DE2558399C3 - Verfahren zur Herstellung von 3,6-Dichlorpicolinsäure - Google Patents
Verfahren zur Herstellung von 3,6-DichlorpicolinsäureInfo
- Publication number
- DE2558399C3 DE2558399C3 DE2558399A DE2558399A DE2558399C3 DE 2558399 C3 DE2558399 C3 DE 2558399C3 DE 2558399 A DE2558399 A DE 2558399A DE 2558399 A DE2558399 A DE 2558399A DE 2558399 C3 DE2558399 C3 DE 2558399C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- dichloropicolinic
- dichloropicolinic acid
- preparation
- water
- 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 10
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000012429 reaction media Substances 0.000 claims description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229940035339 tri-chlor Drugs 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KBWNOFMJVVPCQQ-UHFFFAOYSA-N 3,5,6-trichloro-4-hydrazinylpyridine-2-carboxylic acid Chemical compound NNC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl KBWNOFMJVVPCQQ-UHFFFAOYSA-N 0.000 description 2
- MWFCRQNUHFSUNY-UHFFFAOYSA-N 3,6-dichloro-2-(trichloromethyl)pyridine Chemical compound ClC1=CC=C(Cl)C(C(Cl)(Cl)Cl)=N1 MWFCRQNUHFSUNY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000238631 Hexapoda Species 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
- 241001124553 Lepismatidae Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salt Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Inorganic materials [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53678874A | 1974-12-27 | 1974-12-27 | |
| US53678974A | 1974-12-27 | 1974-12-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2558399A1 DE2558399A1 (de) | 1976-07-01 |
| DE2558399B2 DE2558399B2 (de) | 1977-08-04 |
| DE2558399C3 true DE2558399C3 (de) | 1978-03-30 |
Family
ID=27065265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2558399A Expired DE2558399C3 (de) | 1974-12-27 | 1975-12-23 | Verfahren zur Herstellung von 3,6-Dichlorpicolinsäure |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5188971A (cg-RX-API-DMAC10.html) |
| AR (1) | AR218217A1 (cg-RX-API-DMAC10.html) |
| BR (1) | BR7508648A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1050989A (cg-RX-API-DMAC10.html) |
| CS (1) | CS187331B2 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2558399C3 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2295952A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1469610A (cg-RX-API-DMAC10.html) |
| HU (1) | HU173174B (cg-RX-API-DMAC10.html) |
| IN (1) | IN140318B (cg-RX-API-DMAC10.html) |
| MY (1) | MY7800020A (cg-RX-API-DMAC10.html) |
| NL (1) | NL181358C (cg-RX-API-DMAC10.html) |
| PH (1) | PH11766A (cg-RX-API-DMAC10.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS588235U (ja) * | 1981-07-09 | 1983-01-19 | 三洋電機株式会社 | タイマ−回路 |
| DE3600287A1 (de) | 1986-01-08 | 1987-07-16 | Bayer Ag | 1-arylpyrazole |
| TWI579274B (zh) | 2012-04-20 | 2017-04-21 | 龍馬躍公司 | 製備１－芳基－５－烷基吡唑化合物的改良方法 |
| CN105503713A (zh) * | 2015-12-24 | 2016-04-20 | 浙江埃森化学有限公司 | 3,4,5,6-四氯吡啶甲酸加氢还原制备3,6-二氯吡啶酸的方法 |
-
1975
- 1975-11-10 IN IN2143/CAL/75A patent/IN140318B/en unknown
- 1975-12-22 HU HU75DO403A patent/HU173174B/hu unknown
- 1975-12-22 NL NLAANVRAGE7514931,A patent/NL181358C/xx not_active IP Right Cessation
- 1975-12-23 PH PH17918A patent/PH11766A/en unknown
- 1975-12-23 JP JP50153898A patent/JPS5188971A/ja active Granted
- 1975-12-23 CA CA242,410A patent/CA1050989A/en not_active Expired
- 1975-12-23 DE DE2558399A patent/DE2558399C3/de not_active Expired
- 1975-12-23 GB GB5274275A patent/GB1469610A/en not_active Expired
- 1975-12-23 AR AR261751A patent/AR218217A1/es active
- 1975-12-23 FR FR7539506A patent/FR2295952A1/fr active Granted
- 1975-12-23 CS CS758831A patent/CS187331B2/cs unknown
- 1975-12-26 BR BR7508648*A patent/BR7508648A/pt unknown
-
1978
- 1978-12-31 MY MY197820A patent/MY7800020A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1050989A (en) | 1979-03-20 |
| FR2295952A1 (fr) | 1976-07-23 |
| NL181358B (nl) | 1987-03-02 |
| NL181358C (nl) | 1987-08-03 |
| PH11766A (en) | 1978-06-27 |
| FR2295952B1 (cg-RX-API-DMAC10.html) | 1978-05-19 |
| GB1469610A (en) | 1977-04-06 |
| IN140318B (cg-RX-API-DMAC10.html) | 1976-10-16 |
| JPS5337350B2 (cg-RX-API-DMAC10.html) | 1978-10-07 |
| MY7800020A (en) | 1978-12-31 |
| JPS5188971A (en) | 1976-08-04 |
| CS187331B2 (en) | 1979-01-31 |
| AR218217A1 (es) | 1980-05-30 |
| DE2558399A1 (de) | 1976-07-01 |
| NL7514931A (nl) | 1976-06-29 |
| AU8779275A (en) | 1977-06-30 |
| BR7508648A (pt) | 1976-09-08 |
| DE2558399B2 (de) | 1977-08-04 |
| HU173174B (hu) | 1979-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |