CN106167466A - 一种含天然脂环结构的离子液体及其制备方法和应用 - Google Patents

一种含天然脂环结构的离子液体及其制备方法和应用 Download PDF

Info

Publication number
CN106167466A
CN106167466A CN201610592503.1A CN201610592503A CN106167466A CN 106167466 A CN106167466 A CN 106167466A CN 201610592503 A CN201610592503 A CN 201610592503A CN 106167466 A CN106167466 A CN 106167466A
Authority
CN
China
Prior art keywords
methylimidazole
ionic liquid
alkyl
bromination
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201610592503.1A
Other languages
English (en)
Other versions
CN106167466B (zh
Inventor
高平
刘维民
冯大鹏
孙晓军
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lanzhou Institute of Chemical Physics LICP of CAS
Original Assignee
Lanzhou Institute of Chemical Physics LICP of CAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lanzhou Institute of Chemical Physics LICP of CAS filed Critical Lanzhou Institute of Chemical Physics LICP of CAS
Priority to CN201610592503.1A priority Critical patent/CN106167466B/zh
Publication of CN106167466A publication Critical patent/CN106167466A/zh
Application granted granted Critical
Publication of CN106167466B publication Critical patent/CN106167466B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/19—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38—Heterocyclic nitrogen compounds
    • C10M133/44—Five-membered ring containing nitrogen and carbon only
    • C10M133/46—Imidazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/04—Well-defined cycloaliphatic compounds
    • C10M2203/045—Well-defined cycloaliphatic compounds used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/044—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • C10M2215/224—Imidazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/64—Environmental friendly compositions

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)

Abstract

本发明公开了一种含天然脂环结构的离子液体，该离子液体的分子式为[CH3C3H3N2CnH2n+1]X，（X=C6H10NO2或C10H15O4S），化学名称为1‑烷基‑3‑甲基咪唑1‑氨基环戊烷甲酸盐或1‑烷基‑3‑甲基咪唑樟脑磺酸盐。本发明利用季铵盐离子交换法合成含天然脂环结构离子液体，所选的阴离子原料是天然产物的衍生物，无需特殊制备，不用先期功能化；可以缩短反应流程；反应操作简单，可控性强。该离子液体作为减摩添加剂应用于烷基环戊烷润滑油，或以烷基环戊烷为基础油的润滑脂。

Description

一种含天然脂环结构的离子液体及其制备方法和应用
技术领域
本发明涉及一种含天然脂环结构的离子液体及其制备方法和应用。该离子液体作为减摩添加剂应用于烷基环戊烷润滑油，或以烷基环戊烷为基础油的润滑脂。
背景技术
多烷基化环戊烷(MACs)具有低的挥发性、高的热稳定性和化学稳定性，在空间机械的润滑上有很大的应用潜力，并已取得了空间应用的实际经验。(D. J. Carre, C. G.Kalogeras, S. V. Didziulis, R. Bauer. Recent experience with synthetichydrocarbon lubricants for spacecraft applications. Aerospace Corp., Report TR(5935)-3, June 1995；W. R. Jones, Jr., A. K. Poslowski. Evaluation ofseveral space lubricants using a vacuum four-ball tribometer. NASA TM- 1998-208654, October 1998.)。
多烷基化环戊烷的核心五元环使这类化合物具有高的热稳定性和化学稳定性。但是，由于此类化合物属于非极性化合物，对基底的吸附力较弱，摩擦过程中边界润滑膜容易被破坏，因此其极压性能相对比较弱。
离子液体是一类强极性的化合物，有着独特的溶解性能，高热稳定性和极低的蒸气压。研究显示，离子液体结构中的不同官能基团能显著改变其性能。如果利用离子液体所特有的“可设计性”，通过化学合成的方法在离子液体中引入五元环，使取代环戊烷和离子液体各自的优异性能相结合，将有利于增强多烷基化环戊烷与基底的吸附能力，改进其摩擦学性能。
发明内容
本发明的目的在于提供一种含天然脂环结构的离子液体及其制备方法和应用。
一种含天然脂环结构的离子液体，其特征在于该离子液体的结构式如式()所示，分子式为[CH3C3H3N2CnH2n+1]X，X为C6H10NO2或C10H15O4S，化学名称为1-烷基-3-甲基咪唑1-氨基环戊烷甲酸盐或1-烷基-3-甲基咪唑樟脑磺酸盐，
式(I) ，
其中，n为4～10的整数。
本发明化合物的合成方法如式(Ⅱ)所示：
式(Ⅱ)
其中，n为4～10的整数。
本发明通过溴化1-烷基-3-甲基咪唑和1-氨基环戊烷甲酸或樟脑磺酸反应，得到含天然脂环结构的离子液体。
一种含天然脂环结构的离子液体的制备方法，其特征在于以溴化1-烷基-3-甲基咪唑和1-氨基环戊烷甲酸或樟脑磺酸为原料，反应温度20～90℃，反应时间2～10小时，反应结束后洗涤、干燥生成物得到目标产物。
所述溴化1-烷基-3-甲基咪唑与1-氨基环戊烷甲酸或樟脑磺酸的摩尔比为1: 1.1~3.6。
所述溴化1-烷基-3-甲基咪唑为溴化1-丁基-3-甲基咪唑、溴化1-己基-3-甲基咪唑、溴化1-辛基-3-甲基咪唑或溴化1-癸基-3-甲基咪唑。
在实验室中，我们具体的制备过程是：在圆底烧瓶中，加入溴化1-烷基-3-甲基咪唑，在搅拌过程中，加入1-氨基环戊烷甲酸或樟脑磺酸的水溶液，于20~90℃，搅拌1~5小时，用二氯甲烷萃取三次，二氯甲烷相用水洗涤三次后无水硫酸镁干燥过夜，减压蒸去溶剂，再在100℃/0.1 mmHg减压抽1小时，除去可能含有的水份，得到目标产物。
上述离子液体作为减摩添加剂以超声分散于烷基环戊烷基础油中。以润滑油总重为基准，离子液体添加量为0.1~2.0wt%。
文献报道利用离子液体所特有的“可设计性”，通过功能化阴阳离子，可以得到预期性能的离子液体。近年来，针对阳离子的功能化有大量文献报道，但是较少涉及针对于阴离子的功能化研究。另外，为了实现离子液体的功能化，不可避免地会引入一些较大的基团，必然会提高离子液体的熔点，因而限制了功能化离子液体适用的范围。
本发明的新颖之处在于：利用离子液体所特有的“可设计性”，通过化学合成的方法在离子液体中引入取代的五元环。离子液体本身带有负电荷，在摩擦过程中很容易与摩擦副的正电荷点结合，形成很稳定的过渡态，而且这种过渡态的构型非常有序，并能保持一定的厚度，在摩擦过程中起到减摩抗磨的作用，因此其摩擦学性能很好。咪唑部分杂环中的氮原子有利于提高共扼杂环的热稳定性，并赋予润滑剂良好的极压抗磨性能和高闪点。所选的阴离子原料是天然产物的衍生物，无需特殊制备，不用先期功能化，操作简单；可以缩短反应流程，可控性强。因为是不对称阴离子，其最终产物在室温（25℃）下呈淡黄色或黄色的粘稠透明液体，20℃粘度280~450 mm2·s-1，粘度指数110~130，倾点<-30℃，初始热分解温度﹥350℃，该化合物具有很宽的液相温度范围、优异的高低温性能和良好的粘温性能。
本发明的优点在于：
(1) 随着人们环境保护意识的日益增加，对化工产品的环保性能提出了更高的要求。本发明的离子液体，阴离子是天然产物的衍生物，在微生物作用下易降解，从而达到环保要求。
(2) 通过化学合成的方法将取代环戊烷和离子液体二者的优异性能相结合，化合物具有很宽的液相温度范围、优异的高低温性能、良好的粘温性能。由于分子结构的相似性，化合物与取代环戊烷有良好的相容性，可以作为减摩添加剂应用于烷基环戊烷润滑油，或以烷基环戊烷为基础油的润滑脂。
本发明所述润滑剂的摩擦学性能采用模拟真空条件摩擦磨损试验机评价。实验条件：真空度，10-4Pa；载荷，3N；转速，300 rpm；时间，1h。实验上试球为Si3N4球或9Cr18钢球，下试盘为半径24mm的GCr15钢盘。
具体实施方式
本发明可通过如下实施例进一步说明，以下实施例仅用于说明本发明的具体实施方案，而不是用于限制本方法的应用。
实施例1
合成1-丁基-3-甲基咪唑1-氨基环戊烷甲酸盐。
在圆底烧瓶中，加入52.56g(0.24mol)溴化1-丁基-3-甲基咪唑，在搅拌过程中，加入34.8g(0.27mol) 1-氨基环戊烷甲酸水溶液，于40℃，搅拌2小时，用二氯甲烷萃取三次，二氯甲烷溶液再用蒸馏水洗涤三次，之后用无水硫酸镁干燥过夜，减压蒸去溶剂，再在100℃/0.1 mmHg减压抽1小时，得到目标产品。
实施例2
合成1-己基-3-甲基咪唑1-氨基环戊烷甲酸盐。
在圆底烧瓶中，加入59.28g(0.24mol) 溴化1-己基-3-甲基咪唑，在搅拌过程中，加入36.1g(0.28mol) 1-氨基环戊烷甲酸水溶液，于40℃，搅拌3小时。其余同实施例1。
实施例3
合成1-辛基-3-甲基咪唑1-氨基环戊烷甲酸盐。
在圆底烧瓶中，加入66.00g(0.24mol) 溴化1-辛基-3-甲基咪唑，在搅拌过程中，加入38.7g(0.30mol) 1-氨基环戊烷甲酸水溶液，于50℃，搅拌4小时。其余同实施例1。
实施例4
合成1-癸基-3-甲基咪唑1-氨基环戊烷甲酸盐。
在圆底烧瓶中，加入72.72g(0.24mol) 溴化1-癸基-3-甲基咪唑，在搅拌过程中，加入41.3g(0.32mol) 1-氨基环戊烷甲酸水溶液，于50℃，搅拌4小时。其余同实施例1。
实施例5
合成1-丁基-3-甲基咪唑樟脑磺酸盐。
在圆底烧瓶中，加入52.56g(0.24mol)溴化1-丁基-3-甲基咪唑，在搅拌过程中，加入62.64g(0.27mol) 樟脑磺酸水溶液，于40℃，搅拌2小时。其余同实施例1。
实施例6
合成1-己基-3-甲基咪唑樟脑磺酸盐。
在圆底烧瓶中，加入59.28g(0.24mol) 溴化1-己基-3-甲基咪唑，在搅拌过程中，加入64.96g(0.28mol) 樟脑磺酸水溶液，于40℃，搅拌3小时。其余同实施例1。
实施例7
合成1-辛基-3-甲基咪唑樟脑磺酸盐。
在圆底烧瓶中，加入66.00g(0.24mol) 溴化1-辛基-3-甲基咪唑，在搅拌过程中，加入69.60g(0.30mol) 樟脑磺酸水溶液，于50℃，搅拌4小时。其余同实施例1。
实施例8
合成1-癸基-3-甲基咪唑樟脑磺酸盐。
在圆底烧瓶中，加入72.72g(0.24mol) 溴化1-癸基-3-甲基咪唑，在搅拌过程中，加入74.24g(0.32mol) 樟脑磺酸水溶液，于50℃，搅拌4小时。其余同实施例1。
实施例9
将实施例1~8的离子液体分别以质量百分数1.5%、1.0%、0.6%、0.4%、1.4%、0.8%、0.5%、0.3%的加剂量超声分散于烷基环戊烷基础油中，采用模拟真空条件摩擦磨损试验机评价它们的摩擦学性能，结果列于表1。
表1 实施例9实验结果
表1中的结果表明，本发明的化合物应用于烷基环戊烷基础油中具有良好的减摩性能。

