DD210030A5 - Verfahren zur herstellung gegebenenfalls halogenierter aniline - Google Patents
Verfahren zur herstellung gegebenenfalls halogenierter aniline Download PDFInfo
- Publication number
- DD210030A5 DD210030A5 DD83252467A DD25246783A DD210030A5 DD 210030 A5 DD210030 A5 DD 210030A5 DD 83252467 A DD83252467 A DD 83252467A DD 25246783 A DD25246783 A DD 25246783A DD 210030 A5 DD210030 A5 DD 210030A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- copper
- hydroxyquinoline
- formula
- items
- complexing agent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000010949 copper Substances 0.000 claims abstract description 17
- 229910052802 copper Inorganic materials 0.000 claims abstract description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims abstract description 10
- 229960003540 oxyquinoline Drugs 0.000 claims abstract description 10
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 150000004325 8-hydroxyquinolines Chemical class 0.000 claims abstract description 5
- 150000001448 anilines Chemical class 0.000 claims abstract description 5
- 239000008139 complexing agent Substances 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 16
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 8
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 8
- 150000005171 halobenzenes Chemical class 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 238000005915 ammonolysis reaction Methods 0.000 claims description 6
- -1 Tetramethylharnstcff Chemical compound 0.000 claims description 4
- LGDFHDKSYGVKDC-UHFFFAOYSA-N 8-hydroxyquinoline-5-sulfonic acid Chemical compound C1=CN=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 LGDFHDKSYGVKDC-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 abstract description 8
- 229910021529 ammonia Inorganic materials 0.000 abstract description 6
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 27
- XKEFYDZQGKAQCN-UHFFFAOYSA-N 1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1 XKEFYDZQGKAQCN-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 7
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 5
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 230000000536 complexating effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WOAOKCGYVUEWAR-UHFFFAOYSA-M C(C)O.OC=1C=CC=C2C=CC=NC12.[Cu]Cl Chemical compound C(C)O.OC=1C=CC=C2C=CC=NC12.[Cu]Cl WOAOKCGYVUEWAR-UHFFFAOYSA-M 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- YAHQXRHYYNBHTD-UHFFFAOYSA-N NC(N)=S.N1=CC=CC2=CC=CC=C21 Chemical compound NC(N)=S.N1=CC=CC2=CC=CC=C21 YAHQXRHYYNBHTD-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 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
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- DXPADZGWFZQNIJ-UHFFFAOYSA-N quinolin-8-ol;1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C.C1=CN=C2C(O)=CC=CC2=C1 DXPADZGWFZQNIJ-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
- C07C211/56—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
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)
- Catalysts (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8211617A FR2529198A1 (fr) | 1982-06-29 | 1982-06-29 | Procede de preparation de halogeno-anilines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD210030A5 true DD210030A5 (de) | 1984-05-30 |
Family
ID=9275617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD83252467A DD210030A5 (de) | 1982-06-29 | 1983-06-28 | Verfahren zur herstellung gegebenenfalls halogenierter aniline |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4508922A (en, 2012) |
| EP (1) | EP0098783B1 (en, 2012) |
| JP (1) | JPS5913750A (en, 2012) |
| KR (1) | KR910004664B1 (en, 2012) |
| AT (1) | ATE15030T1 (en, 2012) |
| BR (1) | BR8303461A (en, 2012) |
| CA (1) | CA1209589A (en, 2012) |
| DD (1) | DD210030A5 (en, 2012) |
| DE (1) | DE3360611D1 (en, 2012) |
| DK (1) | DK161069C (en, 2012) |
| ES (1) | ES8407003A1 (en, 2012) |
| FR (1) | FR2529198A1 (en, 2012) |
| HU (1) | HU190495B (en, 2012) |
| IE (1) | IE55548B1 (en, 2012) |
| IL (1) | IL68943A0 (en, 2012) |
| ZA (1) | ZA834690B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993003002A1 (en) * | 1991-08-06 | 1993-02-18 | Mallinckrodt Specialty Chemicals Company | Production of fluoro-aromatic amines |
| DE19720341C1 (de) * | 1997-05-15 | 1998-08-27 | Clariant Gmbh | Verfahren zur Herstellung von 3,5-Difluoranilin |
| GB9911180D0 (en) | 1999-05-13 | 1999-07-14 | Rhone Poulenc Agrochimie | Processes for preparing pesticidal intermediates |
| CN105085277A (zh) * | 2014-05-22 | 2015-11-25 | 江苏扬农化工集团有限公司 | 一种制备2,3-/2,6-二氯苯胺的方法 |
| JP6182507B2 (ja) * | 2014-05-30 | 2017-08-16 | 日本曹達株式会社 | ２，３−ジハロゲノアニリンの製造方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2159370A (en) * | 1937-03-29 | 1939-05-23 | Dow Chemical Co | Manufacture of nuclear alkylated anilines |
| US2678314A (en) * | 1950-12-04 | 1954-05-11 | Monsanto Chemicals | 8-hydroxy quinoline and metal salts thereof |
| US3637711A (en) * | 1968-03-25 | 1972-01-25 | Ashland Oil Inc | Beta-alkenyl substituted 8-hydroxyquinolines |
| JPS4980404U (en, 2012) * | 1972-10-27 | 1974-07-11 | ||
| JPS4993002U (en, 2012) * | 1972-11-30 | 1974-08-12 | ||
| US4117013A (en) * | 1976-06-23 | 1978-09-26 | United Technologies Corporation | Catalysts for the ammonolysis of pentaerythrityl tetrachloride |
| JPS5364310U (en, 2012) * | 1976-11-02 | 1978-05-30 | ||
| DE2720316C2 (de) * | 1977-05-06 | 1982-04-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 3,5-Dihalogenanilinen |
| JPS5418709U (en, 2012) * | 1977-07-11 | 1979-02-06 |
-
1982
- 1982-06-29 FR FR8211617A patent/FR2529198A1/fr active Granted
-
1983
- 1983-06-09 IL IL68943A patent/IL68943A0/xx not_active IP Right Cessation
- 1983-06-15 KR KR1019830002666A patent/KR910004664B1/ko not_active Expired
- 1983-06-21 EP EP83420103A patent/EP0098783B1/fr not_active Expired
- 1983-06-21 AT AT83420103T patent/ATE15030T1/de not_active IP Right Cessation
- 1983-06-21 DE DE8383420103T patent/DE3360611D1/de not_active Expired
- 1983-06-27 IE IE1493/83A patent/IE55548B1/en not_active IP Right Cessation
- 1983-06-27 CA CA000431209A patent/CA1209589A/en not_active Expired
- 1983-06-27 ZA ZA834690A patent/ZA834690B/xx unknown
- 1983-06-28 DD DD83252467A patent/DD210030A5/de unknown
- 1983-06-28 JP JP58116831A patent/JPS5913750A/ja active Granted
- 1983-06-28 ES ES523638A patent/ES8407003A1/es not_active Expired
- 1983-06-28 US US06/508,716 patent/US4508922A/en not_active Expired - Fee Related
- 1983-06-28 BR BR8303461A patent/BR8303461A/pt not_active IP Right Cessation
- 1983-06-28 DK DK297183A patent/DK161069C/da not_active IP Right Cessation
- 1983-06-29 HU HU832363A patent/HU190495B/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0098783B1 (fr) | 1985-08-21 |
| ES523638A0 (es) | 1984-08-16 |
| JPS5913750A (ja) | 1984-01-24 |
| ZA834690B (en) | 1984-03-28 |
| DK161069B (da) | 1991-05-27 |
| HU190495B (en) | 1986-09-29 |
| DK161069C (da) | 1991-11-18 |
| KR910004664B1 (ko) | 1991-07-09 |
| BR8303461A (pt) | 1984-02-07 |
| IE831493L (en) | 1983-12-29 |
| ES8407003A1 (es) | 1984-08-16 |
| JPH0258253B2 (en, 2012) | 1990-12-07 |
| IL68943A0 (en) | 1983-10-31 |
| FR2529198A1 (fr) | 1983-12-30 |
| DK297183A (da) | 1983-12-30 |
| ATE15030T1 (de) | 1985-09-15 |
| KR840005072A (ko) | 1984-11-03 |
| FR2529198B1 (en, 2012) | 1985-03-29 |
| US4508922A (en) | 1985-04-02 |
| DE3360611D1 (en) | 1985-09-26 |
| IE55548B1 (en) | 1990-10-24 |
| EP0098783A1 (fr) | 1984-01-18 |
| CA1209589A (en) | 1986-08-12 |
| DK297183D0 (da) | 1983-06-28 |
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