CN111215041A - 一种酰胺类反相液相色谱填料的合成方法 - Google Patents
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Abstract
本发明以含有机官能团的羧酸为原料,与N,N‑羰基二咪唑(CDI)反应制备出中间体羰基咪唑盐,再加入氨丙基硅烷试剂,一锅即制得酰胺嵌入型硅烷试剂,再修饰到载体表面即制得酰胺嵌入型反相色谱填料。此种方法制备的酰胺嵌入型填料,适用于100%水相为流动相分离极性化合物,对碱性化合物拖尾有明显改善。制备方法简便、经济、低毒,易于放大及产业化。
Description
技术领域
本发明方法涉及一种酰胺类反相液相色谱填料的合成新途径。
背景技术
高效液相色谱的固定相一直被誉为液相色谱的核心,其发展是影响色谱技术发展的关键问题之一。通常而言,色谱仪器的差异不大,主要是根据样品性质选择固定相,并对流动相进行优化,实现不同类型化合物的分离。因此,在高效液相色谱仪器商品化之后,固定相的发展显得尤为重要,对固定相的研究源源不绝且日新月异;同时,每一次材料科学的重大发展以及合成手段的提高都会给固定相的开发带来新的契机。
按照不同的色谱分离模式和机理,色谱填料可以分为正相、反相、亲水、离子交换以及亲和色谱等多种固定相。尽管目前市场上已有多种商品化的色谱固定相,但是研制柱效高、机械强度好、使用寿命长的新型色谱填料仍然是目前色谱领域的研究热点之一。
根据极性基团的分布位置,极性修饰的固定相可分为:1、极性封尾型(polar-endcapped)固定相;2、极性嵌入型(polar-embedded)固定相。极性封尾烷基固定相实质上是长烷基和极性功能化短烷基混合型固定相,二者的排布类似栅栏结构;极性嵌入烷基固定相可以视为烷基的极性衍生物固定相,嵌入的极性基团有醚、酰胺、磺胺、铵根、脲、氨基甲酸酯。这些内嵌基团均通过各式商品硅烷与烷烃衍生物反应制得。
在实验室里,色谱工作者们自辟蹊径,以不同的衍生手段、固载方法创造了各式各样的极性嵌入型烷基固定相;这些固定相继承了烷基固定相良好的疏水性能,同时各具特色,总体言之它们具有以下共同点:1、具有反相特征;2、对极性分析物表现出异于常规烷基固定相的选择性;3、适用于高水含量的流动相,甚至100%水相,不会发生“去浸润”;这一优点保证了极性分析物的快速、高效、重复性分离;4、对残余硅醇基的屏蔽作用,对于易离解分析物,尤其是碱性的分析物,此类固定相可以得到超出常规反相色谱固定相的分离结果。
Buszewski等人 (Buszewski等,J. Chromatography, 1991, 552, 415-427)第一步以烷基羧酸和二氯亚砜为原料,制备出烷基酰氯;第二步,烷基酰氯与氨丙基硅烷试剂反应制备出酰胺嵌入型硅烷试剂,再将其修饰到硅胶表面,即制得酰胺嵌入型反相填料;国内外色谱填料厂家,利用此方法已经成功将制备的酰胺嵌入型色谱填料商品化。但该方法需要两步制备出所需的酰胺嵌入型硅烷试剂,制备过程较为繁琐;即使现在许多的烷基酰氯已经商业化,其成本比较高,商业化酰氯试剂非常容易水解,且毒性较大,因此需要一种价格低廉,毒性小,合成路线较为简单,反应时间短,易于放大及产业化的新的填料合成工艺。
发明内容
本发明提供一种制备简单、经济、低毒,易于放大及产业化具有良好选择性的酰胺嵌入型液相色谱固定相合成方法。
本发明提供的技术方案是以含有机官能团的羧酸和氨基硅烷试剂为原料,先合成酰胺型硅烷试剂,再将其修饰到固定相基质表面即合成出酰胺嵌入型液相色谱固定相,具体包括以下几个步骤:
(1)均相合成酰胺嵌入型硅烷
将带有机官能团羧酸与甲苯试剂加入到烧瓶中,加热回流,共沸除水,加入N,N-羰基二咪唑(CDI),继续搅拌3小时,再加入氨基硅烷反应3小时;旋蒸除去溶剂,加入到乙腈中,结晶得到固体,抽滤,烘干即为合成的酰胺嵌入型硅烷;
(2)表面键合修饰
将固定相基质分散在甲苯中,加热回流,再缓慢加入合成的酰胺嵌入型硅烷试剂,机械搅拌并回流反应12小时,冷却过滤、溶剂洗涤后,将得到的固体真空干燥即为酰胺嵌入型液相色谱固定相。
优选地,羧酸含有的有机官能团为C1-C29的直链或支链烷基、烷基化芳香基团(烷基碳链长度为1-29)。
优选地,氨基硅烷碳链长度在C3-C18。
优选地,固定相基质为二氧化硅、氧化钛、氧化锆或者氧化铝。
优选地,固定相基质形貌为球形或者无定形。
优选地,重结晶的溶剂为乙腈。
其合成路线为:
本发明的有益效果是:本发明以拟修饰基团的羧酸为原料,与N,N-羰基二咪唑反应制备出中间体羰基咪唑盐,再加入氨丙基硅烷试剂,一锅即制得酰胺嵌入型硅烷试剂,再修饰到载体表面即制得酰胺嵌入型反相色谱填料。合成路线较为简单,羧酸和CDI价格低廉,因此生产成本较低,毒性小,反应时间短,易于放大及产业化。
附图说明
图1是酰胺嵌入型C16色谱填料分离4标准品色谱图
图2是酰胺嵌入型十六烷基硅烷核磁谱图
图3是酰胺嵌入型C16色谱填料亲水性测试。
具体实施方式
实施例1:
(1)均相合成酰胺嵌入型硅烷
室温下,将棕榈酸(10 mmol)与甲苯120ml加入到250ml烧瓶中,加热,共沸除水3小时,加入CDI(10.5mmol)反应3小时,再加入3-氨丙基三乙氧基硅烷(10.5 mmol),继续反应12小时,真空减压蒸除溶剂,加入乙腈120 ml,搅拌析晶,抽滤,固体用少量乙腈洗涤,滤饼晾干,得酰胺嵌入型硅烷;
(2)表面键合修饰
将6.6g球形二氧化硅分散在溶剂甲苯中,加热回流,再加入10 mmol合成的酰胺嵌入型硅烷试剂,机械搅拌并回流16小时,趁热过滤后,将得到的固体依次用甲苯和甲醇洗涤,最后70℃鼓风干燥,再真空干燥。
实施例2:将实施例1中的棕榈酸改为辛酸,固定相基质球形二氧化硅,其余条件相同,制备出辛基酰胺嵌入型液相色谱固定相。
实施例3: 将实施例1中的棕榈酸改为二十二酸,固定相基质球形二氧化硅改为球形氧化钛,其余条件相同,制备出二十二酰胺嵌入型液相色谱固定相。
实施例4:将实施例1种的球形二氧化硅改为无定形二氧化硅,其余条件相同,制备出无定形酰胺嵌入型液相色谱固定相。
Claims (6)
1.一种酰胺嵌入型液相色谱固定相合成方法,其特征在于包括以下几个步骤:
(1)均相合成酰胺嵌入型硅烷
将含有机官能团的羧酸与甲苯试剂加入到烧瓶中,加热回流,共沸除水,加入N,N-羰基二咪唑,继续搅拌反应,再加入氨丙基硅烷试剂;旋蒸除去溶剂,重新溶解结晶后,抽滤,烘干即为合成的酰胺嵌入型硅烷;
(2)表面键合修饰
将固定相基质分散在甲苯中,加热回流,再缓慢加入合成的酰胺嵌入型硅烷试剂,机械搅拌。
2.根据权利要求1所述的方法,其特征在于羧酸含有的有机官能团为C1-C29的直链或支链烷基、烷基化芳香基团(烷基碳链长度为1-29)。
3.根据权利要求1所述的方法,其特征在于氨基硅烷碳链长度在C3-C18。
4.根据权利要求1所述的方法,其特征在于固定相基质为二氧化硅、氧化钛、氧化锆或者氧化铝。
5.根据权利要求1所述的方法,其特征在于固定相基质形貌为球形或者无定形。
6.根据权利要求1所述的方法,其特征在于重结晶的溶剂为乙腈。
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