CN109503503B - Multifunctional ionic liquid and preparation method and application thereof - Google Patents
Multifunctional ionic liquid and preparation method and application thereof Download PDFInfo
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- CN109503503B CN109503503B CN201811568453.9A CN201811568453A CN109503503B CN 109503503 B CN109503503 B CN 109503503B CN 201811568453 A CN201811568453 A CN 201811568453A CN 109503503 B CN109503503 B CN 109503503B
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 112
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 12
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 11
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 11
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims abstract description 11
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 11
- 238000005260 corrosion Methods 0.000 claims description 34
- 230000007797 corrosion Effects 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 27
- 229910052802 copper Inorganic materials 0.000 claims description 27
- 239000010949 copper Substances 0.000 claims description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- 239000002199 base oil Substances 0.000 claims description 20
- 239000003112 inhibitor Substances 0.000 claims description 15
- 238000002390 rotary evaporation Methods 0.000 claims description 11
- -1 aliphatic aldehyde Chemical class 0.000 claims description 10
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 claims description 9
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003879 lubricant additive Substances 0.000 claims description 8
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 7
- 239000012964 benzotriazole Substances 0.000 claims description 7
- 239000012074 organic phase Substances 0.000 claims description 7
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 6
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 claims description 6
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 claims description 6
- 239000013067 intermediate product Substances 0.000 claims description 6
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 claims description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 5
- 150000001565 benzotriazoles Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 claims description 4
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 4
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 4
- SNAMIIGIIUQQSP-UHFFFAOYSA-N bis(6-methylheptyl) hydrogen phosphate Chemical compound CC(C)CCCCCOP(O)(=O)OCCCCCC(C)C SNAMIIGIIUQQSP-UHFFFAOYSA-N 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 4
- 229920002866 paraformaldehyde Polymers 0.000 claims description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 3
- HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 150000002192 fatty aldehydes Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910000831 Steel Inorganic materials 0.000 description 14
- 239000000654 additive Substances 0.000 description 14
- 239000010959 steel Substances 0.000 description 14
- 230000000694 effects Effects 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 229920013639 polyalphaolefin Polymers 0.000 description 10
- 239000002480 mineral oil Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 101150092791 PAO4 gene Proteins 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- 235000010446 mineral oil Nutrition 0.000 description 8
- ZWYAVGUHWPLBGT-UHFFFAOYSA-N bis(6-methylheptyl) decanedioate Chemical compound CC(C)CCCCCOC(=O)CCCCCCCCC(=O)OCCCCCC(C)C ZWYAVGUHWPLBGT-UHFFFAOYSA-N 0.000 description 7
- 239000000314 lubricant Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 230000001603 reducing effect Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000007866 anti-wear additive Substances 0.000 description 4
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 231100000241 scar Toxicity 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 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 description 1
- 101100407030 Arabidopsis thaliana PAO2 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 239000013556 antirust agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- PZZHMLOHNYWKIK-UHFFFAOYSA-N eddha Chemical compound C=1C=CC=C(O)C=1C(C(=O)O)NCCNC(C(O)=O)C1=CC=CC=C1O PZZHMLOHNYWKIK-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 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
- 150000002892 organic cations Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
-
- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
-
- 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
-
- 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
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
Landscapes
- 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)
Abstract
The invention relates to a multifunctional ionic liquid and a preparation method and application thereof, wherein the ionic liquid is represented by the following general formula (1), in the general formula (1), R represents any one of a hydrogen atom or a methyl group, R1 represents any one of a hydrogen atom, a methyl group, a propyl group, a pentyl group, a heptyl group, a nonyl group, an undecyl group and a phenyl group, and R2 represents any one of an octadecyl group or a 9-ene octadecyl group.
Description
Technical Field
The invention relates to the field of lubricating materials, in particular to a multifunctional ionic liquid and a preparation method and application thereof.
Background
Ionic liquids are molten salt systems which are liquid at or near room temperature and are composed entirely of positive and negative ions, and are generally composed of specific, relatively large-volume organic cations and relatively small-volume inorganic or organic anions which are combined by coulomb force. Compared with other solid or liquid materials, the liquid property and the existing form of ions of the material cause the material to show unique physicochemical property and unique function, and the material is a promising novel medium or 'soft' functional material. Due to the designability of the ionic liquid, one or more functional groups are introduced to cations or anions of the ionic liquid, namely, the ionic liquid is functionalized to become a new research hotspot, and the method has great significance for designing and developing novel ionic liquid lubricants.
However, ionic liquid lubricants have many problems that are not negligible while having excellent tribological properties. For example, most ionic liquids are readily soluble in more polar base oils and poorly soluble in less polar mineral oils or polyalphaolefins. In addition, the common ionic liquid has a strong surface corrosion effect on various metals such as copper, steel, aluminum and the like, and in the prior art, additives such as a copper corrosion inhibitor or an antirust agent and the like are usually added to inhibit the corrosion of the ionic liquid on metal materials. At present, the research reports related to oil-soluble ionic liquid in China are few, and a patent CN 105254667A discloses a functional oil-soluble ionic liquid and a preparation method and application thereof, quaternary phosphorus or quaternary ammonium cations with different alkyl chain lengths are used, and anions are diisooctyl phosphate (EDHPA), dioctyl isoamyl sulfonate (DOSS), O-Diethyl Dithiophosphate (DDSSP) and laurate, so that the functional oil-soluble ionic liquid has good solubility and lubricating property in 500N and PAO10, and has certain corrosion resistance.
Disclosure of Invention
The invention discloses a multifunctional ionic liquid and a preparation method and application thereof, and solves the technical problems that the ionic liquid in the prior art is poor in solubility in mineral oil or poly-alpha-olefin and has strong corrosivity on metal surfaces.
The invention adopts the following scheme: the ionic liquid is represented by the following general formula (1), wherein in the general formula (1), R represents any one of a hydrogen atom and a methyl group, R1 represents any one of a hydrogen atom, a methyl group, a propyl group, a pentyl group, a heptyl group, a nonyl group, an undecyl group and a phenyl group, and R2 represents any one of an octadecyl group and a 9-alkenyloctadecyl group.
A method of preparing a multifunctional ionic liquid comprising the steps of: adding benzotriazole derivatives, aliphatic aldehyde/aromatic aldehyde and high-carbon-chain aliphatic amine into a flask according to the molar ratio of 1:1.1:1, adding 1-5 wt% hydrochloric acid as a catalyst, reacting for 8-12 h at 50-80 ℃, removing ethanol by rotary evaporation, extracting and separating to obtain an organic phase, removing ethyl acetate to obtain an intermediate product, mixing the intermediate product with diisooctyl phosphate according to the molar ratio of 1:1, and reacting for 2-8 h at 80-100 ℃ to obtain the ionic liquid.
In a preferred embodiment, the benzotriazole derivative is one of benzotriazole or 5-methylbenzotriazole.
As a preferred embodiment, the aliphatic aldehyde is any one of formaldehyde, paraformaldehyde, acetaldehyde, butyraldehyde, hexanal, octanal, decanal, dodecanal.
As a preferred embodiment, the aromatic aldehyde is benzaldehyde.
As a preferred embodiment, the high carbon chain fatty amine is one of oleylamine or octadecylamine.
The application of the ionic liquid as a lubricant additive is represented by the following general formula (1), wherein in the general formula (1), R represents any one of a hydrogen atom or a methyl group, R1 represents any one of a hydrogen atom, a methyl group, a propyl group, a pentyl group, a heptyl group, a nonyl group, an undecyl group and a phenyl group, and R2 represents any one of an octadecyl group or a 9-ene octadecyl group.
As a preferred embodiment, the lubricant additive is added to the base oil in an amount of 0.2 wt% to 2 wt%.
The application of the multifunctional ionic liquid is characterized in that the ionic liquid is used as a copper corrosion inhibitor, and the dosage of the ionic liquid as the copper corrosion inhibitor is 0.1-1 wt%.
The copper corrosion inhibitor is prepared from an ionic liquid, wherein the ionic liquid is represented by the following general formula (1), in the general formula (1), R represents any one of a hydrogen atom or a methyl group, R1 represents any one of a hydrogen atom, a methyl group, a propyl group, a pentyl group, a heptyl group, a nonyl group, an undecyl group and a phenyl group, R2 represents any one of an octadecyl group or a 9-ene octadecyl group, and the dosage of the ionic liquid is 0.1-1 wt%.
The invention has the beneficial effects that: compared with the conventional ionic liquid (containing fluorine anions), the preparation method has simpler steps and lower product cost; the oil solubility is good, the compatibility with the traditional base oil is good, for example, the oil has good compatibility with the base oil such as poly-alpha-olefin (PAO), mineral oil, polyether, synthetic ester and the like, and the application range of the oil as an additive is wide; the tribological performance is excellent in various base oils; has copper corrosion inhibiting performance and still shows excellent copper corrosion inhibiting performance in the presence of sulfur-containing additive.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to specific embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
A multifunctional ionic liquid is represented by the following general formula (1), wherein in the general formula (1), R represents any one of a hydrogen atom and a methyl group, R1 represents any one of a hydrogen atom, a methyl group, a propyl group, a pentyl group, a heptyl group, a nonyl group, an undecyl group and a phenyl group, and R2 represents any one of an octadecyl group and a 9-alkenyloctadecyl group.
A method for preparing multifunctional ionic liquid comprises the following steps: adding benzotriazole derivatives, aliphatic aldehyde/aromatic aldehyde and high-carbon-chain aliphatic amine into a flask according to a molar ratio of 1:1.1:1, adding 1-5 wt% hydrochloric acid as a catalyst, reacting for 8-12 h at 50-80 ℃, removing ethanol by rotary evaporation, performing extraction separation to obtain an organic phase, removing ethyl acetate to obtain an intermediate product, and reacting the intermediate product with diisooctyl phosphate at 80-100 ℃ for 2-8 h according to the molar ratio of 1:1 to obtain the ionic liquid. The benzotriazole derivative is one of benzotriazole or 5-methylbenzotriazole, the aliphatic aldehyde is any one of formaldehyde, paraformaldehyde, acetaldehyde, butyraldehyde, hexanal, octanal, decanal and dodecanal, the aromatic aldehyde is benzaldehyde, and the high-carbon-chain aliphatic amine is one of oleylamine or octadecylamine.
The application of the ionic liquid as a lubricant additive is represented by the following general formula (1), wherein in the general formula (1), R represents any one of a hydrogen atom or a methyl group, R1 represents any one of a hydrogen atom, a methyl group, a propyl group, a pentyl group, a heptyl group, a nonyl group, an undecyl group and a phenyl group, and R2 represents any one of an octadecyl group or a 9-ene octadecyl group. The lubricant additive is added into the base oil in an amount of 0.2 wt% to 2 wt%.
The base oil refers to poly-alpha-olefin (PAO), mineral oil, polyether, synthetic ester base oil and the like, and the poly-alpha-olefin (PAO) mainly refers to PAO2, PAO4, PAO10, PAO40, PAO100, PAO150 and PAO 300; the mineral oil refers to API I, API II and API III mineral base oil, and is typically 150SN, 500N and 100N; the polyether mainly refers to OSP46 and OSP 68; the synthetic ester refers to diester, trimellitate and polyol ester, and is typically one of diisooctyl sebacate, isooctyl trimellitate and trimethylolpropane oleate. It can be seen that the present application also provides a lubricant.
Further, the application of the multifunctional ionic liquid is that the ionic liquid is used as a copper corrosion inhibitor, and the dosage of the ionic liquid as the copper corrosion inhibitor is 0.1wt% -1 wt%.
The copper corrosion inhibitor is prepared from an ionic liquid, wherein the ionic liquid is represented by the following general formula (1), in the general formula (1), R represents any one of a hydrogen atom or a methyl group, R1 represents any one of a hydrogen atom, a methyl group, a propyl group, a pentyl group, a heptyl group, a nonyl group, an undecyl group and a phenyl group, R2 represents any one of an octadecyl group or a 9-ene octadecyl group, and the dosage of the ionic liquid is 0.1-1 wt%.
Example 1
A preparation method of a multifunctional ionic liquid comprises the steps of adding 11.9g of benzotriazole, 8.9g of formaldehyde solution and 26.7g of oleylamine into a 250ml single-neck flask, adding 100g of ethanol and 0.475g of hydrochloric acid, stirring at 50 ℃ for 12 hours, and finishing the reaction. Ethanol was removed by rotary evaporation. Gradually adding saturated sodium bicarbonate solution with equal molar amount of hydrochloric acid into the flask, continuously stirring, adding 100ml of ethyl acetate for extraction, washing with water for three times to obtain an organic phase, and performing rotary evaporation to remove the ethyl acetate to obtain a light yellow liquid product N- (benzotriazole-1-methylene) oleylamine. 19.9g of the product and 16.1g of dioctyl phosphate are added into a 100ml single-neck flask, and the mixture is stirred for 2 hours at 100 ℃ to obtain an ionic liquid.
The ionic liquid obtained in the step is used as a lubricant and added into base oil to be used as an anti-wear additive, and the dosage is 0.2 wt% -2 wt%.
The ionic liquid obtained in the step is used as a copper corrosion inhibitor, and the dosage of the ionic liquid is 0.1-1 wt%.
Example 2
A preparation method of a multifunctional ionic liquid comprises the steps of adding 11.9g of benzotriazole, 3.3g of paraformaldehyde and 26.9g of octadecylamine into a 250ml single-neck flask, adding 100g of ethanol and 0.475g of hydrochloric acid, stirring at 80 ℃ for 6 hours, and finishing the reaction. Ethanol was removed by rotary evaporation. Gradually adding saturated sodium bicarbonate solution with equal molar amount of hydrochloric acid into the flask, continuously stirring, then adding 100ml of ethyl acetate for extraction, washing for three times to obtain an organic phase, and removing the ethyl acetate by rotary evaporation to obtain a light yellow solid product N- (benzotriazole-1-methylene) octadecylamine. 20g of the product and 16.1g of dioctyl phosphate are added into a 100ml single-neck flask, and the mixture is stirred for 4 hours at 100 ℃ to obtain an ionic liquid.
The ionic liquid obtained in the step is used as a lubricant and added into base oil to be used as an anti-wear additive, and the dosage is 0.2 wt% -2 wt%.
The ionic liquid obtained in the step is used as a copper corrosion inhibitor, and the dosage of the ionic liquid is 0.1-1 wt%.
Example 3
13.32g of 5-methylbenzotriazole, 7.93 g of n-butyl aldehyde and 26.7g of oleylamine are added into a 250ml single-neck flask, 100g of ethanol and 0.916g of hydrochloric acid are added, stirring is carried out at 70 ℃ for 8 hours, and the reaction is finished. Ethanol was removed by rotary evaporation. Gradually adding saturated sodium bicarbonate solution with equal molar amount of hydrochloric acid into the flask, continuously stirring, then adding 100ml of ethyl acetate for extraction, washing for three times to obtain an organic phase, performing rotary evaporation to remove the ethyl acetate to obtain a light yellow liquid product 1- (5-methylbenzotriazole-1- (propyl) methine) oleylamine, taking 22.7g of the product and 16.1g of dioctyl phosphate, adding the product into a 100ml single-neck flask, and stirring for 8 hours at 80 ℃ to obtain the ionic liquid.
The ionic liquid obtained in the step is used as a lubricant and added into base oil to be used as an anti-wear additive, and the dosage is 0.2 wt% -2 wt%.
The ionic liquid obtained in the step is used as a copper corrosion inhibitor, and the dosage of the ionic liquid is 0.1-1 wt%.
Example 4
A preparation method of a multifunctional ionic liquid comprises the steps of adding 5.95g of benzotriazole, 5.84g of benzaldehyde and 13.35g of oleylamine into a 150ml single-neck flask, adding 50g of ethanol and 1.23g of hydrochloric acid, stirring at 80 ℃ for 10 hours, and finishing the reaction. Removing ethanol by rotary evaporation, gradually adding saturated sodium bicarbonate solution with equal molar amount of hydrochloric acid, continuously stirring, adding 100ml of ethyl acetate for extraction, washing with water for three times to obtain an organic phase, and removing the ethyl acetate by rotary evaporation to obtain a light yellow product N- (benzotriazole-1- (phenyl) methine) oleylamine. 11.85g of the product and 8.05g of dioctyl phosphate are added into a 50ml single-neck flask, and the mixture is stirred for 6 hours at 90 ℃ to obtain an ionic liquid.
The ionic liquid obtained in the step is used as a lubricant and added into base oil to be used as an anti-wear additive, and the dosage is 0.2 wt% -2 wt%.
The ionic liquid obtained in the step is used as a copper corrosion inhibitor, and the dosage of the ionic liquid is 0.1-1 wt%.
The ionic liquids obtained in examples 1 to 4 are represented by the general formula (1), wherein in the general formula (1), R represents any one of a hydrogen atom and a methyl group, R1 represents any one of a hydrogen atom, a methyl group, a propyl group, a pentyl group, a heptyl group, a nonyl group, an undecyl group, and a phenyl group, and R2 represents any one of an octadecyl group and a 9-octadecenyl group.
Examples of the experiments
In order to further illustrate the performance of the prepared ionic liquid, experiments are carried out from three aspects of solubility, abrasion resistance and friction reduction and corrosion resistance.
Solubility test
The ionic liquids of examples 1-4 have good solubility in base oils, and the solubility of the ionic liquids in various types of base oils is shown in Table 1.
TABLE 1 solubility of Ionic liquids in different types of base oils
As can be seen from the results of table 1, the ionic liquids obtained in examples 1 to 4 all exhibited excellent solubility properties in different types of base oils.
Examples 1 and 2 frictional wear testing of ionic liquids
The friction performance of the ionic liquid prepared in the example 1-2 in poly alpha-olefin and mineral oil is measured by adopting a four-ball friction wear testing machine produced by a Xiamen celestial machine, the material GCR15 of the steel ball has the diameter of 12.7 mm and the hardness of HRC59-61, and the test conditions are as follows: the load is 392N, the temperature is 25 ℃, the time is 30min, and the rotating speed is 1200 r/min.
The ionic liquid of example 1 was used as an additive to the PAO4 as an experimental group and the PAO4 without the ionic liquid as a control group, and the average coefficient of friction and the size of the wear scar diameter for the steel/steel friction pair are shown in table 2.
TABLE 2 example 1 use of ionic liquids for antiwear and antifriction effects of PAO4 additives
As can be seen from Table 2, the PAO4 without added ionic liquid had an average coefficient of friction of 0.075 and a scrub spot diameter of 0.631 mm. Compared with PAO4, the PAO4 added with different amounts of the ionic liquid in the embodiment 1 has obviously improved friction reducing and wear resisting effects, when the adding amount of the ionic liquid is 0.5 wt%, the average friction coefficient is 0.060 to the minimum, the friction reducing effect is optimal, when the adding amount is 0.2 wt%, the diameter of the wear scar is 0.326 to the minimum, and the wear resisting effect is optimal.
The ionic liquid of example 2 was used as an additive to mineral oil 500N as an experimental group and mineral oil 500N without the ionic liquid as a comparative group, and the average coefficient of friction and the size of the wear scar diameter for the steel/steel friction pair of the two groups are shown in table 3.
Table 3 example 2 anti-wear and anti-friction effect of ionic liquids as mineral oil 500N additives
As can be seen from Table 3, the experimental results show that the friction reducing and wear resisting properties of the 500N with the ionic liquid obtained in example 2 are significantly improved compared with the 500N without the ionic liquid. When the addition amount of the ionic liquid in the embodiment 2 is 2 wt%, the average friction coefficient is minimum 0.066, and the friction reducing effect is optimal; when the addition amount is 0.5 wt%, the minimum diameter of the wear-resisting spot is 0.313, and the best anti-wear effect is achieved.
Friction and wear test of ionic liquids of example 3 and example 4
The ionic liquids prepared in examples 3-4 were evaluated for their frictional wear properties as lubricant additives using a SRV-V microvibration frictional wear tester manufactured by Optimol grease, Germany. Wherein the steel ball of the upper friction pair is a GCr15(SAE52100) steel ball with the diameter of 10mm, the steel block of the lower friction pair is a steel block, and the hardness is HRC 59-61. The test conditions are as follows: the load was 200N, the temperature was 100 deg.C, the time was 30min, and the frequency was 25 Hz.
Example 3 ionic liquid as OSP46 additive was used as an experimental group with 4 groups each with different addition levels and OSP46 as a comparative group with the average coefficient of friction and wear volume at steel/steel friction pairs for the experimental and comparative groups shown in table 4.
Table 4 example 3 anti-wear and anti-friction effect of ionic liquids as OSP46 additive
As can be seen from table 4, both the friction reducing and antiwear properties of OSP46 with the addition of the ionic liquid of example 3 were greatly improved compared to the base oil OSP 46. When the addition amount is 2 wt%, the average friction coefficient is minimum, and the friction reducing effect is optimal. When the addition amount is 2 wt%, the wear volume is minimum, and the wear-resistant effect is optimal.
Example 4 ionic liquid as diisooctyl sebacate additive as experimental group, the experimental group has 4 small groups, the addition amount is different, and diisooctyl sebacate without ionic liquid as comparison group, the experimental conditions are as follows: the load was 200N, the temperature was 25 deg.C, the time was 30min, and the frequency was 25 Hz. The average friction coefficient and wear volume for the steel/steel friction pairs for the experimental and comparative groups are shown in table 5.
TABLE 5 example 4 antiwear and antifriction Effect of ionic liquids as Diisooctyl sebacate additives
As can be seen from Table 5, the diisooctyl sebacate added with the ionic liquid of example 4 is improved in both friction reducing and wear resistance properties compared to diisooctyl sebacate. Wherein the addition amount is 0.5 wt%, the average friction coefficient is minimum, and the antifriction effect is optimal; the addition amount is 0.5 wt%, the abrasion volume is minimum, and the abrasion resistant effect is optimal.
Copper sheet corrosion test
The ionic liquids prepared in examples 1 to 4 were evaluated for corrosion resistance by the copper sheet corrosion test (GB/T7326-87). In order to further examine the effect of the prepared ionic liquid as a copper corrosion inhibitor, sulfur-containing additives RC2540, RC2526, zinc dialkyl dithiophosphate and sulfurized isobutylene are respectively added into base oil to carry out a copper sheet corrosion test. RC2540 and RC2526 are additive brands of Rhine chemical company, belong to active sulfur additives, wherein on the basis of adding RC25401 wt% of PAO4, the ionic liquid which is not added is used as a comparative group 1, and 1wt% of the ionic liquid in experiment example 1 is added as an experiment group 1, and corrosion resistance comparison is carried out; on the basis of 500N added with RC25261 wt%, the ionic liquid not added is used as a comparison group 2, and 0.8 wt% of the ionic liquid in the experimental example 2 is used as an experimental group 2, so that corrosion resistance performance comparison is carried out; on the basis of OSP46 with 1wt% of zinc dialkyldithiophosphate added, the one without ionic liquid added is taken as a comparative group 3, and 0.5 wt% of ionic liquid of Experimental example 3 is added as an experimental group 3; on the basis of the addition of diisooctyl sebacate, which sulfurized isobutylene 1wt%, the one without ionic liquid was added as comparative 4, and the one of example 4, which ionic liquid 0.1wt%, was added as experimental group 4. The corrosion test results for the copper sheets of the above groups are shown in Table 6.
TABLE 6 copper sheet Corrosion test results
As can be seen from Table 6, the corrosion rating of the copper sheet of experimental group 1 was reduced from 4b to 1b, compared to comparative group 1; the corrosion grade of the copper sheet of experimental group 2 was reduced from 4a to 1b compared to comparative group 2; the corrosion grade of the copper sheet of experimental group 3 was reduced from 3a to 1b compared to comparative group 3; the corrosion rating of the copper sheet of experimental group 4 was reduced from 1b to 1a compared to comparative group 4. Therefore, the ionic liquids prepared in examples 1 to 4 all have better corrosion resistance.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (8)
1. The multifunctional ionic liquid is characterized by being represented by the following general formula (1), wherein in the general formula (1), R represents any one of a hydrogen atom or a methyl group, and R1Represents any one of a hydrogen atom, a methyl group, a propyl group, a pentyl group, a heptyl group, a nonyl group, an undecyl group and a phenyl group, R2Represents any one of octadecyl or 9-alkenyloctadecyl, and formula (1) is as follows,
2. a method of making the multifunctional ionic liquid of claim 1, comprising the steps of: adding benzotriazole derivatives, aliphatic aldehyde/aromatic aldehyde and high-carbon-chain aliphatic amine into a flask according to a molar ratio of 1:1.1:1, adding 1-5 wt% hydrochloric acid as a catalyst, reacting for 8-12 h at 50-80 ℃, removing ethanol by rotary evaporation, performing extraction separation to obtain an organic phase, removing ethyl acetate to obtain an intermediate product, and reacting the intermediate product with diisooctyl phosphate for 2-8 h at 80-100 ℃ according to a molar ratio of 1:1 to obtain the ionic liquid;
the derivative of the benzotriazole is one of benzotriazole or 5-methylbenzotriazole, and the high-carbon-chain fatty amine is one of oleylamine or octadecylamine.
3. The method of claim 2, wherein the fatty aldehyde is any one of formaldehyde, paraformaldehyde, acetaldehyde, butyraldehyde, hexanal, octanal, decanal, and dodecanal.
4. A process according to claim 3 for preparing the multifunctional ionic liquid of claim 1 wherein the aromatic aldehyde is benzaldehyde.
5. The application of the ionic liquid as the lubricant additive is characterized in that the ionic liquid is represented by the following general formula (1), wherein in the general formula (1), R represents any one of hydrogen atoms or methyl groups1Represents any one of a hydrogen atom, a methyl group, a propyl group, a pentyl group, a heptyl group, a nonyl group, an undecyl group and a phenyl group,
R2represents any one of octadecyl and 9-alkenyloctadecyl, and formula (1) is as follows,
6. the use of an ionic liquid as a lubricant additive according to claim 5, wherein the lubricant additive is added to the base oil in an amount of 0.2 wt% to 2 wt%.
7. The use of the multifunctional ionic liquid of claim 1, wherein the ionic liquid is used as a copper corrosion inhibitor, and the amount of the ionic liquid used as a copper corrosion inhibitor is 0.1wt% to 1 wt%.
8. A copper corrosion inhibitor made of an ionic liquid, characterized in that the ionic liquid is represented by the following general formula (1), wherein R represents any one of a hydrogen atom and a methyl group, and R represents1Represents any one of a hydrogen atom, a methyl group, a propyl group, a pentyl group, a heptyl group, a nonyl group, an undecyl group and a phenyl group, R2Represents any one of octadecyl or 9-ene octadecyl, the dosage of the ionic liquid is 0.1wt% -1 wt%,
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