CN116143829B - High extreme pressure proton type ionic liquid, preparation method and application thereof as oil-based additive - Google Patents
High extreme pressure proton type ionic liquid, preparation method and application thereof as oil-based additive Download PDFInfo
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- CN116143829B CN116143829B CN202211665272.4A CN202211665272A CN116143829B CN 116143829 B CN116143829 B CN 116143829B CN 202211665272 A CN202211665272 A CN 202211665272A CN 116143829 B CN116143829 B CN 116143829B
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 52
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000000654 additive Substances 0.000 title claims abstract description 10
- 230000000996 additive effect Effects 0.000 title abstract description 9
- 239000002199 base oil Substances 0.000 claims abstract description 26
- 239000003921 oil Substances 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims description 18
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 10
- FMNZBNCPTJEVDS-KVVVOXFISA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;(z)-octadec-9-enoic acid Chemical compound CCC(CO)(CO)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O FMNZBNCPTJEVDS-KVVVOXFISA-N 0.000 claims description 7
- 229940049964 oleate Drugs 0.000 claims description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 235000019198 oils Nutrition 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- 239000010775 animal oil Substances 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 29
- -1 alkylamine cation Chemical class 0.000 description 28
- 230000000052 comparative effect Effects 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 229910000831 Steel Inorganic materials 0.000 description 12
- 239000010959 steel Substances 0.000 description 12
- 230000001050 lubricating effect Effects 0.000 description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Natural products CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000005461 lubrication Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- SEGLCEQVOFDUPX-UHFFFAOYSA-N di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002892 organic cations Chemical class 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000010687 lubricating oil 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
- 150000002891 organic anions Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
- C07C211/08—Monoamines containing alkyl groups having a different number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/11—Esters of phosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
-
- 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
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/08—Ammonium or amine salts
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/401—Fatty vegetable or animal oils 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
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/043—Ammonium or amine salts thereof
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a high extreme pressure proton type ionic liquid, a preparation method and application thereof as an oil-based additive. The proton type ionic liquid provided by the invention has excellent antifriction and antiwear properties, the preparation method is simple, the cost is low, the component types are few, the solubility of the base oil is good, and the comprehensive performance of the base oil can be greatly improved by taking the proton type ionic liquid as the base oil additive.
Description
Technical Field
The invention relates to the technical field of lubricants, in particular to a high extreme pressure proton type ionic liquid, a preparation method and application thereof as an oil-based additive
Background
Ionic liquid (or ionic liquid) refers to a liquid that is composed entirely of ions. The ionic liquid has the advantages of low vapor pressure, large heat capacity, high chemical stability, strong solubility, low viscosity, large density and the like, and has the basic condition of becoming an excellent lubricant, so that the ionic liquid is receiving more and more attention as a novel environment-friendly component.
With the rapid development of technology and increasingly stringent emissions regulations, the requirements on lubricant performance are becoming more stringent. Traditional lubrication is highly limited in practicality due to the characteristics of high oxidizing property and thermal instability, easiness in overheat decomposition and the like. Along with the improvement of people's environmental awareness, lubrication technology gradually develops to high-efficient, environmental protection direction. For example, vegetable oil rich in resources is used for replacing mineral oil, synthetic ester with excellent comprehensive performance and long service life is used as base oil, but the synthetic ester is still limited to be directly used as a lubricant due to the problems of thermal oxidation stability, viscosity and the like.
Disclosure of Invention
The invention aims to provide a high-extreme-pressure ionic liquid, a preparation method and application thereof as an oil-based additive. The aim of the invention is achieved by the following technical scheme:
The high-pressure ionic liquid has a structural general formula of A +B-, wherein A + is an organic cation, B - is an organic anion, the organic cation is an alkylamine cation, and the anion is a phosphate anion.
Further, the phosphate anion refers to at least one of bis (2-ethylhexyl) phosphate anion, dibutyl phosphate anion, isopropyl phosphate anion and triethyl phosphate anion, preferably bis (2-ethylhexyl) phosphate anion.
Further, the phosphate anion refers to at least one of bis (2-ethylhexyl) phosphate anion, dibutyl phosphate anion, isopropyl phosphate anion and triethyl phosphate anion, preferably dibutyl phosphate anion.
Further, the alkylamine cation refers to at least one of dimethylamine cation, diethylamine cation, diisopropylamine cation and diisobutylamine cation with a carbon chain of 4-18, preferably sixteen tertiary amine cation.
Further, the alkylamine cation refers to at least one of dimethylamine cation, diethylamine cation, diisopropylamine cation and diisobutylamine cation with a carbon chain of 4-18, preferably octadecylamine cation.
The preparation method of the high extreme pressure proton type ionic liquid comprises the following steps: mixing phosphate with alkylamine in equal mass, adding solvent, performing heat treatment, and removing solvent by reduced pressure distillation after the reaction is completed to obtain colorless or pale yellow oily liquid, wherein the reaction route is as follows:
Wherein n=15 or 17; r 1 =methyl and R 2 =n-pentyl or R 1 =ethyl and R 2 =hydrogen.
Further, the temperature of the heat treatment is 40-80 ℃, the reaction time is 12-36 hours, preferably the temperature of the heat treatment is 65 ℃, and the reaction time is 24 hours.
Further, the solvent is at least one of acetonitrile, tetrahydrofuran, petroleum ether and ethyl acetate, preferably acetonitrile.
The use of an ionic liquid of the high extreme pressure type as described above or prepared by the method as described above as an oil-based additive, the ionic liquid being applicable to a variety of ester base oils, the base oil being at least one of rapeseed oil, pentaerythritol oleate, trimethylolpropane oleate and animal oil, preferably rapeseed oil.
Further, the ionic liquid may be applied to various ester base oils, which are at least one of rapeseed oil, pentaerythritol oleate, trimethylolpropane oleate and animal oil, preferably pentaerythritol oleate.
Further, the ionic liquid may be applied to various ester base oils, which are at least one of rapeseed oil, pentaerythritol oleate, trimethylolpropane oleate and animal oil, preferably trimethylolpropane oleate.
The high extreme pressure proton type ionic liquid has the advantages that:
1. the preparation method of the proton type ionic liquid is simple, low in cost and few in component types.
2. The proton type ionic liquid can be uniformly dispersed in the ester base oil, has no layering phenomenon, and can be used as an additive to improve the extreme pressure abrasion resistance of the base oil, wherein the maximum seizure-free load value P B can reach 1570N.
3. The proton type ionic liquid can improve the lubricating property of the ester base oil and is characterized by lower friction coefficient; smaller diameter, smoother surface and smoother surface.
Drawings
The following describes the embodiments of the present invention in further detail with reference to the drawings.
Fig. 1 is an optical photograph of a proton type ionic liquid: from left to right, the synthesized protic ionic liquids (protic ionic liquid I of example 1 and protic ionic liquid II of example 8) were colorless oily liquids.
FIG. 2 is an optical photograph of examples 1-3, examples 6-8 and comparative examples 1-3 according to the present invention: from left to right, the proton type ionic liquid can be uniformly dispersed in the ester base oil, and layering phenomenon is avoided.
Fig. 3 shows the maximum seizure-free load P B values of examples 1 to 3, examples 6 to 8 and comparative examples 1 to 3, and it can be seen that the maximum seizure-free load P B values of the examples are all larger than those of the comparative examples, which indicates that the proton-containing ionic liquid ester lubricating oil prepared by the invention has high lubricating bearing capacity.
FIG. 4 is a graph showing the friction coefficient curves of the addition of the proton-type ionic liquids prepared in examples 1 to 3, examples 6 to 7, and comparative examples 1 to 3 to the ester base oils according to the present invention. It can be seen that the coefficient of friction of each example is close to or lower than 0.06, and the coefficient of friction of the comparative example is significantly higher than that of the example under the same test conditions, which illustrates that the ionic liquid of the proton type is used as an additive to enable the ionic liquid to have better lubricating performance.
FIG. 5 is a plot of the addition of the proton-type ionic liquids prepared in examples 1-3, examples 6-7, and comparative examples 1-3 to ester base oils in accordance with the present invention. Table 1 shows the results of the plaque diameters obtained in examples 1 to 8 and comparative examples 1 to 3. It can be seen that under the same test conditions, the abrasive spot diameter of each example is obviously smaller than that of the comparative example, and the abrasive spots are flat and smooth, which indicates that the proton type ionic liquid provided by the invention enables the ester base oil to have better lubricating and wear-resisting properties.
Fig. 6 shows the friction coefficient curve (a) and the corresponding mill-spot diameter (b) of the proton-type ionic liquid prepared in example 4 according to the present invention added to the ester base oil. It can be seen that the load was increased from 296N to 510N, the coefficient of friction was 0.05, which was significantly lower than that of comparative example 2, the plaque diameter (WSD) was 0.317mm, which was much smaller than that of comparative example 2, and the surface was smooth and flat, indicating that the system was applicable to a wide application load range, and good lubricating properties.
Fig. 7 shows the friction coefficient curve (a) and the corresponding mill-spot diameter (b) of the proton-type ionic liquid prepared in example 5 according to the present invention added to the ester base oil. It can be seen that the load was further increased to 696N, the coefficient of friction was 0.058, and still significantly lower than that of comparative example 2, and under this condition, the plaque diameter (WSD) was 0.352mm, and it can be seen that although the load was increased, the plaque diameter was still much smaller than that of comparative example 2, and the surface was smooth and flat, indicating that the system was applicable to a wide application load range, and good lubricating property.
Fig. 8 shows the friction coefficient curve (a) and the corresponding mill-spot diameter (b) of the proton-type ionic liquid prepared in example 8 according to the present invention added to the ester base oil. It can be seen that the proton type ionic liquid has a wide application range, various phosphate esters can be applied to an ester base oil system, the friction coefficient is about 0.061, which is obviously lower than that of comparative example 1, the diameter of the abrasive spots is 0.342mm, which is far lower than that of comparative example 1, so that the ester base oil can have better lubrication and wear resistance.
Detailed Description
The technical scheme of the present invention will be described in further detail with reference to the accompanying drawings and examples, but the scope of the present invention is not limited thereto.
Example 1
20G of bis (2-ethylhexyl) phosphate and 60mL of acetonitrile are added into a reaction kettle, stirred uniformly, octadecyl tertiary amine with the mass of the bis (2-ethylhexyl) phosphate and the like is added, stirred at 65 ℃ for 24 hours, and the solvent is removed by reduced pressure distillation, so that colorless or pale yellow oily liquid, namely proton type ionic liquid I (shown in the following formula) is obtained.
Taking 0.2g of proton type ionic liquid I, 39.8g of rapeseed oil, and uniformly mixing to perform tribological property test.
The prepared base oil was tested for tribological properties using a four-ball friction tester (MS-10A). The steel ball used in the test is GCr15 bearing steel ball. The test conditions were a coefficient of friction (COF) at room temperature under a load of 296N at a rotational speed of 1200r/min for 30 min. The surface of the steel ball was examined for plaque diameter using an XDS-0745D optical microscope and a MicroXAM3D non-contact surface tester, and the results are shown in Table 1.
Example 2
0.8G of proton type ionic liquid I (same as in example 1) and 39.2g of rapeseed oil are uniformly mixed for testing tribological properties.
The test conditions were the same as in example 1, and the test results are shown in Table 1.
Example 3
2G of proton type ionic liquid I (same as in example 1) and 38g of rapeseed oil are uniformly mixed for tribological performance test.
The test conditions were the same as in example 1, and the test results are shown in Table 1.
Example 4
A preparation method of a proton type ionic liquid is the same as that of example 2.
The prepared base oil was tested for tribological properties using a four-ball friction tester (MS-10A). The steel ball used in the test is GCr15 bearing steel ball. The test conditions were a coefficient of friction (COF) at room temperature under a load of 510N at a rotational speed of 1200r/min for 30 min. The surface of the steel ball was examined for plaque diameter using an XDS-0745D optical microscope and a MicroXAM3D non-contact surface tester, and the results are shown in Table 1.
Example 5
A preparation method of a proton type ionic liquid is the same as that of example 2.
The tribological properties of the prepared cutting lubricating fluid were tested using a four-ball friction tester (MS-10A). The steel ball used in the test isGCr15 bearing steel ball. The test conditions were a coefficient of friction (COF) at room temperature under a load of 696N at a rotational speed of 1200r/min for 30 min. The surface of the steel ball was examined for plaque diameter using an XDS-0745D optical microscope and a MicroXAM3D non-contact surface tester, and the results are shown in Table 1.
Example 6
0.8G of proton type ionic liquid I (same as in example 1), 39.2g of trimethylolpropane oleate, and carrying out tribological property test after uniformly mixing.
The test conditions were the same as in example 1, and the test results are shown in Table 1.
Example 7
0.8G of proton type ionic liquid I (same as in example 1) and 39.2g of pentaerythritol oleate are uniformly mixed and subjected to tribological property test.
The test conditions were the same as in example 1, and the test results are shown in Table 1.
Example 8
Adding 20g of dibutyl phosphate and 30mL of acetonitrile into a reaction kettle, stirring uniformly, adding octadecyl tertiary amine with the mass of dibutyl phosphate and the like, stirring at 65 ℃ for 24 hours, and distilling under reduced pressure to remove the solvent to obtain colorless or pale yellow oily liquid which is proton type ionic liquid II (shown in the following formula).
Taking 0.2g of proton type ionic liquid IIand 39.8g of rapeseed oil, and uniformly mixing to perform tribological property test.
The prepared base oil was tested for tribological properties using a four-ball friction tester (MS-10A). The steel ball used in the test is GCr15 bearing steel ball. The test conditions were a coefficient of friction (COF) at room temperature under a load of 296N at a rotational speed of 1200r/min for 30 min. The surface of the steel ball was examined for plaque diameter using an XDS-0745D optical microscope and a MicroXAM3D non-contact surface tester, and the results are shown in Table 1.
Comparative example 1
20G of commercially available rapeseed oil.
The test conditions were the same as in example 1, and the test results are shown in Table 1.
Comparative example 2
Commercial trimethylolpropane oleate 20g.
The test conditions were the same as in example 1, and the test results are shown in Table 1.
Comparative example 3
Pentaerythritol oleate is commercially available in 20g.
The test conditions were the same as in example 1, and the test results are shown in Table 1.
Table 1 plaque diameter of base oils obtained in examples 1 to 8 and comparative examples 1 to 3
The present invention is not described in detail in part as being well known to those skilled in the art. The above examples are merely illustrative of preferred embodiments of the invention, which are not exhaustive of all details, nor are they intended to limit the invention to the particular embodiments disclosed. Various modifications and improvements of the technical scheme of the present invention will fall within the protection scope of the present invention as defined in the claims without departing from the design spirit of the present invention.
Claims (3)
1. A high-pressure ionic liquid is characterized in that: the structural general formula of the proton type ionic liquid is shown as follows:
wherein n=15, r1=methyl and r2=n-pentyl; or n=17, r1=methyl and r2=n-pentyl; or n=17, r1=ethyl and r2=hydrogen.
2. The method for preparing the high extreme pressure proton type ionic liquid as claimed in claim 1, which is characterized in that: the preparation method of the proton type ionic liquid comprises the following steps: mixing phosphate with alkylamine in equal mass, adding solvent, heat treating, and removing solvent by reduced pressure distillation to obtain colorless or pale yellow oily liquid, wherein the reaction route is as follows:
。
3. the use of a high extreme pressure protic ionic liquid as oil-based additives as claimed in claim 1, characterized in that: the ionic liquid is applied to various ester base oils, and the base oil is at least one of rapeseed oil, pentaerythritol oleate, trimethylolpropane oleate and animal oil.
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| US4077860A (en) * | 1976-12-29 | 1978-03-07 | Stauffer Chemical Company | Photopolymerizable composition stabilized with ammonium salts of phosphorus acid and process |
| CN1785524A (en) * | 2004-12-08 | 2006-06-14 | 北京化工大学 | Room temperature ionic liquid and its preparation method |
| JP2008291231A (en) * | 2007-04-23 | 2008-12-04 | Nippon Synthetic Chem Ind Co Ltd:The | Ionic liquid composition and synthetic lubricant comprising the same |
| CN111574560A (en) * | 2020-06-03 | 2020-08-25 | 辽宁大学 | Phosphorus-containing ionic liquid and preparation method and application thereof |
| CN111778084A (en) * | 2020-06-19 | 2020-10-16 | 中国科学院兰州化学物理研究所 | Antioxidant composition for lubricating oil |
| CN113046163A (en) * | 2021-03-25 | 2021-06-29 | 中国科学院兰州化学物理研究所 | Water-based cutting lubricating fluid with ultralow friction coefficient |
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4077860A (en) * | 1976-12-29 | 1978-03-07 | Stauffer Chemical Company | Photopolymerizable composition stabilized with ammonium salts of phosphorus acid and process |
| CN1785524A (en) * | 2004-12-08 | 2006-06-14 | 北京化工大学 | Room temperature ionic liquid and its preparation method |
| JP2008291231A (en) * | 2007-04-23 | 2008-12-04 | Nippon Synthetic Chem Ind Co Ltd:The | Ionic liquid composition and synthetic lubricant comprising the same |
| CN111574560A (en) * | 2020-06-03 | 2020-08-25 | 辽宁大学 | Phosphorus-containing ionic liquid and preparation method and application thereof |
| CN111778084A (en) * | 2020-06-19 | 2020-10-16 | 中国科学院兰州化学物理研究所 | Antioxidant composition for lubricating oil |
| CN113046163A (en) * | 2021-03-25 | 2021-06-29 | 中国科学院兰州化学物理研究所 | Water-based cutting lubricating fluid with ultralow friction coefficient |
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