CN112710743B - 碳酸酯溶剂中杂质的分离与检测方法及其应用 - Google Patents
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Abstract
本发明公开了碳酸酯溶剂中杂质的分离与检测方法及其应用,属于有机溶剂中杂质检测技术领域。所述分离与检测方法,包括如下步骤:1)采用反相色谱对待测溶剂进行层析、梯度洗脱和等度洗脱,得到反相洗脱液和反相色谱图;2)采用正相色谱对待测溶剂进行层析、梯度洗脱和等度洗脱,得到正相洗脱液和正相色谱图;3)分别对反相洗脱液和正相洗脱液进行切割,对切割后的反相洗脱液和正相洗脱液进行真空冷冻干燥,得到反相洗脱液浓缩样品和正相洗脱液浓缩样品;4)将反相洗脱液浓缩样品和正相洗脱液浓缩样品分别使用GCMS和核磁氢谱进行检测分析,得到杂质分子的结构信息。本发明提供的方法能够有效地对碳酸酯溶剂中的杂质进行分离检测。
Description
技术领域
本发明属于有机溶剂中杂质检测技术领域,具体涉及碳酸酯溶剂中杂质的分离与检测方法及其应用。
背景技术
碳酸酯类高纯溶剂中的某些杂质分子往往会影响电解液的使用性能,对不同功能电解液的品质好坏影响显著。随着锂电池技术的发展和进步,电池行业对电解液中的高纯溶剂的纯度也提出了更高的要求,对溶剂中杂质含量水平已从ppm级别变化到到ppb级别,这就促使溶剂生产商不断提高产品等级和杂质检测能力。
色谱分析是复杂有机物分子定性定量鉴别的主要技术,通过不同的色谱分离和检测技术可以分析绝大多数有机化合物,但是对于复杂基体或者痕量级别杂质的高纯物质中有一些不易分离和离子化的化合物存在致使杂质定性分析困难或者不全面。碳酸酯类溶剂的杂质分子直接定性往往比较困难,特别是某些具有特殊官能团的痕量轻组分。因此,提供一种能够有效检测碳酸酯溶剂中杂质的方法显得尤为重要。
发明内容
为了解决背景技术中碳酸酯溶剂中杂质定性比较困难的技术问题,本发明提供了一种碳酸酯溶剂中杂质的分离与检测方法及其应用,能够有效地对碳酸酯溶剂中的杂质进行分离检测。
为实现上述目的,本发明提供如下技术方案:碳酸酯溶剂中杂质的分离与检测方法,包括如下步骤:
1)采用反相色谱对待测溶剂进行层析、梯度洗脱和等度洗脱,得到反相洗脱液和反相色谱图;
2)采用正相色谱对待测溶剂进行层析、梯度洗脱和等度洗脱,得到正相洗脱液和正相色谱图;
3)分别对所述步骤1)和2)的反相洗脱液和正相洗脱液进行切割,对切割后的反相洗脱液和正相洗脱液进行真空冷冻干燥和/或真空旋转蒸发干燥,得到反相洗脱液浓缩样品和正相洗脱液浓缩样品;
4)将所述步骤3)的反相洗脱液浓缩样品和正相洗脱液浓缩样品分别使用GCMS和核磁氢谱进行检测分析,得到杂质分子的结构信息;
所述步骤1)和2)没有时间顺序的限定。
优选的,所述步骤1)中梯度洗脱和等度洗脱的方式为:先采用乙腈和水的混合液进行梯度洗脱,两者起始比为V乙腈:V水=1:4~19,到8分钟后为V乙腈:V水=100:0,再使用乙腈等度洗脱2分钟。
优选的,所述步骤2)中梯度洗脱和等度洗脱的方式为:先采用正己烷和二氯甲烷的混合液进行梯度洗脱,两者起始比为V正己烷:V二氯甲烷=1:9,到8分钟后为V正己烷:V二氯甲烷=10:0,再使用正己烷等度洗脱2分钟。
优选的,所述步骤1)和2)中采用紫外检测器和/或蒸发光散射检测器对反相洗脱液和正相洗脱液进行检测。
优选的,所述步骤3)中基于加大1~100倍体积过载量而不超过柱容量的馏分收集来进行切割,即100μL到10mL的样品量。
优选的,所述步骤3)中真空冷冻干燥时的工艺参数为:物料厚度1~100mm,干燥室真空度0.01~0.1Mpa,干燥时间1~48h;所述真空旋转蒸发干燥的工艺参数为:水浴温度30~150℃,旋蒸的真空度为0~0.09Mpa。
优选的,所述步骤1)中反相色谱采用的制备柱包括C18、C8和聚苯乙烯-二乙烯苯柱子。
优选的,所述步骤2)中正相色谱采用的制备柱包括硅胶、氨基键合、氰基以及二醇基及硝基键合相柱子。
优选的,所述碳酸酯类溶剂包括碳酸乙烯酯、碳酸丙烯酯、碳酸二甲酯、碳酸二乙酯以和碳酸甲乙酯。
本发明还提供了一种上述方案所述的分离与检测方法在分离与检测碳酸酯溶剂杂质中的应用。
与现有技术相比,本发明的有益效果是:
本发明采用正相色谱和反相色谱结合来分离不同极性的杂质分子,扩大了杂质分子检测的种类,弥补了单一技术的局限性,提高了杂质分子的检测限,增加了杂质分子的检出数量和类别。采用紫外检测器或蒸发光散射检测器对洗脱液进行检测,为杂质在制备型色谱中的分离与富集提供了监测手段,且可以弥补气象色谱定性上面的不足。
碳酸酯类溶剂中的杂质经分离后分别通过真空冷冻干燥进行富集,使其中的水分直接升华成气态,可以避免常规旋转蒸发干燥浓缩降低收率的问题,最低限量地降低目标化合物的损失,从而提高了痕量成分的检测限。最后使用检测灵敏度高的气相质谱联用定性和核磁谱定性来准确定性未知化合物,减少定性的偏差,提高目标物化合物分子结构定性的准确性。
附图说明
图1为实施例1中杂质2-甲基-2-戊烯醛、2-烯丙氧基丙酸乙酯和1-(烯丙氧基)-2-丙醇的色谱图;
图2为实施例1中杂质2-甲基-2-戊烯醛的质谱图;
图3为实施例1中杂质2-甲基-2-戊烯醛的氢谱图;
图4为实施例1中杂质二缩三乙二醇的色谱图;
图5为实施例1中杂质二缩三乙二醇的质谱图;
图6为实施例1中杂质二缩三乙二醇的氢谱图;
图7为实施例1中杂质1-苯基-1-戊烯的色谱图;
图8为实施例1中杂质1-苯基-1-戊烯的质谱图;
图9为实施例1中杂质1-苯基-1-戊烯的氢谱图。
具体实施方式
本发明提供了一种碳酸酯溶剂中杂质的分离与检测方法,包括如下步骤:
1)采用反相色谱对待测溶剂进行层析、梯度洗脱和等度洗脱,得到反相洗脱液和反相色谱图;
2)采用正相色谱对待测溶剂进行层析、梯度洗脱和等度洗脱,得到正相洗脱液和正相色谱图;
3)分别对所述步骤1)和2)的反相洗脱液和正相洗脱液进行切割,对切割后的反相洗脱液和正相洗脱液进行真空冷冻干燥和/或真空旋转蒸发干燥,得到反相洗脱液浓缩样品和正相洗脱液浓缩样品;
4)将所述步骤3)的反相洗脱液浓缩样品和正相洗脱液浓缩样品分别使用GCMS和核磁氢谱进行检测分析,得到杂质分子的结构信息;
所述步骤1)和2)没有时间顺序的限定。
本发明采用反相色谱对待测溶剂进行层析、梯度洗脱和等度洗脱,得到反相洗脱液和反相色谱图。在本发明中,所述碳酸酯类溶剂包括碳酸乙烯酯、碳酸丙烯酯、碳酸二甲酯、碳酸二乙酯以和碳酸甲乙酯。在本发明中,所述反相色谱采用的制备柱包括C18、C8和聚苯乙烯-二乙烯苯柱子,优选为C18。在本发明中,所述C18制备柱的尺寸优选为10~100um*9.4mm*250mm。在本发明中,所述梯度洗脱和等度洗脱的方式优选为:先采用乙腈和水的混合液进行梯度洗脱,两者起始比为V乙腈:V水=1:4~19,到8分钟后为V乙腈:V水=100:0,再使用乙腈等度洗脱2分钟。在本发明中,优选采用紫外检测器和/或蒸发光散射检测器对反相洗脱液进行检测。在本发明中,采用紫外检测器进行检测时的参数优选为波长:200~450nm,流速:4mL/min;采用蒸发光散射检测器进行检测时的参数优选为漂移管温度:105℃,气体流量:2.8mL/min,流速:4mL/min。
本发明采用正相色谱对待测溶剂进行层析、梯度洗脱和等度洗脱,得到正相洗脱液和正相色谱图。在本发明中,所述正相色谱采用的制备柱包括硅胶,氨基键合,氰基以及二醇基及硝基键合相柱子,优选为硅胶柱。在本发明中,所述硅胶柱的尺寸优选为10μm*250mm*20mm。在本发明中,所述梯度洗脱和等度洗脱的方式优选为:先采用正己烷和二氯甲烷的混合液进行梯度洗脱,两者起始比为V正己烷:V二氯甲烷=1:9,到8分钟后为V正己烷:V二氯甲烷=10:0,再使用正己烷等度洗脱2分钟。在本发明中,优选采用紫外检测器或蒸发光散射检测器对正相洗脱液进行检测。在本发明中,采用紫外检测器进行检测时的参数优选为波长:200~450nm,流速:4mL/min;采用蒸发光散射检测器进行检测时的参数优选为漂移管温度:105℃,气体流量:2.8mL/min,流速:4mL/min。
得到反相洗脱液和正相洗脱液后,本发明分别对所述反相洗脱液和正相洗脱液进行切割,对切割后的反相洗脱液和正相洗脱液进行真空冷冻干燥和/或低温真空旋转干燥,得到反相洗脱液浓缩样品和正相洗脱液浓缩样品。在本发明中,优选基于加大1~100倍体积过载量而不超过柱容量的馏分收集来进行切割,即100μL到10mL的样品量。具体为目标化合物不超过柱载量的分离体积量,为分析量的1-100倍体积即不超过10mL的体积。在本发明中,所述真空冷冻干燥时的工艺参数优选为:物料厚度1~100mm,干燥室真空度0.01~0.1Mpa,干燥时间1~48h。在本发明中,所述真空旋转蒸发干燥的工艺参数优选为:水浴温度30~150℃,旋蒸的真空度为0~0.09Mpa。
得到反相洗脱液浓缩样品和正相洗脱液浓缩样品后,本发明将所述反相洗脱液浓缩样品和正相洗脱液浓缩样品分别使用GCMS和核磁氢谱进行检测分析,得到杂质分子的结构信息。
本发明还提供了一种上述方案所述的分离与检测方法在分离与检测碳酸酯溶剂杂质中的应用。
为了进一步说明本发明,下面结合实施例对本发明提供的技术方案进行详细地描述,但不能将它们理解为对本发明保护范围的限定。
实施例1
(1)使用C18反相制备柱(柱长为10um*9.4*250mm)对待测样品进行分析,UV=200~450nm,流速=4mL/min。洗脱液为乙腈和水的混合溶液,从两者起始比为V乙腈:V水=5:95到8分钟后为V乙腈:V水=100:0的梯度程序洗脱样品,再使用纯乙腈等度洗脱2分钟。得到的色谱图如图1所示。根据图1确定杂质为2-甲基-2-戊烯醛、2-烯丙氧基丙酸乙酯和1-(烯丙氧基)-2-丙醇。
(2)经优化切割收集洗脱液,将收集的洗脱液进行真空冷冻干燥(物料厚度10mm、冷阱温度为-55℃、干燥室真空度20Pa、干燥时间32h),得到浓缩样品。
(3)将(2)制备的浓缩样品分别使用GCMS和核磁氢谱检测,得到的杂质质谱图如图2所示,得到的杂质氢谱图如图3所示,获得杂质分子结构信息,根据图2确定杂质为2-甲基-2-戊烯醛,根据图3确定杂质为2-甲基-2-戊烯醛。
(4)使用C18反相制备柱(柱长为10um*9.4*250mm),ELSD参数:漂移管温度105℃,气体流量2.8mL/min,流速=4mL/min。洗脱液为乙腈和水的混合溶液,从两者起始比为V乙腈:V水=2:8到8分钟后为V乙腈:V水=10:0的梯度程序洗脱样品,再使用纯乙腈等度洗脱2分钟。得到的色谱图如图4所示,根据图4确定杂质为二缩三乙二醇。
(5)经优化切割收集洗脱液,将收集的洗脱液进行真空冷冻干燥(冷冻干燥的工艺参数为:物料厚度10mm、冷阱温度为-50℃、干燥室真空度30Pa、干燥时间24h),得到浓缩样品。
(6)将(5)制备的浓缩样品分别使用GCMS和核磁氢谱检测,得到的杂质质谱图如图5所示,得到的杂质氢谱图如图6所示,获得杂质分子结构信息,根据图5确定杂质为二缩三乙二醇,根据图6确定杂质为二缩三乙二醇。
(7)使用正相制备硅胶柱(柱型号为250*20mm*10μm),UV=200~450nm,流速=4mL/min。洗脱液为二氯甲烷和正己烷的混合溶液,从两者起始比为V正己烷:V二氯甲烷=1:9到8分钟后为V正己烷:V二氯甲烷=10:0的梯度程序洗脱样品,再使用纯正己烷等度洗脱2分钟。得到的色谱图如图7所示,根据图7确定杂质为1-苯基-1-戊烯。
(8)经优化切割收集洗脱液,使用真空低温旋转蒸发干燥(旋蒸的工艺参数为:水浴温度为60℃、旋蒸的真空度为0.01Mpa,得到剩余体积量1~2mL的浓缩样品。
(9)将(8)制备的浓缩样品分别使用GCMS和核磁氢谱检测,得到的杂质质谱图如图8所示,得到的杂质氢谱图如图9所示,获得杂质分子结构信息,根据图8确定杂质为1-苯基-1-戊烯,根据图9确定杂质为1-苯基-1-戊烯。
以上所述仅是本发明的优选实施方式,应当指出,对于本技术领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以做出若干改进和润饰,这些改进和润饰也应视为本发明的保护范围。
Claims (3)
1.碳酸酯溶剂中杂质的分离与检测方法,其特征在于,包括如下步骤:
1)采用反相色谱对待测溶剂进行层析、梯度洗脱和等度洗脱,得到反相洗脱液和反相色谱图;
1.1)使用C18反相制备柱,规格为10μm*9.4*250mm,对待测样品进行分析,UV=200~450nm,流速=4mL/min,洗脱液为乙腈和水的混合溶液,从两者起始比为V乙腈:V水=5:95到8分钟后为V乙腈:V水=100:0的梯度程序洗脱样品,再使用纯乙腈等度洗脱2分钟,得到色谱图;
1.2)使用C18反相制备柱,规格为10μm*9.4*250mm,ELSD参数:漂移管温度105℃,气体流量2.8mL/min,流速=4mL/min,洗脱液为乙腈和水的混合溶液,从两者起始比为V乙腈:V水=2:8到8分钟后为V乙腈:V水=10:0的梯度程序洗脱样品,再使用纯乙腈等度洗脱2分钟,得到色谱图;
2)采用正相色谱对待测溶剂进行层析、梯度洗脱和等度洗脱,得到正相洗脱液和正相色谱图;
使用正相制备硅胶柱,柱型号为250*20mm*10μm,UV=200~450nm,流速=4mL/min,洗脱液为二氯甲烷和正己烷的混合溶液,从两者起始比为V正己烷:V二氯甲烷=1:9到8分钟后为V正己烷:V二氯甲烷=10:0的梯度程序洗脱样品,再使用纯正己烷等度洗脱2分钟,得到色谱图;
3)分别对所述步骤1)和2)的反相洗脱液和正相洗脱液进行切割,对切割后的反相洗脱液和正相洗脱液进行真空冷冻干燥和/或真空旋转蒸发干燥,得到反相洗脱液浓缩样品和正相洗脱液浓缩样品;
4)将所述步骤3)的反相洗脱液浓缩样品和正相洗脱液浓缩样品分别使用GCMS和核磁氢谱进行检测分析,得到杂质分子的结构信息;步骤1.1)确定的杂质为2-甲基-2-戊烯醛;步骤1.2)确定的杂质为二缩三乙二醇;步骤2)确定的杂质为1-苯基-1-戊烯;
所述步骤1)和2)没有时间顺序的限定;
碳酸酯类溶剂为碳酸乙烯酯、碳酸丙烯酯、碳酸二甲酯、碳酸二乙酯以和碳酸甲乙酯。
2.根据权利要求1所述的分离与检测方法,其特征在于,所述步骤3)中基于加大1~100倍体积过载量而不超过柱容量的馏分收集来进行切割,即100μL到10mL的样品量。
3.根据权利要求1所述的分离与检测方法,其特征在于,所述步骤3)中真空冷冻干燥时的工艺参数为:物料厚度1~100mm,干燥室真空度0.01~0.1Mpa,干燥时间1~48h;所述真空旋转蒸发干燥的工艺参数为:水浴温度30~60℃,旋蒸的真空度为0~0.09Mpa。
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