纳米碳酸盐的制备及其化学反应行为的研究
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摘要
乙醇钠等是有机合成工业常用的强碱，但存在腐蚀严重、副反应多、产品分离复杂、收率较低等缺点，很多有机合成工业改用碳酸盐尤其是碳酸钾。但由于碳酸钾碱性较弱，其参与的化学反应具有高温、高压、反应时间长等缺点。由于特殊的物理、化学性能，纳米材料的制备及其在有机合成中的应用成为近年来的研究热点，但纳米碳酸钾的制备及其在有机合成中的应用研究未见报道。本论文目的是制备纳米碳酸钾，取代传统强碱，应用于有机合成反应，实现有机合成的绿色化。主要研究内容和结果如下：
1.采用高频共振研磨机制备纳米碳酸钾，对影响纳米碳酸钾粒径的因素进行了考察。结果表明，湿法研磨比干法研磨制备的碳酸钾粉体粒径更小，质子性有机溶剂利于湿法研磨制备碳酸钾粉体，若加入少量月桂酸，碳酸钾粉体的粒径会进一步降低。在无水乙醇中加入碳酸钾物质的量0.3%的月桂酸，可以制备平均粒径为98nm的纳米碳酸钾，其中小于100nm的纳米碳酸钾颗粒占75%。测试表明，在质子性有机溶剂中纳米碳酸钾表现出较强的碱性，可以取代乙醇钠等强碱促使丙二酸二乙酯与苄基氯进行烃基化反应。
2.以纳米碳酸钾取代乙醇钠等强碱，研究了活泼亚甲基化合物与卤代烃在非水有机溶剂中的烃基化反应，考察了反应的不同影响因素。结果表明，质子性有机溶剂利于反应的进行；不同的底物和卤代烃，反应活性有差异，对于Br,Cl-二卤代烷烃，活泼亚甲基化合物可以与溴代烃发生选择性烃基化反应。在无水乙醇中50-80℃反应，活泼亚甲基化合物的单烃基化产品收率为82-90%，高于乙醇钠法的收率。
3.以纳米碳酸钾取代乙醇钠等强碱，研究了双酚A等二羟基酚类化合物与卤代烃在非水溶剂中的Williamson反应，考察了反应的不同影响因素。结果表明，质子性有机溶剂利于反应的进行，在质子性有机溶剂中双酚A等酚类化合物的两个羟基分步与卤代烃进行反应，与传统强碱法不同。在无水乙醇中，控制适当物料比，单酚基醚化合物收率在88%以上，二酚基醚化合物收率在95%以上。在无水乙醇中合成了双酚A液体环氧树脂，环氧值为0.4267-0.5324mol/100g，有机氯含量为0.088-0.372%，达到了工业品的技术指标，克服了传统工艺环境污染严重、物料消耗高等缺点。
4.以纳米碳酸钾取代氢氧化钾等强碱，研究了活泼亚甲基化合物与二硫化碳在非水溶剂中的缩合反应，考察了反应的不同影响因素。结果表明，质子性有机溶剂利于反应的进行，底物的结构对反应有显著的影响。在无水乙醇中30-40℃反应，产物烷基化后的产品收率为83-90%，高于强碱法的收率。以异硫氰酸甲酯和硝基甲烷为主要原料，合成了N-甲基-1-甲硫基-2-硝基乙烯胺，产品收率由传统工艺的50%提高到85%。
5.以纳米碳酸钾取代乙醇钠等强碱，研究了非水溶剂中活泼亚甲基化合物的非均相肟化反应，考察了反应的不同影响因素。结果表明，质子性有机溶剂利于反应的进行，底物和反应温度对反应影响显著。在无水乙醇中10-20℃反应，产品收率为81-92%，与乙醇钠法相当，但产物的分离更简单。
The strong base such as sodium ethoxide used widely in organic synthesis industry istrendling to be replaced by carbonate, espectively potassium carbonate due to sodiumethoxide with some disadvantages such as severe corrosion, more side reactions andcomplicated isolation of products. However, due to the weak alkalinity, the potassiumcarbonate participated organic rections usually need high temperature, high pressure, longreaction time and so on. The preparation and application of nano materical in organicsysnthesis have attracted more and more attentions recently due to their unique physical andchemical properties. The preparation and application of nano potassium carbonate inorganic synthesis are rare. In this thesis, the preparation and application of nano-K2CO3inorganic synthesis are studied. The main contents and results are as following:
1. Nano-K2CO3is prepared in the high frequency resonance machine, and effects onmean size of nano-K2CO3are investigated. The results show that mean size of K2CO3prepared by wet grinding method is smaller than that by dry grinding method, and meansize of nano-K2CO3is also affected by solvents. Protonic organic solvents are morefavorable to reduce mean size of micronano-K2CO3. If0.3%of lauric acid compared withthe amount K2CO3was added to solvents, the mean size of nano-K2CO3can be reduced to98nm, which are the size of75%of particles less than100nm. The results also show thatthe alkalinity of nano-K2CO3is strong enough to replace the strong base such as sodiumethoxide to promote the reaction of diethyl malonate and phenyl chloride in protonicorganic solvents.
2. Heterogeneous alkylation reactions of active methylene compounds withhalogenated hydrocarbon are carried out in organic solvents using nano-K2CO3as base, andthe effects on the reaction are investigated. The results show that the reactions are morefavorable in protonic organic solvents, and the reactive activity is affected by the structureof active methylene compounds and halides. For Br, Cl-dihalogenated alkylhalides, activemethylene compounds can selectively react with hydrocarbon bromide. Under50-70℃using nano-K2CO3as base in anhydrous ethanol, monoalkylation product can be preparedwith yield of82-90%, which is higher than that by sodium ethoxide.
3. Heterogeneous Williamson reactions of phenolic compounds such as bisphenol Awith halides are studied in organic solvents using nano-K2CO3as base, and the effects onthe reaction are investigated. The results show that the reactions are more favorable inprotonic organic solvents, and the two hydroxy groups reacts with halides stepwisely,which is different from Williamson reactions promoted by traditional strong alkaline. Themonoalkylation product can be selectively prapared by control the reaction condition. Themono phenol ether can be prepared in yeild of88%under proper ratio of starting material in anhydrous ethanol. And the liquid biphenol A epoxy resin can be produced in the yield of95%. The epoxy value is0.4267-0.5324mol/100g, chloride content is0.088-0.372%, whichis reached the technical spectification of the industical. The disadvantigates such as highermaterial consumption, severe environmental pollution in traditional process are overcomed.
4. Condensation reaction of active methylene compounds with carbon disulfide arestudied in organic solvents using nano-K2CO3as base, and the effects on the reaction areinvestigated. The results show that the reactions are more favorable in protonic organicsolvents, the reactive activity is affected by the structure of active methylene compounds.Under30-40℃in anhydrous ethanol, the yield of alkylated product is82-90%higher thanthat promoted by KOH. N-methyl-1-methylthio-2-nitroethenamine is prepared from methylisothiocyanate and nitromethane as the main raw materials in the yield of85%wich ishigher than that (50%) in traditional process.
5. Heterogeneous oximation reactions of active methylene compounds with ethylnitrite are studied in organic solvents using nano-K2CO3as base, and the effects on thereaction are investigated. The results show that the reactions are more favorable in protonicorganic solvents, and the reactive activity is affected by the structure of active methylenecompounds and reaction temperature. Under10-20℃in anhydrous ethanol, the yield is81-92%, which is higher than that promoted by sodium ethoxide. The isolation of product issimple.
1.采用高频共振研磨机制备纳米碳酸钾，对影响纳米碳酸钾粒径的因素进行了考察。结果表明，湿法研磨比干法研磨制备的碳酸钾粉体粒径更小，质子性有机溶剂利于湿法研磨制备碳酸钾粉体，若加入少量月桂酸，碳酸钾粉体的粒径会进一步降低。在无水乙醇中加入碳酸钾物质的量0.3%的月桂酸，可以制备平均粒径为98nm的纳米碳酸钾，其中小于100nm的纳米碳酸钾颗粒占75%。测试表明，在质子性有机溶剂中纳米碳酸钾表现出较强的碱性，可以取代乙醇钠等强碱促使丙二酸二乙酯与苄基氯进行烃基化反应。
2.以纳米碳酸钾取代乙醇钠等强碱，研究了活泼亚甲基化合物与卤代烃在非水有机溶剂中的烃基化反应，考察了反应的不同影响因素。结果表明，质子性有机溶剂利于反应的进行；不同的底物和卤代烃，反应活性有差异，对于Br,Cl-二卤代烷烃，活泼亚甲基化合物可以与溴代烃发生选择性烃基化反应。在无水乙醇中50-80℃反应，活泼亚甲基化合物的单烃基化产品收率为82-90%，高于乙醇钠法的收率。
3.以纳米碳酸钾取代乙醇钠等强碱，研究了双酚A等二羟基酚类化合物与卤代烃在非水溶剂中的Williamson反应，考察了反应的不同影响因素。结果表明，质子性有机溶剂利于反应的进行，在质子性有机溶剂中双酚A等酚类化合物的两个羟基分步与卤代烃进行反应，与传统强碱法不同。在无水乙醇中，控制适当物料比，单酚基醚化合物收率在88%以上，二酚基醚化合物收率在95%以上。在无水乙醇中合成了双酚A液体环氧树脂，环氧值为0.4267-0.5324mol/100g，有机氯含量为0.088-0.372%，达到了工业品的技术指标，克服了传统工艺环境污染严重、物料消耗高等缺点。
4.以纳米碳酸钾取代氢氧化钾等强碱，研究了活泼亚甲基化合物与二硫化碳在非水溶剂中的缩合反应，考察了反应的不同影响因素。结果表明，质子性有机溶剂利于反应的进行，底物的结构对反应有显著的影响。在无水乙醇中30-40℃反应，产物烷基化后的产品收率为83-90%，高于强碱法的收率。以异硫氰酸甲酯和硝基甲烷为主要原料，合成了N-甲基-1-甲硫基-2-硝基乙烯胺，产品收率由传统工艺的50%提高到85%。
5.以纳米碳酸钾取代乙醇钠等强碱，研究了非水溶剂中活泼亚甲基化合物的非均相肟化反应，考察了反应的不同影响因素。结果表明，质子性有机溶剂利于反应的进行，底物和反应温度对反应影响显著。在无水乙醇中10-20℃反应，产品收率为81-92%，与乙醇钠法相当，但产物的分离更简单。
The strong base such as sodium ethoxide used widely in organic synthesis industry istrendling to be replaced by carbonate, espectively potassium carbonate due to sodiumethoxide with some disadvantages such as severe corrosion, more side reactions andcomplicated isolation of products. However, due to the weak alkalinity, the potassiumcarbonate participated organic rections usually need high temperature, high pressure, longreaction time and so on. The preparation and application of nano materical in organicsysnthesis have attracted more and more attentions recently due to their unique physical andchemical properties. The preparation and application of nano potassium carbonate inorganic synthesis are rare. In this thesis, the preparation and application of nano-K2CO3inorganic synthesis are studied. The main contents and results are as following:
1. Nano-K2CO3is prepared in the high frequency resonance machine, and effects onmean size of nano-K2CO3are investigated. The results show that mean size of K2CO3prepared by wet grinding method is smaller than that by dry grinding method, and meansize of nano-K2CO3is also affected by solvents. Protonic organic solvents are morefavorable to reduce mean size of micronano-K2CO3. If0.3%of lauric acid compared withthe amount K2CO3was added to solvents, the mean size of nano-K2CO3can be reduced to98nm, which are the size of75%of particles less than100nm. The results also show thatthe alkalinity of nano-K2CO3is strong enough to replace the strong base such as sodiumethoxide to promote the reaction of diethyl malonate and phenyl chloride in protonicorganic solvents.
2. Heterogeneous alkylation reactions of active methylene compounds withhalogenated hydrocarbon are carried out in organic solvents using nano-K2CO3as base, andthe effects on the reaction are investigated. The results show that the reactions are morefavorable in protonic organic solvents, and the reactive activity is affected by the structureof active methylene compounds and halides. For Br, Cl-dihalogenated alkylhalides, activemethylene compounds can selectively react with hydrocarbon bromide. Under50-70℃using nano-K2CO3as base in anhydrous ethanol, monoalkylation product can be preparedwith yield of82-90%, which is higher than that by sodium ethoxide.
3. Heterogeneous Williamson reactions of phenolic compounds such as bisphenol Awith halides are studied in organic solvents using nano-K2CO3as base, and the effects onthe reaction are investigated. The results show that the reactions are more favorable inprotonic organic solvents, and the two hydroxy groups reacts with halides stepwisely,which is different from Williamson reactions promoted by traditional strong alkaline. Themonoalkylation product can be selectively prapared by control the reaction condition. Themono phenol ether can be prepared in yeild of88%under proper ratio of starting material in anhydrous ethanol. And the liquid biphenol A epoxy resin can be produced in the yield of95%. The epoxy value is0.4267-0.5324mol/100g, chloride content is0.088-0.372%, whichis reached the technical spectification of the industical. The disadvantigates such as highermaterial consumption, severe environmental pollution in traditional process are overcomed.
4. Condensation reaction of active methylene compounds with carbon disulfide arestudied in organic solvents using nano-K2CO3as base, and the effects on the reaction areinvestigated. The results show that the reactions are more favorable in protonic organicsolvents, the reactive activity is affected by the structure of active methylene compounds.Under30-40℃in anhydrous ethanol, the yield of alkylated product is82-90%higher thanthat promoted by KOH. N-methyl-1-methylthio-2-nitroethenamine is prepared from methylisothiocyanate and nitromethane as the main raw materials in the yield of85%wich ishigher than that (50%) in traditional process.
5. Heterogeneous oximation reactions of active methylene compounds with ethylnitrite are studied in organic solvents using nano-K2CO3as base, and the effects on thereaction are investigated. The results show that the reactions are more favorable in protonicorganic solvents, and the reactive activity is affected by the structure of active methylenecompounds and reaction temperature. Under10-20℃in anhydrous ethanol, the yield is81-92%, which is higher than that promoted by sodium ethoxide. The isolation of product issimple.
引文
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