光催化合成芳香醛缩醛及其反应行为研究
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摘要
芳香醛缩醛作为一类特殊的精细化学品,在有机合成和化工生产领域具有极其重要的应用价值。本论文首次采用自行设计的UV-LED恒温石英光催化反应器将非均相光催化反应技术应用于芳香醛缩醛化反应体系,制备了不同掺杂的纳米TiO2光催化剂并对其光催化活性进行了评价。高选择性地合成了苯甲醛二乙缩醛(BDA)及其不同取代的缩醛衍生物,优化了合成反应工艺,探讨了不同取代基的电子效应对反应活性和产率的影响,并提出了光催化苯甲醛缩醛反应的可能机理。
采用溶胶-凝胶法,分别以钛酸四正丁酯[Ti(OC4H9)4]为前驱体,氨水(NH3)为氮源,六水合氯铂酸(H2PtCl6·6H2O)为铂源,在一定条件下制备了纯TiO2、N/TiO2、Pt/TiO2和PtN/TiO2晶体粉末,并通过XRD、XPS、TEM等分析测试手段对其一系列物理特性进行了表征。XRD及TEM测试结果表明：溶胶-凝胶法制备的各种纳米TiO2样品粉末主要为单一锐钛矿晶型的球状颗粒且分布均匀,平均粒径在20nm左右。以紫外光催化降解亚甲基蓝水溶液为模型反应,评价了各种掺杂改性的纳米Ti02和商用Degussa P25的光催化性能,结果表明：各种纳米TiO2粉末对亚甲基蓝均有较好的光催化降解效果,其中混晶型Degussa P25的光催化效率最高。
自行设计了配备光强可调式UV-LED阵列光源的恒温石英玻璃光催化反应系统。在此基础上,采用Degussa P25作为光催化剂,在无水乙醇中研究了苯甲醛光催化合成苯甲醛二乙缩醛(BDA)的反应行为。讨论了氮气是否饱和、反应液pH、紫外光强、反应时间、反应物初始浓度、催化剂用量等因素以及不同类型反应器对苯甲醛二乙缩醛的产率及选择性的影响,优化了反应条件。并考察了甲醇、乙醇、异丙醇等不同醇溶剂对苯甲醛的光催化缩醛反应活性及选择性的影响,发现不同醇溶剂中的缩醛反应速率与醇的pKa值有关,pKa值越小,醇越活泼,反应速率越快。实验结果表明：在反应液pH为7.86,紫外光强为0.6mw/cm2,苯甲醛初始浓度为0.05mol/L, TiO2(P25)催化剂用量为5.0g/L,反应15min条件下,苯甲醛二乙缩醛的产率和选择性最好,GC产率高达99.86%,选择性为100%,且重复性好。
在上述优化条件下,考察了无水乙醇中对位不同取代的苯甲醛光催化缩醛反应行为,讨论了苯环对位取代基的电子效应对缩醛反应活性及选择性的影响。苯环对位为供电子基团(EDG)取代比为吸电子基团取代(EWG)更利于发生缩醛反应,且供电子能力越弱,缩醛产率越高。结合传统缩醛反应机理和非均相光催化反应的特点,探讨了光催化芳香醛缩醛反应机理,与传统质子酸活化羰基不同,芳香醛基在光生电子和空穴的作用下,选择性的生成α-羟基自由基是引发反应的关键步骤。
此外,本文采用自制的光催化微反应器进行苯甲醛与乙醇的光催化反应行为和缩醛反应研究。考察了光强、反应时间及反应器尺寸对微反应器中苯甲醛的光催化缩醛反应影响,结果表明微反应器中不仅发生苯甲醛缩醛反应,更容易发生苯甲醛的还原反应。光强越大、反应时间越长越容易发生苯甲醛还原。而反应器尺寸越大越利于光催化缩醛反应的进行。
纳米Ti02光催化技术为苯甲醛缩醛及其衍生物的合成提供了一种绿色、高效、简便且价廉的合成方法,对缩醛的合成生产具有重要的理论研究意义和一定的实用价值。
Aromatic acetals as a specific kind of fine chemicals has very significant appli-cation value in organic synthesis and industrial production.In this paper, heterogene-ous photocatalytic technology is firstly applied to the acetal reaction in a self-designed constant temperature quartz-glass photocatalytic reactor with UV-LED as light source. Different kinds of TiO2photocatalysis have been prepared and their photocatalysis properties were evaluated.Benzaldehyde Diethyl Acetal (BDA) has been high selec-tively synthesized.the condition of acetal reaction has been optimized. The photocata-lytic acetal reaction of benzaldehyde with different substitutions have also been rese-arched and the mechanism was discussed.
Pure TiO2,N/TiO2,Pt/TiO2and PtN/TiO2were prepared by sol-gel method with tetrabutyltitanate[Ti(OC4H9)4] as a precursor,ammonia(NH3)as nitro source,and six hydration chlorine platinum acid(H2PtCl6·6H2O) as platinuim source respectively.The properties of the various kinds of TiO2were studied by different technologies, such as XRD,XPS and TEM.X-ray diffraction(XRD) and Transmission Electorn Microscope (TEM) showed that the self-synthesized TiO2by sol-gel method mainly are composed with anatase globular particles,and average particle size is less than20nm.The photo-catalytic activities of self-synthesized TiO2and commercial mixed crystal-Degussa P25were evaluated by photo-degradation of methylene blue solution and the result showed that all catalysts demonstrated good capacity of photodagradation,in which mixed crystal-Degussa P25is the best.
We have designed the photocatalytic reaction system equipped with adjustable light intensity UV-LED array light source and constant temperature quartz glass reactor. Based on the system, photocatalytic synthetic reaction behavior of Benzaldehyde Diethyl Acetal(BDA) is studied in anhydrous alcohol with Degussa P25as a catalyst from benzaldehyde. The effects of reaction solution pH, light intensity, reaction time, concentration of substrate, loading of TiO2and dimension of the reactor on reaction rate and yield of BDA were evaluated. Several alcohols such as methanol. ethanol and isopropanol as reactant of the acetal reaction with benzaldehyde were also studied. The yield of BDA could reach high up to100%under the condition of solution pH7.86, TiO2concentration:5.0g/L,benzaldehyde initial concentration:0.05mol/L, light intensity:0.6mw/cm2,temperature:30℃.reaction time:15min. Additionally,the reaction rate was also related to the pKa of the alcohols, the smaller pKa value, the more lively alcohol, the higher the reaction activity.
Furthermore, we investigated the synthesis of aromatic aldehyde with different substitutions under the optimized conditions mentioned above. The results showed that benzaldehyde with EDG substitutions in/P-phenyl ring have good efficiency in the photocatalytic acetal reaction, acetal yield is in the range of83.89%-58.20%,. Chlorine substituted benzaldehyde showed high reaction activity as the lone-electron pair on Chlorine atom give strong electrophobic effect on the phenyl ring, the yield of acetal product reached to96.84%. While acetal reactions of benzaldehyde with EDG substitutions in P-phenyl ring were relatively difficult to take place. The mechanism of the photocatalytic acetal reaction was discussed based on the facts mentioned above.
In addition, benzaldehyde photocatalytic reaction behavior and acetal reaction in ethanol with self-made photocatalytic micro reactors was studied in this paper. The effects of light intensity, reaction time and the size of photocatalytic reactor on benzaldehyde acetal reaction was investigated. The results showed that not only benzaldehyde acetal but reduction of benzaldehyde were produced. The greater the light intensity and the longer reaction time is, the more tendency benzaldehyde reduction would occur. And when the reactor size is larger, photocatalytic acetal reaction is more likely to take place.
our study indicates that photocatalysis is a novel, green and effective method for acetalization of Benzaldehyde and have good prospect in acetal synthesis.
采用溶胶-凝胶法,分别以钛酸四正丁酯[Ti(OC4H9)4]为前驱体,氨水(NH3)为氮源,六水合氯铂酸(H2PtCl6·6H2O)为铂源,在一定条件下制备了纯TiO2、N/TiO2、Pt/TiO2和PtN/TiO2晶体粉末,并通过XRD、XPS、TEM等分析测试手段对其一系列物理特性进行了表征。XRD及TEM测试结果表明：溶胶-凝胶法制备的各种纳米TiO2样品粉末主要为单一锐钛矿晶型的球状颗粒且分布均匀,平均粒径在20nm左右。以紫外光催化降解亚甲基蓝水溶液为模型反应,评价了各种掺杂改性的纳米Ti02和商用Degussa P25的光催化性能,结果表明：各种纳米TiO2粉末对亚甲基蓝均有较好的光催化降解效果,其中混晶型Degussa P25的光催化效率最高。
自行设计了配备光强可调式UV-LED阵列光源的恒温石英玻璃光催化反应系统。在此基础上,采用Degussa P25作为光催化剂,在无水乙醇中研究了苯甲醛光催化合成苯甲醛二乙缩醛(BDA)的反应行为。讨论了氮气是否饱和、反应液pH、紫外光强、反应时间、反应物初始浓度、催化剂用量等因素以及不同类型反应器对苯甲醛二乙缩醛的产率及选择性的影响,优化了反应条件。并考察了甲醇、乙醇、异丙醇等不同醇溶剂对苯甲醛的光催化缩醛反应活性及选择性的影响,发现不同醇溶剂中的缩醛反应速率与醇的pKa值有关,pKa值越小,醇越活泼,反应速率越快。实验结果表明：在反应液pH为7.86,紫外光强为0.6mw/cm2,苯甲醛初始浓度为0.05mol/L, TiO2(P25)催化剂用量为5.0g/L,反应15min条件下,苯甲醛二乙缩醛的产率和选择性最好,GC产率高达99.86%,选择性为100%,且重复性好。
在上述优化条件下,考察了无水乙醇中对位不同取代的苯甲醛光催化缩醛反应行为,讨论了苯环对位取代基的电子效应对缩醛反应活性及选择性的影响。苯环对位为供电子基团(EDG)取代比为吸电子基团取代(EWG)更利于发生缩醛反应,且供电子能力越弱,缩醛产率越高。结合传统缩醛反应机理和非均相光催化反应的特点,探讨了光催化芳香醛缩醛反应机理,与传统质子酸活化羰基不同,芳香醛基在光生电子和空穴的作用下,选择性的生成α-羟基自由基是引发反应的关键步骤。
此外,本文采用自制的光催化微反应器进行苯甲醛与乙醇的光催化反应行为和缩醛反应研究。考察了光强、反应时间及反应器尺寸对微反应器中苯甲醛的光催化缩醛反应影响,结果表明微反应器中不仅发生苯甲醛缩醛反应,更容易发生苯甲醛的还原反应。光强越大、反应时间越长越容易发生苯甲醛还原。而反应器尺寸越大越利于光催化缩醛反应的进行。
纳米Ti02光催化技术为苯甲醛缩醛及其衍生物的合成提供了一种绿色、高效、简便且价廉的合成方法,对缩醛的合成生产具有重要的理论研究意义和一定的实用价值。
Aromatic acetals as a specific kind of fine chemicals has very significant appli-cation value in organic synthesis and industrial production.In this paper, heterogene-ous photocatalytic technology is firstly applied to the acetal reaction in a self-designed constant temperature quartz-glass photocatalytic reactor with UV-LED as light source. Different kinds of TiO2photocatalysis have been prepared and their photocatalysis properties were evaluated.Benzaldehyde Diethyl Acetal (BDA) has been high selec-tively synthesized.the condition of acetal reaction has been optimized. The photocata-lytic acetal reaction of benzaldehyde with different substitutions have also been rese-arched and the mechanism was discussed.
Pure TiO2,N/TiO2,Pt/TiO2and PtN/TiO2were prepared by sol-gel method with tetrabutyltitanate[Ti(OC4H9)4] as a precursor,ammonia(NH3)as nitro source,and six hydration chlorine platinum acid(H2PtCl6·6H2O) as platinuim source respectively.The properties of the various kinds of TiO2were studied by different technologies, such as XRD,XPS and TEM.X-ray diffraction(XRD) and Transmission Electorn Microscope (TEM) showed that the self-synthesized TiO2by sol-gel method mainly are composed with anatase globular particles,and average particle size is less than20nm.The photo-catalytic activities of self-synthesized TiO2and commercial mixed crystal-Degussa P25were evaluated by photo-degradation of methylene blue solution and the result showed that all catalysts demonstrated good capacity of photodagradation,in which mixed crystal-Degussa P25is the best.
We have designed the photocatalytic reaction system equipped with adjustable light intensity UV-LED array light source and constant temperature quartz glass reactor. Based on the system, photocatalytic synthetic reaction behavior of Benzaldehyde Diethyl Acetal(BDA) is studied in anhydrous alcohol with Degussa P25as a catalyst from benzaldehyde. The effects of reaction solution pH, light intensity, reaction time, concentration of substrate, loading of TiO2and dimension of the reactor on reaction rate and yield of BDA were evaluated. Several alcohols such as methanol. ethanol and isopropanol as reactant of the acetal reaction with benzaldehyde were also studied. The yield of BDA could reach high up to100%under the condition of solution pH7.86, TiO2concentration:5.0g/L,benzaldehyde initial concentration:0.05mol/L, light intensity:0.6mw/cm2,temperature:30℃.reaction time:15min. Additionally,the reaction rate was also related to the pKa of the alcohols, the smaller pKa value, the more lively alcohol, the higher the reaction activity.
Furthermore, we investigated the synthesis of aromatic aldehyde with different substitutions under the optimized conditions mentioned above. The results showed that benzaldehyde with EDG substitutions in/P-phenyl ring have good efficiency in the photocatalytic acetal reaction, acetal yield is in the range of83.89%-58.20%,. Chlorine substituted benzaldehyde showed high reaction activity as the lone-electron pair on Chlorine atom give strong electrophobic effect on the phenyl ring, the yield of acetal product reached to96.84%. While acetal reactions of benzaldehyde with EDG substitutions in P-phenyl ring were relatively difficult to take place. The mechanism of the photocatalytic acetal reaction was discussed based on the facts mentioned above.
In addition, benzaldehyde photocatalytic reaction behavior and acetal reaction in ethanol with self-made photocatalytic micro reactors was studied in this paper. The effects of light intensity, reaction time and the size of photocatalytic reactor on benzaldehyde acetal reaction was investigated. The results showed that not only benzaldehyde acetal but reduction of benzaldehyde were produced. The greater the light intensity and the longer reaction time is, the more tendency benzaldehyde reduction would occur. And when the reactor size is larger, photocatalytic acetal reaction is more likely to take place.
our study indicates that photocatalysis is a novel, green and effective method for acetalization of Benzaldehyde and have good prospect in acetal synthesis.
引文
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