生物质基糠醛和乙酰丙酸制备化学品和含氧燃料的研究
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摘要
生物质资源是一种碳中性的可再生资源。由于生物质资源是唯一可以转化为常规的液态、固态和气态燃料和其他化学品的可再生资源,因此生物质资源在替代化石资源的过程中具有独特的优势。通过生物炼制的过程,可以将生物质转化为大宗的低附加值的产品,如液态燃料和小宗的高附加值化学品,如琥珀酸,山梨糖醇和甘油。生物质基平台分子是生物炼制过程中重要的桥梁,链接了生物质原料和目标产品,如燃料、燃料添加剂和化学品。提高生物质资源对化石资源竞争力,发展简单低成本的平台分子制备工艺和高效转化平台分子到燃料和化学品的新方法是重要的手段。
糠醛和乙酰丙酸是生物质转化过程中两种重要的平台分子。糠醛可以大规模的从木质纤维素生物质中半纤维素获得。目前,工业上应用无机酸催化剂实现了糠醛的规模化生产。但是,传统无机酸催化剂存在设备腐蚀和环境污染等问题,为了解决上述问题,我们发展了一种基于氢氧化钽的固体酸催化剂TA-p,实现了催化D-木糖到糠醛的高效转化。在木糖转化糠醛工作的基础上,我们建立了一条由糠醛经多步催化转化到聚呋喃二甲酸丁二醇酯(PBF)的新路线,首次实现了糠醛到呋喃二甲酸类聚酯的转化。
乙酰丙酸可以低成本高收率的从木质纤维素生物质通过酸水解过程获得,从乙酰丙酸出发可以制备一系列的具备作为燃料添加剂应用潜力的衍生物。其中,戊酸酯类生物燃料由于其合适的燃料性质被认为是一种新型的含氧燃料。目前戊酸酯的制备取得了一系列进展,但是尚缺乏对乙酰丙酸一步高效转化戊酸酯过程的研究。我们发展了一种双功能催化剂Ru/SBA-SO3H实现了催化乙酰丙酸一步高效转化戊酸酯类含氧燃料。
第1章围绕生物质资源和生物炼制两个方面,简要综述了生物质转化利用的几种途径和生物质基平台分子。在此基础上,详细介绍了糠醛和乙酰丙酸两种生物质平台分子的制备和转化的研究进展。
第2章介绍了固体酸催化剂TA-p在水-有机溶剂双相体系中选择性催化D-木糖转化到糠醛的研究。系统研究了间歇式反应器和固定床反应器中的转化过程。研究发现间歇法过程中反应温度、有机溶剂的种类和反应时间对D-木糖的转化率和糠醛收率有明显的影响,反应体系中氯离子的加入会部分降低催化剂TA-p的催化效果。在水-1-丁醇的双相体系的连续固定床反应器中,最优条件下TA-p催化D-木糖转化率为96%,获得糠醛最高收率为59%。固定床反应器中连续运行80h,D-木糖的转化率和糠醛收率几乎保持不变,显示出TA-p催化剂高的催化活性和优秀的稳定性。
第3章主要研究了由糠醛经多步催化转化到2,5-呋喃二甲酸聚酯的新路线,合成了聚呋喃二甲酸丁二醇酯(PBF)并对聚酯的结构和热力学性质进行了表征。由糠醛经糠酸两步转化生物质基重要平台分子、呋喃二甲酸聚酯单体2,5-FDCA的过程选择性超过了80%。PBF的单体2,5-呋喃二甲酸和1,4-丁二醇完全由糠醛转化得到,实现了糠醛到PBF的全碳转化。这一新的路径不仅可以有效避免5-羟甲基糠醛的短缺对下游衍生物发展造成的阻碍作用,促进2,5-呋喃二甲酸聚酯的工业化进程,而且进一步扩大了糠醛工业化应用的潜力。
第4章主要围绕乙酰丙酸,研究了乙酰丙酸—步高效转化戊酸酯类含氧燃料的过程。研究发现合适的催化剂酸强度和适当的加氢活性是反应的关键因素。制备了一种双功能催化剂Ru/SBA-SO3H,戊酸乙酯和戊酸的选择性随着催化剂Ru/SBA-SO3H酸量的增加而升高,最高选择性达到94%(100%乙酰丙酸转化率)。通过对反应动力学的研究提出了可能的反应途径,并通过实验进行了验证。
最后,对全文进行了总结和展望。
综上所述,本文紧密围绕生物质转化中两种重要的平台分子糠醛和乙酰丙酸,借助非均相催化的手段,实现了木糖到糠醛的高效转化,发展了糠醛转化呋喃类高分子聚酯的新路线,完成了乙酰丙酸到戊酸酯类含氧燃料的一步高效加氢转化。
Biomass resource is a carbon-neutral renewable resource. Because biomass resource is the only one which can be converted into conventional liquid, solid and gaseous fuels and other chemicals among the renewable resources, it has a unique advantage in the process of substitution of fossil resources. Biomass can be converted into the bulk but low value-added products, such as liquid fuels and high value-added chemicals such as succinic acid, sorbitol and glycerin through bio-refinery process. Biomass-based platform molecules are important bridges which linked the biomass feedstocks and target products such as fuels, fuel additives and chemicals. The development of simple and inexpensive process for the preparation of platform molecules and efficient conversion of platform molecules into fuels and chemicals are significant to improve the competitiveness of biomass resources to fossil resources.
Furfural and levulinic acid are two important platform molecules in the biomass conversion process. Furfural can be obtained from the hemicellulose in the lignocellulosic biomass. At present, the catalysts in large-scale industrial production of furfural are inorganic acids. However, there are some problems of traditional inorganic acid catalysts, such as equipment corrosion and environmental pollution. In order to solve the above problems, we developed a tantalum hydroxide-based solid acid catalyst TA-p to catalytic convert D-xylose to furfural. On the basis of the conversion of D-xylose to furfural, we have established a multi-step catalytic conversion of furfural into poly(butylene2,5-furandicarboxylate)(PBF) for the first time.
Levulinic acid could be cost-effectively produced from lignocellulosic materials via acid hydrolysis process in high yields. Additionally, the LA derivatives which feature with proper combustion properties and energy density have the potential to serve as fuel additives. Among them, valerate esters as novel oxygenated fuels could be blended in both gasoline and diesel. Currently the preparation of valerate esters has been reported, but there is still lack of the research on the efficient conversion of levulinic acid into valerate esters in one step. We have developed a bifunctional catalyst Ru/SBA-SO3H to achieve efficient catalytic one-step conversion of levulinic acid into valerate esters as oxygenated fuels.
Chapter1presetned the concepts of biomass resources and biorefineries, then a brief overview of the use of biomass in several ways and biomass-based platform molecules was introduced. We reviewed of the preparation of furfural and the transformation of furfural and levulinic acid.
Chapter2described the solid acid catalyst TA-p in water-organic solvent biphasic system for selective catalytic conversion of D-xylose to furfural. This process was performed both in a batch reactor and a continuous fixed-bed reactor. In the batch process, D-xylose conversion and furfural yield were significantly affected by the organic solvents, reaction temperature and time.1-butanol, which could be obtained through the fermentation of biomass-based carbohydrates, was selected as organic phase and the highest furfural yield of59%was achieved with D-xylose conversion of96%at180℃in the continuous process. Moreover, the long-time stability test for80h under the optimal conditions showed excellent stability of TA-p.
Chapter3studied a multi-step route of catalytic conversion of furfural into2,5-furandicarboxylic acid-based polyester PBF with total carbon utilization. Catalytic oxidation of furfural into furoate could be easily achieved with a selectivity of93%at100%furfural conversion. The best results of catalytic disproportionation of furoate to furan and2,5-furandicarboxylate were obtained with the selectivity to2,5-FDCA of86%at61%furoate conversion. We have presented a new pathway of converting furfural which was a bulk biomass-based chemical into the key monomer2,5-FDCA of2,5-furandicarboxylic acid-based polyester with a good overall selectivity (80%for the two-step process). This route provides a hitherto important yet neglected strategy linking the platform molecule furfural from C5sugars and2,5-FDCA from C6sugars. It opens a new pathway for biorefinery and further study of the process is necessary. Moreover, furan was converted into1,4-BDO with the highest selectivity of70%at99%furan conversion. The furan-based polyester PBF was prepared from2,5-FDCA and1,4-BDO with total carbon utilization of furfural.
Chapter4mainly discussed the hydrogenation of levulinic acid to valerate esters over supported Ru catalysts. The suitable acidity and proper hydrogenation activity of catalyst were the key factors for the reaction. A bifunctional catalyst Ru/SBA-SO3H was developed as active catalyst and characterized. The increase in the amount of acid sites on the support improved the selectivity to EV and VA, and the highest yield of94%to EV and VA was achieved. Probable reaction pathways were proposed and verified.
