CN107081133A - 多孔有机物作为抗生素吸附剂的应用 - Google Patents
多孔有机物作为抗生素吸附剂的应用 Download PDFInfo
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Abstract
本发明涉及一种多孔有机物的新用途。所述的多孔有机物由酚类化合物(单体)与烷氧基甲烷经付克烷基化反应得到。本发明所述的多孔有机物可作为四环素类抗生素和磺胺类抗生素吸附剂的应用,且可再生循环使用。
Description
技术领域
本发明涉及一种多孔有机物的用途,具体地说,涉及一种由酚类化合物(单体)与烷氧基甲烷经付克烷基化反应得到的多孔有机物的新用途。
背景技术
过去几年,越来越多的水系环境中被检测出抗生素残留。这些抗生素结构复杂,成分多样,很难自然降解。而且,即使水体中的抗生素处于较低浓度,也会对自然环境造成较大危害,引起抗药细菌的传播,进一步造成人体和其他生物体的光谱抗药性。因此,废水中抗生素的去除越来越受到重视。
目前抗生素去除的方法主要有活性污泥法,光催化法,吸附法等。其中活性污泥法无法应对复杂的污染废水体系,处理效果不佳;光催化法成本较高,工程化技术不成熟;相比之下,吸附法操作简单,成本低廉,去除效率高,是较合适的抗生素去除方法。
多种材料可以作为抗生素的吸附剂,包括活性炭、碳纳米管、离子交换树脂,金属氧化物等。但碳纳米管生产成本高,难以大规模应用;活性炭再生困难,难以重复利用;金属氧化物和离子交换树脂等材料比表面积小,吸附效果不理想。
因此,仍有必要继续开发具有吸附效果好、成本低、能够重复利用优点的新型材料,作为废水中抗生素的吸附剂。
发明内容
本发明的发明人经研究发现:将酚类化合物(单体)与烷氧基甲烷经付克烷基化反应,可获得具有多孔有机物(其为具有纳米孔结构(包含微孔和介孔)的大分子化合物)。实验表明:该多孔有机物可作为抗生素吸附剂的应用。
本发明的目的在于,揭示一种多孔有机物的新用途。
一种多孔有机物在制备抗生素吸附剂中的应用,或,一种多孔有机物作为抗生素吸附剂的应用;
所述的多孔有机物是:在有路易斯(Lewis)酸(催化剂)存在的条件下,由酚类化合物(原料或称单体)与过量的式II所示化合物于70℃~90℃反应至少24小时得到的产物,
其中,所述酚类化合物选自:式I所述化合物中一种或两种以上(含两种)的混合物,A为C6~C20的芳环基;R1和R2分别独立选自:C1~C4烷基中一种。
本发明所述的多孔有机物的孔容为0.01cm3/g~0.43cm3/g,比表面积(BET)2m2/g~728m2/g。
实验表明:本发明所述的多孔有机物对四环素类抗生素(如盐酸四环素、金霉素、土霉素和强力霉素等)和磺胺类抗生素(如磺胺间二甲氧基嘧啶钠盐等)均有较好吸附效果。
其中,对于盐酸四环素的饱和吸附量为42.6mg/g~178.1mg/g,对金霉素的饱和吸附量为35.8mg/g~189.5mg/g,对土霉素的饱和吸附量为24.9mg/g~181.8mg/g,对强力霉素的饱和吸附量为47.4mg/g~189.4mg/g,对于磺胺间二甲氧基嘧啶钠盐的饱和吸附量为28.2mg/g~187.4mg/g。本发明所述的多孔有机物可以较快去除废水中的抗生素(4小时内,去除率可以达到90%)。
此外,本发明所述多孔有机物在吸附实验后,用稀盐酸和水洗涤可以迅速脱附再生,并再次循环使用。
附图说明
图1.是本发明所述多孔有机物(POP-a,POP-b,POP-c和POP-d)的红外光谱谱图;
图2.是本发明所述多孔有机物的扫描电子显微镜照片,
其中,a)-POP-a,b)-POP-b,c)-POP-c,d)-POP-d,比例尺为5微米;
图3.是本发明所述多孔有机物的氮气吸附等温线(77K);
图4.是本发明所述多孔有机物的热重曲线;
图5.是POP-b对不同初始浓度的盐酸四环素的吸附动力学曲线;
图6.是pH值对POP-b的盐酸四环素吸附效果影响曲线;
图7.是POP-b对抗生素吸附的再生性能。
具体实施方式
在本发明一个优选的技术方案中,R1和R2均为甲基。
在本发明另一个优选的技术方案中,A为二价的苯基,联苯基,萘基或联萘基;
进一步优选的技术方案是:A为下列基团中一种(曲线标记处为取代位):
在本发明又一个优选的技术方案中,所述酚类化合物(原料或称单体)选自:下列化合物中一种或两种(含两种)以上混合物:
进一步优选的技术方案是所述酚类化合物(原料或称单体)为式Ia所示化合物和式Ib所示化合物的混合物。
在本发明又一个优选的技术方案中,酚类化合物(原料或称单体)与过量的式II所示化合物的反应温度为70℃~90℃,所用催化剂为三氯化铁,反应介质为卤代烷(如氯代的甲烷或乙烷等)。
在本发明又一个优选的技术方案中,本发明所述的多孔有机物较为适合处理(吸附)含抗生素(抗生素种类与前文所述相同)浓度为1mg/L-100mg/L及pH值为2-12(更优选pH值为9-10)的废水,多孔有机物的用量为0.4g/L-0.6g/L。
具体处理(吸附)方法是:在10℃~50℃条件下,将本发明所述的多孔有机物按量置于待处理的废水中即可。待处理(吸附)结束后,离心分离回收所放置的多孔有机物,用稀盐酸洗涤再生,循环使用。
其中,当采用本发明所述的多孔有机物处理含浓度为4mg/L盐酸四环素的废水时,两小时内,盐酸四环素的去除率达到92%。
术语解释:上文中L意为1升待处理的废水,下同。
下面通过实施例对本发明做进一步阐述,其目的仅在于更好理解本发明的内容。因此,所举之列不限制本发明的保护范围。
实施例1
在三口烧瓶中,将10mmol的1,1′-联二萘酚(式Ia所示化合物)溶于20mL二氯乙烷中,再加入40mmol二甲氧基甲烷(式IIa所示化合物),搅拌5分钟后,加入40mmol无水氯化铁。反应液升温至80度,并在此状态下保持24小时。冷却后,抽滤,收集固体,固体用甲醇洗涤,并用甲醇索氏提取24小时,所得固体即为目标物(简记为″POP-a″)。
FTIR(KBr压片):3446cm-1,2925cm-1,2854cm-1,1633cm-1,1435cm-1,1382cm-1,1263cm-1,1195cm-1,1078cm-1,804cm-1,624cm-1,477cm-1。
实施例2
除以式Ib所示化合物替换式Ia所示化合物,及式Ib所示化合物与式IIa所示化合物的摩尔比为1∶3外,其它条件及步骤与实施例1相同,得到目标物(简记为″POP-b″)。
FTIR(KBr压片):3438cm-1,2925cm-1,2857cm-1,1633cm-1,1444cm-1,1382cm-1,1263cm-1,1201cm-1,1073cm-1,760cm-1,708cm-1,626cm-1,469cm-1。
实施例3
除以式Ic所示化合物替换式Ia所示化合物,及式Ic所示化合物与式II所示化合物的摩尔比为1∶2外,其它条件及步骤与实施例1相同,得到目标物(简记为“POP-c”)。
FTIR(KBr压片):3450cm-1,2924cm-1,2854cm-1,1633cm-1,1543cm-1,1385cm-1,1234cm-1,1077cm-1,962cm-1,886cm-1,794cm-1,674cm-1,467cm-1。
实施例4
除以式Id所示化合物替换式Ia所示化合物及式Id与式II所示化合物的摩尔比为1∶2外,其它条件及步骤与实施例1相同,得到目标物(简记为″POP-d″)。
FTIR(KBr压片):3435cm-1,2925cm-1,2854cm-1,1639cm-1,1441cm-1,1382cm-1,1260cm-1,1071cm-1,789cm-1,706cm-1,603cm-1,471cm-1。
本发明制备的多孔有机物(POP-a~d)的红外谱图见图1,扫描电子显微镜照片见图2,氮气吸附等温线见图3,及热重曲线见见图4。
实施例5
分别对上述制备的多孔有机物进行比表面(BET法)、孔容、热分解温度进行测定,其结果见表1(四种多孔有机物的性质)。
表1
实施例6
本发明所述多孔有机物吸附抗生素的测试
测试步骤如下:
分别将含有浓度为100mg/L的盐酸四环素、土霉素、金霉素、强力霉素和磺胺间二甲氧基嘧啶钠盐的五种废水的pH值调节9-10。将测试样品(POP-a~d)按0.5mg/L的量分别加入所述五种废水中,在25℃条件下,搅拌24小时后,再分别测量五种废水中抗生素的余量,从而获得测试样品的抗生素平衡吸附量,具体结果见表2。
表2
实施例7
在三口烧瓶中,将2mmol的式Ia所示化合物与8mmol式Ib所示化合物溶于20mL二氯乙烷中,再加入32mmol式IIa所示化合物,搅拌5分钟后,加入40mmol无水氯化铁。反应液升温至80度,并在此状态下保持24小时。冷却后,抽滤,收集固体,固体用甲醇洗涤,并用甲醇索氏提取24小时,所得固体即为目标物(简记为″POP-0.2a-0.8b″)。
FTIR(KBr压片):3451cm-1,2922cm-1,2851cm-1,1638cm-1,1542cm-1,1380cm-1,1235cm-1,1071cm-1,960cm-1,885cm-1,791cm-1,678cm-1,463cm-1。
实施例8
除式Ia所示化合物的量为5mmol,式Ib所示化合物5mmol及式IIa所示化合物的量为35mmol外,其它条件及步骤与实施例7相同,得到目标物(简记为″POP-0.5a-0.5b″)。
FTIR(KBr压片):3442cm-1,2927cm-1,2852cm-1,1639cm-1,1432cm-1,1381cm-1,1266cm-1,1191cm-1,1073cm-1,809cm-1,622cm-1,479cm-1。
实施例9
除式Ia所示化合物的量为8mmol,式Ib所示化合物为2mmol及式IIa所示化合物的量为38mmol外,其它条件及步骤与实施例7相同,得到目标物(简记为″POP-0.8a-0.2b″)。
实施例10
本发明所述多孔有机物吸附抗生素的测试
将由实施例7-9制备的目标物按实施例6所述方法测试其对抗生素吸附能力,具体结果见表3。
表3
实施例11
不同初始浓度的抗生素对本发明所述多孔有机物吸附抗生素性能的影响测试
抗生素以盐酸四环素为例,本发明所述多孔有机物以POP-b为例进行测试。具体测试步骤如下:
分别配置初始浓度为1mg/L,4mg/L,10mg/L,15mg/L,20mg/L,40mg/L,60mg/L,80mg/L和100mg/L的盐酸四环素水溶液,采用上述实施例6所述方法对POP-b进行吸附实验。具体结果见图5及表3(POP-b对不同初始浓度盐酸四环素的平衡吸附量)。
表4
由表4及图5可知:POP-b的平衡吸附量与抗生素的初始浓度符合Langmuir模型,初始浓度达到一定值后吸附量趋于平衡,达到饱和吸附量。
其它抗生素及多孔有机物也有类似现象,在此不再一一赘述。
实施例12
pH值对本发明所述多孔有机物吸附抗生素性能的影响测试
同样,抗生素以盐酸四环素为例,本发明所述多孔有机物以POP-b为例进行测试。具体测试步骤如下:
调节浓度为4mg/L的盐酸四环素溶液pH值为2~12,POP-b的用量0.5mg/L,采用实施例6所述的方法进行吸附测试。结果见图6。
由图6可知,当pH值为9~10时,POP-b吸附抗生素的效果最佳。其它抗生素及多孔有机物也有类似现象。限于篇幅,在此不再一一赘述。
实施例13
本发明所述多孔有机物再生性能测试
0.5mg/L的吸附剂加入到4mg/L的抗生素溶液中,吸附24小时。吸附完成后,离心回收吸附剂,清液检测抗生素浓度计算去除率,吸附剂用稀盐酸(pH值为5左右)洗涤4次,再用水洗涤,烘干后吸附剂即可投入下一个循环重复上述操作,结果见图7。
由图7可知,第一次循环去除率为95.9%,第五次循环去除率仅仅下降到87.9%。表明本发明提供的多孔有机物具有良好的再生性能。
Claims (7)
1.一种多孔有机物作为抗生素吸附剂的应用;
所述的多孔有机物是:在有路易斯酸存在的条件下,由酚类化合物与过量的式II所示化合物于70℃~90℃反应至少24小时得到的产物;所述的抗生素为四环素类抗生素和磺胺类抗生素;
其中,所述酚类化合物选自:式I所述化合物中一种或两种以上的混合物,A为C6~C20的芳环基;R1和R2分别独立选自:C1~C4烷基中一种。
2.如权利要求1所述的应用,其特征在于,其中,R1和R2均为甲基。
3.如权利要求1所述的应用,其特征在于,其中,A为二价的苯基,联苯基,萘基或联萘基。
4.如权利要求3所述的应用,其特征在于,其中,A为下列基团中一种:
5.如权利要求1所述的应用,其特征在于,其中,所述酚类化合物选自:下列化合物中一种或两种以上混合物:
6.如权利要求5所述的应用,其特征在于,其中,所述酚类化合物为式Ia所示化合物和式Ib所示化合物的混合物。
7.如权利要求1所述的应用,其特征在于,其中,所述路易斯酸为三氯化铁,反应介质为卤代烷。
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