DE2449285A1 - Verfahren zur herstellung von chlorierten aromatischen aminen - Google Patents
Verfahren zur herstellung von chlorierten aromatischen aminenInfo
- Publication number
- DE2449285A1 DE2449285A1 DE19742449285 DE2449285A DE2449285A1 DE 2449285 A1 DE2449285 A1 DE 2449285A1 DE 19742449285 DE19742449285 DE 19742449285 DE 2449285 A DE2449285 A DE 2449285A DE 2449285 A1 DE2449285 A1 DE 2449285A1
- Authority
- DE
- Germany
- Prior art keywords
- chlorinated
- chlorination
- amines
- chlorine
- alkoxy
- 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- Withdrawn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 13
- 150000004982 aromatic amines Chemical class 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001412 amines Chemical class 0.000 claims description 17
- 238000005660 chlorination reaction Methods 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000725 suspension Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 4
- 150000001448 anilines Chemical class 0.000 claims description 3
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 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
- 238000004508 fractional distillation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 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
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase 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
- 239000007858 starting material Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RZQIWOXUOIBGEH-UHFFFAOYSA-N (2,4,6-trichlorophenyl)azanium;chloride Chemical compound Cl.NC1=C(Cl)C=C(Cl)C=C1Cl RZQIWOXUOIBGEH-UHFFFAOYSA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical class CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
- IRTONKUCLPTRNS-UHFFFAOYSA-N 2-butoxyaniline Chemical compound CCCCOC1=CC=CC=C1N IRTONKUCLPTRNS-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- BPEXTIMJLDWDTL-UHFFFAOYSA-N 2`-Methylacetanilide Chemical compound CC(=O)NC1=CC=CC=C1C BPEXTIMJLDWDTL-UHFFFAOYSA-N 0.000 description 1
- WOXLPNAOCCIZGP-UHFFFAOYSA-N 4-chloro-2-methoxyaniline Chemical compound COC1=CC(Cl)=CC=C1N WOXLPNAOCCIZGP-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 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
- MKDHTPTXOKJEFU-UHFFFAOYSA-N [N].Cl Chemical compound [N].Cl MKDHTPTXOKJEFU-UHFFFAOYSA-N 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
- 150000001447 alkali salts Chemical class 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 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
- 239000000975 dye Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- NUJAPVSRDGSINW-UHFFFAOYSA-N n'-phenylmethanediamine Chemical compound NCNC1=CC=CC=C1 NUJAPVSRDGSINW-UHFFFAOYSA-N 0.000 description 1
- OPEQDESZXVNCJC-UHFFFAOYSA-N n-(2-chloroethoxy)aniline Chemical compound ClCCONC1=CC=CC=C1 OPEQDESZXVNCJC-UHFFFAOYSA-N 0.000 description 1
- KTDILAZSFSAPMD-UHFFFAOYSA-N n-(2-chloroethyl)aniline Chemical compound ClCCNC1=CC=CC=C1 KTDILAZSFSAPMD-UHFFFAOYSA-N 0.000 description 1
- OXHJCNSXYDSOFN-UHFFFAOYSA-N n-hexylaniline Chemical compound CCCCCCNC1=CC=CC=C1 OXHJCNSXYDSOFN-UHFFFAOYSA-N 0.000 description 1
- RNRDHZGWBBEZBK-UHFFFAOYSA-N n-methyl-2-(trifluoromethyl)aniline Chemical compound CNC1=CC=CC=C1C(F)(F)F RNRDHZGWBBEZBK-UHFFFAOYSA-N 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 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
- 238000010926 purge Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742449285 DE2449285A1 (de) | 1974-10-16 | 1974-10-16 | Verfahren zur herstellung von chlorierten aromatischen aminen |
| NL7511941A NL7511941A (nl) | 1974-10-16 | 1975-10-10 | Werkwijze voor het bereiden van gechloreerde aro- matische aminen. |
| IT2827175A IT1043358B (it) | 1974-10-16 | 1975-10-14 | Processo per la preparazione di amine aromatiche clorurate |
| JP12335075A JPS5165721A (ja) | 1974-10-16 | 1975-10-15 | Ensokasaretahokozokuaminno seiho |
| FR7531510A FR2288083A1 (fr) | 1974-10-16 | 1975-10-15 | Procede de preparation d'amines aromatiques chlorees |
| GB4256875A GB1521136A (en) | 1974-10-16 | 1975-10-16 | Chlorination of aromatic amines and their derivatives |
| BE160996A BE834579A (fr) | 1974-10-16 | 1975-10-16 | Procede de preparation d'amines aromatiques chlorees |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742449285 DE2449285A1 (de) | 1974-10-16 | 1974-10-16 | Verfahren zur herstellung von chlorierten aromatischen aminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2449285A1 true DE2449285A1 (de) | 1976-04-22 |
Family
ID=5928447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742449285 Withdrawn DE2449285A1 (de) | 1974-10-16 | 1974-10-16 | Verfahren zur herstellung von chlorierten aromatischen aminen |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5165721A (enExample) |
| BE (1) | BE834579A (enExample) |
| DE (1) | DE2449285A1 (enExample) |
| FR (1) | FR2288083A1 (enExample) |
| GB (1) | GB1521136A (enExample) |
| IT (1) | IT1043358B (enExample) |
| NL (1) | NL7511941A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0083442A3 (en) * | 1982-01-05 | 1985-04-17 | Bayer Ag | Process for the production of 2,4,6-trichloroaniline |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3043206A1 (de) * | 1980-11-15 | 1982-07-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 4-chlor-2,6-dialkylanilinen |
| 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 |
| US4918230A (en) * | 1988-06-14 | 1990-04-17 | Ciba-Geigy Corporation | Process for the preparation 4-bromoaniline hydrobromides |
| US9193667B2 (en) * | 2010-08-20 | 2015-11-24 | Lonza Ltd. | Process for the selective meta-chlorination of alkylanilines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2319645C3 (de) * | 1973-04-18 | 1978-12-07 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von 5-Chlor-2-toluidin |
-
1974
- 1974-10-16 DE DE19742449285 patent/DE2449285A1/de not_active Withdrawn
-
1975
- 1975-10-10 NL NL7511941A patent/NL7511941A/xx not_active Application Discontinuation
- 1975-10-14 IT IT2827175A patent/IT1043358B/it active
- 1975-10-15 JP JP12335075A patent/JPS5165721A/ja active Pending
- 1975-10-15 FR FR7531510A patent/FR2288083A1/fr active Granted
- 1975-10-16 GB GB4256875A patent/GB1521136A/en not_active Expired
- 1975-10-16 BE BE160996A patent/BE834579A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0083442A3 (en) * | 1982-01-05 | 1985-04-17 | Bayer Ag | Process for the production of 2,4,6-trichloroaniline |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2288083A1 (fr) | 1976-05-14 |
| FR2288083B1 (enExample) | 1979-01-05 |
| NL7511941A (nl) | 1976-04-21 |
| GB1521136A (en) | 1978-08-16 |
| BE834579A (fr) | 1976-04-16 |
| IT1043358B (it) | 1980-02-20 |
| JPS5165721A (ja) | 1976-06-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |