the average gold diameter was 5-8nm. Catalytic activity of AuAlT catalysts was higher than that of other oxide supported gold catalysts (Au/TiO2 and Au/FeOx). Conversion of AuA1773 reached 90% after 1 hour's reaction. Although with larger gold particle size, AuA1373 still showed high activity with 74% conversion after 1 hour's reaction. Conversion of all the catalysts can achieve 100% after 8 hours' reaction. Due to the basicity of the support, the y-butyrolactone product would be hydrolyzed, which led to the drop in lactone selectivity as compared to Au/TiO2 and Au/FeOx. Selectivity of AuAlT increased firstly and then dropped with the prolonging of reaction time. Therefore, it was concluded that basicity was beneficial to the oxidation of alcohols; however, it was detrimental to the lactone selectivity. AuAlT can also be used for the oxidation of other diols, for example,1,5-pentanediol and 1,2-benzedimethanol.
5. Synthesis of multi-component Fe-Al-O oxides and their application as support for gold catalysts in the oxidative dehydrogenation of 1,4-butanediol to y-butyrolactone
The multi-component Fe-Al-O oxides were prepared by encapsulation (FeAlOx) and impregnation methods (Fe2O3/Al2O3 and Al2O3/Fe2O3). According to the characterization results, it was found that when prepared by the impregnation method, there was no interaction between Fe2O3 and Al2O3, and the support was the simple mixture of Fe2O3 and Al2O3. For FeAlOx, Fe2O3 was encapsulated by Al2O3, and there were no isolated Fe2O3 particles observed, indicating that interaction was formed between Fe2O3 and Al2O3. It was also confirmed by the XPS results that FeAlOx surface was enriched with Al, due to its low surface Fe/Al ratio (1:18), which was far lower than that of the bulk (1:3.4) and the other two support prepared by the impregnation method. Crystal phase of FeAlOx wasγ-Fe2O3 andγ-Al2O3. Gold can be highly dispersed on the support surface with average diameter of 3.5 nm, and gold-support interaction was observed. Au/FeAlOx showed high activity in the oxidative dehydrogenation of 1,4-butanediol, and its catalytic activity was better than that of the mixture of Au/Fe2O3 and Au/Al2O3, very close to that of the most active Au/Al2O3 catalyst. In addition, its selectivity was higher than that of Au/Al2O3 and Au/Fe2O3. For Fe-Al-O supported gold catalysts, the activity was in the order: Au/FeAlOx> Au/Fe2O3/Al2O3-Au/Fe2O3+Au/Al2O3> Au/Al2O3/Fe2O3.
By adjusting the Fe/Al molar ratio of Au/FeAlOx catalysts from 1:1 to 1:16, the surface Fe/Al ratio changed from 1:8 to 1:41. When Fe/Al was 1:1, the amount of Al2O3 was not enough to encapsulate all the Fe2O3 particles and it can be seen from the TEM images that there were some isolated Fe2O3 particles. Increasing Al content to Fe/Al ratio of 1:4, Al2O3 can cover all the Fe2O3, however, further increase in Al content would lead to the weakening of the Fe-Al interaction and the stronger support basicity, which was not beneficial to the reaction. The optimized Fe/Al was found to be 1:4.
