CN103173261B - Hydroxyl imidazole functionalized ionic liquid lubricant and preparation method thereof - Google Patents

Hydroxyl imidazole functionalized ionic liquid lubricant and preparation method thereof Download PDF

Info

Publication number
CN103173261B
CN103173261B CN201110439924.8A CN201110439924A CN103173261B CN 103173261 B CN103173261 B CN 103173261B CN 201110439924 A CN201110439924 A CN 201110439924A CN 103173261 B CN103173261 B CN 103173261B
Authority
CN
China
Prior art keywords
ionic liquid
preparation
trifluoromethanesulfonimide
hydroxyethyl
liquid lubricant
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.)
Active
Application number
CN201110439924.8A
Other languages
Chinese (zh)
Other versions
CN103173261A (en
Inventor
夏延秋
宋言新
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 CN201110439924.8A priority Critical patent/CN103173261B/en
Publication of CN103173261A publication Critical patent/CN103173261A/en
Application granted granted Critical
Publication of CN103173261B publication Critical patent/CN103173261B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Lubricants (AREA)

Abstract

The invention discloses hydroxyl imidazole functionalized ionic liquid lubricant and a preparation method thereof. The chemical name of the ionic liquid is 1-(2-ethoxyl)-3-decyl dual imidazole trifluoromethane sulfimide and the molecular formula of the ionic liquid is C17H29N3S2O4F6. The ionic liquid lubricant has the advantages of low melting point, incombustibility, low volatility, high heat stability, very low friction coefficient, extreme pressure abrasion resistance, simpleness in preparation process and method and high conversion ratio, can be widely applied to various friction pairs and specific working conditions, is also suitable for large-scale preparation and has broad practical application prospect.

Description

Hydroxy imidazole functionalized ion liquid lubricant and preparation method thereof
Technical field
The present invention relates to a kind of hydroxy imidazole functionalized ion liquid lubricant and preparation method thereof.
Background technology
Along with the development of high-tech area, traditional lubricant be difficult to meet under severe conditions (high vacuum, severe radiation, high/low temperature, at a high speed, high loading, microgravity) lubrication and protection, the over-all properties of people to lubricant is had higher requirement, the liquid lubricant with low-vapor pressure, high thermal stability and low-temperature fluidity with himself plurality of advantages be aerospace always, war industry, electronics, the computer industry target of pursuing, especially in the lubrication of space mechanism.Therefore, the research of high performance lubricant will be one of tribological field problem demanding prompt solution.
From calendar year 2001, Lanzhou Inst. of Chemical Physics, Chinese Academy of Sciences takes the lead in have studied after ionic liquid is the multi-usage lubricant of a class excellent performance, and ionic liquid causes the attention of quite a lot of researchist as the research of lubricant.In recent years, due to " designability " of ionic liquid, on the positively charged ion that one or more functional group can be incorporated into ionic liquid or negatively charged ion, by ion liquid functionalization.At present, the research of most of functionalized ion liquid concentrates in cationic functionalization, as introduced hydroxyl (-OH), amido (-NH on the side chain of alkylimidazolium cation 2), cyano group (-CN), sulfydryl (-SH), urea groups (-NHCOONH-), carboxyl (-COOH), ester group (-COOR), sulfonic group (-SO 3h), Ethoxysilane-Si (EtO) 3, perfluoroalkyl (-(CH 2) x(CF 2) xcF 3) etc. functional group.Therefore there is the design of the new function ionic liquid of property, one of Disciplinary Frontiers that Synthesis and application becomes ionic liquid research.
Ionic liquid have nonflammable explosive, fusing point is low (can lower than-90 DEG C), volatility is low, good in oxidation resistance and thermostability high, these features and the performance desired by ideal lubricant very identical, and harsh space lubrication environment can be suitable for, be expected to become the special lubricant of high-performance, the tribological property of research ionic liquid, has very important significance to the exploitation of Novel lubricating material.
Summary of the invention
The object of the present invention is to provide good low melting point, non-combustible, volatility is low and thermostability have ion liquid lubricant of excellent extreme pressure and antiwear behavior and preparation method thereof, ionic liquid is applied to various friction pair and specific working condition.
A kind of hydroxy imidazole functionalized ion liquid lubricant, is characterized in that ionic liquid chemical name is that the two trifluoromethanesulfonimide salt of 1-(2-hydroxyethyl)-3-decyl imidazoles (is abbreviated as [C 2oHDim] [NTf 2]), molecular formula is C 17h 29n 3s 2o 4f 6
Structural formula is:
Hydroxy imidazole functionalized ion liquid is colorless and odorless transparent liquid, its physico-chemical parameter: at 40 and 100 DEG C, viscosity index is respectively 324.9,25.1mm 2/ s, viscosity index is 99, and heat decomposition temperature is 358.4 DEG C.
Ionic liquid of the present invention introduces hydroxyl (-OH) functional group on the side chain of alkylimidazolium cation, by ion liquid functionalization, the polar organic compound that prepared ionic liquid is made up of anions and canons, is easily dissolved in common polar material.
The preparation feedback equation of ionic liquid of the present invention is as follows:
(1)
(2)
In the preparation method of ion liquid lubricant of the present invention, main raw material has 1-bromodecane, ethylene chlorhydrin and two trifluoromethanesulfonimide lithium salts.
A kind of hydroxy imidazole functionalized ion liquid lubricant, ionic liquid chemical name is that the two trifluoromethanesulfonimide salt of 1-(2-hydroxyethyl)-3-decyl imidazoles (is abbreviated as [C 2oHDim] [NTf 2]), molecular formula is C 17h 29n 3s 2o 4f 6
Structural formula is:
Its preparation method, it is characterized in that the method successively step be:
A constantly stirs down, and ethylene chlorhydrin is added in the reaction vessel of 1-decyl imidazoles, nitrogen protection, is slowly warming up to 78-82 DEG C, and stirring reaction is chilled to room temperature, adds after distilled water dissolves and washs impurity by ethyl acetate;
B is again joining in the above-mentioned washed aqueous solution containing two trifluoromethanesulfonimide lithium salts, after completion of the reaction, be extracted with ethyl acetate, distilled water wash, after anhydrous magnesium sulfate drying, remove solvent under reduced pressure and obtain the two trifluoromethanesulfonimide ionic liquid of 1-(2-hydroxyethyl)-3-decyl imidazoles.
The present invention has following characteristics: (1) yield high (> 90%); (2) reaction conditions is gentle; (3) there is higher supporting capacity; (4) lower frictional coefficient and less wear volume, have excellent antifriction and abrasion resistance; (5) the multi-usage lubricant of excellent performance.
Ionic liquid has good low melting point, non-combustible, volatility is low and thermostability is high and have very low frictional coefficient and longer extreme pressure and antiwear behavior, preparation process and method simple, transformation efficiency is high, various friction pair and specific working condition can be widely used in, also be applicable to extensive preparation, there is actual application prospect widely.
Accompanying drawing explanation
Fig. 1 is the frictional coefficient under constant pressure frequency conversion.
Fig. 2 is the wear volume under constant pressure frequency conversion.Wherein Friction coefficient represents frictional coefficient, and Wearvolume represents wear volume, and Frenquency represents frequency.
Two trifluoromethanesulfonimide lithium salts ([the EMim] [NTf of A:1-ethyl-3-methylimidazole 2]
Two trifluoromethanesulfonimide the lithium salts ([C of B:1-(2-hydroxyethyl)-3-decyl imidazoles 2oHDim] [NTf 2])
Fig. 1 and Fig. 2 is design temperature 25 DEG C, amplitude 1mm, frequency 10 ~ 50Hz, the micro-vibration friction abrasion testing machine of SRV-IV that load is produced from 100N in German Optimol grease company and the data that non-contact optical contourgraph obtains.
Fig. 3 is the frictional coefficient under constant voltage constant frequency.
Fig. 4 is the wear volume under constant pressure frequency conversion.Fig. 3 and Fig. 4 is design temperature 25 DEG C, the data that the micro-vibration friction abrasion testing machine of SRV-IV that amplitude 1mm, frequency 20Hz, load 100N produce in German Optimol grease company and non-contact optical contourgraph obtain.
Embodiment
Embodiment 1
Two trifluoromethanesulfonimide lithium salts the ionic liquid ([C of 1-(2-hydroxyethyl)-3-decyl imidazoles 2oHDim] [NTf 2]) synthesis
Under continuous stirring and nitrogen protection; ethylene chlorhydrin and 1-decyl imidazoles are joined in the reaction vessel containing dehydrated alcohol; heating; stir, be chilled to room temperature, after adding distilled water dissolving; wash by ethyl acetate; steam again and desolventize, use acetone frozen recrystallization, obtain chlorination 1-(2-hydroxyethyl)-3-alkyl imidazole ionic liquid (productive rate: 82%).
Chlorination 1-(2-hydroxyethyl)-3-decyl imidazole salts is dissolved in aqueous ethanolic solution, add two trifluoromethanesulfonimide lithium salts, after stirred at ambient temperature, successively evaporate to dryness ethanol, be extracted with ethyl acetate, water washing ethyl acetate mixtures, anhydrous magnesium sulfate drying, last solvent evaporated obtains the two trifluoromethanesulfonimide lithium salts ionic liquid (productive rate: about 92%) of 1-(2-hydroxyethyl)-3-decyl imidazoles.
Win power with U.S. Brookfield respectively and fly DV-III programmable control standard rheometer (aBrookfield DV-III Ultra Programmable Rheometer) and resistance to synchronous solving of speeding (the aSTA 449C of Germany -Simultaneous TG-DTA) physical properties such as viscosity, heat decomposition temperature of new synthesis ionic liquid is studied.Result is as follows:
Table 1: the physicals of the new ionic liquid of this synthesis
The micro-vibration friction abrasion testing machine of SRV-IV (OptimolSRV-IV oscillating reciprocating friction and wear tester) adopting German Optimol grease company to produce and non-contact optical contourgraph (MicroXAM 3D non-contact surface mapping profiler) have rated two trifluoromethanesulfonimide lithium salts ([the EMim] [NTf of conventional contrast ionic liquid 1-ethyl-3-methylimidazole 2], A) and two trifluoromethanesulfonimide the lithium salts ([C of synthesized new ionic liquid 1-(2-hydroxyethyl)-3-decyl imidazoles 2oHDim] [NTf 2], B) as the friction and wear behavior of steel/steel-steel pair.Experimentally try as AISI 52100 steel ball, lower sample is AISI 52100 bloom, selects two kinds of friction conditions under room temperature:
(1) load 100N, frequency 10-50Hz, amplitude 1mm, experimental period 25min;
(2) load 100N, frequency 20Hz, amplitude 1mm, experimental period 25min.
As seen from the figure:
On two different occasions, [C 2oHDim] [NTf 2] have excellent frictional behaviour, namely frictional coefficient (as Fig. 1 and 3) and wear volume (as Fig. 2 and 4) more stable, frictional coefficient is greatly between 0.09 ~ 0.10, and wear volume is respectively 1.9 × 10 5um 3with 2.6 × 10 5um 3; And [EMim] [NTf 2] frictional coefficient (as Fig. 1 and 3) and wear volume (as Fig. 2 and 4) very unstable, its frictional coefficient is greatly between 0.11 ~ 0.13, and wear volume is respectively 2.93 × 10 5um 3with 3.45 × 10 5um 3.Clearly, [C 2oHDim] [NTf 2] friction and wear behavior to be much better than [EMim] [NTf 2].

Claims (2)

1. a hydroxy imidazole functionalized ion liquid lubricant, it is characterized in that ionic liquid chemical name is the two trifluoromethanesulfonimide salt of 1-(2-hydroxyethyl)-3-decyl imidazoles, structural formula is:
2. a hydroxy imidazole functionalized ion liquid lubricant, ionic liquid chemical name is the two trifluoromethanesulfonimide salt of 1-(2-hydroxyethyl)-3-decyl imidazoles, and structural formula is:
Its preparation method, it is characterized in that the method successively step be:
A constantly stirs down, ethylene chlorhydrin is added in the reaction vessel of 1-decyl imidazoles, nitrogen protection, is slowly warming up to 78.82 DEG C, stirring reaction, is chilled to room temperature, adds after distilled water dissolves and washs impurity by ethyl acetate;
B is again joining in the above-mentioned washed aqueous solution containing two trifluoromethanesulfonimide lithium salts, after completion of the reaction, be extracted with ethyl acetate, distilled water wash, after anhydrous magnesium sulfate drying, remove solvent under reduced pressure and obtain the two trifluoromethanesulfonimide ionic liquid of 1-(2-hydroxyethyl)-3-decyl imidazoles.
CN201110439924.8A 2011-12-23 2011-12-23 Hydroxyl imidazole functionalized ionic liquid lubricant and preparation method thereof Active CN103173261B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201110439924.8A CN103173261B (en) 2011-12-23 2011-12-23 Hydroxyl imidazole functionalized ionic liquid lubricant and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201110439924.8A CN103173261B (en) 2011-12-23 2011-12-23 Hydroxyl imidazole functionalized ionic liquid lubricant and preparation method thereof

Publications (2)

Publication Number Publication Date
CN103173261A CN103173261A (en) 2013-06-26
CN103173261B true CN103173261B (en) 2015-02-25

Family

ID=48633463

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201110439924.8A Active CN103173261B (en) 2011-12-23 2011-12-23 Hydroxyl imidazole functionalized ionic liquid lubricant and preparation method thereof

Country Status (1)

Country Link
CN (1) CN103173261B (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103343030B (en) * 2013-07-09 2015-06-10 陈立功 Functionalized ionic liquid lubricating agent
CN109294704B (en) * 2018-10-16 2021-10-26 惠华科技有限公司 Antiwear automatic gearbox oil and preparation process thereof
CN109233937B (en) * 2018-10-16 2021-06-15 惠华科技有限公司 Graphene oxide lubricating additive and application thereof in antiwear automatic transmission oil
CN111116480A (en) * 2018-11-01 2020-05-08 中国科学院宁波材料技术与工程研究所 Bilateral asymmetric alkyl imidazole ionic liquid, and preparation method and application thereof
CN111218323B (en) * 2020-02-24 2022-06-14 辽宁大学 Environment-friendly lubricating oil and preparation method thereof
CN113046160B (en) * 2021-03-25 2022-04-22 清华大学 Polyhydroxy functionalized ionic liquid lubricant and preparation method thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007077058A1 (en) * 2006-01-03 2007-07-12 Degussa Ag Resins containing ionic liquids
CN101643682A (en) * 2008-08-08 2010-02-10 中国科学院兰州化学物理研究所 Ionic liquid high-temperature lubricant

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007077058A1 (en) * 2006-01-03 2007-07-12 Degussa Ag Resins containing ionic liquids
CN101643682A (en) * 2008-08-08 2010-02-10 中国科学院兰州化学物理研究所 Ionic liquid high-temperature lubricant

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation;Jonathan G.Huddleston等;《Green Chemistry》;20010705;第3卷;第156-164页 *
Preparation and Characterization of New Room Temperature Ionic Liquids;L.C.Branco等;《Chem. Eur. J.》;20021231;第8卷(第16期);第3671-3677页 *
两种离子液体的摩擦学行为研究;张晟卯等;《润滑与密封》;20060930(第9期);第40-43页 *

Also Published As

Publication number Publication date
CN103173261A (en) 2013-06-26

Similar Documents

Publication Publication Date Title
CN103173261B (en) Hydroxyl imidazole functionalized ionic liquid lubricant and preparation method thereof
Ge et al. Superlubricity and antiwear properties of in situ-formed ionic liquids at ceramic interfaces induced by tribochemical reactions
Zhou et al. Structure and properties of new ionic liquids based on alkyl‐and alkenyltrifluoroborates
Zhou et al. Cyclic quaternary ammonium ionic liquids with perfluoroalkyltrifluoroborates: synthesis, characterization, and properties
Dean et al. Structural analysis of low melting organic salts: perspectives on ionic liquids
Bonhote et al. Hydrophobic, highly conductive ambient-temperature molten salts
Monteiro et al. Ether-bond-containing ionic liquids and the relevance of the ether bond position to transport properties
Sharma et al. An overview of deep eutectic solvents: Alternative for organic electrolytes, aqueous systems & ionic liquids for electrochemical energy storage
Toledo Hijo et al. Phase behavior and physical properties of new biobased ionic liquid crystals
Martins et al. Influence of the water content on the structure and physicochemical properties of an ionic liquid and its Li+ mixture
BRPI0810874B1 (en) IONIC LIQUID, PROCESS FOR PREPARING IONIC LIQUID, AND, USING IONIC LIQUIDS.
Song et al. Lithium-based ionic liquids: in situ-formed lubricant additive only by blending
CN102776053A (en) Composite extreme pressure anti-wear agent and total-synthesis anti-wear hydraulic oil containing same
Tong et al. Hybrid gel electrolytes derived from keggin-type polyoxometalates and imidazolium-based ionic liquid with enhanced electrochemical stability and fast ionic conductivity
Shaplov et al. New family of highly conductive and low viscous ionic liquids with asymmetric 2, 2, 2-trifluoromethylsulfonyl-N-cyanoamide anion
CN102746279A (en) Benzotriazole group-containing ionic liquid and its preparation method and use
Zhou et al. A new class of hydrophobic ionic liquids: Trialkyl (2-methoxyethyl) ammonium perfluoroethyltrifluoroborate
Antunes et al. Deep eutectic solvents (DES) based on sulfur as alternative lubricants for silicon surfaces
JP2016511749A (en) Low symmetry molecules and phosphonium salts, preparation methods and devices formed therefrom
CN107532100A (en) Include the lubricant of the ionic liquid containing silicon
Zhou et al. Low-viscous, low-melting, hydrophobic ionic liquids: 1-alkyl-3-methylimidazolium trifluoromethyltrifluoroborate
CN106674063A (en) Amphiphilic small organic molecule gelator, and preparation method and application thereof
CN107162918A (en) 2 chlorinations, the synthetic method of 3 poly- hydroxypropyl isopropylamine quaternary surfactants
Al Kaisy et al. Novel halogen free hydrophobic trioctylammonium-based protic ionic liquids with carboxylate anions: Synthesis, characterization, and thermophysical properties
Yang et al. Asymmetric sulfonium-based molten salts with TFSI− or PF6− anion as novel electrolytes

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant