JP2506387B2 - ３，５−ジクロロ−２，４，６−トリフルオロピリジンの改良製造法 - Google Patents
３，５−ジクロロ−２，４，６−トリフルオロピリジンの改良製造法Info
- Publication number
- JP2506387B2 JP2506387B2 JP62267612A JP26761287A JP2506387B2 JP 2506387 B2 JP2506387 B2 JP 2506387B2 JP 62267612 A JP62267612 A JP 62267612A JP 26761287 A JP26761287 A JP 26761287A JP 2506387 B2 JP2506387 B2 JP 2506387B2
- Authority
- JP
- Japan
- Prior art keywords
- dichloro
- reaction
- trifluoropyridine
- potassium fluoride
- distillation
- 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
- 238000000034 method Methods 0.000 title claims description 25
- PKSORSNCSXBXOT-UHFFFAOYSA-N 3,5-dichloro-2,4,6-trifluoropyridine Chemical compound FC1=NC(F)=C(Cl)C(F)=C1Cl PKSORSNCSXBXOT-UHFFFAOYSA-N 0.000 title claims description 20
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 61
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 235000003270 potassium fluoride Nutrition 0.000 claims description 30
- 239000011698 potassium fluoride Substances 0.000 claims description 30
- DNDPLEAVNVOOQZ-UHFFFAOYSA-N 2,3,4,5,6-pentachloropyridine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=C1Cl DNDPLEAVNVOOQZ-UHFFFAOYSA-N 0.000 claims description 29
- 238000004821 distillation Methods 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 10
- 239000002002 slurry Substances 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000011269 tar Substances 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 5
- DSQYRFHQDSVYNI-UHFFFAOYSA-N 2,3,4-trichloro-5,6-difluoropyridine Chemical compound FC1=NC(Cl)=C(Cl)C(Cl)=C1F DSQYRFHQDSVYNI-UHFFFAOYSA-N 0.000 description 4
- SLEJZQYOXXCDQU-UHFFFAOYSA-N 2,3,4-trifluoropyridine Chemical compound FC1=CC=NC(F)=C1F SLEJZQYOXXCDQU-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910000792 Monel Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- IKZSQJOVXGDGAH-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-fluoropyridine Chemical compound FC1=NC(Cl)=C(Cl)C(Cl)=C1Cl IKZSQJOVXGDGAH-UHFFFAOYSA-N 0.000 description 1
- KZLNLWPRWHPFEE-UHFFFAOYSA-N 2,3,5,6-tetrachloro-4-fluoropyridine Chemical compound FC1=C(Cl)C(Cl)=NC(Cl)=C1Cl KZLNLWPRWHPFEE-UHFFFAOYSA-N 0.000 description 1
- OGVLEPMNNPZAPS-UHFFFAOYSA-N 2,3-difluoropyridine Chemical compound FC1=CC=CN=C1F OGVLEPMNNPZAPS-UHFFFAOYSA-N 0.000 description 1
- SVAZIMBLBHOVIR-UHFFFAOYSA-N 2-chloro-3-fluoropyridine Chemical compound FC1=CC=CN=C1Cl SVAZIMBLBHOVIR-UHFFFAOYSA-N 0.000 description 1
- NLVYFXLILFDECX-UHFFFAOYSA-N 2-pyridin-2-yloxyacetic acid Chemical compound OC(=O)COC1=CC=CC=N1 NLVYFXLILFDECX-UHFFFAOYSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000003928 amperometric titration Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- MJAWMRVEIWPJRW-UHFFFAOYSA-N haloxydine Chemical group FC=1NC(F)=C(Cl)C(=O)C=1Cl MJAWMRVEIWPJRW-UHFFFAOYSA-N 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004753 textile Substances 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
- C07D213/61—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US921563 | 1986-10-22 | ||
| US06/921,563 US4746744A (en) | 1986-10-22 | 1986-10-22 | Method of preparation of 3,5-dichloro-2,4,6-trifluoropyridine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63115862A JPS63115862A (ja) | 1988-05-20 |
| JP2506387B2 true JP2506387B2 (ja) | 1996-06-12 |
Family