Finally, we summaried the full paper and outlook the future work.
In summary, this paper focused on two important platform molecules of furfural and levulinic acid in biomass conversion. The efficient conversion of D-xylose to furfural, a new route of conversion of furfural into2,5-furandicarboxylic acid-based polyester and the hydrogenation of levulinic acid to valerate esters in one-step with heterogeneous catalysis were achieved.
糠醛和乙酰丙酸是生物质转化过程中两种重要的平台分子。糠醛可以大规模的从木质纤维素生物质中半纤维素获得。目前,工业上应用无机酸催化剂实现了糠醛的规模化生产。但是,传统无机酸催化剂存在设备腐蚀和环境污染等问题,为了解决上述问题,我们发展了一种基于氢氧化钽的固体酸催化剂TA-p,实现了催化D-木糖到糠醛的高效转化。在木糖转化糠醛工作的基础上,我们建立了一条由糠醛经多步催化转化到聚呋喃二甲酸丁二醇酯(PBF)的新路线,首次实现了糠醛到呋喃二甲酸类聚酯的转化。
乙酰丙酸可以低成本高收率的从木质纤维素生物质通过酸水解过程获得,从乙酰丙酸出发可以制备一系列的具备作为燃料添加剂应用潜力的衍生物。其中,戊酸酯类生物燃料由于其合适的燃料性质被认为是一种新型的含氧燃料。目前戊酸酯的制备取得了一系列进展,但是尚缺乏对乙酰丙酸一步高效转化戊酸酯过程的研究。我们发展了一种双功能催化剂Ru/SBA-SO3H实现了催化乙酰丙酸一步高效转化戊酸酯类含氧燃料。
第1章围绕生物质资源和生物炼制两个方面,简要综述了生物质转化利用的几种途径和生物质基平台分子。在此基础上,详细介绍了糠醛和乙酰丙酸两种生物质平台分子的制备和转化的研究进展。
第2章介绍了固体酸催化剂TA-p在水-有机溶剂双相体系中选择性催化D-木糖转化到糠醛的研究。系统研究了间歇式反应器和固定床反应器中的转化过程。研究发现间歇法过程中反应温度、有机溶剂的种类和反应时间对D-木糖的转化率和糠醛收率有明显的影响,反应体系中氯离子的加入会部分降低催化剂TA-p的催化效果。在水-1-丁醇的双相体系的连续固定床反应器中,最优条件下TA-p催化D-木糖转化率为96%,获得糠醛最高收率为59%。固定床反应器中连续运行80h,D-木糖的转化率和糠醛收率几乎保持不变,显示出TA-p催化剂高的催化活性和优秀的稳定性。
第3章主要研究了由糠醛经多步催化转化到2,5-呋喃二甲酸聚酯的新路线,合成了聚呋喃二甲酸丁二醇酯(PBF)并对聚酯的结构和热力学性质进行了表征。由糠醛经糠酸两步转化生物质基重要平台分子、呋喃二甲酸聚酯单体2,5-FDCA的过程选择性超过了80%。PBF的单体2,5-呋喃二甲酸和1,4-丁二醇完全由糠醛转化得到,实现了糠醛到PBF的全碳转化。这一新的路径不仅可以有效避免5-羟甲基糠醛的短缺对下游衍生物发展造成的阻碍作用,促进2,5-呋喃二甲酸聚酯的工业化进程,而且进一步扩大了糠醛工业化应用的潜力。
第4章主要围绕乙酰丙酸,研究了乙酰丙酸—步高效转化戊酸酯类含氧燃料的过程。研究发现合适的催化剂酸强度和适当的加氢活性是反应的关键因素。制备了一种双功能催化剂Ru/SBA-SO3H,戊酸乙酯和戊酸的选择性随着催化剂Ru/SBA-SO3H酸量的增加而升高,最高选择性达到94%(100%乙酰丙酸转化率)。通过对反应动力学的研究提出了可能的反应途径,并通过实验进行了验证。
最后,对全文进行了总结和展望。
综上所述,本文紧密围绕生物质转化中两种重要的平台分子糠醛和乙酰丙酸,借助非均相催化的手段,实现了木糖到糠醛的高效转化,发展了糠醛转化呋喃类高分子聚酯的新路线,完成了乙酰丙酸到戊酸酯类含氧燃料的一步高效加氢转化。
Biomass resource is a carbon-neutral renewable resource. Because biomass resource is the only one which can be converted into conventional liquid, solid and gaseous fuels and other chemicals among the renewable resources, it has a unique advantage in the process of substitution of fossil resources. Biomass can be converted into the bulk but low value-added products, such as liquid fuels and high value-added chemicals such as succinic acid, sorbitol and glycerin through bio-refinery process. Biomass-based platform molecules are important bridges which linked the biomass feedstocks and target products such as fuels, fuel additives and chemicals. The development of simple and inexpensive process for the preparation of platform molecules and efficient conversion of platform molecules into fuels and chemicals are significant to improve the competitiveness of biomass resources to fossil resources.
Furfural and levulinic acid are two important platform molecules in the biomass conversion process. Furfural can be obtained from the hemicellulose in the lignocellulosic biomass. At present, the catalysts in large-scale industrial production of furfural are inorganic acids. However, there are some problems of traditional inorganic acid catalysts, such as equipment corrosion and environmental pollution. In order to solve the above problems, we developed a tantalum hydroxide-based solid acid catalyst TA-p to catalytic convert D-xylose to furfural. On the basis of the conversion of D-xylose to furfural, we have established a multi-step catalytic conversion of furfural into poly(butylene2,5-furandicarboxylate)(PBF) for the first time.
Levulinic acid could be cost-effectively produced from lignocellulosic materials via acid hydrolysis process in high yields. Additionally, the LA derivatives which feature with proper combustion properties and energy density have the potential to serve as fuel additives. Among them, valerate esters as novel oxygenated fuels could be blended in both gasoline and diesel. Currently the preparation of valerate esters has been reported, but there is still lack of the research on the efficient conversion of levulinic acid into valerate esters in one step. We have developed a bifunctional catalyst Ru/SBA-SO3H to achieve efficient catalytic one-step conversion of levulinic acid into valerate esters as oxygenated fuels.
Chapter1presetned the concepts of biomass resources and biorefineries, then a brief overview of the use of biomass in several ways and biomass-based platform molecules was introduced. We reviewed of the preparation of furfural and the transformation of furfural and levulinic acid.
Chapter2described the solid acid catalyst TA-p in water-organic solvent biphasic system for selective catalytic conversion of D-xylose to furfural. This process was performed both in a batch reactor and a continuous fixed-bed reactor. In the batch process, D-xylose conversion and furfural yield were significantly affected by the organic solvents, reaction temperature and time.1-butanol, which could be obtained through the fermentation of biomass-based carbohydrates, was selected as organic phase and the highest furfural yield of59%was achieved with D-xylose conversion of96%at180℃in the continuous process. Moreover, the long-time stability test for80h under the optimal conditions showed excellent stability of TA-p.
Chapter3studied a multi-step route of catalytic conversion of furfural into2,5-furandicarboxylic acid-based polyester PBF with total carbon utilization. Catalytic oxidation of furfural into furoate could be easily achieved with a selectivity of93%at100%furfural conversion. The best results of catalytic disproportionation of furoate to furan and2,5-furandicarboxylate were obtained with the selectivity to2,5-FDCA of86%at61%furoate conversion. We have presented a new pathway of converting furfural which was a bulk biomass-based chemical into the key monomer2,5-FDCA of2,5-furandicarboxylic acid-based polyester with a good overall selectivity (80%for the two-step process). This route provides a hitherto important yet neglected strategy linking the platform molecule furfural from C5sugars and2,5-FDCA from C6sugars. It opens a new pathway for biorefinery and further study of the process is necessary. Moreover, furan was converted into1,4-BDO with the highest selectivity of70%at99%furan conversion. The furan-based polyester PBF was prepared from2,5-FDCA and1,4-BDO with total carbon utilization of furfural.
Chapter4mainly discussed the hydrogenation of levulinic acid to valerate esters over supported Ru catalysts. The suitable acidity and proper hydrogenation activity of catalyst were the key factors for the reaction. A bifunctional catalyst Ru/SBA-SO3H was developed as active catalyst and characterized. The increase in the amount of acid sites on the support improved the selectivity to EV and VA, and the highest yield of94%to EV and VA was achieved. Probable reaction pathways were proposed and verified.
Finally, we summaried the full paper and outlook the future work.
In summary, this paper focused on two important platform molecules of furfural and levulinic acid in biomass conversion. The efficient conversion of D-xylose to furfural, a new route of conversion of furfural into2,5-furandicarboxylic acid-based polyester and the hydrogenation of levulinic acid to valerate esters in one-step with heterogeneous catalysis were achieved.
引文
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