超分子催化合成天然苯甲醛的绿色化研究
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摘要
苯甲醛是世界第二大主要香料,仅次于香兰素,广泛用于食品、饮料、医药、化妆品等领域。随着人们对食品安全问题的不断深化,天然苯甲醛日益受到消费者的青睐且代表着良好的市场价值,因此天然苯甲醛的生产受到广泛的关注。本文立足于我国资源丰富的肉桂油(主要成分为肉桂醛),旨在建立一种清洁有效、反应条件温和的由天然肉桂油制备天然苯甲醛的方法,使用多种绿色技术,包括使用超分子金属卟啉、环糊精等绿色催化剂,以分子氧或双氧水等为绿色氧化剂,以水为绿色溶剂等技术来实现天然苯甲醛的高效的清洁液相合成。并通过实验、各种测试手段、原位表征、量子化学ab initio计算模拟及动力学等方法进行反应的机理研究。
本文首先研究了金属卟啉超分子催化分子氧氧化肉桂醛制备苯甲醛。该方法中,四苯基锰卟啉(MnTPPCl)仅以ppm级的用量就可以高效催化肉桂醛氧化,显示出很高的催化活性和选择性,苯甲醛的收率达71%。这是因为锰具有可变的价态和合适的还原电势,容易生成活性中间体金属高价氧代物的缘故。
本文重点研究了β-环糊精(β-CD)及其衍生物催化肉桂醛制备苯甲醛。因为水是一种便宜的清洁的溶剂,有益于生态环境和食品安全;而且,水相有机反应是绿色化学的一个重要研究方向。
在β-CD催化肉桂醛碱性水解制备苯甲醛体系中,通过FT-IR、~1H NMR、ROESY、UV-Vis以及Gaussian 03分子模拟对β-CD/肉桂醛包结物进行分析表征,确定肉桂醛与β-CD形成了摩尔比为1:1的包结物,包结常数为329M-1(298K),且肉桂醛的醛基与β-CD的仲羟基之间存在氢键。氢键促进了氧负离子(O-)的生成以及外来的氢氧根离子(OH-)对肉桂醛的亲核进攻,从而促进了肉桂醛的逆羟醛缩合反应。然而,乙醛和肉桂醛的羰基都具有α-H,可以发生羟醛缩合反应,且苯甲醛自身也容易发生聚合反应和歧化反应,从而降低了苯甲醛的收率,仅为42%。动力学研究表明,β-CD的参与使肉桂醛碱性水解的反应活化能由空白实验的57.11kJ/mol降到了45.27 kJ/mol,从而加速了反应的进行。从活化能的角度解释β-CD的催化作用,是本文最大的创新。
在β-CD的水溶性衍生物——2-羟丙基-β-环糊精(2-HP-β-CD)催化肉桂醛碱性水解制备苯甲醛的体系中,通过联合使用DSC、~1H NMR、ROESY以及荧光光谱等各种分析手段,确定肉桂醛与2-HP-β-CD形成了摩尔比为1:1的包结物,包结常数为928M-1(298K),且肉桂醛与2-HP-β-CD之间存在着强烈的氢键;进一步的动力学研究和增溶性研究表明主客体分子间相互作用力的方式和强度与主体对客体的增溶性、客体的活化有着直接的因果关系,也就是说环糊精超分子作为催化剂,是通过与底物形成包结物来活化底物,提高反应选择性的,而这种催化能力的大小,主要依赖于主客体之间包结能力的大小。因此,2-HP-β-CD是更有效的催化剂,显著地提高了肉桂醛碱性水解制备苯甲醛的反应选择性,苯甲醛收率达70%。
在β-CD催化次氯酸钠或者双氧水氧化肉桂醛制备苯甲醛的体系中,苯甲醛的收率前者可达到76%,后者可达78%。显然,双氧水是更合适的氧化剂,也是更清洁的氧化剂。并以天然肉桂油(含93%肉桂醛)为原料,对β-CD/H_2O_2-NaHCO_3氧化体系进行了放大反应,苯甲醛的收率达67%。借助in situ FT-IR、GC-MS等测试手段,通过设计实验,认为β-CD与肉桂醛首先形成包结物,H_2O_2与HCO_3~-形成过氧酸根离子HCO_4~-,HCO_4~-对被包结的肉桂醛显示出强烈的亲核氧化性,并且肉桂醛与β-CD之间的氢键也促进了HCO_4~-对肉桂醛的亲核氧化,先生成大量的环氧化产物和少量的苯甲醛,环氧化产物可进一步氧化为苯甲醛。
放大实验的成功,表明肉桂油/β-CD/H_2O_2-NaHCO_3体系在温和的反应条件(常压,60℃)下实现了天然苯甲醛的高效的清洁水相合成,此体系兼有环境友好和良好的经济性,具有潜在的工业应用价值,同时为芳香醛类香料的合成提供理论基础和技术基础,为应用于食品等领域的其他有机中间体的生产提供一条环境友好的途径。
In total amount of spice in the world, benzaldehyde is the second largest perfume after vanillin. With more cares about food quality from consumers, natural benzaldehyde is more and more popular and represents a strong market advantage. As a result, the synthesis of natural benzaldehyde is drawing much attention. Based on the rich natural cinnamal oil, of which cinnamaldehyde is the main composition, we have developed a clean and efficient process to produce benzaldehyde from cinnamaldehyde under much milder conditions, using various green technologies including green oxidant, green solvent and green catalyst. Moreover, the mechanism has been investigated by experiments, various characteristic methods, in-situ characterization, ab initio computational methods and kinetics methods.
In this paper, oxidative cleavage of cinnamaldehyde to benzaldehyde catalyzed by metalloporphyrins in the presence of dioxygen had been investigated at first. MnTPPCl showed excellent activity for the oxidation at the ppm level and 71% yield of benzaldehyde was obtained at 60℃and ambient atmosphere. It was attributed to manganese having variable valence and appropriate reduction potential to facilitate formation of high valent metal-oxo ligand, which was verified by UV-vis spectroscopy.
Then, this paper focused on the conversion of cinnamaldehyde to benzaldehyde catalyzed byβ-cyclodextrin (β-CD) or its derivatives. It is because water is good for environment and food safety as a cheap and clean solvent. Moreover, organic reactions in aqueous solution have been one of roles of green chemistry.
Inβ-CD catalytic alkaline hydrolysis system, various analysis methods, e.g., FT-IR, UV-Vis, ~1H NMR, ROESY and Gaussian 03 had been utilized to demonstrate the formation of 1:1 (molar ratio) complexes betweenβ-CD and cinnamaldehyde and the inclusion equilibrium constant was 329 M~(-1) at 298K. Furthermore, the aldehyde group forms hydrogen bond with the secondary alcohol ofβ-CD. It is the hydrogen bond that facilitates formation of the oxygen anion (O-) and the nucleophilic addition of external hydroxide ion with cinnamaldehyde, which results into the acceleration ofβ-CD over alkaline hydrolysis of cinnamaldehyde. However, both acetaldehyde and cinnamaldehyde ownα- proton to the carbonyl group, the crossed Aldol condensation reaction also took place. In addition, benzaldehyde was prone to its own disproportionation and polymerization reactions. As a result, the yield of benzaldehyde decreased to be only 42% at 50℃and ambient atmosphere. From the results of kinetic analysis, it could be found that the activation energy for the hydrolysis of cinnamaldehyde to benzaldehyde decreased from 57.11 kJ/mol in the absence ofβ-CD to 45.27 kJ/mol in the presence ofβ-CD. It is the first time to clarity whyβ-CD can promote the reaction from the perspective of the activation energy.
In 2-hydroxypropyl-β-cyclodextrin (2-HPβ-CD) catalytic alkaline hydrolysis system, the combination of DSC, FT-IR, UV-Vis, 1H NMR, ROESY and fluorescence measurements was used to verify the formation ofβ-CD/cinnamaldehyde inclusion complex with molar ratio of 1:1 and the inclusion equilibrium constant was 928 M~(-1) at 298K. Moreover, the aldehyde group forms strong hydrogen bond with 2-HPβ-CD. The further investigation on kinetic studies and solubilization indicated that weak molecular interactions between guest and the CDs had a direct relevance on their solubilization efficiency, and the binding abilities among CDs and substrate mainly affected the hydrolysis reactivity. Then, 2-HPβ-CD conferred high activity and selectivity for the alkaline hydrolysis of cinnamaldehyde and the yield of benzaldehyde was 70% at 50℃and ambient atmosphere.
Inβ-CD/NaClO orβ-CD/H2O2 oxidation system, at 60℃and ambient atmosphere, the yield of benzaldehyde was 76% in the presence of NaClO and was 78% in the presence of H2O2. Obviously, H_2O_2 is a cleaner and more appropriate oxidant than NaClO. A large-scale experiment for the conversion of natural cinnamal oil ( 93% cinnamaldehyde ) to benzaldehyde in H_2O_2 -NaHCO_3 oxidation system was carried out and the yield of benzaldehyde was 67%. Peroxymonocarbonate ion (HCO_4~-) was easily formed by H_2O_2 with HCO_3~-, which shows a strong nucleophilic oxidation toward the included cinnamaldehyde. Furthermore, the non-covalent intermolecular interactions betweenβ-CD and cinnamaldehyde promoted the nucleophilic oxidation. Therefore, trace amount of benzaldehyde and large amount of the corresponding epoxide were obtained. The epoxide was further oxidized to benzaldehyde by HCO_4~-. These processes were verified by in situ FTIR spectra, theoretical method and GC-MS.
The success of amplification experiment indicated that theβ-CD/H_2O_2 -NaHCO_3 oxidation system achieved a clean and efficient process for producing natural benzaldehyde from natural cinnamal oil in water at 60℃and ambient atmosphere, which has both environmentally-friendly and good economy. The benign, mild and straightforward methodology for the conversion of cinnamaldehyde to benzaldehyde may find its potential application in industrial operation and offer theoretical and technical foundation and a general method for the clean synthesis of other similar natural aromatic fragrant compounds.
本文首先研究了金属卟啉超分子催化分子氧氧化肉桂醛制备苯甲醛。该方法中,四苯基锰卟啉(MnTPPCl)仅以ppm级的用量就可以高效催化肉桂醛氧化,显示出很高的催化活性和选择性,苯甲醛的收率达71%。这是因为锰具有可变的价态和合适的还原电势,容易生成活性中间体金属高价氧代物的缘故。
本文重点研究了β-环糊精(β-CD)及其衍生物催化肉桂醛制备苯甲醛。因为水是一种便宜的清洁的溶剂,有益于生态环境和食品安全;而且,水相有机反应是绿色化学的一个重要研究方向。
在β-CD催化肉桂醛碱性水解制备苯甲醛体系中,通过FT-IR、~1H NMR、ROESY、UV-Vis以及Gaussian 03分子模拟对β-CD/肉桂醛包结物进行分析表征,确定肉桂醛与β-CD形成了摩尔比为1:1的包结物,包结常数为329M-1(298K),且肉桂醛的醛基与β-CD的仲羟基之间存在氢键。氢键促进了氧负离子(O-)的生成以及外来的氢氧根离子(OH-)对肉桂醛的亲核进攻,从而促进了肉桂醛的逆羟醛缩合反应。然而,乙醛和肉桂醛的羰基都具有α-H,可以发生羟醛缩合反应,且苯甲醛自身也容易发生聚合反应和歧化反应,从而降低了苯甲醛的收率,仅为42%。动力学研究表明,β-CD的参与使肉桂醛碱性水解的反应活化能由空白实验的57.11kJ/mol降到了45.27 kJ/mol,从而加速了反应的进行。从活化能的角度解释β-CD的催化作用,是本文最大的创新。
在β-CD的水溶性衍生物——2-羟丙基-β-环糊精(2-HP-β-CD)催化肉桂醛碱性水解制备苯甲醛的体系中,通过联合使用DSC、~1H NMR、ROESY以及荧光光谱等各种分析手段,确定肉桂醛与2-HP-β-CD形成了摩尔比为1:1的包结物,包结常数为928M-1(298K),且肉桂醛与2-HP-β-CD之间存在着强烈的氢键;进一步的动力学研究和增溶性研究表明主客体分子间相互作用力的方式和强度与主体对客体的增溶性、客体的活化有着直接的因果关系,也就是说环糊精超分子作为催化剂,是通过与底物形成包结物来活化底物,提高反应选择性的,而这种催化能力的大小,主要依赖于主客体之间包结能力的大小。因此,2-HP-β-CD是更有效的催化剂,显著地提高了肉桂醛碱性水解制备苯甲醛的反应选择性,苯甲醛收率达70%。
在β-CD催化次氯酸钠或者双氧水氧化肉桂醛制备苯甲醛的体系中,苯甲醛的收率前者可达到76%,后者可达78%。显然,双氧水是更合适的氧化剂,也是更清洁的氧化剂。并以天然肉桂油(含93%肉桂醛)为原料,对β-CD/H_2O_2-NaHCO_3氧化体系进行了放大反应,苯甲醛的收率达67%。借助in situ FT-IR、GC-MS等测试手段,通过设计实验,认为β-CD与肉桂醛首先形成包结物,H_2O_2与HCO_3~-形成过氧酸根离子HCO_4~-,HCO_4~-对被包结的肉桂醛显示出强烈的亲核氧化性,并且肉桂醛与β-CD之间的氢键也促进了HCO_4~-对肉桂醛的亲核氧化,先生成大量的环氧化产物和少量的苯甲醛,环氧化产物可进一步氧化为苯甲醛。
放大实验的成功,表明肉桂油/β-CD/H_2O_2-NaHCO_3体系在温和的反应条件(常压,60℃)下实现了天然苯甲醛的高效的清洁水相合成,此体系兼有环境友好和良好的经济性,具有潜在的工业应用价值,同时为芳香醛类香料的合成提供理论基础和技术基础,为应用于食品等领域的其他有机中间体的生产提供一条环境友好的途径。
In total amount of spice in the world, benzaldehyde is the second largest perfume after vanillin. With more cares about food quality from consumers, natural benzaldehyde is more and more popular and represents a strong market advantage. As a result, the synthesis of natural benzaldehyde is drawing much attention. Based on the rich natural cinnamal oil, of which cinnamaldehyde is the main composition, we have developed a clean and efficient process to produce benzaldehyde from cinnamaldehyde under much milder conditions, using various green technologies including green oxidant, green solvent and green catalyst. Moreover, the mechanism has been investigated by experiments, various characteristic methods, in-situ characterization, ab initio computational methods and kinetics methods.
In this paper, oxidative cleavage of cinnamaldehyde to benzaldehyde catalyzed by metalloporphyrins in the presence of dioxygen had been investigated at first. MnTPPCl showed excellent activity for the oxidation at the ppm level and 71% yield of benzaldehyde was obtained at 60℃and ambient atmosphere. It was attributed to manganese having variable valence and appropriate reduction potential to facilitate formation of high valent metal-oxo ligand, which was verified by UV-vis spectroscopy.
Then, this paper focused on the conversion of cinnamaldehyde to benzaldehyde catalyzed byβ-cyclodextrin (β-CD) or its derivatives. It is because water is good for environment and food safety as a cheap and clean solvent. Moreover, organic reactions in aqueous solution have been one of roles of green chemistry.
Inβ-CD catalytic alkaline hydrolysis system, various analysis methods, e.g., FT-IR, UV-Vis, ~1H NMR, ROESY and Gaussian 03 had been utilized to demonstrate the formation of 1:1 (molar ratio) complexes betweenβ-CD and cinnamaldehyde and the inclusion equilibrium constant was 329 M~(-1) at 298K. Furthermore, the aldehyde group forms hydrogen bond with the secondary alcohol ofβ-CD. It is the hydrogen bond that facilitates formation of the oxygen anion (O-) and the nucleophilic addition of external hydroxide ion with cinnamaldehyde, which results into the acceleration ofβ-CD over alkaline hydrolysis of cinnamaldehyde. However, both acetaldehyde and cinnamaldehyde ownα- proton to the carbonyl group, the crossed Aldol condensation reaction also took place. In addition, benzaldehyde was prone to its own disproportionation and polymerization reactions. As a result, the yield of benzaldehyde decreased to be only 42% at 50℃and ambient atmosphere. From the results of kinetic analysis, it could be found that the activation energy for the hydrolysis of cinnamaldehyde to benzaldehyde decreased from 57.11 kJ/mol in the absence ofβ-CD to 45.27 kJ/mol in the presence ofβ-CD. It is the first time to clarity whyβ-CD can promote the reaction from the perspective of the activation energy.
In 2-hydroxypropyl-β-cyclodextrin (2-HPβ-CD) catalytic alkaline hydrolysis system, the combination of DSC, FT-IR, UV-Vis, 1H NMR, ROESY and fluorescence measurements was used to verify the formation ofβ-CD/cinnamaldehyde inclusion complex with molar ratio of 1:1 and the inclusion equilibrium constant was 928 M~(-1) at 298K. Moreover, the aldehyde group forms strong hydrogen bond with 2-HPβ-CD. The further investigation on kinetic studies and solubilization indicated that weak molecular interactions between guest and the CDs had a direct relevance on their solubilization efficiency, and the binding abilities among CDs and substrate mainly affected the hydrolysis reactivity. Then, 2-HPβ-CD conferred high activity and selectivity for the alkaline hydrolysis of cinnamaldehyde and the yield of benzaldehyde was 70% at 50℃and ambient atmosphere.
Inβ-CD/NaClO orβ-CD/H2O2 oxidation system, at 60℃and ambient atmosphere, the yield of benzaldehyde was 76% in the presence of NaClO and was 78% in the presence of H2O2. Obviously, H_2O_2 is a cleaner and more appropriate oxidant than NaClO. A large-scale experiment for the conversion of natural cinnamal oil ( 93% cinnamaldehyde ) to benzaldehyde in H_2O_2 -NaHCO_3 oxidation system was carried out and the yield of benzaldehyde was 67%. Peroxymonocarbonate ion (HCO_4~-) was easily formed by H_2O_2 with HCO_3~-, which shows a strong nucleophilic oxidation toward the included cinnamaldehyde. Furthermore, the non-covalent intermolecular interactions betweenβ-CD and cinnamaldehyde promoted the nucleophilic oxidation. Therefore, trace amount of benzaldehyde and large amount of the corresponding epoxide were obtained. The epoxide was further oxidized to benzaldehyde by HCO_4~-. These processes were verified by in situ FTIR spectra, theoretical method and GC-MS.
The success of amplification experiment indicated that theβ-CD/H_2O_2 -NaHCO_3 oxidation system achieved a clean and efficient process for producing natural benzaldehyde from natural cinnamal oil in water at 60℃and ambient atmosphere, which has both environmentally-friendly and good economy. The benign, mild and straightforward methodology for the conversion of cinnamaldehyde to benzaldehyde may find its potential application in industrial operation and offer theoretical and technical foundation and a general method for the clean synthesis of other similar natural aromatic fragrant compounds.
引文
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