TW436472B - Nitration process for diphenyl ethers - Google Patents
Nitration process for diphenyl ethers Download PDFInfo
- Publication number
- TW436472B TW436472B TW087111326A TW87111326A TW436472B TW 436472 B TW436472 B TW 436472B TW 087111326 A TW087111326 A TW 087111326A TW 87111326 A TW87111326 A TW 87111326A TW 436472 B TW436472 B TW 436472B
- Authority
- TW
- Taiwan
- Prior art keywords
- acid
- general formula
- tolyloxy
- trifluoro
- acetic anhydride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000006396 nitration reaction Methods 0.000 title claims description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 39
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 125000005843 halogen group Chemical group 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 239000011541 reaction mixture Substances 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 230000000802 nitrating effect Effects 0.000 claims abstract description 5
- 101100134925 Gallus gallus COR6 gene Proteins 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 19
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 15
- 229910017604 nitric acid Inorganic materials 0.000 claims description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 14
- 238000011049 filling Methods 0.000 claims description 10
- -1 DIPHENYL ETHERS Chemical class 0.000 claims description 9
- 239000005711 Benzoic acid Substances 0.000 claims description 7
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 7
- 235000010233 benzoic acid Nutrition 0.000 claims description 7
- 230000002079 cooperative effect Effects 0.000 claims description 4
- 235000015170 shellfish Nutrition 0.000 claims description 4
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 229920002301 cellulose acetate Polymers 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- 239000004009 herbicide Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 229950011008 tetrachloroethylene Drugs 0.000 description 5
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 150000003254 radicals Chemical group 0.000 description 3
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- FRBUNLLUASHNDJ-UHFFFAOYSA-N (2-nitrophenyl)hydrazine Chemical compound NNC1=CC=CC=C1[N+]([O-])=O FRBUNLLUASHNDJ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ANFHXXZCSPXIFE-UHFFFAOYSA-N 3-[3-chloro-4-(trifluoromethyl)phenoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=C(Cl)C(=CC=2)C(F)(F)F)=C1 ANFHXXZCSPXIFE-UHFFFAOYSA-N 0.000 description 1
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CJSPZCXWCMXXJU-UHFFFAOYSA-N F.F.F.ClC1=CC=CC=C1 Chemical compound F.F.F.ClC1=CC=CC=C1 CJSPZCXWCMXXJU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- XJCRCPKBJWRZAX-UHFFFAOYSA-L disodium;dibenzoate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 XJCRCPKBJWRZAX-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000005338 nitrobenzoic acids Chemical class 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
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)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/901,545 US6028219A (en) | 1995-09-13 | 1997-07-28 | Process for the nitration of diphenylethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW436472B true TW436472B (en) | 2001-05-28 |
Family
ID=25414397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW087111326A TW436472B (en) | 1997-07-28 | 1998-07-13 | Nitration process for diphenyl ethers |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6028219A (enExample) |
| EP (1) | EP1000010B1 (enExample) |
| JP (1) | JP2001510818A (enExample) |
| KR (1) | KR100571093B1 (enExample) |
| CN (1) | CN1176899C (enExample) |
| AR (1) | AR015137A1 (enExample) |
| AT (1) | ATE224865T1 (enExample) |
| AU (1) | AU8346998A (enExample) |
| BR (1) | BR9811048A (enExample) |
| CA (1) | CA2291438C (enExample) |
| DE (1) | DE69808300T2 (enExample) |
| DK (1) | DK1000010T3 (enExample) |
| ES (1) | ES2180186T3 (enExample) |
| HU (1) | HUP0002525A3 (enExample) |
| IL (1) | IL133151A (enExample) |
| TW (1) | TW436472B (enExample) |
| WO (1) | WO1999005087A1 (enExample) |
| ZA (1) | ZA986637B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9930369D0 (en) * | 1999-12-22 | 2000-02-09 | Zeneca Ltd | Chemical process |
| DE10196234B4 (de) * | 2000-05-26 | 2008-04-30 | Engelhard Lyon S.A. | Verfahren zur Herstellung eines Verbundprodukts aus Kollagen für die Gewebebildung und seine Verwendung |
| DE102007010161A1 (de) * | 2007-03-02 | 2008-09-04 | Saltigo Gmbh | Verfahren zur Nitrierung substituierter Benzole in Gegenwart von Propionsäure |
| CN102329255B (zh) * | 2011-10-31 | 2013-11-13 | 江苏长青农化股份有限公司 | 定向硝化合成氟磺胺草醚工艺 |
| CN103387524B (zh) * | 2013-07-23 | 2015-04-15 | 山东科源化工有限公司 | 一种氟磺胺草醚的制备方法 |
| CN112358400A (zh) * | 2020-10-22 | 2021-02-12 | 烟台大学 | 一种微反应器中硝化合成三氟羧草醚的方法 |
| CN115403488B (zh) * | 2021-05-27 | 2024-07-19 | 江苏联化科技有限公司 | 氟磺胺草醚的制备方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5248173B2 (enExample) * | 1973-02-20 | 1977-12-08 | ||
| US4031131A (en) * | 1975-09-29 | 1977-06-21 | Rohm And Haas Company | Process for preparing phenoxybenzoic acids |
| GB1478428A (en) * | 1975-12-11 | 1977-06-29 | Ishihara Sangyo Kaisha Kk | Substituted diphenylethers and herbicidal composition thereof |
| EP0003416B1 (en) * | 1978-01-19 | 1981-08-26 | Imperial Chemical Industries Plc | Diphenyl ether compounds useful as herbicides; methods of using them, processes for preparing them, and herbicidal compositions containing them |
| EP0022610B1 (en) * | 1979-06-22 | 1986-09-03 | Rhone-Poulenc Agrochimie | Process for preparing 2-nitro-5-(substituted-phenoxy) benzoic acids and salts thereof |
| US4400530A (en) * | 1980-06-27 | 1983-08-23 | Ppg Industries, Inc. | Process for preparing substituted diphenyl ethers |
| US4405805A (en) * | 1981-07-27 | 1983-09-20 | Rhone-Poulenc, Inc. | Process for recovering and purifying herbicidal phenoxybenzoic acid derivatives |
| US4594440A (en) * | 1981-07-27 | 1986-06-10 | Rhone:Pulenc, Inc. | Process for recovering and purifying herbicidal phenoxybenzoic acid derivatives |
| US4424393A (en) * | 1981-08-24 | 1984-01-03 | Ppg Industries, Inc. | Process of preparation of substituted diphenyl ethers |
| US4743703A (en) * | 1981-10-19 | 1988-05-10 | Rohm And Haas Company | Herbicidal 4-fluoroalkyl-4'-nitrodiphenyl ethers |
| US4429146A (en) * | 1982-04-15 | 1984-01-31 | Gaf Corporation | Substituted diphenyl ether herbicides and process for use |
| DE3247669A1 (de) * | 1982-12-23 | 1984-06-28 | Basf Ag, 6700 Ludwigshafen | Neue phenylglyoxylsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| DE3322817A1 (de) * | 1983-06-24 | 1985-01-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von nitrierten diphenylethern |
| EP0147798B1 (en) * | 1984-01-03 | 1989-11-23 | General Electric Company | Nitration reactions with acid anhydride promoters |
