CN115108973A - 一种电中性离子液体及其制备方法 - Google Patents
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Abstract
本发明涉及一种电中性离子液体及其制备方法,具体地涉及式(I)所示化合物、或其盐、或其立体异构体。本发明的含氟电中性离子液体与对比例相对比,可以有效提高农药微滴在植物表面的附着量和附着牢固度,可用于农药领域。
Description
技术领域
本发明属于化学技术领域,具体涉及一种电中性离子液体及其制备方法。
背景技术
离子液体是低熔点盐,通常由有机阳离子和无机/有机阴离子组成。离子液体的物理化学性质可通过改变阴阳离子或对阴阳离子进行修饰调控。离子液体具有许多优异的理化特性:(1)蒸气压极低;(2)耐热性高,液态温度范围宽(可达300℃);(3)难燃性;(4)化学稳定性高,且对其它极性物质的溶解性能优良;(5)电化学窗口宽,分解电压高(可达到6V);(6)物理化学性质可通过对阳离子的化学修饰或改变阴离子进行设计调节。离子液体的这些独特性能使得其得到逐步而广泛的应用。
到目前为止,虽然农药领域已经有多种离子液体被开发出来。但是,提高农药微滴在植物表面的附着量和附着牢固度的电中性离子液体的报道不多,通过分子结构设计,开发新型提高农药微滴在植物表面的附着量和附着牢固度的电中性离子液体仍然有很大的研究空间。
发明内容
本发明的目的是为了解决现有技术中存在的缺点,而提出的一种电中性离子液体及其制备方法。
针对上述目的,本发明提供以下技术方案:
第一方面,本发明提供了式(I)所示化合物、或其盐、或其立体异构体:
其中:
X选自亚烷基。
在一些优选的实施方案中,本发明的化合物为式(I)所示化合物、或其盐、或其立体异构体,其中:
X选自C3-12亚烷基;
进一步优选地,X选自亚丙基、亚丁基、亚戊基、亚正己基、亚正庚基、亚正辛基和亚正壬基。
在一些实施例中,式(I)化合物为以下化合物:
本发明第二方面提供了一种上述式(I)所示化合物的制备方法,其包括如下反应步骤:
1)将式(a)的化合物和4-吡啶酮溶于有机溶剂中,制得式(b)的化合物;
2)将式(b)的化合物与四氟乙烷-beta-磺内酯进行反应,制得式(I)的化合物。
在一些优选的实施方案中,所述式(a)的化合物和4-吡啶酮的摩尔量之比为1:1-1:2;更优选地,所述式(a)的化合物和4-吡啶酮的摩尔量之比为1:1.4-1:1.6;更优选地,所述式(a)的化合物和4-吡啶酮的摩尔量之比约为1:1.5。
在一些优选的实施方案中,所述式(b)的化合物和四氟乙烷-beta-磺内酯摩尔量之比为1:1-1:2;更优选地,所述式(b)的化合物和四氟乙烷-beta-磺内酯摩尔量之比为1:1-1:1.5;更优选地,所述式(b)的化合物和四氟乙烷-beta-磺内酯摩尔量之比为1:1.1-1:1.2。
在一些优选的实施方案中,根据式(I)所示化合物的制备方法,其中步骤1)中所述的有机溶剂选自四氢呋喃、乙腈、乙醇和乙酸乙酯中的一种或者多种。
本发明第三方面提供了上述式(I)所示化合物、或其盐、或其立体异构体在制备农药助剂中的用途。
在一些具体的实施方案中,本发明的所述农药助剂的应用,具体为将所述农药助剂添加到农药水溶液中。优选地,所述农药助剂与农药水溶液的质量比为1:500-1:4000;进一步优选地,所述农药助剂与农药水溶液的质量比为1:2000。
术语定义
为了能够更清楚地理解本发明的技术内容,下面对本发明的术语作进一步说明。
“亚烷基”指直链和支链的饱和的脂族烃基。“C6-12亚烷基”是指具有6至12个碳原子的亚烷基;亚烷基的非限制性的例子包括:亚丙基、亚丁基、亚戊基、亚正己基、亚1-乙基-2-甲基丙基、亚1,1,2-三甲基丙基、亚1,1-二甲基丁基、亚1,2-二甲基丁基、亚2,2-二甲基丁基、亚1,3-二甲基丁基亚、2-乙基丁基、亚2-甲基戊基、亚3-甲基戊基、亚4-甲基戊基、亚2,3-二甲基丁基、亚正庚基、亚2-甲基己基、亚3-甲基己基、亚4-甲基己基、亚5-甲基己基、亚2,3-二甲基戊基、亚2,4-二甲基戊基、亚2,2-二甲基戊基、亚3,3-二甲基戊基、亚2-乙基戊基、亚3-乙基戊基、亚正辛基、亚2,3-二甲基己基、亚2,4-二甲基己基、亚2,5-二甲基己基、亚2,2-二甲基己基、亚3,3-二甲基己基、亚4,4-二甲基己基、亚2-乙基己基、亚3-乙基己基、亚4-乙基己基、亚2-甲基-2-乙基戊基、亚2-甲基-3-乙基戊基、亚正壬基、亚2-甲基-2-乙基己基、亚2-甲基-3-乙基己基、亚2,2-二乙基戊基、亚正癸基、亚3,3-二乙基己基、亚2,2-二乙基己基,及其各种支链异构体。
与现有技术相比,本发明的有益效果是:
提供了一系列结构新颖的含氟电中性离子液体,其与不含氟的类似物相对比,可以有效提高农药微滴在植物表面的附着量和附着牢固度,可用于农药领域。
具体实施方式
下面代表性的实施例是为了更好地说明本发明,而非用于限制本发明的保护范围。以下实施例中使用的材料如无特殊说明均为商购获得。
实施例1
步骤1 1-(5-苯基戊基)4-吡啶酮的合成
将(5-溴正戊基)苯(22.7g,0.1mol)、4-吡啶酮(14.27g,0.15mol)溶于乙腈(200mL)中,在氮气下冰浴中搅拌1小时,室温下搅拌1小时,35℃下搅拌1天,45℃下搅拌2天。将反应溶液减压干燥,使得到的固体溶于氯仿。用饱和碳酸氢钠水溶液分液(3次),用硫酸镁干燥氯仿层后,蒸发干燥溶液。用乙醇-醚使粗产物重结晶,得到标题化合物。
步骤2
将步骤1得到的产物10g溶解于100mL脱水乙腈中,在搅拌的同时缓慢加入四氟乙烷-beta-磺内酯(55mmol,9.90g)。将其在氮气气氛下并在50℃下搅拌12小时。在室温下放置滤去析出的结晶。粗产物由乙醇-醚进行重结晶制得实施例1的化合物。MS m/z(ESI):422.1[M+H]+。
实施例2
制备方法同实施例1的制备方法,不同的是将(5-溴正戊基)苯替换为4-苯基-1-丁基溴,制得实施例2的化合物。MS m/z(ESI):408.1[M+H]+。
实施例3
制备方法同实施例1的制备方法,不同的是将(5-溴正戊基)苯替换为1-溴-6-苯基己烷,制得实施例3的化合物。MS m/z(ESI):436.1[M+H]+。
实施例4
制备方法同实施例1的制备方法,不同的是将(5-溴正戊基)苯替换为1-溴-7-苯基庚烷,制得实施例4的化合物。MS m/z(ESI):450.1[M+H]+。
实施例5
制备方法同实施例1的制备方法,不同的是将(5-溴正戊基)苯替换为1-溴-8-苯基辛烷,制得实施例5的化合物。MS m/z(ESI):464.1[M+H]+。
对比例1
制备方法同实施例1的制备方法,不同的是将四氟乙烷-beta-磺内酯替换为1,3-丙烷磺内酯,制得对比例1的化合物。MS m/z(ESI):364.2[M+H]+。
实验例
分别将实施例1-5及对比例1制得的化合物按质量比1:2000添加到先正达阿米西达2000倍水溶液中,分别量取体积为5μL的农药微滴在烟草叶片上,测量农药微滴在烟草叶片上的接触角;干燥后浸水12h,检测农药存留量,结果参见表1。
表1
由上表可见,本发明实施例1至5制备的农药助剂,按质量比1:2000添加到农药水溶液中,农药微滴在烟草叶片上的接触角介于30°-50°之间;干燥后浸水12h,农药存留量达到60%-88%,远优于对比例1的农药助剂。由此可知,通过本发明获得的农药助剂,能够显著提升药液的叶片表面附着量和附着牢固度,在农药减量使用领域应用前景广阔。
尽管以上已经对本发明作了详细描述,但是本领域技术人员理解,在不偏离本发明的精神和范围的前提下可以对本发明进行各种修改和改变。本发明的权利范围并不限于上文所作的详细描述,而应归属于权利要求书。
Claims (10)
2.根据权利要求1所述的式(I)所示化合物、或其盐、或其立体异构体,其特征在于,X选自C3-12亚烷基。
3.根据权利要求1所述的式(I)所示化合物、或其盐、或其立体异构体,其特征在于,X选自亚丙基、亚丁基、亚戊基、亚正己基、亚正庚基、亚正辛基和亚正壬基。
6.根据权利要求5所述的式(I)所示化合物的制备方法,其特征在于,所述式(a)的化合物和4-吡啶酮的摩尔量之比为1:1-1:2。
7.根据权利要求5所述的式(I)所示化合物的制备方法,其特征在于,所述式(b)的化合物和四氟乙烷-beta-磺内酯摩尔量之比为1:1-1:2。
8.根据权利要求5所述的式(I)所示化合物的制备方法,其特征在于,所述的有机溶剂选自四氢呋喃、乙腈、乙醇和乙酸乙酯中的一种或者多种。
9.根据权利要求1-4之任一项所述的式(I)所示化合物、或其盐、或其立体异构体在制备农药助剂中的用途。
10.根据权利要求9所述的用途,其特征在于,将所述农药助剂添加到农药水溶液中。
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