当Au以纳米尺寸分散时,在很多反应如低温CO氧化、醇氧化、水气转换、选择性加氢等反应中表现出高的催化活性,并且由于其具有低温活性和高选择性的特点,近年来越来越受到人们的重视。本论文通过对催化剂上Au的颗粒大小、Au的电子状态和载体效应的研究来揭示Au催化剂的活性位和催化机理。
本文中制得的纳米Au催化剂在催化一系列二醇如1,4-丁二醇、1,5-戊二醇、邻苯二甲醇等的氧化制备γ-丁内酯、6-戊内酯和苯酞中表现出很高的催化活性。通过对负载型Au催化剂的合成条件和催化剂组成的优化,催化剂载体的形貌和晶型的调变,以及复合载体的合成,得到了具有高催化活性、高选择性和稳定性的催化二元醇氧化制备内酯的Au催化剂,同时也对催化剂的活性中心、载体效应以及反应机理进行了探讨,得到的主要结果如下：
1.制备条件和催化剂组成对Au/TiO2催化剂的性质及其在催化空气氧化二醇制备内酯反应中的影响研究
以商业二氧化钛P25为载体,尿素为沉淀剂,采用均匀沉积沉淀法(HDP)合成了具有纳米尺寸的Au/TiO2催化剂,其中Au的平均粒径约5 nm。采用该方法合成的催化剂中Au与载体间有较强的相互作用,在催化空气氧化1,4-丁二醇和1,5-戊二醇生成γ-丁内酯和6-戊内酯反应中表现出较好的催化性能。研究发现,焙烧温度和Au负载量对催化活性均有较大影响,573-673 K焙烧,Au负载量为3-8%的催化剂表现出较好的催化活性。对催化剂进行表征后发现,高温焙烧的催化剂上Au颗粒较大,而低温焙烧的催化剂上Au未完全转变成金属态,仍有氧化态的Au物种(Au3+)存在。负载量大于8%的催化剂,表面Au物种趋向饱和,Au颗粒部分团聚,催化活性下降。据此推测分散在载体表面的0价的小粒径的Au为催化的活性物种。
2.不同氧化物负载的Au催化剂(Au/MOx)的性质及其在催化空气氧化二醇制备内酯反应中的催化性能研究
合成了包括过渡金属和主族金属氧化物为载体的纳米Au催化剂,大部分催化剂在催化空气氧化1,4-丁二醇制备γ-丁内酯反应中都表现出较好的催化活性。
过渡金属氧化物负载的Au催化剂中,Au/TiO2、Au/MnOx、Au/Fe2O3、Au/Co3O4、Au/ZnO、Au/CeO2以及Au/ZrO2在l,4-丁二醇氧化反应中表现出较高的活性和选择性,反应8小时后转化率和选择性都可达90%。其中,TiO2和MnOx负载的Au催化剂在反应4小时即可达80%的转化率,是1,4-丁二醇氧化制备Y-丁内酯的优良催化剂。Au/NiO活性相对较差,在该载体上的Au颗粒较大(-16nm),且由XPS表征可发现该催化剂表面Au含量较低,因此活性较低。
主族金属氧化物中Au/SnO2的活性甚至超过了一些过渡金属氧化物负载的Au催化剂,反应4小时后1,4-丁二醇已转化82%,反应8小时后转化率可达99%。由于Mg(OH)2呈碱性,会促进γ-丁内酯水解,Au/Mg(OH)2催化的1,4-丁二醇氧化中γ-丁内酯选择性较差。而通常被认为是惰性载体的Al2O3则表现出较好的活性,反应4小时和8小时后的转化率分别为58%和99%。
对于上述活性载体负载的Au催化剂,Au颗粒的平均粒径在4-7 nm,载体粒径为10-30 nm,表面Au含量均高于体相Au含量,Au颗粒很好地分散在载体表面。经ICP测试,大部分Au都能够沉淀于载体上,Au颗粒与载体之间形成相互作用。BET测试给出的催化剂孔道信息表明,即使载体的比表面积很小,若Au能较好地分散,也能得到高的催化活性。
由以上结果可以推测,Au颗粒必须足够小才能得到较高催化活性,但催化活性不仅与Au颗粒大小有关,载体的种类对催化活性也有较大影响,载体的比表面积并非催化活性的决定性因素,Au-载体间的相互作用对催化活性影响较大。
3. Au/FeOx催化剂的载体效应及其在催化二醇氧化制备内酯反应中的催化性能研究
采用商业纳米氧化铁γ-Fe2O3、α-Fe2O3和Fe3O4作为Au催化剂的载体,发现Au在Fe3O4上分散最好,平均粒径为4.7 nm,其次是Au/α-Fe2O3 (5.5 nm)和Au/γ-Fe2O3(6.7nm)。该系列纳米氧化铁负载的Au催化剂在催化1,4-丁二醇氧化中的TOF值顺序为：Au/Fe3O4>Au/α-Fe2O3> Au/γ-Fe2O3。尽管Au/Fe3O4有较高的初始活性,但由于Fe3O4易被氧化,在高温高压氧化性条件下反应一段时间后被氧化成Au/γ-Fe2O3,导致最终的1,4-丁二醇转化率和内酯得率下降。在不同的气氛(空气、Ar、H2)下处理的Au/Fe3O4催化剂中,Au/Fe3O4-H2上Au的平均粒径最小(2.7 nm),然而却表现出与Au/Fe3O4-Ar接近的催化性能,由此可以推测,在不同铁的氧化物上负载的Au催化剂中,催化活性的差异主要不是由于粒径效应,而是载体效应所引起的。
采用水热法合成的FeOx-NF在不同温度下焙烧表现出不同的晶型和形貌。室温下干燥的样品主要以Fe3O4存在,经焙烧后氧化成γ-Fe2O3,当焙烧温度高于573 K时γ-Fe2O3向α-Fe2O3转变,氧化铁形貌也由颗粒和片状的混合形态向纳米片状转变。使用这些氧化铁作为Au催化剂的载体,得到的催化剂上Au均匀地分散在载体表面,平均粒径约为5 nm。Au/FeOx-NF在催化空气选择性氧化1,4-丁二醇和1,5-戊二醇反应中表现出很高的催化活性,转化率和选择性均高于商业氧化铁负载的Au催化剂。在1,4-丁二醇氧化反应中,γ-Fe2O3负载的Au催化剂得到了很高的TOF值(Au/FeOx-573的TOF值为624 h-1)。Au/FeOx-NF在1,5-戊二醇氧化中也得到了>90%的转化率。催化剂表征结果显示,载体对Au的粒径和电子性质有显著影响,Au和载体间存在强相互作用。在y-Fe2O3负载的Au催化剂上电子由载体向Au转移,而α-Fe2O3则对氧化态的Au具有稳定作用,导致表面的Au部分以氧化态(Auδ+)存在。载体效应导致Au物种在颗粒大小和氧化态上有所差异,从而表现出二醇氧化反应的活性差别。该Au/γ-Fe2O3催化剂性质不同于商业γ-Fe2O3负载的Au催化剂,商业γ-Fe2O3负载的Au催化剂相比商业α-Fe2O3和Fe3O4负载的Au催化剂表现出差的催化活性；在Au/FeOx-NF中可能是因为γ-Fe2O3的特殊形貌和合成方法导致Au-Fe2O3相互作用增强,催化活性提高。
4.AuAIT催化剂的性质及其在催化空气氧化二醇制备内酯反应中的催化性能研究
在对Au催化剂载体碱性的研究中,我们采用γ-AlOOH和γ-Al2O3作为载体(AlT),载体采用普通的沉淀法制备。从室温到973 K升温处理,载体由γ-AlOOH分解为γ-Al2O3。γ-AlOOH可在573 K以下稳定,当温度达到773 K时,完全转化为γ-Al2O3。由CO2-TPD可知,γ-Al2O3(A1773、A1873、A1973)上只存在大量的弱碱性位和少量中等碱性位,而在γ-AlOOH中,A1573主要为中等碱性位,在A1373中除了中等碱性位还有一定量的强碱性位。用AlT负载的Au催化剂中,γ-Al2O3(A1773、A1873、A1973)上可得到粒径较小的Au颗粒(平均粒径约4 nm),而γ-AlOOH(Al373、Al573)负载的催化剂上Au的平均粒径为5-8 nm。AuAlT催化剂在催化1,4-丁二醇氧化反应中表现出比其他载体负载的Au催化剂更高的催化活性,其中AuAl773在反应1小时即可达到90%的转化率。尽管Au颗粒较大,AuAl373仍表现出较高的催化活性,反应1小时转化率达74%,所有的催化剂在反应8小时后均可达到100%的二醇转化率。由于载体有一定的碱性,而产物内酯在碱性条件下不稳定,容易发生水解,该系列催化剂的选择性较Au/TiO2和Au/FeOx低,且随着时间延长,选择性先升高后降低。由此推论碱性位有利于醇氧化的发生,但会牺牲内酯的选择性。除了用于催化1,4-丁二醇氧化,该催化剂在催化1,5-戊二醇和邻苯二甲醇氧化得到6-戊内酯和苯酞的反应中也表现出很高的活性。
5.Fe-Al-Ox复合载体的合成及其负载的金催化剂在催化空气氧化1,4-丁二醇制备γ-丁内酯反应中的催化性能研究
分别采用包覆法、Al2O3上浸渍Fe2O3以及Fe2O3上浸渍Al2O3的方法得到了FeAOx、Fe2O3/Al2O3和Al2O3/Fe2O3的铁铝复合氧化物载体,经表征发现,Fe2O3/Al2O3和Al2O3/Fe2O3中Fe2O3与Al2O3只是简单的混合,Fe2O3与Al2O3未发生明显相互作用,而FeAlOx中Al2O3包裹在Fe2O3表面,TEM未观察到孤立的Fe2O3颗粒。XPS也表明FeAlOx表面富集Al,其表面Fe／Al比(1：18)最低,远低于体相(1：3.4),同时也比其他两种载体要低。FeAlOx负载的Au催化剂上Au颗粒均匀分散在载体表面,平均粒径为3.5 nm, Fe2O3的晶型为γ-Fe2O3, Au与载体间存在相互作用。FeAlOx负载的Au催化剂在1,4-丁二醇氧化反应中表现出很高的催化活性,比机械混合的Au/Fe2O3和Au／Al2O3要高,甚至接近活性最高的Au/Al2O3催化剂,而选择性要高于Au/Al2O3和Au/Fe2O3。该系列Fe-Al-O负载的Au催化剂的活性顺序为Au/FeAlOx> Au/Fe2O3/Al2O3-Au/Fe2O3+ Au/Al2O3> Au/Al2O3/Fe2O3。
对Au/FeAlOx催化剂的Fe/Al比进行考察后发现,当Fe/Al从1：1变为1：16时,表面Fe／Al比从1：8降低到1：41。当Fe/Al=1：1时,Al2O3的量不足以将所有的Fe203覆盖,由透射电镜图中可以观察到孤立的Fe2O3颗粒,而增加Al含量至Fe／Al=1：4,Al2O3将Fe2O3全部覆盖,继续增加Al含量,Al2O3过多,导致与Fe的作用减弱,不利于催化反应的进行,且由于其碱性较强,对内酯选择性会有不利影响。因此Fe／Al比为1：4的催化剂在1,4-丁二醇氧化反应中表现出最高的催化活性和内酯选择性。
The lactones and their derivatives are widely distributed in nature. The lactone ring exists in the molecules of many bioactive substances and metabolic intermediates. Due to their high boiling point, solubility, conductivity and stability, the lactones are widely used as solvent, extraction agent and also can be used for the synthesis of a variety of polymers. In this dissertation, the nano gold catalysts were used to catalyze the aerobic oxidative dehydrogenation of diols to lactones. The reaction was carried out at low temperature with air as oxidant, which is a clean route in accordance with the demand of green chemistry and sustainable development.
The nano gold is a catalyst with high performance in the low temperature CO oxidation, oxidation of alcohols, water-gas shift reaction and selective hydrogenation ofα,β-unsaturated aldehydes or ketones. Due to their low temperature activity and high selectivity, the gold catalysts are becoming more and more important. The gold particle size, gold electronic state and support effect was studied in this dissertation to investigate the active sites of gold catalyst and the reaction mechanism.
Gold catalysts prepared in this dissertation showed high activity in the oxidative dehydrogenation of a series of diols such as 1,4-butanediol,1,5-pentanediol and 1,2-benzenedimethanol to y-butyrolactone,δ-valerolactone and phthalanone. The preparation conditions of the catalysts, support compositions, support morphology and support crystal phase were optimized, and finally multi-component oxide support were prepared to give catalysts with high activity, selectivity and stability. At the same time, the active sites of the gold catalysts, as well as the support effect were discussed and the following results were obtained.
1. Influence of the preparation conditions and catalyst compositions on the catalytic performance of Au/TiO2 catalysts in the oxidative dehydrogenation of diols to lactones
The commercial Degussa P25 was utilized as support, and the gold catalysts were prepared by the homogeneous deposition-precipitation method (HDP) using urea as precipitation agent. Nano sized gold particles were obtained with average particle size of about 5 nm. There was interaction between gold and the support. The catalysts showed high activity in the oxidation of 1,4-butanediol and 1,5-pentanediol to the corresponding lactones. Calcination temperature had significant effect on the catalytic activity of the catalysts, and it was found that the catalyst with 3-8% gold loading calcined at 573-673 K gave high activity. From the characterization results it can be found that when calcined at high temperature, gold particles tended to aggregate and form large particles, but when the calcination temperature was below 573 K, gold species were not completely reduced, and there were still some oxidized gold (Au3+). For catalysts with gold loading higher than 8%, gold particles tended to aggregate and catalytic activity dropped. From the above results it can be concluded that the surface metallic gold species with small particle size were the active species.
2. Properties and catalytic performance of gold catalysts on different oxide support (Au/MOx)
The transition metal oxides and main group metal oxides were used as support for gold catalysts, and most of them showed high activity in the oxidative dehydrogenation of 1,4-butanediol to y-butyrolactone.
Among the transition metal oxide supported gold catalysts, Au/TiO2, Au/MnOx, Au/Fe2O3, Au/Co3O4, Au/ZnO, Au/CeO2 and Au/ZrO2 were highly active with both diol conversion and lactone selectivity above 90% after 8 hours'reaction, especially Au/TiO2 and Au/MnOx, whose conversion were above 80% after 4 hours'reaction. Due to its large gold particle size and low surface gold content, Au/NiO showed much lower activity.
Activity of Au/SnO2 was even superior to some of the transition metal oxide supported gold catalysts, with conversion of 82% after 4 hours'reaction and 99% after 8 hours'reaction. When catalyzed by Au/Mg(OH)2, the formed y-butyrolactone would be hydrolyzed due to the basicity of Mg(OH)2. Although A12O3 was always considered as inert in gold catalysis, Au/Al2O3 showed high activity with 4 hour and 8 hour conversion of 58% and 99%, respectively.
For the above gold catalysts on active support, the average gold particle size was in the range of 4-7 nm, and the support particle diameter was about 10-30 nm. The surface gold content was higher than that in bulk, and gold particles were highly dispersed on the surface of the support. Most of the gold can be deposited onto the support to form gold-support interaction. From the BET results it can be inferred that although surface area of some support oxides were low, gold catalysts with high activity can still be obtained on them.
From the above results, it can be concluded that gold particle size must be small enough to give high activity. However, the gold particle size was not the decisive factor and the type of the support was also important. Pore properties were not as important as support effect, and there was interaction between gold species and the support.
3. Support effect of Au/FeOx catalysts and their catalytic performance in the oxidative dehydrogenation of diols
The commercial nano iron oxidesγ-Fe2O3,α-Fe2O3 and Fe3O4 were utilized as support for gold catalysts, and it was found that the smallest gold particles were obtained on Fe3O4 with average gold diameter of 4.7 nm, and then the Au/α-Fe2O3 (5.5 nm), and the largest gold particles were got on Au/γ-Fe2O3 (6.7 nm). TOF values of the catalysts were in the order:Au/Fe3O4> Au/α-Fe2O3> Au/γ-Fe2O3. Although Au/Fe3O4 had the highest initial activity, Fe3O4 would be oxidized toγ-Fe2O3 during the reaction with high temperature and oxidative atmosphere, leading to the loss in activity and final lactone yield. For Au/Fe3O4 catalysts treated under different atmospheres, Au/Fe3O4-H2 had the smallest gold particle size (2.7 nm), but its catalytic behavior was similar to that of Au/Fe3O4-Ar. Therefore it was inferred that the different activity of the Au/FeOx with different crystal phase was due to the variation in support properties other than the gold particle size.
FeOx-NF was synthesized by a hydrothermal method, and showed different crystal phase and morphology when calcined at different temperatures. The room temperature treated sample was in the form of Fe3O4, and it was oxidized toγ-Fe2O3 when calcined at 573 K in air. Further increase in calcination temperature led to the crystal transformation fromγ-Fe2O3 toα-Fe2O3, and the simultaneous transformation of iron oxide particles to nano flakes. The FeOx-NF supported gold catalysts were more active than those supported on commercial iron oxides. When FeOx-NF in the. form ofγ-Fe2O3 was used as support for gold catalysts, it showed high TOF value (624 h-1 for Au/FeOx-573). According to the characterization results, the gold particles were evenly distributed on the support with average particle size about 5 nm, and the support had significant influence on the gold particle size distributions and electronic properties. There was strong gold-support interaction, and on Au/γ-Fe2O3, electrons were transferred from the support to gold, leading to the formation of negatively charged gold (Auδ-). On contrary,α-Fe2O3 can stabilize the oxidized gold species. Support was responsible for the variation in gold particle size and oxidation state, and thus the differences in catalytic activity. In contrast to commercial iron oxide supported gold catalysts, the Au/γ-Fe2O3 showed higher activity than Au/α-Fe2O3, and this may be due to the morphology change and support synthetic method utilized in this dissertation.
