CN111072706B - Silole derivative, preparation method and application thereof, and photoluminescent lubricating grease - Google Patents
Silole derivative, preparation method and application thereof, and photoluminescent lubricating grease Download PDFInfo
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- CN111072706B CN111072706B CN201811212799.5A CN201811212799A CN111072706B CN 111072706 B CN111072706 B CN 111072706B CN 201811212799 A CN201811212799 A CN 201811212799A CN 111072706 B CN111072706 B CN 111072706B
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- Prior art keywords
- compound
- general formula
- silole
- grease
- formula
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- 239000004519 grease Substances 0.000 title claims abstract description 56
- 150000003967 siloles Chemical class 0.000 title claims abstract description 38
- 230000001050 lubricating effect Effects 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title abstract description 14
- -1 silole compound Chemical class 0.000 claims description 93
- 238000006243 chemical reaction Methods 0.000 claims description 72
- 239000002199 base oil Substances 0.000 claims description 52
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- 239000002562 thickening agent Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 22
- 238000010438 heat treatment Methods 0.000 claims description 21
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 21
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 239000000194 fatty acid Substances 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 238000007670 refining Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 238000000227 grinding Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 229920002396 Polyurea Polymers 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- 229910001507 metal halide Inorganic materials 0.000 claims description 6
- 150000005309 metal halides Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000010687 lubricating oil Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 239000007850 fluorescent dye Substances 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 238000003384 imaging method Methods 0.000 claims 1
- 238000005424 photoluminescence Methods 0.000 abstract description 4
- 238000005299 abrasion Methods 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 7
- 239000000344 soap Substances 0.000 description 7
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 6
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 6
- 235000021355 Stearic acid Nutrition 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 6
- 239000008117 stearic acid Substances 0.000 description 6
- 239000013638 trimer Substances 0.000 description 6
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 5
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 4
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 4
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 4
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 4
- DXFHSYZYJQBTSI-UHFFFAOYSA-N 2-pentaphen-1-yl-1H-silole Chemical compound C1(=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12)C1=CC=C[SiH2]1 DXFHSYZYJQBTSI-UHFFFAOYSA-N 0.000 description 3
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 2
- YGRVCNYIEKLRED-UHFFFAOYSA-N 4,4-diphenylbutylphosphane Chemical compound C=1C=CC=CC=1C(CCCP)C1=CC=CC=C1 YGRVCNYIEKLRED-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- 229960003280 cupric chloride Drugs 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- PKVRJCUKSNFIBN-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 PKVRJCUKSNFIBN-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- FPUIBHWOSCSYHI-UHFFFAOYSA-N 2-benzo[a]anthracen-1-yl-1H-silole Chemical compound C1(=CC=CC2=CC=C3C=C4C=CC=CC4=CC3=C12)C1=CC=C[SiH2]1 FPUIBHWOSCSYHI-UHFFFAOYSA-N 0.000 description 1
- NPBSBXCWBLLCJG-UHFFFAOYSA-N 4-[[(4-carboxyphenyl)methyldisulfanyl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CSSCC1=CC=C(C(O)=O)C=C1 NPBSBXCWBLLCJG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical group CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910021575 Iron(II) bromide Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000003490 Thiodipropionic acid Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000010425 asbestos Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 238000012984 biological imaging Methods 0.000 description 1
- PAYXZLUSJAPVRT-UHFFFAOYSA-N butyl n-butoxycarbonyliminocarbamate Chemical compound CCCCOC(=O)N=NC(=O)OCCCC PAYXZLUSJAPVRT-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Chemical group 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- GNVFTBURMUIKJD-UHFFFAOYSA-L dichlororhodium;triphenylphosphane Chemical compound Cl[Rh]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 GNVFTBURMUIKJD-UHFFFAOYSA-L 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- NCBFTYFOPLPRBX-UHFFFAOYSA-N dimethyl azodicarboxylate Substances COC(=O)N=NC(=O)OC NCBFTYFOPLPRBX-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 229940046149 ferrous bromide Drugs 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 229940076136 ferrous iodide Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- HEJPGFRXUXOTGM-UHFFFAOYSA-K iron(3+);triiodide Chemical compound [Fe+3].[I-].[I-].[I-] HEJPGFRXUXOTGM-UHFFFAOYSA-K 0.000 description 1
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
- BQZGVMWPHXIKEQ-UHFFFAOYSA-L iron(ii) iodide Chemical compound [Fe+2].[I-].[I-] BQZGVMWPHXIKEQ-UHFFFAOYSA-L 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- NCBFTYFOPLPRBX-AATRIKPKSA-N methyl (ne)-n-methoxycarbonyliminocarbamate Chemical compound COC(=O)\N=N\C(=O)OC NCBFTYFOPLPRBX-AATRIKPKSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- IGTVAJJAPJKARK-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 IGTVAJJAPJKARK-UHFFFAOYSA-N 0.000 description 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- GZKMGAXTHYGXEO-UHFFFAOYSA-M ruthenium(1+);triphenylphosphane;chloride Chemical compound [Ru]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 GZKMGAXTHYGXEO-UHFFFAOYSA-M 0.000 description 1
- PMKLSZDLLHGDMO-UHFFFAOYSA-L ruthenium(2+);triphenylphosphane;dichloride Chemical compound Cl[Ru]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 PMKLSZDLLHGDMO-UHFFFAOYSA-L 0.000 description 1
- BFPFOLJFUVTHEP-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BFPFOLJFUVTHEP-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- FEQPHYCEZKWPNE-UHFFFAOYSA-K trichlororhodium;triphenylphosphane Chemical compound Cl[Rh](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FEQPHYCEZKWPNE-UHFFFAOYSA-K 0.000 description 1
- CMTKJYPJPSONIT-UHFFFAOYSA-K trichlororuthenium;triphenylphosphane Chemical compound Cl[Ru](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMTKJYPJPSONIT-UHFFFAOYSA-K 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229960001939 zinc chloride Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
- C10M139/04—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00 having a silicon-to-carbon bond, e.g. silanes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
-
- 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
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/124—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers thereof
- C10M2207/1245—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers thereof used as thickening agent
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a silole derivative, a preparation method and application thereof, and photoluminescent lubricating grease containing the silole derivative. The silole derivative has a structure shown in a general formula (I):
Description
Technical Field
The invention relates to a silole derivative, in particular to a silole derivative with a luminescent property.
Background
Traditional organic chromophores generally emit light strongly at low concentrations, but emit light weakly or even not at high concentrations or in a solid state, and exhibit an aggregate fluorescence quenching effect. This is because in the aggregate state, the strong intermolecular interactions lead to an enhancement of the non-radiative decay process of the excited state, with a significant decrease in fluorescence quantum yield. In the practical application process, the practical application of the organic light-emitting material is limited to a great extent by the aggregate fluorescence quenching effect. In recent years, research shows that some compounds show the opposite properties to the traditional organic luminescent compounds, not only do not have aggregation fluorescence quenching effect, but also show Aggregation Induced Emission (AIE) properties, and the appearance of the aggregation induced emission compounds provides a new solution for the application of organic luminescent materials in a solid state or at high concentration.
The lubricating grease is a solid to semi-fluid product prepared by dispersing a thickening agent in a liquid lubricant, has the functions of lubrication, protection and sealing, and plays a vital role in industrial machinery, agricultural machinery, the transportation industry, the aerospace industry, the electronic information industry and various military equipment.
Under some dark working conditions, the monitoring of the lubricating grease has great difficulty. At present, the related reports of the luminescent grease are rarely seen.
Disclosure of Invention
The invention provides a silole derivative, a preparation method and application thereof, and photoluminescent lubricating grease containing the silole derivative.
The silole derivative has a structure shown in a general formula (I):
in the general formula (I), each R is independently selected from hydrogen and C1-6A linear or branched alkyl group; x is an integer between 0 and 5; y is an integer of 0 to 3; z is an integer between 1 and 4; r1Selected from hydrogen, C1-6Straight or branched alkyl, C6-10An aryl group; r2Selected from the group consisting of single bond, C1-6Straight or branched chain alkylene.
According to the invention, preferably, in the general formula (I), each R is chosen from hydrogen, C1-4A linear or branched alkyl group; x is an integer between 0 and 3; y is 0, 1 or 2; z is 1,2 or 3; r is1Selected from hydrogen, C1-4Straight or branched chain alkyl, phenyl; r is2Is selected from C1-4Straight chain or branched alkylene.
According to the present invention, preferably, the silole derivatives that may be cited include one or more of the following compounds:
the method for producing a silole derivative according to the present invention comprises a step of reacting a silole compound represented by the general formula (II), a phenol compound represented by the general formula (III), and a compound represented by the general formula (IV),
in the general formula (II), each R is independently selected from hydrogen and C1-6A linear or branched alkyl group; x is an integer of 0 to 5; r1Selected from hydrogen, C1-6Straight or branched alkyl, C6-10An aryl group; in the general formula (III), each R is independently selected from hydrogen and C1-6A linear or branched alkyl group; y is an integer of 0 to 3;x is selected from F, Cl, Br and I; in the general formula (IV), each R is independently selected from hydrogen and C1-6A linear or branched alkyl group; y is an integer of 0 to 3; z is an integer between 1 and 4; r2Selected from single bond, C1-6A linear or branched alkylene group; x is selected from F, Cl, Br, I and OH.
According to the preparation process of the present invention, preferably, in the general formula (II), each R is independently selected from hydrogen, C1-4A linear or branched alkyl group; x is an integer between 0 and 3; r1Selected from hydrogen, C1-4Straight or branched chain alkyl, phenyl; in the general formula (III), each R is independently selected from hydrogen and C1-4A linear or branched alkyl group; y is 0, 1 or 2; x is selected from Cl, Br, I and OH; in the general formula (IV), each R is independently selected from hydrogen and C1-4A linear or branched alkyl group; y is 0, 1 or 2; z is 1,2 or 3; r2Selected from single bond, C1-4A linear or branched alkylene group; x is selected from Cl, Br, I and OH.
According to the production method of the present invention, preferably, the silole compound represented by the general formula (II) includes:
according to the production method of the present invention, preferably, the phenol compound represented by the general formula (III) includes:
according to the production method of the present invention, preferably, the compound represented by the general formula (IV) includes:
according to the production method of the present invention, preferably, in the reaction, the molar ratio of the silole compound represented by the general formula (II) to the phenol compound represented by the general formula (III) or the compound represented by the general formula (IV) is preferably 1: 0.5-5: 0.2 to 5, most preferably 1: 0.8-3: 0.3 to 3.
According to the preparation method provided by the invention, the reaction temperature is preferably 0-50 ℃, and preferably 15-35 ℃.
According to the preparation method provided by the invention, the reaction time is preferably 6-96 h, and preferably 12-72 h.
According to the production method of the present invention, preferably, a solvent is added in the reaction. The solvent is preferably C1～C10Examples of the organic amine and furan include methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, propylamine, dipropylamine, tripropylamine and tetrahydrofuran, and most preferably C1～C10The volume ratio of the organic amine to the furan is preferably 1: 0.1 to 10. The solvent may be removed by a method known in the art after the completion of the reaction, and the removal method is not particularly limited, and includes distillation, evaporation, and column chromatography. Preferably, the silole derivative of the present invention is isolated and purified by column chromatography, and a mixed solvent of dichloromethane/petroleum ether may be used as an eluent, and the volume ratio of dichloromethane to petroleum ether is preferably 1: 0.5 to 5.
According to the production method of the present invention, it is preferable that the silole compound represented by the general formula (II) is reacted with the phenol compound represented by the general formula (III) and then the reaction product is reacted with the compound represented by the general formula (IV).
According to the production method of the present invention, preferably, in the reaction of the silole compound represented by the general formula (II) with the phenol compound represented by the general formula (III), the molar ratio between the silole compound represented by the general formula (II) and the phenol compound represented by the general formula (III) is preferably 1: 0.5 to 5, more preferably 1: 0.8 to 3; the reaction temperature is preferably 0-50 ℃, and more preferably 15-35 ℃; generally, the longer the reaction time, the higher the conversion, and the reaction time may be 6 to 96 hours, preferably 12 to 72 hours.
According to the production method of the present invention, it is preferable to add a catalyst to the reaction of the silole compound represented by the general formula (II) with the phenol compound represented by the general formula (III). The catalyst is preferably one or more of a metal phosphine complex, a metal halide and a hydrocarbyl phosphine compound, more preferably a mixture of a metal phosphine complex, a metal halide and a hydrocarbyl phosphine compound, and the molar ratio of the three is preferably 1: 0.1-10: 0.1 to 10, more preferably 1: 0.2-5: 0.5 to 2.
According to the preparation method of the present invention, preferably, the metal phosphine complex has a structure of
Wherein M is Pd, Ru or Rh, L is selected from PPh3Ph, F, Cl, Br, I. The metal phosphine complex can be one or more of tetrakis (triphenylphosphine) palladium, tris (triphenylphosphine) palladium chloride, bis (triphenylphosphine) palladium dichloride, (triphenylphosphine) palladium trichloride, tetrakis (triphenylphosphine) ruthenium, tris (triphenylphosphine) ruthenium chloride, bis (triphenylphosphine) ruthenium dichloride, (triphenylphosphine) ruthenium trichloride, tetrakis (triphenylphosphine) rhodium, tris (triphenylphosphine) rhodium chloride, bis (triphenylphosphine) rhodium dichloride and (triphenylphosphine) rhodium trichloride, and preferably one or more of tetrakis (triphenylphosphine) palladium, tris (triphenylphosphine) palladium chloride, bis (triphenylphosphine) palladium dichloride and (triphenylphosphine) palladium trichloride.
According to the preparation method of the present invention, preferably, the metal halide may be one or more of a copper halide, an iron halide and a zinc halide, for example, one or more of cupric chloride, cuprous chloride, cupric bromide, cuprous bromide, cupric iodide, cuprous iodide, ferric chloride, ferrous chloride, ferric bromide, ferrous bromide, ferric iodide, ferrous iodide, zinc chloride, zinc bromide, zinc iodide and zinc iodide may be used, and more preferably one or more of cupric chloride, cuprous chloride, cupric bromide, cuprous bromide, cupric iodide and cuprous iodide.
According to the production method of the present invention, preferably, the hydrocarbyl phosphine compound has a structure of
Wherein each R is independently selected from C6～C10Aryl and C1～C6Wherein at least one R is C6～C10Aryl group of (2). Said C is6～C10The aryl group of (a) may be selected from phenyl, naphthyl; said C is1～C6The linear or branched alkyl group of (a) may be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, hexyl or isohexyl. The hydrocarbyl phosphine compound can be selected from triphenylphosphine and diphenylbutylphosphine.
According to the preparation method of the present invention, in the reaction of the silole compound represented by the general formula (II) with the phenol compound represented by the general formula (III), the amount of the catalyst to be added is preferably 1% to 100% of the amount of the silole compound represented by the general formula (II) in terms of substance.
According to the production method of the present invention, preferably, in the reaction of the reaction product of the silole compound represented by the general formula (II) with the phenol compound represented by the general formula (III) and the compound represented by the general formula (IV), the molar ratio between the silole compound represented by the general formula (II) and the compound represented by the general formula (IV) is preferably 1: 0.2 to 5, more preferably 1: 0.3 to 3; the reaction temperature is preferably 0-50 ℃, and more preferably 15-35 ℃; generally, the longer the reaction time, the higher the conversion, and the reaction time may be 6 to 96 hours, preferably 12 to 72 hours.
According to the production method of the present invention, it is preferable to add a catalyst to the reaction of the silole compound represented by the general formula (II) with the phenol compound represented by the general formula (III) and the compound represented by the general formula (IV). The catalyst is preferably a hydrocarbyl phosphine compound and/or an azo compound, more preferably a mixture of the hydrocarbyl phosphine compound and the azo compound, and the molar ratio of the hydrocarbyl phosphine compound to the azo compound is preferably 1: 0.1 to 10, more preferably 1: 0.2 to 5. The hydrocarbyl phosphine compound preferably has the structure
Wherein each R is independently selected from C6～C10Aryl and C1～C6Wherein at least one R is C6～C10Aryl group of (1). Said C is6～C10Aryl of (A) may be selected from phenylNaphthyl; said C is1～C6The linear or branched alkyl group of (a) may be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, hexyl or isohexyl. The hydrocarbyl phosphine compound can be selected from triphenylphosphine and diphenylbutylphosphine. The preferable structure of the azo compound is as follows:
wherein each R' is the same or different from each other and is independently selected from hydrogen and C1-6Straight or branched alkyl, C3-10Cycloalkyl radical, C6-10Aryl and C1-6An alkoxy group. The azo compound may preferably be one or more selected from dimethyl azodicarboxylate, diethyl azodicarboxylate, dipropyl azodicarboxylate and dibutyl azodicarboxylate.
According to the production method of the present invention, in the reaction of the reaction product of the silole compound represented by the general formula (II) with the phenol compound represented by the general formula (III) and the compound represented by the general formula (IV), the amount of the catalyst to be added is preferably 1% to 100% of the amount of the silole compound represented by the general formula (II).
The silole derivative has excellent photoluminescence performance, can emit light under ultraviolet irradiation, and can be applied to light-emitting parts and devices, fluorescent probes, biological imaging, lubricating oil and lubricating grease.
The invention also provides lubricating grease which comprises the silole derivative, a thickening agent and lubricating base oil. The silole derivative accounts for 0.01-5.0% of the total mass of the lubricating grease, and preferably 0.1-1.0%; the thickening agent accounts for 5-30%, preferably 10-20% of the total mass of the lubricating grease; the lubricating base oil constitutes the main component of the grease.
The thickening agent comprises one or more of a polyurea thickening agent, a lithium-based thickening agent, a composite lithium-based thickening agent, a calcium-based thickening agent and a composite aluminum-based thickening agent, preferably the polyurea thickening agent, the lithium-based thickening agent, the composite lithium-based thickening agent and the composite aluminum-based thickening agent, and most preferably the lithium-based thickening agent.
The base oil may be one or more of mineral oil, vegetable oil and synthetic oil, preferably mineral oil and synthetic oil.
The lubricating grease disclosed by the invention has excellent photoluminescence performance and extreme pressure anti-wear performance.
The preparation method of the lubricating grease comprises the following steps: mixing lubricating base oil, thickener and silole derivative, refining, and grinding into grease. The refining operation temperature is 160-240 ℃, and preferably 180-220 ℃; the refining operation time is 10-240 min, preferably 20-60 min. All of the lubricating base oil, the silole derivative and the thickening agent can be mixed and refined, or part of the lubricating base oil, part of the silole derivative and the thickening agent can be mixed and refined, and then the lubricating base oil, the silole derivative and the thickening agent are mixed.
The thickener can be a soap-based thickener or a non-soap-based thickener. The soap-based thickener is preferably a metal soap, and can be a single metal soap or a composite metal soap, and the metal can be one or more of lithium, sodium, calcium, aluminum, zinc, potassium, barium, lead and manganese. The non-soap-based grease thickener is preferably one or more of graphite, carbon black, asbestos, polyurea group, bentonite and organic clay.
The grease of the present invention is preferably polyurea grease, lithium-based grease and complex aluminum-based grease.
The preparation method of the polyurea lubricating grease comprises the following steps: mixing part of lubricating base oil, the silole derivative, amine and isocyanate, reacting at 65-95 ℃ for 10-60min, continuously heating to 190-220 ℃ after complete reaction, refining at high temperature, adding the rest base oil, cooling to 60-120 ℃, and grinding into grease. The amine is C2～C20Alkylamine and/or C6～C20Aromatic amines, such as one or more of octadecylamine, cyclohexylamine, aniline; the isocyanate is C2～C20The isocyanate of (b) may be one or more of Toluene Diisocyanate (TDI) and 4, 4' -diphenylmethane diisocyanate (MDI).
The preparation method of the lithium-based lubricating grease comprises the following steps: will partiallyMixing and heating lubricating base oil and fatty acid in a reaction kettle, heating to 40-90 ℃, adding the aqueous solution of the silole derivative and lithium hydroxide, heating to remove water, continuously heating to 190-220 ℃ for high-temperature refining, adding the rest lubricating base oil, cooling to 60-120 ℃, and grinding into grease. The fatty acid is C12～C20Fatty acid and/or C12～C20The hydroxy fatty acid can be one or more of lauric acid, palmitic acid, stearic acid and 12-hydroxystearic acid.
The preparation method of the composite aluminum-based lubricating grease comprises the following steps: mixing and heating part of base oil, fatty acid and micromolecular acid in a reaction kettle, heating to 40-90 ℃, adding the silole derivative, mixing and heating the other part of lubricating base oil and an aluminum alkoxide compound to 40-100 ℃, adding the mixture into the reaction kettle after the aluminum alkoxide compound is completely dissolved, continuously heating to 190-220 ℃ for high-temperature refining, adding the rest of lubricating base oil, cooling to 60-120 ℃, and grinding into grease. The fatty acid is C12～C20Fatty acid and/or C12～C20Hydroxy fatty acid, which can be one or more of lauric acid, palmitic acid, stearic acid and 12-hydroxystearic acid; the small molecular acid is C2～C11The organic acid of (2) can be one or more of acetic acid, propionic acid, oxalic acid, adipic acid, azelaic acid, sebacic acid and terephthalic acid; the aluminium alkoxide compound is preferably selected from aluminium isopropoxide, aluminium isopropoxide dimer, aluminium isopropoxide trimer.
According to the method for preparing a grease of the present invention, it is preferable that the silole derivative is dissolved in a solvent in advance. The solvent is preferably an aromatic hydrocarbon solvent, for example, benzene, toluene or xylene, and the weight of the solvent is 0.5 to 100 times (preferably 1 to 20 times) that of the silole derivative.
The lubricating grease has excellent photoluminescence performance and extreme pressure abrasion resistance, and can be applied to relevant mechanical equipment in the electrical appliance industry, the metallurgical industry, the food industry, the paper industry, the automobile industry and the airplane industry.
Detailed Description
The main raw materials used are as follows:
1-alkynyl-1, 2,3,4, 5-pentaphenyl silole, 1-methyl-1-alkynyl-2, 3,4, 5-tetraphenyl silole, p-iodophenol, cuprous iodide, triphenylphosphine, palladium tetratriphenylphosphine, bis (4-benzyl formate) disulfide, diethyl azodicarboxylate, octadecylamine, MDI, 12-hydroxystearic acid, stearic acid, benzoic acid, lithium hydroxide monohydrate, aluminum isopropoxide trimer, tetrahydrofuran, triethylamine, dichloromethane, petroleum ether and other chemical reagents are from Bailingwei reagent company, Inokay reagent company or Sigma reagent company, and are analytically pure; the PAO10 base oil was obtained from Exxon Mobil.
Example 1
487mg (1mmol) of 1-alkynyl-1, 2,3,4, 5-pentaphenylsilol, 264mg (1.2mmol) of p-iodophenol, 19mg (0.1mmol) of cuprous iodide, 26mg (0.1mmol) of triphenylphosphine and 23mg (0.02mmol) of palladium tetratriphenylphosphine and 30mL of tetrahydrofuran/triethylamine (2/1, v/v) are placed in a 100mL Schlenk reaction flask and reacted at room temperature for 48 hours. After the reaction was completed, filtration was performed and the filtrate was spin-dried, and the product was isolated and purified by column chromatography using a mixed solvent of dichloromethane/petroleum ether (1/1, v/v) as an eluent, to obtain 430mg of a yellow solid product in a yield of 74%. The nuclear magnetic result of the product is as follows:1H NMR(400MHz,CDCl3),δ(TMS,ppm):7.74(m,2H),7.36(m,3H),7.15–6.85(m,24H)；MS(MALDI-TOF):m/zcalcd:578.2[M]+,found:578.2。
the reaction formula of example 1 is as follows:
1158mg (2mmol) of 1- (4-hydroxyphenylalkynyl) -1,2,3,4, 5-pentaphenylsilol, 334mg (1mmol) of bis (4-carboxybenzyl) disulfide, 630mg (2.4mmol) of triphenylphosphine and 30mL of tetrahydrofuran are charged in a 100mL reaction flask, and 418mg (2.4mmol) of diethyl azodicarboxylate is slowly added dropwise at 0 ℃ and then reacted at room temperature for 18 hours. After the reaction is finished, filtering and spin-drying the filtrate, and performing column chromatography by using a dichloromethane/petroleum ether (1/2, v/v) mixed solvent as an eluentThe product was isolated and purified to give 1080mg of a yellow solid product in 74% yield. The nuclear magnetic result of the product is as follows:1H NMR(400MHz,CDCl3),δ(TMS,ppm):7.92(m,4H),7.72(m,4H),7.43(m,4H),7.35(m,6H),7.15–6.87(m,48H),3.38(m,4H)；MS(MALDI-TOF):m/z calcd:1455.4[M]+,found:1455.4。
the reaction formula of example 2 is as follows:
425mg (1mmol) of 1-methyl-1-alkynyl-2, 3,4, 5-tetraphenylsilole, 264mg (1.2mmol) of p-iodophenol, 19mg (0.1mmol) of cuprous iodide, 26mg (0.1mmol) of triphenylphosphine and 23mg (0.02mmol) of palladium tetratriphenylphosphine and 30mL of tetrahydrofuran/triethylamine (2/1, v/v) were added to a 100mL Schlenk reaction flask and reacted at room temperature for 48 hours under nitrogen. After the reaction, the reaction mixture was filtered, and the filtrate was spin-dried, and the product was separated and purified by column chromatography using a dichloromethane/petroleum ether (1/1, v/v) mixed solvent as an eluent, to obtain 400mg of a yellow solid product in a yield of 78%. The nuclear magnetic result of the product is as follows:1H NMR(400MHz,CDCl3),δ(TMS,ppm):7.15–6.85(m,24H),0.22(s,3H)；MS(MALDI-TOF):m/zcalcd:516.2[M]+,found:516.2。
the reaction formula for example 3 is shown below:
949mg (2mmol) of 1- (4-hydroxyphenylalkynyl) -1,2,3,4, 5-pentaphenylsilol, 334mg (1mmol) of thiodipropionic acid, 630mg (2.4mmol) of triphenylphosphine and 30mL of tetrahydrofuran are placed in a 100mL reaction flask, 418mg (2.4mmol) of diethyl azodicarboxylate is slowly added dropwise at 0 ℃ and the reaction is carried out at room temperature for 18 hours. After the reaction is finished, filtering and rotating the filtrateThe product was separated and purified by column chromatography using a mixed solvent of dichloromethane/petroleum ether (1/2, v/v) as an eluent to give 870mg of a yellow solid product in 74% yield. The nuclear magnetic result of the product is as follows:1H NMR(400MHz,CDCl3),δ(TMS,ppm):7.92(m,4H),7.43(m,4H),7.15–6.87(m,48H),3.42(m,4H),0.22(s,6H)；MS(MALDI-TOF):m/z calcd:1330.4[M]+,found:1330.4。
the reaction formula of example 4 is as follows:
145 g of PAO10 base oil and 44.39 g of octadecylamine were mixed and heated to 60 ℃ in a reaction kettle, 2.5 g of bis (4- (1,2,3,4, 5-pentaphenylsilolopynyl)) phenyl dithiodibenzylbenzoate prepared in example 2 was dissolved in 25 g of toluene and added to the reaction kettle, 145 g of PAO10 base oil and 20.61 g of MDI were mixed and heated to 60 ℃, after all MDI was dissolved, the mixture was added to the reaction kettle, the temperature was raised to 80 ℃ for reaction for 30min, the temperature was raised to 210 ℃ continuously, 145 g of PAO10 base oil was added, the mixture was cooled to about 100 ℃ and then ground to grease.
Example 6
145 g of PAO10 base oil and 44.39 g of octadecylamine were mixed and heated to 60 ℃ in a reaction kettle, 2.5 g of bis (4- (1-methyl-2, 3,4, 5-tetraphenylsilolopyrrolyl) phenyl dithiodibenzylbenzoate prepared in example 4 was dissolved in 25 g of toluene and added to the reaction kettle, 145 g of PAO10 base oil and 20.61 g of MDI were mixed and heated to 60 ℃ and added to the reaction kettle after all MDI was dissolved, the temperature was raised to 80 ℃ for reaction for 30min, the temperature was further raised to 210 ℃, 145 g of PAO10 base oil was added and cooled to about 100 ℃ and ground to grease.
Example 7
145 g of PAO10 base oil and 44.39 g of octadecylamine were mixed and heated to 60 ℃ in a reaction kettle, 145 g of PAO10 base oil and 20.61 g of MDI were mixed and heated to 60 ℃, added to the reaction kettle after all MDI was dissolved, heated to 80 ℃ for reaction for 30min, further heated to 210 ℃, 145 g of PAO10 base oil was added to cool to about 100 ℃, 2.5 g of bis (4- (1,2,3,4, 5-pentaphenylsilolopynyl)) phenyl dithiodibenzylbenzoate prepared in example 2 was added and ground into grease.
Comparative example 1
145 g of PAO10 base oil and 44.39 g of octadecylamine are mixed and heated to 60 ℃ in a reaction kettle, 145 g of PAO10 base oil and 20.61 g of MDI are mixed and heated to 60 ℃, the mixture is added into the reaction kettle after the MDI is completely dissolved, the temperature is increased to 80 ℃ for reaction for 30min, the temperature is continuously increased to 210 ℃, 145 g of PAO10 base oil is added, the mixture is cooled to about 100 ℃ and is ground into grease.
The greases of example 5, example 6, example 7 and comparative example 1 were evaluated for performance according to GB/T3498, GB/T269, SH/T0719, SH/T0202, SH/T0204 and SH/T0324, and the evaluation results are shown in Table 1.
TABLE 1 evaluation results
Example 8
300 g of PAO10 base oil and 39.21 g of 12-hydroxystearic acid were mixed in a reactor and heated to 85 ℃, 2.5 g of bis (4- (1,2,3,4, 5-pentaphenylthiapyrrolyl) phenyl dithiodibenzylbenzoate from example 2 was dissolved in 25 g of toluene and added to the reactor, 6.06 g of lithium hydroxide monohydrate was mixed with 40 g of distilled water and heated to 95 ℃, the mixture was added to the reactor after all the lithium hydroxide was dissolved, the temperature was raised to 210 ℃ after the water removal by heating, 160 g of PAO10 base oil was added, and the mixture was cooled and ground to a fat.
Example 9
300 g of PAO10 base oil and 39.21 g of 12-hydroxystearic acid were mixed in a reactor and heated to 85 ℃, 2.5 g of bis (4- (1-methyl-2, 3,4, 5-tetraphenylthiapyrrolyl) phenyl dithiodibenzylbenzoate from example 4 was dissolved in 25 g of toluene and added to the reactor, 6.06 g of lithium hydroxide monohydrate was mixed with 40 g of distilled water and heated to 95 ℃, the mixture was added to the reactor after all the lithium hydroxide was dissolved, the temperature was raised to 210 ℃ after the water was removed by heating, 160 g of PAO10 base oil was added, and the mixture was cooled and ground to a fat.
Comparative example 2
300 g of PAO10 base oil and 39.21 g of 12-hydroxystearic acid are mixed and heated to 85 ℃ in a reaction kettle, 6.06 g of lithium hydroxide monohydrate and 40 g of distilled water are mixed and heated to 95 ℃, the mixture is added into the reaction kettle after the lithium hydroxide is completely dissolved, the temperature is continuously raised to 210 ℃ after the water is removed by heating, 160 g of PAO10 base oil is added, and the mixture is cooled and ground into grease.
The greases of example 8, example 9 and comparative example 2 were evaluated for their properties in the same manner as described above, and the results are shown in Table 2.
TABLE 2 evaluation results
Example 10
200 g of PAO10 base oil, 32.5 g of stearic acid and 14 g of benzoic acid are mixed and heated to 90 ℃ in a reaction kettle, 2.5 g of bis (4- (1,2,3,4, 5-pentaphenylsilolophanyl) phenyl dithiodibenzylbenzoate prepared in example 2 are dissolved in 25 g of toluene and added into the reaction kettle, 100 g of PAO10 base oil and 32 g of aluminum isopropoxide trimer are mixed and heated, the mixture is added into the reaction kettle after the aluminum isopropoxide trimer is completely dissolved, the temperature is continuously increased to 210 ℃ for reaction for 30 minutes, 150 g of PAO10 base oil is added, and the mixture is cooled and ground into grease.
Example 11
200 g of PAO10 base oil, 32.5 g of stearic acid and 14 g of benzoic acid were mixed in a reaction vessel and heated to 90 ℃, 2.5 g of bis (4- (1-methyl-2, 3,4, 5-tetraphenylsilolopynyl)) phenyl dithiodibenzylbenzoate obtained in example 4 was dissolved in 25 g of toluene and added to the reaction vessel, 100 g of PAO10 base oil and 32 g of aluminum isopropoxide trimer were mixed and heated, after all of the aluminum isopropoxide trimer was dissolved, the mixture was added to the reaction vessel, the reaction vessel was heated to 210 ℃ for 30 minutes, 150 g of PAO10 base oil was added, and the mixture was cooled and ground to fat.
Comparative example 3
200 g of PAO10 base oil, 32.5 g of stearic acid and 14 g of benzoic acid are mixed and heated to 90 ℃ in a reaction kettle, 100 g of PAO10 base oil and 32 g of aluminum isopropoxide tripolymer are mixed and heated, the mixture is added into the reaction kettle after the aluminum isopropoxide tripolymer is completely dissolved, the temperature is continuously increased to 210 ℃ for reaction for 30 minutes, 150 g of PAO10 base oil is added, and the mixture is cooled and ground into grease.
The greases of example 10, example 11 and comparative example 3 were evaluated for their properties in the same manner as described above, and the evaluation results are shown in Table 3.
TABLE 3 evaluation results
Claims (24)
1. A silole derivative has a structure shown in a general formula (I):
in the general formula (I), each R is independently selected from hydrogen and C1-6A linear or branched alkyl group; x is an integer between 0 and 5; y is an integer of 0 to 3; z is an integer between 1 and 4; r1Selected from hydrogen, C1-6Straight or branched alkyl, C6-10An aryl group; r is2Is selected from C1-6Straight or branched chain alkylene.
2. Silole derivatives according to claim 1, characterized in that in general formula (I) each R is selected from hydrogen, C1-4A linear or branched alkyl group; x is an integer between 0 and 3; y is 0, 1 or 2; z is 1,2 or 3; r1Selected from hydrogen, C1-4Straight or branched chain alkyl, phenyl; r2Is selected from C1-4Straight or branched chain alkylene.
3. Silole derivatives according to claim 1, characterized in that they are selected from one or more of the following compounds:
4. a method for producing the silole derivative according to any one of claims 1 to 3, which comprises reacting a silole compound represented by the general formula (II), a phenol compound represented by the general formula (III), or a compound represented by the general formula (IV),
in the general formula (II), each R is independently selected from hydrogen and C1-6A linear or branched alkyl group; x is an integer between 0 and 5; r1Selected from hydrogen, C1-6Straight or branched alkyl, C6-10An aryl group; in the general formula (III), each R is independently selected from hydrogen and C1-6A linear or branched alkyl group; y is an integer of 0 to 3; x is selected from F, Cl, Br and I; in the general formula (IV), each R is independently selected from hydrogen and C1-6A linear or branched alkyl group; y is an integer of 0 to 3; z is an integer between 1 and 4; r is2Is selected from C1-6A linear or branched alkylene group; x is selected from F, Cl, Br, I and OH.
5. The process according to claim 4, wherein in the general formula (II), each R is independently selected from hydrogen, C1-4A linear or branched alkyl group; x is an integer between 0 and 3; r1Selected from hydrogen, C1-4Straight or branched chain alkyl, phenyl; in the general formula (III), each R is independently selected from hydrogen and C1-4A linear or branched alkyl group; y is 0, 1 or 2; x is selected from Cl, Br and I; in the general formula (IV), each R is independently selected from hydrogen and C1-4A linear or branched alkyl group; y is 0, 1 or 2; z is 1,2 or 3; r2Is selected from C1-4A linear or branched alkylene group; x is selected from Cl, Br, I and OH.
6. The method according to claim 4, wherein the silole compound of formula (II) is selected from one or more of the following compounds:
the phenol compound represented by the general formula (III) is selected from one or more of the following compounds:
the compound shown in the general formula (IV) is selected from one or more of the following compounds:
7. the process according to claim 4, wherein the molar ratio of the silole compound of the formula (II) to the phenol compound of the formula (III) to the compound of the formula (IV) in the reaction is 1: 0.5-5: 0.2 to 5; the reaction temperature is 0-50 ℃.
8. The process according to claim 4, wherein the silole compound represented by the general formula (II) is reacted with the phenol compound represented by the general formula (III), and the reaction product is reacted with the compound represented by the general formula (IV).
9. The process according to claim 8, wherein in the reaction of the silole compound of formula (II) with the phenol compound of formula (III), the molar ratio between the silole compound of formula (II) and the phenol compound of formula (III) is 1: 0.5 to 5; the reaction temperature is 0-50 ℃.
10. The method according to claim 8, wherein a catalyst is added to the reaction of the silole compound of the general formula (II) with the phenol compound of the general formula (III), and the catalyst is one or more of a metal phosphine complex, a metal halide and a hydrocarbyl phosphine compound.
11. The process according to claim 8, wherein a catalyst is added to the reaction of the silole compound of the formula (II) with the phenol compound of the formula (III), and the catalyst is a mixture of a metal phosphine complex, a metal halide and a hydrocarbyl phosphine compound, and the molar ratio of the three is 1: 0.1-10: 0.1 to 10.
12. The method of claim 10, wherein the metal isThe phosphine complex has the structure
Wherein M is Pd, Ru or Rh, L is selected from PPh3、Ph、F、Cl、Br、I；
The metal halide is selected from one or more of copper halide, iron halide and zinc halide;
the hydrocarbyl phosphine compound has the structure
Wherein each R is independently selected from C6~C10Aryl and C1~C6Wherein at least one R is C6~C10Aryl group of (2).
13. The process according to claim 8, wherein in the reaction of the reaction product of the silole compound of the formula (II) with the phenol compound of the formula (III) and the compound of the formula (IV), the molar ratio of the silole compound of the formula (II) to the compound of the formula (IV) is 1: 0.2 to 5; the reaction temperature is 0-50 ℃.
14. The process according to claim 8, wherein a catalyst is added to the reaction of the reaction product of the silole compound represented by the general formula (II) with the phenol compound represented by the general formula (III) and the compound represented by the general formula (IV), and the catalyst is a hydrocarbyl phosphine compound and/or an azo compound.
15. The process according to claim 8, wherein a catalyst which is a mixture of a hydrocarbyl phosphine compound and an azo compound is added to the reaction of the reaction product of the silole compound of the formula (II) with the phenol compound of the formula (III) and the compound of the formula (IV) in a molar ratio of 1: 0.1 to 10.
16. The method of claim 14, wherein the hydrocarbyl phosphine compound has the structure
Wherein each R is independently selected from C6~C10Aryl and C1~C6Wherein at least one R is C6~C10Aryl of (a); the azo compound has the structure as follows:
wherein each R' is the same or different from each other and is independently selected from hydrogen and C1-6Straight or branched alkyl, C3-10Cycloalkyl radical, C6-10Aryl and C1-6An alkoxy group.
17. Use of the silole derivative according to any of claims 1 to 3 or prepared according to any of claims 4 to 16 in light-emitting components and devices, fluorescent probes, bio-imaging, lubricating oils and greases.
18. A grease comprising the silole derivative according to any one of claims 1 to 3 or the silole derivative prepared by the method according to any one of claims 4 to 16, a thickener and a lubricating base oil.
19. The grease of claim 18 wherein the silole derivative comprises 0.01% to 5.0% of the total mass of the grease; the thickening agent accounts for 5-30% of the total mass of the lubricating grease; the lubricating base oil constitutes the main component of the grease.
20. A method of preparing a grease according to claim 18 or 19, comprising: mixing lubricating base oil, thickener and silole derivative, refining, and grinding into grease.
21. A method for preparing a grease according to claim 20, wherein the grease is a polyurea grease, and the method comprises: mixing part of lubricating base oil, silole derivatives, amine and isocyanate, reacting at 65-95 ℃ for 10-60min, continuously heating to 190-220 ℃ after complete reaction, refining at high temperature, adding the rest base oil, cooling to 60-120 ℃, and grinding into grease.
22. The method of preparing a grease of claim 20, wherein the grease is a lithium-based grease and the method comprises: mixing and heating part of lubricating base oil and fatty acid in a reaction kettle, heating to 40-90 ℃, adding aqueous solution of silole derivative and lithium hydroxide, heating to remove water, continuously heating to 190-220 ℃ for high-temperature refining, adding the rest lubricating base oil, cooling to 60-120 ℃, and grinding into grease.
23. The method of preparing a grease of claim 20, wherein the grease is a complex aluminum-based grease, and the method comprises: mixing and heating part of base oil, fatty acid and micromolecular acid in a reaction kettle, heating to 40-90 ℃, adding a silole derivative, mixing and heating the other part of lubricating base oil and an aluminum alkoxide compound to 40-100 ℃, adding the mixture into the reaction kettle after the aluminum alkoxide compound is completely dissolved, continuously heating to 190-220 ℃ for high-temperature refining, adding the rest of lubricating base oil, cooling to 60-120 ℃, and grinding into grease.
24. A method for preparing a grease as claimed in any one of claims 20 to 23, wherein the silole derivative is dissolved in a solvent in advance, and the solvent is an aromatic hydrocarbon solvent.
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