DE112005000464T5 - Verfahren zum Herstellen von Hydroxystyrolen und acetylierten Derivaten davon - Google Patents
Verfahren zum Herstellen von Hydroxystyrolen und acetylierten Derivaten davon Download PDFInfo
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- DE112005000464T5 DE112005000464T5 DE112005000464T DE112005000464T DE112005000464T5 DE 112005000464 T5 DE112005000464 T5 DE 112005000464T5 DE 112005000464 T DE112005000464 T DE 112005000464T DE 112005000464 T DE112005000464 T DE 112005000464T DE 112005000464 T5 DE112005000464 T5 DE 112005000464T5
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- 238000000034 method Methods 0.000 title claims abstract description 104
- 238000002360 preparation method Methods 0.000 title description 24
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical class OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 title description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 52
- 238000006114 decarboxylation reaction Methods 0.000 claims abstract description 52
- 239000000758 substrate Substances 0.000 claims abstract description 52
- 239000011541 reaction mixture Substances 0.000 claims abstract description 42
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 239000003495 polar organic solvent Substances 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 6
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 230000000911 decarboxylating effect Effects 0.000 claims abstract 2
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims description 63
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 56
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 43
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 36
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 claims description 35
- 238000006116 polymerization reaction Methods 0.000 claims description 33
- 239000003112 inhibitor Substances 0.000 claims description 28
- 235000011056 potassium acetate Nutrition 0.000 claims description 28
- JAMNSIXSLVPNLC-UHFFFAOYSA-N (4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1 JAMNSIXSLVPNLC-UHFFFAOYSA-N 0.000 claims description 15
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 14
- 239000012345 acetylating agent Substances 0.000 claims description 14
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- -1 N-oxyl (nitroxide) Chemical class 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 claims description 9
- 239000003586 protic polar solvent Substances 0.000 claims description 9
- FBTSUTGMWBDAAC-UHFFFAOYSA-N 3,4-Dihydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1O FBTSUTGMWBDAAC-UHFFFAOYSA-N 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 235000004883 caffeic acid Nutrition 0.000 claims description 7
- 229940074360 caffeic acid Drugs 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 claims description 6
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000011929 di(propylene glycol) methyl ether Substances 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 5
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 5
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 claims description 5
- 235000001785 ferulic acid Nutrition 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- BGDWDFVUSUCDHI-UHFFFAOYSA-N (2-acetyloxy-4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1OC(C)=O BGDWDFVUSUCDHI-UHFFFAOYSA-N 0.000 claims description 4
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 claims description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 4
- YOMSJEATGXXYPX-UHFFFAOYSA-N 2-methoxy-4-vinylphenol Chemical compound COC1=CC(C=C)=CC=C1O YOMSJEATGXXYPX-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- QHJGZUSJKGVMTF-UHFFFAOYSA-N canolol Chemical compound COC1=CC(C=C)=CC(OC)=C1O QHJGZUSJKGVMTF-UHFFFAOYSA-N 0.000 claims description 4
- 229940114124 ferulic acid Drugs 0.000 claims description 4
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- PCMORTLOPMLEFB-ONEGZZNKSA-N sinapic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-ONEGZZNKSA-N 0.000 claims description 4
- PCMORTLOPMLEFB-UHFFFAOYSA-N sinapinic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-UHFFFAOYSA-N 0.000 claims description 4
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 claims description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 3
- BOBATFKNMFWLFG-UHFFFAOYSA-N 2-amino-2-cyano-n-methylacetamide Chemical compound CNC(=O)C(N)C#N BOBATFKNMFWLFG-UHFFFAOYSA-N 0.000 claims description 3
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 claims description 3
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- 159000000021 acetate salts Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- SXPLGYBFGPYAHS-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 SXPLGYBFGPYAHS-UHFFFAOYSA-N 0.000 claims description 3
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 3
- 239000000395 magnesium oxide Substances 0.000 claims description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- PMOWTIHVNWZYFI-UHFFFAOYSA-N o-Coumaric acid Natural products OC(=O)C=CC1=CC=CC=C1O PMOWTIHVNWZYFI-UHFFFAOYSA-N 0.000 claims description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 3
- 229950000688 phenothiazine Drugs 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
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- AFVLVVWMAFSXCK-UHFFFAOYSA-N α-cyano-4-hydroxycinnamic acid Chemical compound OC(=O)C(C#N)=CC1=CC=C(O)C=C1 AFVLVVWMAFSXCK-UHFFFAOYSA-N 0.000 claims description 3
- WRPYDXWBHXAKPT-UHFFFAOYSA-N (2-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C=C WRPYDXWBHXAKPT-UHFFFAOYSA-N 0.000 claims description 2
- PAGUNWMOLOQVJA-UHFFFAOYSA-N (4-ethenyl-2,6-dimethoxyphenyl) acetate Chemical compound COC1=CC(C=C)=CC(OC)=C1OC(C)=O PAGUNWMOLOQVJA-UHFFFAOYSA-N 0.000 claims description 2
- FTBUUBIPWKNBRF-UHFFFAOYSA-N (4-ethenyl-2-methoxyphenyl) acetate Chemical compound COC1=CC(C=C)=CC=C1OC(C)=O FTBUUBIPWKNBRF-UHFFFAOYSA-N 0.000 claims description 2
- DZKAISAHHPTWNO-UHFFFAOYSA-N 2-(4-hydroxyphenyl)prop-2-enenitrile Chemical compound OC1=CC=C(C(=C)C#N)C=C1 DZKAISAHHPTWNO-UHFFFAOYSA-N 0.000 claims description 2
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- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
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- 239000003708 ampul Substances 0.000 description 2
- 239000012062 aqueous buffer Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000000464 low-speed centrifugation Methods 0.000 description 2
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- CTYWXRDQWMRIIM-BQYQJAHWSA-N (e)-3-(3,5-ditert-butyl-4-hydroxyphenyl)prop-2-enoic acid Chemical group CC(C)(C)C1=CC(\C=C\C(O)=O)=CC(C(C)(C)C)=C1O CTYWXRDQWMRIIM-BQYQJAHWSA-N 0.000 description 1
- UEEZMPKIFPDZLX-ONEGZZNKSA-N (e)-3-(4-hydroxy-3,5-dimethylphenyl)prop-2-enoic acid Chemical compound CC1=CC(\C=C\C(O)=O)=CC(C)=C1O UEEZMPKIFPDZLX-ONEGZZNKSA-N 0.000 description 1
- 0 *C=C(*)c1c(*)c(*)c(*)c(*)c1* Chemical compound *C=C(*)c1c(*)c(*)c(*)c(*)c1* 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- ZMRCFZFFKWFWSK-UHFFFAOYSA-N 2,6-ditert-butyl-4-ethenylphenol Chemical compound CC(C)(C)C1=CC(C=C)=CC(C(C)(C)C)=C1O ZMRCFZFFKWFWSK-UHFFFAOYSA-N 0.000 description 1
- FMFHUEMLVAIBFI-UHFFFAOYSA-N 2-phenylethenyl acetate Chemical compound CC(=O)OC=CC1=CC=CC=C1 FMFHUEMLVAIBFI-UHFFFAOYSA-N 0.000 description 1
- 108010004032 Bromelains Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- 108700023158 Phenylalanine ammonia-lyases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 108020004511 Recombinant DNA Proteins 0.000 description 1
- 102000005158 Subtilisins Human genes 0.000 description 1
- 108010056079 Subtilisins Proteins 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000010364 biochemical engineering Methods 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 235000019835 bromelain Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229930005346 hydroxycinnamic acid Natural products 0.000 description 1
- 235000010359 hydroxycinnamic acids Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000009629 microbiological culture Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55686104P | 2004-03-26 | 2004-03-26 | |
| US60/556,861 | 2004-03-26 | ||
| PCT/US2005/009290 WO2005097719A1 (en) | 2004-03-26 | 2005-03-21 | A method for preparing hydroxystyrenes and acetylated derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE112005000464T5 true DE112005000464T5 (de) | 2007-02-15 |
Family
ID=35124980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE112005000464T Withdrawn DE112005000464T5 (de) | 2004-03-26 | 2005-03-21 | Verfahren zum Herstellen von Hydroxystyrolen und acetylierten Derivaten davon |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7586013B2 (enExample) |
| JP (1) | JP4764416B2 (enExample) |
| CN (1) | CN1934061A (enExample) |
| DE (1) | DE112005000464T5 (enExample) |
| TW (1) | TW200600493A (enExample) |
| WO (1) | WO2005097719A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007086559A1 (ja) * | 2006-01-27 | 2007-08-02 | Ube Industries, Ltd. | テトラヒドロピラン化合物の製造方法 |
| JP5600003B2 (ja) * | 2006-08-01 | 2014-10-01 | デュポン エレクトロニック ポリマーズ リミテッド パートナーシップ | フェノール材料からポリマーを調製する方法およびこれに関連する組成物 |
| US7468415B2 (en) * | 2007-01-04 | 2008-12-23 | E. I. Du Pont De Nemours And Company | Method for preparing glycidyloxystyrene monomers and polymers thereof |
| JP5526948B2 (ja) * | 2010-03-31 | 2014-06-18 | ユーハ味覚糖株式会社 | ２，６−ジプレニル−４−ビニルフェノールの生成方法 |
| CN102001918B (zh) * | 2010-09-27 | 2013-12-18 | 常州大学 | 对羟基苯乙烯及其衍生物的制备方法 |
| CN103086884A (zh) * | 2012-12-14 | 2013-05-08 | 湖南科源生物制品有限公司 | 乙酰化白藜芦醇的半合成方法 |
| JP6008201B2 (ja) * | 2013-05-10 | 2016-10-19 | 東レ・ファインケミカル株式会社 | スチレン誘導体の製造方法 |
| JP6094969B2 (ja) * | 2013-06-24 | 2017-03-15 | 東レ・ファインケミカル株式会社 | ヒドロキシスチレン誘導体の製造方法 |
| CN108129318A (zh) * | 2018-01-30 | 2018-06-08 | 上海博栋化学科技有限公司 | 一种3，4-二乙酰氧基苯乙烯的制备方法 |
| CN108658731B (zh) * | 2018-06-01 | 2022-05-06 | 巨野现代精细化工有限公司 | 一种对羟基苯乙烯的合成方法 |
| KR20220044564A (ko) | 2019-08-09 | 2022-04-08 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 화합물, 중합체, 조성물, 막형성용 조성물, 패턴형성방법, 절연막의 형성방법 및 화합물의 제조방법, 그리고 요오드함유 비닐폴리머 및 그의 아세틸화유도체의 제조방법 |
