DK1848678T3 - METHOD OF MANUFACTURING INTERMEDIATES - Google Patents
METHOD OF MANUFACTURING INTERMEDIATES Download PDFInfo
- Publication number
- DK1848678T3 DK1848678T3 DK06704443.8T DK06704443T DK1848678T3 DK 1848678 T3 DK1848678 T3 DK 1848678T3 DK 06704443 T DK06704443 T DK 06704443T DK 1848678 T3 DK1848678 T3 DK 1848678T3
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- compound
- nitrite
- aqueous
- temperature
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000000543 intermediate Substances 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 23
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000010533 azeotropic distillation Methods 0.000 claims description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 11
- 239000010949 copper Substances 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 8
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 7
- 150000001555 benzenes Chemical class 0.000 claims description 7
- 229910052794 bromium Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 6
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 claims description 6
- 229910001507 metal halide Inorganic materials 0.000 claims description 6
- 150000005309 metal halides Chemical class 0.000 claims description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 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
- 238000005292 vacuum distillation Methods 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 3
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 claims description 3
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims 4
- 238000006386 neutralization reaction Methods 0.000 claims 4
- 238000005191 phase separation Methods 0.000 claims 4
- 229940078552 o-xylene Drugs 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 238000000297 Sandmeyer reaction Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- -1 aromatic fluorides Chemical class 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- 239000011260 aqueous acid Substances 0.000 description 6
- QWIITRRSNVBPDK-UHFFFAOYSA-N 2-bromo-1,3-diethyl-5-methylbenzene Chemical compound CCC1=CC(C)=CC(CC)=C1Br QWIITRRSNVBPDK-UHFFFAOYSA-N 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CQKJMEVQJREFRF-UHFFFAOYSA-N 2-chloro-1,3-diethyl-5-methylbenzene Chemical compound CCC1=CC(C)=CC(CC)=C1Cl CQKJMEVQJREFRF-UHFFFAOYSA-N 0.000 description 4
- 238000006193 diazotization reaction Methods 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 238000000197 pyrolysis Methods 0.000 description 4
- OIXUMNZGNCAOKY-UHFFFAOYSA-N 2,6-diethyl-4-methylaniline Chemical compound CCC1=CC(C)=CC(CC)=C1N OIXUMNZGNCAOKY-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- VIMIAQYISZGMEJ-UHFFFAOYSA-N 2,4-dibromo-1,3-diethyl-5-methylbenzene Chemical compound CCC1=CC(C)=C(Br)C(CC)=C1Br VIMIAQYISZGMEJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 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 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FEVKBWGLRAAJCR-UHFFFAOYSA-N n,2-diethyl-n-methylaniline Chemical compound CCN(C)C1=CC=CC=C1CC FEVKBWGLRAAJCR-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 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
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/02—Monocyclic aromatic halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65117505P | 2005-02-09 | 2005-02-09 | |
| PCT/EP2006/001068 WO2006084663A1 (en) | 2005-02-09 | 2006-02-07 | Process for the preparation of intermediates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK1848678T3 true DK1848678T3 (en) | 2015-09-21 |
Family
ID=36390191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK06704443.8T DK1848678T3 (en) | 2005-02-09 | 2006-02-07 | METHOD OF MANUFACTURING INTERMEDIATES |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US8030529B2 (enExample) |
| EP (1) | EP1848678B1 (enExample) |
| JP (2) | JP5254625B2 (enExample) |
| KR (1) | KR101355873B1 (enExample) |
| CN (2) | CN102603444A (enExample) |
| AR (1) | AR053123A1 (enExample) |
| AU (1) | AU2006212397B2 (enExample) |
| BR (1) | BRPI0606976B1 (enExample) |
| CA (1) | CA2596590C (enExample) |
| DK (1) | DK1848678T3 (enExample) |
| EA (1) | EA013842B1 (enExample) |
| ES (1) | ES2546960T3 (enExample) |
| HU (1) | HUE027652T2 (enExample) |
| IL (1) | IL184715A (enExample) |
| MX (1) | MX2007009341A (enExample) |
| PL (1) | PL1848678T3 (enExample) |
| PT (1) | PT1848678E (enExample) |
| TW (1) | TWI360533B (enExample) |
| UA (1) | UA89218C2 (enExample) |
| WO (1) | WO2006084663A1 (enExample) |
| ZA (1) | ZA200705880B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101492343B (zh) * | 2008-12-30 | 2011-08-10 | 中钢集团鞍山热能研究院有限公司 | 3,5-二甲基溴苯的制备方法 |
| DK2406205T3 (en) | 2009-03-12 | 2017-02-27 | Bayer Ip Gmbh | PROCEDURE FOR MANUFACTURING CHLOR AND BROMAROMATS |
| AR086590A1 (es) | 2011-05-30 | 2014-01-08 | Sumitomo Chemical Co | Compuestos de ciclohexanona y herbicidas que los comprenden |
| US9414588B2 (en) | 2012-11-08 | 2016-08-16 | Sumitomo Chemical Company, Limited | Herbicide composition |
| WO2018015489A1 (en) | 2016-07-22 | 2018-01-25 | Syngenta Participations Ag | Process for the preparation of phenylmalonic acid dinitriles |
| CN109336762B (zh) * | 2018-11-30 | 2021-03-16 | 江苏富鼎化学有限公司 | 2-(2,6-二乙基-4-甲基苯)丙二酸二乙酯的合成方法 |
| CN114907181B (zh) * | 2021-02-09 | 2024-04-23 | 北京颖泰嘉和生物科技股份有限公司 | 用于桑德迈尔反应的装置和连续制备2,6-二乙基-4-甲基溴苯的方法 |
| WO2023044364A1 (en) | 2021-09-15 | 2023-03-23 | Enko Chem, Inc. | Protoporphyrinogen oxidase inhibitors |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE600706C (de) * | 1933-03-24 | 1934-07-30 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung aromatischer, im Kern fluorierter Verbindungen |
| DE1695659B1 (de) * | 1967-12-18 | 1971-12-16 | Ruetgerswerke Ag | Verfahren zur Herstellung von 2-Chlorpyridinen |
| JPS59112965A (ja) | 1982-12-20 | 1984-06-29 | Koei Chem Co Ltd | ４−クロルピリジン塩酸塩の製造法 |
| FR2586247B1 (fr) * | 1985-08-19 | 1987-11-20 | Rhone Poulenc Spec Chim | Procede de preparation de composes aromatiques fluores |
| US4822927A (en) | 1987-11-24 | 1989-04-18 | Mallinckrodt, Inc. | Continuous decomposition of diazonium fluorides |
| JPH01283230A (ja) | 1988-05-09 | 1989-11-14 | Mitsui Toatsu Chem Inc | 芳香族弗素化合物の製造方法 |
| WO1992016510A1 (en) | 1991-03-19 | 1992-10-01 | Ciba-Geigy Ag | Novel herbicidally, acaricidally and insecticidally active compounds |
| DE4109208A1 (de) | 1991-03-21 | 1992-09-24 | Bayer Ag | 3-hydroxy-4-aryl-5-oxo-pyrazolin-derivate |
| DE4111214A1 (de) | 1991-04-06 | 1992-10-08 | Bayer Ag | Verfahren zur herstellung von 2-chlorpyridinen |
| ES2130431T3 (es) | 1993-07-05 | 1999-07-01 | Bayer Ag | Aril-cetoenolheterociclos substituidos. |
| WO1996021652A1 (en) | 1995-01-13 | 1996-07-18 | Novartis Ag | 4-aryl- and 4-heteroaryl -5-oxopyrazoline derivatives having pesticidal properties |
| JP4036470B2 (ja) | 1995-02-13 | 2008-01-23 | バイエル・アクチエンゲゼルシヤフト | 除草剤および有害生物防除剤としての２−フェニル置換複素環式１，３−ケトエノール |
| DE19517186A1 (de) | 1995-05-11 | 1996-11-14 | Bayer Ag | Verfahren zur Herstellung substituierter 2-Fluor-pyrimidine |
