CN115772194B - Cation functionalized ionic liquid lubricating additive, preparation method and application thereof - Google Patents
Cation functionalized ionic liquid lubricating additive, preparation method and application thereof Download PDFInfo
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- CN115772194B CN115772194B CN202211389316.5A CN202211389316A CN115772194B CN 115772194 B CN115772194 B CN 115772194B CN 202211389316 A CN202211389316 A CN 202211389316A CN 115772194 B CN115772194 B CN 115772194B
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- ionic liquid
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- lubricating additive
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- intermediate product
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 33
- 239000000654 additive Substances 0.000 title claims abstract description 32
- 230000000996 additive effect Effects 0.000 title claims abstract description 27
- 230000001050 lubricating effect Effects 0.000 title claims abstract description 27
- 150000001768 cations Chemical class 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title abstract description 16
- 150000002148 esters Chemical class 0.000 claims abstract description 15
- 239000013067 intermediate product Substances 0.000 claims abstract description 12
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 claims abstract description 5
- SEGLCEQVOFDUPX-UHFFFAOYSA-N di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229940017219 methyl propionate Drugs 0.000 claims abstract description 4
- 125000002091 cationic group Chemical group 0.000 claims description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003879 lubricant additive Substances 0.000 claims description 2
- 125000005591 trimellitate group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000005588 protonation Effects 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 abstract description 4
- 239000003963 antioxidant agent Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 25
- 238000001228 spectrum Methods 0.000 description 8
- 239000002199 base oil Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 229910000831 Steel Inorganic materials 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 3
- 230000003064 anti-oxidating effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- -1 trimellitic acid ester Chemical class 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 101100218963 Botryococcus braunii TMT-3 gene Proteins 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N anhydrous trimellitic acid Natural products OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000005590 trimellitic acid group Chemical class 0.000 description 1
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- Lubricants (AREA)
Abstract
The invention provides a cation functionalized ionic liquid lubricating additive, a preparation method and application thereof, and the structural formula is as follows:the preparation method of the ionic liquid lubricating additive comprises the following steps: n-butyl diethanolamine and beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) methyl propionate with the same molar ratio of 1:2 are weighed and added into a single-neck flask, and are stirred and reacted for 12 hours at 200 ℃ under reduced pressure, wherein the pressure is-0.090 MPa, and an intermediate product is obtained. And (3) reacting the intermediate product with di (2-ethylhexyl) phosphate in a molar ratio of 1:1 at a temperature of 100 ℃ for 4 hours to obtain the cation functionalized ionic liquid. The ionic liquid lubricating additive has excellent antioxidant, antiwear and antifriction properties in the synthesis of ester.
Description
Technical Field
The invention relates to a cation functionalized ionic liquid lubricating additive, a preparation method and application thereof, and belongs to the technical field of lubrication.
Background
Since 2001 (Ye C, liu W, chen Y, et al Room-temperature ionic liquids: a novel versatile lubricant [ J ]. Chemical Communications,2001 (21): 2244-2245) reported that ionic liquid lubricating additives have been gradually developed as an important branch of lubricating additives, ionic liquids have various excellent characteristics such as low volatility, thermal stability, excellent antiwear properties and the like as lubricating additives, making them research hot spots for lubricating additives, but the disadvantages of high cost of ionic liquids, complex preparation process, poor solubility in base oils, and strong corrosiveness of halogen-containing ionic liquids have limited the wide use of ionic liquids as lubricating additives.
The synthetic ester is a fifth base oil, has the characteristics of excellent high-low temperature performance, high viscosity index, high flash point, high ignition point, easy biodegradation and the like, and is commonly used for severe working conditions where base oils such as mineral oil, PAO and the like are difficult to be suitable. High temperature chain oils are a typical application for synthetic esters, such as trimellitic acid esters, dipentaerythritol esters are the primary base oils for high temperature chain oils. The high temperature chain oil is easy to oxidize due to high working condition temperature (generally higher than 180 ℃), a certain antioxidant is needed to be added to improve oxidation stability, and meanwhile, an antiwear additive is needed to be added into the high temperature chain oil in order to maintain good lubricity in chain transmission, and the high temperature chain oil is required to have good oxidation resistance and lubricating property.
Disclosure of Invention
The cation functionalized ionic liquid lubricating additive prepared by the invention introduces an antioxidant functional group into cations, so that the anti-oxidation and anti-wear functions are realized, the preparation process is simple, the preparation cost is low, and the additive is used as a bifunctional additive in synthetic ester, especially used as a lubricating additive of high-temperature chain oil, and has excellent anti-oxidation and anti-wear properties.
The invention aims to provide a cation functionalized ionic liquid lubricating additive, a preparation method and application thereof, and solves the problems of complex preparation process, high preparation cost and single performance of ionic liquid in the prior art.
The invention adopts the following technical scheme:
a cationically functionalized ionic liquid lubricating additive having the structural formula of formula (1):
the preparation method of the cation functionalized ionic liquid lubricating additive provided by the invention comprises the following steps of:
n-butyl diethanolamine and beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) methyl propionate with the molar ratio of 1:2 are weighed and added into a single-neck flask, and are stirred and reacted for 12 hours at 200 ℃ under reduced pressure, wherein the pressure is minus 0.090MPa, and an intermediate product is obtained, and the intermediate product has the structural formula of formula (2).
And (3) reacting the intermediate product with di (2-ethylhexyl) phosphate in a molar ratio of 1:1 at a temperature of 100 ℃ for 4 hours to obtain the cation functionalized ionic liquid.
The invention also provides application of the cationic functional ionic liquid lubricating additive, wherein the ionic liquid lubricating additive is used in synthetic ester, and the dosage of the ionic liquid lubricating additive in the synthetic ester is 0.5-2 wt% based on the mass of the synthetic ester. For example, the ionic liquid lubricant additive may be used in an amount of 0.5wt%, 1.0wt%, 1.5wt% or 2wt% in the synthetic ester based on the mass of the synthetic ester.
The synthetic ester is one of trimellitic acid ester and dipentaerythritol ester.
The invention has the technical characteristics and beneficial effects that:
the cationic functional ionic liquid lubricating additive has the dual functions of antioxidation and antiwear, and has the advantages of simple preparation method, high product yield, low preparation cost and potential popularization and application value.
Drawings
FIGS. 1 (a) and (b) are respectively the nuclear magnetic resonance hydrogen spectrum and the carbon spectrum of the intermediate product;
fig. 2 (a) and (b) are respectively nuclear magnetic resonance hydrogen spectrum and carbon spectrum of the cation functionalized ionic liquid.
Detailed Description
The invention is further illustrated and described below in connection with specific examples.
Example 1
8.06g (0.05 mol) of N-butyl diethanolamine and 29.24g (0.1 mol) of beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) methyl propionate are weighed and added into a 100ml single-neck flask, and stirred and reacted for 12 hours at 200 ℃, the pressure is kept at-0.090 MPa, and a deep yellow viscous transparent liquid of an intermediate product is obtained, the nuclear magnetic characterization is shown in the attached figure 1, and the hydrogen spectrum (a) and the carbon spectrum (b) of the intermediate product; the intermediate obtained has the structural formula (2):
8.43g (0.02 mol) of the intermediate product and 6.44g (0.02 mol) of di (2-ethylhexyl) phosphate are weighed and added into a 25ml single-neck flask, and the mixture is stirred and reacted for 4 hours at 100 ℃ to obtain brown viscous liquid, namely cation functionalized ionic liquid, the nuclear magnetic characterization of which is shown in figure 2, and a hydrogen spectrum (a) and a carbon spectrum (b) of the cation functionalized ionic liquid.
The prepared cation functionalized ionic liquid has the structural formula (1):
the present invention will be further described below by way of test examples. The composition of the test sample is shown in Table 2, in which the base oil trimellitate (TMT-3, charles New Material Co., ltd.) has a viscosity of 74.4mm at 40 ℃ 2 Viscosity at 100℃of 9.6 mm/s 2 S, flash point 276 ℃, pour point-27 ℃; base oil dipentaerythritol ester (Synergy New Material technology Co., ltd. Hadoop) has a viscosity of 364.5mm at 40℃of 2 Viscosity at 100℃of 24.8mm 2 S, flash point is 286 ℃, pour point is-18 ℃.
Table 2 composition of test examples and comparative examples
Tribological performance test
The test examples and comparative examples were subjected to tribological performance testing, test methods: the test equipment is an SRV-V fretting friction wear tester of Optimol grease company, germany, the test condition is that the load is 100N, the temperature is 100 ℃, the frequency is 50Hz, the stroke is 1mm, and the time is 30min. The steel ball used in the test is AISI52100 bearing steel with the diameter of 10mm, and the steel block used in the lower sample is AISI52100 bearing steel with the diameter of 24mm and the height of 7.9 plus or minus 0.1 mm. The abrasion diameter of the steel ball of the upper sample was measured by using a microscope to characterize the abrasion resistance, and the test results are shown in Table 3.
Test of antioxidant Properties
The testing method comprises the following steps: the test equipment is a Pressurized Differential Scanning Calorimeter (PDSC), and the test conditions are in the temperature range: the temperature rise rate is 10 ℃/min at 40-350 ℃, and the sample dosage is 3.00mg plus or minus 0.05mg. The test results are shown in Table 3.
Table 3 test examples 1 to 6, comparative example 1, and comparative example 2, abrasion resistance and oxidation resistance test results
| Test sample | Steel ball mill spot diameter (mm) | Initial oxidation temperature (. Degree. C.) |
| Test example 1 | 0.380 | 217.4 |
| Test example 2 | 0.348 | 227.9 |
| Test example 3 | 0.377 | 240.9 |
| Test example 4 | 0.630 | 228.5 |
| Test example 5 | 0.592 | 234.6 |
| Test example 6 | 0.385 | 250.7 |
| Comparative example 1 | 0.527 | 209.1 |
| ComparisonExample 2 | 0.773 | 214.9 |
As can be seen from Table 3, the sizes of the polishing spot diameters of test examples 1 to 3 were decreased by 27.9%, 34.0% and 28.5% in order, and the initial oxidation temperatures were increased by 7.7 ℃, 18.8 ℃ and 31.8 ℃ in order, as compared with those of comparative example 1; the sizes of the abrasive spots in test examples 4 to 6 are reduced by 18.5%, 23.4% and 50.2% in sequence compared with those in comparative example 2, and the initial oxidation temperature is increased by 13.6 ℃ and 19.7 ℃ and 35.8 ℃ in sequence, so that the anti-wear performance and the oxidation resistance of the synthetic ester base oil can be obviously improved by adding the prepared cation functionalized ionic liquid into the synthetic ester.
The invention has the beneficial effects that: the preparation method is simple, the product yield is high, the preparation cost is low, and the ionic liquid lubricating additive has potential popularization and application values.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, alternatives, and improvements that fall within the spirit and scope of the invention.
Claims (7)
1. A cationically functionalized ionic liquid lubricant additive characterized in that the additive has the structural formula of formula (1):
2. a method of preparing a lubricity additive as claimed in claim 1, characterised in that the method comprises: n-butyl diethanolamine and beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) methyl propionate react to obtain an intermediate product, and the intermediate product reacts with di (2-ethylhexyl) phosphate in a protonation mode to obtain the cation functionalized ionic liquid lubricating additive.
3. The method of preparing a lubricating additive according to claim 2, wherein the intermediate obtained has the structural formula of formula (2):
4. the method for preparing the lubricating additive according to claim 2, wherein the molar ratio of the N-butyldiethanolamine to the methyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate is 1:2, the reaction temperature is 200 ℃, the reaction time is 12 hours, and the pressure is-0.090 MPa.
5. The method for preparing the lubricating additive according to claim 2, wherein the intermediate product is reacted with di (2-ethylhexyl) phosphate in a molar ratio of 1:1 at a temperature of 100 ℃ for 4 hours to obtain the cationic functional ionic liquid.
6. Use of a lubricating additive according to claim 1, characterised in that the additive is used in a synthetic ester, the additive being added in an amount of 0.5 to 2wt%, based on the mass of the synthetic ester.
7. The use according to claim 6, wherein the synthetic ester is trimellitate or dipentaerythritol.
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| CN115772194B true CN115772194B (en) | 2024-01-19 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1391479A (en) * | 1963-04-29 | 1965-03-05 | Geigy Ag J R | New esters derived from alkylhydroxy-benzenes and their applications, in particular for the stabilization of organic materials, for example polyolefins and elastomeric materials |
| CN113403121A (en) * | 2021-04-26 | 2021-09-17 | 中国科学院兰州化学物理研究所 | Ionic liquid antirust and antiwear additive for polyether lubricating oil |
| CN114230605A (en) * | 2021-12-21 | 2022-03-25 | 中科润美（青岛）材料科技有限公司 | Polyisobutylene-based choline phosphate ionic liquid, preparation method and application thereof, and base oil composition |
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- 2022-11-08 CN CN202211389316.5A patent/CN115772194B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1391479A (en) * | 1963-04-29 | 1965-03-05 | Geigy Ag J R | New esters derived from alkylhydroxy-benzenes and their applications, in particular for the stabilization of organic materials, for example polyolefins and elastomeric materials |
| CN113403121A (en) * | 2021-04-26 | 2021-09-17 | 中国科学院兰州化学物理研究所 | Ionic liquid antirust and antiwear additive for polyether lubricating oil |
| CN114230605A (en) * | 2021-12-21 | 2022-03-25 | 中科润美（青岛）材料科技有限公司 | Polyisobutylene-based choline phosphate ionic liquid, preparation method and application thereof, and base oil composition |
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