生物质基碳水化合物催化转化制乳酸甲酯
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摘要
乳酸甲酯是一类重要的羟基酯类化合物,主要用作合成香料和除草剂。它又是一类重要的工业溶剂。乳酸甲酯水解后可以制备成平台化合物乳酸。传统的乳酸以生物发酵为主,存在生产周期长、产生大量废弃物、反应条件严格等缺点。随着乳酸及其衍生物的广泛应用,传统的生产方式显然已经不能满足现代需要,近几年来科学家们致力于研究开发新的简单环保的化学方法制备乳酸及其衍生物。
本文的工作内容是以生物质基碳水化合物为原料,以固体碱、酸性介孔分子筛以及具有酸碱两性的过渡金属氧化物为催化剂在甲醇中制备乳酸甲酯。用XPD、 BET、TEM、CO2-TPD、NH3-TPD、Py-IR、IR等技术详细分析表征了各催化剂的物理化学性质,考察了催化剂的催化活性及其相关影响因素。得到了以下主要结论：
(1)固体碱催化剂MgO对生物质基碳水化合物转化为乳酸甲酯有催化活性,其催化活性和表面碱性相关。对于不同来源以及不同焙烧温度活化的MgO来说,只具有弱碱性位点的MgO的催化活性最佳。在最优反应条件下乳酸甲酯的产率接近30%。催化剂的稳定性及循环使用研究表明,反应前后催化剂的结构与碱性几乎没有变化,经多次使用,催化活性几乎没有降低。水对MgO的催化活性有不利的影响。
(2)研究中发现,甲醇对生物质基碳水化合物制乳酸甲酯也有催化作用。对比不同一元醇为溶剂的反应,结果显示甲醇的反应活性与催化活性最佳。这主要是因为甲醇比其他一元醇的极性都大。而非质子传递惰性溶剂正己烷完全没有反应活性。
(3)制备了具有高度有序介孔结构Sn-MCM-41和部分有序介孔结构的SnO2/SiO2-a,这两种催化剂对生物质基碳水化合物转化成乳酸甲酯都具有较好的催化活性。在最优反应条件下乳酸甲酯的产率在40%左右。中等强度酸性对生成乳酸甲酯有主要作用,分子筛催化剂的总酸量越高催化剂的活性越好。催化剂的稳定性及循环使用研究表明,Sn-MCM-41和SnO2/SiO2-a都具有良好的稳定性,循环使用五次后催化剂的活性改变不大。反应过程中两种催化剂的Sn流失量小于0.15%,TEM与Py-IR结果显示反应前后催化剂的结构以及酸性种类没有明显变化。(4)制备了NiO、Cr2O3、TiO2这几种过渡金属氧化物和稀土金属氧化物La2O3,对于生物质碳基水化合物催化转化成乳酸甲酯的反应,它们的催化活性顺序如下：NiO>La2O3>Cr2O3>TiO2。在最优反应条件下NiO催化葡萄糖制得的乳酸甲酯的产率可达40%。对这几种催化剂的酸碱性的分析表征表明：催化活性主要与催化剂的酸性有关,酸性位点的数目越多,催化剂催化活性越好。催化剂表面碱性与催化剂活性之间没有明显的联系。NiO具有良好的循环使用性能,在反应过程中有约0.15%的Ni流失,循环使用三次后催化剂的催化活性没有显著降低。XRD与Py-IR结果显示反应前后催化剂的晶体结构以及酸性种类没有明显变化。
Methyl lactate is a kind of important hydroxyl ester. It is used in spices and herbicides mainly. In addition, it is a kind of important industrial solvents. And it is widely used in medicine, resin coating, adhesive, cleaning lotion, printing ink, cosmetics, cigarettes, drink, ice cream, and other food industries. Methyl lactate can be hydrolyzed into platform lactic acid. At present, lactic acid is produced by either bacterial fermentation. However, enzyme catalysis processes show many drawbacks, such as long reaction time, formation of large amount of calcium sulfate wastes, and very strict reaction condition. Currently, the growing demand for lactic acid based materials calls attention to the improvement of unpractical conventional processes with an efficient and sustainable chemical route used for lactic acid production.
In this work, biomass-derived carbohydrates were used as substrates. Solid base, acidic zeolites, amphipathic transition metal oxide were used as catalysts. Catalysts were characterized by XRD, BET, TEM, CO2-TPD, NH3-TPD, and Py-IR. The influence factors of catalytic activity were researched. We prove the following conclusions:
(1) Magnesium oxide can be used as solid base catalyst for the production of methyl lactate from biomass-derived carbohydrate in methanol for the first time. MgO with the highest concentration of weakly basic sites was found to show the highest catalytic activity for the conversion of sugars to methyl lactate. The yield of methyl lactate reached nearly30%under optimal reaction conditions. The catalyst can be reused without deactivation for many times. Water showed negative effect to the formation of methyl lactate.
(2) Methanol also showed catalytic activity in this chemical system. Different monohydric alcohols were used as solvent for the blank run reactions. And methanol showed the best catalytic activity. When hexane, a kind of proton transfer inert solvent, was used as solvent, no methyl lactate was detected.
(3) Sn-MCM-41and SnO2/SiO2-a with only partly MCM-41structure were prepared. Both catalysts showed high catalytic activity for the conversion of sugars to methyl lactate. The yield of methyl lactate reached nearly40%under optimal reaction conditions. The methyl lactate yield was closely related to reaction temperature, reaction times, and the type together with the amount of the acid sites of the catalyst. The catalytic activity was improved with the increase of the total acid content of catalysts. The acidic sites and mesoporous structures of reused catalysts did not change much. The catalysts were active and can be reused without significant decrease in the catalytic activity after being used for five recycles. The TEM images and Py-IR of reused catalysts indicated unchanged mesoporous structures and acidic sites.
(4) NiO, La2O3, Cr2O3, and TiO2were prepared. Their catalytic activities were in following order:NiO> La2O3> Cr2O3> TiO2. The yield of methyl lactate reached nearly40%under optimal reaction conditions with NiO as catalyst. The catalytic activity was improved with the increase of the total acid content of catalysts. The base content of catalysts did not show significant influence in catalytic activity. The catalysts were active and can be reused without significant decrease in the catalytic activity after being used for three recycles. The XRD pattern and Py-IR of reused catalyst indicated unchanged crystal structures and acidic sites.
本文的工作内容是以生物质基碳水化合物为原料,以固体碱、酸性介孔分子筛以及具有酸碱两性的过渡金属氧化物为催化剂在甲醇中制备乳酸甲酯。用XPD、 BET、TEM、CO2-TPD、NH3-TPD、Py-IR、IR等技术详细分析表征了各催化剂的物理化学性质,考察了催化剂的催化活性及其相关影响因素。得到了以下主要结论：
(1)固体碱催化剂MgO对生物质基碳水化合物转化为乳酸甲酯有催化活性,其催化活性和表面碱性相关。对于不同来源以及不同焙烧温度活化的MgO来说,只具有弱碱性位点的MgO的催化活性最佳。在最优反应条件下乳酸甲酯的产率接近30%。催化剂的稳定性及循环使用研究表明,反应前后催化剂的结构与碱性几乎没有变化,经多次使用,催化活性几乎没有降低。水对MgO的催化活性有不利的影响。
(2)研究中发现,甲醇对生物质基碳水化合物制乳酸甲酯也有催化作用。对比不同一元醇为溶剂的反应,结果显示甲醇的反应活性与催化活性最佳。这主要是因为甲醇比其他一元醇的极性都大。而非质子传递惰性溶剂正己烷完全没有反应活性。
(3)制备了具有高度有序介孔结构Sn-MCM-41和部分有序介孔结构的SnO2/SiO2-a,这两种催化剂对生物质基碳水化合物转化成乳酸甲酯都具有较好的催化活性。在最优反应条件下乳酸甲酯的产率在40%左右。中等强度酸性对生成乳酸甲酯有主要作用,分子筛催化剂的总酸量越高催化剂的活性越好。催化剂的稳定性及循环使用研究表明,Sn-MCM-41和SnO2/SiO2-a都具有良好的稳定性,循环使用五次后催化剂的活性改变不大。反应过程中两种催化剂的Sn流失量小于0.15%,TEM与Py-IR结果显示反应前后催化剂的结构以及酸性种类没有明显变化。(4)制备了NiO、Cr2O3、TiO2这几种过渡金属氧化物和稀土金属氧化物La2O3,对于生物质碳基水化合物催化转化成乳酸甲酯的反应,它们的催化活性顺序如下：NiO>La2O3>Cr2O3>TiO2。在最优反应条件下NiO催化葡萄糖制得的乳酸甲酯的产率可达40%。对这几种催化剂的酸碱性的分析表征表明：催化活性主要与催化剂的酸性有关,酸性位点的数目越多,催化剂催化活性越好。催化剂表面碱性与催化剂活性之间没有明显的联系。NiO具有良好的循环使用性能,在反应过程中有约0.15%的Ni流失,循环使用三次后催化剂的催化活性没有显著降低。XRD与Py-IR结果显示反应前后催化剂的晶体结构以及酸性种类没有明显变化。
Methyl lactate is a kind of important hydroxyl ester. It is used in spices and herbicides mainly. In addition, it is a kind of important industrial solvents. And it is widely used in medicine, resin coating, adhesive, cleaning lotion, printing ink, cosmetics, cigarettes, drink, ice cream, and other food industries. Methyl lactate can be hydrolyzed into platform lactic acid. At present, lactic acid is produced by either bacterial fermentation. However, enzyme catalysis processes show many drawbacks, such as long reaction time, formation of large amount of calcium sulfate wastes, and very strict reaction condition. Currently, the growing demand for lactic acid based materials calls attention to the improvement of unpractical conventional processes with an efficient and sustainable chemical route used for lactic acid production.
In this work, biomass-derived carbohydrates were used as substrates. Solid base, acidic zeolites, amphipathic transition metal oxide were used as catalysts. Catalysts were characterized by XRD, BET, TEM, CO2-TPD, NH3-TPD, and Py-IR. The influence factors of catalytic activity were researched. We prove the following conclusions:
(1) Magnesium oxide can be used as solid base catalyst for the production of methyl lactate from biomass-derived carbohydrate in methanol for the first time. MgO with the highest concentration of weakly basic sites was found to show the highest catalytic activity for the conversion of sugars to methyl lactate. The yield of methyl lactate reached nearly30%under optimal reaction conditions. The catalyst can be reused without deactivation for many times. Water showed negative effect to the formation of methyl lactate.
(2) Methanol also showed catalytic activity in this chemical system. Different monohydric alcohols were used as solvent for the blank run reactions. And methanol showed the best catalytic activity. When hexane, a kind of proton transfer inert solvent, was used as solvent, no methyl lactate was detected.
(3) Sn-MCM-41and SnO2/SiO2-a with only partly MCM-41structure were prepared. Both catalysts showed high catalytic activity for the conversion of sugars to methyl lactate. The yield of methyl lactate reached nearly40%under optimal reaction conditions. The methyl lactate yield was closely related to reaction temperature, reaction times, and the type together with the amount of the acid sites of the catalyst. The catalytic activity was improved with the increase of the total acid content of catalysts. The acidic sites and mesoporous structures of reused catalysts did not change much. The catalysts were active and can be reused without significant decrease in the catalytic activity after being used for five recycles. The TEM images and Py-IR of reused catalysts indicated unchanged mesoporous structures and acidic sites.
(4) NiO, La2O3, Cr2O3, and TiO2were prepared. Their catalytic activities were in following order:NiO> La2O3> Cr2O3> TiO2. The yield of methyl lactate reached nearly40%under optimal reaction conditions with NiO as catalyst. The catalytic activity was improved with the increase of the total acid content of catalysts. The base content of catalysts did not show significant influence in catalytic activity. The catalysts were active and can be reused without significant decrease in the catalytic activity after being used for three recycles. The XRD pattern and Py-IR of reused catalyst indicated unchanged crystal structures and acidic sites.
引文
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