| TWI836227B (zh) * | 2020-06-18 | 2024-03-21 | 日商丸善石油化學股份有限公司 | 高純度４－羥基苯乙烯溶液、其製造方法及４－羥基苯乙烯系聚合物的製造方法 |
| CN114773191A (zh) * | 2022-04-29 | 2022-07-22 | 四川东材科技集团成都新材料有限公司 | 一种一锅法制备对乙酰氧基苯乙烯的方法 |
| TW202440507A (zh) | 2022-12-20 | 2024-10-16 | 日商三菱瓦斯化學股份有限公司 | 化合物之製造方法、聚合物、組成物、圖型形成方法 |
| CN115974659B (zh) * | 2022-12-29 | 2024-08-09 | 徐州博康信息化学品有限公司 | 一种1-(1-乙氧基乙氧基)-4-乙烯基苯的合成方法 |
| CN116924907A (zh) * | 2023-06-05 | 2023-10-24 | 成都东凯芯半导体材料有限公司 | 一种一锅法制备3,4-二乙酰氧基苯乙烯的方法 |
| TW202528272A (zh) * | 2023-09-08 | 2025-07-16 | 日商丸善石油化學股份有限公司 | 高純度ｏ－／ｍ－羥基苯乙烯溶液、其製造方法及ｏ－／ｍ－羥基苯乙烯系聚合物之製造方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3100447C2 (de) * | 1981-01-09 | 1983-02-24 | Volker Dipl.-Chem. 6000 Frankfurt Genrich | Fensterzählrohr und Verfahren zu seiner Herstellung |
| US4316995A (en) * | 1981-02-05 | 1982-02-23 | International Flavors & Fragrances Inc. | Process for preparing vinyl phenol |
| US5084533A (en) * | 1988-07-19 | 1992-01-28 | Hoechst Celanese Corporation | Neat (solventless) hydrogenation of 4-acetoxyacetophenone in the production of 4-acetoxystyrene and its polymers and hydrolysis products |
| US5245074A (en) * | 1988-07-19 | 1993-09-14 | Shah Bakulesh N | Process for the production of 4-acetoxystyrene, its polymers and hydrolysis products |
| US5151546A (en) * | 1988-07-19 | 1992-09-29 | Hoechst Celanese Corporation | Process for the production of 4-acetoxystyrene, its polymers and hydrolysis products |
| US5041614A (en) * | 1990-07-03 | 1991-08-20 | Hoechst Celanese Corporation | Method for the preparation of 4-acetoxystyrene |
| US5136083A (en) * | 1990-08-30 | 1992-08-04 | Hoechst Celanese Corporation | Process for the purification of 4-acetoxystyrene |
| EP0502819A1 (de) * | 1991-03-01 | 1992-09-09 | Ciba-Geigy Ag | Säurekatalytisch vernetzbare Copolymere |
| TW304235B (enExample) * | 1992-04-29 | 1997-05-01 | Ocg Microelectronic Materials | |
| US5453481A (en) * | 1995-03-01 | 1995-09-26 | Hoechst Celanese Corporation | Process for preparing vinylphenol polymers and copolymers |
| US5563289A (en) * | 1995-10-13 | 1996-10-08 | Hoechst Celanese Corporation | Process for preparing acetoxystyrene |
| US5578687A (en) * | 1995-10-13 | 1996-11-26 | Hoechst Celanese Corporation | Process for preparing poly(4-hydroxystyrene) |
| JP4284423B2 (ja) * | 2003-01-28 | 2009-06-24 | 和歌山県 | スチレン誘導体の製造方法 |
-
2005
- 2005-03-17 US US11/082,258 patent/US7586013B2/en not_active Expired - Fee Related
- 2005-03-21 WO PCT/US2005/009290 patent/WO2005097719A1/en not_active Ceased
- 2005-03-21 DE DE112005000464T patent/DE112005000464T5/de not_active Withdrawn
- 2005-03-21 CN CNA2005800095674A patent/CN1934061A/zh active Pending
- 2005-03-21 JP JP2007505052A patent/JP4764416B2/ja not_active Expired - Fee Related
- 2005-03-25 TW TW094109225A patent/TW200600493A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW200600493A (en) | 2006-01-01 |
| WO2005097719A1 (en) | 2005-10-20 |
| JP2007530548A (ja) | 2007-11-01 |
| JP4764416B2 (ja) | 2011-09-07 |
| US20050228191A1 (en) | 2005-10-13 |
| US7586013B2 (en) | 2009-09-08 |
| CN1934061A (zh) | 2007-03-21 |
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| R012 | Request for examination validly filed |
Effective date: 20120110 |
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| R119 | Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal fee |
Effective date: 20121002 |