CN115960650A - Lubricating oil composition for air compressor and preparation method thereof - Google Patents
Lubricating oil composition for air compressor and preparation method thereof Download PDFInfo
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- CN115960650A CN115960650A CN202111186803.7A CN202111186803A CN115960650A CN 115960650 A CN115960650 A CN 115960650A CN 202111186803 A CN202111186803 A CN 202111186803A CN 115960650 A CN115960650 A CN 115960650A
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- 239000010687 lubricating oil Substances 0.000 title claims abstract description 40
- 239000000203 mixture Substances 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title description 6
- 239000002199 base oil Substances 0.000 claims abstract description 13
- 150000001639 boron compounds Chemical class 0.000 claims abstract description 13
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 12
- 230000001050 lubricating effect Effects 0.000 claims abstract description 12
- 150000002148 esters Chemical class 0.000 claims abstract description 11
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 10
- 239000002518 antifoaming agent Substances 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- 229910052799 carbon Inorganic materials 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 125000002947 alkylene group Chemical group 0.000 claims description 28
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 20
- 229910052796 boron Inorganic materials 0.000 claims description 20
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 claims description 16
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 claims description 16
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 claims description 16
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 claims description 16
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 13
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 10
- 239000004327 boric acid Substances 0.000 claims description 10
- -1 thiophosphoric acid amine salts Chemical class 0.000 claims description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 9
- 230000035484 reaction time Effects 0.000 claims description 7
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000002978 peroxides Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- VLKQQIZFPCDLRZ-UHFFFAOYSA-N OO[S](=O)=O Chemical compound OO[S](=O)=O VLKQQIZFPCDLRZ-UHFFFAOYSA-N 0.000 claims description 3
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000008301 phosphite esters Chemical class 0.000 claims description 3
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims description 2
- XYFRHHAYSXIKGH-UHFFFAOYSA-N 3-(5-methoxy-2-methoxycarbonyl-1h-indol-3-yl)prop-2-enoic acid Chemical compound C1=C(OC)C=C2C(C=CC(O)=O)=C(C(=O)OC)NC2=C1 XYFRHHAYSXIKGH-UHFFFAOYSA-N 0.000 claims description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 2
- 229910011255 B2O3 Inorganic materials 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000002530 phenolic antioxidant Substances 0.000 claims description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 2
- 229920002545 silicone oil Polymers 0.000 claims description 2
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims 1
- 239000012990 dithiocarbamate Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 abstract description 9
- 238000007254 oxidation reaction Methods 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- ZWYAVGUHWPLBGT-UHFFFAOYSA-N bis(6-methylheptyl) decanedioate Chemical compound CC(C)CCCCCOC(=O)CCCCCCCCC(=O)OCCCCCC(C)C ZWYAVGUHWPLBGT-UHFFFAOYSA-N 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- VMZVBRIIHDRYGK-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VMZVBRIIHDRYGK-UHFFFAOYSA-N 0.000 description 1
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 101100407037 Oryza sativa subsp. japonica PAO6 gene Proteins 0.000 description 1
- 101150092791 PAO4 gene Proteins 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 239000006061 abrasive grain Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- CJFLBOQMPJCWLR-UHFFFAOYSA-N bis(6-methylheptyl) hexanedioate Chemical compound CC(C)CCCCCOC(=O)CCCCC(=O)OCCCCCC(C)C CJFLBOQMPJCWLR-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000010725 compressor oil Substances 0.000 description 1
- OSPSWZSRKYCQPF-UHFFFAOYSA-N dibutoxy(oxo)phosphanium Chemical compound CCCCO[P+](=O)OCCCC OSPSWZSRKYCQPF-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000013022 formulation composition Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
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- Lubricants (AREA)
Abstract
The invention provides an air compressor lubricating oil composition, which comprises, by mass, 0.1-10% of an organic boron compound, 0.01-5% of an antioxidant, 0.01-5% of an extreme pressure antiwear agent, 0.001-1% of a defoaming agent and a main amount of ester lubricating base oil, wherein the organic boron compound has a structure shown in formula (I):
Description
Technical Field
The invention relates to lubricating oil, in particular to an air compressor lubricating oil composition and a preparation method thereof.
Background
The air compressor is a universal mechanical device, can provide power and process gas, and is widely applied in the industry. With the development of air compressor technology, higher requirements are put on the performance of the lubricating oil of the air compressor. For the recycled lubricating oil for the air compressor, the lubricating oil needs to have stronger high-temperature oxidation resistance and extreme pressure abrasion resistance. Compared with mineral air compressor lubricating oil, the synthetic air compressor oil has the advantages of good high-low temperature performance, long service life, high cost performance, capability of improving the operation safety coefficient of the compressor, less environmental pollution and the like, can better adapt to the use and the requirement of a novel compressor, and also has the problems of short oil change period, poor high-temperature oxidation resistance and the like.
In the lubricating oil for the air compressor, the antioxidant mainly comprises phenol type, amine type, phenol ester type, thioester type, phosphite ester type and the like, wherein the hindered phenol type antioxidant is widely used. For example, CN 113088368, CN 92102699, CN 99811367, USP 5124057, USP 6207623, USP 6410490 and the like all adopt hindered phenol type antioxidants as one of the antioxidant components, but the common hindered phenol type antioxidants are difficult to meet the requirement of long service life. There remains a need in the art for air compressor lubricating oil compositions that are long-lived and have excellent oxidation stability and antiwear properties.
Disclosure of Invention
The invention provides an air compressor lubricating oil composition and a preparation method thereof.
The air compressor lubricating oil composition comprises, by mass, 0.1-10% of an organoboron compound, 0.01-5% of an antioxidant, 0.01-5% of an extreme pressure antiwear agent, 0.001-1% of a defoaming agent and a main amount of ester lubricating base oil, wherein the organoboron compound has a structure shown in formula (I):
in formula (I), a repeating units L and b boron-containing groups are present, a is an integer between 1 and 10 (preferably an integer between 1 and 5), b is an integer between 1 and 5 (preferably an integer between 1 and 3), a L groups, which are the same or different from each other, are each independently selected from the group represented by formula (II);
in formula (II), HO is bonded to the benzene ring (HO is preferably located on the benzene ring R) 1 Meta to the chain); y R groups are bonded to the benzene ring; y is selected from an integer between 0 and 4 (preferably an integer between 1 and 3); each R group is independently selected from H and C 1-20 Straight or branched chain alkyl (preferably each independently selected from H and C) 1-4 Straight or branched alkyl, more preferably t-butyl); n is an integer of 1 to 10 (preferably an integer of 1 to 3); r 1 Each independently selected from the group consisting of a single bond and C 1-20 Straight or branched alkylene (preferably selected from single bond and C) 1-4 Linear or branched alkylene); r in n repeating units 2 Are the same or different from each other and are each independently selected from the group consisting of a single bond and C 1-20 Straight or branched alkylene (preferably each independently selected from the group consisting of single bond and C) 1-4 Linear or branched alkylene); r 3 Selected from H and C 1-20 Straight or branched alkyl (preferably selected from H and C) 1-4 Straight or branched chain alkyl); the A groups in the n repeating units are the same or different from each other and are independently selected from the group consisting of a single bond, a,
A group of formula (III) and a group of formula (IV),
the R is 4 Each independently selected from H and C 1-20 Straight or branched alkyl (preferably selected from H and C) 1-4 Straight or branched chain alkyl);
m is an integer of 0 to 10 (preferably an integer of 1 to 5);
r is as described 5 Each independently selected from the group consisting of C having a valence of 3 1-20 Straight or branched chain alkyl (preferably each independently selected from the group consisting of C having a valence of 3 1-4 Straight or branched chain alkyl);
each G 2 Each group is independently selected from G present in L groups other than the L group in which it is present 4 Binding end of group bonding, C 1-10 Straight-chain or branched alkyl, -R 6 G 3 H; each G 3 Each independently selected from-OG 1 、C 1-10 A linear or branched alkyl group, H (preferably each independently selected from-OG) 1 、C 1-4 Linear or branched alkyl, OH, H);
said R 6 The radicals being selected from C 1-20 Straight or branched alkylene (preferably each independently selected from C) 1-4 Linear or branched alkylene);
G 1 a group selected from the binding end bonded to the boron-containing group, H;
G 4 the radicals being selected from G present in the L radicals other than the L radical in which they are present 2 A binding end to which a group is bonded, H;
in the a L groups, at least one A group is selected from the group represented by the formula (III), and at least one G group is present 1 The group is selected from binding ends bonded to boron elements in the boron-containing group;
each A' group of the b boron-containing groups is independently selected from the group consisting of G, which is present in the L group 1 A bonding end bonded with the group, a group shown as a formula (V) and-OR ', wherein the R' group is H OR C 1-20 Straight or branched alkyl (preferably H or C) 1-4 Linear or branched alkyl);
in formula (V), m is an integer of 0 to 10 (preferably an integer of 1 to 5);
said R 0 Each independently selected from C 1-10 Straight or branched alkyl, -R 6 G 5 H (preferably each independently selected from C) 1-4 Straight or branched alkyl, -R 6 G 5 、H)；
Said R 5 Each independently selected from the group consisting of C having a valence of 3 1-20 Straight or branched chain alkyl (preferably each independently selected from the group consisting of C having a valence of 3 1-4 Straight or branched chain alkyl);
G 6 the group is selected from-R 6 G 5 、C 1-4 Linear or branched alkyl, H;
said R 6 The radicals being selected from C 1-20 Straight or branched alkylene (preferably each independently selected from C) 1-4 Linear or branched alkylene);
each G 5 Each independently selected from-OG 1 、C 1-4 Straight or branched alkyl, OH, H, wherein G 1 A group selected from a bonding terminal bonded to a boron element in the boron-containing group, C 1-4 Linear or branched alkyl, H;
in the group of formula (V), there is at least one G 1 The group is selected from binding ends bonded to boron elements in the boron-containing group;
in b of said boron-containing groups, at least one A' group is present selected from the group consisting of G and L 1 A binding end to which a group is bonded;
each group in the organoboron compound complies with the bonding rule.
According to the invention, the two binding ends of formula (III) or formula (IV) which are bound to formula (II) can be bound to the group of formula (II) in any manner, for example in one direction to formula (II) or in the opposite direction to formula (II).
Examples of the organoboron compound which may be mentioned according to the invention include one or more of the following structural compounds:
wherein the R group is H or C 1 -C 20 Linear or branched alkyl.
According to the present invention, the method for producing the organoboron compound comprises the steps of:
(1) Reacting a compound represented by formula (X) with a peroxide;
in formula (X), HO is bonded to the phenyl ring (HO is preferably located on the phenyl ring R) 1 Meta to the chain); y R groups are bonded to the benzene ring; y is selected from an integer between 0 and 4 (preferably an integer between 1 and 3); each R group is independently selected from H and C 1-20 Straight or branched chain alkyl (preferably each independently selected from H and C) 1-4 Straight or branched alkyl, more preferably selected from t-butyl); n is an integer of 1 to 10 (preferably an integer of 1 to 3); r 1 Each independently selected from the group consisting of a single bond and C 1-20 Straight or branched alkylene (preferably selected from single bond and C) 1-4 Linear or branched alkylene); r in n repeating units 2 Are the same or different from each other and are each independently selected from the group consisting of a single bond and C 1-20 Straight or branched alkylene (preferably each independently selected from single bond and C) 1-4 Linear or branched alkylene); r 3 Selected from H and C 1-20 Straight or branched alkyl (preferably selected from H and C) 1-4 Straight or branched chain alkyl); a' in the n repeating units are the same or different from each other and are each independently selected from the group consisting of a single bond, a,
Wherein R is 4 Each independently selected from H and C 1-20 Straight or branched chain alkyl (preferably selected from H and C) 1-4 Straight or branched chain alkyl); in formula (X) at least one A' is present which is->
(2) Reacting the reaction product of step (1) with a compound of formula (Y);
in formula (Y), m is an integer of 0 to 10 (preferably an integer of 1 to 5);
said R 0 ' the groups are each independently selected from C 1-10 Straight or branched alkyl, -R 6 OH and H (preferably independently selected from C) 1-4 Straight or branched alkyl, -R 6 OH, H); said R 5 Each independently selected from the group consisting of C having a valence of 3 1-20 Straight or branched chain alkyl (preferably each independently selected from 3 valent C 1-4 Straight or branched chain alkyl); each G 5 ' the groups are each independently selected from C 1-4 Linear or branched alkyl, OH, H; said G 6 ' group is selected from C 1-10 Straight-chain or branched alkyl, -R 6 OH and H; said R 6 Each independently selected from C 1-20 Straight or branched alkylene (preferably each independently selected from C) 1-4 Linear or branched alkylene);
in formula (Y), there is at least one G 5 ' the group is selected from OH or at least one G 6 ' group or R 0 ' the group is selected from-R 6 OH, and at least one R is present 0 ' group or G 6 ' the group is H;
(3) And (3) reacting the reaction product obtained in the step (2) with an inorganic boron compound, and collecting the product.
According to the present invention, in the step (1), the compound represented by the formula (X) may be selected from cardanol, alkylated cardanol, which may be obtained by reacting cardanol with an alkylating agent, for example, tert-butylated cardanol may be obtained by reacting cardanol with tert-butyl chloride.
According to the invention, in step (1), the peroxide is preferably one or more of hydrogen peroxide, peroxyformic acid, peroxyacetic acid, peroxysulfonic acid, m-chloroperoxybenzoic acid, tert-butyl hydroperoxide, tert-butyl peroxyacetate, methyl ethyl ketone peroxide, dibenzoyl peroxide and cyclohexanone peroxide, and more preferably one or more of hydrogen peroxide, peroxyformic acid, peroxyacetic acid and peroxysulfonic acid.
According to the present invention, in step (2), the compound represented by formula (Y) may be selected from one or more of fatty amine, polyenepolyamine, one or more hydroxyl-substituted fatty amine, and one or more hydroxyl-substituted polyenepolyamine, for example, one or more of ethanolamine, diethanolamine, hydroxyethylethylenediamine (i.e., N- (2-hydroxyethyl) ethylenediamine), diethylenetriamine, triethylenetetramine, tetraethylenepentamine, and pentaethylenehexamine may be selected.
According to the present invention, in the step (3), the inorganic boron compound is preferably selected from one or more of boric acid, boric oxide and a boric acid half ester, wherein the boric acid half ester can be selected from monoalkyl borate and dialkyl borate, and the alkyl is C 1 -C 20 Linear or branched alkyl groups of (a).
According to the invention, the equivalent ratio between the compound of formula (X) and the peroxide, the compound of formula (Y), the inorganic boron compound is preferably 1:0.5 to 10:0.5 to 10:0.5 to 5, more preferably 1:2 to 3:2 to 3:1 to 2.
According to the invention, the reaction temperature of step (1) is preferably between 0 and 100 ℃, more preferably between 20 and 80 ℃; the reaction temperature in the step (2) is preferably 50-150 ℃, and more preferably 60-100 ℃; the reaction temperature in step (3) is preferably 80 to 200 ℃ and more preferably 110 to 150 ℃.
According to the present invention, the longer the reaction time in the step (1), the step (2) and the step (3) is, the better, and in general, the reaction time in the step (1) is preferably 1 to 10 hours, more preferably 3 to 5 hours; the reaction time of the step (2) is preferably 1 to 10 hours, and more preferably 2 to 4 hours; the reaction time in step (3) is preferably 1 to 10 hours, more preferably 3 to 5 hours.
According to the present invention, in the reaction of step (3), a compound represented by the formula (Y) may also be added, and the equivalent ratio between the compound represented by the formula (Y) and the inorganic boron compound is preferably 1:0.5 to 5, more preferably 1:0.8 to 3.
According to the present invention, the reaction step (1), (2) or (3) may be carried out in the presence of a diluent and/or a solvent, or may be carried out without using a diluent and/or a solvent.
According to the invention, the diluent may be selected from one or more of the group API group I, II, III, IV and V base oils, the common commercial products or brands include 150SN, 200SN, 350SN, 500SN, 650SN, 150BS, HVI-100, HVI-150, HVI-200, HVI-350, HVI-400, HVI-500, HVI-150BS, PAO4, PAO6, PAO8, PAO10, alkylbenzene, alkylnaphthalene, etc.
According to the invention, the solvent may be selected from C 6-20 Aromatic hydrocarbons (e.g. benzene, toluene, xylene and cumene), C 6-10 Alkanes (such as n-hexane, cyclohexane and petroleum ether), solvent gasoline, etc. These solvents may be used alone or in combination of two or more. The solvent can be distilled off after the end of the reaction in a manner known to those skilled in the art, for example under normal or reduced pressure.
According to a particular embodiment of the present invention, the diluent and/or solvent may be added at any stage of the reaction step in an amount conventional in the art, and is not particularly limited.
According to the present invention, it is evident that said reaction step is generally carried out under protection of an inert gas atmosphere. Examples of the inert gas include nitrogen gas and argon gas, and are not particularly limited.
According to the invention, in the step (3), an accelerator for promoting the reaction to be complete can be added, and common accelerators include water, ethanol, propanol, butanol, ammonia water and the like. If promoters are added, they can be removed after the end of the reaction by means known to the person skilled in the art, for example by distillation under normal or reduced pressure.
According to the present invention, by the aforementioned method for producing an organoboron compound, it is possible to produce a single organoboron compound as a reaction product, it is also possible to produce a mixture composed of plural organoboron compounds, or a mixture composed of one or more of the organoboron compounds and the aforementioned diluent (if used). These reaction products are all intended for the present invention, and the difference in the form of their existence does not affect the achievement of the effects of the present invention. Accordingly, the reaction products are referred to collectively throughout this specification without distinction as organoboron compounds. In view of this, according to the present invention, there is no absolute necessity for further purifying the reaction product or for further separating the organoboron compound of a specific structure from the reaction product. Of course, such purification or isolation is preferable for further improvement of the intended effect of the present invention, but is not essential to the present invention. As the purification or separation method, for example, the reaction product may be purified or separated by a column chromatography method, a preparative chromatography method or the like.
The organic boron compound of the invention has excellent oxidation resistance, wear resistance and friction reduction performance.
According to the invention, the antioxidant is preferably selected from phenolic antioxidants, for example, one or more of 2,6 di-tert-butyl-p-cresol, 2,6-di-tert-butyl mixed ester, 4,4-methylenebis (2,6-di-tert-butylphenol) and 2,6-di-tert-butyl-alpha dimethylamino-p-cresol can be used, and common commercial designations include T501, T512, BHT, and the like.
According to the invention, the extreme pressure antiwear agent is preferably selected from one or more of nitrogen-containing thiophosphoric acid derivatives, phosphate esters, phosphite esters, amine thiophosphate salts, sulfurized olefins and dialkyl dithiocarbamate salts, for example, one or more of nitrogen-containing thiophosphoric acid derivatives, di-n-butyl phosphite, tricresyl phosphate, triethyl phosphate, amine thiophosphate salts, sulfurized isobutylene and zinc dibutyl dithiocarbamate can be selected, and common trade marks include T304, T305, T306, T307, T321 and the like.
According to the invention, the defoaming agent is preferably selected from one or more of acrylic acid and ether copolymer, methyl silicone oil and ethyl silicone oil, and common commercial brands include T911, T912, T901 and the like.
According to the invention, the ester lubricating base oil is preferably a diester lubricating base oil, and for example, diisooctyl sebacate, diisooctyl adipate and the like can be selected.
According to the invention, preferably, the air compressor lubricating oil composition comprises, by mass, 0.2% -5% of an organoboron compound, 0.01% -3% of an antioxidant, 0.01% -3% of an extreme pressure antiwear agent, 0.001% -0.5% of a defoaming agent and a main amount of ester lubricating base oil.
The preparation method of the lubricating oil composition for the air compressor comprises the step of mixing the additive and the lubricating base oil in the lubricating oil composition for the air compressor. The mixing temperature is preferably 40-90 ℃, and the mixing time is preferably 1-6 h.
The lubricating oil composition for the air compressor has excellent high-temperature oxidation resistance and wear resistance, and can meet the requirement of the lubricating oil composition for the long-life air compressor.
Detailed Description
In the present specification, the term "single bond" is sometimes used in the definition of a group. By "single bond" is meant that the group is absent. For example, assume the formula-CH 2 -A-CH 3 Wherein the group a is defined as being selected from the group consisting of a single bond and a methyl group. In this respect, if A is a single bond, this means that the group A is absent, in which case the formula is correspondingly simplified to-CH 2 -CH 3 。
In the context of the present specification, the expression "number + valence + group" or the like refers to a group obtained by removing the number of hydrogen atoms represented by the number from the basic structure (such as a chain, a ring, a combination thereof, or the like) to which the group corresponds, and preferably refers to a group obtained by removing the number of hydrogen atoms represented by the number from a carbon atom (preferably a saturated carbon atom and/or a non-identical carbon atom) contained in the structure. For example, "3-valent straight or branched alkyl" refers to a group obtained by removing 3 hydrogen atoms from a straight or branched alkane (i.e., the base chain to which the straight or branched alkyl corresponds).
The invention is further illustrated by the following examples, which are not to be construed as limiting the invention.
The main raw materials used are as follows:
cardanol, shanghai Bingshi Binghe chemical science & technology Limited, industrial products
Zinc chloride, concentrated sulfuric acid, hydrogen peroxide (30%), formic acid, boric acid, diethanolamine, diethylenetriamine, ethanolamine, N- (2-hydroxyethyl) ethylenediamine, tert-butyl chloride and hexadecanol, which are all purchased from national chemical group, chemical reagent, inc., and analytically pure.
EXAMPLE 1 preparation of tert-butylated epoxy Cardanol
100g of cardanol, 8g of formic acid, 0.3g of sulfuric acid and 200g of hydrogen peroxide are added into a three-neck flask with mechanical stirring, a reflux condenser and temperature control, and stirring and heating are started. The reaction temperature was maintained at 70 ℃ for 3 hours. And cooling after the reaction is finished to obtain a brownish red transparent liquid. Filtering the reaction product, performing alkali washing by using 5-percent KOH solution, then washing by using distilled water until the reaction product is neutral, distilling the organic phase under reduced pressure at the temperature of 150 ℃ and 100Pa for 1h, removing water and unreacted raw materials, and obtaining orange red transparent liquid epoxidized cardanol.
Dissolving 35g of epoxidized cardanol into 100ml of acetone, placing the mixture into a 250ml three-neck reaction flask after the mixture is dissolved, adding 0.9g of zinc chloride catalyst, starting stirring and heating. The reaction temperature was maintained at 60 ℃ and 9.5g of t-butyl chloride was slowly added dropwise to the reaction flask and the reaction was continued for 3 hours after the dropwise addition was completed. And cooling after the reaction is finished to obtain a brownish red transparent liquid. Filtering the reaction product, performing alkali washing by using a 5-percent KOH solution, then washing by using distilled water to be neutral, performing reduced pressure distillation for 1h under the conditions of 1000Pa and 120 ℃, and removing the solvent, water and unreacted raw materials to obtain the brownish red viscous liquid tert-butylated epoxy cardanol.
An exemplary reaction formula of the above reaction is shown in the following formula.
Example 2
22g of t-butylated epoxy cardanol prepared in example 1, 5g N- (2-hydroxyethyl) ethylenediamine and 90g of toluene were added to a 250mL three-necked flask, heated with stirring, and reacted at 90 ℃ for 3 hours. And after the reaction is finished, carrying out reduced pressure distillation for 1h, removing the solvent and unreacted raw materials to obtain dark brown red viscous liquid tert-butyl amino cardanol, then adding 3g of boric acid, 10g N- (2-hydroxyethyl) ethylenediamine and 90g of cyclohexane into a reaction container, stirring, heating, removing water, reacting for 3h at 120 ℃, and finally filtering and evaporating the solvent and unreacted N- (2-hydroxyethyl) ethylenediamine to obtain the organic boron compound W-01.
An exemplary reaction is shown below, wherein R is H.
The product of example 2 was analyzed by infrared spectroscopy, the results of which are given in Table 1.
TABLE 1 Infrared analysis of the products
Table 1 shows that characteristic peaks such as C-OH stretching vibration peak, C-NH stretching vibration peak, benzene ring skeleton stretching vibration peak, N-C stretching vibration peak, O-C stretching vibration peak and B-O stretching vibration peak exist in the product, and the synthetic product can be shown to be a target compound.
Example 3
36g of t-butylated epoxy cardanol prepared in example 1, 10g of diethanolamine and 90g of toluene were added to a 250mL three-necked flask, heated with stirring, and reacted at 100 ℃ for 4 hours. And after the reaction is finished, carrying out reduced pressure distillation for 1h, removing the solvent and unreacted raw materials to obtain dark brown red viscous liquid tert-butyl amino cardanol, then adding 6g of boric acid, 20g of diethanolamine and 90g of cyclohexane into a reaction vessel, stirring, heating, removing moisture, reacting for 4h at 150 ℃, and finally filtering and steaming to remove the solvent and unreacted diethanolamine to prepare the organic boron compound W-02.
Example 4
21.5g of t-butylated epoxy cardanol prepared in example 1, 6g of diethylenetriamine and 90g of toluene were added to a 250mL three-necked flask, heated with stirring and reacted at 95 ℃ for 2 hours. And after the reaction is finished, carrying out reduced pressure distillation for 1h, removing the solvent and unreacted raw materials to obtain dark brown red viscous liquid tert-butyl amino cardanol, then adding 6g of boric acid, 8g of hexadecanol, 10.5g of diethylenetriamine and 90g of cyclohexane into a reaction vessel, stirring, heating, removing moisture, reacting for 5h at 145 ℃, and finally filtering and evaporating the solvent and unreacted diethylenetriamine to prepare the organic boron compound W-03.
Comparative example 1
36.3g of hexadecanol, 18.3g of ethanolamine, 6.2g of boric acid and 90g of toluene solvent were added to a reaction vessel, stirred, heated, reacted at 145 ℃ for 6 hours, and finally filtered and the solvent and unreacted ethanolamine were distilled off to obtain a comparative organoboron compound V-01.
Examples 5-7 and comparative examples 2-3 of lubricating oil compositions for air compressors
Examples 5-7 and comparative examples 2-3, air compressor lubricating oil compositions were prepared according to the formulation compositions of Table 2, wherein the main additives and lubricating base oil sources used were as follows:
antioxidant T501, a product of the institute of petrochemical institute, xinpu corporation, industrial products
Nitrogen-containing sulfur phosphoric acid derivative T305, shenyang Hua Lun lubricating oil additive Co., ltd, industrial products
Acrylic acid-ether copolymer T911, shenyang Polyxintian chemical Co., ltd, industrial products
Diisooctyl sebacate, beijing chemical industry, sanchu chemical industry, industrial products
TABLE 2 examples and comparative examples of lubricating oil compositions for air compressors
The lubricating oil compositions of the air compressors of the above examples and comparative examples are respectively subjected to the evaluation of the high-temperature oxidation resistance lubricating oil oxidation induction period, the measuring method is SH/T0719, the testing instrument is a TA5000 DSC instrument of the American TA company, and the testing conditions are as follows: 190 ℃, oxygen pressure of 0.5MPa and heating speed of 10 ℃/min.
The abrasion resistance of the lubricating oil was measured by the four-ball method SH/T0189 and by a four-ball tester model K93190, manufactured by Koehler, USA, under the conditions of 1200rpm,75 ℃,392N and 60min, for the lubricating oil compositions of the air compressors of the above examples and comparative examples, respectively.
The evaluation results of the high-temperature oxidation resistance and abrasion resistance are shown in table 3.
TABLE 3
| Sample (I) | Oxidative induction period/min | Abrasive grain diameter/mm |
| Example 5 | 19.8 | 0.52 |
| Example 6 | 18.5 | 0.58 |
| Example 7 | 17.6 | 0.63 |
| Comparative example 2 | 10.2 | 0.77 |
| Comparative example 3 | 14.7 | 0.70 |
Claims (10)
1. The air compressor lubricating oil composition comprises, by mass, 0.1-10% of an organoboron compound, 0.01-5% of an antioxidant, 0.01-5% of an extreme pressure antiwear agent, 0.001-1% of a defoaming agent and a main amount of ester lubricating base oil, wherein the organoboron compound has a structure shown in formula (I):
in formula (I), a repeating units L and b boron-containing groups are present, a is an integer between 1 and 10 (preferably an integer between 1 and 5), b is an integer between 1 and 5 (preferably an integer between 1 and 3), a L groups, which are the same or different from each other, are each independently selected from the group represented by formula (II);
in formula (II), HO is bonded to the benzene ring (HO is preferably located on the benzene ring R) 1 Meta to the chain); y R groups are bonded to the benzene ring; y is selected from integers between 0 and 4 (preferably between 1 and 3); r groups are each independently selectedFrom H and C 1-20 Straight or branched chain alkyl (preferably each independently selected from H and C) 1-4 Straight or branched alkyl, more preferably t-butyl); n is an integer of 1 to 10 (preferably an integer of 1 to 3); r 1 Each independently selected from the group consisting of a single bond and C 1-20 Straight or branched alkylene (preferably selected from single bond and C) 1-4 Linear or branched alkylene); r of n repeating units 2 Are the same or different from each other and are each independently selected from the group consisting of a single bond and C 1-20 Straight or branched alkylene (preferably each independently selected from the group consisting of single bond and C) 1-4 Linear or branched alkylene); r 3 Is selected from H and C 1-20 Straight or branched chain alkyl (preferably selected from H and C) 1-4 Straight or branched chain alkyl); the A groups in the n repeating units are the same or different from each other and are independently selected from the group consisting of a single bond, a,
A group of formula (III) and a group of formula (IV),
the R is 4 Each independently selected from H and C 1-20 Straight or branched alkyl (preferably selected from H and C) 1-4 Straight or branched chain alkyl);
m is an integer of 0 to 10 (preferably an integer of 1 to 5);
said R 5 Each independently selected from the group consisting of C having a valence of 3 1-20 Straight or branched chain alkyl (preferably each independently selected from 3 valent C 1-4 Straight or branched chain alkyl);
each G 2 Each group is independently selected from G present in L groups other than the L group in which it is present 4 Binding end of group bonding, C 1-10 Straight-chain or branched alkyl, -R 6 G 3 H; each G 3 Each independently selected from-OG 1 、C 1-10 Linear or branched alkyl, H (preferably each independently selected from-OG) 1 、C 1-4 Linear or branched alkyl, OH, H);
said R 6 The radicals being selected from C 1-20 Straight or branched alkylene (preferably each independently selected from C) 1-4 Linear or branched alkylene);
G 1 a group selected from the binding end bonded to the boron-containing group, H;
G 4 the radicals being selected from G present in the L groups other than the L group in which they are present 2 A binding end to which a group is bonded, H;
in the a L groups, at least one A group is selected from the group represented by the formula (III), and at least one G group is present 1 The group is selected from binding ends bonded to boron elements in the boron-containing group;
each A' group of the b boron-containing groups is independently selected from the group consisting of G, which is present in the L group 1 A bonding end bonded with the group, a group shown as a formula (V) and-OR ', wherein the R' group is H OR C 1-20 Straight or branched alkyl (preferably H or C) 1-4 Linear or branched alkyl);
in formula (V), m is an integer of 0 to 10 (preferably an integer of 1 to 5);
said R 0 Each independently selected from C 1-10 Straight or branched alkyl, -R 6 G 5 H (preferably each independently selected from C) 1-4 Straight or branched alkyl, -R 6 G 5 、H)；
R is as described 5 Each independently selected from the group consisting of C having a valence of 3 1-20 Straight or branched chain alkyl (preferably each independently selected from the group consisting of C having a valence of 3 1-4 Straight or branched chain alkyl);
G 6 the group is selected from-R 6 G 5 、C 1-4 Linear or branched alkyl, H;
r is as described 6 The radicals being selected from C 1-20 Straight or branched alkylene (preferably each independently)Is selected from C 1-4 Linear or branched alkylene);
each G 5 Each independently selected from-OG 1 、C 1-4 Linear or branched alkyl, OH, H, wherein G 1 A group selected from a binding end bonded to boron element in the boron-containing group, C 1-4 Linear or branched alkyl, H;
in the group of formula (V), there is at least one G 1 The group is selected from binding ends bonded to boron elements in the boron-containing group;
in b of said boron-containing groups, at least one A' group is present selected from the group consisting of G and L 1 A binding end to which a group is bonded;
each group in the organoboron compound complies with the bonding rule.
2. Lubricating oil composition according to claim 1, wherein the organoboron compound comprises one or more of the following structural compounds:
wherein the R group is H or C 1 -C 20 Linear or branched alkyl.
3. The lubricating oil composition according to claim 1, wherein the organoboron compound is prepared by a method comprising the steps of:
(1) Reacting a compound represented by formula (X) with a peroxide;
in formula (X), HO is bonded to the phenyl ring (HO is preferably located on the phenyl ring R) 1 Meta to the chain); y R groups are bonded to the benzene ring; y is selected from an integer between 0 and 4 (preferably an integer between 1 and 3); each R group is independently selected from H and C 1-20 Straight or branched chain alkyl (preferably each independently selected from H and C) 1-4 Straight or branched alkyl, more preferably selected from t-butyl); n is an integer of 1 to 10 (preferably an integer of 1 to 3); r is 1 Each independently selected from the group consisting of a single bond and C 1-20 Straight or branched alkylene (preferably selected from the group consisting of single bond and C) 1-4 Linear or branched alkylene); r of n repeating units 2 Are the same or different from each other and are each independently selected from the group consisting of a single bond and C 1-20 Straight or branched alkylene (preferably each independently selected from single bond and C) 1-4 Straight or branched chain alkylene); r is 3 Is selected from H and C 1-20 Straight or branched chain alkyl (preferably selected from H and C) 1-4 Straight or branched chain alkyl); a' in the n repeating units are the same or different from each other and are each independently selected from the group consisting of a single bond, a,
Wherein R is 4 Each independently selected from H and C 1-20 Straight or branched chain alkyl (preferably selected from H and C) 1-4 Straight or branched chain alkyl); in formula (X) at least one A' is present which is->
(2) Reacting the reaction product of step (1) with a compound of formula (Y);
in the formula (Y), m is an integer of 0 to 10 (preferably an integer of 1 to 5);
said R 0 ' the groups are each independently selected from C 1-10 Straight or branched alkyl, -R 6 OH and H (preferably independently selected from each other)From C 1-4 Straight or branched alkyl, -R 6 OH, H); said R 5 Each independently selected from the group consisting of C having a valence of 3 1-20 Straight or branched chain alkyl (preferably each independently selected from 3 valent C 1-4 Straight or branched chain alkyl); each G 5 ' the groups are each independently selected from C 1-4 Linear or branched alkyl, OH, H; said G 6 ' group is selected from C 1-10 Straight-chain or branched alkyl, -R 6 OH and H; said R 6 Each independently selected from C 1-20 Straight or branched alkylene (preferably each independently selected from C) 1-4 Linear or branched alkylene);
in formula (Y), there is at least one G 5 ' the group is selected from OH or at least one G 6 ' group or R 0 ' the group is selected from-R 6 OH, and at least one R is present 0 ' group or G 6 ' the group is H;
(3) And (3) reacting the reaction product obtained in the step (2) with an inorganic boron compound, and collecting the product.
4. The lubricating oil composition according to claim 3,
in the step (1), the compound represented by the formula (X) is selected from cardanol and alkylated cardanol; and/or the peroxide is selected from one or more of hydrogen peroxide, peroxyformic acid, peroxyacetic acid, peroxysulfonic acid, m-chloroperoxybenzoic acid, tert-butyl hydroperoxide, tert-butyl peroxyacetate, methyl ethyl ketone peroxide, dibenzoyl peroxide and cyclohexanone peroxide;
and/or, in the step (2), the compound shown in the formula (Y) is selected from one or more of fatty amine, polyenepolyamine, one or more hydroxyl-substituted fatty amine and one or more hydroxyl-substituted polyenepolyamine;
and/or, in step (3), the inorganic boron compound is selected from one or more of boric acid, boric oxide and a half ester of boric acid.
5. The lubricating oil composition according to claim 3, wherein the equivalent ratio of the compound represented by the formula (X) to the peroxide, the compound represented by the formula (Y), and the inorganic boron compound is 1:0.5 to 10:0.5 to 10:0.5 to 5 (preferably 1:2 to 3:2 to 3:1 to 2).
6. Lubricating oil composition according to claim 3, characterized in that the reaction temperature in step (1) is from 0 to 100 ℃ (preferably from 20 to 80 ℃); the reaction temperature of the step (2) is 50-150 ℃ (preferably 60-100 ℃); the reaction temperature in the step (3) is 80-200 ℃ (preferably 110-150 ℃).
7. Lubricating oil composition according to claim 3, characterized in that the reaction time of step (1) is from 1 to 10 hours (preferably from 3 to 5 hours); the reaction time of the step (2) is 1-10 h (preferably 2-4 h); the reaction time of the step (3) is 1 to 10 hours (preferably 3 to 5 hours).
8. Lubricating oil composition according to any one of claims 1 to 7, characterized in that the antioxidant is selected from phenolic antioxidants; the extreme pressure antiwear agent is selected from one or more of thiophosphoric acid nitrogenous derivatives, phosphate esters, phosphite esters, thiophosphoric acid amine salts, sulfurized olefins and dialkyl dithiocarbamate; the defoaming agent is selected from one or more of acrylic acid and ether copolymer, methyl silicone oil and ethyl silicone oil; the ester lubricating base oil is diester lubricating base oil.
9. The lubricating oil composition of any one of claims 1 to 7, wherein the air compressor lubricating oil composition comprises, in mass percent, 0.2% to 5% of an organoboron compound, 0.01% to 3% of an antioxidant, 0.01% to 3% of an extreme pressure antiwear agent, 0.001% to 0.5% of an antifoaming agent, and a major amount of an ester lubricating base oil.
10. The method of making the air compressor lubricating oil composition of any one of claims 1-9, comprising the step of mixing the additive and the lubricating base oil in the air compressor lubricating oil composition.
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Citations (7)
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| US20200361964A1 (en) * | 2019-05-17 | 2020-11-19 | Vanderbilt Chemicals, Llc | Less corrosive organoboron compounds as lubricant additives |
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2021
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| US4507216A (en) * | 1983-03-14 | 1985-03-26 | Mobil Oil Corporation | Hindered phenyl esters of cyclic borates and lubricants containing same |
| CN101597535A (en) * | 2009-06-30 | 2009-12-09 | 王严绪 | A kind of novel organic nitrogen-containing borate ester lubricating oil additive |
| CN105586135A (en) * | 2014-10-23 | 2016-05-18 | 中国石油化工股份有限公司 | Urea-based lubricating grease composition with excellent antifriction property and preparation method therefor |
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| CN110691838A (en) * | 2017-05-31 | 2020-01-14 | 道达尔销售服务公司 | Compounds comprising polyamine, acid and boron functional groups and their use as lubricant additives |
| CN111057108A (en) * | 2018-10-16 | 2020-04-24 | 中国石油化工股份有限公司 | Phosphoramidate compound and preparation method and application thereof |
| US20200361964A1 (en) * | 2019-05-17 | 2020-11-19 | Vanderbilt Chemicals, Llc | Less corrosive organoboron compounds as lubricant additives |
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