| ES2189877T3 (es) | 1995-06-30 | 2003-07-16 | Bayer Cropscience Ag | Cetoenoles dialquil-halogenofenilsubstituidos para el empleo como herbicidas y pesticidas. |
| HU228637B1 (en) | 1998-03-13 | 2013-04-29 | Syngenta Participations Ag | Herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline derivatives and use thereof |
| KR100752941B1 (ko) | 1999-06-16 | 2007-08-30 | 신젠타 파티서페이션즈 아게 | 제초제 유도체의 제조방법 |
| JP2003502403A (ja) * | 1999-06-16 | 2003-01-21 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 新規中間体 |
| CN1223594C (zh) | 2001-04-05 | 2005-10-19 | 住友化学工业株式会社 | 2,6－二卤代嘌呤的制备方法 |
| AR042282A1 (es) | 2002-12-05 | 2005-06-15 | Syngenta Participations Ag | Proceso para la preparacion de dinitrilos de acido fenilmalonico |
-
2006
- 2006-02-07 DK DK06704443.8T patent/DK1848678T3/en active
- 2006-02-07 CA CA2596590A patent/CA2596590C/en active Active
- 2006-02-07 PT PT67044438T patent/PT1848678E/pt unknown
- 2006-02-07 WO PCT/EP2006/001068 patent/WO2006084663A1/en not_active Ceased
- 2006-02-07 AU AU2006212397A patent/AU2006212397B2/en active Active
- 2006-02-07 HU HUE06704443A patent/HUE027652T2/en unknown
- 2006-02-07 JP JP2007553565A patent/JP5254625B2/ja active Active
- 2006-02-07 EP EP06704443.8A patent/EP1848678B1/en active Active
- 2006-02-07 CN CN2012100205799A patent/CN102603444A/zh active Pending
- 2006-02-07 CN CN2006800044338A patent/CN101115704B/zh active Active
- 2006-02-07 PL PL06704443T patent/PL1848678T3/pl unknown
- 2006-02-07 TW TW095103994A patent/TWI360533B/zh active
- 2006-02-07 AR ARP060100436A patent/AR053123A1/es active IP Right Grant
- 2006-02-07 UA UAA200709950A patent/UA89218C2/ru unknown
- 2006-02-07 BR BRPI0606976A patent/BRPI0606976B1/pt active IP Right Grant
- 2006-02-07 ES ES06704443.8T patent/ES2546960T3/es active Active
- 2006-02-07 EA EA200701616A patent/EA013842B1/ru not_active IP Right Cessation
- 2006-02-07 US US11/815,458 patent/US8030529B2/en active Active
- 2006-02-07 MX MX2007009341A patent/MX2007009341A/es active IP Right Grant
- 2006-02-07 KR KR1020077018180A patent/KR101355873B1/ko active Active
-
2007
- 2007-07-18 ZA ZA200705880A patent/ZA200705880B/xx unknown
- 2007-07-19 IL IL184715A patent/IL184715A/en active IP Right Grant
-
2012
- 2012-06-04 JP JP2012127185A patent/JP5411319B2/ja active Active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6426795B2 (ja) | 塩素化プロペンの製造方法 | |
| EP2964597B1 (en) | Process for the production of chlorinated alkanes | |
| US8431718B2 (en) | Process for the preparation of 5-fluoro-1-alkyl-3-fluoroalky1-1H-pyrazole-4-carbonyl chlorides and fluorides | |
| BR112012011961B1 (pt) | Processo para produzir cloretos de 5-flúor-1- alquil-3-fluoralquil-1h-pirazol-4-carbonila, 5- flúor-1-alquil-3-fluoralquil-1h-pirazol-4- carbaldeído e seu processo de produção | |
| DK1848678T3 (en) | METHOD OF MANUFACTURING INTERMEDIATES | |
| CN104557646B (zh) | 生产芳基硫五氟化物的工业方法 | |
| CN100519510C (zh) | 农药合成中间体的制备方法 | |
| JP5197386B2 (ja) | ３，５−ビス（トリフルオロメチル）−ｎ−メチルベンジルアミンの製法 | |
| US9334241B2 (en) | Process for the preparation of N-substituted pyrazole compounds | |
| CN101160278B (zh) | 由氟苯衍生物制备1,3,5-三氟-2,4,6-三氯苯的方法 | |
| CN107531640B (zh) | 制备5-氟-1h-吡唑-4-碳酰氟的方法 | |
| CN103068789B (zh) | 选择性间位氯化烷基苯胺的方法 | |
| US6069255A (en) | Preparation of vinyl isothiocyanates | |
| JP3937600B2 (ja) | アミノベンゾニトリル化合物の製造方法 | |
| TW202012358A (zh) | 由２－（羥基烷基）－苯胺製造經取代的４－胺基二氫茚衍生物之方法 | |
| CN101108837A (zh) | 制备卤代烯丙基糠醇的方法 | |
| US20220315545A1 (en) | Process of preparing 2-(phenylimino)-1,3-thiazolidin-4-ones | |
| JP2003034681A (ja) | Ｎ−（ω−ブロモアルキル）フタルイミド類の製造方法 |