微环境调控的多酸催化剂在烯烃环氧化和氧化脱硫中的性能研究
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摘要
燃油中的硫化物在内燃机中转化为SOx，SOx不但毒害尾气净化器中的贵金属催化剂，而且导致空气污染、酸雾和酸雨。随着环境污染的日益严重，环境法规日益严格，为了减少环境污染，燃料油的深度脱硫引起了广泛关注。过去几年中，含硫量10-15ppm的超低硫柴油已经在欧洲，日本，美国等国家得到应用。2013年颁布的GB19147-2013《车用柴油(Ⅳ)》国家标准规定车用柴油硫含量不大于50ppm。而更为严格的国V车用柴油标准未来也有望发布，届时车用汽柴油硫含量将小于10ppm。传统的催化加氢脱硫(HDS)可以有效地除去燃料油中的硫化物、二硫化物等硫化物，但对于二苯并噻吩(DBT)及其衍生物等硫化物的去除效果差。为了达到深度脱硫，HDS常常需要较为苛刻的脱硫条件，在实际应用中运行费用较高。因此，非常必要发展一种在温和条件下深度脱硫的方法。结合萃取或吸附的氧化脱硫被认为是一种非常有前景的方法。过氧化氢是价格便宜、无污染、无腐蚀性，是一种理想的氧化剂。发展温和的条件下过氧化氢作为氧化剂的氧化脱硫工艺对清洁柴油的生产有重大意义。
环氧化物是重要的化工中间体，可以用来合成药品、农药、树脂、塑料等多种产品。目前工业生产环氧化物的方法主要是氯醇法和共氧化法。氯醇法在生产过程中水资源消耗大，产生大量的含氯废水，处理难度大，设备腐蚀严重。共氧化法克服了氯醇法的缺点，但工艺流程长，原料品种多，设备造价高，建设投资大。过氧化氢直接氧化法是由过氧化氢氧化烯烃制环氧化物的新工艺，生产过程中只生成环氧化物和水，工艺流程简单，产品收率高，从源头上消除了污染。
多酸是一大类过渡金属氧簇，是一种高效的氧化还原催化剂。根据多酸-表面活性剂复合物的特点，结合介孔硅胶和氧化石墨烯材料，设计合成了三种微环境调控的多酸催化剂：微反应控制相转移多酸催化剂，多酸溶致液晶催化剂，具有热敏特性的和两亲性的多酸-氧化石墨烯催化剂。通过氧化脱硫和烯烃环氧化反应，阐述了催化剂组成、结构和催化性能之间的关系。
采用硅胶作为多酸催化剂的载体，制备了微反应控制相转移多酸催化剂。用瓶中造船法，先把多酸和表面活性剂的前体（N，N-二甲基十六烷基胺和PW12O403-）封装在硅胶内，用多酸和有机胺的聚集体封住硅胶管道的开口。然后用双氧水同时氧化N，N-二甲基十六烷基胺和PW12O403-，在封闭的硅胶管道内形成微反应控制相转移催化剂。在H2O2/DBT摩尔比=4：1时，反应温度70oC，反应时间2h，DBT氧化为DBTO2的转化率达到100%。催化剂对不同有机硫表现出不同的催化活性，催化活性DBT>BT>噻吩。催化剂的催化活性和稳定性都高，且容易回收和再利用。
用水做溶剂，用双氧水同时氧化多酸和表面活性剂的前体（N，N-二甲基十六烷基胺和PW12O403-），一锅法制备过氧钨多酸溶致液晶催化剂[C16H33(CH3)2NOH]3[PO4{WO(O2)2}2]。通过偏光显微镜，确定了催化剂是一种溶致液晶。反应体系的极性可以控制多酸溶致液晶的溶解和析出，利用多酸溶致液晶的这个性质，为烯烃环氧化反应设计和实现了自分离微乳体系，解决了微乳的破乳问题，反应体系中底物和产物的极性控制了微乳的形成和破乳，方便了产物的分离。为柴油氧化脱硫设计和实现了极性相、多酸溶致液晶相、非极性相三相平衡的催化反应体系，便于产物、副产物、催化剂的分离。在H2O2/环辛烯摩尔比=1：1时，反应温度60oC，反应时间1h，环氧环辛烷产率>99%，选择性>99%；在H2O2/DBT摩尔比=2：1时，反应温度60oC，反应时间3h，DBT氧化为DBTO2的转化率>99%。
用水做溶剂，用双氧水分步氧化多酸和表面活性剂的前体（N，N-二甲基十六烷基胺和PW12O403-），一锅法制备了氧化石墨烯负载过氧钨多酸催化剂。制备过程中，用双氧水剥离修饰后的氧化石墨烯，把催化剂制备成一面亲水一面疏水的两亲性固体粒子，同时催化剂具有热敏特性。多酸-氧化石墨烯催化剂可以包覆疏水的底物，转移至水相中形成微乳，从而催化水相中的氧化反应。在H2O2/环辛烯摩尔比=1：2时，反应温度50oC，反应时间12h，环氧环辛烷产率为94%，选择性为94%；在H2O2/BT摩尔比=4：1时，反应温度50oC，反应时间20h，BT氧化为砜的产率为96%，选择性为>99%。催化剂的热敏特性方便了催化剂的分离和重复使用。
Sulfur in the fuel is converted into SOxin internal-combustion engines.SOxnotonly poisons the noble metal catalyst in the exhaust gas purification, but also causesair pollution, acid rain and mist. Ultra low sulfur diesel with10-15ppm sulfur hasbeen implemented during the past several years in Europe, Japan and USA. Chinesenational standard GB19147-2013prescribes sulfur content must be not more than50ppm.The more stringent standard for diesel will be issued in the future, when thesulfur content of gasoline and diesel will be less than10ppm. Hydrodesulfurizationprocess can effectively remove sulfides and disulfides, but it is not efficient fordibenzothiophene and its derivatives. Hydrodesulfurization process requires severeprocessing conditions to remove the refractory sulfur compounds in fuel, which leadsto escalating the cost of hydrogen and the capital cost for hydrotreating sulfur removal.Therefore, it is necessary to develop methods for production of ultra-low sulfur dieselunder mild conditions. Oxidation desulfurization with extraction or adsorption is avery promising approach. Hydrogen peroxide is cheap, non-polluting andnon-corrosive, which is an ideal oxidant. The development of oxidativedesulfurization process under mild conditions with hydrogen peroxide as oxidant forproduction of clean diesel is very important.
Epoxide is an important chemical intermediate, which can be used to synthesizedrugs, pesticides, resins, plastics and other products. The traditional industry factureof epoxide is chlorohydrination process and organic peroxide process.Chlorohydrination process produces large quantities of poisonous wastewater.Organic peroxide process overcomes the disadvantages of chlorohydrination process,but it requires a large investment. Hydrogen peroxide process is a new technology forepoxide production, which produces only epoxide and water and eliminates thepollution from the source.
Polyoxometalate is a variety of transition metal oxide clusters, which is anefficient redox catalyst. Polyoxometalate-surfactant complexes are combined with themesoporous silica and graphene oxide to form three microenvironment-controlledpolyoxometalate catalysts: micro reaction-controlled phase-transfer catalyst,polyoxometalate lyotropic liquid crystal catalyst, and amphiphilic polyoxometalate-graphene oxide with thermosensitive property. The composition, structure andcatalytic performance of these catalysts are described. These catalysts are applied tooxidative desulfurization and olefin epoxidation.
A micro reaction-controlled phase-transfer catalyst is prepared using silica gel assupport. Using the method of ship in a bottle, surfactant precursor andpolyoxometalate precursor (N,N-dimethyl hexadecyl amine and PW12O403-) areencapsulated in silica, while the ends of silica channels is sealed with micellar-likeaggregates. With the action of H2O2, PW12O403-is converted into {PO4[WO(O2)2]4}3-and N,N-dimethyl hexadecyl amine is converted into C16H33(CH3)2NOH. A microreaction-controlled phase-transfer system is made in the channels of silica, whichpreventes the catalytic active species from losing. Dibenzothiophene is converted intodibenzothiophene sulfone with100%yield under the optimal reaction conditions(H2O2/S molar ratio is4:1, atmospheric pressure,70oC,2h). The catalyst showes highcatalytic activity, stability and recyclability.
[C16H33(CH3)2NOH]3[PO4{WO(O2)2}2] is synthesized by one-pot method inwater with hydrogen peroxide as oxidant (N,N-dimethyl hexadecyl amine andPW12O403-as precursors). It is a polyoxometalate lyotropic liquid crystal catalyst. Thelyotropic liquid crystal property is determined by polarizing optical micrograph. The dissolution and precipitation of the catalyst is controlled by the polar in the system. Totake advantage of this property, a self-separating microemulsion system for olefinepoxidation is designed and implemented, which solve the problem of demulsification.The polar of substrate and product in the reaction system controls the emulsificationand demulsification, which facilitates the separation of the product. A three phase(polar phase, nonpolar phase and liquid crystal phase) balanced catalytic system foroxidative desulfurization of diesel is designed and implemented, which facilitates theseparation of product, by-product and catalyst. Cyclooctene is converted intocyclooctene oxide with>99%yield and>99%selectivity under the optimal reactionconditions (H2O2/cyclooctene molar ratio is1:1,60oC,1h). Dibenzothiophene isconverted into dibenzothiophene sulfone with>99%yield under the optimal reactionconditions (H2O2/S molar ratio is2:1,60oC,3h).
Polyoxometalate-graphene oxide catalyst is synthesized by one-pot method inwater with hydrogen peroxide as oxidant (N,N-dimethyl hexadecyl amine andPW12O403-as precursors). Using hydrogen peroxide to peel off the modified grapheneoxide, the catalyst is prepared. It is a solid particle with one hydrophilic side and onehydrophobic side, while the catalyst has thermal property. The catalyst canencapsulate the hydrophobic substrate and transfer into the aqueous phase to emulsifythe catalytic system when heated. Therefore, the catalyst can catalyze the reaction inwater. Cyclooctene is converted into cyclooctene oxide in water with>94%yield and>94%selectivity under the optimal reaction conditions (H2O2/cyclooctene molar ratiois1:2,50oC,20h). Benzothiophene is converted into benzothiophene sulfone in waterwith>96%yield and>99%selectivity under the optimal reaction conditions (H2O2/Smolar ratio is4:1,50oC,20h). The thermal property of the catalyst facilitates theseparation and reuse of the catalyst.
环氧化物是重要的化工中间体，可以用来合成药品、农药、树脂、塑料等多种产品。目前工业生产环氧化物的方法主要是氯醇法和共氧化法。氯醇法在生产过程中水资源消耗大，产生大量的含氯废水，处理难度大，设备腐蚀严重。共氧化法克服了氯醇法的缺点，但工艺流程长，原料品种多，设备造价高，建设投资大。过氧化氢直接氧化法是由过氧化氢氧化烯烃制环氧化物的新工艺，生产过程中只生成环氧化物和水，工艺流程简单，产品收率高，从源头上消除了污染。
多酸是一大类过渡金属氧簇，是一种高效的氧化还原催化剂。根据多酸-表面活性剂复合物的特点，结合介孔硅胶和氧化石墨烯材料，设计合成了三种微环境调控的多酸催化剂：微反应控制相转移多酸催化剂，多酸溶致液晶催化剂，具有热敏特性的和两亲性的多酸-氧化石墨烯催化剂。通过氧化脱硫和烯烃环氧化反应，阐述了催化剂组成、结构和催化性能之间的关系。
采用硅胶作为多酸催化剂的载体，制备了微反应控制相转移多酸催化剂。用瓶中造船法，先把多酸和表面活性剂的前体（N，N-二甲基十六烷基胺和PW12O403-）封装在硅胶内，用多酸和有机胺的聚集体封住硅胶管道的开口。然后用双氧水同时氧化N，N-二甲基十六烷基胺和PW12O403-，在封闭的硅胶管道内形成微反应控制相转移催化剂。在H2O2/DBT摩尔比=4：1时，反应温度70oC，反应时间2h，DBT氧化为DBTO2的转化率达到100%。催化剂对不同有机硫表现出不同的催化活性，催化活性DBT>BT>噻吩。催化剂的催化活性和稳定性都高，且容易回收和再利用。
用水做溶剂，用双氧水同时氧化多酸和表面活性剂的前体（N，N-二甲基十六烷基胺和PW12O403-），一锅法制备过氧钨多酸溶致液晶催化剂[C16H33(CH3)2NOH]3[PO4{WO(O2)2}2]。通过偏光显微镜，确定了催化剂是一种溶致液晶。反应体系的极性可以控制多酸溶致液晶的溶解和析出，利用多酸溶致液晶的这个性质，为烯烃环氧化反应设计和实现了自分离微乳体系，解决了微乳的破乳问题，反应体系中底物和产物的极性控制了微乳的形成和破乳，方便了产物的分离。为柴油氧化脱硫设计和实现了极性相、多酸溶致液晶相、非极性相三相平衡的催化反应体系，便于产物、副产物、催化剂的分离。在H2O2/环辛烯摩尔比=1：1时，反应温度60oC，反应时间1h，环氧环辛烷产率>99%，选择性>99%；在H2O2/DBT摩尔比=2：1时，反应温度60oC，反应时间3h，DBT氧化为DBTO2的转化率>99%。
用水做溶剂，用双氧水分步氧化多酸和表面活性剂的前体（N，N-二甲基十六烷基胺和PW12O403-），一锅法制备了氧化石墨烯负载过氧钨多酸催化剂。制备过程中，用双氧水剥离修饰后的氧化石墨烯，把催化剂制备成一面亲水一面疏水的两亲性固体粒子，同时催化剂具有热敏特性。多酸-氧化石墨烯催化剂可以包覆疏水的底物，转移至水相中形成微乳，从而催化水相中的氧化反应。在H2O2/环辛烯摩尔比=1：2时，反应温度50oC，反应时间12h，环氧环辛烷产率为94%，选择性为94%；在H2O2/BT摩尔比=4：1时，反应温度50oC，反应时间20h，BT氧化为砜的产率为96%，选择性为>99%。催化剂的热敏特性方便了催化剂的分离和重复使用。
Sulfur in the fuel is converted into SOxin internal-combustion engines.SOxnotonly poisons the noble metal catalyst in the exhaust gas purification, but also causesair pollution, acid rain and mist. Ultra low sulfur diesel with10-15ppm sulfur hasbeen implemented during the past several years in Europe, Japan and USA. Chinesenational standard GB19147-2013prescribes sulfur content must be not more than50ppm.The more stringent standard for diesel will be issued in the future, when thesulfur content of gasoline and diesel will be less than10ppm. Hydrodesulfurizationprocess can effectively remove sulfides and disulfides, but it is not efficient fordibenzothiophene and its derivatives. Hydrodesulfurization process requires severeprocessing conditions to remove the refractory sulfur compounds in fuel, which leadsto escalating the cost of hydrogen and the capital cost for hydrotreating sulfur removal.Therefore, it is necessary to develop methods for production of ultra-low sulfur dieselunder mild conditions. Oxidation desulfurization with extraction or adsorption is avery promising approach. Hydrogen peroxide is cheap, non-polluting andnon-corrosive, which is an ideal oxidant. The development of oxidativedesulfurization process under mild conditions with hydrogen peroxide as oxidant forproduction of clean diesel is very important.
