CN117186143A - Preparation method of siloxane containing electron withdrawing functional groups - Google Patents
Preparation method of siloxane containing electron withdrawing functional groups Download PDFInfo
- Publication number
- CN117186143A CN117186143A CN202311090321.0A CN202311090321A CN117186143A CN 117186143 A CN117186143 A CN 117186143A CN 202311090321 A CN202311090321 A CN 202311090321A CN 117186143 A CN117186143 A CN 117186143A
- Authority
- CN
- China
- Prior art keywords
- catalyst
- electron withdrawing
- siloxane
- temperature
- ether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 125000000524 functional group Chemical group 0.000 title claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 239000000460 chlorine Substances 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 4
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 238000000746 purification Methods 0.000 claims abstract description 4
- 238000000926 separation method Methods 0.000 claims abstract description 4
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 claims description 17
- 239000005052 trichlorosilane Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 7
- 239000005046 Chlorosilane Substances 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052703 rhodium Inorganic materials 0.000 claims description 4
- 239000010948 rhodium Substances 0.000 claims description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052797 bismuth Inorganic materials 0.000 claims description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 239000011572 manganese Substances 0.000 claims description 3
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 239000012974 tin catalyst Substances 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 6
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000002009 alkene group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 16
- 238000007086 side reaction Methods 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- -1 polysiloxane Polymers 0.000 description 13
- 239000003921 oil Substances 0.000 description 11
- 229920002379 silicone rubber Polymers 0.000 description 9
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000004945 silicone rubber Substances 0.000 description 8
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 7
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 7
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 7
- 229940112669 cuprous oxide Drugs 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 4
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 3
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 3
- 150000001336 alkenes Chemical group 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000011565 manganese chloride Substances 0.000 description 3
- 235000002867 manganese chloride Nutrition 0.000 description 3
- 229940099607 manganese chloride Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- UBMUZYGBAGFCDF-UHFFFAOYSA-N trimethoxy(2-phenylethyl)silane Chemical compound CO[Si](OC)(OC)CCC1=CC=CC=C1 UBMUZYGBAGFCDF-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 2
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 2
- JLDSOYXADOWAKB-UHFFFAOYSA-N aluminium nitrate Chemical compound [Al+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O JLDSOYXADOWAKB-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- JHXKRIRFYBPWGE-UHFFFAOYSA-K bismuth chloride Chemical compound Cl[Bi](Cl)Cl JHXKRIRFYBPWGE-UHFFFAOYSA-K 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007809 chemical reaction catalyst Substances 0.000 description 2
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229920005560 fluorosilicone rubber Polymers 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 238000004255 ion exchange chromatography Methods 0.000 description 2
- OSHOQERNFGVVRH-UHFFFAOYSA-K iron(3+);trifluoromethanesulfonate Chemical compound [Fe+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F OSHOQERNFGVVRH-UHFFFAOYSA-K 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 2
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 2
- QDZRBIRIPNZRSG-UHFFFAOYSA-N titanium nitrate Chemical compound [O-][N+](=O)O[Ti](O[N+]([O-])=O)(O[N+]([O-])=O)O[N+]([O-])=O QDZRBIRIPNZRSG-UHFFFAOYSA-N 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-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
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- FBUZNPORDKVYFD-AATRIKPKSA-N (e)-1-bromohex-1-ene Chemical compound CCCC\C=C\Br FBUZNPORDKVYFD-AATRIKPKSA-N 0.000 description 1
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 1
- ZGMNAIODRDOMEK-UHFFFAOYSA-N 1,1,1-trimethoxypropane Chemical compound CCC(OC)(OC)OC ZGMNAIODRDOMEK-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- QYIGOGBGVKONDY-UHFFFAOYSA-N 1-(2-bromo-5-chlorophenyl)-3-methylpyrazole Chemical compound N1=C(C)C=CN1C1=CC(Cl)=CC=C1Br QYIGOGBGVKONDY-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 1
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
- FGQLGYBGTRHODR-UHFFFAOYSA-N 2,2-diethoxypropane Chemical compound CCOC(C)(C)OCC FGQLGYBGTRHODR-UHFFFAOYSA-N 0.000 description 1
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
- RMGHERXMTMUMMV-UHFFFAOYSA-N 2-methoxypropane Chemical compound COC(C)C RMGHERXMTMUMMV-UHFFFAOYSA-N 0.000 description 1
- HNFSPSWQNZVCTB-UHFFFAOYSA-N 2-methyl-2-propan-2-yloxypropane Chemical compound CC(C)OC(C)(C)C HNFSPSWQNZVCTB-UHFFFAOYSA-N 0.000 description 1
- OLBGECWYBGXCNV-UHFFFAOYSA-N 3-trichlorosilylpropanenitrile Chemical compound Cl[Si](Cl)(Cl)CCC#N OLBGECWYBGXCNV-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- QJMYXHKGEGNLED-UHFFFAOYSA-N 5-(2-hydroxyethylamino)-1h-pyrimidine-2,4-dione Chemical compound OCCNC1=CNC(=O)NC1=O QJMYXHKGEGNLED-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 239000005955 Ferric phosphate Substances 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- MLHOXUWWKVQEJB-UHFFFAOYSA-N Propyleneglycol diacetate Chemical compound CC(=O)OC(C)COC(C)=O MLHOXUWWKVQEJB-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- INNSZZHSFSFSGS-UHFFFAOYSA-N acetic acid;titanium Chemical compound [Ti].CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O INNSZZHSFSFSGS-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- BPGDAMSIGCZZLK-UHFFFAOYSA-N acetyloxymethyl acetate Chemical compound CC(=O)OCOC(C)=O BPGDAMSIGCZZLK-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940001007 aluminium phosphate Drugs 0.000 description 1
- COOGPNLGKIHLSK-UHFFFAOYSA-N aluminium sulfide Chemical compound [Al+3].[Al+3].[S-2].[S-2].[S-2] COOGPNLGKIHLSK-UHFFFAOYSA-N 0.000 description 1
- 239000001164 aluminium sulphate Substances 0.000 description 1
- 235000011128 aluminium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FKOASGGZYSYPBI-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)alumanyl trifluoromethanesulfonate Chemical compound [Al+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F FKOASGGZYSYPBI-UHFFFAOYSA-K 0.000 description 1
- NYENCOMLZDQKNH-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)bismuthanyl trifluoromethanesulfonate Chemical compound [Bi+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F NYENCOMLZDQKNH-UHFFFAOYSA-K 0.000 description 1
- 229940036348 bismuth carbonate Drugs 0.000 description 1
- 229910000416 bismuth oxide Inorganic materials 0.000 description 1
- 229910000380 bismuth sulfate Inorganic materials 0.000 description 1
- TXKAQZRUJUNDHI-UHFFFAOYSA-K bismuth tribromide Chemical compound Br[Bi](Br)Br TXKAQZRUJUNDHI-UHFFFAOYSA-K 0.000 description 1
- SFOQXWSZZPWNCL-UHFFFAOYSA-K bismuth;phosphate Chemical compound [Bi+3].[O-]P([O-])([O-])=O SFOQXWSZZPWNCL-UHFFFAOYSA-K 0.000 description 1
- BRCWHGIUHLWZBK-UHFFFAOYSA-K bismuth;trifluoride Chemical compound F[Bi](F)F BRCWHGIUHLWZBK-UHFFFAOYSA-K 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- NNLOHLDVJGPUFR-UHFFFAOYSA-L calcium;3,4,5,6-tetrahydroxy-2-oxohexanoate Chemical compound [Ca+2].OCC(O)C(O)C(O)C(=O)C([O-])=O.OCC(O)C(O)C(O)C(=O)C([O-])=O NNLOHLDVJGPUFR-UHFFFAOYSA-L 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- YFPCLQKFNXUAAK-UHFFFAOYSA-N cyclopentyl acetate Chemical compound CC(=O)OC1CCCC1 YFPCLQKFNXUAAK-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- WCOATMADISNSBV-UHFFFAOYSA-K diacetyloxyalumanyl acetate Chemical compound [Al+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WCOATMADISNSBV-UHFFFAOYSA-K 0.000 description 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 1
- GMZOPRQQINFLPQ-UHFFFAOYSA-H dibismuth;tricarbonate Chemical compound [Bi+3].[Bi+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O GMZOPRQQINFLPQ-UHFFFAOYSA-H 0.000 description 1
- BEQZMQXCOWIHRY-UHFFFAOYSA-H dibismuth;trisulfate Chemical compound [Bi+3].[Bi+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BEQZMQXCOWIHRY-UHFFFAOYSA-H 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- UBPGILLNMDGSDS-UHFFFAOYSA-N diethylene glycol diacetate Chemical compound CC(=O)OCCOCCOC(C)=O UBPGILLNMDGSDS-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GJJASJCGLOUWAC-UHFFFAOYSA-N ethoxycyclohexane Chemical compound CCOC1CCCCC1 GJJASJCGLOUWAC-UHFFFAOYSA-N 0.000 description 1
- AOWTYVFGMCEIRN-UHFFFAOYSA-N ethoxycyclopentane Chemical compound CCOC1CCCC1 AOWTYVFGMCEIRN-UHFFFAOYSA-N 0.000 description 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 229940032958 ferric phosphate Drugs 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- KAEAMHPPLLJBKF-UHFFFAOYSA-N iron(3+) sulfide Chemical compound [S-2].[S-2].[S-2].[Fe+3].[Fe+3] KAEAMHPPLLJBKF-UHFFFAOYSA-N 0.000 description 1
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 1
- YPJCVYYCWSFGRM-UHFFFAOYSA-H iron(3+);tricarbonate Chemical compound [Fe+3].[Fe+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O YPJCVYYCWSFGRM-UHFFFAOYSA-H 0.000 description 1
- HEJPGFRXUXOTGM-UHFFFAOYSA-K iron(3+);triiodide Chemical compound [Fe+3].[I-].[I-].[I-] HEJPGFRXUXOTGM-UHFFFAOYSA-K 0.000 description 1
- 229910000399 iron(III) phosphate Inorganic materials 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- SHXXPRJOPFJRHA-UHFFFAOYSA-K iron(iii) fluoride Chemical compound F[Fe](F)F SHXXPRJOPFJRHA-UHFFFAOYSA-K 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GHDIHPNJQVDFBL-UHFFFAOYSA-N methoxycyclohexane Chemical compound COC1CCCCC1 GHDIHPNJQVDFBL-UHFFFAOYSA-N 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- DCKVFVYPWDKYDN-UHFFFAOYSA-L oxygen(2-);titanium(4+);sulfate Chemical compound [O-2].[Ti+4].[O-]S([O-])(=O)=O DCKVFVYPWDKYDN-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
- KTEDZFORYFITAF-UHFFFAOYSA-K rhodium(3+);trihydroxide Chemical compound [OH-].[OH-].[OH-].[Rh+3] KTEDZFORYFITAF-UHFFFAOYSA-K 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000004590 silicone sealant Substances 0.000 description 1
- LCHWKMAWSZDQRD-UHFFFAOYSA-N silylformonitrile Chemical compound [SiH3]C#N LCHWKMAWSZDQRD-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- RCYJPSGNXVLIBO-UHFFFAOYSA-N sulfanylidenetitanium Chemical compound [S].[Ti] RCYJPSGNXVLIBO-UHFFFAOYSA-N 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- HIAIVILTZQDDNY-UHFFFAOYSA-J tin(4+);trifluoromethanesulfonate Chemical compound [Sn+4].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HIAIVILTZQDDNY-UHFFFAOYSA-J 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- QPBYLOWPSRZOFX-UHFFFAOYSA-J tin(iv) iodide Chemical compound I[Sn](I)(I)I QPBYLOWPSRZOFX-UHFFFAOYSA-J 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910000348 titanium sulfate Inorganic materials 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 description 1
- NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 description 1
- IMIUDLLSPLZPNS-UHFFFAOYSA-J titanium(4+) trifluoromethanesulfonate Chemical compound [Ti+4].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F IMIUDLLSPLZPNS-UHFFFAOYSA-J 0.000 description 1
- FOZHTJJTSSSURD-UHFFFAOYSA-J titanium(4+);dicarbonate Chemical compound [Ti+4].[O-]C([O-])=O.[O-]C([O-])=O FOZHTJJTSSSURD-UHFFFAOYSA-J 0.000 description 1
- JUWGUJSXVOBPHP-UHFFFAOYSA-B titanium(4+);tetraphosphate Chemical compound [Ti+4].[Ti+4].[Ti+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O JUWGUJSXVOBPHP-UHFFFAOYSA-B 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- KOECRLKKXSXCPB-UHFFFAOYSA-K triiodobismuthane Chemical compound I[Bi](I)I KOECRLKKXSXCPB-UHFFFAOYSA-K 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Abstract
The application relates to the technical field of C07F7/18, in particular to a preparation method of siloxane containing electron withdrawing functional groups, which comprises the following steps: reacting the compound (I) with an ether substance in the presence of a catalyst to obtain siloxane; wherein the compound (I) has the structure ofThe siloxane has the structure ofn is any integer from 1 to 5, R 1 Is any one of nitro, cyano, fluorine, chlorine, bromine, iodine, alkynyl, aryl and acetyl, R 2 Is C 1‑5 Alkyl or acetyl. The preparation method disclosed by the application is simple to operate, mild in reaction conditions, good in intermediate stability, not easy to cause side reaction, and simple in product separation and purification.
Description
Technical Field
The application relates to the technical field of C07F7/18, in particular to a preparation method of siloxane containing electron withdrawing functional groups.
Background
The siloxane containing electron withdrawing functional groups is a common silane coupling agent, is an important intermediate for preparing amino propyl trimethoxy silane (HP-540), and is also high-performance oil-resistant silicone sealant. The traditional dimethyl silicone rubber has poor oil resistance, after the silicone rubber is immersed in oil, oil substances can permeate the silicone rubber and act on molecular chains to diffuse mutually to destroy a network structure and generate a swelling effect, and meanwhile, some soluble additives are dissolved to change the network structure, so that the performance of the silicone rubber is poor. In order to make up for the deficiency and maintain other excellent performances, students at home and abroad have made many related researches. Mainly from the following aspects. (1) grafting modification, and introducing polar groups. The fluorosilicone rubber not only has a plurality of excellent performances of the traditional silicone rubber, but also has outstanding oil resistance, but the synthesis process is difficult to control, and the cost is high, so that the fluorosilicone rubber is difficult to popularize and apply. The electron-withdrawing functional group is introduced as a hot spot in recent researches, and the electron-withdrawing functional group modified polydimethyl polysiloxane is novel heat-resistant and oil-resistant silicone rubber, has good stability to common oil, solvent oil and fuel, and can be used at the temperature of-70-260 ℃. (2) Blending modification, and blending with other rubber with good oil resistance to obtain the blending rubber. Currently, in many research systems, common materials that improve the oil resistance of silicone rubber are acrylate rubber (ACM), fluororubber (FKM), and ethylene-vinyl acetate copolymers of the rubber (EVM) and plastic (EVA) type. However, silicone rubber is generally poor in compatibility with the above classes and phase separation is liable to occur. (3) The requirements on raw materials are high, for example, the low molecular weight silicon rubber is selected, and zinc oxide, cerium oxide and the like are selected, so that the oil resistance can be improved to a certain extent.
CN201911409954.7 proposes a preparation method of cyano silane: under the vacuum of-0.1 MPa, dropping methanol, reacting with 2-cyanoethyl trichlorosilane, and absorbing the generated HCl by alkali liquor to obtain the product. However, in the reaction process, a large amount of HCl gas is generated to react with raw material alcohol to generate water, so that not only can raw material chlorosilane be hydrolyzed, but also target product alkoxysilane is initiated to be hydrolyzed, and a large amount of powder is generated in the reaction process; it is also difficult to avoid the addition of methanol to cyano to form imine byproducts. In addition, the HCl produced has a very high solubility in the alkoxysilane of the final product, which leads to increased difficulties in post-reaction treatment and increased production costs. And the alkali liquor is used for removing acid to finally obtain the alkoxy silane with low acid value, and the reaction process and the preparation cost are increased.
Therefore, it is desirable to provide a preparation method that is simple to operate, low in cost, and free of HCl gas generation.
Disclosure of Invention
For the purpose ofThe first aspect of the present application provides a method for preparing a siloxane containing an electron withdrawing functional group, comprising: reacting the compound (I) with an ether or ester substance in the presence of a catalyst to obtain siloxane; wherein the compound (I) has the structure ofThe siloxane has the structure->n is any integer from 1 to 5, R 1 Is any one of nitro, cyano, fluorine, chlorine, bromine, iodine, alkynyl, aryl and acetyl, R 2 Is C 1-5 Alkyl or acetyl.
C in the application 1-5 Examples of the alkyl group include methyl, ethyl, propyl, isopropyl, and n-butyl.
In one embodiment, the siloxanes obtained may be exemplified by
Etc.
In one embodiment, the catalyst is selected from one or more of palladium catalyst, platinum catalyst, rhodium catalyst, ruthenium catalyst, cobalt catalyst, iron catalyst, manganese catalyst, bismuth catalyst, aluminum catalyst, zinc catalyst, titanium catalyst, tin catalyst.
Preferably, the palladium catalyst is selected from one or more of tris (dibenzylideneacetone) dipalladium, palladium acetate, (tetra) triphenylphosphine palladium, 1' -bis-diphenylphosphine ferrocene palladium dichloride.
Preferably, the platinum catalyst is selected from one or more of platinum chloride, platinum oxide, chloroplatinic acid, and metallic platinum.
Preferably, the rhodium catalyst is selected from one or more of rhodium chloride, rhodium tetrafluoroborate, rhodium acetate and rhodium metal.
Preferably, the ruthenium catalyst is selected from one or more of rhodium hydroxide, rhodium chloride and metallic ruthenium.
Preferably, the cobalt catalyst is selected from one or more of cobalt acetate, cobalt oxide and metallic cobalt.
Preferably, the iron catalyst is selected from one or more of ferric chloride, ferric bromide, ferric iodide, ferric oxide, ferric triflate, ferric sulfate, ferric nitrate, ferric carbonate, ferric phosphate, ferric acetate, ferric sulfide, ferric fluoride, and the corresponding ferrous salts.
Preferably, the manganese catalyst is selected from one or more of manganese chloride, manganese oxide and manganese metal.
Preferably, the bismuth catalyst is selected from one or more of bismuth chloride, bismuth bromide, bismuth iodide, bismuth oxide, bismuth triflate, bismuth sulfate, bismuth nitrate, bismuth carbonate, bismuth phosphate, bismuth acetate, bismuth sulfide, bismuth fluoride.
Preferably, the aluminium catalyst is selected from one or more of aluminium chloride, aluminium bromide, aluminium iodide, aluminium oxide, aluminium triflate, aluminium sulphate, aluminium nitrate, aluminium carbonate, aluminium phosphate, aluminium acetate, aluminium sulphide, aluminium fluoride.
Preferably, the zinc catalyst is selected from one or more of zinc chloride, zinc bromide, zinc iodide, zinc oxide, zinc triflate, zinc sulfate, zinc nitrate, zinc carbonate, zinc phosphate, zinc acetate, zinc sulfide, zinc fluoride.
Preferably, the titanium catalyst is selected from one or more of titanium chloride, titanium bromide, titanium iodide, titanium oxide, titanium triflate, titanium sulfate, titanium nitrate, titanium carbonate, titanium phosphate, titanium acetate, titanium sulfide, titanium fluoride.
Preferably, the tin catalyst is selected from one or more of tin chloride, tin bromide, tin iodide, tin oxide, tin triflate.
In one embodiment, the molar ratio of compound (I), catalyst, ether or ester is 1 (0.001-0.1): (4-10), preferably 1:0.1:5.
In one embodiment, the reaction temperature is 0 to 150 ℃, preferably 0 to 110 ℃, and examples thereof include 0 ℃,5 ℃, 15 ℃, 20 ℃, 25 ℃, 40 ℃, 45 ℃, 50 ℃, 60 ℃, 70 ℃, 80 ℃, 90 ℃, 100 ℃, 110 ℃, 120 ℃, 130 ℃, 140 ℃, 150 ℃, and the like.
In one embodiment, a method for preparing a siloxane containing electron withdrawing functionality comprises: adding a catalyst and an ether or ester substance into a reaction container, and performing a reaction by adopting a program temperature control under the protection of inert gas, namely: cooling to 0 ℃, dropwise adding the compound (I) at a controlled temperature of 0-5 ℃, preserving heat for 0.5-1.5h at 0-5 ℃ after the dropwise adding, and preserving heat for 10-12h after the temperature is raised to 25-150 ℃ to obtain siloxane, wherein the temperature of the preserved heat after the temperature is raised is preferably 25-110 ℃.
When R is 2 Is C 1-5 In the case of alkyl radicals, the ether or ester species are selected from C 2-5 Such as one or more of alkyl isopropyl ether, alkyl n-butyl ether, alkyl cyclopentyl ether, alkyl cyclohexyl ether, alkyl phenyl ether, glycol ether, orthoformate, orthoacetate, orthopropionate, alkoxymethane, alkoxyethane, alkoxypropane.
Alkyl carbon number and R in ether material 2 The alkyl groups have the same carbon number. For example, when R 2 In the case of methyl, the ether or ester is selected from one or more of methyl isopropyl ether, methyl n-butyl ether, methyl tert-butyl ether, methyl cyclopentyl ether, methyl cyclohexyl ether, methyl phenyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, trimethyl orthoformate, trimethyl orthoacetate, trimethyl orthopropionate, dimethoxymethane, dimethoxyethane and dimethoxypropane. When R is 2 In the case of ethyl, the ether material is selected from one or more of diethyl ether, ethyl isopropyl ether, ethyl n-butyl ether, ethyl tert-butyl ether, ethyl cyclopentyl ether, ethyl cyclohexyl ether, ethyl phenyl ether, ethylene glycol diethyl ether, diethylene glycol diethyl ether, triethyl orthoformate, triethyl orthoacetate, triethyl orthopropionate, diethoxymethane, diethoxyethane and diethoxypropane.
When R is 2 In the case of acetyl, the ether or ester is selected from one or more of ethyl acetate, isopropyl acetate, n-butyl acetate, t-butyl acetate, cyclopentyl acetate, cyclohexyl acetate, phenyl acetate, ethylene glycol diacetate, diethylene glycol diacetate, methylene diacetate, ethylene diacetate and propylene diacetate.
In the preparation process of the siloxanes according to the application, after the reaction has been completed, the person skilled in the art can carry out conventional rectification operations.
