固体催化大豆油化学改性的研究
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摘要
植物油的化学改性是拓宽其在工业领域应用的前提，其分子结构特性决定了链端酯基的酯交换和碳链中双键的环氧化两种基础改性反应。改善两种基础反应过程的核心在于新型固体催化剂的开发使用。本论文以大豆油为底物，针对酯交换反应，制备了以水滑石为前驱物的固体碱催化剂，重点研究了其对大豆油和乙二醇的酯交换反应的催化性能；针对环氧化反应，选取埃洛石纳米管(HNTs)为载体，进行磷钨杂多酸（{PO_4[W(O)(O_2)_2]_4}~(3-)）和甲基三氧化铼（MTO）两种高效催化剂的固体负载化，重点研究了两种负载型固体催化剂对以H_2O_2为氧化剂的大豆油环氧化反应的催化性能。主要研究内容及结论如下：
对于酯交换反应的固体碱催化剂，首先采用共沉淀法制备了晶型良好、晶相单一的铝锂水滑石（Li-Al LDHs），经煅烧后，Li-Al LDHs层状结构坍塌，得到大比表面积大孔容的铝锂双金属复合氧化物（Li-Al LDO）。为了抑制Li-Al LDHs的记忆效应，进一步采用硅烷偶联剂Z6020进行改性。改性后的Li-Al LDO仍保持其多孔结构，并且平均孔径扩大。Li-Al LDO(Cat-1)和改性的Li-Al LDO (Cat-2)作为固体碱催化剂，均能在无溶剂条件下催化大豆油乙二醇酯交换反应，且Cat-1和Cat-2均可重复利用4次。在反应温度160℃，醇油摩尔比10:1，催化剂用量5wt%，搅拌速率1000rpm，反应时间2小时条件下，Li-Al LDO和改性的Li-AlLDO催化酯交换反应产物的收率均达到93%以上。但硅烷偶联剂改性可以大大降低催化剂的再生温度, Cat-1的再生温度为450℃，而Cat-2的再生温度为120℃。再生三次后Cat-1和Cat-2仍可用于催化大豆油乙二醇酯交换反应。
对于过氧磷钨杂多酸的负载，首先采用硅烷偶联剂Z-6020对HNTs载体表面进行氨基化改性，再采用季铵化试剂一溴己烷和碘甲烷将氨基进行季铵化处理，在HNTs载体表面接枝上季铵阳离子。通过离子交换作用，将{PO_4[W(O)(O_2)_2]_4}~(3-)负载到季铵化改性的HNTs表面，HNTs与{PO_4[W(O)(O_2)_2]_4}~(3-)催化剂通过离子键相连。所得到的负载型{PO_4[W(O)(O_2)_2]_4}~(3-)固体催化剂，在无溶剂条件下催化大豆油环氧化反应。机械搅拌与超声波振荡并用的方式加强了大豆油-H_2O_2-负载型{PO_4[W(O)(O_2)_2]_4}~(3-)固体催化剂三相反应体系的传质过程，提高了双键转化率和环氧大豆油收率。催化剂制备过程中加入相转移试剂三正辛基甲基氯化铵可以提高催化效率，增加双键转化率和环氧大豆油收率。负载型{PO_4[W(O)(O_2)_2]_4}~(3-)固体催化剂具有良好的可重复利用性，并且再生过程简单。催化剂重复利用3次后仍能催化大豆油环氧化反应。失活催化剂重新负载{PO_4[W(O)(O_2)_2]_4}~(3-)活性中心和相转移试剂即可恢复催化活性，实现再生。
对于甲基三氧化铼的负载，首先利用埃洛石表面羟基，先将活性表面原子转移自由基聚合（SI-ATRP）的引发剂锚定到表面，然后在埃洛石表面引发4-乙烯基吡啶（4-VP）活性聚合。表面接枝的聚4-乙烯基吡啶（P-4VP）聚合物链表现出分子量单分散性，其长度可以通过调节聚合反应时间来控制。负载过程中MTO中的Re原子与吡啶环上的N原子配位，利用配位作用的可化学计量特性实现了MTO催化剂负载量的可控性。所制备的负载型MTO固体催化剂可以催化大豆油环氧化反应，得到环氧大豆油产物。且选择性很高，无副反应发生。
Chemical modification is the premise to industrial application of plant oils.Transesterification and epoxidation are two fundamental reactions of chemical modification whichare dependent on moleculer structure of plant oils. Synthesis and application of novel solidcatalysts is the core to improve the two chemical modification reactions. In the thesis, solid basecatalysts for transesterification were synthesized using layered double hydroxides (LDHs) as theprecursor and its catalytic behavior in the transesterification of soybean oil by ethylene glycol wasstudied. Two supported catalysts for epoxidation were prepared via immobilization of peroxophosphotungstic acid and methyltrioxorhenium (MTO) onto halloysite nanotubes (HNTs) and itscatalytic behaviors in epoxidation of soybean oil using H_2O_2as oxidant were studied. The relatedexperiments and results are summarized as follow:
For solid base catalysts, crystalline Li-Al LDHs was synthesized through coprecipitation andLi-Al layered double oxide (Li-Al LDO) with larger specific area and pore size was obtained aftercalcining of Li-Al LDHs. To suppress the memory effect of Li-Al LDHs, Li-Al LDO was furthermodified with silane coupling agent Z6020and the modification caused increasing of pore size.Both Li-Al LDO (Cat-1) and modified Li-Al LDO (Cat-2) as catalysts can catalyze thesolvent-free transesterification of soybean oil by ethylene glycol and can be used for4circles.Modification with Z6020can obviously decrease the temperature for regeneration of the catalysts,from450℃for Cat-1to120℃for Cat-2. After three times regeneration, both Cat-1and Cat-2still can catalyze the transesterification of soybean oil. Reaction at160℃for2h at1000rpmstirring rate,10:1ethylene glycol to soybean oil molar ratio, and5wt%catalyst, the yield reachedmore than93%for both Cat-1and Cat-2, respectively.
The immobilization of peroxo phosphotungstic acid ({PO_4[W(O)(O_2)_2]_4}~(3-)) onto HNTsincluded three steps. First, amine groups were anchored onto HNTs through modification with Z-6020. Then amine groups were quaternary-ammonated with CH3I and CH2Br(CH2)4CH3toproduce cationic ions. Finally,{PO_4[W(O)(O_2)_2]_4}~(3-)was immobilized onto HNTs via ion exchange.In solvent-free epoxidation of soybean oil catalyzed by supported {PO_4[W(O)(O_2)_2]_4}~(3-), thecombination of mechanical stirring and ultrasonication was helpful to accelerate the mass transferamong soybean oil-H_2O_2-supported {PO_4[W(O)(O_2)_2]_4}~(3-)catalysts three phases. The introductionof phase transfer agent (methyl tri-n-octyl ammonium chloride) during immobliztion of{PO_4[W(O)(O_2)_2]_4}~(3-)was also helpful to increase the catalytic efficiency. The supported{PO_4[W(O)(O_2)_2]_4}~(3-)still had good catalytic activity after three circles and the deactivated catalystcan be reloaded with {PO_4[W(O)(O_2)_2]_4}~(3-)to recover the activity.
In immobilization of MTO, Poly (4-vinylpyridine)(P-4VP) brushes of different length wasgrafted onto HNTs by living surface-initiated atom transfer radical polymerization (SI-ATRP) andthen MTO was immobilized via coordination of MTO with N in pyridine. As the length of P-4VPbrushes can be adjusted by varying the polymerization time, and the coordination of MTO with Nin pyridine was stoichiometric, controlled immobilization of MTO was realized. Thus resultedsupported MTO is effective for epoxidation of soybean oils. The conversion of soybean oilincreased with MTO loadings, keeping the high selectivity.
对于酯交换反应的固体碱催化剂，首先采用共沉淀法制备了晶型良好、晶相单一的铝锂水滑石（Li-Al LDHs），经煅烧后，Li-Al LDHs层状结构坍塌，得到大比表面积大孔容的铝锂双金属复合氧化物（Li-Al LDO）。为了抑制Li-Al LDHs的记忆效应，进一步采用硅烷偶联剂Z6020进行改性。改性后的Li-Al LDO仍保持其多孔结构，并且平均孔径扩大。Li-Al LDO(Cat-1)和改性的Li-Al LDO (Cat-2)作为固体碱催化剂，均能在无溶剂条件下催化大豆油乙二醇酯交换反应，且Cat-1和Cat-2均可重复利用4次。在反应温度160℃，醇油摩尔比10:1，催化剂用量5wt%，搅拌速率1000rpm，反应时间2小时条件下，Li-Al LDO和改性的Li-AlLDO催化酯交换反应产物的收率均达到93%以上。但硅烷偶联剂改性可以大大降低催化剂的再生温度, Cat-1的再生温度为450℃，而Cat-2的再生温度为120℃。再生三次后Cat-1和Cat-2仍可用于催化大豆油乙二醇酯交换反应。
对于过氧磷钨杂多酸的负载，首先采用硅烷偶联剂Z-6020对HNTs载体表面进行氨基化改性，再采用季铵化试剂一溴己烷和碘甲烷将氨基进行季铵化处理，在HNTs载体表面接枝上季铵阳离子。通过离子交换作用，将{PO_4[W(O)(O_2)_2]_4}~(3-)负载到季铵化改性的HNTs表面，HNTs与{PO_4[W(O)(O_2)_2]_4}~(3-)催化剂通过离子键相连。所得到的负载型{PO_4[W(O)(O_2)_2]_4}~(3-)固体催化剂，在无溶剂条件下催化大豆油环氧化反应。机械搅拌与超声波振荡并用的方式加强了大豆油-H_2O_2-负载型{PO_4[W(O)(O_2)_2]_4}~(3-)固体催化剂三相反应体系的传质过程，提高了双键转化率和环氧大豆油收率。催化剂制备过程中加入相转移试剂三正辛基甲基氯化铵可以提高催化效率，增加双键转化率和环氧大豆油收率。负载型{PO_4[W(O)(O_2)_2]_4}~(3-)固体催化剂具有良好的可重复利用性，并且再生过程简单。催化剂重复利用3次后仍能催化大豆油环氧化反应。失活催化剂重新负载{PO_4[W(O)(O_2)_2]_4}~(3-)活性中心和相转移试剂即可恢复催化活性，实现再生。
对于甲基三氧化铼的负载，首先利用埃洛石表面羟基，先将活性表面原子转移自由基聚合（SI-ATRP）的引发剂锚定到表面，然后在埃洛石表面引发4-乙烯基吡啶（4-VP）活性聚合。表面接枝的聚4-乙烯基吡啶（P-4VP）聚合物链表现出分子量单分散性，其长度可以通过调节聚合反应时间来控制。负载过程中MTO中的Re原子与吡啶环上的N原子配位，利用配位作用的可化学计量特性实现了MTO催化剂负载量的可控性。所制备的负载型MTO固体催化剂可以催化大豆油环氧化反应，得到环氧大豆油产物。且选择性很高，无副反应发生。
Chemical modification is the premise to industrial application of plant oils.Transesterification and epoxidation are two fundamental reactions of chemical modification whichare dependent on moleculer structure of plant oils. Synthesis and application of novel solidcatalysts is the core to improve the two chemical modification reactions. In the thesis, solid basecatalysts for transesterification were synthesized using layered double hydroxides (LDHs) as theprecursor and its catalytic behavior in the transesterification of soybean oil by ethylene glycol wasstudied. Two supported catalysts for epoxidation were prepared via immobilization of peroxophosphotungstic acid and methyltrioxorhenium (MTO) onto halloysite nanotubes (HNTs) and itscatalytic behaviors in epoxidation of soybean oil using H_2O_2as oxidant were studied. The relatedexperiments and results are summarized as follow:
For solid base catalysts, crystalline Li-Al LDHs was synthesized through coprecipitation andLi-Al layered double oxide (Li-Al LDO) with larger specific area and pore size was obtained aftercalcining of Li-Al LDHs. To suppress the memory effect of Li-Al LDHs, Li-Al LDO was furthermodified with silane coupling agent Z6020and the modification caused increasing of pore size.Both Li-Al LDO (Cat-1) and modified Li-Al LDO (Cat-2) as catalysts can catalyze thesolvent-free transesterification of soybean oil by ethylene glycol and can be used for4circles.Modification with Z6020can obviously decrease the temperature for regeneration of the catalysts,from450℃for Cat-1to120℃for Cat-2. After three times regeneration, both Cat-1and Cat-2still can catalyze the transesterification of soybean oil. Reaction at160℃for2h at1000rpmstirring rate,10:1ethylene glycol to soybean oil molar ratio, and5wt%catalyst, the yield reachedmore than93%for both Cat-1and Cat-2, respectively.
The immobilization of peroxo phosphotungstic acid ({PO_4[W(O)(O_2)_2]_4}~(3-)) onto HNTsincluded three steps. First, amine groups were anchored onto HNTs through modification with Z-6020. Then amine groups were quaternary-ammonated with CH3I and CH2Br(CH2)4CH3toproduce cationic ions. Finally,{PO_4[W(O)(O_2)_2]_4}~(3-)was immobilized onto HNTs via ion exchange.In solvent-free epoxidation of soybean oil catalyzed by supported {PO_4[W(O)(O_2)_2]_4}~(3-), thecombination of mechanical stirring and ultrasonication was helpful to accelerate the mass transferamong soybean oil-H_2O_2-supported {PO_4[W(O)(O_2)_2]_4}~(3-)catalysts three phases. The introductionof phase transfer agent (methyl tri-n-octyl ammonium chloride) during immobliztion of{PO_4[W(O)(O_2)_2]_4}~(3-)was also helpful to increase the catalytic efficiency. The supported{PO_4[W(O)(O_2)_2]_4}~(3-)still had good catalytic activity after three circles and the deactivated catalystcan be reloaded with {PO_4[W(O)(O_2)_2]_4}~(3-)to recover the activity.
In immobilization of MTO, Poly (4-vinylpyridine)(P-4VP) brushes of different length wasgrafted onto HNTs by living surface-initiated atom transfer radical polymerization (SI-ATRP) andthen MTO was immobilized via coordination of MTO with N in pyridine. As the length of P-4VPbrushes can be adjusted by varying the polymerization time, and the coordination of MTO with Nin pyridine was stoichiometric, controlled immobilization of MTO was realized. Thus resultedsupported MTO is effective for epoxidation of soybean oils. The conversion of soybean oilincreased with MTO loadings, keeping the high selectivity.
引文
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