CN109174159B - 一种定点加氘光催化剂 - Google Patents
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Abstract
本发明涉及一种光催化剂,其由金属催化剂和半导体催化剂组成,所述半导体催化剂包括无机半导体催化剂和有机半导体催化剂。本发明以更环保、廉价的氘水或氘代试剂作氘源来代替氘气,在光催化的作用下实现对烯烃类或炔烃类化合物的定点氘化反应。本发明提供的光催化剂催化的氘化反应较传统的氘化反应具有更高的选择性、更温和的反应条件以及更经济适用性,适合用于大规模氘代化学品生产。
Description
技术领域
本发明涉及光催化制备化学品领域,具体涉及一种实现碳碳不饱和键的定点氘化的光催化剂。
背景技术
氘代化学品是一类特殊化合物,在反应机理研究、动力学、药物代谢和生物结构测定等领域都有重要应用。氢的重同位素(氘或氚)通常是通过多步合成引入目标化合物。目前常用的氢氘交换反应是一种非常有吸引力的策略,然而该方法面临巨大的挑战。一方面氢氘交换反应常以氘气为氘源,绝大多数过程涉及高温、高压、强酸、强碱条件;另一方面氢氘交换反应的选择性难以控制,很难实现对氘代产物关键位点进行定点氘代。因此,现有的氘化策略和技术有待进一步改进和发展。
发明内容
相对于氢氘交换催化反应,定点氘化技术具有更高的选择性和氘化效率。通过选择不同类型的加氘或氘解催化剂,可以实现对不同官能团和位点的可控氘化,因此可以作为更为理想的氘化策略。
本发明提供了一种实现碳碳不饱和键的定点氘化的光催化剂,目的在于利用光解氘源过程产生具有高活性的氘中间体,结合碳碳不饱和键加氘技术,在常温常压可见光条件下实现对碳碳不饱和键实现定点氘化。旨在解决传统加氘反应需要用到氘气、高温、高压条件、选择性不高等关键问题。利用该过程可以获得一系列具有高附加值的氘代化学品,反应需求能耗低、产物选择性高、分离简单、污染物排放少,符合国家节能减排政策,具有广阔的工业应用前景。
本发明的技术方案如下:一种新型光催化剂,所述光催化剂由金属催化剂和有机半导体催化剂组成;所述金属催化剂与有机半导体催化剂的质量比为 1:10~1:200。
优选的,所述金属催化剂包括Pd、Pt或Au。
优选的,所述有机半导体催化剂为氮化碳。
优选的,所述光催化剂为Pd/PCN、Pt/PCN、Au/PCN。
更优选的,所述Pd/PCN光催化剂中Pd与PCN的质量比为1:10至1:100。
另一方面,本发明的光催化剂可用于催化氢化或氘化烯烃类或炔烃类化合物。
本发明中“烯烃类化合物”包含链状烯烃和环内烯烃,其中环内烯烃不涉及芳香环。
本发明的催化剂催化氢化或氘化烯烃类或炔烃类化合物,其反应过程中产生具有高活性的氢或氘中间体,而不产生氢气或氘气;反应条件温和,后处理简单,氢化或氘化收率高,取得了较好的技术效果。
本发明以氘水等安全清洁氘源来代替氘气作为氘源,实现了温和条件下对特定的碳碳不饱和键的定点氘化。
附图说明
图1为光催化剂A的X射线衍射图。
图2为光催化剂A的透射电镜图。
图3为光催化剂A的Pd成份的X射线光电子能谱图。
图4为光催化剂A的产氢性能图。
具体实施方式
本发明提供一种新型光催化剂,为使本发明的目的、技术方案及效果更加清楚、明确,以下对本发明进一步详细说明。应当理解,此处所描述的具体实施例仅用以解释本发明,并不用于限定本发明。
下面通过实施例对本发明进行详细说明。
(1)光催化剂的制备
a.光催化剂A的制备
其制备的方法如下:
将2g三聚氰胺与20g溴化钾混合均匀并研磨5分钟,转移至氧化铝陶瓷坩埚,并放置于管式炉内,设置焙烧程序,升温至550℃焙烧2小时。自然冷却至室温,所得的黄色固体分散在200mL、80℃的热水中,搅拌30分钟后趁热过滤,用去离子水清洗3次。所得氮化碳固体在80度烘箱内干燥24小时备用。
取0.3g上述氮化碳固体,分散于80mL去离子水中,并加入20mL乙二醇溶液,搅拌超声2小时。用移液器向所得的混合液体中加入28μL、1mol/L的氯钯酸溶液,在500W氙灯光照下反应1小时。所得的混合溶液经离心后,置于在80度的烘箱干燥24小时,得到Pd/PCN光催化剂,Pd与PCN的质量比为1:100。
制得的负载Pd的PCN光催化剂的表征见图1~图4所示。其中,图1为Pd/PCN 的X射线衍射图。图2为Pd/PCN的透射电镜图。图3为光催化剂中Pd成份的 X射线光电子能谱图。图4为光催化剂Pd/PCN的产氢性能图。
图1Pd/PCN的X射线衍射图的检测方法如下:日本理学x射线多晶衍射仪 UltimaIV,40kV,40mA,Cu Ka靶,0.1o min-1。
b.光催化剂B的制备
采用a中所述的方法,可制备得到Pd/PCN光催化剂,Pd与PCN的质量比为1:10。
(2)碳碳不饱和键的光催化定点氘化
实施例1:苯乙烯的光催化加氢反应
分别称取0.1mmol苯乙烯、0.1mmol AlCl3、10.0mg光催化剂A加入到5mL 反应瓶中,并加入乙酸乙酯/水/甲醇(2mL/1.5mL/1.5mL)的混合溶液,将反应体系置换为氩气保护状态,然后将反应瓶置于420nm光源下光照反应4小时,反应结束后移走光源,将反应混合物用5.0mL CH2Cl2萃取,萃取液用无水硫酸钠干燥,浓缩得到无色液体。进行GC-MS分析,并结合目标产物的标准曲线确定该反应的收率。
按照同样的合成方法,其他化合物可以催化加氢得到相应的氢化产物,具体见表1。
表1化合物催化加氢反应结果
实施例14:以氘水为氘源,光催化(E)-1,2-二苯乙烯加氘制备氘化化学品
分别称取0.1mmol(E)-1,2-二苯乙烯、0.1mmol AlCl3、10.0mg光催化剂 A加入到5mL反应瓶中,并用注射器加入乙酸乙酯/氘水/氘代甲醇(2mL/1.5 mL/1.5mL)的混合溶液,将反应体系置换为氩气保护状态,然后将反应瓶置于 420nm光源下光照反应4.0小时,反应结束后移走光源,将反应混合物用CH2Cl2 (5.0mL×3)萃取,合并有机相,用无水硫酸钠干燥,真空脱溶剂,柱层析分离得目标产物。所得产物经GC-MS,HRMS,1HNMR,C-NMR,FT-IR等测试确定结构。
按照同样的合成方法,可以催化加氘得到相应的氘化产物,具体见表2。
表2化合物催化加氘反应结果
实施例18光催化剂B催化苯乙烯的加氢反应
分别称取0.1mmol苯乙烯、0.1mmol AlCl3、10.0mg光催化剂B加入到5mL 反应瓶中,并加入乙酸乙酯/水/甲醇(2mL/1.5mL/1.5mL)的混合溶液,将反应体系置换为氩气保护状态,然后将反应瓶置于420nm光源下光照反应2小时,反应结束后移走光源,将反应混合物用5.0mL CH2Cl2萃取,萃取液用无水硫酸钠干燥,浓缩得到无色液体(10.6mg,100%)。
综上所述,本发明提供一种新型光催化剂,使用了温和及廉价的氘源来代替氘气,实现高选择性的特定官能团定点加氘反应,解决了现有加氘反应方案中使用氘气、反应条件苛刻、选择性不高等问题。由于反应条件更加温和,本发明的新型催化剂可氘化一系列化学品,具有氘化位点和个数可控、可调等优势,可降低氘代化学品制备成本,使其广泛应用于反应机理研究、动力学研究、药物代谢标定、生物分子标记等。
应当理解的是,本发明的应用不限于上述的举例,对本领域普通技术人员来说,可以根据上述说明加以改进或变换,所有这些改进和变换都应属于本发明所附权利要求的保护范围。
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