4. Catalytic properties of AuAlT catalysts in the oxidative dehydrogenation of diols to lactones
γ-AlOOH andγ-Al2O3 (AIT) were utilized as support for gold catalysts to investigate the influence of support basicity. The support was prepared by a simple deposition method, and by elevating pretreating temperature from room temperature to 973 K, AIT dehydroxylated fromγ-AlOOH toγ-Al2O3.γ-AlOOH was stable below 573 K, and then transformed toγ-Al2O3 at 773 K. According to the CO2-TPD results, there were mainly weak basic sites onγ-Al2O3 (A1773, A1873 and A1973), while forγ-AlOOH, there were medium basic sites on A1573 and strong basic sites on A1373. Small gold particle size can be obtained onγ-Al2O3 with average diameter about 4nm. Larger gold particles were got on y-AlOOH (A1373, A1573), and the average gold diameter was 5-8nm. Catalytic activity of AuAlT catalysts was higher than that of other oxide supported gold catalysts (Au/TiO2 and Au/FeOx). Conversion of AuA1773 reached 90% after 1 hour's reaction. Although with larger gold particle size, AuA1373 still showed high activity with 74% conversion after 1 hour's reaction. Conversion of all the catalysts can achieve 100% after 8 hours' reaction. Due to the basicity of the support, the y-butyrolactone product would be hydrolyzed, which led to the drop in lactone selectivity as compared to Au/TiO2 and Au/FeOx. Selectivity of AuAlT increased firstly and then dropped with the prolonging of reaction time. Therefore, it was concluded that basicity was beneficial to the oxidation of alcohols; however, it was detrimental to the lactone selectivity. AuAlT can also be used for the oxidation of other diols, for example,1,5-pentanediol and 1,2-benzedimethanol.
5. Synthesis of multi-component Fe-Al-O oxides and their application as support for gold catalysts in the oxidative dehydrogenation of 1,4-butanediol to y-butyrolactone
The multi-component Fe-Al-O oxides were prepared by encapsulation (FeAlOx) and impregnation methods (Fe2O3/Al2O3 and Al2O3/Fe2O3). According to the characterization results, it was found that when prepared by the impregnation method, there was no interaction between Fe2O3 and Al2O3, and the support was the simple mixture of Fe2O3 and Al2O3. For FeAlOx, Fe2O3 was encapsulated by Al2O3, and there were no isolated Fe2O3 particles observed, indicating that interaction was formed between Fe2O3 and Al2O3. It was also confirmed by the XPS results that FeAlOx surface was enriched with Al, due to its low surface Fe/Al ratio (1:18), which was far lower than that of the bulk (1:3.4) and the other two support prepared by the impregnation method. Crystal phase of FeAlOx wasγ-Fe2O3 andγ-Al2O3. Gold can be highly dispersed on the support surface with average diameter of 3.5 nm, and gold-support interaction was observed. Au/FeAlOx showed high activity in the oxidative dehydrogenation of 1,4-butanediol, and its catalytic activity was better than that of the mixture of Au/Fe2O3 and Au/Al2O3, very close to that of the most active Au/Al2O3 catalyst. In addition, its selectivity was higher than that of Au/Al2O3 and Au/Fe2O3. For Fe-Al-O supported gold catalysts, the activity was in the order: Au/FeAlOx> Au/Fe2O3/Al2O3-Au/Fe2O3+Au/Al2O3> Au/Al2O3/Fe2O3.
By adjusting the Fe/Al molar ratio of Au/FeAlOx catalysts from 1:1 to 1:16, the surface Fe/Al ratio changed from 1:8 to 1:41. When Fe/Al was 1:1, the amount of Al2O3 was not enough to encapsulate all the Fe2O3 particles and it can be seen from the TEM images that there were some isolated Fe2O3 particles. Increasing Al content to Fe/Al ratio of 1:4, Al2O3 can cover all the Fe2O3, however, further increase in Al content would lead to the weakening of the Fe-Al interaction and the stronger support basicity, which was not beneficial to the reaction. The optimized Fe/Al was found to be 1:4.
引文
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