JP2003261506A - （メタ）アクリロイルオキシベンゾフェノン類の製造方法 - Google Patents
（メタ）アクリロイルオキシベンゾフェノン類の製造方法Info
- Publication number
- JP2003261506A JP2003261506A JP2002060463A JP2002060463A JP2003261506A JP 2003261506 A JP2003261506 A JP 2003261506A JP 2002060463 A JP2002060463 A JP 2002060463A JP 2002060463 A JP2002060463 A JP 2002060463A JP 2003261506 A JP2003261506 A JP 2003261506A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- formula
- represented
- mol
- group
- 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
Links
- DSTUKHPLWATFCG-UHFFFAOYSA-N (2-benzoylphenyl) prop-2-enoate Chemical class C=CC(=O)OC1=CC=CC=C1C(=O)C1=CC=CC=C1 DSTUKHPLWATFCG-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000000126 substance Substances 0.000 claims abstract description 24
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- YWLKXMKIKWXYSQ-UHFFFAOYSA-N 2-n,6-n-dimethylpyridine-2,6-diamine Chemical compound CNC1=CC=CC(NC)=N1 YWLKXMKIKWXYSQ-UHFFFAOYSA-N 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- 239000012295 chemical reaction liquid Substances 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 abstract description 11
- 230000007797 corrosion Effects 0.000 abstract description 11
- 238000000034 method Methods 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- RYWGNBFHIFRNEP-UHFFFAOYSA-N (4-benzoylphenyl) 2-methylprop-2-enoate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(=O)C1=CC=CC=C1 RYWGNBFHIFRNEP-UHFFFAOYSA-N 0.000 description 13
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 12
- 239000002994 raw material Substances 0.000 description 11
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- -1 acrylic ester Chemical class 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 2
- XGISNRBOYDVKJJ-UHFFFAOYSA-N C=CC(=O)OC1=CC=CC=C1C(=O)C2=CC=CC=C2N Chemical compound C=CC(=O)OC1=CC=CC=C1C(=O)C2=CC=CC=C2N XGISNRBOYDVKJJ-UHFFFAOYSA-N 0.000 description 2
- GYHLEEXZYMYRKC-UHFFFAOYSA-N C=CC(OC(C=CC=C1)=C1C(C(C=CC=C1)=C1Cl)=O)=O Chemical compound C=CC(OC(C=CC=C1)=C1C(C(C=CC=C1)=C1Cl)=O)=O GYHLEEXZYMYRKC-UHFFFAOYSA-N 0.000 description 2
- QZYMFKVDZBACBR-UHFFFAOYSA-N COC1=CC=CC=C1C(=O)C2=CC=CC=C2OC(=O)C=C Chemical compound COC1=CC=CC=C1C(=O)C2=CC=CC=C2OC(=O)C=C QZYMFKVDZBACBR-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YBCNUEIYHGIPNG-UHFFFAOYSA-N [2-(2-methylbenzoyl)phenyl] prop-2-enoate Chemical compound CC1=CC=CC=C1C(=O)C2=CC=CC=C2OC(=O)C=C YBCNUEIYHGIPNG-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- PCNWPKUYKGAUOX-UHFFFAOYSA-N (2-amino-4-hydroxyphenyl)-phenylmethanone Chemical compound NC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 PCNWPKUYKGAUOX-UHFFFAOYSA-N 0.000 description 1
- IIKFGNLMLHVIDC-UHFFFAOYSA-N (2-aminophenyl)-(2-hydroxyphenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1O IIKFGNLMLHVIDC-UHFFFAOYSA-N 0.000 description 1
- SNZLSLXCYUPBDJ-UHFFFAOYSA-N (2-aminophenyl)-(4-hydroxyphenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 SNZLSLXCYUPBDJ-UHFFFAOYSA-N 0.000 description 1
- MOQFYEDUXPHJEQ-UHFFFAOYSA-N (2-benzoyl-5-methoxyphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 MOQFYEDUXPHJEQ-UHFFFAOYSA-N 0.000 description 1
- WLNNTUIWQBQVNI-UHFFFAOYSA-N (2-chloro-4-hydroxyphenyl)-phenylmethanone Chemical compound ClC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 WLNNTUIWQBQVNI-UHFFFAOYSA-N 0.000 description 1
- XKIZYRVSJNWVGM-UHFFFAOYSA-N (2-chlorophenyl)-(2-hydroxyphenyl)methanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1Cl XKIZYRVSJNWVGM-UHFFFAOYSA-N 0.000 description 1
- BFFHEHNJSNFLRF-UHFFFAOYSA-N (2-chlorophenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1Cl BFFHEHNJSNFLRF-UHFFFAOYSA-N 0.000 description 1
- KIZCNUWGIVQQBK-UHFFFAOYSA-N (2-hydroxy-4-methylphenyl)-phenylmethanone Chemical compound OC1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 KIZCNUWGIVQQBK-UHFFFAOYSA-N 0.000 description 1
- FGWBPOZNLQUSTG-UHFFFAOYSA-N (2-hydroxy-4-nitrophenyl)-phenylmethanone Chemical compound OC1=CC([N+]([O-])=O)=CC=C1C(=O)C1=CC=CC=C1 FGWBPOZNLQUSTG-UHFFFAOYSA-N 0.000 description 1
- HSCIDDFNIHSEDR-UHFFFAOYSA-N (2-hydroxyphenyl)-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=CC=C1O HSCIDDFNIHSEDR-UHFFFAOYSA-N 0.000 description 1
- GWAHXRKRPHOSCV-UHFFFAOYSA-N (2-hydroxyphenyl)-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1O GWAHXRKRPHOSCV-UHFFFAOYSA-N 0.000 description 1
- YYFVMWRENLTLDD-UHFFFAOYSA-N (2-hydroxyphenyl)-(2-nitrophenyl)methanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1[N+]([O-])=O YYFVMWRENLTLDD-UHFFFAOYSA-N 0.000 description 1
- YCLQTMVHFMKKJV-UHFFFAOYSA-N (4-amino-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 YCLQTMVHFMKKJV-UHFFFAOYSA-N 0.000 description 1
- ZLUJJCPTVKQVDE-UHFFFAOYSA-N (4-aminophenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(O)C=C1 ZLUJJCPTVKQVDE-UHFFFAOYSA-N 0.000 description 1
- JYFJHKRWGLEWKH-UHFFFAOYSA-N (4-chloro-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 JYFJHKRWGLEWKH-UHFFFAOYSA-N 0.000 description 1
- RUETVLNXAGWCDS-UHFFFAOYSA-N (4-chlorophenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(Cl)C=C1 RUETVLNXAGWCDS-UHFFFAOYSA-N 0.000 description 1
- LZGTVDVVCYUUJP-UHFFFAOYSA-N (4-hydroxy-2-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 LZGTVDVVCYUUJP-UHFFFAOYSA-N 0.000 description 1
- XPCXDJJTFCXJIU-UHFFFAOYSA-N (4-hydroxy-2-methylphenyl)-phenylmethanone Chemical compound CC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 XPCXDJJTFCXJIU-UHFFFAOYSA-N 0.000 description 1
- JSDAKAUGBREMJW-UHFFFAOYSA-N (4-hydroxy-2-nitrophenyl)-phenylmethanone Chemical compound [N+](=O)([O-])C1=C(C(=O)C2=CC=CC=C2)C=CC(=C1)O JSDAKAUGBREMJW-UHFFFAOYSA-N 0.000 description 1
- BKGKCRVOQOWLQA-UHFFFAOYSA-N (4-hydroxyphenyl)-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 BKGKCRVOQOWLQA-UHFFFAOYSA-N 0.000 description 1
- PYLPYSHXUTVYCV-UHFFFAOYSA-N (4-hydroxyphenyl)-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 PYLPYSHXUTVYCV-UHFFFAOYSA-N 0.000 description 1
