CN102746279A - Benzotriazole group-containing ionic liquid and its preparation method and use - Google Patents
Benzotriazole group-containing ionic liquid and its preparation method and use Download PDFInfo
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- CN102746279A CN102746279A CN2011100980754A CN201110098075A CN102746279A CN 102746279 A CN102746279 A CN 102746279A CN 2011100980754 A CN2011100980754 A CN 2011100980754A CN 201110098075 A CN201110098075 A CN 201110098075A CN 102746279 A CN102746279 A CN 102746279A
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- ionic liquid
- hexyl
- butyl
- benzotriazole
- group
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Abstract
The invention discloses a benzotriazole group-containing ionic liquid and its preparation method and use. The benzotriazole group-containing ionic liquid is characterized in that cations are imidazolium cations; anions are hexafluorophosphate radical, tetrafluoroborate radical or bis(trifluoromethylsulfonyl)imide anions; and an imidazole ring-substituted end group contains a benzotriazole group. The benzotriazole group-containing ionic liquid can be used as a lubricant additive or a lubricating grease additive.
Description
Technical field
The present invention relates to a kind of anticorrosive, anti-oxidant ionic liquid and preparation and purposes that contains benzotriazole.
Background technology
Along with science and technology development; To lubricant particularly high performance lubricant increasingly high requirement has been proposed; Traditional lubricating oil has been difficult to satisfy the lubricated and requirement of shelter of some special machines under severe condition; Ionic liquid has many special performances, and like non-volatility, uninflammability, very high thermostability, low fusing point and good electrical conductivity etc., also the ideal lubricant is needed just for this.
Calendar year 2001, the applicant belongs to seminar and finds first that in the world ionic liquid is multi-usage lubricant (C.F.Ye, the W.M.Liu of one type of excellent performance; Y.X.Chen; L.G.Yu, Chem.Commun, 21 (2001) 2244-2245.); After this ion liquid lubicating material has been carried out deeply and systematic research, and caused domestic and international scientific research personnel's extensive attention.Ionic liquid can play good antifriction antiwear effect as high perofmrnace lubricating oils, and it has very high supporting capacity (W.M.Liu, C.F.Ye, Z.F.Zhang, L.G.Yu.Wear, 252 (2002) 394-400; H.Z.Wang, Q.M.Lu, C.F.Ye, W.M.Liu and Z.J.Cui.Wear 256 (2004) 44; Z.G.Mu, W.M.Liu, S.X.Zhang, and F.Zhou.Chemistry Letters 33 (2004) 524-525; X.Q.Liu, F.Zhou, Y.M.Liang, W.M.Liu, Wear 261 (2006) 1174-1179; M.H.Yao, M.J.Fan, Y.M; Liang, F.Zhou, Y.Q.Xia; Wear 268 (2010) 67-71), can improve anti-wear and wear-resistant performance (M.H.Yao, the Y.M.Liang of base oil greatly as base oil, fat additives; Y.Q.Xia, F.Zhou, ACS Appl.Mater.Interfaces 1 (2009) 467-471; M.R.Cai, Z.Zhao, Y.M.Liang, F.Zhou, W.M.Liu, Tribol.Lett.40 (2010) 215-224).Though ionic liquid has excellent tribological property, being prone to oxidation is bottlenecks of restriction ionic liquid industrial applications with these two problems of corrosion.The applicant has synthesized the substituted ionic liquid of sterically hindered phenol, and with its additive as polyoxyethylene glycol, has good anti-oxidant and antifriction antiwear ability (M.R.Cai; Y.M.Liang, M.H.Yao, Y.Q.Xia; F.Zhou, W.M.Liu, ACS Appl.Mater.Interf.2 (2010) 870-876).As everyone knows, benzotriazole and verivate thereof be industry go up metal passivator commonly used, anticorrosive and antioxidant addn (M.Braid, U.S.Patent 4519928,1985; J.Shim.U.S.Patent, 4511481,1985; R.M.Oneil, U.S.Patent, 5171463,1992).Document and patent investigation show also not about having anticorrosive simultaneously and the ion liquid synthetic and application report of oxidation-resistance.
Summary of the invention
The object of the present invention is to provide a kind of ionic liquid that contains benzotriazole.
Another object of the present invention provides a kind of preparation method of ionic liquid of benzotriazole.
Another purpose of the present invention is to provide a kind of ion liquid purposes that contains benzotriazole.
The present invention has synthesized the glyoxaline ion liquid that a kind of novel substituted alkyl contains benzotriazole first, and this ionic liquid is not seen bibliographical information so far.Ion liquid positively charged ion is a glyoxaline cation, and negatively charged ion is hexafluoro-phosphate radical, tetrafluoroborate or two (trifluoromethyl sulphonyl) amine negative ion, and the substituted end group of its imidazole ring contains the benzotriazole group.
Ionic liquid general formula of the present invention is:
R represent methylidene, butyl, hexyl or octyl group in the formula, X represents BF
4, N (CF
3SO
2)
2Or PF
6
The concrete ionic liquid of our synthetic does
[BTAMIM][BF
4]：R＝CH
3，X＝BF
4；[BTAMIM][BF
4]：R＝C
4H
9，X＝BF
4；
[BTAHIM][BF
4]：R＝C
6H
13，X＝BF
4；[BTAOIM][BF
4]：R＝C
8H
17，X＝BF
4；
[BTAMIM][NTf
2]：R＝CH
3，X＝N(CF
3SO
2)
2；[BTABIM][NTf
2]：R＝C
4H
9，X＝N(CF
3SO
2)
2；[BTAHIM][NTf
2]：R＝C
6H
13，X＝N(CF
3SO
2)
2；[BTAOIM][NTf
2]：R＝C
8H
17，X＝N(CF
3SO
2)
2；[BTAMIM][PF
6]：R＝CH
3，X＝PF
6；[BTABIM][PF
6]：R＝C
4H
9，X＝PF
6；[BTAHIM][PF
6]：R＝C
6H
13，X＝PF
6；[BTAOIM][PF
6]：R＝C
8H
17，X＝PF
6；
Ion liquid preparation feedback equation of the present invention is following:
Reaction equation 1:
Reaction equation 2:
Wherein R represent methylidene, butyl, hexyl and octyl group, X represents BF
4, N (CF
3SO
2)
2Or PF
6In the reaction equation 1, the preparation reference of 1-chloromethyl benzo triazole: J.H.Burckhalter, V.C.Stephens, Luther A.R.Hall.J.Am.Chem.Soc.74 (1952) 3868-3870.
Concrete preparation method is: get equimolar alkyl imidazole respectively and 1-chloromethyl benzo triazole is added in the reactor drum under nitrogen protection; In 60-70 ℃ of following complete reaction after-filtration; Obtain white or pale yellow powder, powder is used dissolved in distilled water, adds excessive hexafluorophosphate, a tetrafluoro borate or two (trifluoromethyl sulphonyl) amine salt under room temperature stirring reaction 16-24 hour; Obtain white powder behind the filtration drying, with silicagel column separate ionic liquid.
Alkyl represent methyl, butyl, hexyl or the octyl group mentioned among the preparation method.
Ionic liquid of the present invention has carried out structural characterization with HNMR and CNMR analysis means, confirms that its structure is indicated by above general formula.
Ion liquid thermogravimetric analysis result of the present invention shows that it has higher thermostability.
Ionic liquid of the present invention has anticorrosive and antioxidant property, can know through copper strip test, and ionic liquid of the present invention has anticorrosive preferably and antioxidant property as basic oil additives.
Ionic liquid of the present invention can be used as the additive of polyoxyethylene glycol and polyurea grease, adds the lubricant of ion liquid polyoxyethylene glycol as steel/steel-steel pair, has good anti-wear and wear-resistant performance and high supporting capacity.For polyurea grease, add ionic liquid and have more excellent tribological property than typical additives T204 afterwards.
Ionic liquid can be as oil dope or grease additive.
The experimental technique that adopts is following:
Adopt Optimol-SRV-IV type friction wear testing machine to estimate the tribological property of institute's synthetic ionic liquid under different loads and temperature condition. the friction pair contact form is that ball one is made an inventory and contacted; Selected frequency is 25Hz; Amplitude is 1mm, and test period is 30min, and temperature is room temperature and 150 ℃.On try and be diameter 10mmGCr15 (SAE52100) steel ball, following examination dish is a steel disk.
Embodiment
For a better understanding of the present invention, describe through embodiment.
Embodiment 1
1-benzotriazole methyl-3-Methylimidazole hexafluorophosphate is ion liquid synthetic
Add 4.105 gram N-Methylimidazoles in the 100ml there-necked flask and add the dissolving of 15ml Virahol, feed nitrogen protection slow the adding with 20ml Virahol dissolved 1-chloromethyl benzo triazole 8.358 grams, 60-70 ℃ was reacted down 15-20 hour.Revolve after the reaction and desolventize, white or pale yellow powder 11.42 grams, yield is 91%.In 250ml single port bottle, add 4.994 gram 1-benzotriazole methyl-3-Methylimidazole villaumites and add an amount of dissolved in distilled water; Dropwise drip 3.91 gram ammonium hexafluorophosphates with an amount of dissolved in distilled water; Solution becomes muddy adularescent solid rapidly and generates, and drips the back exchange 16-24 hour.Reacted after-filtration, drying gets 6.39 gram white powder solids, and silica gel column chromatography gets 5.94 gram white crystals, and yield is 93%.
1H-NMR(400MHz，CD
3COCD
3，ppm)：δ＝9.50(1H，s，N＝CH)，8.13(1H，s，CH-C)，8.10(1H，s，CH-C)，8.07(1H，s，N-CH)，7.80(1H，s，CH-N)，7.70(1H，s，CH＝CH)，7.50(1H，s，CH＝CH)，7.42(2H，s，CH
2)，4.11(3H，s，CH
3).
13C-NMR(100MHz，CD
3COCD
3，ppm)：146.7，138.2，133.2，129.6，129.6，125.6，123.0，120.6，110.5，59.0，36.9.
Embodiment 2
1-benzotriazole methyl-3-methyl imidazolium tetrafluoroborate is ion liquid synthetic
The method for making of 1-benzotriazole methyl-3-Methylimidazole villaumite is with embodiment one.In 250ml single port bottle, add 4.994 gram 1-benzotriazole methyl-3-Methylimidazole villaumites and add an amount of dissolved in distilled water; Dropwise drip 2.64 gram sodium tetrafluoroborates with an amount of dissolved in distilled water; Solution becomes muddy adularescent solid rapidly and generates, and drips the back exchange 16-24 hour.Reacted after-filtration, drying gets 5.4189 gram white powder solids, and silica gel column chromatography gets 5.21 gram white crystals, and yield is 96%.
1H-NMR(400MHz，CD
3COCD
3，ppm)：δ＝9.43(1H，s，N＝CH)，8.16(1H，s，CH-C)，8.09(1H，s，CH-C)，8.01(1H，s，N-CH)，7.76(1H，s，CH-N)，7.70(1H，s，CH＝CH)，7.50(1H，s，CH＝CH)，7.37(2H，s，CH
2)，4.10(3H，s，CH
3).
13C-NMR(100MHz，CD
3COCD
3，ppm)：146.5，138.1，133.1，129.4，129.4，125.3，122.8，120.3，110.6，59.6，36.7.
Embodiment 3
1-benzotriazole methyl-3-Methylimidazole two (trifluoromethyl sulphonyl) amine salt is ion liquid synthetic
The method for making of 1-benzotriazole methyl-3-Methylimidazole villaumite is with embodiment one.In 250ml single port bottle, add 4.994 gram 1-benzotriazole methyl-3-Methylimidazole villaumites and add an amount of dissolved in distilled water; Dropwise drip 6.89 gram two (trifluoromethyl sulphonyl) amine lithiums with an amount of dissolved in distilled water; Solution becomes muddy adularescent solid rapidly and generates, and drips the back exchange 16-24 hour.Reacted after-filtration, drying gets 9.19 gram white powder solids, and silica gel column chromatography gets 8.46 gram white crystals, and yield is 92%.
1H-NMR(400MHz，CD
3COCD
3，ppm)：δ＝9.50(1H，s，N＝CH)，8.12(1H，s，CH-C)，8.10(1H，s，CH-C)，8.07(1H，s，N-CH)，7.80(1H，s，CH-N)，7.70(1H，s，CH＝CH)，7.52(1H，s，CH＝CH)，7.42(2H，s，CH
2)，4.09(3H，s，CH
3).
13C-NMR(100MHz，CD
3COCD
3，ppm)：146.6，138.1，133.1，129.5，129.5，125.5，123.0，119.1，110.5，58.9，36.9.
Table 1: synthesize ion liquid heat decomposition temperature and fusing point
PEG measures by GB GB/T265-88, GB/T2541-81 (88) respectively with the kinematic viscosity of adding ion liquid PEG, viscosity index, density.
Table 2:PEG and the physicals of adding ion liquid PEG
(GB/T7326-87) can know through copper strip test, and ionic liquid of the present invention has anticorrosive preferably and antioxidant property as basic oil additives.
Table 3: copper strip test result
The little vibration friction abrasion testing machine of SRV-IV that adopts German optimol grease company to produce has been estimated the friction and wear behavior that adds ion liquid PEG and polyurea grease.
What table 4 was listed is frictional coefficient and the wear volume data of ionic liquid as the PEG additive, selects load for use: 100N, and frequency 25Hz, amplitude 1mm, experimental period 30min, 20 ℃ of temperature are experimentally tried to diameter is the 10mm steel ball, and following sample is a bloom.Experimental result shows with PEG to be compared, and the anti-wear and wear-resistant performance that adds ion liquid PEG all is greatly improved.
Table 4:PEG and the average friction coefficient and average wear volume of the ion liquid PEG of interpolation as steel/steel-steel pair lubricant
What table 5 was listed is frictional coefficient and the wear volume data of ionic liquid as the PEG additive, selects load for use: 100N, and frequency 25Hz, amplitude 1mm, experimental period 30min, 150 ℃ of temperature are experimentally tried to diameter is the 10mm steel ball, and following sample is a bloom.Experimental result shows adds after the ionic liquid, has excellent tribological property than blank oil.
Table 5:PEG and the average friction coefficient and average wear volume of the ion liquid PEG of interpolation as steel/steel-steel pair lubricant
What table 6 was listed is frictional coefficient and the wear volume data of ionic liquid as the polyurea grease additive, selects load for use: 300N, frequency 25Hz; Amplitude 1mm, experimental period 30min, 150 ℃ of temperature; Experimentally try to diameter is the 10mm steel ball, following sample is a bloom.Experimental result shows with blank fat to be compared with antiwear and friction-reducing additive T204 commonly used, adds ion liquid polyurea grease and has lower frictional coefficient and littler wear volume.
Table 6: polyurea grease and the average friction coefficient and average wear volume that add after the ionic liquid as steel/steel-steel pair lubricant
Claims (4)
1. one kind contains benzotriazole group ionic liquid, it is characterized in that the ionic liquid general formula is:
R represent methylidene, butyl, hexyl or octyl group in the formula, X represents BF
4, N (CF
3SO
2)
2Or PF
6
2. a general formula is:
Contain benzotriazole group preparation method of ionic liquid, R represent methylidene, butyl, hexyl or octyl group in the formula, X represents BF
4, N (CF
3SO
2)
2Or PF
6It is characterized in that this method is got equimolar alkyl imidazole respectively and 1-chloromethyl benzo triazole is added in the reactor drum under nitrogen protection,, obtain white or pale yellow powder in 60-70 ℃ of following complete reaction after-filtration; Powder is used dissolved in distilled water; Add excessive hexafluorophosphate, a tetrafluoro borate or two (trifluoromethyl sulphonyl) amine salt under room temperature stirring reaction 16-24 hour, obtain white powder behind the filtration drying, with silicagel column separate ionic liquid.
3. method as claimed in claim 2 is characterized in that alkyl represent methyl, butyl, hexyl or octyl group.
4. a general formula is:
Contain the ion liquid application of benzotriazole group, R represent methylidene, butyl, hexyl or octyl group in the formula, X represents BF
4, N (CF
3SO
2)
2Or PF
6, it is characterized in that ionic liquid is as oil dope or grease additive.
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103333728A (en) * | 2013-07-09 | 2013-10-02 | 陈立功 | Corrosion-resistant lubricant |
| CN103833652A (en) * | 2012-11-26 | 2014-06-04 | 海洋王照明科技股份有限公司 | Triazole ionic liquid, and preparation method and application thereof |
| CN104327054A (en) * | 2014-11-05 | 2015-02-04 | 华东交通大学 | Water-soluble benzotriazole imidazoline extreme-pressure anti-wear reagent and preparation method thereof |
| CN104877748A (en) * | 2014-02-27 | 2015-09-02 | 中国科学院兰州化学物理研究所 | Lubricating jelly composition and preparation method thereof |
| CN104250231B (en) * | 2014-09-18 | 2016-04-06 | 陕西煤业化工技术开发中心有限责任公司 | For the synthesis of the benzotriazole ionic liquid of toluencediamine base alkyl formate |
| CN109385635A (en) * | 2018-12-07 | 2019-02-26 | 华侨大学 | A kind of compounding ionic liquid corrosion inhibiter and preparation method thereof |
| CN110845430A (en) * | 2019-12-04 | 2020-02-28 | 中国科学院兰州化学物理研究所 | Benzotriazole functionalized quaternary ammonium salt and preparation method and application thereof |
| CN110862356A (en) * | 2019-12-04 | 2020-03-06 | 中国科学院兰州化学物理研究所 | Benzotriazole functionalized quaternary ammonium salt ionic liquid and preparation method and application thereof |
| CN111004669A (en) * | 2019-12-11 | 2020-04-14 | 中国科学院兰州化学物理研究所 | Ionic liquid lignin lubricating composition and preparation method and application thereof |
| CN112662450A (en) * | 2020-12-22 | 2021-04-16 | 邵敏 | High-wear-resistance lubricating oil and preparation method thereof |
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| CN103833652A (en) * | 2012-11-26 | 2014-06-04 | 海洋王照明科技股份有限公司 | Triazole ionic liquid, and preparation method and application thereof |
| CN103333728B (en) * | 2013-07-09 | 2015-06-10 | 陈立功 | Corrosion-resistant lubricant |
| CN103333728A (en) * | 2013-07-09 | 2013-10-02 | 陈立功 | Corrosion-resistant lubricant |
| CN104877748B (en) * | 2014-02-27 | 2017-10-17 | 中国科学院兰州化学物理研究所 | A kind of lubricationg jelly composition and preparation method thereof |
| CN104877748A (en) * | 2014-02-27 | 2015-09-02 | 中国科学院兰州化学物理研究所 | Lubricating jelly composition and preparation method thereof |
| CN104250231B (en) * | 2014-09-18 | 2016-04-06 | 陕西煤业化工技术开发中心有限责任公司 | For the synthesis of the benzotriazole ionic liquid of toluencediamine base alkyl formate |
| CN104327054A (en) * | 2014-11-05 | 2015-02-04 | 华东交通大学 | Water-soluble benzotriazole imidazoline extreme-pressure anti-wear reagent and preparation method thereof |
| CN104327054B (en) * | 2014-11-05 | 2019-06-25 | 华东交通大学 | Water-soluble benzotriazole imidazoline extreme pressure anti-wear additives and preparation method thereof |
| CN109385635A (en) * | 2018-12-07 | 2019-02-26 | 华侨大学 | A kind of compounding ionic liquid corrosion inhibiter and preparation method thereof |
| CN110845430A (en) * | 2019-12-04 | 2020-02-28 | 中国科学院兰州化学物理研究所 | Benzotriazole functionalized quaternary ammonium salt and preparation method and application thereof |
| CN110862356A (en) * | 2019-12-04 | 2020-03-06 | 中国科学院兰州化学物理研究所 | Benzotriazole functionalized quaternary ammonium salt ionic liquid and preparation method and application thereof |
| CN110845430B (en) * | 2019-12-04 | 2021-03-09 | 中国科学院兰州化学物理研究所 | Benzotriazole functionalized quaternary ammonium salt and preparation method and application thereof |
| CN111004669A (en) * | 2019-12-11 | 2020-04-14 | 中国科学院兰州化学物理研究所 | Ionic liquid lignin lubricating composition and preparation method and application thereof |
| CN112662450A (en) * | 2020-12-22 | 2021-04-16 | 邵敏 | High-wear-resistance lubricating oil and preparation method thereof |
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