RU2193549C2 - Способ получения галоидзамещенных соединений гидроксидифенила - Google Patents
Способ получения галоидзамещенных соединений гидроксидифенила Download PDFInfo
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- RU2193549C2 RU2193549C2 RU98102130/04A RU98102130A RU2193549C2 RU 2193549 C2 RU2193549 C2 RU 2193549C2 RU 98102130/04 A RU98102130/04 A RU 98102130/04A RU 98102130 A RU98102130 A RU 98102130A RU 2193549 C2 RU2193549 C2 RU 2193549C2
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- compounds
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims abstract description 25
- 230000015572 biosynthetic process Effects 0.000 title abstract 4
- 238000003786 synthesis reaction Methods 0.000 title abstract 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 claims abstract description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 14
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 11
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims abstract description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 benzene compound Chemical class 0.000 claims abstract description 10
- 230000003647 oxidation Effects 0.000 claims abstract description 9
- 230000007062 hydrolysis Effects 0.000 claims abstract description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 8
- 239000002841 Lewis acid Substances 0.000 claims abstract description 6
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000012346 acetyl chloride Substances 0.000 claims abstract description 5
- 238000006640 acetylation reaction Methods 0.000 claims abstract description 5
- 238000005886 esterification reaction Methods 0.000 claims abstract description 5
- 229910021538 borax Inorganic materials 0.000 claims abstract description 4
- 230000032050 esterification Effects 0.000 claims abstract description 4
- 235000010339 sodium tetraborate Nutrition 0.000 claims abstract description 4
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000021736 acetylation Effects 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims description 12
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 4
- 244000005700 microbiome Species 0.000 abstract description 3
- 238000007086 side reaction Methods 0.000 abstract description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- CYNFEPKQDJHIMV-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=CC=C1Cl CYNFEPKQDJHIMV-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- 0 C*N(CC=C1)C=C1Oc(ccc(*)c1)c1O Chemical compound C*N(CC=C1)C=C1Oc(ccc(*)c1)c1O 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000003020 moisturizing effect Effects 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- RVZFFCSCPXYAPX-UHFFFAOYSA-N 1-[5-chloro-2-(2,4-dichlorophenoxy)phenyl]ethanone Chemical compound CC(=O)C1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl RVZFFCSCPXYAPX-UHFFFAOYSA-N 0.000 description 1
- KZGSCEBUKKTKPM-UHFFFAOYSA-N 1-[5-chloro-2-(4-chlorophenoxy)phenyl]ethanone Chemical compound CC(=O)C1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1 KZGSCEBUKKTKPM-UHFFFAOYSA-N 0.000 description 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- YVKQDASGCRLLKL-UHFFFAOYSA-N acetic acid;magnesium Chemical compound [Mg].CC(O)=O.CC(O)=O YVKQDASGCRLLKL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- BYNQFCJOHGOKSS-UHFFFAOYSA-N diclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1 BYNQFCJOHGOKSS-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- QBIHEHITTANFEO-UHFFFAOYSA-N sodium;tetrahydrate Chemical compound O.O.O.O.[Na] QBIHEHITTANFEO-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
- C07C67/42—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester by oxidation of secondary alcohols or ketones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97810064 | 1997-02-05 | ||
| EP97810064.2 | 1997-02-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU98102130A RU98102130A (ru) | 1999-11-10 |
| RU2193549C2 true RU2193549C2 (ru) | 2002-11-27 |
Family
ID=8230148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU98102130/04A RU2193549C2 (ru) | 1997-02-05 | 1998-02-04 | Способ получения галоидзамещенных соединений гидроксидифенила |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6215029B1 (enExample) |
| EP (1) | EP0857711B1 (enExample) |
| JP (1) | JP4272270B2 (enExample) |
| KR (1) | KR100549969B1 (enExample) |
| CN (1) | CN1140490C (enExample) |
| BR (1) | BR9800566A (enExample) |
| CZ (1) | CZ295415B6 (enExample) |
| DE (1) | DE59808555D1 (enExample) |
| ES (1) | ES2200299T3 (enExample) |
| IL (1) | IL123015A (enExample) |
| RU (1) | RU2193549C2 (enExample) |
| SK (1) | SK283874B6 (enExample) |
| ZA (1) | ZA98899B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2419287C2 (ru) * | 2005-07-19 | 2011-05-27 | Байер Энимэл Хельс ГмбХ | Дезинфицирующее средство для борьбы с паразитическими простейшими |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0887333B1 (en) * | 1997-06-25 | 2001-11-14 | Ciba SC Holding AG | Process for the production of halogeno-o-hydroxydiphenyl compounds |
| TW561143B (en) * | 1997-06-25 | 2003-11-11 | Ciba Sc Holding Ag | Process for the production of halogeno-o-hydroxydiphenyl compounds |
| WO1999010310A1 (en) * | 1997-08-29 | 1999-03-04 | The Dow Chemical Company | Process for producing diphenylethers and esters |
| JP2002526515A (ja) * | 1998-10-06 | 2002-08-20 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 4,4′−ジハロゲン−o−ヒドロキシジフェニル化合物の製造方法 |
| KR100634721B1 (ko) * | 1998-10-06 | 2006-10-17 | 시바 스페셜티 케미칼스 홀딩 인크. | 4,4'-디할로겐-o-하이드록시디페닐 화합물의 제조방법 |
| TWI274748B (en) | 2000-05-04 | 2007-03-01 | Ciba Sc Holding Ag | Process for the preparation of halogenated hydroxydiphenyl compounds |
| EP1341886B1 (en) * | 2000-12-14 | 2006-03-08 | Ciba SC Holding AG | Surface-active compositions |
| WO2003031382A2 (en) * | 2001-10-09 | 2003-04-17 | Ciba Specialty Chemicals Holding Inc. | Process for the preparation of hydroxydiphenyl ether compounds |
| US20050266095A1 (en) * | 2004-06-01 | 2005-12-01 | Erning Xia | Gentle preservative compositions |
| JP6028552B2 (ja) * | 2012-12-07 | 2016-11-16 | Jnc株式会社 | 過酸組成物および該過酸組成物を用いたアセトキシフェニル化合物の製造方法 |
| JP6032740B2 (ja) * | 2012-12-07 | 2016-11-30 | Jnc株式会社 | アセトキシフェニル化合物の製造方法 |
| CN115490578B (zh) * | 2022-09-23 | 2023-12-22 | 江苏理工学院 | 一种碳同位素标记的三氯生的制备方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4065503A (en) * | 1974-09-30 | 1977-12-27 | Sandoz, Inc. | P-Phenoxy-alkylphenones and corresponding alcohols |
| DE3723994A1 (de) * | 1986-07-23 | 1988-02-04 | Ciba Geigy Ag | Mikrobizide zubereitung |
| EP0384043A2 (en) * | 1989-02-21 | 1990-08-29 | The Dow Chemical Company | Methods for the preparation of brominated intermediates |
| SU1740365A1 (ru) * | 1990-04-04 | 1992-06-15 | Ярославский политехнический институт | Способ получени м-феноксифенола |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL133434C (enExample) | 1963-02-22 | 1972-02-15 | ||
| GB1051823A (enExample) * | 1964-02-14 | |||
| DE1298982B (de) | 1966-01-03 | 1969-07-10 | Knoll Ag | Urethane und Verfahren zu ihrer Herstellung |
| DE3040849A1 (de) | 1980-10-30 | 1982-06-09 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von diphenylaethern |
| FR2624507B1 (fr) | 1987-12-11 | 1990-06-15 | Rhone Poulenc Chimie | Procede de preparation de derives aromatiques hydroxyles par la reaction de baeyer-villiger |
| US5012017A (en) | 1988-08-18 | 1991-04-30 | Dowelanco | Phenoxyphenoxypropionates, intermediates thereof and methods of preparation |
| WO1999010310A1 (en) | 1997-08-29 | 1999-03-04 | The Dow Chemical Company | Process for producing diphenylethers and esters |
-
1998
- 1998-01-21 IL IL12301598A patent/IL123015A/xx not_active IP Right Cessation
- 1998-01-27 DE DE59808555T patent/DE59808555D1/de not_active Expired - Lifetime
- 1998-01-27 ES ES98810044T patent/ES2200299T3/es not_active Expired - Lifetime
- 1998-01-27 EP EP98810044A patent/EP0857711B1/de not_active Expired - Lifetime
- 1998-02-03 SK SK149-98A patent/SK283874B6/sk not_active IP Right Cessation
- 1998-02-03 KR KR1019980002866A patent/KR100549969B1/ko not_active Expired - Fee Related
- 1998-02-04 RU RU98102130/04A patent/RU2193549C2/ru not_active IP Right Cessation
- 1998-02-04 CZ CZ1998334A patent/CZ295415B6/cs not_active IP Right Cessation
- 1998-02-04 ZA ZA98899A patent/ZA98899B/xx unknown
- 1998-02-04 CN CNB981063446A patent/CN1140490C/zh not_active Expired - Fee Related
- 1998-02-05 JP JP02370798A patent/JP4272270B2/ja not_active Expired - Fee Related
- 1998-02-05 BR BR9800566A patent/BR9800566A/pt not_active IP Right Cessation
-
1999
- 1999-06-09 US US09/328,744 patent/US6215029B1/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4065503A (en) * | 1974-09-30 | 1977-12-27 | Sandoz, Inc. | P-Phenoxy-alkylphenones and corresponding alcohols |
| DE3723994A1 (de) * | 1986-07-23 | 1988-02-04 | Ciba Geigy Ag | Mikrobizide zubereitung |
| EP0384043A2 (en) * | 1989-02-21 | 1990-08-29 | The Dow Chemical Company | Methods for the preparation of brominated intermediates |
| SU1740365A1 (ru) * | 1990-04-04 | 1992-06-15 | Ярославский политехнический институт | Способ получени м-феноксифенола |
Non-Patent Citations (2)
| Title |
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| The Merck Index, Thelfth Edition, 1996, MERCK & CO, WHITEHOUSE STATION. p.1646, compound № 1984. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2419287C2 (ru) * | 2005-07-19 | 2011-05-27 | Байер Энимэл Хельс ГмбХ | Дезинфицирующее средство для борьбы с паразитическими простейшими |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA98899B (en) | 1998-08-05 |
| JPH10259154A (ja) | 1998-09-29 |
| SK14998A3 (en) | 1998-09-09 |
| CZ33498A3 (cs) | 1998-08-12 |
| CN1140490C (zh) | 2004-03-03 |
| IL123015A0 (en) | 1998-09-24 |
| KR100549969B1 (ko) | 2006-12-07 |
| US6215029B1 (en) | 2001-04-10 |
| EP0857711A1 (de) | 1998-08-12 |
| SK283874B6 (sk) | 2004-03-02 |
| DE59808555D1 (de) | 2003-07-10 |
| BR9800566A (pt) | 1999-06-29 |
| ES2200299T3 (es) | 2004-03-01 |
| KR19980071013A (ko) | 1998-10-26 |
| JP4272270B2 (ja) | 2009-06-03 |
| CZ295415B6 (cs) | 2005-08-17 |
| IL123015A (en) | 2003-07-06 |
| CN1194258A (zh) | 1998-09-30 |
| HK1015357A1 (en) | 1999-10-15 |
| EP0857711B1 (de) | 2003-06-04 |
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