| HU193194B (en) * | 1984-01-17 | 1987-08-28 | Budapesti Vegyimuevek | Fungicide compositions containing phenoxy-benzaldehyde derivatives as active substances and process for preparing the active substances |
| HU190222B (en) * | 1984-01-17 | 1986-08-28 | Budapesti Vegyimuevek,Hu | Fungicide comprising substituted phenoxy-benzaldehyde as active substance |
| GB8628109D0 (en) * | 1986-11-25 | 1986-12-31 | Ici Plc | Chemical process |
| HU200538B (en) * | 1987-06-16 | 1990-07-28 | Budapesti Vegyimuevek | Herbicidal compositons with improves selectivity and process for producing the two active ingredients in one reaction step |
| PT101207A (pt) * | 1993-02-26 | 1994-08-31 | Inst Nac De Engenharia E Tecno | Processo para a nitracao de compostos aromaticos em condicoes suaves e nao corrosivas |
| ES2119308T3 (es) * | 1994-02-17 | 1998-10-01 | Zeneca Ltd | Proceso para la fosgenacion en presencia de acetonitrilo. |
| GB9518705D0 (en) * | 1995-09-13 | 1995-11-15 | Zeneca Ltd | Chemical process |
| IN190438B (enExample) * | 1996-11-01 | 2003-07-26 | Syngenta Ltd |
-
1997
- 1997-07-28 US US08/901,545 patent/US6028219A/en not_active Expired - Lifetime
-
1998
- 1998-07-07 CA CA002291438A patent/CA2291438C/en not_active Expired - Lifetime
- 1998-07-07 BR BR9811048-9A patent/BR9811048A/pt not_active Application Discontinuation
- 1998-07-07 EP EP98933766A patent/EP1000010B1/en not_active Expired - Lifetime
- 1998-07-07 HU HU0002525A patent/HUP0002525A3/hu unknown
- 1998-07-07 AU AU83469/98A patent/AU8346998A/en not_active Abandoned
- 1998-07-07 AT AT98933766T patent/ATE224865T1/de not_active IP Right Cessation
- 1998-07-07 ES ES98933766T patent/ES2180186T3/es not_active Expired - Lifetime
- 1998-07-07 DE DE69808300T patent/DE69808300T2/de not_active Expired - Fee Related
- 1998-07-07 DK DK98933766T patent/DK1000010T3/da active
- 1998-07-07 IL IL13315198A patent/IL133151A/en not_active IP Right Cessation
- 1998-07-07 CN CNB988076101A patent/CN1176899C/zh not_active Expired - Lifetime
- 1998-07-07 KR KR1020007000887A patent/KR100571093B1/ko not_active Expired - Lifetime
- 1998-07-07 WO PCT/GB1998/001991 patent/WO1999005087A1/en not_active Ceased
- 1998-07-07 JP JP2000504089A patent/JP2001510818A/ja active Pending
- 1998-07-13 TW TW087111326A patent/TW436472B/zh not_active IP Right Cessation
- 1998-07-24 ZA ZA986637A patent/ZA986637B/xx unknown
- 1998-07-27 AR ARP980103687A patent/AR015137A1/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010022308A (ko) | 2001-03-15 |
| ES2180186T3 (es) | 2003-02-01 |
| CA2291438C (en) | 2007-10-16 |
| EP1000010B1 (en) | 2002-09-25 |
| JP2001510818A (ja) | 2001-08-07 |
| HUP0002525A2 (hu) | 2000-11-28 |
| DE69808300D1 (de) | 2002-10-31 |
| US6028219A (en) | 2000-02-22 |
| DK1000010T3 (da) | 2003-02-03 |
| HUP0002525A3 (en) | 2001-02-28 |
| IL133151A (en) | 2002-11-10 |
| KR100571093B1 (ko) | 2006-04-13 |
| BR9811048A (pt) | 2000-09-05 |
| DE69808300T2 (de) | 2003-05-15 |
| AR015137A1 (es) | 2001-04-18 |
| EP1000010A1 (en) | 2000-05-17 |
| CN1176899C (zh) | 2004-11-24 |
| WO1999005087A1 (en) | 1999-02-04 |
| IL133151A0 (en) | 2001-03-19 |
| CA2291438A1 (en) | 1999-02-04 |
| AU8346998A (en) | 1999-02-16 |
| CN1266422A (zh) | 2000-09-13 |
| ZA986637B (en) | 1999-01-28 |
| ATE224865T1 (de) | 2002-10-15 |
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| GD4A | Issue of patent certificate for granted invention patent | ||
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