Claims (6)

1.一种含天然脂环结构的离子液体，其特征在于该离子液体的结构式如式()所示，分子式为[CH3C3H3N2CnH2n+1] X，X为 C6H10NO2或C10H15O4S，化学名称为1-烷基-3-甲基咪唑1-氨基环戊烷甲酸盐或1-烷基-3-甲基咪唑樟脑磺酸盐，
式(I) ，其中，n为4～10的整数。
2.如权利要求1所述的含天然脂环烷结构的离子液体的制备方法，其特征在于以溴化1-烷基-3-甲基咪唑和1-氨基环戊烷甲酸或樟脑磺酸为原料，反应温度20～90℃，反应时间2～10小时，反应结束后洗涤、干燥生成物得到目标产物。
3.如权利要求2所述的制备方法，其特征在于所述溴化1-烷基-3-甲基咪唑与1-氨基环戊烷甲酸或樟脑磺酸的摩尔比为1: 1.1~3.6。
4.如权利要求2或3所述的制备方法，其特征在于所述溴化1-烷基-3-甲基咪唑为溴化1-丁基-3-甲基咪唑、溴化1-己基-3-甲基咪唑、溴化1-辛基-3-甲基咪唑或溴化1-癸基-3-甲基咪唑。
5.如权利要求1所述含天然脂环烷结构的离子液体作为减摩添加剂以超声分散于烷基环戊烷基础油中的应用。
6.如权利要求5所述的应用，其特征在于以润滑油总重为基准，离子液体添加量为0.1~2.0wt%。
CN201610592503.1A 2016-07-26 2016-07-26 一种含天然脂环结构的离子液体及其制备方法和应用 Active CN106167466B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610592503.1A CN106167466B (zh) 2016-07-26 2016-07-26 一种含天然脂环结构的离子液体及其制备方法和应用

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610592503.1A CN106167466B (zh) 2016-07-26 2016-07-26 一种含天然脂环结构的离子液体及其制备方法和应用

Publications (2)