In one embodiment, the process for preparing compound (I) can be referred to in the literature (Organometallics, 1989,8,549-550), and comprises the following main steps: and (3) reacting the trichlorosilane with electron-withdrawing alkane containing terminal alkene under the conditions of cuprous oxide and tetramethyl ethylenediamine, concentrating and distilling to obtain the compound (I).
In a preferred embodiment, the process for the preparation of compound (I) comprises: adding cuprous oxide and tetramethyl ethylenediamine into a reaction vessel, controlling the temperature to be 0-5 ℃ under the protection of inert gas, adding trichlorosilane and electron-withdrawing alkane containing terminal alkene, heating to 25 ℃ after heat preservation for 1-3 hours, continuously preserving heat for 1-3 hours, and obtaining the compound (I) through reduced pressure distillation.
Preferably, the molar ratio of the trichlorosilane to the terminal alkene-containing electron withdrawing alkane is 1:1.
Preferably, the molar ratio of cuprous oxide, tetramethyl ethylenediamine and trichlorosilane is 0.15: (0.3-0.5): 1, more preferably 0.15:0.45:1.
Compared with the prior art, the application has the following beneficial effects:
(1) The preparation method of the siloxane containing the electron withdrawing functional group solves the problems of high risk, high difficulty in product separation and purification, harsh reaction conditions and the like in the traditional synthesis method;
(2) In the preparation method, the dropping temperature of the compound (I) is controlled to be 0-5 ℃, then the temperature is raised again for reaction after the reaction is carried out for a period of time at 0-5 ℃, and the yield of the obtained target product is high;
(3) The application can continuously improve the yield of the target product by regulating and controlling the catalyst and the ether or ester substances;
(4) According to the application, through the reaction of the compound (I) and the ether substance, the generation of HCl caused by the alcoholysis reaction of chlorosilane and alcohol is avoided, and the method not only avoids the hydrolysis of a target product, but also reduces the cost;
(5) The preparation method disclosed by the application is simple to operate, mild in reaction conditions, good in intermediate stability, not easy to cause side reaction, and simple in product separation and purification.
Detailed Description
The present application is illustrated by the following specific embodiments, but is not limited to the specific examples given below.
Examples
The central control analysis was determined by gas chromatography. The product was measured by gas chromatography, moisture meter, ion chromatography and colorimeter.
The gas chromatography was performed using HP-5 from Shimadzu corporation, 30 m.times.0.32 mm.times.0.25 μm as a column, and the ion chromatography was performed using SH-AC-4 from Siemens Fed corporation, 250 mm.times.4.6 mm; the guard column SH-AG-4, 50mm×4.6mm; the suppressor shi-a-5 was analyzed using the conventional method of the kaleidoscope company, and the colorimeter was analyzed using the conventional method of the hash company.
Example 1
Example 1 provides a method for preparing (2-phenylethyl) trimethoxy silane by using styrene and trichlorosilane as raw materials and manganese chloride as a catalyst, wherein the synthesis reaction formula is as follows:
the preparation steps of the (2-phenylethyl) trimethoxysilane are as follows:
21.45g of cuprous oxide and 52.2g of tetramethyl ethylenediamine are accurately weighed, cooled to 0 ℃ under the protection of nitrogen, 135.5g of trichlorosilane (purity 99%, 1 mol) and 104g of styrene are weighed, uniformly mixed, added into a 250ml constant pressure dropping funnel, slowly dropped into a reaction bottle, the temperature is controlled to be 0-5 ℃, the dropping is carried out for 4 hours, the temperature is kept for 2 hours, the temperature is slowly raised to room temperature, the temperature is kept for 2 hours, and 215.6g of intermediate is obtained through reduced pressure distillation.
11.6g of manganese chloride and 400g of methyl tert-butyl ether (MTBE) are added into a 1000ml four-mouth bottle, cooled to 0 ℃ under the protection of nitrogen, 215.6g of intermediate is added into a constant pressure dropping funnel, slowly dropped into a reaction bottle, the temperature is controlled to be 0-5 ℃, the drop is carried out for 2 hours, the temperature is kept for 1 hour, the temperature is slowly raised to room temperature, the temperature is kept for 10 hours, chloride ions are 18670ppm, after the decompression and desolventization, the colorless transparent liquid (14) is obtained by rectification, the purity of GC is 99.3wt%, and the yield is 84.2wt%. The chloride ion content was 10ppm.
Example 2
Example 2 provides a process for the preparation of (4-cyanobutyl) triacetoxysilane starting from pentenenitrile and trichlorosilane, with cobalt chloride as catalyst, the synthesis reaction being as follows:
the preparation steps of the (2-phenylethyl) trimethoxysilane are as follows:
21.45g of cuprous oxide and 52.2g of tetramethyl ethylenediamine are accurately weighed, cooled to 0 ℃ under the protection of nitrogen in a 250ml four-neck flask, 135.5g of trichlorosilane (purity 99%, 1 mol) and 81g of pentenenitrile are weighed, uniformly mixed, added into a 250ml constant-pressure dropping funnel, slowly dropped into a reaction bottle, the temperature is controlled to be 0-5 ℃, the dropping time is 4 hours, the temperature is kept for 2 hours, the temperature is slowly raised to room temperature, the temperature is kept for 2 hours, and 193.6g of intermediate is obtained through reduced pressure distillation.
Adding 1.17g of cobalt chloride and 533g of methyl acetate into a 1000ml four-mouth bottle, cooling to 0 ℃ under the protection of nitrogen, adding 193.6g of intermediate into a constant pressure dropping funnel, slowly dropping into a reaction bottle, controlling the temperature to be 0-5 ℃, dropping for 2 hours, preserving heat for 1 hour, slowly raising the temperature to 50 ℃, preserving heat for 10 hours, keeping the temperature for 23120ppm of chloride ion, decompressing and desolventizing, rectifying to obtain 232.5g of colorless transparent liquid with the GC purity of 99.0wt% and the yield of 81.0wt%. The chloride ion content was 11ppm.
Example 3
Example 3 provides a method for preparing (2-butanone group) triethoxysilane by using methyl acrylate and trichlorosilane as raw materials and ruthenium chloride as a catalyst, wherein the synthesis reaction formula is as follows:
the preparation steps of the (2-butanone group) triethoxysilane are as follows:
21.45g of cuprous oxide and 52.2g of tetramethyl ethylenediamine are accurately weighed, cooled to 0 ℃ under the protection of nitrogen, 135.5g of trichlorosilane (purity 99%, 1 mol) and 86g of methyl acrylate are weighed, uniformly mixed, added into a 250ml constant-pressure dropping funnel, slowly dropped into a reaction bottle, the temperature is controlled to be 0-5 ℃, the dropping time is 4 hours, the temperature is kept for 2 hours, the temperature is slowly raised to room temperature, the temperature is kept for 2 hours, and 183.4g of intermediate is obtained through reduced pressure distillation.
0.19g of anhydrous ruthenium chloride and 918g of ethyl tertiary butyl ether are added into a 2000ml four-mouth bottle, cooled to 0 ℃ under the protection of nitrogen, 183.4g of intermediate is added into a constant pressure dropping funnel, slowly dropped into a reaction bottle, the temperature is controlled between 0 ℃ and 5 ℃, the drop is carried out for 2 hours, the temperature is kept for 1 hour, the temperature is slowly raised to 70 ℃, the temperature is kept for 10 hours, chlorine ions 16630ppm are decompressed and desolventized, and colorless transparent liquid (2) 184.2g with GC purity of 99.1wt% and yield of 78.7wt% is obtained by rectification. The chloride ion content was 11ppm.
Example 4
Example 4 provides a method for preparing (2-butanone group) triethoxysilane by using methyl acrylate and trichlorosilane as raw materials and palladium chloride as a catalyst, wherein the synthesis reaction formula is as follows:
the preparation steps of the (2-butanone group) triethoxysilane are as follows:
21.45g of cuprous oxide and 52.2g of tetramethyl ethylenediamine are accurately weighed, cooled to 0 ℃ under the protection of nitrogen, 135.5g of trichlorosilane (purity 99%, 1 mol) and 86g of methyl acrylate are weighed, uniformly mixed, added into a 250ml constant-pressure dropping funnel, slowly dropped into a reaction bottle, the temperature is controlled to be 0-5 ℃, the dropping time is 4 hours, the temperature is kept for 2 hours, the temperature is slowly raised to room temperature, the temperature is kept for 2 hours, and 181.2g of intermediate is obtained through reduced pressure distillation.
16.0g of anhydrous palladium chloride and 400g of ethyl tertiary butyl ether are added into a 1000ml four-mouth bottle, cooled to 0 ℃ under the protection of nitrogen, 181.2g of intermediate is added into a constant pressure dropping funnel, slowly dropped into a reaction bottle, the temperature is controlled between 0 ℃ and 5 ℃, the drop is carried out for 2 hours, the temperature is kept for 1 hour, the temperature is slowly increased to 60 ℃, the temperature is kept for 10 hours, chloride ions are 17640ppm, after decompression and desolventizing, 187.7g of colorless transparent liquid (2) is obtained by rectification, the GC purity is 98.9wt%, and the yield is 80.2wt%. The chloride ion content was 12ppm.
Example 5
Example 5 provides a process for the preparation of nitroethylene and trichlorosilane starting materials, the process conditions being substantially the same as those of example 1, except that the second reaction catalyst was changed to ferric triflate, and the corresponding compound was obtained in a yield of 71.3wt%. GC purity was 98.1wt% and chloride ion was 10ppm.
Example 6
Example 6 provides a process for the preparation of 1-bromohexene and trichlorosilane starting from essentially the same conditions as in example 1, except that the second reaction catalyst was replaced by zinc nitrate, and the corresponding compound was obtained in 80.2wt% yield. GC purity was 98.7wt% and chloride ion was 12ppm.
Example 7
Example 8 provides a process for preparing styrene and trichlorosilane as starting materials under substantially the same conditions as in example 1, except that the second step of reaction was changed to chloroplatinic acid, methyl tertiary ether was changed to isopropyl tertiary butyl ether, the temperature of the resulting mixture was still 0-5 ℃, the reaction temperature was kept at 110 ℃, and the corresponding compound was obtained in the same manner, with a yield of 69.3wt%. GC purity was 98.0wt% and chloride ion was 10ppm.
Example 8
Example 8 provides a process for the preparation of styrene and trichlorosilane starting materials under substantially the same conditions as in example 1, except that the catalyst of the second reaction step was changed to bismuth chloride, methyl tertiary ether was changed to n-amyl ether, the reaction temperature was 120 ℃, and the corresponding compound was obtained in a yield of 46.1wt%. GC purity 95.2wt% and chloride ion 18ppm.
Claims (10)
1. The preparation method of the siloxane containing the electron withdrawing functional group is characterized by comprising the step of reacting chlorosilane containing the electron withdrawing functional group with a non-aqueous reagent under the action of a catalyst, wherein the non-aqueous reagent is an ether or ester substance.
2. The method for producing an electron withdrawing-functional group-containing siloxane according to claim 1, wherein the structure of the electron withdrawing-functional group-containing siloxane is:n is any integer from 1 to 5, R 1 Is any one of nitro, cyano, fluorine, chlorine, bromine, iodine, alkynyl, aryl and acetyl, R 2 Is C 1-5 Alkyl or acetyl.
3. The method for producing an electron withdrawing group-containing siloxane according to any one of claims 1 to 2, wherein the electron withdrawing group-containing chlorosilane structure is: :
n is any integer from 1 to 5, R 1 Is any one of nitro, cyano, fluorine, chlorine, bromine, iodine, alkynyl, aryl and acetyl.
4. A method for preparing a siloxane containing an electron withdrawing functionality according to any one of claims 1 to 3, wherein said catalyst is one or more of palladium catalyst, platinum catalyst, rhodium catalyst, ruthenium catalyst, cobalt catalyst, iron catalyst, manganese catalyst, bismuth catalyst, aluminum catalyst, zinc catalyst, titanium catalyst, tin catalyst.
5. The method for producing an electron withdrawing group-containing siloxane according to any one of claims 1 to 4, wherein the molar ratio of the electron withdrawing group-containing chlorosilane, catalyst, ether or ester is 1 (0.001 to 0.1): (4-10), preferably 1:0.1:5.
6. The method for producing an electron withdrawing-functional siloxane according to any one of claims 1 to 5, wherein the reaction temperature is 0 to 110 ℃.
7. The method for preparing a siloxane containing electron withdrawing functionality according to claim 6, wherein the reaction process adopts a programmed temperature control, namely comprising: adding a catalyst and ether or ester substances into a reaction container, cooling to 0 ℃ under the protection of inert gas, then dropwise adding chlorosilane containing electron-withdrawing functional groups at the controlled temperature of 0-5 ℃, after the dropwise adding, preserving the heat for 0.5-1.5h at the temperature of 0-5 ℃, and preserving the heat for 10-12h after the temperature is raised to 25-110 ℃ to obtain siloxane.
8. The method according to any one of claims 1 to 7, wherein the separation and purification step is carried out after the completion of the reaction step.
9. The method for producing an electron withdrawing group-containing siloxane according to any one of claims 1 to 8, wherein the electron withdrawing group-containing chlorosilane is obtained by reacting trichlorosilane with an electron withdrawing alkane containing terminal alkene under the condition of a catalyst.
10. A siloxane containing electron withdrawing functionality, wherein the siloxane is prepared by the preparation method of any one of claims 1-9, and the content of chloride ions in the siloxane is below 20ppm, preferably below 15 ppm.
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