钨催化功能化合物的合成及在有机氧化反应中的应用研究
摘要
烯烃环氧化和醇的氧化反应是化学工业生产,特别是精细化工中常见的有机氧化反应。催化剂的选择直接关系到反应速度的快慢、产率的多少和选择性的好坏并最终决定一个反应单元或工艺能否工业化。于是,设计合成结构新颖、反应活性强、选择性高、易回收、成本低的催化剂成为氧化领域一项重要研究工作。该研究是本团队国家自然科学基金项目中的一个分支,在其它研究组对稀散金属铼的新型化合物催化功能及所应用的反应体系有较系统研究基础上,按项目设计内容分别对同为稀有金属并具催化功能的钨相关化合物进行了研究。工作重点在设计合成钨催化功能化合物并应用在铼己成功催化的烯烃环氧化反应体系中并评价比较其催化性能。该研究内容不仅丰富了有机化学反应所需的催化剂储备,同时也丰富了钨化学研究的内容。具有良好的科学意义及实际应用价值。
本文合成四类17种未见报道的钨酸盐化合物并把它们分别作为烯烃环氧化和醇的氧化反应催化剂使用,结果表明,所有化合物分别在不同反应体系中表现出良好的催化效果,可作为催化材料使用。具体研究内容如下：
1、成功合成钨的季铵盐离子液体[(CH3)N(n-C8H17)3]2W2O11,用红外、核磁氢谱等表征手段确定离子液体结构。用单因素和正交试验相结合的分析方法考察了[(CH3)N(n-C8H17)3]2W2O11/UHP/乙腈的反应体系,分别得到环辛烯、环己烯、1-己烯、苯乙烯和1-苯基环己烯环氧化的催化效果,结果表明,该化合物对环辛烯、环己烯环氧化的催化效果较好,对其它烯烃有催化作用但产率不高。
2、以不同长度碳链N-甲基吗啉溴盐与钨酸钠反应合成五种新型N-甲基吗啉过氧钨酸盐([Mor1,n]NaW2O11(n=2,4,5,8,10)),用红外、核磁氢谱等表征手段,确定化合物结构。用单因素和正交试验相结合的分析方法重点考察以N-甲基吗啉钨酸盐为催化剂的反应体系,即[Mor1,5]NaW2O11/UHP/乙腈反应体系对环辛烯、环己烯、苯乙烯、1-甲基环己烯和1-苯基环己烯环环氧化催化效果,结果表明,该体系对环辛烯、环己烯催化效果较好,对其它烯烃较弱。
3、以不同长度碳链的喹啉溴盐与钨酸钠反应合成四种新型喹啉过氧钨酸盐化合物([Quin]2W2O11(n=2,4,5,8)),用红外、核磁氢谱等表征手段,确定化合物结构。用单因素和正交试验相结合的分析方法重点考察在以喹啉过氧钨酸盐为催化剂的反应体系,即[Qui4]2W2O11/UHP/乙腈反应体系对环辛烯和环己烯环氧化的催化效果,结果表明,对环辛烯环氧化的催化效果较好,对环己烯较弱。
4、以不同碳链长度的N-甲基吗啉溴盐与钨酸钠反应合成四种新型的N-甲基吗啉十聚钨酸盐([Mor1,n]4W10O32(n=2,5,8,10),用红外、核磁氢谱等表征手段,确定化合物的结构。用单因素和正交试验相结合的分析方法重点考察在以N-甲基吗啉十聚钨酸盐为催化剂的反应体系,即[Mor1,2]4W10O32/UHP/乙腈/的/反应体系对环辛烯、环己烯、苯乙烯、1-甲基环己烯和1-苯基环己烯环氧化催化效果,结果表明,该体系对环辛烯、环己烯催化效果较好,对其它烯烃有催化作用,但产率不高。
5、以不同碳链长度的喹啉溴盐与钨酸钠反应合成四种新型喹啉十聚钨酸盐([Quin]4W10O32(n=2,4,5,8),用红外、核磁氢谱等表征手段,确定化合物的结构。用单因素和正交试验相结合的分析方法重点考察以喹啉十聚钨酸盐为催化剂的反应体系,即[Qui4]W10032/UHP/乙腈反应体系,结果表明,此化合物对环己烯和环辛烯的催化环氧化效果均较好。
6、考察以季铵盐W2011功能化合物和N-甲基吗啉十聚钨酸盐为催化剂在醇氧化反应体系中的应用,即N-甲基吗啉十聚钨酸盐/H202和[(CH3)N(n-C8H17)3]2W2O11/H2O2两种体系对环己醇、苯甲醇等不同醇的催化氧化效果,并通过单因素和正交试验相结合的分析方法确定最佳反应条件。结果表明,季铵盐W2011功能化合物和N-甲基吗啉十聚钨酸盐在该反应体系中对环己醇、苯甲醇等多数醇都有很好的氧化催化作用。
7、通过实验结果比较、总结归纳,发现钨催化功能化合物在烯烃环氧化过程中几点全新、重要的反应规律。即：当钨酸盐的阴离子为[W2011]2-时,选择不同种类阳离子(N-甲基吗啉、喹啉)对环辛烯环氧化产率影响不大,但是催化剂阳离子为喹啉使环己烯的环氧化的产率有所降低；当钨酸盐的阴离子为[W10032]4-时,选择不同种类阳离子(N-甲基吗啉、喹啉)对环辛烯产率影响依然不大,但是催化剂选择喹啉阳离子时环己烯的环氧化产率要好于N-甲基吗啉为阳离子；总体来说环辛烯和环己烯的催化环氧化产率,催化剂阴离子为[W10032]4-要好于[W2011]2-。
Olefin epoxidation reaction and alcohol oxidation reaction are the most common organic catalytic reactions which are used in the industrial production and in fine chemical industry. In these reactions, the selection of catalyst determines the rate, yield and selectivity of reaction. Then, it is a challenging task to design a catalyst which has high activity, high selectivity and recyclability in the field of catalytic oxidation. In recent years, polyoxometalates is widely applied in many fields, such as medicine chemistry, catalytic chemistry, materials chemistry, and has exhibited good catalytic activity and application prospect especially in the catalytic oxidation reaction.
The contents of this paper are as follows:
1. An ionic liquid peroxotungstate [(CH3)N(C8H17)3]2W2O11was synthesized and characterized by infrared spectroscopy,1H-NMR and so on. The results showed that they were pure. And then, the ionic liquid was used as catalyst to catalyze epoxidation of olefin. The single factor analysis method and the orthogonal experiment method are used to determine the best reaction conditions.
2. Five new peroxotungstates ([Mor1,n]NaW2O11(n=2,4,5,8,10)) were synthesized and characterized by infrared spectroscopy,'H-NMR and so on. The results showed that they were pure. And then, the new tungstate was used as catalyst to catalyze epoxidation of olefin. The single factor analysis method and the orthogonal experiment method were used to determine the best reaction conditions.
3. Four new peroxotungstates ([Quin]2W2O11(n=2,4,5,8)) were synthesized and characterized by infrared spectroscopy,1H-NMR and so on. The results showed that they were pure. And then, the new tungstate was used as catalyst to catalyze epoxidation of olefin. The single factor analysis method and the orthogonal experiment method were used to determine the best reaction conditions.
4. Four new decatungstates ([Mor1,n]4W10O32(n=2,5,8,10) were synthesized and characterized by infrared spectroscopy, H-NMR and so on. The results showed that they were pure. And then, the new tungstate was used as catalyst to catalyze epoxidation of olefin. The single factor analysis method and the orthogonal experiment method to were used to determine the best reaction conditions.
5. Four new decatungstates ([Quin]4Wio032(n=2,4,5,8) were synthesized and characterized by infrared spectroscopy,'H-NMR and so on. The results showed that they were pure. And then, the new tungstate was used as catalyst to catalyze epoxidation of olefin. The single factor analysis method and the orthogonal experiment method were used to determine the best reaction conditions.
6. Experiment shows that the system has good catalytic effect on oxidation of alcohol with H2O2as oxidant and ionic liquid or decatungstates as catalyst. We used the single factor analysis method and the orthogonal experiment method to determine the best reaction conditions.
7. Finally, the catalytic effects of the above-listed systems of epoxidation of olefin with different polyoxomet-alates as catalyst are compared.
本文合成四类17种未见报道的钨酸盐化合物并把它们分别作为烯烃环氧化和醇的氧化反应催化剂使用,结果表明,所有化合物分别在不同反应体系中表现出良好的催化效果,可作为催化材料使用。具体研究内容如下：
1、成功合成钨的季铵盐离子液体[(CH3)N(n-C8H17)3]2W2O11,用红外、核磁氢谱等表征手段确定离子液体结构。用单因素和正交试验相结合的分析方法考察了[(CH3)N(n-C8H17)3]2W2O11/UHP/乙腈的反应体系,分别得到环辛烯、环己烯、1-己烯、苯乙烯和1-苯基环己烯环氧化的催化效果,结果表明,该化合物对环辛烯、环己烯环氧化的催化效果较好,对其它烯烃有催化作用但产率不高。
2、以不同长度碳链N-甲基吗啉溴盐与钨酸钠反应合成五种新型N-甲基吗啉过氧钨酸盐([Mor1,n]NaW2O11(n=2,4,5,8,10)),用红外、核磁氢谱等表征手段,确定化合物结构。用单因素和正交试验相结合的分析方法重点考察以N-甲基吗啉钨酸盐为催化剂的反应体系,即[Mor1,5]NaW2O11/UHP/乙腈反应体系对环辛烯、环己烯、苯乙烯、1-甲基环己烯和1-苯基环己烯环环氧化催化效果,结果表明,该体系对环辛烯、环己烯催化效果较好,对其它烯烃较弱。
3、以不同长度碳链的喹啉溴盐与钨酸钠反应合成四种新型喹啉过氧钨酸盐化合物([Quin]2W2O11(n=2,4,5,8)),用红外、核磁氢谱等表征手段,确定化合物结构。用单因素和正交试验相结合的分析方法重点考察在以喹啉过氧钨酸盐为催化剂的反应体系,即[Qui4]2W2O11/UHP/乙腈反应体系对环辛烯和环己烯环氧化的催化效果,结果表明,对环辛烯环氧化的催化效果较好,对环己烯较弱。
4、以不同碳链长度的N-甲基吗啉溴盐与钨酸钠反应合成四种新型的N-甲基吗啉十聚钨酸盐([Mor1,n]4W10O32(n=2,5,8,10),用红外、核磁氢谱等表征手段,确定化合物的结构。用单因素和正交试验相结合的分析方法重点考察在以N-甲基吗啉十聚钨酸盐为催化剂的反应体系,即[Mor1,2]4W10O32/UHP/乙腈/的/反应体系对环辛烯、环己烯、苯乙烯、1-甲基环己烯和1-苯基环己烯环氧化催化效果,结果表明,该体系对环辛烯、环己烯催化效果较好,对其它烯烃有催化作用,但产率不高。
5、以不同碳链长度的喹啉溴盐与钨酸钠反应合成四种新型喹啉十聚钨酸盐([Quin]4W10O32(n=2,4,5,8),用红外、核磁氢谱等表征手段,确定化合物的结构。用单因素和正交试验相结合的分析方法重点考察以喹啉十聚钨酸盐为催化剂的反应体系,即[Qui4]W10032/UHP/乙腈反应体系,结果表明,此化合物对环己烯和环辛烯的催化环氧化效果均较好。
6、考察以季铵盐W2011功能化合物和N-甲基吗啉十聚钨酸盐为催化剂在醇氧化反应体系中的应用,即N-甲基吗啉十聚钨酸盐/H202和[(CH3)N(n-C8H17)3]2W2O11/H2O2两种体系对环己醇、苯甲醇等不同醇的催化氧化效果,并通过单因素和正交试验相结合的分析方法确定最佳反应条件。结果表明,季铵盐W2011功能化合物和N-甲基吗啉十聚钨酸盐在该反应体系中对环己醇、苯甲醇等多数醇都有很好的氧化催化作用。
7、通过实验结果比较、总结归纳,发现钨催化功能化合物在烯烃环氧化过程中几点全新、重要的反应规律。即：当钨酸盐的阴离子为[W2011]2-时,选择不同种类阳离子(N-甲基吗啉、喹啉)对环辛烯环氧化产率影响不大,但是催化剂阳离子为喹啉使环己烯的环氧化的产率有所降低；当钨酸盐的阴离子为[W10032]4-时,选择不同种类阳离子(N-甲基吗啉、喹啉)对环辛烯产率影响依然不大,但是催化剂选择喹啉阳离子时环己烯的环氧化产率要好于N-甲基吗啉为阳离子；总体来说环辛烯和环己烯的催化环氧化产率,催化剂阴离子为[W10032]4-要好于[W2011]2-。
Olefin epoxidation reaction and alcohol oxidation reaction are the most common organic catalytic reactions which are used in the industrial production and in fine chemical industry. In these reactions, the selection of catalyst determines the rate, yield and selectivity of reaction. Then, it is a challenging task to design a catalyst which has high activity, high selectivity and recyclability in the field of catalytic oxidation. In recent years, polyoxometalates is widely applied in many fields, such as medicine chemistry, catalytic chemistry, materials chemistry, and has exhibited good catalytic activity and application prospect especially in the catalytic oxidation reaction.
The contents of this paper are as follows:
1. An ionic liquid peroxotungstate [(CH3)N(C8H17)3]2W2O11was synthesized and characterized by infrared spectroscopy,1H-NMR and so on. The results showed that they were pure. And then, the ionic liquid was used as catalyst to catalyze epoxidation of olefin. The single factor analysis method and the orthogonal experiment method are used to determine the best reaction conditions.
2. Five new peroxotungstates ([Mor1,n]NaW2O11(n=2,4,5,8,10)) were synthesized and characterized by infrared spectroscopy,'H-NMR and so on. The results showed that they were pure. And then, the new tungstate was used as catalyst to catalyze epoxidation of olefin. The single factor analysis method and the orthogonal experiment method were used to determine the best reaction conditions.
3. Four new peroxotungstates ([Quin]2W2O11(n=2,4,5,8)) were synthesized and characterized by infrared spectroscopy,1H-NMR and so on. The results showed that they were pure. And then, the new tungstate was used as catalyst to catalyze epoxidation of olefin. The single factor analysis method and the orthogonal experiment method were used to determine the best reaction conditions.
4. Four new decatungstates ([Mor1,n]4W10O32(n=2,5,8,10) were synthesized and characterized by infrared spectroscopy, H-NMR and so on. The results showed that they were pure. And then, the new tungstate was used as catalyst to catalyze epoxidation of olefin. The single factor analysis method and the orthogonal experiment method to were used to determine the best reaction conditions.
5. Four new decatungstates ([Quin]4Wio032(n=2,4,5,8) were synthesized and characterized by infrared spectroscopy,'H-NMR and so on. The results showed that they were pure. And then, the new tungstate was used as catalyst to catalyze epoxidation of olefin. The single factor analysis method and the orthogonal experiment method were used to determine the best reaction conditions.
6. Experiment shows that the system has good catalytic effect on oxidation of alcohol with H2O2as oxidant and ionic liquid or decatungstates as catalyst. We used the single factor analysis method and the orthogonal experiment method to determine the best reaction conditions.
7. Finally, the catalytic effects of the above-listed systems of epoxidation of olefin with different polyoxomet-alates as catalyst are compared.
引文
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