Epoxide is an important chemical intermediate, which can be used to synthesizedrugs, pesticides, resins, plastics and other products. The traditional industry factureof epoxide is chlorohydrination process and organic peroxide process.Chlorohydrination process produces large quantities of poisonous wastewater.Organic peroxide process overcomes the disadvantages of chlorohydrination process,but it requires a large investment. Hydrogen peroxide process is a new technology forepoxide production, which produces only epoxide and water and eliminates thepollution from the source.
Polyoxometalate is a variety of transition metal oxide clusters, which is anefficient redox catalyst. Polyoxometalate-surfactant complexes are combined with themesoporous silica and graphene oxide to form three microenvironment-controlledpolyoxometalate catalysts: micro reaction-controlled phase-transfer catalyst,polyoxometalate lyotropic liquid crystal catalyst, and amphiphilic polyoxometalate-graphene oxide with thermosensitive property. The composition, structure andcatalytic performance of these catalysts are described. These catalysts are applied tooxidative desulfurization and olefin epoxidation.
A micro reaction-controlled phase-transfer catalyst is prepared using silica gel assupport. Using the method of ship in a bottle, surfactant precursor andpolyoxometalate precursor (N,N-dimethyl hexadecyl amine and PW12O403-) areencapsulated in silica, while the ends of silica channels is sealed with micellar-likeaggregates. With the action of H2O2, PW12O403-is converted into {PO4[WO(O2)2]4}3-and N,N-dimethyl hexadecyl amine is converted into C16H33(CH3)2NOH. A microreaction-controlled phase-transfer system is made in the channels of silica, whichpreventes the catalytic active species from losing. Dibenzothiophene is converted intodibenzothiophene sulfone with100%yield under the optimal reaction conditions(H2O2/S molar ratio is4:1, atmospheric pressure,70oC,2h). The catalyst showes highcatalytic activity, stability and recyclability.
[C16H33(CH3)2NOH]3[PO4{WO(O2)2}2] is synthesized by one-pot method inwater with hydrogen peroxide as oxidant (N,N-dimethyl hexadecyl amine andPW12O403-as precursors). It is a polyoxometalate lyotropic liquid crystal catalyst. Thelyotropic liquid crystal property is determined by polarizing optical micrograph. The dissolution and precipitation of the catalyst is controlled by the polar in the system. Totake advantage of this property, a self-separating microemulsion system for olefinepoxidation is designed and implemented, which solve the problem of demulsification.The polar of substrate and product in the reaction system controls the emulsificationand demulsification, which facilitates the separation of the product. A three phase(polar phase, nonpolar phase and liquid crystal phase) balanced catalytic system foroxidative desulfurization of diesel is designed and implemented, which facilitates theseparation of product, by-product and catalyst. Cyclooctene is converted intocyclooctene oxide with>99%yield and>99%selectivity under the optimal reactionconditions (H2O2/cyclooctene molar ratio is1:1,60oC,1h). Dibenzothiophene isconverted into dibenzothiophene sulfone with>99%yield under the optimal reactionconditions (H2O2/S molar ratio is2:1,60oC,3h).
Polyoxometalate-graphene oxide catalyst is synthesized by one-pot method inwater with hydrogen peroxide as oxidant (N,N-dimethyl hexadecyl amine andPW12O403-as precursors). Using hydrogen peroxide to peel off the modified grapheneoxide, the catalyst is prepared. It is a solid particle with one hydrophilic side and onehydrophobic side, while the catalyst has thermal property. The catalyst canencapsulate the hydrophobic substrate and transfer into the aqueous phase to emulsifythe catalytic system when heated. Therefore, the catalyst can catalyze the reaction inwater. Cyclooctene is converted into cyclooctene oxide in water with>94%yield and>94%selectivity under the optimal reaction conditions (H2O2/cyclooctene molar ratiois1:2,50oC,20h). Benzothiophene is converted into benzothiophene sulfone in waterwith>96%yield and>99%selectivity under the optimal reaction conditions (H2O2/Smolar ratio is4:1,50oC,20h). The thermal property of the catalyst facilitates theseparation and reuse of the catalyst.
引文
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