DD154016A5 - Verfahren zur herstellung von 4-chlor-5-amino-2-phenyl-3(2h)-pyridazinon aus 4,5-dichlor-2-phenyl-3(2h)-pyridazinon und ammoniak - Google Patents
Verfahren zur herstellung von 4-chlor-5-amino-2-phenyl-3(2h)-pyridazinon aus 4,5-dichlor-2-phenyl-3(2h)-pyridazinon und ammoniak Download PDFInfo
- Publication number
- DD154016A5 DD154016A5 DD80224876A DD22487680A DD154016A5 DD 154016 A5 DD154016 A5 DD 154016A5 DD 80224876 A DD80224876 A DD 80224876A DD 22487680 A DD22487680 A DD 22487680A DD 154016 A5 DD154016 A5 DD 154016A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- phenyl
- pyridazinone
- chloro
- catalyst
- amino
- Prior art date
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 title claims abstract description 41
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 229910021529 ammonia Inorganic materials 0.000 title claims abstract description 18
- VKWCOHVAHQOJGU-UHFFFAOYSA-N 4,5-dichloro-2-phenylpyridazin-3-one Chemical compound O=C1C(Cl)=C(Cl)C=NN1C1=CC=CC=C1 VKWCOHVAHQOJGU-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012429 reaction media Substances 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 239000012452 mother liquor Substances 0.000 claims abstract description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- HAKJEHJYRKVCIU-UHFFFAOYSA-N 4-amino-5-chloro-2-phenylpyridazin-3-one Chemical compound O=C1C(N)=C(Cl)C=NN1C1=CC=CC=C1 HAKJEHJYRKVCIU-UHFFFAOYSA-N 0.000 claims abstract description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 10
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 9
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims description 6
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- -1 phenol compound Chemical class 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 abstract description 2
- 230000001172 regenerating effect Effects 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- BFOMTEBFEFQJHY-UHFFFAOYSA-N 2-phenylpyridazin-3-one Chemical compound O=C1C=CC=NN1C1=CC=CC=C1 BFOMTEBFEFQJHY-UHFFFAOYSA-N 0.000 description 1
- VJWXIRQLLGYIDI-UHFFFAOYSA-N 4,5-dichloro-1h-pyridazin-6-one Chemical class OC1=NN=CC(Cl)=C1Cl VJWXIRQLLGYIDI-UHFFFAOYSA-N 0.000 description 1
- 241001026509 Kata Species 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D237/22—Nitrogen and oxygen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK461379 | 1979-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD154016A5 true DD154016A5 (de) | 1982-02-17 |
Family
ID=8135124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80224876A DD154016A5 (de) | 1979-10-31 | 1980-10-31 | Verfahren zur herstellung von 4-chlor-5-amino-2-phenyl-3(2h)-pyridazinon aus 4,5-dichlor-2-phenyl-3(2h)-pyridazinon und ammoniak |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4454318A (en, 2012) |
| EP (1) | EP0028359B1 (en, 2012) |
| JP (1) | JPS56501486A (en, 2012) |
| AT (1) | ATE7026T1 (en, 2012) |
| CS (1) | CS219294B2 (en, 2012) |
| DD (1) | DD154016A5 (en, 2012) |
| DE (1) | DE3067461D1 (en, 2012) |
| DK (1) | DK150066C (en, 2012) |
| FI (1) | FI63024C (en, 2012) |
| IL (1) | IL61312A (en, 2012) |
| RO (1) | RO81924A (en, 2012) |
| UA (1) | UA7026A1 (en, 2012) |
| WO (1) | WO1981001288A1 (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3926905A1 (de) * | 1989-08-16 | 1991-02-21 | Basf Ag | Verfahren zur abtrennung und wiederverwertung von reststoffen aus dem abwasser der synthese von 5-amino-4-chlor-2-phenyl-3(2h)-pyridazinon |
| AU771700B2 (en) | 1999-03-31 | 2004-04-01 | Basf Aktiengesellschaft | Method for producing 4-amino-5-chloro-1-phenyl pyridazinone-(6) |
| JP2003231380A (ja) | 2002-02-12 | 2003-08-19 | Nhk Spring Co Ltd | 対象物の識別媒体及び識別方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL245646A (en, 2012) * | 1960-03-19 | |||
| AT247355B (de) * | 1964-06-03 | 1966-06-10 | Basf Ag | Verfahren zur Herstellung von 1-Phenyl-4-amino-5-chlor-pyridazon-(6) |
| DE1620150A1 (de) * | 1965-03-19 | 1972-04-06 | Pavel Raposh | Verfahren zur Herstellung von Pyridazonen |
| FR1575643A (en, 2012) * | 1968-03-28 | 1969-07-25 | ||
| DE2100685C2 (de) * | 1971-01-08 | 1983-09-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von reinen 4-Amino-5-halogen-pyridazonen-(6) |
| CS153812B1 (en, 2012) * | 1971-01-15 | 1974-03-29 | ||
| CS158843B1 (en, 2012) * | 1972-04-17 | 1974-12-27 | ||
| HU169505B (en, 2012) * | 1974-05-22 | 1976-12-28 | ||
| DE2937421A1 (de) * | 1979-09-15 | 1981-04-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 4-amino-5-chlor-1-phenylpyridazon-(6) |
-
1980
- 1980-10-17 JP JP50257780A patent/JPS56501486A/ja active Pending
- 1980-10-17 RO RO80103691A patent/RO81924A/ro unknown
- 1980-10-17 US US06/253,840 patent/US4454318A/en not_active Expired - Lifetime
- 1980-10-17 UA UA3304332A patent/UA7026A1/uk unknown
- 1980-10-17 WO PCT/DK1980/000062 patent/WO1981001288A1/en active IP Right Grant
- 1980-10-20 IL IL61312A patent/IL61312A/xx not_active IP Right Cessation
- 1980-10-22 DE DE8080106446T patent/DE3067461D1/de not_active Expired
- 1980-10-22 AT AT80106446T patent/ATE7026T1/de not_active IP Right Cessation
- 1980-10-22 EP EP80106446A patent/EP0028359B1/en not_active Expired
- 1980-10-29 CS CS807318A patent/CS219294B2/cs unknown
- 1980-10-31 DD DD80224876A patent/DD154016A5/de not_active IP Right Cessation
-
1981
- 1981-03-16 DK DK118081A patent/DK150066C/da not_active IP Right Cessation
- 1981-03-26 FI FI810936A patent/FI63024C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| UA7026A1 (uk) | 1995-03-31 |
| IL61312A (en) | 1984-11-30 |
| JPS56501486A (en, 2012) | 1981-10-15 |
| IL61312A0 (en) | 1980-12-31 |
| EP0028359A1 (en) | 1981-05-13 |
| EP0028359B1 (en) | 1984-04-11 |
| FI810936L (fi) | 1981-05-01 |
| DE3067461D1 (en) | 1984-05-17 |
| DK150066B (da) | 1986-12-01 |
| ATE7026T1 (de) | 1984-04-15 |
| RO81924A (ro) | 1984-05-12 |
| DK150066C (da) | 1987-06-29 |
| DK118081A (da) | 1981-05-14 |
| US4454318A (en) | 1984-06-12 |
| WO1981001288A1 (en) | 1981-05-14 |
| CS219294B2 (en) | 1983-03-25 |
| FI63024C (fi) | 1983-04-11 |
| FI63024B (fi) | 1982-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |