CN106432333A - 一种含硫磷酸酯类离子液体及其制备方法和应用 - Google Patents
一种含硫磷酸酯类离子液体及其制备方法和应用 Download PDFInfo
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Abstract
本发明公开了一种含硫磷酸酯类离子液体，该离子液体为三己基十四烷基膦O,O′‑二乙基二硫代磷酸酯，其结构式如下：
Description
技术领域
本发明涉及一种含硫磷酸酯类离子液体及其制备方法和应用。
背景技术
随着现代工业的技术发展、进步，机械设备不断向高速、重载和高精度的方向发展。机械设备的飞速发展对其所使用润滑油脂的服役性能提出了更高层次的需求。与此同时，石油资源危机及矿物润滑油带来的环境污染问题越来越受到人们的重视。合成酯类润滑油具有氧化安定性好、热稳定性高、黏温性能和低温性能好、润滑性能优和可生物降解性能高等优点，被广泛用做航空发动机油、内燃机油、压缩机油、冷冻机油、高速齿轮油、金属加工液以及液压油等，是目前应用最广泛的合成油之一。
添加剂是润滑油的精髓，直接关系到润滑油功能的实现和保持。然而，值得注意的是，目前常用的添加剂主要针对矿物基础油设计和使用，而针对合成润滑油特别是酯类合成基础油的减摩、抗磨、极压添加剂的研究较少。目前，商品化的只有磷酸三甲酚酯（TCP）被用作多元醇酯类的润滑添加剂。但是，TCP具有很大的毒性而限制了它的大量使用。
根据文献调研，Anthony E. Somers等（Anthony E. Somers et al.，ACS Appl. Mater. Interfaces, 2013, 5, 11544-11553）合成并考察了十多种不同结构的膦、咪唑和吡啶作为阳离子的离子液体在季戊四醇酯和三羟甲基丙烷酯中的溶解度及摩擦学性能，结果表明几种膦基阳离子离子液体在这两种多元醇酯中表现出一定的减摩抗磨性能。InésOtero等（Inés Otero et al.，ACS Appl. Mater. Interfaces, 2014, 6, 13115-13128）研究了八种油溶性离子液体作为三羟甲基丙烷油酸酯（TMPTO）润滑油添加剂时的减摩抗磨性能，且比较得出其性能优于常用极压抗磨添加剂二烷基二硫代磷酸锌（ZDDP）。Lili Zhu等（Lili Zhu et al.，Tribol. Int. (2016), http://dx.doi.org/10.1016/j.triboint.2016.03.004）合成了一种双酚AF基化合物，结果表明此化合物可以与季戊四醇油酸酯（PETO）和三羟甲基丙烷油酸酯（TMPTO）混溶，并且在高温200 ℃和150 ℃时表现出优异的减摩抗磨性能。除此之外，相关的针对高温多元醇酯类润滑油脂的摩抗磨添加剂的文献几乎很少。
发明内容
本发明的目的在于提供一种含硫磷酸酯类离子液体及其制备方法和应用。
一种含硫磷酸酯类离子液体，其特征在于该离子液体为三己基十四烷基膦O,O′-二乙基二硫代磷酸酯（记作TTP-DDP），其结构式如下：
。
如上所述含硫磷酸酯类离子液体的制备方法，其特征在于具体步骤为：将十四烷基三己基溴化膦（TTP-Br）与O,O′-二乙基二硫代磷酸酯在正己烷中混合，然后加入KOH水溶液和蒸馏水，在28-40℃下搅拌5-48 h，随后分出有机相，用二次蒸馏水洗涤三次，旋蒸除去正己烷，并将产物真空干燥，得到浅黄色粘稠状液体，即离子液体三己基十四烷基膦O,O′-二乙基二硫代磷酸酯。
所述十四烷基三己基溴化膦与O,O′-二乙基二硫代磷酸酯的摩尔比为1:1~1:1.5。
所述KOH水溶液中的KOH与十四烷基三己基溴化膦（TTP-Br）的摩尔比为1:1~1:1.5。
如上所述含硫磷酸酯类离子液体作为高温多元醇酯类润滑油减摩抗磨添加剂的应用。
所述含硫磷酸酯类离子液体添加到季戊四醇油酸酯（PETO）中的添加量为1 wt%～5 wt%，最佳添加量为4 wt%，在200 ℃具有优异的减摩抗磨性能。
所述含硫磷酸酯类离子液体添加到三羟甲基丙烷油酸酯（TMPTO）中的添加量为1wt%～5wt%，最佳添加量为4 wt%，在200 ℃具有显著的减摩抗磨性能。
本发明所述含硫磷酸酯类离子液体添加到季戊四醇油酸酯（PETO）和三羟甲基丙烷油酸酯（TMPTO）中，其减摩抗磨性能显著优于TCP。
附图说明
图1为本发明所述硫磷酸酯离子液体（记作TTP-DDP）的热分解温度曲线。
图2为浓度分别为0 wt%、1 wt%、2 wt%、3 wt%、4 wt%和5 wt%的TTP-DDP加入到季戊四醇油酸酯（PETO）中在SRV-IV 微振动摩擦磨损试验机上于200 ℃，200 N，频率50 Hz，载荷振幅1 mm的工况下长磨30 min时摩擦系数随时间变化的关系曲线。
图3为浓度分别为0 wt%、1 wt%、2 wt%、3 wt%、4 wt%和5 wt%的TTP-DDP加入到季戊四醇油酸酯（PETO）中在SRV-IV 微振动摩擦磨损试验机上于200 ℃，200 N，频率50 Hz，载荷振幅1 mm的工况下长磨30 min后下试样钢块上磨斑的磨损体积。
图4为浓度分别为3 wt% TCP和4 wt% TTP-DDP加入到季戊四醇油酸酯（PETO）中在SRV-IV 微振动摩擦磨损试验机上于200 ℃，200 N，频率50 Hz，载荷振幅1 mm的工况下长磨30 min时摩擦系数随时间变化的关系曲线。
图5为浓度分别为0 wt%、1 wt%、2 wt%、3 wt%、4 wt%和5 wt%的TTP-DDP加入到三羟甲基丙烷油酸酯（TMPTO）中在SRV-IV 微振动摩擦磨损试验机上于200 ℃，200 N，频率50Hz，载荷振幅1 mm的工况下长磨30 min时摩擦系数随时间变化的关系曲线。
图6为浓度分别为0 wt%、1 wt%、2 wt%、3 wt%、4 wt%和5 wt%的TTP-DDP加入到三羟甲基丙烷油酸酯（TMPTO）中在SRV-IV 微振动摩擦磨损试验机上于200 ℃，200 N，频率50Hz，载荷振幅1mm的工况下长磨30 min后下试样钢块上磨斑的磨损体积。
图7为浓度分别为4 wt% TCP和4 wt% TTP-DDP加入到三羟甲基丙烷油酸酯（TMPTO）中在SRV-IV 微振动摩擦磨损试验机上于200 ℃，200 N，频率50 Hz，载荷振幅1 mm的工况下长磨30 min时摩擦系数随时间变化的关系曲线。
具体实施方式
实施例1
在150 mL三口烧瓶中加入29.67 g（0.05 mol）十四烷基三己基溴化膦，60 g 正己烷，之后加入10.36 g （0.05 mol）O,O′-二乙基二硫代磷酸酯，然后加入KOH水溶液（KOH 0.05mol）和蒸馏水，室温（25 ℃）下连续搅拌反应8 h。反应完后，分离有机相，用二次水洗涤，95℃下干燥24 h，得到25.40 g浅黄色粘稠状液体，即三己基十四烷基膦O,O′-二乙基二硫代磷酸酯（记作TTP-DDP），分子量为668.5，产率76 %。
实施例2
在150 mL三口烧瓶中加入29.67 g（0.05 mol）十四烷基三己基溴化膦，60 g 正己烷，之后加入10.36 g （0.05 mol）O,O′-二乙基二硫代磷酸酯，然后加入KOH水溶液（KOH 0.05mol）和蒸馏水，30 ℃下连续搅拌反应16 h。反应完后，分离有机相，用二次水洗涤，95 ℃下干燥24 h，得到27.41 g浅黄色粘稠状液体，即三己基十四烷基膦O,O′-二乙基二硫代磷酸酯（记作TTP-DDP），分子量为668.5，产率82 %。
实施例3
在150 mL三口烧瓶中加入29.67 g（0.05 mol）十四烷基三己基溴化膦，60 g 正己烷，之后加入10.36 g （0.05 mol）O,O′-二乙基二硫代磷酸酯，然后加入KOH水溶液（KOH 0.05mol）和蒸馏水，38℃下连续搅拌反应48 h。反应完后，分离有机相，用二次水洗涤，95 ℃下干燥24 h，得到30.08 g浅黄色粘稠状液体，即三己基十四烷基膦O,O′-二乙基二硫代磷酸酯（记作TTP-DDP），分子量为668.5，产率90 %。
热稳定性评价
热稳定性是通过STA 449 C Jupiter simultaneous TG-DSC测定。将实施例1制备的三己基十四烷基膦O,O′-二乙基二硫代磷酸酯（记作TTP-DDP）3mg放入样品池中，测试温度从20-800℃，温度增加速率是10℃/min，在空气环境下测定，结果如图1所示。可以看出TTP-DDP在低于300℃时未表现出任何质量损失，表明该物质具有非常好的热稳定性能。
产物的摩擦学性能评价：
将实施例3制备的浓度分别为0 wt%、1 wt%、2 wt%、3 wt%、4 wt%和5 wt%的TTP-DDP加入到季戊四醇油酸酯（PETO）中，超声使其混合均匀；浓度分别为0 wt%、1 wt%、2 wt%、3wt%、4 wt%和5 wt%的TTP-DDP加入到三羟甲基丙烷油酸酯（TMPTO）中，超声使其混合均匀，配制成润滑剂，综合评价其摩擦学性能：
1. 采用德国Optimol油脂公司生产的SRV-IV 微动摩擦磨损试验机测试浓度分别为0wt%、1 wt%、2 wt%、3 wt%、4 wt%和5 wt%的TTP-DDP加入到季戊四醇油酸酯（PETO）中，在200℃，频率50 Hz，振幅1 mm，载荷200 N的工况下长磨30 min时的摩擦系数f，试验所用钢球为Φ= 10 mm的GCr15轴承钢，下试样为Φ 24×7.9 mm的GCr15钢块，结果见附图2和3。由图可以看出，在200℃高温下，这种离子液体作为添加剂能很好的润滑钢-钢摩擦副，摩擦系数大幅度降低，减摩效果极为明显，并且TTP-DDP在PETO中的减摩抗磨效果优于TCP。
2. 采用德国Optimol油脂公司生产的SRV-IV 微动摩擦磨损试验机测试浓度分别为0 wt%、1 wt%、2 wt%、3 wt%、4 wt%和5 wt%的TTP-DDP加入到三羟甲基丙烷油酸酯（TMPTO）中，在200 ℃，频率50 Hz，振幅1 mm，载荷200 N的工况下长磨30 min时的摩擦系数f，试验所用钢球为Φ = 10 mm的GCr15轴承钢，下试样为Φ 24 × 7.9 mm的GCr15钢块，结果见附图5和6。由图可以看出，在200 ℃高温下，这种离子液体作为添加剂能很好的润滑钢-钢摩擦副，摩擦系数大幅度降低，减摩抗磨效果极为明显，并且TTP-DDP在TMPTO中的减摩抗磨效果显著优于TCP。
3. 采用MicroXAM 3D 非接触的表面轮廓测试仪测试浓度分别为0 wt%、1 wt%、2wt%、3 wt%、4 wt%和5 wt%的TTP-DDP加入到季戊四醇油酸酯（PETO）中，在200 ℃，频率50Hz，振幅1 mm，载荷200 N的工况下长磨30 min后下试样钢块上磨斑的摩擦体积，试验所用钢球为Φ = 10 mm的GCr15轴承钢，下试样为Φ 24 × 7.9 mm的GCr15钢块，结果见附图4。由图可以看出，在200 ℃高温下，这种离子液体作为添加剂能很好的润滑钢-钢摩擦副，抗磨效果极为明显，并且TTP-DDP在PETO中的抗磨效果显著优于TCP。
4. 采用MicroXAM 3D 非接触的表面轮廓测试仪测试浓度分别为0 wt%、1 wt%、2wt%、3 wt%、4 wt%和5 wt%的TTP-DDP加入到三羟甲基丙烷油酸酯（TMPTO）中，在200 ℃，频率50 Hz，振幅1 mm，载荷200 N的工况下长磨30 min后下试样钢块上磨斑的磨损体积，试验所用钢球为Φ = 10 mm的GCr15轴承钢，下试样为Φ 24 × 7.9 mm的GCr15钢块，结果见附图7。由图可以看出，在200℃高温下，这种离子液体作为添加剂对钢-钢摩擦副有润滑效果，磨损体积明显减小，并且TTP-DDP在TMPTO中的抗磨效果优于TCP。
Claims (9)
1.一种含硫磷酸酯类离子液体，其特征在于该离子液体为三己基十四烷基膦O,O′-二乙基二硫代磷酸酯，其结构式如下：
。
2.如权利要求1所述含硫磷酸酯类离子液体的制备方法，其特征在于具体步骤为：将十四烷基三己基溴化膦与O,O′-二乙基二硫代磷酸酯在正己烷中混合，然后加入KOH水溶液和蒸馏水，在28-40℃下搅拌5-48 h，随后分出有机相，用二次蒸馏水洗涤三次，旋蒸除去正己烷，并将产物真空干燥，得到浅黄色粘稠状液体，即离子液体三己基十四烷基膦O,O′-二乙基二硫代磷酸酯。
3.如权利要求2所述的制备方法，其特征在于所述十四烷基三己基溴化膦与O,O′-二乙基二硫代磷酸酯的摩尔比为1:1~1:1.5。
4.如权利要求2所述的制备方法，其特征在于所述KOH水溶液中的KOH与十四烷基三己基溴化膦的摩尔比为1:1~1:1.5。
5.如权利要求1所述含硫磷酸酯类离子液体作为高温多元醇酯类润滑油减摩抗磨添加剂的应用。
6.如权利要求5所述的应用，其特征在于所述含硫磷酸酯类离子液体添加到季戊四醇油酸酯中的添加量为1 wt%～5 wt%。
7.如权利要求6所述的应用，其特征在于所述含硫磷酸酯类离子液体添加到季戊四醇油酸酯中的添加量为4 wt%。
8.如权利要求5所述的应用，其特征在于所述含硫磷酸酯类离子液体添加到三羟甲基丙烷油酸酯中的添加量为1wt%～5wt%。
9.如权利要求8所述的应用，其特征在于所述含硫磷酸酯类离子液体添加到三羟甲基丙烷油酸酯中的添加量为4 wt%。
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