DE68910912T2 - Herstellung von Pyridazinon. - Google Patents
Herstellung von Pyridazinon.Info
- Publication number
- DE68910912T2 DE68910912T2 DE89308761T DE68910912T DE68910912T2 DE 68910912 T2 DE68910912 T2 DE 68910912T2 DE 89308761 T DE89308761 T DE 89308761T DE 68910912 T DE68910912 T DE 68910912T DE 68910912 T2 DE68910912 T2 DE 68910912T2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- sulfuric acid
- formula
- pyridazine
- manufacture
- 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 - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 3
- 235000011149 sulphuric acid Nutrition 0.000 abstract description 3
- 239000001117 sulphuric acid Substances 0.000 abstract description 2
- BAFCNWHOZHAYGE-UHFFFAOYSA-N 4-oxo-3h-pyridazine-3,5-dicarboxylic acid Chemical compound OC(=O)C1N=NC=C(C(O)=O)C1=O BAFCNWHOZHAYGE-UHFFFAOYSA-N 0.000 abstract 1
- QJJQVVAYNHEGFH-UHFFFAOYSA-N 4-oxo-3h-pyridazine-3-carboxylic acid Chemical class OC(=O)C1N=NC=CC1=O QJJQVVAYNHEGFH-UHFFFAOYSA-N 0.000 abstract 1
- IUIPYGPGINJGBK-UHFFFAOYSA-N 4-oxo-3h-pyridazine-5-carboxylic acid Chemical compound OC(=O)C1=CN=NCC1=O IUIPYGPGINJGBK-UHFFFAOYSA-N 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000006149 azo coupling reaction Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- PIZCXVUFSNPNON-UHFFFAOYSA-N clofencet Chemical compound CCC1=C(C(O)=O)C(=O)C=NN1C1=CC=C(Cl)C=C1 PIZCXVUFSNPNON-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000003269 fluorescent indicator Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (2)
1. Verfahren zur Herstellung einer Monocarbonsäure der
Formel (IV)
aus einer Dicarbonsäure der Formel (V),
worin R&sup6; für C&sub1;&submin;&sub6;-Alkyl und X für Monochloro steht, dadurch
gekennzeichnet, daß die Verbindung (V) mit 95 bis 100 %iger
Schwefelsäure so lange auf eine Temperatur im Bereich von
160 bis 180ºC erhitzt wird, daß eine zumindest 70 %ige
Monodecarboxylierung erreicht wird, wobei das verwendete
Gewichtsverhältnis (V) zu Schwefelsäure im Bereich von 1:5 bis 1:8
liegt.
2. Verfahren nach Anspruch 1, bei welchem Schwefelsäure
einer Konzentration von 98 % verwendet wird.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB888821449A GB8821449D0 (en) | 1988-09-13 | 1988-09-13 | Pyridazinone manufacture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE68910912D1 DE68910912D1 (de) | 1994-01-05 |
| DE68910912T2 true DE68910912T2 (de) | 1994-03-17 |
Family
ID=10643514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE89308761T Expired - Fee Related DE68910912T2 (de) | 1988-09-13 | 1989-08-30 | Herstellung von Pyridazinon. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5010192A (de) |
| EP (1) | EP0359438B1 (de) |
| JP (1) | JP2774834B2 (de) |
| AT (1) | ATE97661T1 (de) |
| AU (1) | AU634488B2 (de) |
| CA (1) | CA1313374C (de) |
| DE (1) | DE68910912T2 (de) |
| ES (1) | ES2062020T3 (de) |
| GB (1) | GB8821449D0 (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8821447D0 (en) * | 1988-09-13 | 1988-10-12 | Ici Plc | Pyridazinone manufacture |
| GB8919622D0 (en) * | 1989-08-30 | 1989-10-11 | Ici Plc | A method of preparing pyridazinone derivatives |
| US5189163A (en) * | 1989-08-30 | 1993-02-23 | Imperial Chemical Industries Plc | Method of preparing pyridazinone derivatives |
| CN1348457A (zh) | 1999-02-02 | 2002-05-08 | 孟山都技术有限公司 | 膦酰基吡唑的生产 |
| EP2052612A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037629A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4345934A (en) * | 1977-03-10 | 1982-08-24 | Rohm And Haas Company | Method of producing hybrid cereal grain seeds by application of 1-aryl-1,4-dihydro-4-oxo(thio)-pyridazines |
| GR75799B (de) * | 1980-10-03 | 1984-08-02 | Ici Plc | |
| US4732603A (en) * | 1980-10-03 | 1988-03-22 | Rohm And Haas Company | 1-aryl-1,4-dihydro-4-oxo-5-carboxypyridazine derivatives and their use as plant growth regulators and hybridizing agents |
| US4623378A (en) * | 1983-08-10 | 1986-11-18 | Ciba-Geigy Corporation | Gametocidal pyridazinylcarboxylic acid derivatives |
-
1988
- 1988-09-13 GB GB888821449A patent/GB8821449D0/en active Pending
-
1989
- 1989-08-30 EP EP89308761A patent/EP0359438B1/de not_active Expired - Lifetime
- 1989-08-30 DE DE89308761T patent/DE68910912T2/de not_active Expired - Fee Related
- 1989-08-30 AT AT89308761T patent/ATE97661T1/de not_active IP Right Cessation
- 1989-08-30 ES ES89308761T patent/ES2062020T3/es not_active Expired - Lifetime
- 1989-09-12 CA CA000611368A patent/CA1313374C/en not_active Expired - Fee Related
- 1989-09-13 AU AU41377/89A patent/AU634488B2/en not_active Ceased
- 1989-09-13 US US07/406,338 patent/US5010192A/en not_active Expired - Fee Related
- 1989-09-13 JP JP1238322A patent/JP2774834B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU4137789A (en) | 1990-03-22 |
| GB8821449D0 (en) | 1988-10-12 |
| AU634488B2 (en) | 1993-02-25 |
| ATE97661T1 (de) | 1993-12-15 |
| US5010192A (en) | 1991-04-23 |
| JP2774834B2 (ja) | 1998-07-09 |
| EP0359438B1 (de) | 1993-11-24 |
| DE68910912D1 (de) | 1994-01-05 |
| EP0359438A1 (de) | 1990-03-21 |
| JPH02131471A (ja) | 1990-05-21 |
| ES2062020T3 (es) | 1994-12-16 |
| CA1313374C (en) | 1993-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: AVECIA LTD., BLACKLEY, MANCHESTER, GB |
|
| 8339 | Ceased/non-payment of the annual fee |