CN114478200A - Phenol derivative and preparation method and application thereof - Google Patents
Phenol derivative and preparation method and application thereof Download PDFInfo
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- CN114478200A CN114478200A CN202011168618.0A CN202011168618A CN114478200A CN 114478200 A CN114478200 A CN 114478200A CN 202011168618 A CN202011168618 A CN 202011168618A CN 114478200 A CN114478200 A CN 114478200A
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- 150000002989 phenols Chemical class 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title abstract description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 18
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 16
- 239000010687 lubricating oil Substances 0.000 claims abstract description 16
- 230000001050 lubricating effect Effects 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000002199 base oil Substances 0.000 claims description 11
- -1 ethylene- Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 239000011831 acidic ionic liquid Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 239000011973 solid acid Substances 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 2
- 230000000855 fungicidal effect Effects 0.000 claims 1
- 239000000417 fungicide Substances 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 6
- 239000000295 fuel oil Substances 0.000 abstract description 3
- 239000004033 plastic Substances 0.000 abstract description 3
- 229920003023 plastic Polymers 0.000 abstract description 3
- 239000005060 rubber Substances 0.000 abstract description 3
- 239000003899 bactericide agent Substances 0.000 abstract description 2
- 239000004519 grease Substances 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 44
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 239000007788 liquid Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002808 molecular sieve Substances 0.000 description 12
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical group [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 238000007254 oxidation reaction Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 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 description 10
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 description 10
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 description 10
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 description 10
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 230000003647 oxidation Effects 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000003828 vacuum filtration Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 244000226021 Anacardium occidentale Species 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 235000020226 cashew nut Nutrition 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 239000012488 sample solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101100407037 Oryza sativa subsp. japonica PAO6 gene Proteins 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-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 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-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
- 101100407030 Arabidopsis thaliana PAO2 gene Proteins 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 101150092791 PAO4 gene Proteins 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- GWBUAGAPOIBIRT-UHFFFAOYSA-G [F-].[Al+3].[Si+4].[F-].[F-].[F-].[F-].[F-].[F-] Chemical compound [F-].[Al+3].[Si+4].[F-].[F-].[F-].[F-].[F-].[F-] GWBUAGAPOIBIRT-UHFFFAOYSA-G 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical compound C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 0.000 description 1
- GPTJTTCOVDDHER-UHFFFAOYSA-N cyclononane Chemical compound C1CCCCCCCC1 GPTJTTCOVDDHER-UHFFFAOYSA-N 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring
- C07C39/19—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring containing carbon-to-carbon double bonds but no carbon-to-carbon triple bonds
-
- 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
- C10M129/88—Hydroxy compounds
- C10M129/91—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
Abstract
The invention provides a phenol derivative and a preparation method and application thereof. The structure of the phenolic derivative is shown as the general formula (I):
Description
Technical Field
The present invention relates to a phenol derivative, and more particularly to a phenol derivative suitable for use as a lubricant base oil.
Background
The oxidation stability refers to the high-temperature oxidation resistance and high-temperature deposition alleviation capability of the lubricating oil in the using process, and is an important embodiment of the high-temperature oxidation resistance of the lubricating oil. The lubricating oil has harsh working conditions and complex oxidation process. The oxidation reaction is closely related to the chemical composition of the lubricant base oil, the working environment, and the internal architecture of the engine. The oxidation stability of the base oil of the lubricating oil is poor, a series of chemical changes such as oxidation, polymerization, alkylation, decomposition and the like occur in a short period under the induction of high-temperature oxygen and the catalytic action of metals, so that the physicochemical properties and the color appearance of the engine oil are changed, such as increase of total acid value, increase of viscosity, deepening of color, low heat transfer efficiency, emulsification and foam generation, so that the service performance of the oil product is greatly reduced, and a large amount of generated oil sludge and other sediments are attached to metal accessories, so that piston ring sticking and equipment severe corrosion are caused, the abrasion of parts is increased, the working efficiency of mechanical equipment is reduced, the service life of the equipment is shortened, and even the normal working operation of the engine is seriously influenced. Improving the oxidation stability of the base oil of the lubricating oil has important significance for improving the working efficiency and the service life of lubricating system equipment.
The antioxidant is an essential additive in the processing industry of lubricating oil, fuel oil and plastic rubber, and has various types, mainly including phenol type, amine type, phenolic ester type, thioester type, phosphite ester type and the like. The hindered phenol antioxidant is widely applied due to the excellent antioxidation effect, but the hindered phenol antioxidant generally has the structure of 2, 6-di-tert-butyl-p-cresol (BHT), has certain toxicity and does not accord with the development trend of green and environment-friendly additives.
The cardanol is a main component of cashew nut shell liquid, is a natural phenolic compound, is an important agricultural and sideline product for cashew nut production, and is wide in source and huge in storage amount. Therefore, the asymmetric hindered phenol antioxidant is synthesized by adopting the abundant and low-cost natural compounds as raw materials, meets the definition of green chemistry and meets the strategic requirements of national sustainable development.
Disclosure of Invention
The invention provides a phenol derivative and a preparation method and application thereof.
The structure of the phenolic derivative is shown as the general formula (I):
in the general formula (I), R1、R2、R3、R4、R5Each independently selected from H, C1～C30A linear or branched alkyl group and a group of formula (II) (preferably each independently selected from H, C)1～C20Straight or branched alkyl and a group of formula (II), and R1、R2、R3、R4、R5At least one group of (a) is a group represented by the formula (II);
in the general formula (II), m is an integer between 1 and 10 (preferably an integer between 1 and 5);
each R is0' the groups are each independently selected from a single bond, C1-20Straight or branched alkylene (preferably selected from the group consisting of single bond and C)1-10Straight or branched alkylene, wherein R is terminal0' the radicals are preferably selected from C1～10Linear or branched alkylene groups of (a); r0The "group is selected from hydrogen, C1-20Straight or branched alkyl (preferably selected from hydrogen, C)1-10Straight or branched chain alkyl); m a 'groups are each independently selected from-CH ═ CH-, ethylene-, a group of formula (III), a group of formula (IV), and at least one a' group in formula (II) is selected from a group of formula (III) or a group of formula (IV);
in the group of formula (III) or the group of formula (IV), each R6Each independently selected from C1～30Is preferably selected from C, H1～20Is selected from the group consisting of H, and C1～10Straight or branched alkyl of (a), H); ar ring radical being C6～30Aryl (preferably C)6～20Aryl, more preferably C6～15Aryl, more preferably phenyl, naphthyl, anthracenyl); n is an integer of 0 to 20 (preferably an integer of 0 to 15, more preferably an integer of 0 to 10, and further preferably an integer of 0 to 6); n R groups are bonded to the Ar ring group; n R groups are each independently selected from C1～30Is preferably independently selected from C1～20More preferably each is independently selected from C1～10Straight or branched alkyl, H).
According to the invention, preferably, in the general formula (I), R1、R3、R5Each independently selected from H, C1～C4A linear or branched alkyl group; r2、R4Each independently selected from H, C1～C20A linear or branched alkyl group and a group of formula (II), wherein at least one group is a group of formula (II).
According to the invention, preferably, in the general formula (I), R1、R3、R5Each group is independently selected from H, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; r2、R4One of the groups is a group of formula (II) and the other is H.
According to the invention, the radical of formula (III) is preferably a radical of formula (V) or a radical of formula (VI),
wherein each group is as defined in any of the preceding aspects.
According to the invention, the radical of formula (IV) is preferably a radical of formula (VII) or a radical of formula (VIII),
wherein each group is as defined in any of the preceding aspects.
Examples of the phenol derivative of the present invention include:
the process for producing a phenol derivative of the present invention comprises the step of reacting a phenol compound represented by the general formula (X) with a compound represented by the general formula (Y);
in the general formula (X), R1”、R2”、R3”、R4”、R5The "groups, which are identical or different from each other, are each independently selected from H, C1～C20A linear or branched alkyl group and a group represented by the general formula (Z), wherein at least one group is selected from the group represented by the general formula (Z);
wherein R is1"' group is selected from single bond, C1-20Straight or branched alkylene (preferably selected from single bond and C)1-4Linear or branched alkylene); r in m repeating units2The "` groups, which may be identical or different from each other, are each independently selected from the group consisting of a single bond, C1-20Straight or branched alkylene (preferably each independently selected from single bond, C)1-4Linear or branched alkylene); r3"' group is selected from hydrogen, C1-20Straight or branched alkyl (preferably selected from hydrogen, C)1-4Straight or branched chain alkyl); r in m repeating units4The "` groups, which are identical or different from each other, are each independently selected from hydrogen, C1-20Straight or branched chain alkanesRadical (preferably each independently selected from hydrogen, C1-4Straight or branched chain alkyl); r in m repeating units5The "` groups, which are identical or different from each other, are each independently selected from hydrogen, C1-20Straight or branched chain alkyl (preferably each independently selected from hydrogen, C1-4Straight or branched chain alkyl); m is a positive integer (preferably a positive integer between 1 and 10, more preferably a positive integer between 1 and 3);
in the general formula (Y), Ar ring group is C6～30Aryl (preferably C)6～20Aryl, more preferably C6～15Aryl, more preferably phenyl, naphthyl, anthracenyl); n' is an integer of 0 to 20 (preferably an integer of 0 to 15, more preferably an integer of 0 to 10, and further preferably an integer of 0 to 6); n 'R' groups are bonded to the Ar ring group; n 'R' groups are each independently selected from C1～30Is preferably independently selected from C1～20More preferably each is independently selected from C1～10Straight or branched alkyl, H).
According to the preparation process of the present invention, in the general formula (X), preferably, the group R1”、R3”、R5"equal to or different from each other, each independently selected from hydrogen, C1-4A linear or branched alkyl group; radical R2”、R4"the same or different from each other, each independently selected from H, C1-20A linear or branched alkyl group and a group represented by the general formula (Z), wherein at least one group is selected from the group represented by the general formula (Z).
According to the preparation process of the present invention, in the general formula (X), further preferably, the group R1”、R3”、R5"equal to or different from each other, each independently selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; radical R2”、R4"one group is selected from the group represented by the general formula (Z) and the other group is selected from H.
The phenol compound represented by the general formula (X) of the present invention is preferably derived from a natural plant cashew nut, contains a large amount of cashew nut shell oil in the cashew nut shell, contains meta-phenol as a main component, is generally called cardanol, and has the following structure:
wherein R is C15H(31+x)And x is 0, -2, -4 or-6.
According to the production method of the present invention, the reaction equivalent ratio between the compound represented by the formula (X) and the compound represented by the formula (Y) is preferably 1: 1-6; more preferably 1: 1 to 3.
According to the preparation method of the invention, the temperature for reacting the compound represented by the formula (X) and the compound represented by the formula (Y) is preferably 60-200 ℃, and more preferably 90-180 ℃.
According to the preparation method of the present invention, the reaction time of the compound represented by the formula (X) and the compound represented by the formula (Y) is generally as long as possible, and is preferably 1 to 6 hours, and more preferably 2 to 4 hours.
According to the preparation process of the present invention, the compound represented by the formula (X) and the compound represented by the formula (Y) are optionally reacted in the presence of an inert gas, preferably nitrogen.
According to the preparation method of the present invention, a catalyst may or may not be added, preferably a catalyst is added in the reaction of the compound represented by the formula (X) and the compound represented by the formula (Y). The catalyst is preferably an acidic catalyst, and for example, a Lewis acid, a transition metal salt, a metal oxide,
One or more of acid, solid acid, acidic ionic liquid and supported catalyst thereof, wherein the supported catalyst carrier can be molecular sieve, alumina, zeolite, graphite, carbon black and resin. The acid catalyst can be one or more of aluminum trichloride, stannic chloride, boron trifluoride, sulfuric acid, hydrofluoric acid, phosphoric acid, Y-type molecular sieve, M-type molecular sieve, beta zeolite, mordenite, heteropoly acid, silicon aluminum fluoride and perfluoroalkanesulfonic acid and a supported catalyst thereof. The amount of the catalyst is preferably 1 to 10% by mass of the compound represented by the formula (X).
According to the preparation method of the present invention, a solvent may be added or may not be added, preferably a solvent is added in the reaction of the compound represented by the formula (X) and the compound represented by the formula (Y). The solvent is preferably a hydrocarbon solvent, preferably one or more of alkane, aromatic hydrocarbon and ether, more preferably an alkane solvent, and for example, one or more of hexane, heptane, octane, nonane, decane, undecane, dodecane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, benzene, toluene, xylene, ethylbenzene, propylbenzene, diethylether, propylether, isopropylether and butylether may be used. The amount of the solvent to be added is not particularly limited, as long as the reaction is promoted to proceed smoothly. The solvent may be removed by a known method, for example, distillation, rectification, etc., and is not particularly limited.
According to the preparation method of the invention, the reaction product is optionally washed and purified by using a solvent, and the solvent which can be washed is preferably a hydrocarbon solvent. The solvent may be removed by a conventional technique such as drying, evaporation, distillation, etc., and is not particularly limited.
The phenols prepared by the preparation method can be compounds with single structures or mixtures containing compounds with different structures. For a mixture of compounds of different structures, it is sometimes possible to separate it into compounds of a single structure, and it is sometimes also possible to use the mixture of compounds of different structures as it is without separating it into compounds of a single structure.
The phenol derivative has excellent antioxidant performance and bactericidal performance, can be used as an antioxidant and a bactericide, and can be applied to lubricating oil, lubricating grease, fuel oil and rubber plastics. The phenol derivative can react with amino, has the performance of deteriorating protein and has a bactericidal effect.
The invention also provides a lubricating oil composition which comprises the phenolic derivative or the phenolic derivative prepared by the method and lubricating oil base oil. Wherein the phenolic derivative accounts for 1-50%, preferably 3-40%, more preferably 5-30% of the total mass of the lubricating oil composition. The lubricant base oil may be one or more of API group I, II, III, IV and V lubricant base oils. The API I, II and III lubricating oil base oil can be selected from 100SN, 150SN, 200SN, 500SN, 650SN, 150BS, 100N, 150N, 200N, 500N, 600N, S2 and S6; the API IV lubricating oil base oil can be selected from PAO2, PAO4, PAO6, PAO8 and PAO 10; the API V lubricating oil base oil can be ester oil.
The lubricating oil composition has excellent oxidation resistance and bactericidal and bacteriostatic effects.
Detailed Description
The present invention is further illustrated but is not to be construed as limited by the following examples.
In the present specification, the term "single bond" is sometimes used in the definition of a group. By "single bond", it is meant that the group is absent. For example, assume the formula-CH2-A-CH3Wherein 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-CH2-CH3。
The main raw material sources used are as follows:
cardanol, Shanghai Bingshi Binghe chemical science & technology Limited, Industrial products
Refined naphthalene, chemical reagents of national drug group, Ltd, analytical purity
Aluminum trichloride, national pharmaceutical group chemical reagent Co., Ltd, analytical purity
Cyclohexane, national chemical group chemical reagent, Inc., analytical pure
Sodium hydroxide, national pharmaceutical group chemical reagents, Inc., analytical purity
1-methylnaphthalene, national pharmaceutical group chemical reagents, Ltd, analytical purity
Y-type molecular sieve, catalyst factory of southern Kai university, industrial products
Boron trifluoride etherate, analytical purity, Ikay technologies, Beijing
Trifluoromethanesulfonic acid, Beijing YinoKay science and technology Co., Ltd, analytically pure
Antioxidant T511, a institute of petrochemical institute, Xinpu corporation, Industrial products
Antioxidant T501, a product of the institute of petrochemical institute, Xinpu corporation, Industrial products
Mineral oil S6, China petrochemical lubricating oil Co., Ltd., Industrial products
PAO6, XUEFULONG (China) investment Limited, INDUSTRIAL PRODUCTS
Example 1
0.375mol of refined naphthalene, 0.75mol of cardanol and 50ml of cyclohexane were added to a 1-L round-bottom flask and heated to 70 ℃ with stirring. After naphthalene is completely dissolved, 3.46g of aluminum trichloride is added into the mixture, the mixture is continuously stirred and heated to 90 ℃, nitrogen is filled at the same time, the cyclohexane is kept to flow back well, the mixture reacts for 3 hours at 130 ℃, then the mixture is cooled to 50 ℃, the nitrogen protection is closed, and the solid catalyst in the mixture is removed by vacuum filtration to obtain dark brown oily liquid. Respectively carrying out alkali washing and water washing 3 times by using 0.1mol/L sodium hydroxide solution and deionized water, separating a water phase and an oil phase by using a separating funnel, standing for layering, removing the water phase, and reserving the oil phase to obtain colorless oily liquid. And distilling the reaction product under reduced pressure to remove the solvent and unreacted reaction raw materials in the reaction system. And after the reduced pressure distillation is finished, cooling the mixture under the protection of nitrogen to obtain a yellow brown oily liquid, namely the phenol derivative.
Example 2
0.375mol of refined naphthalene, 0.75mol of cardanol and 50ml of cyclohexane were added to a 1-L round-bottom flask and heated to 70 ℃ with stirring. After naphthalene is completely dissolved, adding 2.33g of trifluoromethanesulfonic acid into the mixture, continuing stirring and heating to 90 ℃, simultaneously introducing nitrogen, keeping cyclohexane in good reflux, reacting at 130 ℃ for 3 hours, then cooling to 50 ℃, closing nitrogen protection, and removing trifluoromethanesulfonic acid by vacuum filtration to obtain dark brown oily liquid. Respectively carrying out alkali washing and water washing 3 times by using 0.1mol/L sodium hydroxide solution and deionized water, separating a water phase and an oil phase by using a separating funnel, standing for layering, removing the water phase, and reserving the oil phase to obtain colorless oily liquid. And distilling the reaction product under reduced pressure to remove the solvent and unreacted reaction raw materials in the reaction system. And after the reduced pressure distillation is finished, cooling the mixture under the protection of nitrogen to obtain a yellow brown oily liquid, namely the phenol derivative.
Example 3
0.375mol of refined naphthalene, 0.75mol of cardanol and 50ml of cyclohexane were added to a 1-L round-bottom flask and heated to 70 ℃ with stirring. After naphthalene is completely dissolved, adding 2.33g of Y-type molecular sieve into the mixture, continuously stirring and heating to 90 ℃, simultaneously introducing nitrogen, keeping cyclohexane to be well refluxed, reacting for 3 hours at 150 ℃, then cooling to 50 ℃, closing nitrogen protection, and removing the molecular sieve catalyst by vacuum filtration to obtain dark brown oily liquid. And distilling the reaction product under reduced pressure to remove the solvent and unreacted reaction raw materials in the reaction system. And after the reduced pressure distillation is finished, cooling the mixture under the protection of nitrogen to obtain a yellow brown oily liquid, namely the phenol derivative.
Example 4
0.375mol of refined naphthalene, 0.75mol of cardanol and 50ml of cyclohexane were added to a 1-L round-bottom flask and heated to 70 ℃ with stirring. After naphthalene is completely dissolved, dropwise adding 2.5ml of boron trifluoride diethyl etherate into the mixture, continuously stirring and heating to 90 ℃, simultaneously introducing nitrogen, keeping cyclohexane in good reflux, reacting for 3 hours at 130 ℃, then cooling to 50 ℃, and closing the nitrogen protection to obtain colorless oily liquid. Respectively carrying out alkali washing and water washing 3 times by using 0.1mol/L sodium hydroxide solution and deionized water, separating a water phase and an oil phase by using a separating funnel, standing for layering, removing the water phase, and reserving the oil phase to obtain light yellow oily liquid. And distilling the reaction product under reduced pressure to remove the solvent and unreacted reaction raw materials in the reaction system. And after the reduced pressure distillation is finished, cooling the mixture under the protection of nitrogen to obtain a yellow brown oily liquid, namely the phenol derivative.
Example 5
A1L round bottom flask was charged with 0.375mol of 1-methylnaphthalene, 0.75mol of cardanol and 50ml of cyclohexane, and heated to 70 ℃ with stirring. After naphthalene is completely dissolved, 2.33g of Y-type molecular sieve is added into the mixture, the mixture is continuously stirred and heated to 90 ℃, nitrogen is filled at the same time, the cyclohexane is kept to flow back well, the mixture reacts for 3 hours at 180 ℃, then the mixture is cooled to 50 ℃, the nitrogen protection is closed, and the molecular sieve catalyst in the mixture is removed through vacuum filtration to obtain dark brown oily liquid. And distilling the reaction product under reduced pressure to remove the solvent and unreacted reaction raw materials in the reaction system. And after the reduced pressure distillation is finished, cooling the mixture under the protection of nitrogen to obtain a yellow brown oily liquid, namely the phenol derivative.
Example 6
0.375mol of refined naphthalene, 0.75mol of cardanol and 50ml of cyclohexane were added to a 1-L round-bottom flask and heated to 70 ℃ with stirring. After naphthalene is completely dissolved, 2.33g of Y-type molecular sieve is added into the mixture, the mixture is continuously stirred and heated to 90 ℃, nitrogen is filled at the same time, the cyclohexane is kept to flow back well, the mixture reacts for 3 hours at 180 ℃, then the mixture is cooled to 50 ℃, the nitrogen protection is closed, and the molecular sieve catalyst in the mixture is removed through vacuum filtration to obtain dark brown oily liquid. And distilling the reaction product under reduced pressure to remove the solvent and unreacted reaction raw materials in the reaction system. And after the reduced pressure distillation is finished, cooling the mixture under the protection of nitrogen to obtain a yellow brown oily liquid, namely the phenol derivative.
Example 7
0.375mol of refined naphthalene, 0.75mol of cardanol and 50ml of cyclohexane were added to a 1-L round-bottom flask and heated to 70 ℃ with stirring. And after naphthalene is completely dissolved, adding 2.33g of Y-type molecular sieve into the mixture, continuously stirring and heating to 90 ℃, simultaneously introducing nitrogen, keeping cyclohexane to flow well, reacting for 1 hour at 150 ℃, then cooling to 50 ℃, closing the nitrogen protection, and performing vacuum filtration to remove the molecular sieve catalyst to obtain dark brown oily liquid. And distilling the reaction product under reduced pressure to remove the solvent and unreacted reaction raw materials in the reaction system. And after the reduced pressure distillation is finished, cooling the mixture under the protection of nitrogen to obtain a yellow brown oily liquid, namely the phenol derivative.
Example 8
Respectively dissolving the phenolic derivative and the comparative hindered phenol antioxidants (T501 and T511) as additives to be evaluated into mineral oil S6 to prepare sample solutions 1-4 with the concentration of 0.5% (m/m), respectively carrying out antioxidant performance tests on the sample solutions, wherein the test results are shown in Table 1, the test instrument is a TA5000 DSC instrument of the American TA company, and the test conditions are as follows: 210 ℃, the oxygen pressure of 0.5MPa and the heating speed of 10 ℃/min.
TABLE 1
The comparison shows that the phenolic derivative of the invention obviously improves the oxidation induction period, is superior to the conventional hindered phenol antioxidant and is an excellent antioxidant.
Example 9
Respectively dissolving the phenolic derivative and the comparative hindered phenol antioxidants (T501 and T511) as additives to be evaluated into PAO6 to prepare sample solutions 5-8 with the concentration of 0.5% (m/m), respectively carrying out antioxidant performance tests on the sample solutions, wherein the test results are shown in Table 2, the test instrument is a TA5000 DSC instrument of the American TA company, and the test conditions are as follows: 210 ℃, the oxygen pressure of 0.5MPa and the heating speed of 10 ℃/min.
TABLE 2
The comparison shows that the phenolic derivative provided by the invention has the advantages that the oxidation induction period is obviously prolonged, the antioxidant performance is far better than that of the conventional hindered phenol antioxidant, and the sensitivity in synthetic oil is very excellent, so that the phenolic derivative is an excellent antioxidant.
Claims (13)
1. A phenol derivative has a structure shown in a general formula (I):
in the general formula (I), R1、R2、R3、R4、R5Each independently selected from H, C1～C30Straight chainOr a branched alkyl group and a group of formula (II) (preferably each independently selected from H, C1～C20Straight or branched alkyl and a group of formula (II), and R1、R2、R3、R4、R5At least one group of (a) is a group represented by the formula (II);
in the general formula (II), m is an integer between 1 and 10 (preferably an integer between 1 and 5);
each R is0' the groups are each independently selected from a single bond, C1-20Straight or branched alkylene (preferably selected from single bond and C)1-10Straight or branched alkylene, wherein R is terminal0' the radicals are preferably selected from C1～10Linear or branched alkylene groups of (a); r0The "group is selected from hydrogen, C1-20Straight or branched alkyl (preferably selected from hydrogen, C)1-10Straight or branched chain alkyl); m a 'groups are each independently selected from-CH ═ CH-, ethylene-, a group of formula (III), a group of formula (IV), and at least one a' group in formula (II) is selected from a group of formula (III) or a group of formula (IV);
in the group of formula (III) or the group of formula (IV), each R6Each independently selected from C1～30Is preferably selected from C, H1～20Is selected from the group consisting of H, and C1～10Straight or branched alkyl of (a), H); ar ring radical being C6～30Aryl (preferably C)6～20Aryl, more preferably C6～15Aryl, more preferably phenyl, naphthyl, anthracenyl); n is an integer of 0 to 20 (preferably an integer of 0 to 15, more preferably an integer of 0 to 10, and further preferably an integer of 0 to 6); n R groups with said Ar is a ring group bond; n R groups are each independently selected from C1～30Is preferably independently selected from C1～20More preferably each is independently selected from C1～10Straight or branched alkyl, H).
2. A phenolic derivative according to claim 1, characterized in that in formula (I), R is1、R3、R5Each independently selected from H, C1～C4A linear or branched alkyl group; r is2、R4Each independently selected from H, C1～C20A linear or branched alkyl group and a group of formula (II), wherein at least one group is a group of formula (II).
3. A phenolic derivative according to claim 1, characterized in that in formula (I), R is1、R3、R5Each group is independently selected from H, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; r2、R4One of the groups is a group of formula (II) and the other is H.
4. A phenol derivative according to claim 1, wherein the group of formula (III) is a group of formula (V) or a group of formula (VI),
and/or the group of formula (IV) is a group of formula (VII) or a group of formula (VIII),
5. a phenolic derivative according to claim 1, characterised in that said phenolic derivative is selected from the following specific compounds or mixtures thereof in any proportion:
6. a process for producing a phenol derivative, comprising the step of reacting a phenol compound represented by the general formula (X) with a compound represented by the general formula (Y);
in the general formula (X), R1”、R2”、R3”、R4”、R5The "groups, which are identical or different from each other, are each independently selected from H, C1～C20A linear or branched alkyl group and a group represented by the general formula (Z), wherein at least one group is selected from the group represented by the general formula (Z);
wherein R is1"' group is selected from single bond, C1-20Straight or branched alkylene (preferably selected from single bond and C)1-4Linear or branched alkylene); r in m repeating units2The "` groups, which may be identical or different from each other, are each independently selected from the group consisting of a single bond, C1-20Straight or branched alkylene (preferably each independently selected from single bond, C)1-4Linear or branched alkylene); r3"' group is selected from hydrogen, C1-20Straight or branched alkyl (preferably selected from hydrogen, C)1-4Straight or branched chain alkyl); r in m repeating units4The "` groups, which are identical or different from each other, are each independently selected from hydrogen, C1-20Straight or branched chain alkyl (preferably each independently selected from hydrogen, C1-4Straight or branched chain alkyl); r in m repeating units5The "` groups, which are identical or different from each other, are each independently selected from hydrogen, C1-20Straight or branched chain alkyl (preferably each independently selected from hydrogen, C1-4Straight or branched chain alkyl); m is a positive integer (preferably a positive integer between 1 and 10, more preferably a positive integer between 1 and 3);
in the general formula (Y), Ar ring group is C6～30Aryl (preferably C)6～20Aryl, more preferably C6～15Aryl, more preferably phenyl, naphthyl, anthracenyl); n' is an integer of 0 to 20 (preferably an integer of 0 to 15, more preferably an integer of 0 to 10, and further preferably an integer of 0 to 6); n 'R' groups are bonded to the Ar ring group; n 'R' groups are each independently selected from C1～30Is preferably independently selected from C1～20More preferably each is independently selected from C1～10Straight or branched alkyl, H).
7. The process according to claim 6, wherein in the formula (X), the group R1”、R3”、R5"equal to or different from each other, each independently selected from hydrogen, C1-4A linear or branched alkyl group; radical R2”、R4"the same or different from each other, each independently selected from H, C1-20A linear or branched alkyl group and a group represented by the general formula (Z), wherein at least one group is selected from the group represented by the general formula (Z).
8. The process according to claim 7, wherein in the formula (X), the group R1”、R3”、R5"equal to or different from each other, each independently selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; radical R2”、R4"one group is selected from the group represented by the general formula (Z) and the other groupThe group is selected from H.
9. The process according to claim 6, wherein the reaction equivalent ratio between the compound represented by the formula (X) and the compound represented by the formula (Y) is 1: 1-6 (preferably 1: 1-3), and the reaction temperature is 60-200 ℃ (preferably 90-180 ℃).
10. The process according to claim 6, wherein the compound represented by the formula (X) is reacted with the compound represented by the formula (Y) in the presence of an inert gas.
11. The process according to claim 6, wherein a catalyst (preferably an acidic catalyst, more preferably a Lewis acid, a salt of a compound having a transition metal salt of a metal salt of,
One or more of an acid, a solid acid, an acidic ionic liquid, and a supported catalyst thereof).
12. Use of the phenolic derivative according to any one of claims 1 to 5 or the phenolic derivative obtained by the process according to any one of claims 6 to 11 as an antioxidant or as a fungicide.
13. A lubricating oil composition comprising the phenol derivative according to any one of claims 1 to 5 or the phenol derivative obtained by the method according to any one of claims 6 to 11 and a lubricating base oil.
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