- VVSIPWIQRLVVEF-UHFFFAOYSA-N (4-hydroxyphenyl)-(2-nitrophenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1[N+]([O-])=O VVSIPWIQRLVVEF-UHFFFAOYSA-N 0.000 description 1
- LGJXZWFPIDESNQ-UHFFFAOYSA-N (4-hydroxyphenyl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(O)C=C1 LGJXZWFPIDESNQ-UHFFFAOYSA-N 0.000 description 1
- HPJMSFQWRMTUHT-UHFFFAOYSA-N (4-hydroxyphenyl)-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(O)C=C1 HPJMSFQWRMTUHT-UHFFFAOYSA-N 0.000 description 1
- ZEYDQRVULMQZIU-UHFFFAOYSA-N (4-hydroxyphenyl)-(4-nitrophenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 ZEYDQRVULMQZIU-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- RYDYANBFFZSCFP-UHFFFAOYSA-N C(C=C)(=O)OC1=C(C=CC=C1)C(=O)C1=CC=C(C=C1)Cl Chemical compound C(C=C)(=O)OC1=C(C=CC=C1)C(=O)C1=CC=C(C=C1)Cl RYDYANBFFZSCFP-UHFFFAOYSA-N 0.000 description 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101000800116 Homo sapiens Thy-1 membrane glycoprotein Proteins 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- 102000003729 Neprilysin Human genes 0.000 description 1
- 108090000028 Neprilysin Proteins 0.000 description 1
- 102100033523 Thy-1 membrane glycoprotein Human genes 0.000 description 1
- DTBGZLQDGPTJIG-UHFFFAOYSA-N [2-(4-methoxybenzoyl)phenyl] prop-2-enoate Chemical compound C(C=C)(=O)OC1=C(C(=O)C2=CC=C(C=C2)OC)C=CC=C1 DTBGZLQDGPTJIG-UHFFFAOYSA-N 0.000 description 1
- CNDGWDKIUVIOET-UHFFFAOYSA-N [2-(4-methylbenzoyl)phenyl] prop-2-enoate Chemical compound CC1=CC=C(C=C1)C(=O)C2=CC=CC=C2OC(=O)C=C CNDGWDKIUVIOET-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| JP2002060463A JP2003261506A (ja) | 2002-03-06 | 2002-03-06 | （メタ）アクリロイルオキシベンゾフェノン類の製造方法 |
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| JP2002060463A JP2003261506A (ja) | 2002-03-06 | 2002-03-06 | （メタ）アクリロイルオキシベンゾフェノン類の製造方法 |
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| JP2003261506A true JP2003261506A (ja) | 2003-09-19 |
| JP2003261506A5 JP2003261506A5 (enExample) | 2005-09-02 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2006096422A1 (en) * | 2005-03-04 | 2006-09-14 | Bausch & Lomb Incorporated | Radiation-absorbing materials, ophthalmic compositions containing same, and method of treating ophthalmic devices |
| DE102008054611A1 (de) | 2008-12-15 | 2010-06-17 | Evonik Röhm Gmbh | Verfahren zur Herstellung von methacrylierten Benzophenonen |
| WO2015049200A1 (de) * | 2013-10-04 | 2015-04-09 | Evonik Röhm Gmbh | Verfahren zur herstellung von methacrylierten benzophenonen |
| CN109971294A (zh) * | 2019-04-03 | 2019-07-05 | 广州五行材料科技有限公司 | 一种自引发的有机/无机杂化材料及其制备方法和应用 |
| WO2019224193A1 (en) | 2018-05-23 | 2019-11-28 | Evonik Röhm Gmbh | Method for preparing keto-functionalized aromatic (meth)acrylates |
| US11512043B2 (en) | 2018-07-26 | 2022-11-29 | Evonik Operations Gmbh | Process for preparing N-methyl(meth)acrylamide |
| US11912648B2 (en) | 2018-07-17 | 2024-02-27 | Evonik Operations Gmbh | Method for preparing C-H acidic (meth)acrylates |
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2002
- 2002-03-06 JP JP2002060463A patent/JP2003261506A/ja active Pending
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| WO2006096422A1 (en) * | 2005-03-04 | 2006-09-14 | Bausch & Lomb Incorporated | Radiation-absorbing materials, ophthalmic compositions containing same, and method of treating ophthalmic devices |
| DE102008054611A1 (de) | 2008-12-15 | 2010-06-17 | Evonik Röhm Gmbh | Verfahren zur Herstellung von methacrylierten Benzophenonen |
| WO2010072479A1 (de) * | 2008-12-15 | 2010-07-01 | Evonik Röhm Gmbh | Verfahren zur herstellung von methacrylierten benzophenonen |
| KR20110094309A (ko) * | 2008-12-15 | 2011-08-23 | 에보니크 룀 게엠베하 | 메타크릴레이트화 벤조페논의 제조 방법 |
| CN102203048A (zh) * | 2008-12-15 | 2011-09-28 | 赢创罗姆有限公司 | 制备甲基丙烯酸化的二苯甲酮的方法 |
| JP2012512216A (ja) * | 2008-12-15 | 2012-05-31 | エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツング | メタクリル化されたベンゾフェノンの製造方法 |
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| AU2009331813A8 (en) * | 2008-12-15 | 2014-07-10 | Evonik Operations Gmbh | Method for producing methacrylated benzophenones |
| RU2536471C2 (ru) * | 2008-12-15 | 2014-12-27 | Эвоник Рем ГмбХ | Способ получения метакрилированных бензофенонов |
| KR101683315B1 (ko) | 2008-12-15 | 2016-12-06 | 에보니크 룀 게엠베하 | 메타크릴레이트화 벤조페논의 제조 방법 |
| DE102013220127A1 (de) | 2013-10-04 | 2015-04-09 | Evonik Röhm Gmbh | Verfahren zur Herstellung von methacrylierten Benzophenonen |
| TWI654176B (zh) | 2013-10-04 | 2019-03-21 | 贏創羅恩有限責任公司 | 製備甲基丙烯酸化之二苯甲酮之方法 |
| KR20160067929A (ko) * | 2013-10-04 | 2016-06-14 | 에보니크 룀 게엠베하 | 메타크릴레이트화된 벤조페논 제조 방법 |
| WO2015049200A1 (de) * | 2013-10-04 | 2015-04-09 | Evonik Röhm Gmbh | Verfahren zur herstellung von methacrylierten benzophenonen |
| JP2016539913A (ja) * | 2013-10-04 | 2016-12-22 | エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツングＥｖｏｎｉｋ Ｒｏｅｈｍ ＧｍｂＨ | メタクリル化ベンゾフェノンの製造方法 |
| US9656941B2 (en) | 2013-10-04 | 2017-05-23 | Evonik Roehm Gmbh | Method for producing methacrylated benzophenones |
| CN105593203B (zh) * | 2013-10-04 | 2018-05-25 | 赢创罗姆有限公司 | 制备甲基丙烯酸化二苯甲酮的方法 |
| CN105593203A (zh) * | 2013-10-04 | 2016-05-18 | 赢创罗姆有限公司 | 制备甲基丙烯酸化二苯甲酮的方法 |
| KR102254784B1 (ko) * | 2013-10-04 | 2021-05-21 | 에보닉 오퍼레이션스 게엠베하 | 메타크릴레이트화된 벤조페논 제조 방법 |
| WO2019224193A1 (en) | 2018-05-23 | 2019-11-28 | Evonik Röhm Gmbh | Method for preparing keto-functionalized aromatic (meth)acrylates |
| US11505520B2 (en) | 2018-05-23 | 2022-11-22 | Evonik Operations Gmbh | Method for preparing keto-functionalized aromatic (meth)acrylates |
| US11912648B2 (en) | 2018-07-17 | 2024-02-27 | Evonik Operations Gmbh | Method for preparing C-H acidic (meth)acrylates |
| US11512043B2 (en) | 2018-07-26 | 2022-11-29 | Evonik Operations Gmbh | Process for preparing N-methyl(meth)acrylamide |
| CN109971294B (zh) * | 2019-04-03 | 2020-11-10 | 广州五行材料科技有限公司 | 一种自引发的有机/无机杂化材料及其制备方法和应用 |
| CN109971294A (zh) * | 2019-04-03 | 2019-07-05 | 广州五行材料科技有限公司 | 一种自引发的有机/无机杂化材料及其制备方法和应用 |
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