CN108745413A - 一类醌式结构化合物在可见光降解双酚a中的应用 - Google Patents
一类醌式结构化合物在可见光降解双酚a中的应用 Download PDFInfo
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Abstract
本发明提供了一类醌式结构化合物在可见光降解双酚A中的应用，该类化合物具有较窄的光学带隙，吸收光谱拓展到近红外区；本发明提供了该类化合物作催化剂和过氧化氢溶液降解水溶液中双酚A的方法。通过调节pH值和过氧化氢加入体积，催化剂在120分钟时对0.04 mM的双酚A降解率达到98%。本发明制备的催化剂具有操作简单、易分离和循环稳定性好等优点，避免了复合材料的形貌难控制和重现性差的问题，为环境中双酚A的降解提供了新的材料，也为有机光电材料在环境净化领域的研究提供了新的思路。
Description
技术领域
本发明属于有机共轭小分子合成及环境净化领域，涉及一类醌式结构化合物在可见光降解双酚A中的应用。
背景技术
2，2-二（4-羟基苯基）丙烷（Bisphenol A，又称双酚A 或BPA），主要用于制备环氧树脂、聚碳酸酯等多种高分子材料，可作增塑剂、阻燃剂、橡胶防老剂等精细化工产品。双酚A具有类似雌激素功能，容易使雌性早熟，还具有一定的毒性和致畸性。尤其是塑料奶瓶等塑料制品中的双酚A可能会影响婴幼儿的成长发育。因此存在于塑料、医疗器械和食品包装袋中双酚A的降解已经成为研究热点之一。目前去除双酚A的主要方法有物理吸附法、微生物降解法和光催化降解法。物理吸附法主要是通过吸附质和吸附剂分子间作用力实现，这类方法属于可逆性吸附，并没有实现双酚A完全的去除（Kongyin Zhao, Ind. Eng. Chem. Res., 2017, 56, 2549–2556）。微生物降解法处理双酚A是一种简便、高效的处理方法，但也面临着部分降解菌类活性较低的问题（Shengquan Zeng, Bioprocess Biosyst Eng.,2017, 40, 1237–1245）。光催化降解法具有强氧化性、去除率高等优点而引起人们的关注，目前研究较多的TiO2、ZnO等纳米级的催化剂通常会因为量子尺寸效应使吸收光谱蓝移，存在着可见光利用率低和量子效率低的缺点。针对以上问题，科研工作者们提出染料光敏化、掺杂、负载等策略进行优化改性。虽然这些策略在很大程度上提高了催化剂的吸光性能，如Zhu报道了TCNQ和PTCDI通过π-π的相互作用制备复合的有机可见光催化剂降解双酚A，但是复合材料也有重现性较差、需要精密的控制形貌和催化剂容易分离不稳定等缺点。因此需要寻求一种充分利用可见光的半导体材料作催化剂，简便地降解双酚A。
发明内容
本发明的目的在于提供一类醌式结构化合物在可见光降解双酚A中的应用。
本发明提供的一类吡咯并吡咯二酮骨架的醌式结构化合物，其结构如式I所示，标记为DPPMDPC6。
式1
本发明提供的制备式I所示的化合物DPPMDPC6的方法参考文献（Chem. Mater.2015,27, 4719）。
本发明所述的一类醌式结构化合物在可见光降解双酚A中的应用， DPPMDP作催化剂在光降解双酚A中的实验方法如下：
2 mg催化剂和一定体积的过氧化氢（质量分数30 %）置于反应瓶中，加入100 mL不同物质量浓度的双酚A水溶液，采用0.1 mol/L的盐酸溶液与0.1 mol/L的NaOH溶液调节溶液pH，将装置置于光催化反应仪中，未开灯前为暗室，剧烈搅拌待催化剂分散均匀，此时取第一个样品标记双酚A的初始浓度C0。打开250 W氙灯光源（波长为420 nm-750 nm）并计时，分别在30 min，60 min，90 min和120 min各取样一次，悬浮液经过0.45 um尼龙滤膜除去催化剂后，滤液经高效液相色谱分析检测双酚A的去除率。
双酚A降解率（%）＝（初始浓度-残留浓度）/初始浓度×100 %。具体参数条件：取2mL反应液，经0.45 μm滤膜过滤后进行色谱分析，色谱柱为C18(4.6× 150 mm，5 μm)，UV检测器，波长278 nm，柱温32 ℃，流动相甲醇:水＝70:30（v/v），流速为1 mL/min，进样体积25 μL。
本发明所述过氧化氢加入体积为0.05～0.40 mL，其中优选0.20 mL；
本发明所述双酚A水溶液的初始浓度为0.04～1.0 mM，其中优选0.04 mM；
本发明所述双酚A水溶液的pH值为2～11，其中优选pH = 5
本发明提供了一类醌式结构化合物在可见光降解双酚A中的应用，该类化合物具有较窄的光学带隙，吸收光谱拓展到近红外区；本发明提供了该类化合物作催化剂和过氧化氢溶液降解水溶液中双酚A的方法。通过调节pH值和过氧化氢加入体积，催化剂在120分钟时对0.04 mM的双酚A降解率达到98%。本发明制备的催化剂具有操作简单、易分离和循环稳定性好等优点，避免了复合材料的形貌难控制和重现性差的问题，为环境中双酚A的降解提供了新的材料，也为有机光电材料在环境净化领域的研究提供了新的思路。
附图说明
本发明共有7幅附图：
图1为化合物DPPMDPC6的核磁共振氢谱；
图2为化合物DPPMDPC6的核磁共振碳谱；
图3为溶液pH为5时双酚A降解效率；
图4为不同双酚A初始浓度随时间的降解效率曲线；
图5为催化剂进行5次循环实验后降解效率；
图6为化合物DPPMDPC6在溶液状态的紫外-可见吸收光谱；
图7为催化作用下双酚A降解效率。
具体实施方式
为了使本发明的技术手段更易于了解，下面结合具体实施例进一步进行描述，但本发明的实施方式不限于此。
实施例1
准确称取2 mg催化剂和量取0.20 mL的过氧化氢（质量分数30 %）置于反应瓶中，加入100 mL物质的量浓度为0.04 mM的双酚A水溶液，采用0.1 mol/L的盐酸溶液调节溶液pH值为2，将装置置于光催化反应仪中，未开灯前为暗室，剧烈搅拌待催化剂分散均匀，此时取第一个样品标记双酚A的初始浓度C0。打开250 W氙灯光源（波长为420 nm-750 nm）并计时，分别在30 min，60 min，90 min和120 min各取样一次，悬浮液经过0.45 um尼龙滤膜除去催化剂后，滤液经高效液相色谱分析测得在120 min时双酚A的降解率为84%。
实施例2
准确称取2 mg催化剂和量取0.20 mL的过氧化氢（质量分数30 %）置于反应瓶中，加入100 mL物质的量浓度为0.04 mM的双酚A水溶液，采用0.1 mol/L的盐酸溶液调节溶液pH值为5，将装置置于光催化反应仪中，未开灯前为暗室，剧烈搅拌待催化剂分散均匀，此时取第一个样品标记双酚A的初始浓度C0。打开250 W氙灯光源（波长为420 nm-750 nm）并计时，分别在30 min，60 min，90 min和120 min各取样一次，悬浮液经过0.45 um尼龙滤膜除去催化剂后，滤液经高效液相色谱分析测得在120 min时双酚A的降解率为98%，结果如图3所示。
实施例3
准确称取2 mg催化剂和量取0.20 mL的过氧化氢（质量分数30 %）置于反应瓶中，加入100 mL物质的量浓度为0.04 mM的双酚A水溶液，采用0.1 mol/L的NaOH溶液调节溶液pH值为9，将装置置于光催化反应仪中，未开灯前为暗室，剧烈搅拌待催化剂分散均匀，此时取第一个样品标记双酚A的初始浓度C0。打开250 W氙灯光源（波长为420 nm-750 nm）并计时，分别在30 min，60 min，90 min和120 min各取样一次，悬浮液经过0.45 um尼龙滤膜除去催化剂后，滤液经高效液相色谱分析测得在120 min时双酚A的降解率为69%。
实施例4
准确称取2 mg催化剂和量取0.20 mL的过氧化氢（质量分数30 %）置于反应瓶中，加入100 mL物质的量浓度为0.04 mM的双酚A水溶液，采用0.1 mol/L的NaOH溶液调节溶液pH值为11，将装置置于光催化反应仪中，未开灯前为暗室，剧烈搅拌待催化剂分散均匀，此时取第一个样品标记双酚A的初始浓度C0。打开250 W氙灯光源（波长为420 nm-750 nm）并计时，分别在30 min，60 min，90 min和120 min各取样一次，悬浮液经过0.45 um尼龙滤膜除去催化剂后，滤液经高效液相色谱分析测得在120 min时双酚A的降解率为55%。
实施例5
准确称取2 mg催化剂和量取0.05 mL的过氧化氢（质量分数30 %）置于反应瓶中，加入100 mL物质的量浓度为0.04 mM的双酚A水溶液，采用0.1 mol/L的盐酸溶液调节溶液pH值为5，将装置置于光催化反应仪中，未开灯前为暗室，剧烈搅拌待催化剂分散均匀，此时取第一个样品标记双酚A的初始浓度C0。打开250 W氙灯光源（波长为420 nm-750 nm）并计时，分别在30 min，60 min，90 min和120 min各取样一次，悬浮液经过0.45 um尼龙滤膜除去催化剂后，滤液经高效液相色谱分析测得在120 min时双酚A的降解率为75%。
实施例6
准确称取2 mg催化剂和量取0.10 mL的过氧化氢（质量分数30 %）置于反应瓶中，加入100 mL物质的量浓度为0.04 mM的双酚A水溶液，采用0.1 mol/L的盐酸溶液调节溶液pH值为5，将装置置于光催化反应仪中，未开灯前为暗室，剧烈搅拌待催化剂分散均匀，此时取第一个样品标记双酚A的初始浓度C0。打开250 W氙灯光源（波长为420 nm-750 nm）并计时，分别在30 min，60 min，90 min和120 min各取样一次，悬浮液经过0.45 um尼龙滤膜除去催化剂后，滤液经高效液相色谱分析测得在120 min时双酚A的降解率为82%。
实施例7
准确称取2 mg催化剂和量取0.40 mL的过氧化氢（质量分数30 %）置于反应瓶中，加入100 mL物质的量浓度为0.04 mM的双酚A水溶液，采用0.1 mol/L的盐酸溶液调节溶液pH值为5，将装置置于光催化反应仪中，未开灯前为暗室，剧烈搅拌待催化剂分散均匀，此时取第一个样品标记双酚A的初始浓度C0。打开250 W氙灯光源（波长为420 nm-750 nm）并计时，分别在30 min，60 min，90 min和120 min各取样一次，悬浮液经过0.45 um尼龙滤膜除去催化剂后，滤液经高效液相色谱分析测得在120 min时双酚A的降解率为87%。
实施例8
准确称取2 mg催化剂和量取0.20 mL的过氧化氢（质量分数30 %）置于反应瓶中，加入100 mL物质的量浓度为0.08 mM的双酚A水溶液，采用0.1 mol/L的盐酸溶液调节溶液pH值为5，将装置置于光催化反应仪中，未开灯前为暗室，剧烈搅拌待催化剂分散均匀，此时取第一个样品标记双酚A的初始浓度C0。打开250 W氙灯光源（波长为420 nm-750 nm）并计时，分别在30 min，60 min，90 min和120 min各取样一次，悬浮液经过0.45 um尼龙滤膜除去催化剂后，滤液经高效液相色谱分析测得在120 min时双酚A的降解率为64%，如图4所示。
实施例9
准确称取2 mg催化剂和量取0.20 mL的过氧化氢（质量分数30 %）置于反应瓶中，加入100 mL物质的量浓度为1.0 mM的双酚A水溶液，采用0.1 mol/L的盐酸溶液调节溶液pH值为5，将装置置于光催化反应仪中，未开灯前为暗室，剧烈搅拌待催化剂分散均匀，此时取第一个样品标记双酚A的初始浓度C0。打开250 W氙灯光源（波长为420 nm-750 nm）并计时，分别在30 min，60 min，90 min和120 min各取样一次，悬浮液经过0.45 um尼龙滤膜除去催化剂后，滤液经高效液相色谱分析测得在120 min时双酚A的降解率为24%，如图4所示。
实施例10
按实施例2的实验方法，结束降解实施后将混合溶液进行简单的抽滤处理，实现催化剂与水溶液的分离，催化剂分别用100 mL去离子水和50 mL无水乙醇洗涤3次后，充分干燥。再按实施例2的实验方法对催化剂进行实验进行循环使用测试，结果如附图5所示。催化剂经5次循环后双酚A的降解率仍保持在90 %。
实施例11
配置物质的量浓度为6×10-6 mol/L 的DPPMDPC6的三氯甲烷溶液，测试该分子溶液状态下的紫外-可见光吸收光谱，结果如图6所示。分子DPPMDPC6的摩尔消光系数为5.6×105L·mol⁻¹·cm⁻¹，在350 nm至850 nm区间内展现出较强的吸收，最大吸收截止波长为852 nm至近红外区。
Claims (4)
1.一类醌式结构化合物在可见光降解双酚A中的应用，其特征在于，结构如式I所示，标记为DPPMDPC6，
式1
DPPMDPC6作催化剂在可见光降解双酚A中的应用方法如下：
取2 mg催化剂和一定量的质量浓度30 %的过氧化氢置于反应瓶中，加入100 mL双酚A水溶液，采用0.1 mol/L的盐酸溶液与0.1 mol/L的NaOH溶液调节溶液pH，将装置置于光催化反应器中，未开灯前为暗室，剧烈搅拌待催化剂分散均匀，此时取第一个样品标记双酚A的初始浓度C0，打开250 W氙灯光源（波长为420 nm-750 nm）并计时，分别在30 min，60min，90 min和120 min各取样一次，悬浮液经过0.45 um尼龙滤膜除去催化剂后，滤液经高效液相色谱分析检测双酚A的降解率。
2.根据权利要求1所述一类醌式结构化合物在可见光降解双酚A中的应用，其特征在于：所述过氧化氢加入体积为0.05～0.40 mL，其中优选0.20 mL。
3.根据权利要求1所述一类醌式结构化合物在可见光降解双酚A中的应用，其特征在于：所述双酚A水溶液的初始浓度为0.04～1.0 mM，其中优选0.04 mM。
4.根据权利要求1所述一类醌式结构化合物在可见光降解双酚A中的应用，其特征在于：所述双酚A水溶液的pH值为2～11，其中优选pH = 5。
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