Publication Number Publication Date
CN106167466A true CN106167466A (zh) 2016-11-30
CN106167466B CN106167466B (zh) 2019-04-05

Family

ID=58065561

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610592503.1A Active CN106167466B (zh) 2016-07-26 2016-07-26 一种含天然脂环结构的离子液体及其制备方法和应用

Country Status (1)

Country Link
CN (1) CN106167466B (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113388434A (zh) * 2020-03-13 2021-09-14 中国石油化工股份有限公司 极压抗磨剂组合物、极压抗磨剂及空间润滑剂

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102101842A (zh) * 2009-12-18 2011-06-22 中国科学院兰州化学物理研究所 一种具有抗磨性的萘基功能化离子液体及其制备方法
CN103343030A (zh) * 2013-07-09 2013-10-09 陈立功 一种功能化离子液体润滑剂
CN103666643A (zh) * 2012-09-14 2014-03-26 中国科学院兰州化学物理研究所 阴离子功能化的咪唑离子液体润滑油添加剂及其制备方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102101842A (zh) * 2009-12-18 2011-06-22 中国科学院兰州化学物理研究所 一种具有抗磨性的萘基功能化离子液体及其制备方法
CN103666643A (zh) * 2012-09-14 2014-03-26 中国科学院兰州化学物理研究所 阴离子功能化的咪唑离子液体润滑油添加剂及其制备方法
CN103343030A (zh) * 2013-07-09 2013-10-09 陈立功 一种功能化离子液体润滑剂

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
KAORU NOBUOKA，ET AL.: "Camphor Ionic Liquid: Correlation between Stereoselectivity and Cation-Anion Interaction", 《J.ORG.CHEM.》 *
丁玲等: "离子液体作为新型润滑材料的研究进展", 《化学进展》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113388434A (zh) * 2020-03-13 2021-09-14 中国石油化工股份有限公司 极压抗磨剂组合物、极压抗磨剂及空间润滑剂
CN113388434B (zh) * 2020-03-13 2022-07-15 中国石油化工股份有限公司 极压抗磨剂组合物、极压抗磨剂及空间润滑剂

Also Published As

Publication number Publication date
CN106167466B (zh) 2019-04-05

Similar Documents

Publication Publication Date Title
Mahrova et al. Pyridinium based dicationic ionic liquids as base lubricants or lubricant additives
Kagimoto et al. Effect of tetrabutylphosphonium cation on the physico-chemical properties of amino-acid ionic liquids
Cai et al. Alkyl imidazolium ionic liquids as friction reduction and anti-wear additive in polyurea grease for steel/steel contacts
Song et al. Green ionic liquid lubricants prepared from anti-inflammatory drug
Shakil Hussain et al. Amido-amine-based cationic gemini surfactants: thermal and interfacial properties and interactions with cationic polyacrylamide
Wang et al. Conductive lubricating grease synthesized using the ionic liquid
Handy Ionic Liquids: Current State of the Art
CN108707496A (zh) 一种高承载二维二硫化钼-二元离子液体复合润滑薄膜及制备方法
Zhou et al. Synthesis of Bis [N, N′-(alkylamideethyl) ethyl] triethylenediamine bromide surfactants and their oilfield application investigation
Verma et al. Ionic liquids as green and smart lubricant application: an overview
WO2016129148A1 (ja) 潤滑剤組成物及びその利用、並びに脂肪族エーテル化合物
CN105669497B (zh) 氨基酸衍生物有机小分子凝胶因子及其制备方法和应用
Poopalam et al. Lipid‐derived monoamide as phase change energy storage materials
Mousli et al. Synthesis and some surface properties of glycine-based surfactants
Fan et al. An investigation on the friction and wear properties of perfluorooctane sulfonate ionic liquids
CN106167466A (zh) 一种含天然脂环结构的离子液体及其制备方法和应用
CN103173261B (zh) 羟基咪唑功能化离子液体润滑剂及其制备方法
Fang et al. The superior lubricating performance and unique mechanism of oil-soluble protic ionic liquids with short alkyl chains
CN102716693A (zh) 一种腰果基非离子表面活性剂及其制备方法
Kraus et al. A direct synthesis of renewable sulfonate-based surfactants
CN106187759B (zh) 格尔伯特醇环戊烷羧酸酯润滑剂及其制备方法
Chen et al. Novel phosphate organic guanidine salt water-based additive with integrated anti-friction, anti-wear and anti-corrosion properties
Yoshida et al. Gelation by novel aprotic low-molecular-mass organic gelators based on a gemini 4-[2-(perfluorobutyl) ethylthio] phenoxy unit
CN106187902A (zh) 一种含烷基萘结构离子液体及其制备方法和应用
Fang et al. Novel binary oil-soluble ionic liquids with high lubricating performance

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant