CN114507138A - Ester compound and preparation method and application thereof - Google Patents
Ester compound and preparation method and application thereof Download PDFInfo
- Publication number
- CN114507138A CN114507138A CN202011167141.4A CN202011167141A CN114507138A CN 114507138 A CN114507138 A CN 114507138A CN 202011167141 A CN202011167141 A CN 202011167141A CN 114507138 A CN114507138 A CN 114507138A
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- -1 Ester compound Chemical class 0.000 title claims abstract description 52
- 238000002360 preparation method Methods 0.000 title abstract description 14
- 239000002199 base oil Substances 0.000 claims abstract description 28
- 239000010687 lubricating oil Substances 0.000 claims abstract description 22
- 230000001050 lubricating effect Effects 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 44
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 22
- 239000002808 molecular sieve Substances 0.000 claims description 16
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 claims description 2
- XJMGDZBZBKBSLJ-GAXCVXDLSA-N (2e,4e,6e,8e)-deca-2,4,6,8-tetraenoic acid Chemical compound C\C=C\C=C\C=C\C=C\C(O)=O XJMGDZBZBKBSLJ-GAXCVXDLSA-N 0.000 claims description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- ZMXIYERNXPIYFR-UHFFFAOYSA-N 1-ethylnaphthalene Chemical compound C1=CC=C2C(CC)=CC=CC2=C1 ZMXIYERNXPIYFR-UHFFFAOYSA-N 0.000 claims description 2
- HMAMGXMFMCAOPV-UHFFFAOYSA-N 1-propylnaphthalene Chemical compound C1=CC=C2C(CCC)=CC=CC2=C1 HMAMGXMFMCAOPV-UHFFFAOYSA-N 0.000 claims description 2
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 claims description 2
- TVYVQNHYIHAJTD-UHFFFAOYSA-N 2-propan-2-ylnaphthalene Chemical compound C1=CC=CC2=CC(C(C)C)=CC=C21 TVYVQNHYIHAJTD-UHFFFAOYSA-N 0.000 claims description 2
- WXBXVVIUZANZAU-UHFFFAOYSA-N 2E-decenoic acid Natural products CCCCCCCC=CC(O)=O WXBXVVIUZANZAU-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- GZZPOFFXKUVNSW-UHFFFAOYSA-N Dodecenoic acid Natural products OC(=O)CCCCCCCCCC=C GZZPOFFXKUVNSW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 2
- 229910021536 Zeolite Inorganic materials 0.000 claims description 2
- 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 claims description 2
- 239000011831 acidic ionic liquid Substances 0.000 claims description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- RJTJVVYSTUQWNI-UHFFFAOYSA-N beta-ethyl naphthalene Natural products C1=CC=CC2=CC(CC)=CC=C21 RJTJVVYSTUQWNI-UHFFFAOYSA-N 0.000 claims description 2
- 239000006229 carbon black Substances 0.000 claims description 2
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims description 2
- 229940108623 eicosenoic acid Drugs 0.000 claims description 2
- BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 229960002969 oleic acid Drugs 0.000 claims description 2
- 235000021313 oleic acid Nutrition 0.000 claims description 2
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- NNNVXFKZMRGJPM-KHPPLWFESA-N sapienic acid Chemical compound CCCCCCCCC\C=C/CCCCC(O)=O NNNVXFKZMRGJPM-KHPPLWFESA-N 0.000 claims description 2
- 239000011973 solid acid Substances 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
- WXBXVVIUZANZAU-CMDGGOBGSA-N trans-2-decenoic acid Chemical compound CCCCCCC\C=C\C(O)=O WXBXVVIUZANZAU-CMDGGOBGSA-N 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 abstract description 27
- 230000003647 oxidation Effects 0.000 abstract description 26
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 39
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 239000007788 liquid Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 239000003921 oil Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- 239000002480 mineral oil Substances 0.000 description 9
- 235000010446 mineral oil Nutrition 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- KISVAASFGZJBCY-UHFFFAOYSA-N methyl undecenate Chemical compound COC(=O)CCCCCCCCC=C KISVAASFGZJBCY-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 7
- 238000005804 alkylation reaction Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000003828 vacuum filtration Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 5
- 239000002608 ionic liquid Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001336 alkenes Chemical class 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
- 238000005516 engineering process Methods 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-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
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 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
- 229940069096 dodecene Drugs 0.000 description 2
- 239000010696 ester oil Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- IJAFYYIBMJSQLI-UHFFFAOYSA-N 1-hexadecylnaphthalene Chemical compound C1=CC=C2C(CCCCCCCCCCCCCCCC)=CC=CC2=C1 IJAFYYIBMJSQLI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 238000005299 abrasion Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- CSDREXVUYHZDNP-UHFFFAOYSA-N alumanylidynesilicon Chemical compound [Al].[Si] CSDREXVUYHZDNP-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 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
- 229910052906 cristobalite Inorganic materials 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
- 230000007812 deficiency Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000007613 environmental effect Effects 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
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 230000006872 improvement Effects 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 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
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
-
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/34—Esters of monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/284—Esters of aromatic monocarboxylic acids
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides an ester compound and a preparation method and application thereof. The structure of the ester compound is shown as the formula (I):
Description
Technical Field
The present invention relates to the field of lubricant products, and in particular to ester compounds suitable for use as lubricating base oils.
Background
With the development of engine and other mechanical equipment technologies, the use conditions of lubricating oil are increasingly harsh, the lubricating oil industry faces serious challenges of quality upgrading, economic benefits and environmental regulations, and high-quality lubricating oil base oil with excellent thermal oxidation stability, hydrolytic stability, high viscosity index and low volatility is urgently required to be produced. The market demand has driven the research on high quality base oils, wherein synthetic or semi-synthetic oils, with their excellent and unique properties, have made up for the deficiencies in mineral oil properties in many fields and are increasingly used more widely.
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 alkyl aromatic base oil is a high-performance base oil or a base oil blending component, has more excellent thermal oxidation stability and good additive solubility compared with mineral oil, PAO oil and ester oil, can be compatible with various sealing materials, and effectively provides a technical means for blending high-performance lubricating oil. The use of alkyl aromatic base oils as blendstocks can exhibit better performance properties than ester oil/PAO oil blended lubricants. Moreover, the blending of alkyl aromatic base oil into mineral oil can significantly increase the service temperature of mineral oil, and the use of alkyl aromatic base oil components in some foreign high-grade lubricating oils has been reported. Therefore, the alkyl aromatic base oil is valued by a plurality of big foreign companies, and the product production technology has high requirements and few published documents, so that the alkyl aromatic base oil becomes a high-added-value product monopolized by the big foreign companies, and the domestic blank is still a blank in this respect at present. Therefore, the alkyl aromatic base oil has very good development and application prospects, particularly has the characteristic of excellent thermo-oxidative stability of the alkyl aromatic base oil in some high-temperature aerobic working environments, and can also be used for producing special industrial oil, such as carbon dioxide refrigerator oil and the like.
The excellent oxidation stability of alkyl aromatic base oils depends mainly on the aromatic rings in the molecular structure. Therefore, the oxidation stability of the lubricating oil is effectively improved, the aryl base oil component with good oxidation stability and excellent other physical and chemical properties can be adopted, the generation of oxidation products can be effectively reduced, and the oxidation stability is improved.
US 4035308 discloses the use of AlCl subjected to anhydrous treatment3The monosubstituted alkyl aromatic hydrocarbon is synthesized and used as a blending component of the lubricating oil.
US 4148834 discloses a lubricant base oil component having as a major component a disubstituted long chain alkyl aromatic hydrocarbon. The component is prepared by a two-step alkylation method, wherein in the first step of alkylation, HF is used as a catalyst to catalyze the alkylation reaction of aromatic hydrocarbon and long-chain alpha-olefin, and in the second step, AlCl is used3Or AlBr3Instead of HF as catalyst.
US 5254766 discloses the synthesis of long chain alkyl naphthalenes and their derivatives using heteropolyacids (phosphotungstic or silicotungstic acids) as catalysts.
US 6596662 discloses the preparation of hexadecyl naphthalene (olefin conversion: 92.4%, wherein monoalkyl naphthalene accounts for 85.8%, dialkyl naphthalene accounts for 6.6%), hexadecyl diphenyl sulfide (olefin conversion 84.8%, wherein monoalkyl substituent accounts for 79.7%, dialkyl substituent accounts for 5.1%), hexadecyl diphenyl ether (olefin conversion 91.5%, wherein monoalkyl diphenyl ether accounts for 88.8%, dialkyl diphenyl ether accounts for 2.7%) using a dealuminated USY molecular sieve (silicon-aluminum atomic ratio 6.5-10, aluminum content outside the framework < 25%).
CN 1225617a discloses that an amine ionic liquid is used to catalyze the alkylation reaction of benzene and dodecene at room temperature, the selectivity of the reaction is 87%, the conversion rate of dodecene is more than 98%, and compared with the product obtained by the commonly used HF method, the product obtained by using the ionic liquid has better distribution of isomers and more 2-position substitution products.
WO99/03163 discloses the passing of ionic liquids through impregnationMethod for immobilizing on porous polymer and SiO2The novel alkylation catalyst is prepared from materials such as powder, porous alumina, molecular sieve, clay and the like, and has the advantages of high catalytic activity, high reaction speed and high 2-alkylbenzene content. Compared with the single use of the ionic liquid catalyst, the catalyst has improved stability, and the recycling frequency is greatly higher than that of the ionic liquid catalyst.
Despite the better oxidation stability of the existing alkyl aromatic base oils, there is still much room for improvement. There remains a need in the art for alkyl aromatic base oils that have superior properties.
Disclosure of Invention
The invention provides an ester compound and a preparation method and application thereof.
The structure of the ester compound is shown as the formula (I):
in the formula (I), Ar ring group is C6～20Aryl (preferably C)6～15Aryl, more preferably C6～10Aryl, more preferably phenyl, naphthyl, anthracenyl);
n is an integer of 1 to 20 (preferably an integer of 1 to 15, more preferably an integer of 1 to 10, and further preferably an integer of 1 to 6);
n R groups are bonded to the Ar ring group;
n R groups are each independently selected from the group of formula (II), C1～30Is preferably independently selected from the group represented by the formula (II), C1～20More preferably, each of the straight-chain or branched alkyl groups and H is independently selected from the group represented by the formula (II), C1～10H) and at least one R group is selected from the group represented by formula (II);
in the formula (II), m is an integer of 1 to 10 (preferably an integer of 1 to 5, more preferably 1, 2 or 3); r1The radicals being selected from C1～30Is preferably selected from C1～20More preferably selected from C1～10Straight or branched alkyl groups of (ii); m R2Each independently selected from C1～30Alkylene group of (2), a single bond (preferably selected from C)1～20Is more preferably selected from C1～10Linear or branched alkylene, single bond, with
Bonded R2The radicals are preferably selected from C1～10Linear or branched alkylene groups of (a); r3The radicals being 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);
m a 'groups are each independently selected from-CH ═ CH-, ethylene-, a group represented by formula (III), a group represented by formula (IV), a group represented by formula (V) and a group represented by formula (VI), and at least one a' group present in formula (II) is selected from a group represented by formula (III) or a group represented by formula (IV), the group represented by formula (III) or formula (IV) is bonded to the Ar ring group in formula (I), and represents a bonding end at which the group represented by formula (III) or formula (IV) is bonded to the Ar ring group in formula (I);
in the group represented by the formula (III), the group represented by the formula (IV), the group represented by the formula (V) and the group represented by the formula (VI), each R4Each 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 C6～20Aryl (preferably C)6～15Aryl, more preferably C6～10Aryl, more preferably phenyl, naphthyl, anthryl)。
The ester compound of the invention comprises one compound or a plurality of compounds mixed in any proportion as follows:
the invention also provides a preparation method of the ester compound, which comprises the step of reacting the compound shown in the formula (alpha) with the compound shown in the formula (beta),
in the formula (. alpha.), m is an integer of 1 to 10 (preferably an integer of 1 to 5, more preferably 1, 2 or 3); r is1The radicals being selected from C1～30Is preferably selected from C1～20More preferably selected from C1～10Straight or branched alkyl groups of (ii); m R2Each independently selected from C1～30Alkylene group of (2), a single bond (preferably selected from C)1～20Is more preferably selected from C1～10A straight or branched alkylene group of (A), a single bond, and
bonded R2The radicals are preferably selected from C1～10Linear or branched alkylene groups of (a); r3The radicals being selected from C1～30A hydrocarbon group of (C), H (preferably selected from C)1～20Is selected from the group consisting of H, and C1～10Straight or branched alkyl of (a), H);
in the formula (. beta.), Ar ring group is C6～20Aryl (preferably C)6～15Aryl, more preferably C6～10Aryl, more preferably phenyl, naphthyl, anthracenyl); n' is an integer of 1 to 19 (preferably an integer of 1 to 14, more preferably an integer of 1 to 9, and further preferably an integer of 1 to 5);
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 method of the present invention, the compound represented by the formula (α) may be one or more selected from the following compounds: octenoic acid, decenoic acid, undecenoic acid, dodecenoic acid, decatetraenoic acid, hexadecenoic acid, oleic acid, linoleic acid, linolenic acid, and eicosenoic acid.
According to the preparation method of the present invention, the compound represented by the formula (β) may be one or more selected from the following compounds: benzene, naphthalene, anthracene, methylnaphthalene, ethylnaphthalene, n-propylnaphthalene, 2-isopropylnaphthalene.
According to the production method of the present invention, the mass ratio between the compound represented by the formula (α) and the compound represented by the formula (β) is preferably 1: 0.1 to 1; more preferably 1: 0.2 to 1.
According to the preparation method of the present invention, the temperature for reacting the compound represented by the formula (α) with the compound represented by the formula (β) is preferably 60 to 200 ℃, more preferably 90 to 180 ℃.
According to the preparation method of the present invention, the reaction time of the compound represented by the formula (α) and the compound represented by the formula (β) is generally as long as possible, and is preferably 1 to 8 hours, and more preferably 3 to 6 hours.
According to the production method of the present invention, preferably, the compound represented by the formula (α) is reacted with the compound represented by the formula (β) in the presence of an inert gas, preferably nitrogen.
According to the preparation method of the present invention, a catalyst may be added or not added, preferably a catalyst is added in the reaction of the compound represented by the formula (α) and the compound represented by the formula (β). 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 can be a carrierAs molecular sieve, alumina, zeolite, graphite, carbon black, 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, phosphotungstic acid, silicon aluminum fluoride and perfluoroalkanesulfonic acid and a supported catalyst thereof. The amount of the catalyst is preferably 1% to 10% of the amount of the compound represented by the formula (α).
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 (α) and the compound represented by the formula (β). 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, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, benzene, toluene, xylene, ethylbenzene, propylbenzene, diethyl ether, propyl ether, isopropyl ether and dibutyl ether 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, or the like, 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 ester compound prepared by the preparation method can be a compound with a single structure or a mixture 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 product obtained by the production method of the present invention may contain, in addition to the ester compound, an unreacted compound represented by the formula (α) and/or a compound represented by the formula (β), and sometimes, for economic reasons, the unreacted compound represented by the formula (α) and/or the compound represented by the formula (β) are not separated from the product, but a mixture thereof is directly used as a product.
The ester compound can obviously improve the oxidation stability of lubricating oil (especially synthetic lubricating oil), and is suitable for being used as lubricating base oil.
The invention also provides a lubricating oil composition which comprises the ester compound or the ester compound prepared by the method and a lubricating oil additive. Wherein the ester compound accounts for 10-99%, preferably 30-95%, more preferably 50-90% of the total mass of the lubricating oil composition. Examples of the lubricating oil additive include various additives that are allowed to be added to a lubricating oil composition in the art, and specific examples thereof include an antioxidant, a detergent, a dispersant, a pour point depressant, a viscosity index improver, a friction modifier, an extreme pressure agent, an antiwear agent, and an antifoaming agent. The kind and amount of these additives are well known to those skilled in the art and will not be described herein. These additives may be used singly or in combination in any ratio.
The lubricating oil composition of the present invention has excellent oxidation stability.
Detailed Description
In the context of 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 present invention will be further illustrated in detail by the following examples and comparative examples, but the present invention is not limited thereto.
The main raw materials used are from the following sources:
10-undecylenic acid methyl ester, Iknoka science and technology Co., Ltd, Beijing, analytical purity
Refined naphthalene, national chemical group chemical reagent Limited, analytical pure
Aluminum trichloride, national pharmaceutical group chemical reagent Co., Ltd, analytical purity
N-heptane, national chemical group chemical reagent Limited, 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
Alkylnaphthalenes, Shanghai Nake science and technology Co., Ltd, Industrial products
T501, department of petrochemical industry, institute of research, Xinpu corporation, Industrial products
T511, department of petrochemical industry, institute of research, Xinpu corporation, Industrial products
Mineral oil S6, China petrochemical lubricating oil Co., Ltd., Industrial products
Example 1
A1L round-bottom flask was charged with 0.375mol of refined naphthalene, 0.75mol of methyl 10-undecenoate and 50ml of n-heptane, and the mixture was heated to 70 ℃ with stirring. After naphthalene was completely dissolved, 3.46g of aluminum trichloride was added to the mixture, and stirring and heating were continued to 90 ℃ while introducing nitrogen gas, and reaction was carried out at 130 ℃ for 3 hours while maintaining good reflux of n-heptane. And when the reaction liquid is cooled to about 50 ℃, closing the nitrogen protection, and removing the solid catalyst 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. The reaction product was distilled under reduced pressure to remove n-heptane and unreacted reaction materials in the reaction system. After the reduced pressure distillation is finished, brown oily liquid with certain viscosity is prepared, namely the ester compound of the invention, and the theoretical structure of the ester compound is shown as the following formula:
the element composition is C22H30O2The theoretical proportion (%) of each element is: c, 80.98; h, 9.20; o, 9.82; the elemental analysis of the obtained ester compound showed that (percent): c, 81.04; h, 9.11; o: 9.85. it can be seen that the structural analysis of the obtained ester compound is accurate.
Example 2
In a 1L round-bottom flask were added 0.375mol of refined naphthalene, 0.75mol of methyl 10-undecenoate and 50ml of n-heptane and the mixture was 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, good reflux of n-heptane is kept, and the reaction is carried out for 3 hours at 150 ℃. And when the reaction liquid is cooled to about 50 ℃, closing the nitrogen protection, and removing the solid catalyst by vacuum filtration to obtain dark brown oily liquid. The reaction product was distilled under reduced pressure to remove n-heptane and unreacted reaction materials in the reaction system. After the reduced pressure distillation is finished, brown oily liquid with certain viscosity is prepared, namely the ester compound of the invention.
Example 3
A1L round-bottom flask was charged with 0.375mol of refined naphthalene, 0.75mol of methyl 10-undecenoate and 50ml of n-heptane, 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 n-heptane well refluxing, 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. After the reduced pressure distillation is finished, cooling is carried out under the protection of nitrogen, and a tawny oily liquid, namely the ester compound is obtained.
Example 4
A1L round-bottomed flask was charged with 0.375mol of refined naphthalene, 0.75mol of methyl 10-undecenoate and 50ml of n-heptane 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 n-heptane to be 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. After the reduced pressure distillation is finished, cooling is carried out under the protection of nitrogen, and a tawny oily liquid, namely the ester compound is obtained.
Example 5
A1L round-bottom flask was charged with 0.375mol of 1-methylnaphthalene, 0.75mol of methyl 10-undecenoate and 50ml of n-heptane, 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 n-heptane 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. After the reduced pressure distillation is finished, cooling is carried out under the protection of nitrogen, and a tawny oily liquid, namely the ester compound is obtained.
Example 6
A1L round-bottom flask was charged with 0.375mol of refined naphthalene, 0.75mol of methyl 10-undecenoate and 50ml of n-heptane, 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 n-heptane to be in good reflux, reacting for 3 hours at 180 ℃, 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 reduced pressure distillation, cooling under the protection of nitrogen to obtain a brown oily liquid, namely the ester compound.
Example 7
A1L round-bottomed flask was charged with 0.375mol of refined naphthalene, 0.75mol of methyl 10-undecenoate and 50ml of n-heptane 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 n-heptane to be well refluxed, reacting for 1 hour 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. After the reduced pressure distillation is finished, cooling is carried out under the protection of nitrogen, and a tawny oily liquid, namely the ester compound is obtained.
Example 8
Adding an additive T501 into the ester compound of example 1, the ester compound of example 5, alkyl naphthalene and mineral oil S6 respectively to prepare uniform solutions with the mass concentration of T501 of 0.5%, and performing DSC oxidation resistance tests on the solution samples respectively, wherein the test results are shown in Table 1, the test instruments are TA5000 DSC instruments of the American TA company, and the test conditions are as follows: 190 ℃, oxygen pressure of 0.5MPa and heating speed of 10 ℃/min.
TABLE 1
The comparison shows that the ester compound can obviously improve the oxidation induction period as the base oil, has better oxidation resistance than alkyl naphthalene and mineral oil, and is the base oil with excellent oxidation resistance.
Example 9
Adding an additive T511 into the ester compound of example 1, the ester compound of example 5, the alkyl naphthalene and the mineral oil S6 respectively to prepare uniform solutions with the mass concentration of T511 of 0.5%, and performing DSC oxidation resistance tests on the solution samples respectively, wherein the test results are shown in Table 2, the test instruments are TA5000 DSC instruments of the American TA company, and the test conditions are as follows: 190 ℃, oxygen pressure of 0.5MPa and heating speed of 10 ℃/min.
TABLE 2
The comparison shows that the ester compound can obviously improve the oxidation induction period as the base oil, has better oxidation resistance than alkyl naphthalene and mineral oil, and is the base oil with excellent oxidation resistance.
The above embodiments are only used to illustrate the technical solutions of the embodiments of the present disclosure, and not to limit them; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present disclosure.
Claims (10)
1. The structure of the ester compound is shown as the formula (I):
in the formula (I), Ar ring group is C6～20Aryl (preferably C)6～15Aryl, more preferably C6～10Aryl, more preferably phenyl, naphthyl, anthracenyl);
n is an integer of 1 to 20 (preferably an integer of 1 to 15, more preferably an integer of 1 to 10, and further preferably an integer of 1 to 6);
n R groups are bonded to the Ar ring group;
n R groups are each independently selected from the group of formula (II), C1～30Is preferably independently selected from the group represented by the formula (II), C1～20More preferably, each of the straight-chain or branched alkyl groups and H is independently selected from the group represented by the formula (II), C1～10H) and at least one R group is selected from the group represented by formula (II);
in the formula (II), m is an integer of 1 to 10 (preferably an integer of 1 to 5, more preferably 1, 2 or 3); r1The radicals being selected from C1～30Is preferably selected from C1～20More preferably selected from C1～10Linear or branched alkyl groups of (a); m number of R2Each independently selected from C1～30Alkylene group of (2), a single bond (preferably selected from C)1～20Is more preferably selected from C1～10Linear or branched alkylene, single bond, with
Bonded R2The radicals are preferably selected from C1～10Linear or branched alkylene groups of (a); r3The radicals being 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);
m a 'groups are each independently selected from-CH ═ CH-, ethylene-, a group represented by formula (III), a group represented by formula (IV), a group represented by formula (V) and a group represented by formula (VI), and at least one a' group present in formula (II) is selected from a group represented by formula (III) or a group represented by formula (IV), the group represented by formula (III) or formula (IV) is bonded to the Ar ring group in formula (I), and represents a bonding end at which the group represented by formula (III) or formula (IV) is bonded to the Ar ring group in formula (I);
in the group represented by the formula (III), the group represented by the formula (IV), the group represented by the formula (V) and the group represented by the formula (VI), each R4Each 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 C6～20Aryl (preferably C)6～15Aryl, more preferably C6～10Aryl, more preferably phenyl, naphthyl, anthracenyl).
2. An ester compound according to claim 1, wherein the ester compound comprises one or more of the following compounds in any ratio:
3. a process for producing an ester compound, which comprises the step of reacting a compound represented by the formula (alpha) with a compound represented by the formula (beta),
in the formula (. alpha.), m is an integer of 1 to 10 (preferably an integer of 1 to 5, more preferably 1, 2 or 3); r is1The radicals being selected from C1～30Is preferably selected from C1～20More preferably selected from C1～10Linear or branched alkyl groups of (a); m R2Each independently selected from C1～30Alkylene group of (2), a single bond (preferably selected from C)1～20Linear chain of (2)Or a branched alkylene group, a single bond, more preferably C1～10A straight or branched alkylene group of (A), a single bond, and
bonded R2The radicals are preferably selected from C1～10Linear or branched alkylene groups of (a); r3The radicals being 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);
in the formula (. beta.), Ar ring group is C6～20Aryl (preferably C)6～15Aryl, more preferably C6～10Aryl, more preferably phenyl, naphthyl, anthracenyl); n' is an integer of 1 to 19 (preferably an integer of 1 to 14, more preferably an integer of 1 to 9, and further preferably an integer of 1 to 5);
n 'R' groups are bonded to the Ar ring group;
n 'R' radicals 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).
4. A method according to claim 3, wherein the compound of formula (α) is selected from one or more of the following compounds: octenoic acid, decenoic acid, undecenoic acid, dodecenoic acid, decatetraenoic acid, hexadecenoic acid, oleic acid, linoleic acid, linolenic acid, eicosenoic acid; and/or, the compound shown in the formula (beta) is selected from one or more of the following compounds: benzene, naphthalene, anthracene, methylnaphthalene, ethylnaphthalene, n-propylnaphthalene, 2-isopropylnaphthalene.
5. The method according to claim 3, wherein the mass ratio between the compound represented by the formula (α) and the compound represented by the formula (β) is 1: 0.1-1 (preferably 1: 0.2-1), and the reaction temperature is 60-200 deg.C (preferably 90-180 deg.C).
6. A process according to claim 3, characterized in that the compound of formula (α) is reacted with the compound of formula (β) in the presence of an inert gas.
7. A process according to claim 3, characterized in that a catalyst, preferably an acidic catalyst, is added to the reaction of the compound of formula (α) with the compound of formula (β).
8. The process of claim 7 wherein the catalyst is selected from the group consisting of Lewis acids, or mixtures thereof,
One or more of acid, solid acid, acidic ionic liquid and its supported catalyst, the carrier of the supported catalyst can be molecular sieve, alumina, zeolite, graphite, carbon black, resin (the acidic catalyst is preferably 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, phosphotungstic acid, silicon aluminum fluoride, perfluoroalkane sulfonic acid and its supported catalyst).
9. Use of the ester compound of claim 1 or 2 or the ester compound prepared according to the method of any one of claims 3 to 8 as a lubricating base oil.
10. A lubricating oil composition comprising the ester compound of claim 1 or 2 or the ester compound produced by the method of any one of claims 3 to 8 and a lubricating oil additive.
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