生物柴油的绿色合成
摘要
生物柴油作为一种绿色可再生能源，受到世界各国的广泛关注。本论文主要对生物柴油的合成进行了研究，针对不同性质的原料，开发了不同的绿色高效催化过程。在生物柴油生产中，原料成本占整个生产成本的70%以上，虽然原料来源广泛，但不同来源的原料在组成和性质上有很大的差别。对生物柴油合成影响最显著的是原料油脂的酸值和水分含量，而不同来源原料的酸值和水分含量也有很大的差别，为了解决以上问题，开发生物柴油的绿色合成工艺，分别针对不同来源，不同酸值的油脂原料，开发了不同的催化过程，主要进行了以下研究：对那些酸值高的原料，采用了酸催化过程。为了解决传统均相酸催化体系存在的设备腐蚀严重，副反应多，后处理复杂，催化剂不能回收等问题，采用离子液体作为绿色催化剂。首先合成了Lewis酸型的离子液体，在考察阴阳离子和优化实验条件的基础上，筛选了最佳催化剂[Et_3NH]Cl-AlCl_3(x=0．7)。该催化剂对反应具有很高的催化活性，催化反应的收率高达99%，而且催化剂可以重复循环使用。但该离子液体自身不稳定，对水敏感，遇水易分解，因此，需要对原料油脂的水分含量进行严格控制。针对Lewis酸型催化剂对水敏感的缺点，合成了磺酸基功能化的离子液体。在优化离子液体结构和反应条件的基础上，筛选出了最佳催化剂[SO_3H-Bmim][HSO_4]。该催化剂具有用量少，催化活性高，对原料的水分要求低等优点。但该催化剂易溶于反应体系，在使用过程中会存在严重的流失，造成催化剂的损失和产品后处理的复杂。为解决以上问题，合成了新型多磺酸基功能化的离子液体，并将其用于生物柴油的合成。由于多磺酸基功能化离子液体的酸度高，其中的多个磺酸基可以相互协调作用，对反应具有很好的催化活性，具有催化剂用量少，反应时间短的优点。同时，由于其阳离子中含多个磺酸基，极性大，与有机相不互溶，而且反应结束后能以固体形式析出，因此，该催化剂在使用过程中不会流失。该催化剂也可以用于酸值高的原料体系，可以很好的将原料中的游离脂肪酸转化为相应的生物柴油产品，提高原料的利用率。四磺酸基功能化的离子液体的催化活性可以与硫酸相媲美，对各种原料油脂均具有较高的催化活性，具有反应时间短，催化效率高，重用性能好等优点，是一种新型高效的绿色催化体系。对那些酸值和水分含量低的油脂原料，采用碱催化体系。碱催化具有反应活性高，反应时间短，甲醇用量少等优点，是一种高效合成生物柴油的方法。为了克服传统均相催化剂的缺点，合成了一系列负载型固体碱催化剂，获得了很好的效果。首先，考察了KF负载型催化剂的性能，考察了催化剂制备方法，载体种类，处理温度等因素对催化活性的影响。其中，KF/Al_2O_3催化剂具有很好的催化活性，但该催化剂在高温条件下容易失活；KF/CaO催化剂也具有很好的活性，但催化剂需要的热处理温度高，而且催化剂储存上的不便也会限制了催化剂的使用。KF/MgO在400℃处理，可得催化活性最高的催化剂，随着处理温度的升高，催化剂的催化活性会降低。随后，考察了K_2CO_3负载型催化剂的活性。对于K_2CO_3/Al_2O_3而言，由于载体自身没有碱性，催化活性中心主要来源于碳酸钾。对K_2CO_3/MgO而言，由于载体自身具有一定的碱性，其催化活性同时来源于载体和活性组分。载体可以在较低的温度下脱水产生具有晶格缺陷的氧化镁活性中心，同时，碳酸钾在高温分解也可产生高活性中心。因此，催化剂在400℃处理下，即可产生第一种类型的强碱性活性中心，而随着温度的进一步升高，第一类高活性中心逐渐消失，而随之又产生第二类活性中心，可使催化剂在很宽的温度范围中保持高活性。最后，合成了KOAc负载型催化剂，该催化剂的活性中心不是直接来源于醋酸钾，而是醋酸钾高温分解产生的碱性中心。由于碳酸钾是原位生成，进一步分解会更容易，可以进一步分解成高活性的催化中心，载体对催化剂活性中心的产生具有一定的影响。综合以上的各种因素，筛选K_2CO_3/MgO为最佳的催化体系，能够高效催化低酸值油脂合成生物柴油。对于一些酸值和水分含量都不高的原料，合成了新型耐酸耐水型催化剂。首先通过直接固相反应法合成了催化剂前驱体，然后通过高温焙烧合成了新型耐酸耐水性固体碱催化剂。在对催化剂进行耐水实验时，发现与传统催化剂，包括均相与非均相催化剂相比，新型催化剂具有很强的耐水性，可以对水分含量在1%左右的原料保持较好的催化活性。催化剂良好的耐水性是其耐酸性的基础，考察了催化剂的耐酸性。催化剂的耐酸性主要体现在其强碱中心与反应体系中的游离酸进行反应，将游离酸消耗掉，而在此过程中，对于上述反应可能生成的水分可以通过催化剂上的耐水中心吸收而将其消除。当水分含量和酸值在一定的范围时，催化剂可以重复循环使用许多次，而催化活性基本不变。
Biodiesel has received more and more attention for its great potential as the greenrenewable energy.The novel efficient and green procedures for the synthesis of biodieselhave been carried out.As we all know,the cost of the raw material was over 70% of thetotal cost during the biodeisel production.There were numerous raw materials for thesynthesis of biodiesel including vegetable oil,animal fat,waste oil etc.The acidity andwater content were quite different for different raw materials:some raw materials ownedlow acidity and water content while others high.The acidity of the raw materials wasvery important because different catalytic procedures should be chose for the synthesis ofbiodiesel based on the acidity of the raw materials.In order to develop green and efficientprocedure for the synthesis of biodiesel from different raw materials,both acid and basecatalytic processes have been carried out.
The acid-catalyzed procedures should be taken for the raw materials with highacidity and water content.The ionic liquids were used as the green acid catalysts insteadof the traditional sulfonic acid to overcome the drawbacks such as high causticity andunreusability.The traditional Lewis acid ionic liquids were synthesized to catalyze thereaction first.After optimizing the reaction conditions and the ionic liquid composition,[Et_3NH]Cl-AlCl_3(x=0.7) was chose as the most efficient catalyst for the reaction withhigh activity and reusability.But the ionic liquid was very sensitive to water,which madethe water content of the raw materials be controlled strictly.Then,the SO3H functionedionic liquids were used for the reactions.The [SO_3H-Bmim][HSO_4] was selected for thereaction with the advantages of high activity,small usage,and insensitivity to water andacidity.But the catalyst was easily dissolved in the organic phase,which caused the greatloss of the catalyst.Moreover,the loss of the catalyst made the purification of the productmore difficult.The novel multi-SO_3H functioned ionic liquids have been synthesized forthe reactions.The novel ionic liquids owned much higher acidity and could catalyze thereaction more efficiently with smaller usage and shorter reaction time.Moreover thenovel ionic liquids were insoluble in the organic phase,and could be reused directlywithout loss of activity.The catalysts owned almost equal activity to the sulfonic acid,which made the catalysts one of the best choices for the synthesis of biodiesel using raw materials with high acidity.
The base catalysts owned much higher activity compared to the acid catalysts.Thesupported solid base catalysts have been synthesized for the reactions instead of thehomogeneous base catalysts.KF supported on various carriers were applied to thereaction first.KF/Al_2O_3 was very efficient for the reaction,but the catalyst was instable tothe thermal treatment.The catalyst lost the activity when treated at the temperature above400℃.KF/CaO was also efficient for the reaction,but the high activity was obtainedthrough thermal treatment at relatively high temperature.Also the catalyst was easy toabsorb the water and carbon dioxide in the air and lose its activity.KF/MgO obtained thehigh activity after treated at 400℃and the activity decreased when higher temperaturewas introduced.Then,K_2CO_3 was used as the active compound to prepare solid basecatalysts.The active sites of the catalyst K_2CO_3/Al_2O_3 was originated from K_2CO_3.TheK_2CO_3/MgO showed very high activity for the reaction with the low temperature of 400℃needed to generate the efficient active sites.The high activity remained the same whenthe catalyst was treated at higher temperature.The KOAc supported on different carrierswere also prepared for the reactions.Here the active sites were produced through thedecomposition of KOAc at high temperature.The carriers such as MgO could alsoprovide the active sites during the thermal treatment.To sum up,K_2CO_3/MgO was themost efficient catalyst for the synthesis of biodiesel using the raw materials with lowacidity.
Here the catalysts with waterproof and acid proof ability were synthesized for theraw materials with low acidity and water content.The catalysts were synthesized throughthe solid-state reactions and thermal treatment.The results showed that the novel catalystowned high waterproof ability compared to the traditional catalysts,and the catalyticactivity was still very high for the raw materials with the water content of 1%.The highwaterproof ability is the basis of the acid proof ability.For the strong base sites reactedwith the free acids in the raw materials and produce the corresponding water.The catalystalso could be reused after the reactions with high acidity and water content.
Biodiesel has received more and more attention for its great potential as the greenrenewable energy.The novel efficient and green procedures for the synthesis of biodieselhave been carried out.As we all know,the cost of the raw material was over 70% of thetotal cost during the biodeisel production.There were numerous raw materials for thesynthesis of biodiesel including vegetable oil,animal fat,waste oil etc.The acidity andwater content were quite different for different raw materials:some raw materials ownedlow acidity and water content while others high.The acidity of the raw materials wasvery important because different catalytic procedures should be chose for the synthesis ofbiodiesel based on the acidity of the raw materials.In order to develop green and efficientprocedure for the synthesis of biodiesel from different raw materials,both acid and basecatalytic processes have been carried out.
The acid-catalyzed procedures should be taken for the raw materials with highacidity and water content.The ionic liquids were used as the green acid catalysts insteadof the traditional sulfonic acid to overcome the drawbacks such as high causticity andunreusability.The traditional Lewis acid ionic liquids were synthesized to catalyze thereaction first.After optimizing the reaction conditions and the ionic liquid composition,[Et_3NH]Cl-AlCl_3(x=0.7) was chose as the most efficient catalyst for the reaction withhigh activity and reusability.But the ionic liquid was very sensitive to water,which madethe water content of the raw materials be controlled strictly.Then,the SO3H functionedionic liquids were used for the reactions.The [SO_3H-Bmim][HSO_4] was selected for thereaction with the advantages of high activity,small usage,and insensitivity to water andacidity.But the catalyst was easily dissolved in the organic phase,which caused the greatloss of the catalyst.Moreover,the loss of the catalyst made the purification of the productmore difficult.The novel multi-SO_3H functioned ionic liquids have been synthesized forthe reactions.The novel ionic liquids owned much higher acidity and could catalyze thereaction more efficiently with smaller usage and shorter reaction time.Moreover thenovel ionic liquids were insoluble in the organic phase,and could be reused directlywithout loss of activity.The catalysts owned almost equal activity to the sulfonic acid,which made the catalysts one of the best choices for the synthesis of biodiesel using raw materials with high acidity.
The base catalysts owned much higher activity compared to the acid catalysts.Thesupported solid base catalysts have been synthesized for the reactions instead of thehomogeneous base catalysts.KF supported on various carriers were applied to thereaction first.KF/Al_2O_3 was very efficient for the reaction,but the catalyst was instable tothe thermal treatment.The catalyst lost the activity when treated at the temperature above400℃.KF/CaO was also efficient for the reaction,but the high activity was obtainedthrough thermal treatment at relatively high temperature.Also the catalyst was easy toabsorb the water and carbon dioxide in the air and lose its activity.KF/MgO obtained thehigh activity after treated at 400℃and the activity decreased when higher temperaturewas introduced.Then,K_2CO_3 was used as the active compound to prepare solid basecatalysts.The active sites of the catalyst K_2CO_3/Al_2O_3 was originated from K_2CO_3.TheK_2CO_3/MgO showed very high activity for the reaction with the low temperature of 400℃needed to generate the efficient active sites.The high activity remained the same whenthe catalyst was treated at higher temperature.The KOAc supported on different carrierswere also prepared for the reactions.Here the active sites were produced through thedecomposition of KOAc at high temperature.The carriers such as MgO could alsoprovide the active sites during the thermal treatment.To sum up,K_2CO_3/MgO was themost efficient catalyst for the synthesis of biodiesel using the raw materials with lowacidity.
Here the catalysts with waterproof and acid proof ability were synthesized for theraw materials with low acidity and water content.The catalysts were synthesized throughthe solid-state reactions and thermal treatment.The results showed that the novel catalystowned high waterproof ability compared to the traditional catalysts,and the catalyticactivity was still very high for the raw materials with the water content of 1%.The highwaterproof ability is the basis of the acid proof ability.For the strong base sites reactedwith the free acids in the raw materials and produce the corresponding water.The catalystalso could be reused after the reactions with high acidity and water content.
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