羧基化合物及其衍生物促进铂催化硅氢加成反应研究
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摘要
论文总结了近期硅氢加成反应催化剂的制备和应用，分析了硅氢加成反应催化剂在活性和产物选择性以及催化剂的稳定性等方面存有的问题。在此基础上，对应用于烯烃硅氢加成反应的催化剂进行了设计和改进，将含官能基团的羧基化合物及其衍生物作为贵金属铂催化剂的促进剂；在烯烃与含氢硅烷加成反应中，研究了促进剂种类与催化剂性能之间的关系，考察了催化剂体系循环利用的稳定性。
研究发现，含官能基团羧酸可明显提高铂催化烯烃硅氢加成反应活性，并显著影响β-加成产物的选择性。羧酸结构以及所含官能基团类型对苯乙烯硅氢加成反应结果产生重要影响。相对而言，氨基芳香羧酸类作为添加剂具有更好的助催化效果，其中4-氨基苯甲酸效果最佳，用于促进铂催化苯乙烯与三乙氧基硅烷硅氢加成反应，当投料摩尔比例为n(Pt)/n(COOH)=1/100、n(Pt)/n(styrene)=1/4000时，苯乙烯转化率为100％，β-加成产物选择性为98.4％。
使用不同类型的酸酐对一系列不同分子量的聚乙二醇进行改性得到羧基功能化聚乙二醇，将其作为助剂或载体应用到硅氢加成反应中。研究发现，使用酸酐改性的小分子量（平均分子量小于1000）聚乙二醇作为助剂，可有效提高铂催化苯乙烯与三乙氧基硅烷加成反应的转化率和β-加成产物选择性，对于不同烯烃和硅烷都可以取得类似的催化效果。聚乙二醇分子量对铂催化剂的活性和加成产物的选择性产生重要影响，分子量越小，催化剂活性越高；但容易生成诸如烷烃和脱氢偶联等副产物。使用酸酐改性的大分子量（平均分子量大于1000）聚乙二醇作为载体负载络合铂催化剂用于烯烃与烷氧基硅烷加成反应时，也可取得较好的烯烃转化率和β-加成产物选择性。反应结束后，通过离心分离可将催化剂从反应体系中分离，催化剂重复使用8次没有发现催化活性明显变化，表现出较好的催化剂重复使用的稳定性。
此外，还合成了4-氨基苯甲酸改性聚乙二醇稳定的铂纳米颗粒催化剂，通过表征证实了催化剂体系的组成和结构。该催化剂体系应用于烯烃与含氢硅烷加成反应具有很好的催化活性和较高的目标产物选择性。在催化不同烯烃与(EtO)3SiH反应中，均可获得96％以上的选择性，对不同含氢硅烷具有较好的底物适应性。该催化剂具有良好的回收重复使用性能，重复使用9次没有观察到活性明显下降的现象发生。
通过硅烷偶联剂将含羧基化合物接枝到无机载体表面作为载体制备负载络合铂催化剂并对其结构进行了表征。催化剂在催化烯烃与含氢硅烷硅氢加成反应的性能研究表明，通过此方法可以成功地实现对铂的稳定负载，反应温度和催化剂用量对催化反应产生重要影响。催化辛烯与三乙氧基硅烷反应可获得96.7％的β-加成产物（辛烷基三乙氧基硅烷）产率。催化剂具有宽泛的底物适应性，烯烃结构对反应产生重要影响，直链烯烃的链长越长，反应越不容易进行；有对位取代基的芳香烯烃作为底物可以取得更好的β-加成产物选择性；催化剂可以重复使用7次。
The recently progress of the synthesis and application of the catalystfor hydrosilylation has been summarized. Activity of catalyst, selectivityof adducts and the stability of catalyst, the problems existing in thehydrosilylation have also been analyzed. Based on this, carboxylcompound or derivates as promoter for platinum-catalyzedhydrosilylation of alkenes with hydrosilane was investigated. Therelationship between the type of promoters and catalytic performance ofcatalysts has been constructed. Simultaneously, the recycling ability ofcatalyst has also been investigated.
It was found that both the catalytic activity of platinum and theselectivity of β-adduct were increased obviously in the hydrosilylation ofstyrene with (EtO)3SiH by using functional carboxylic acid as promoter.The structure of carboxyl acid and the type of functional group couldinfluence the performance, and carboxyl acid with amino has betterpromoting action. Especially, by using4-aminobenzoic as promoter,100%conversion as well as98.4%selectivity of β-adduct could beobtained under the conditions of n(Pt)/n(COOH)=1/100、 n(Pt)/n(styrene)=1/4000.
A series of carboxyl functionalized polyethylene glycol wassynthesized. These compounds were used as promoter or carrier in theplatinum-catalyzed hydrosilylation of alkenes. It was found that thefunctionalized polyethylene glycol as promoter could increase theconversion of styrene and the selectivity of β-adduct in thehydrosilylation styrene with (EtO)3SiH. The catalyst system is alsosuitable for hydrosilylation of other alkenes. The molecular weight ofpolyethylene glycol can influence the catalytic activity and the selectivityof adduct. Better catalytic activity was attained when using smallermolecular weight PEG, but it is easy to generate byproducts, such asalkane and dehydrogenation etc. Using the functionalized polyethyleneglycol of high molecular weight as carrier supported platinum as catalyst,excellent conversion of the alkenes and the selectivity of β-adduct wereattained in the hydrosilylation of alkenes with silane. The catalyst couldbe easily separated from the reaction system through centrifugation andreuse for8times without obviously decrease of the catalytic performance.
Additionally, the functionalized polyethylene glycol with4-aminobenzoic stabilized platinum nanoparticles catalyst wassynthesized and characterized. The composition and structure of thecatalyst has been confirmed through NMR, UV, IR and TEM. Thecatalyst show excellent catalytic activity and selectivity of adduct in the hydrosilylation of alkenes with silane. The selectivity of β-adduct are allabove of96%in hydrosilylation of various alkenes with (EtO)3SiH. Thecatalyst is also suitable for the different hydrosilane. Furthermore, thecatalyst could be recyclable for9times without obviously decrease ofcatalytic activity.
At last, the functionalized silica with γ-aminopropyltriethoxylsilaneand undecylenic acid supported platinum catalyst was prepared andapplied in the hydrosilylation of alkenes with silane. The results indicatethat the reaction temperature and the amount of catalyst influence thereaction. The yield of octanyltriethoxylsilane reaches96.7%in thehydrosilylation of1-octene with triethoxylsilane. The structure of olefinsinfluences on the hydrosilylation. Better the selectivity of β-adduct can beattained in the hydrosilylation of aromatic olefins with para-orientatinggroup. The catalyst could be reused7times.
研究发现，含官能基团羧酸可明显提高铂催化烯烃硅氢加成反应活性，并显著影响β-加成产物的选择性。羧酸结构以及所含官能基团类型对苯乙烯硅氢加成反应结果产生重要影响。相对而言，氨基芳香羧酸类作为添加剂具有更好的助催化效果，其中4-氨基苯甲酸效果最佳，用于促进铂催化苯乙烯与三乙氧基硅烷硅氢加成反应，当投料摩尔比例为n(Pt)/n(COOH)=1/100、n(Pt)/n(styrene)=1/4000时，苯乙烯转化率为100％，β-加成产物选择性为98.4％。
使用不同类型的酸酐对一系列不同分子量的聚乙二醇进行改性得到羧基功能化聚乙二醇，将其作为助剂或载体应用到硅氢加成反应中。研究发现，使用酸酐改性的小分子量（平均分子量小于1000）聚乙二醇作为助剂，可有效提高铂催化苯乙烯与三乙氧基硅烷加成反应的转化率和β-加成产物选择性，对于不同烯烃和硅烷都可以取得类似的催化效果。聚乙二醇分子量对铂催化剂的活性和加成产物的选择性产生重要影响，分子量越小，催化剂活性越高；但容易生成诸如烷烃和脱氢偶联等副产物。使用酸酐改性的大分子量（平均分子量大于1000）聚乙二醇作为载体负载络合铂催化剂用于烯烃与烷氧基硅烷加成反应时，也可取得较好的烯烃转化率和β-加成产物选择性。反应结束后，通过离心分离可将催化剂从反应体系中分离，催化剂重复使用8次没有发现催化活性明显变化，表现出较好的催化剂重复使用的稳定性。
此外，还合成了4-氨基苯甲酸改性聚乙二醇稳定的铂纳米颗粒催化剂，通过表征证实了催化剂体系的组成和结构。该催化剂体系应用于烯烃与含氢硅烷加成反应具有很好的催化活性和较高的目标产物选择性。在催化不同烯烃与(EtO)3SiH反应中，均可获得96％以上的选择性，对不同含氢硅烷具有较好的底物适应性。该催化剂具有良好的回收重复使用性能，重复使用9次没有观察到活性明显下降的现象发生。
通过硅烷偶联剂将含羧基化合物接枝到无机载体表面作为载体制备负载络合铂催化剂并对其结构进行了表征。催化剂在催化烯烃与含氢硅烷硅氢加成反应的性能研究表明，通过此方法可以成功地实现对铂的稳定负载，反应温度和催化剂用量对催化反应产生重要影响。催化辛烯与三乙氧基硅烷反应可获得96.7％的β-加成产物（辛烷基三乙氧基硅烷）产率。催化剂具有宽泛的底物适应性，烯烃结构对反应产生重要影响，直链烯烃的链长越长，反应越不容易进行；有对位取代基的芳香烯烃作为底物可以取得更好的β-加成产物选择性；催化剂可以重复使用7次。
The recently progress of the synthesis and application of the catalystfor hydrosilylation has been summarized. Activity of catalyst, selectivityof adducts and the stability of catalyst, the problems existing in thehydrosilylation have also been analyzed. Based on this, carboxylcompound or derivates as promoter for platinum-catalyzedhydrosilylation of alkenes with hydrosilane was investigated. Therelationship between the type of promoters and catalytic performance ofcatalysts has been constructed. Simultaneously, the recycling ability ofcatalyst has also been investigated.
It was found that both the catalytic activity of platinum and theselectivity of β-adduct were increased obviously in the hydrosilylation ofstyrene with (EtO)3SiH by using functional carboxylic acid as promoter.The structure of carboxyl acid and the type of functional group couldinfluence the performance, and carboxyl acid with amino has betterpromoting action. Especially, by using4-aminobenzoic as promoter,100%conversion as well as98.4%selectivity of β-adduct could beobtained under the conditions of n(Pt)/n(COOH)=1/100、 n(Pt)/n(styrene)=1/4000.
A series of carboxyl functionalized polyethylene glycol wassynthesized. These compounds were used as promoter or carrier in theplatinum-catalyzed hydrosilylation of alkenes. It was found that thefunctionalized polyethylene glycol as promoter could increase theconversion of styrene and the selectivity of β-adduct in thehydrosilylation styrene with (EtO)3SiH. The catalyst system is alsosuitable for hydrosilylation of other alkenes. The molecular weight ofpolyethylene glycol can influence the catalytic activity and the selectivityof adduct. Better catalytic activity was attained when using smallermolecular weight PEG, but it is easy to generate byproducts, such asalkane and dehydrogenation etc. Using the functionalized polyethyleneglycol of high molecular weight as carrier supported platinum as catalyst,excellent conversion of the alkenes and the selectivity of β-adduct wereattained in the hydrosilylation of alkenes with silane. The catalyst couldbe easily separated from the reaction system through centrifugation andreuse for8times without obviously decrease of the catalytic performance.
Additionally, the functionalized polyethylene glycol with4-aminobenzoic stabilized platinum nanoparticles catalyst wassynthesized and characterized. The composition and structure of thecatalyst has been confirmed through NMR, UV, IR and TEM. Thecatalyst show excellent catalytic activity and selectivity of adduct in the hydrosilylation of alkenes with silane. The selectivity of β-adduct are allabove of96%in hydrosilylation of various alkenes with (EtO)3SiH. Thecatalyst is also suitable for the different hydrosilane. Furthermore, thecatalyst could be recyclable for9times without obviously decrease ofcatalytic activity.
At last, the functionalized silica with γ-aminopropyltriethoxylsilaneand undecylenic acid supported platinum catalyst was prepared andapplied in the hydrosilylation of alkenes with silane. The results indicatethat the reaction temperature and the amount of catalyst influence thereaction. The yield of octanyltriethoxylsilane reaches96.7%in thehydrosilylation of1-octene with triethoxylsilane. The structure of olefinsinfluences on the hydrosilylation. Better the selectivity of β-adduct can beattained in the hydrosilylation of aromatic olefins with para-orientatinggroup. The catalyst could be reused7times.
引文
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