DE2319645C3 - Verfahren zur Herstellung von 5-Chlor-2-toluidin - Google Patents
Verfahren zur Herstellung von 5-Chlor-2-toluidinInfo
- Publication number
- DE2319645C3 DE2319645C3 DE2319645A DE2319645A DE2319645C3 DE 2319645 C3 DE2319645 C3 DE 2319645C3 DE 2319645 A DE2319645 A DE 2319645A DE 2319645 A DE2319645 A DE 2319645A DE 2319645 C3 DE2319645 C3 DE 2319645C3
- Authority
- DE
- Germany
- Prior art keywords
- toluidine
- chloro
- chlorination
- hydrochloride
- preparation
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 11
- WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 6
- 238000005660 chlorination reaction Methods 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- SHLTXWFNRJQZTQ-UHFFFAOYSA-N n-chloro-2-methylaniline Chemical compound CC1=CC=CC=C1NCl SHLTXWFNRJQZTQ-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000251730 Chondrichthyes Species 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 150000004992 toluidines Chemical class 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- OTCBGVAURJAJSJ-UHFFFAOYSA-N 3,5-dichloro-2-methylaniline Chemical compound CC1=C(N)C=C(Cl)C=C1Cl OTCBGVAURJAJSJ-UHFFFAOYSA-N 0.000 description 1
- ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 description 1
- -1 B. Saline Chemical compound 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- OGVXWEOZQMAAIM-UHFFFAOYSA-N hydron;2-methylaniline;chloride Chemical compound Cl.CC1=CC=CC=C1N OGVXWEOZQMAAIM-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2319645A DE2319645C3 (de) | 1973-04-18 | 1973-04-18 | Verfahren zur Herstellung von 5-Chlor-2-toluidin |
| GB1545274A GB1463618A (en) | 1973-04-18 | 1974-04-08 | Process for the preparation of 5-chloro-2-toluidine |
| NL7405000A NL7405000A (enExample) | 1973-04-18 | 1974-04-11 | |
| CH513074A CH589039A5 (enExample) | 1973-04-18 | 1974-04-11 | |
| IT21464/74A IT1009850B (it) | 1973-04-18 | 1974-04-16 | Processo per la preparazione di 5 cloro 2 toluidina |
| JP49041862A JPS505337A (enExample) | 1973-04-18 | 1974-04-16 | |
| US05/461,453 US3962336A (en) | 1973-04-18 | 1974-04-16 | Process for the preparation of 5-chloro-2-toluidine |
| CA197,655A CA1014974A (en) | 1973-04-18 | 1974-04-17 | Process for the preparation of 5-chloro-2-toluidine |
| FR7413492A FR2226385B1 (enExample) | 1973-04-18 | 1974-04-18 | |
| BE143370A BE813908A (fr) | 1973-04-18 | 1974-04-18 | Procede de preparation de la 5-chloro-2-toluidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2319645A DE2319645C3 (de) | 1973-04-18 | 1973-04-18 | Verfahren zur Herstellung von 5-Chlor-2-toluidin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2319645A1 DE2319645A1 (de) | 1974-11-14 |
| DE2319645B2 DE2319645B2 (de) | 1978-04-13 |
| DE2319645C3 true DE2319645C3 (de) | 1978-12-07 |
Family
ID=5878510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2319645A Expired DE2319645C3 (de) | 1973-04-18 | 1973-04-18 | Verfahren zur Herstellung von 5-Chlor-2-toluidin |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3962336A (enExample) |
| JP (1) | JPS505337A (enExample) |
| BE (1) | BE813908A (enExample) |
| CA (1) | CA1014974A (enExample) |
| CH (1) | CH589039A5 (enExample) |
| DE (1) | DE2319645C3 (enExample) |
| FR (1) | FR2226385B1 (enExample) |
| GB (1) | GB1463618A (enExample) |
| IT (1) | IT1009850B (enExample) |
| NL (1) | NL7405000A (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU31834B (en) * | 1967-08-01 | 1973-12-31 | Kemper Kg Wilhelm | Masina za zetvu kukuruza ili slicnih stabljicastih kultura |
| DE2449285A1 (de) * | 1974-10-16 | 1976-04-22 | Hoechst Ag | Verfahren zur herstellung von chlorierten aromatischen aminen |
| JPS54125636A (en) * | 1978-03-20 | 1979-09-29 | Dainichi Seika Kogyo Kk | Preparation of 6-chloro-3-toluiding-4-sulfonic acid |
| JPS6045551A (ja) * | 1983-08-23 | 1985-03-12 | Tokuyama Soda Co Ltd | トリクロルアニリンの製造方法 |
| US4772747A (en) * | 1983-10-28 | 1988-09-20 | Eastman Kodak Company | Preparation of 2,4,6-trichlorophenylhydrazine |
| US4918230A (en) * | 1988-06-14 | 1990-04-17 | Ciba-Geigy Corporation | Process for the preparation 4-bromoaniline hydrobromides |
| WO2012022460A1 (en) | 2010-08-20 | 2012-02-23 | Lonza Ltd | Process for the selective meta-chlorination of alkylanilines |
| WO2012048845A1 (en) * | 2010-10-14 | 2012-04-19 | Lonza Ltd | Halogenated diethyltoluenediamines |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1930751A (en) * | 1931-04-20 | 1933-10-17 | Du Pont | Chlorination of omicron-toluidine |
| US1930752A (en) * | 1932-01-25 | 1933-10-17 | Du Pont | Chlorination of p-xylidine |
| US2675409A (en) * | 1952-01-04 | 1954-04-13 | Ethyl Corp | Preparation of 2, 4, 6-trichloroaniline |
-
1973
- 1973-04-18 DE DE2319645A patent/DE2319645C3/de not_active Expired
-
1974
- 1974-04-08 GB GB1545274A patent/GB1463618A/en not_active Expired
- 1974-04-11 CH CH513074A patent/CH589039A5/xx not_active IP Right Cessation
- 1974-04-11 NL NL7405000A patent/NL7405000A/xx not_active Application Discontinuation
- 1974-04-16 JP JP49041862A patent/JPS505337A/ja active Pending
- 1974-04-16 US US05/461,453 patent/US3962336A/en not_active Expired - Lifetime
- 1974-04-16 IT IT21464/74A patent/IT1009850B/it active
- 1974-04-17 CA CA197,655A patent/CA1014974A/en not_active Expired
- 1974-04-18 BE BE143370A patent/BE813908A/xx unknown
- 1974-04-18 FR FR7413492A patent/FR2226385B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE813908A (fr) | 1974-10-18 |
| DE2319645A1 (de) | 1974-11-14 |
| CH589039A5 (enExample) | 1977-06-30 |
| IT1009850B (it) | 1976-12-20 |
| JPS505337A (enExample) | 1975-01-21 |
| GB1463618A (en) | 1977-02-02 |
| FR2226385B1 (enExample) | 1977-10-14 |
| US3962336A (en) | 1976-06-08 |
| CA1014974A (en) | 1977-08-02 |
| DE2319645B2 (de) | 1978-04-13 |
| FR2226385A1 (enExample) | 1974-11-15 |
| NL7405000A (enExample) | 1974-10-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |