CN103173261B - Hydroxyl imidazole functionalized ionic liquid lubricant and preparation method thereof - Google Patents
Hydroxyl imidazole functionalized ionic liquid lubricant and preparation method thereof Download PDFInfo
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- 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
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- trifluoromethanesulfonimide
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- NHHWJSXMTZIPES-UHFFFAOYSA-N O=S(C(F)(F)F)([N-]S(C(F)(F)F)(=O)=O)=O Chemical compound O=S(C(F)(F)F)([N-]S(C(F)(F)F)(=O)=O)=O NHHWJSXMTZIPES-UHFFFAOYSA-N 0.000 description 1
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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
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.
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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)
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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 |
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Patent Citations (2)
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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)
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 * |
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