CN106542945A - 一种以碳酸二甲酯为溶剂光催化氧化醇生成醛的方法 - Google Patents
一种以碳酸二甲酯为溶剂光催化氧化醇生成醛的方法 Download PDFInfo
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Abstract
本发明公开了一种以碳酸二甲酯为溶剂光催化氧化醇生成醛的方法,属于光催化有机合成技术领域,其以碳酸二甲酯为溶剂,在其中通入大量O2后,在以C/TiO2为光催化剂、光照条件下,实现将苯甲醇等醇类化合物光催化氧化成相应的醛。本发明对多种醇类催化氧化为对应的醛均具有良好的转化效率及反应选择性,且其操作简单,适于大规模推广。
Description
技术领域
本发明属于光催化有机合成技术领域,具体涉及一种以碳酸二甲酯为溶剂、C/TiO2为光催化剂光催化氧化醇生成醛的方法。
背景技术
醇催化氧化为醛是一种重要的有机催化反应,适用于各种化学物质的合成。以苯甲醛为例,传统工业生产中有两种不同的合成路径:一种是通过甲苯氯化水解或甲苯氧化获得,其所得产品价格低廉,但是易残留有毒和致癌的物质 (如Cl,F);另一种是通过绿色合成高价值的产物(如苯甲酸甲酯还原法、苯甲醇氧化法),其可直接作为天然化妆品或医学原料,但由于其产量低、能耗高,难以实现广泛的应用。因此,发展一种高效无毒的绿色方法实现醇-醛转化成为当前研究热点。
发明内容
本发明针对现有醇催化氧化为醛转化率低且含有毒物质的问题,提供了一种以碳酸二甲酯为溶剂,高效光催化氧化醇生成醛的方法,
为实现上述目的,本发明采用如下技术方案:
一种以碳酸二甲酯为溶剂光催化氧化醇生成醛的方法,其包括以下步骤:
1)以10-50mL/min的流量向碳酸二甲酯中通入2-10min氧气,使碳酸二甲酯中溶氧量达到饱和;
2)取步骤1)所得碳酸二甲酯0.5-5.5 mL到20 mL石英试管中,加入0.01-2.0 mmol醇类化合物和5-30 mg C/TiO2催化剂,封住石英试管口;
3)在搅拌条件下,将步骤2)所得混合液体于250nm~800nm光线下照射处理1-20h,所得反应液离心取上层清液即得。
其中,优选的,步骤1)中以20 mL/min的流量通入O2 5min;步骤2)中取碳酸二甲酯1.5 mL,加入0.1mmol苯甲醇和16 mg C/TiO2催化剂;步骤3)照射6h。
所用碳酸二甲酯为无水级,纯度≥99%;所用氧气纯度≥99%。
所述醇类化合物包括苯甲醇及其衍生物。
所述C/TiO2催化剂按以下步骤进行制备:
1)将5-30mL钛酸异丙酯分散在5-45 mL异丙醇中,而后滴加到10-50 mL醋酸中,形成乳白液体;
2)将所得液体于10-70℃水浴中搅拌10-40h,得透明溶液;
3)向所得溶液中滴加10-38 mL去离子水,并在常温下继续搅拌1-8h;
4)将溶液转移至100 mL聚四氟乙烯反应釜中,50-150℃水热反应1-8h后自然降温;
5)将产物用去离子水及乙醇清洗后,所得沉淀于30-80℃进行干燥;
6)将干燥后的粉末在马弗炉中80-300℃煅烧3h,得到C/TiO2催化剂。
其中,优选的,步骤1)中将10 mL钛酸异丙酯分散在15 mL异丙醇中,而后滴加到30mL醋酸中;步骤2)中于50℃水浴中搅拌20h;步骤3)中向溶液中滴加18 mL去离子水,并在常温下搅拌4h;步骤4)中100℃水热反应4小时;步骤5)中于60℃烘箱进行干燥;步骤6)中于200℃进行煅烧。
本发明的有益效果在于:本发明以绿色材料C/TiO2为光催化剂,以无毒、低成本、绿色安全、高效的碳酸二甲酯为反应溶剂,在可见光下,实现了醇至醛的高效转化,其方法简单,反应溶剂无毒、低成本、安全、高效,易于推广,且对多种醇类催化氧化为对应的醛有很好的转化效率和选择性,具有显著的经济效益。
具体实施方式
一种以碳酸二甲酯为溶剂光催化氧化醇生成醛的方法,其包括以下步骤:
1)以10-50mL/min的流量向碳酸二甲酯中通入2-10min氧气,使碳酸二甲酯中溶氧量达到饱和;
2)取步骤1)所得碳酸二甲酯0.5-5.5 mL到20 mL石英试管中,加入0.01-2.0 mmol苯甲醇和5-30 mg C/TiO2催化剂,封住石英试管口;
3)在搅拌条件下,将步骤2)所得混合液体于250nm~800nm光线下照射处理1-20h,所得反应液离心取上层清液即得。
所用碳酸二甲酯为无水级,纯度≥99%;所用氧气纯度≥99%。
所述醇类化合物包括苯甲醇及其衍生物。
所用光源为自然光源或人造光源(300W氙灯),波长在250~800nm。
所述C/TiO2催化剂按以下步骤进行制备:
1)将5-30mL钛酸异丙酯分散在5-45 mL异丙醇中,而后滴加到10-50 mL醋酸中,形成乳白液体;
2)将所得液体于10-70℃水浴中搅拌10-40h,得透明溶液;
3)向所得溶液中滴加10-38 mL去离子水,并在常温下继续搅拌1-8h;
4)将溶液转移至100 mL聚四氟乙烯反应釜中,50-150℃水热反应1-8h后自然降温;
5)将产物用去离子水及乙醇清洗后,所得沉淀于30-80℃进行干燥;
6)将干燥后的粉末在马弗炉中80-300℃煅烧3h,得到C/TiO2催化剂。
为了使本发明所述的内容更加便于理解,下面结合具体实施方式对本发明所述的技术方案做进一步的说明,但是本发明不仅限于此。
所用氙灯为PLS-SXE 300,购自北京泊菲莱科技有限公司。
实施例1
C/TiO2催化剂的制备,包括以下步骤
1)将10mL钛酸异丙酯分散在15 mL异丙醇中,而后滴加到30 mL醋酸中,形成乳白液体;
2)将所得液体于50℃水浴中搅拌20h,得透明溶液;
3)向所得溶液中滴加18 mL去离子水,并在常温下继续搅拌4h;
4)将溶液转移至100 mL聚四氟乙烯反应釜中,100℃水热反应4h后自然降温;
5)将产物用去离子水及乙醇清洗后,所得沉淀于60℃进行干燥;
6)将干燥后的粉末在马弗炉中200℃煅烧3h,得到C/TiO2催化剂。
实施例2
不同溶剂中的光催化活性的对比,其实验操作步骤如下
1)按20mL/min的流量分别在反应溶剂(碳酸二甲酯、三氟甲苯、乙腈、甲苯、水)中通入5min O2,使溶剂中溶氧量达到饱和;
2)分别移取1.5 mL上述溶剂至石英试管中,加入0.1 mmol(20.4μL)苯甲醇、16 mg实施例1制得的C/TiO2催化剂,封住石英试管口;
3)以300W氙灯为光源,在光路中加入420 nm和800 nm的两块截止滤波片,以保证出射光谱区间为420 nm~800 nm;
4)在搅拌条件下,将各混合液体于光源下照射6h,所得反应液离心,取上层清液进入气相色谱中进行分析(安捷仑HP7890,FFAP柱),结果见表1。
表1 不同溶剂中光催化活性的对比
由表1结果可知,与毒性溶剂乙腈、甲苯相比,碳酸二甲酯作为反应溶剂具有更高的苯甲醇转化率,且比无毒的水溶剂高。此外,虽然以三氟甲苯为溶剂能获得更高的苯甲醇转化率(80.6%),但基于三氟甲苯的高毒性,确定以碳酸二甲酯为最优的溶剂。
实施例3
C/TiO2催化剂在碳酸二甲酯中催化氧化各类醇至醛的活性
采用实施例2的方法,以碳酸二甲酯为反应溶剂,以链状、杂环、不饱和、单醇、二元醇、多元醇等为反应底物,考察本发明催化氧化反应条件对不同醇类底物的普适性,结果见表2。
表2 C/TiO2催化剂在碳酸二甲酯中催化氧化各类醇至醛的活性
从表2结果可知,以C/TiO2为光催化剂,在碳酸二甲酯溶剂中,能实现各类醇高效转化为相应的醛类,且均具有较高的选择性。
以上所述仅为本发明的较佳实施例,凡依本发明申请专利范围所做的均等变化与修饰,皆应属本发明的涵盖范围。
Claims (5)
1.一种以碳酸二甲酯为溶剂光催化氧化醇生成醛的方法,其特征在于:包括以下步骤:
1)以10-50mL/min的流量向碳酸二甲酯中通入2-10min氧气,使碳酸二甲酯中溶氧量达到饱和;
2)取步骤1)所得碳酸二甲酯0.5-5.5 mL,加入0.01-2.0 mmol醇类化合物和5-30 mgC/TiO2催化剂,封口;
3)在搅拌条件下,将步骤2)所得混合液体于光线下照射处理1-20h,所得反应液离心取上层清液即得。
2.根据权利要求1所述以碳酸二甲酯为溶剂光催化氧化醇生成醛的方法,其特征在于:所用碳酸二甲酯为无水级,纯度≥99%;所用氧气纯度≥99%。
3.根据权利要求1所述以碳酸二甲酯为溶剂光催化氧化醇生成醛的方法,其特征在于:所述醇类化合物包括苯甲醇及其衍生物。
4.根据权利要求1所述以碳酸二甲酯为溶剂光催化氧化醇生成醛的方法,其特征在于:所述C/TiO2催化剂按以下步骤进行制备:
1)将5-30mL钛酸异丙酯分散在5-45 mL异丙醇中,而后滴加到10-50 mL醋酸中,形成乳白液体;
2)将所得液体于10-70℃水浴中搅拌10-40h,得透明溶液;
3)向所得溶液中滴加10-38 mL去离子水,并在常温下继续搅拌1-8h;
4)将溶液转移至聚四氟乙烯反应釜中,50-150℃水热反应1-8h后自然降温;
5)将产物用去离子水及乙醇清洗后,所得沉淀于30-80℃进行干燥;
6)将干燥后的粉末在马弗炉中80-300℃煅烧3h,得到C/TiO2催化剂。
5.根据权利要求1所述以碳酸二甲酯为溶剂光催化氧化醇生成醛的方法,其特征在于:所述光线的波长为250nm~800nm。
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CN115722270A (zh) * | 2022-11-28 | 2023-03-03 | 东南大学 | 一种核壳结构的PI-TiO2催化剂的制备方法及其应用 |
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CN115722270A (zh) * | 2022-11-28 | 2023-03-03 | 东南大学 | 一种核壳结构的PI-TiO2催化剂的制备方法及其应用 |
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