DE4133676A1 - Verfahren zur radikalischen chlorierung oder bromierung von methylaromaten - Google Patents
Verfahren zur radikalischen chlorierung oder bromierung von methylaromatenInfo
- Publication number
- DE4133676A1 DE4133676A1 DE4133676A DE4133676A DE4133676A1 DE 4133676 A1 DE4133676 A1 DE 4133676A1 DE 4133676 A DE4133676 A DE 4133676A DE 4133676 A DE4133676 A DE 4133676A DE 4133676 A1 DE4133676 A1 DE 4133676A1
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- halogen
- methyl
- hydrogen
- cohal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 17
- 239000000796 flavoring agent Substances 0.000 title 1
- 235000019634 flavors Nutrition 0.000 title 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 title 1
- 239000000460 chlorine Substances 0.000 claims description 50
- 229910052801 chlorine Inorganic materials 0.000 claims description 46
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 43
- 238000005660 chlorination reaction Methods 0.000 claims description 27
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 230000026030 halogenation Effects 0.000 claims description 12
- 238000005658 halogenation reaction Methods 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 11
- -1 tribromomethyl Chemical group 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 6
- 230000008030 elimination Effects 0.000 claims description 5
- 238000003379 elimination reaction Methods 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- LYQFWZFBNBDLEO-UHFFFAOYSA-M caesium bromide Chemical compound [Br-].[Cs+] LYQFWZFBNBDLEO-UHFFFAOYSA-M 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- JAAGVIUFBAHDMA-UHFFFAOYSA-M rubidium bromide Chemical compound [Br-].[Rb+] JAAGVIUFBAHDMA-UHFFFAOYSA-M 0.000 claims description 4
- FGDZQCVHDSGLHJ-UHFFFAOYSA-M rubidium chloride Chemical compound [Cl-].[Rb+] FGDZQCVHDSGLHJ-UHFFFAOYSA-M 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 3
- 150000008045 alkali metal halides Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Chemical group 0.000 claims description 3
- XDIQTPZOIIYCTR-GRFIIANRSA-N [[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3r)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-[2-(3,3,3-trifluoro-2-oxopropyl)sulfanylethylamino]propyl]amino]butyl] hydrogen phosphate Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSCC(=O)C(F)(F)F)O[C@H]1N1C2=NC=NC(N)=C2N=C1 XDIQTPZOIIYCTR-GRFIIANRSA-N 0.000 claims description 2
- XQPRBTXUXXVTKB-UHFFFAOYSA-M caesium iodide Inorganic materials [I-].[Cs+] XQPRBTXUXXVTKB-UHFFFAOYSA-M 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 239000013310 covalent-organic framework Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 16
- 239000000047 product Substances 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
- WZWNFRQEMDEWEO-UHFFFAOYSA-N 1,5-dichloro-2-fluoro-4-(trichloromethyl)benzene Chemical compound FC1=CC(C(Cl)(Cl)Cl)=C(Cl)C=C1Cl WZWNFRQEMDEWEO-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- BTQZKHUEUDPRST-UHFFFAOYSA-N 1-fluoro-3-methylbenzene Chemical compound CC1=CC=CC(F)=C1 BTQZKHUEUDPRST-UHFFFAOYSA-N 0.000 description 5
- HFJWGYDWSRNFPC-UHFFFAOYSA-N 2,3-dichloro-6-(trichloromethyl)quinoxaline Chemical compound C1=C(C(Cl)(Cl)Cl)C=C2N=C(Cl)C(Cl)=NC2=C1 HFJWGYDWSRNFPC-UHFFFAOYSA-N 0.000 description 5
- LNIAVCRNJMPGGT-UHFFFAOYSA-N 4-(trichloromethyl)benzoyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)(Cl)Cl)C=C1 LNIAVCRNJMPGGT-UHFFFAOYSA-N 0.000 description 5
- 230000000875 corresponding effect Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 4
- LPRRFFOICNSSMK-UHFFFAOYSA-N 1,5-dichloro-2-(dichloromethyl)-4-fluorobenzene Chemical compound FC1=CC(C(Cl)Cl)=C(Cl)C=C1Cl LPRRFFOICNSSMK-UHFFFAOYSA-N 0.000 description 4
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical group OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- BJVGXXXWPQLLLP-UHFFFAOYSA-N 1,2,3-trichloro-4-fluorobenzene Chemical compound FC1=CC=C(Cl)C(Cl)=C1Cl BJVGXXXWPQLLLP-UHFFFAOYSA-N 0.000 description 2
- BPLBJDXWALACBD-UHFFFAOYSA-N 1,2,4-trichloro-5-fluorobenzene Chemical compound FC1=CC(Cl)=C(Cl)C=C1Cl BPLBJDXWALACBD-UHFFFAOYSA-N 0.000 description 2
- HVCOLMJHXJLJEZ-UHFFFAOYSA-N 1,2-dichloro-3-[dichloro(fluoro)methyl]benzene Chemical compound FC(Cl)(Cl)C1=CC=CC(Cl)=C1Cl HVCOLMJHXJLJEZ-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- QXDLANUKDLHQAH-UHFFFAOYSA-N 2,3-dichloro-6-(dichloromethyl)quinoxaline Chemical compound N1=C(Cl)C(Cl)=NC2=CC(C(Cl)Cl)=CC=C21 QXDLANUKDLHQAH-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- UWSAFTDEEVGSAC-UHFFFAOYSA-N 2,3-dichloro-6-methylquinoxaline Chemical compound N1=C(Cl)C(Cl)=NC2=CC(C)=CC=C21 UWSAFTDEEVGSAC-UHFFFAOYSA-N 0.000 description 1
- KZSNBJMYJWDVTK-UHFFFAOYSA-N 2,4-dichloro-1-(trichloromethyl)benzene Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C(Cl)=C1 KZSNBJMYJWDVTK-UHFFFAOYSA-N 0.000 description 1
- IGSFOXNHUBLZHU-UHFFFAOYSA-N 2,4-dichloro-5-methylaniline Chemical compound CC1=CC(N)=C(Cl)C=C1Cl IGSFOXNHUBLZHU-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- WFUBYPSJBBQSOU-UHFFFAOYSA-M rubidium iodide Inorganic materials [Rb+].[I-] WFUBYPSJBBQSOU-UHFFFAOYSA-M 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical class ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- VUNGRVUWQVLRQX-UHFFFAOYSA-N sulfurochloridic acid thionyl dichloride Chemical compound ClS(Cl)=O.OS(Cl)(=O)=O VUNGRVUWQVLRQX-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/62—Preparation of carboxylic acid halides by reactions not involving the carboxylic acid halide group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4133676A DE4133676A1 (de) | 1991-10-11 | 1991-10-11 | Verfahren zur radikalischen chlorierung oder bromierung von methylaromaten |
| TW081107142A TW234114B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-10-11 | 1992-09-10 | |
| EP92116539A EP0537540B1 (de) | 1991-10-11 | 1992-09-28 | Verfahren zur radikalischen Chlorierung oder Bromierung von Methylaromaten |
| ES92116539T ES2093750T3 (es) | 1991-10-11 | 1992-09-28 | Procedimiento para la cloracion o la bromacion mediante radicales de metilaromatos. |
| DK92116539.5T DK0537540T3 (da) | 1991-10-11 | 1992-09-28 | Fremgangsmåde til radikalisk chlorering eller bromering af methylaromater |
| DE59207429T DE59207429D1 (de) | 1991-10-11 | 1992-09-28 | Verfahren zur radikalischen Chlorierung oder Bromierung von Methylaromaten |
| US07/956,126 US5723613A (en) | 1991-10-11 | 1992-10-02 | Process for the free-radical chlorination or bromination of methyl aromatic compounds |
| JP04291981A JP3132923B2 (ja) | 1991-10-11 | 1992-10-07 | メチル芳香族化合物の遊離基塩素化または臭素化方法 |
| CA002080204A CA2080204A1 (en) | 1991-10-11 | 1992-10-08 | Process for the free-radical chlorination or bromination of methyl aromatic compounds |
| HU9203207A HU210669B (en) | 1991-10-11 | 1992-10-09 | Process for radical chlorination and bromination of methylated aromatic hydrocarbons |
| KR1019920018563A KR100243453B1 (ko) | 1991-10-11 | 1992-10-09 | 메틸 방향족 화합물의 자유-라디칼 염소화 또는 브롬화 방법 |
| IL10339592A IL103395A (en) | 1991-10-11 | 1992-10-09 | Chlorination or bromination of methyl aromatic compounds by free radicals |
| ZA927781A ZA927781B (en) | 1991-10-11 | 1992-10-09 | Process for the free-radical chlorination or bromination of methyl aromatic compounds. |
| GR960403221T GR3021830T3 (en) | 1991-10-11 | 1996-11-28 | Process for the radical chlorination or bromination of methyl substituted aromatics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4133676A DE4133676A1 (de) | 1991-10-11 | 1991-10-11 | Verfahren zur radikalischen chlorierung oder bromierung von methylaromaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4133676A1 true DE4133676A1 (de) | 1993-04-15 |
Family
ID=6442481
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4133676A Withdrawn DE4133676A1 (de) | 1991-10-11 | 1991-10-11 | Verfahren zur radikalischen chlorierung oder bromierung von methylaromaten |
| DE59207429T Expired - Fee Related DE59207429D1 (de) | 1991-10-11 | 1992-09-28 | Verfahren zur radikalischen Chlorierung oder Bromierung von Methylaromaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59207429T Expired - Fee Related DE59207429D1 (de) | 1991-10-11 | 1992-09-28 | Verfahren zur radikalischen Chlorierung oder Bromierung von Methylaromaten |
Country Status (13)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4313586A1 (de) * | 1993-04-26 | 1994-10-27 | Bayer Ag | Verfahren zur Herstellung von Chinoxalinen |
| EP1471639A1 (en) * | 2003-04-25 | 2004-10-27 | Alcatel | Active inductor |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3230268A (en) * | 1962-04-09 | 1966-01-18 | Fuso Chemical Co Ltd | Preparation of chloro-substituted benzene derivatives |
| US4046656A (en) * | 1976-12-06 | 1977-09-06 | The Dow Chemical Company | Photochlorination process for methyl aromatic compounds |
| DE3039884A1 (de) * | 1980-10-22 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | Trichlormethylchinoxaline, verfahren zu ihrer herstellung sowie ihre verwendung als zwischenprodukte bei der herstellung von reaktivkomponenten von reaktivfarbstoffen |
| DE3142856A1 (de) * | 1981-10-29 | 1983-05-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 2,4-dichlor-5-fluor-benzoylchlorid |
| DE3730476A1 (de) * | 1987-09-11 | 1989-03-23 | Bayer Ag | Herstellung von substituierten benzotrichloriden |
| JPH02240031A (ja) * | 1989-03-13 | 1990-09-25 | Sumitomo Seika Chem Co Ltd | α―クロロアルキル芳香族炭化水素の製造方法 |
-
1991
- 1991-10-11 DE DE4133676A patent/DE4133676A1/de not_active Withdrawn
-
1992
- 1992-09-10 TW TW081107142A patent/TW234114B/zh active
- 1992-09-28 DK DK92116539.5T patent/DK0537540T3/da active
- 1992-09-28 EP EP92116539A patent/EP0537540B1/de not_active Expired - Lifetime
- 1992-09-28 ES ES92116539T patent/ES2093750T3/es not_active Expired - Lifetime
- 1992-09-28 DE DE59207429T patent/DE59207429D1/de not_active Expired - Fee Related
- 1992-10-02 US US07/956,126 patent/US5723613A/en not_active Expired - Fee Related
- 1992-10-07 JP JP04291981A patent/JP3132923B2/ja not_active Expired - Fee Related
- 1992-10-08 CA CA002080204A patent/CA2080204A1/en not_active Abandoned
- 1992-10-09 IL IL10339592A patent/IL103395A/en not_active IP Right Cessation
- 1992-10-09 ZA ZA927781A patent/ZA927781B/xx unknown
- 1992-10-09 KR KR1019920018563A patent/KR100243453B1/ko not_active Expired - Fee Related
- 1992-10-09 HU HU9203207A patent/HU210669B/hu not_active IP Right Cessation
-
1996
- 1996-11-28 GR GR960403221T patent/GR3021830T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR930007868A (ko) | 1993-05-20 |
| HU210669B (en) | 1995-06-28 |
| EP0537540A1 (de) | 1993-04-21 |
| IL103395A0 (en) | 1993-03-15 |
| DE59207429D1 (de) | 1996-11-28 |
| TW234114B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-11-11 |
| JPH05271103A (ja) | 1993-10-19 |
| JP3132923B2 (ja) | 2001-02-05 |
| US5723613A (en) | 1998-03-03 |
| EP0537540B1 (de) | 1996-10-23 |
| IL103395A (en) | 1996-10-16 |
| DK0537540T3 (da) | 1997-03-24 |
| GR3021830T3 (en) | 1997-02-28 |
| HU9203207D0 (en) | 1992-12-28 |
| KR100243453B1 (ko) | 2000-02-01 |
| ZA927781B (en) | 1993-04-20 |
| ES2093750T3 (es) | 1997-01-01 |
| HUT62847A (en) | 1993-06-28 |
| CA2080204A1 (en) | 1993-04-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |