CN115536588A - 一种羟基甘氨酸功能性离子液体及其制备方法和在萃取碘中的应用 - Google Patents
一种羟基甘氨酸功能性离子液体及其制备方法和在萃取碘中的应用 Download PDFInfo
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Abstract
本发明涉及离子液体领域,具体的涉及一种羟基甘氨酸功能性离子液体及其制备方法和在萃取碘中的应用。羟基甘氨酸功能性离子液体,具有如(Ⅰ)所示的结构式,制备方法包括如下步骤:在氮气的保护下,向N‑甲基咪唑中滴加2‑溴乙醇和甲苯进行反应,反应完成后洗涤数次,得到粗产物1‑羟基乙基‑3‑甲基咪唑溴盐;用乙酸乙酯和乙腈的混合溶液溶解固体粗产物,重结晶后抽滤,干燥;向提纯后的1‑羟基乙基‑3‑甲基咪唑溴盐加入去离子水稀释,倒入氢氧型阴离子交换树脂中,反应完成后接取流出液,将甘氨酸加入到氢氧型中间体1‑羟基乙基‑3‑甲基咪唑中,搅拌反应,除去水分,真空干燥,得到目标离子液体1‑羟基乙基‑3‑甲基咪唑甘氨酸。
Description
技术领域
本发明涉及离子液体领域,具体的涉及一种羟基甘氨酸功能性离子液体及其制备方法和在萃取碘中的应用。
背景技术
在化工产品的生产过程中,常常伴随着大量有机物的工业含碘废水的排放。含碘废水有毒且难以降解,含碘废水中污染物浓度较高,给污水处理带来了很大的困难,对环境造成了严重的污染,也影响着人们的身体健康,因此,研究高效的吸附剂用于碘的捕集至关重要。
离子液体作为新型的绿色介质,引起了广泛得关注和众多学者得研究,因为其有着特殊得物理性质和化学性质以及良好的设计性。离子液体是指在室温下呈液态的有机盐,这种液态盐由有机阳离子和有机阴离子或者无机阴离子构成。这种呈液态的熔融盐却又不同与其他离子化合物,其在物化性质上表现为有着较低的蒸汽压、难挥发、沸点低、极性强、溶解性强、较宽的化学电位,因此有着广泛的应用。
离子液体具有极大的可调性,这样就大大的增加了离子液体的种类和用途。作为环境友好型离子液体,含有羟基功能型咪唑酸类离子液体可以作为萃取溶剂,很好的萃取碘。
发明内容
本发明提供一种羟基甘氨酸功能性离子液体,能够有效的在有机溶剂中萃取碘,有方法操作简单,成本低,纯度高,稳定性强的优点。
为实现上述目的,本发明的技术方案如下:一种羟基甘氨酸功能性离子液体,具有如(Ⅰ)所示的结构式:
上述的一种羟基甘氨酸功能性离子液体的制备方法,包括如下步骤:
1)1-羟基乙基-3-甲基咪唑溴盐的合成:在氮气的保护下,向N-甲基咪唑中缓慢滴加2-溴乙醇和甲苯进行反应,反应完成后用无水乙醚反复洗涤数次,得到固体粗产物1-羟基乙基-3-甲基咪唑溴盐;
2)1-羟基乙基-3-甲基咪唑溴盐的提纯:用乙酸乙酯和乙腈的混合溶液溶解固体粗产物,重结晶后抽滤,干燥;
3)氢氧型中间体1-羟基乙基-3-甲基咪唑的合成:向提纯后的1-羟基乙基-3-甲基咪唑溴盐加入去离子水稀释,倒入氢氧型阴离子交换树脂中,反应完成后接取流出液,收集时,不断用AgNO3-HNO3溶液检测,直至检测液出现沉淀或混浊,停止收集;
4)将甘氨酸加入到氢氧型中间体1-羟基乙基-3-甲基咪唑中,室温下进行搅拌反应,旋转蒸发除去水分,真空干燥,得到目标离子液体1-羟基乙基-3-甲基咪唑甘氨酸。
上述的一种羟基甘氨酸功能性离子液体的制备方法,步骤1)中,N-甲基咪唑和2-溴乙醇的摩尔比为1:1.1。
上述的一种羟基甘氨酸功能性离子液体的制备方法,步骤1)中,反应温度为110℃,反应时间为48h。
上述的一种羟基甘氨酸功能性离子液体的制备方法,步骤2)中,按体积比,乙酸乙酯:乙腈=2:1。
上述的一种羟基甘氨酸功能性离子液体的制备方法,步骤2)中,干燥温度为65℃,干燥时间为24h。
上述的一种羟基甘氨酸功能性离子液体的制备方法,步骤3)中,按体积比,提纯后的1-羟基乙基-3-甲基咪唑溴盐:去离子水=1:1。
上述的一种羟基甘氨酸功能性离子液体的制备方法,步骤4)中,按摩尔比,氢氧型中间体1-羟基乙基-3-甲基咪唑:甘氨酸=1:1。
上述的一种羟基甘氨酸功能性离子液体的制备方法,步骤4)中,所述的搅拌反应的时间为48h。
上述的一种羟基甘氨酸功能性离子液体在萃取碘中的应用。
本发明的有益效果:在核工业以及化工生产中,放射性碘以及含碘废水都极大的影响着人们的身体健康,离子液体作为新型绿色溶剂,具有可调性、易制备和环境友好等优良特性,普遍应用于绿色化学中,羟基甘氨酸功能性离子液体可以作为萃取溶剂,很好的萃取碘,在防治放射性碘等方面可以发挥较好的作用。
附图说明
图1是实施例1制备的羟基甘氨酸功能型离子液体的氢谱。
图2是实施例1制备的羟基甘氨酸功能型离子液体的碳谱。
图3是实施例1制备的羟基甘氨酸功能性离子液体的循环使用能力。
具体的实施方式
下面通过具体的实例来进一步说明本发明。本发明不限于实施例,在不脱离所述的范围下,可以有微小的变动均在本发明的保护范围之内。
实施例1用于萃取碘的羟基甘氨酸功能性离子液体
制备方法如下:
1)含有羟基的功能型咪唑类离子液体溴盐的制备:
将80mL N-甲基的咪唑加入到三口烧瓶中,氮气保护下,缓慢加入78mL 2-溴乙醇和30mL甲苯滴加完毕后,用油浴锅加热搅拌,110℃下回流反应48h,用无水乙醚反复洗涤数次得到固体粗产物1-羟基乙基-3-甲基咪唑溴盐,所得产物用10mL乙酸乙酯和乙腈的混合物体积比2:1洗涤三次,重结晶,抽滤,然后将上述液体置于干燥器中,65℃下干燥24h,得到1-羟基乙基-3-甲基咪唑溴盐离子液体。N-甲基咪唑与2-溴乙醇的摩尔比为1:1.1。
2)取717行阴离子交换树脂,经过活化再生,处理得到氢氧型阴离子交换树脂。将氢氧型阴离子交换树脂装柱,水洗至中性,放干。将上述的1-羟基乙基-3-甲基咪唑溴盐离子液体倒入去离子水(体积比1:1)中,混合后倒入树脂中,反应2-4h。反应完成后接取流出液,收集时,不断用AgNO3-HNO3溶液检测,直至检测液出现沉淀或混浊,停止收集;树脂的交换容量远大于溴盐离子液体的摩尔物质的量。
3)将上述的氢氧型离子液体和8.580g甘氨酸混合,室温下反应48h,旋蒸、干燥三天,得到1-羟基乙基-3-甲基咪唑甘氨酸离子液体,产率为85.6%,纯度为98%。
图1为所制备离子液体的核磁氢谱,各个氢的特征峰与所对应的离子液体的官能团上氢的位置如图所示,图1氢的特征峰符合1-羟基乙基-3-甲基咪唑甘氨酸离子液体所含氢的位置。图2为所制备离子液体的核磁碳谱,各个碳的特征峰与所对应的离子液体碳的位置如图所示,图2碳的特征峰符合1-羟基乙基-3-甲基咪唑甘氨酸离子液体各基团碳的位置,通过谱图分析可知,所制备离子液体为胆碱乳酸离子液体。
实施例2 1-羟基乙基-3-甲基咪唑甘氨酸萃取碘的应用
(一)萃取分离实验
用100mL容量瓶配制碘浓度为0.01moL/L的环己烷溶液,称量0.5g1-羟基乙基-3-甲基咪唑甘氨酸离子液体于250mL锥形瓶中,加热搅拌,使离子液体在锥形瓶底部形成薄膜。将配好的碘的环己烷溶液倒入锥形瓶中,在25℃~40℃下磁力搅拌进行碘的萃取分离实验,研究了温度对离子液体萃取碘的萃取率的影响,实验结果表明温度降低,萃取率增加,温度在30℃时萃取效果更好。
萃取分离实验时,离子液体粘附于锥形瓶底部,上清液澄清,可以通过检测上清液中碘的浓度来确定离子液体中碘的含量。每隔2分钟,用移液枪量取200μL环己烷相溶液,加环己烷溶液稀释至5mL容量瓶中。配制一系列不同浓度的碘的环己烷溶液,光谱扫描确定碘的最大吸收波长在523nm处,在此波长处进行光度测量,根据吸光度随浓度的变化绘制标准曲线。
(二)1-羟基乙基-3-甲基咪唑甘氨酸离子液体对碘的萃取率
1-羟基乙基-3-甲基咪唑甘氨酸离子液体萃取后,检测可知上层清液碘的浓度为0.004795moL/L,则1-羟基乙基-3-甲基咪唑甘氨酸离子液体对碘的萃取率为质量比1.31325g/g,摩尔比为1.040136mol/mol。
(三)1-羟基乙基-3-甲基咪唑甘氨酸离子液体对碘的循环回收性能
为了测试1-羟基乙基-3-甲基咪唑甘氨酸离子液体的可回收性收,在第一次提取后将其回收,然后再用于后续循环。由于羟基甘氨酸离子液体和碘在乙酸乙酯中的溶解度存在显著差异,因此用乙酸乙酯来回收离子液体。将乙酸乙酯添加到离子液体层后,摇晃30分钟后,碘在乙酸乙酯中达到平衡。然后倾析乙酸乙酯层,重复该过程三次,以确保回收的离子液体不含杂质。每个循环重复相同的过程。最后计算碘去除效率,以评估回收离子液体的萃取能力。图3显示回收的离子液体可以重复使用几次,5次循环后碘去除性能基本保持不变。然而,6次循环后效率逐渐下降,但效率仍保持在约90%。
Claims (10)
2.权利要求1所述的一种羟基甘氨酸功能性离子液体的制备方法,其特征在于,包括如下步骤:
1)1-羟基乙基-3-甲基咪唑溴盐的合成:在氮气的保护下,向N-甲基咪唑中缓慢滴加2-溴乙醇和甲苯进行反应,反应完成后用无水乙醚反复洗涤数次,得到固体粗产物1-羟基乙基-3-甲基咪唑溴盐;
2)1-羟基乙基-3-甲基咪唑溴盐的提纯:用乙酸乙酯和乙腈的混合溶液溶解固体粗产物,重结晶后抽滤,干燥;
3)氢氧型中间体1-羟基乙基-3-甲基咪唑的合成:向提纯后的1-羟基乙基-3-甲基咪唑溴盐加入去离子水稀释,倒入氢氧型阴离子交换树脂中,反应完成后接取流出液,收集时,不断用AgNO3-HNO3溶液检测,直至检测液出现沉淀或混浊,停止收集;
4)将甘氨酸加入到氢氧型中间体1-羟基乙基-3-甲基咪唑中,室温下进行搅拌反应,旋转蒸发除去水分,真空干燥,得到目标离子液体1-羟基乙基-3-甲基咪唑甘氨酸。
3.根据权利要求2所述的一种羟基甘氨酸功能性离子液体的制备方法,其特征在于,步骤1)中,N-甲基咪唑和2-溴乙醇的摩尔比为1:1.1。
4.根据权利要求2所述的一种羟基甘氨酸功能性离子液体的制备方法,其特征在于,步骤1)中,反应温度为110℃,反应时间为48h。
5.根据权利要求2所述的一种羟基甘氨酸功能性离子液体的制备方法,其特征在于,步骤2)中,按体积比,乙酸乙酯:乙腈=2:1。
6.根据权利要求2所述的一种羟基甘氨酸功能性离子液体的制备方法,其特征在于,步骤2)中,干燥温度为65℃,干燥时间为24h。
7.根据权利要求2所述的一种羟基甘氨酸功能性离子液体的制备方法,其特征在于,步骤3)中,按体积比,提纯后的1-羟基乙基-3-甲基咪唑溴盐:去离子水=1:1。
8.根据权利要求2所述的一种羟基甘氨酸功能性离子液体的制备方法,其特征在于,步骤4)中,按摩尔比,氢氧型中间体1-羟基乙基-3-甲基咪唑:甘氨酸=1:1。
9.根据权利要求2所述的一种羟基甘氨酸功能性离子液体的制备方法,其特征在于,步骤4)中,所述的搅拌反应的时间为48h。
10.权利要求1所述的一种羟基甘氨酸功能性离子液体在萃取碘中的应用。
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