改性ZrO_2基催化剂催化1，4-丁二醇选择性脱水制3-丁烯-1-醇
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摘要
3-丁烯-1-醇(BTO)是一种附加值极高的不饱和醇类精细化学品,性质活泼,可参与多种反应,广泛应用于食用香精、农化产品、药物合成等领域,是合成杂环衍生物类新药物的重要中间体,其用量逐年增加。以固体氧化物为催化剂的1,4-丁二醇(BDO)气相选择性脱水合成BTO具有反应条件温和、环境友好、产物易分离等优点。然而,由于BDO分子中存在两个等效位置的羟基,其脱水反应在热力学上可向两个方向进行,一是分子内环化脱水生成四氢呋喃(THF),二是分子中的端羟基与相邻碳原子的β-H脱水得到BTO。如何通过催化剂织构、结构及表面性质等的调控,高选择性地合成目标产物BTO,抑制竞争副产物THF的生成,具有重要应用前景和理论价值。
本论文在课题组前期研究的基础上,首先制备了多种单一组分氧化物催化剂,考察其催化BDO气相脱水性能,探讨催化剂表面性质对脱水反应活性和产物分布的影响。以此为基础,采用浸渍法制备了一系列表面改性的ZrO2基催化剂,通过对引入组分种类,含量以及焙烧温度的调控,制得一系列酸碱双功能催化剂,在酸碱活性中心的协同催化作用下,提高了目标产物BTO的收率。本工作采用多种表征手段,结合催化反应评价结果,较系统地研究了BDO选择性脱水合成BTO活性中心结构和酸碱协同催化机制。论文的主要研究结果如下：
1、研究了多种单一组分氧化物(A12O3, MgO, CaO, ZrO2和SiO2催化BDO气相脱水性能。结果表明,催化剂表面酸碱性质对BDO脱水反应活性以及产物分布有重要的影响。表面以酸性位点为主的催化剂(如Al2O3)表现出高的BDO转化率,但BTO的选择性很低；而以碱性位点为主的催化剂上(如CaO, MgO),目标产物BTO的选择性较高,但催化活性较差。在考察的多种单一组分催化剂中,ZrO2同时具有酸性位点和碱性位点,表现出最优的催化BDO选择性脱水合成BTO性能。
2、制备了碱土类金属氧化物(CaO, SrO, BaO)改性的ZrO2酸碱双功能催化剂,借助X射线衍射(XRD)、低温N2物理吸附、NH3和CO2程序升温脱附(NH3-TPD, CO2-TPD)等手段表征了催化剂的织构、结构以及表面酸碱性质,并考察了其催化BDO选择性脱水合成BTO的反应性能。碱土类金属氧化物的引入对ZrO2基催化剂表面的酸性位点和碱性位点有重要影响。Ca2+半径与Zr4+相近,可进入ZrO2晶格形成Ca-O-Zr结构,由于电荷分布不均衡而产生了新的酸性位点,在ZrO2表面引入大量碱性位点的同时保持了较高的酸密度,催化剂表现出高的催化活性和BTO选择性。在相同的制备条件下,半径较大的Sr2+和Ba2+难以进入ZrO2晶格,而是生成了相应的锆酸盐,导致ZrO2表面的酸密度降低,碱性位点数量也明显低于CaO改性ZrO2催化剂,催化活性和BTO选择性较低。
3、在上述工作的基础上,制备了一系列CaO改性的ZrO2基催化剂,考察了CaO含量和焙烧温度对催化剂表面性质及脱水性能的影响。当CaO含量低于12.5%,Ca2+可取代部分Zr4+形成Ca-O-Zr结构,以高分散形态存在于样品中,使得催化剂的酸性位点数量较高,碱性位点数量较本体ZrO2大幅增加,表现出高的BDO转化率和BTO选择性。继续增加CaO含量,CaO发生聚集且生成相应的锆酸盐,酸性和碱性位点数量呈现下降趋势, BDO转化率和BTO选择性也随之下降。之后在催化活性中心结构的研究中,结合NH3和CO2为载气的中毒实验结果得出BDO选择性脱水生成BTO的催化活性中心为酸碱协同中心,该活性中心由两个酸性位点和一个碱性位点组成。其酸性位点和碱性位点分别活化BDO分子中的端羟基和β-H以脱水形成BTO。为进一步研究催化剂表面碱强度对催化性能的影响,将表面碱性较为温和的MgO引入到ZrO2表面,结果表明催化剂表面的弱碱性位点更加有利于酸碱活性中心的协同催化作用。
4、基于对上述酸碱协同催化规律的认识,结合本实验室前期对SiO2-ZrO2复合氧化物的研究,制备了CaO改性的SiO2-ZrO2复合氧化物催化剂。复合氧化物中Zr-O-Si结构的形成大大提高了催化剂的表面酸性中心数量,进一步引入CaO在催化剂表面产生了大量的酸碱协同活性中心,不仅表现出了高的BDO转化率和BTO选择性,而且明显降低了BDO完全转化的反应温度。在反应温度为325℃时,BTO的收率最高为58%。
3-Buten-1-ol (BTO) is a valuable chemical that is widely used in food flavoring, agricultural products, and especially in the medical field due to its active character. In addition, served as a valuable intermediate for synthesizing heterocyclic drugs, the market demand for BTO has been increasing year by year. The method used for BTO synthesis from1,4-butanediol (BDO) selective dehydration offers some advantages that include mild reaction conditions, a simple experimental procedure, and environmental friendliness. However, this approach has two favorable thermodynamic pathways. One is the intramolecular cyclodehydration of BDO to give tetrahydrofuran (THF), which in this context is a byproduct, while the other is the dehydration of BDO involving the terminal hydroxyl group and a β-H atom on the adjacent carbon atom. To increase BTO yield by this reaction pathway, particular attention were paid to prepare appropriate catalysts. Thus, it is a challenging task to obtain a catalyst that favors producting BTO by dehydration of BDO via regulating and controlling the texture, the structure, and surface properties of the materials.
On the basis of our previous studies, a varity of single-component oxide catalysts were prepared. The effects of catalysts surface properties on catalytic activity were investigated. Then, a series of modified ZrO2catalysts were prepared by the impregnation method and the acid-base properties of the catalysts can be controlled by the amount of introduction component and calcination temperature. Through the synergistic interaction of the acid and base sites, the yield of BTO can be increased effectively. Combined with the catalytic performances evaluation, the thorough study of the BDO dehydration to BTO was investigated to infer and clarify the catalytic mechanism. The main results are listed as follows:
1. A variety of single-component oxide catalyst (Al2O3, MgO, CaO, ZrO2and SiO2) were investigated in BDO selective dehydration reaction. The results show that the acid-base property of the catalysts plays an important role in the catalytic activity and the product distribution. The catalysts as Al2O3, whose surface mainly consists of acid sites, show the high BDO conversion but the low BTO selectivity; while the catalysts (MgO, CaO), whose surface mainly consists of base sites, exhibit the high BTO selectivity but the low catalytic activity. Among the single-component oxide catalysts studies, the ZrO2catalysts have the best catalytic activity in BDO selective dehydration reaction due to their acid-base bifunctional properties on the surface.
2. The acid-base bifunctional ZrO2catalysts modified by different alkaline earth metal (CaO, SrO, BaO) were prepared and characterized using N2physisorption, XRD, FT-IR spectra, NH3-TPD and CO2-TPD techniques to obtain the texture, the structure, and surface properties of the catalysts. On basis of characterizations, the catalytic activities of BDO selective dehydration to BTO over the acid-base bifunctional catalysts were studied in details. The result indicates that the alkaline earth metals make a great impact on the acid-base properties of ZrO2-based catalysts. The Ca2+ion can enter into the ZrO2crystal lattice to form Ca-O-Zr hetero-linkages easily. And the hetero-linkages in binary complex oxides lead to the uneven distribution of charges and generate new acid sites. That is to say, the introduction of appropriate CaO not only increases alkali density, but also keeps acidic sites on ZrO2surface. The synergistic effect of the acid-base sites shows the high catalytic activity and BTO selectivity. Under the same conditions, the Sr2+and Ba2+ions with the large radius is difficult to enter into the ZrO2crystal lattice, and then to form zirconate on ZrO2surface. The zirconate decreases the amounts of acid and base sites in comparison to unmodified ZrO2, and induces the low catalytic activity and BTO selectivity.
3. Based on the above work, the effect of different CaO content and calcination temperature of CaO-ZrO2catalyst on the acid-base properties and catalytic performance were investigated. With CaO content lower than12.5%, Ca2+replace the Zr4+to form the Ca-O-Zr structure that not only increase alkali density dramaticlly, but also keep acidic sites on ZrO2surface, which exhibits the high catalytic activity and BTO selectivity. With the further increase in CaO content, the CaO begins to aggregate and generate CaZrO3, and then the total amount of acidic and basic sites decreases significantly. Thus, the BDO conversion and the BTO selectivity decrease obviously due to the decrease of acid-base active center. Combining the studies of the structure of active center and the poisoning experiments used NH3or CO2as cattier gases, it is concluded that the acid-base properties of the CaO-ZrO2catalysts have significant influence in the dehydration of BDO. Every active center forming BTO is composed of two acidic sites and one basic site. The acidic sites act as anchoring sites for OH group to activate BDO while the basic sites interacted with β-hydrogen to form BTO. In order to determine the relationship between the basic property of the catalyst and the catalytic dehydration performance, the mild basicity, MgO, is further introduced to ZrO2surface, and the result shows that the weakly basic sites is favorable to the acid-base synergetic catalytic activity.
4. After we summarized the conclusions from the acid-base synergetic catalytic activity, a series of SiO2-ZrO2catalys modified by CaO were prepared in BDO selective dehydration reaction. The results show that the formation of Zr-O-Si hetero-linkages can increase the acidic sites greatly, and the further CaO addition promotes the formation of acid-base synergetic active centers. These catslysts not only exhibit the high BDO conversion and BTO selectivity, but also decrease the complete conversion temperature of BDO. When the reacted temperature is325℃, the highest yield of BTO attains to58%.
本论文在课题组前期研究的基础上,首先制备了多种单一组分氧化物催化剂,考察其催化BDO气相脱水性能,探讨催化剂表面性质对脱水反应活性和产物分布的影响。以此为基础,采用浸渍法制备了一系列表面改性的ZrO2基催化剂,通过对引入组分种类,含量以及焙烧温度的调控,制得一系列酸碱双功能催化剂,在酸碱活性中心的协同催化作用下,提高了目标产物BTO的收率。本工作采用多种表征手段,结合催化反应评价结果,较系统地研究了BDO选择性脱水合成BTO活性中心结构和酸碱协同催化机制。论文的主要研究结果如下：
1、研究了多种单一组分氧化物(A12O3, MgO, CaO, ZrO2和SiO2催化BDO气相脱水性能。结果表明,催化剂表面酸碱性质对BDO脱水反应活性以及产物分布有重要的影响。表面以酸性位点为主的催化剂(如Al2O3)表现出高的BDO转化率,但BTO的选择性很低；而以碱性位点为主的催化剂上(如CaO, MgO),目标产物BTO的选择性较高,但催化活性较差。在考察的多种单一组分催化剂中,ZrO2同时具有酸性位点和碱性位点,表现出最优的催化BDO选择性脱水合成BTO性能。
2、制备了碱土类金属氧化物(CaO, SrO, BaO)改性的ZrO2酸碱双功能催化剂,借助X射线衍射(XRD)、低温N2物理吸附、NH3和CO2程序升温脱附(NH3-TPD, CO2-TPD)等手段表征了催化剂的织构、结构以及表面酸碱性质,并考察了其催化BDO选择性脱水合成BTO的反应性能。碱土类金属氧化物的引入对ZrO2基催化剂表面的酸性位点和碱性位点有重要影响。Ca2+半径与Zr4+相近,可进入ZrO2晶格形成Ca-O-Zr结构,由于电荷分布不均衡而产生了新的酸性位点,在ZrO2表面引入大量碱性位点的同时保持了较高的酸密度,催化剂表现出高的催化活性和BTO选择性。在相同的制备条件下,半径较大的Sr2+和Ba2+难以进入ZrO2晶格,而是生成了相应的锆酸盐,导致ZrO2表面的酸密度降低,碱性位点数量也明显低于CaO改性ZrO2催化剂,催化活性和BTO选择性较低。
3、在上述工作的基础上,制备了一系列CaO改性的ZrO2基催化剂,考察了CaO含量和焙烧温度对催化剂表面性质及脱水性能的影响。当CaO含量低于12.5%,Ca2+可取代部分Zr4+形成Ca-O-Zr结构,以高分散形态存在于样品中,使得催化剂的酸性位点数量较高,碱性位点数量较本体ZrO2大幅增加,表现出高的BDO转化率和BTO选择性。继续增加CaO含量,CaO发生聚集且生成相应的锆酸盐,酸性和碱性位点数量呈现下降趋势, BDO转化率和BTO选择性也随之下降。之后在催化活性中心结构的研究中,结合NH3和CO2为载气的中毒实验结果得出BDO选择性脱水生成BTO的催化活性中心为酸碱协同中心,该活性中心由两个酸性位点和一个碱性位点组成。其酸性位点和碱性位点分别活化BDO分子中的端羟基和β-H以脱水形成BTO。为进一步研究催化剂表面碱强度对催化性能的影响,将表面碱性较为温和的MgO引入到ZrO2表面,结果表明催化剂表面的弱碱性位点更加有利于酸碱活性中心的协同催化作用。
4、基于对上述酸碱协同催化规律的认识,结合本实验室前期对SiO2-ZrO2复合氧化物的研究,制备了CaO改性的SiO2-ZrO2复合氧化物催化剂。复合氧化物中Zr-O-Si结构的形成大大提高了催化剂的表面酸性中心数量,进一步引入CaO在催化剂表面产生了大量的酸碱协同活性中心,不仅表现出了高的BDO转化率和BTO选择性,而且明显降低了BDO完全转化的反应温度。在反应温度为325℃时,BTO的收率最高为58%。
3-Buten-1-ol (BTO) is a valuable chemical that is widely used in food flavoring, agricultural products, and especially in the medical field due to its active character. In addition, served as a valuable intermediate for synthesizing heterocyclic drugs, the market demand for BTO has been increasing year by year. The method used for BTO synthesis from1,4-butanediol (BDO) selective dehydration offers some advantages that include mild reaction conditions, a simple experimental procedure, and environmental friendliness. However, this approach has two favorable thermodynamic pathways. One is the intramolecular cyclodehydration of BDO to give tetrahydrofuran (THF), which in this context is a byproduct, while the other is the dehydration of BDO involving the terminal hydroxyl group and a β-H atom on the adjacent carbon atom. To increase BTO yield by this reaction pathway, particular attention were paid to prepare appropriate catalysts. Thus, it is a challenging task to obtain a catalyst that favors producting BTO by dehydration of BDO via regulating and controlling the texture, the structure, and surface properties of the materials.
On the basis of our previous studies, a varity of single-component oxide catalysts were prepared. The effects of catalysts surface properties on catalytic activity were investigated. Then, a series of modified ZrO2catalysts were prepared by the impregnation method and the acid-base properties of the catalysts can be controlled by the amount of introduction component and calcination temperature. Through the synergistic interaction of the acid and base sites, the yield of BTO can be increased effectively. Combined with the catalytic performances evaluation, the thorough study of the BDO dehydration to BTO was investigated to infer and clarify the catalytic mechanism. The main results are listed as follows:
1. A variety of single-component oxide catalyst (Al2O3, MgO, CaO, ZrO2and SiO2) were investigated in BDO selective dehydration reaction. The results show that the acid-base property of the catalysts plays an important role in the catalytic activity and the product distribution. The catalysts as Al2O3, whose surface mainly consists of acid sites, show the high BDO conversion but the low BTO selectivity; while the catalysts (MgO, CaO), whose surface mainly consists of base sites, exhibit the high BTO selectivity but the low catalytic activity. Among the single-component oxide catalysts studies, the ZrO2catalysts have the best catalytic activity in BDO selective dehydration reaction due to their acid-base bifunctional properties on the surface.
2. The acid-base bifunctional ZrO2catalysts modified by different alkaline earth metal (CaO, SrO, BaO) were prepared and characterized using N2physisorption, XRD, FT-IR spectra, NH3-TPD and CO2-TPD techniques to obtain the texture, the structure, and surface properties of the catalysts. On basis of characterizations, the catalytic activities of BDO selective dehydration to BTO over the acid-base bifunctional catalysts were studied in details. The result indicates that the alkaline earth metals make a great impact on the acid-base properties of ZrO2-based catalysts. The Ca2+ion can enter into the ZrO2crystal lattice to form Ca-O-Zr hetero-linkages easily. And the hetero-linkages in binary complex oxides lead to the uneven distribution of charges and generate new acid sites. That is to say, the introduction of appropriate CaO not only increases alkali density, but also keeps acidic sites on ZrO2surface. The synergistic effect of the acid-base sites shows the high catalytic activity and BTO selectivity. Under the same conditions, the Sr2+and Ba2+ions with the large radius is difficult to enter into the ZrO2crystal lattice, and then to form zirconate on ZrO2surface. The zirconate decreases the amounts of acid and base sites in comparison to unmodified ZrO2, and induces the low catalytic activity and BTO selectivity.
3. Based on the above work, the effect of different CaO content and calcination temperature of CaO-ZrO2catalyst on the acid-base properties and catalytic performance were investigated. With CaO content lower than12.5%, Ca2+replace the Zr4+to form the Ca-O-Zr structure that not only increase alkali density dramaticlly, but also keep acidic sites on ZrO2surface, which exhibits the high catalytic activity and BTO selectivity. With the further increase in CaO content, the CaO begins to aggregate and generate CaZrO3, and then the total amount of acidic and basic sites decreases significantly. Thus, the BDO conversion and the BTO selectivity decrease obviously due to the decrease of acid-base active center. Combining the studies of the structure of active center and the poisoning experiments used NH3or CO2as cattier gases, it is concluded that the acid-base properties of the CaO-ZrO2catalysts have significant influence in the dehydration of BDO. Every active center forming BTO is composed of two acidic sites and one basic site. The acidic sites act as anchoring sites for OH group to activate BDO while the basic sites interacted with β-hydrogen to form BTO. In order to determine the relationship between the basic property of the catalyst and the catalytic dehydration performance, the mild basicity, MgO, is further introduced to ZrO2surface, and the result shows that the weakly basic sites is favorable to the acid-base synergetic catalytic activity.
4. After we summarized the conclusions from the acid-base synergetic catalytic activity, a series of SiO2-ZrO2catalys modified by CaO were prepared in BDO selective dehydration reaction. The results show that the formation of Zr-O-Si hetero-linkages can increase the acidic sites greatly, and the further CaO addition promotes the formation of acid-base synergetic active centers. These catslysts not only exhibit the high BDO conversion and BTO selectivity, but also decrease the complete conversion temperature of BDO. When the reacted temperature is325℃, the highest yield of BTO attains to58%.
引文
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