ID=25445627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62267612A Expired - Fee Related JP2506387B2 (ja) | 1986-10-22 | 1987-10-22 | ３，５−ジクロロ−２，４，６−トリフルオロピリジンの改良製造法 |
Country Status (9)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6807573B2 (en) | 1997-09-16 | 2004-10-19 | Kabushiki Kaisha Toshiba | Scheme for managing nodes connected to a home network according to their physical locations |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4999432A (en) * | 1989-08-28 | 1991-03-12 | Dowelanco | Fluorination with hydrogen fluoride |
| US4994252A (en) * | 1990-02-09 | 1991-02-19 | Dowelanco | Removal of potassium chloride from solvents |
| US4976946A (en) * | 1990-02-09 | 1990-12-11 | The Dow Chemical Company | Separation of potassium salts |
| US5650517A (en) * | 1994-11-01 | 1997-07-22 | Ciba-Geigy Corporation | Process for the preparation of 2,3-difluoro-5-halopyridines |
| RU2209198C2 (ru) * | 2001-09-10 | 2003-07-27 | Общество с ограниченной ответственностью Научно-внедренческая фирма "Окта" | Способ получения фторсодержащих гетероциклических соединений |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1039987A (en) * | 1964-03-17 | 1966-08-24 | Pennwalt Corp | Fluoropyridines |
| GB1198476A (en) * | 1967-05-22 | 1970-07-15 | Ici Ltd | Preparation of Halopyridines |
| GB1256082A (en) * | 1968-09-30 | 1971-12-08 | Ici Ltd | Manufacture of chlorofluoropyridines |
| GB1306517A (en) * | 1970-06-08 | 1973-02-14 | Ici Ltd | Manufacture of halogenated pyridine derivatives |
| GB1340421A (en) * | 1971-01-14 | 1973-12-12 | Ici Ltd | Manufacture of chlorofluoropyridines |
| CA1292746C (en) * | 1983-12-23 | 1991-12-03 | Charles A. Wilson | Preparation of difluoropyridine compounds |
| GB8504268D0 (en) * | 1985-02-19 | 1985-03-20 | Shell Int Research | Preparation of fluorinated pyridines |
-
1986
- 1986-10-22 US US06/921,563 patent/US4746744A/en not_active Expired - Lifetime
-
1987
- 1987-10-09 DE DE87308961T patent/DE3789007T2/de not_active Expired - Fee Related
- 1987-10-09 EP EP87308961A patent/EP0270221B1/en not_active Expired - Lifetime
- 1987-10-09 ES ES87308961T patent/ES2061510T3/es not_active Expired - Lifetime
- 1987-10-13 IL IL84153A patent/IL84153A/xx not_active IP Right Cessation
- 1987-10-21 HU HU874730A patent/HU202203B/hu not_active IP Right Cessation
- 1987-10-21 CA CA000549835A patent/CA1301763C/en not_active Expired - Fee Related
- 1987-10-22 JP JP62267612A patent/JP2506387B2/ja not_active Expired - Fee Related
-
1988
- 1988-03-14 CH CH945/88A patent/CH677666A5/it not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6807573B2 (en) | 1997-09-16 | 2004-10-19 | Kabushiki Kaisha Toshiba | Scheme for managing nodes connected to a home network according to their physical locations |
| US7020694B2 (en) | 1997-09-16 | 2006-03-28 | Kabushiki Kaisha Toshiba | Scheme for managing nodes connected to a home network according to their physical locations |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63115862A (ja) | 1988-05-20 |
| IL84153A (en) | 1992-02-16 |
| US4746744A (en) | 1988-05-24 |
| EP0270221A1 (en) | 1988-06-08 |
| EP0270221B1 (en) | 1994-02-02 |
| CH677666A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-06-14 |
| DE3789007D1 (de) | 1994-03-17 |
| HU202203B (en) | 1991-02-28 |
| ES2061510T3 (es) | 1994-12-16 |
| DE3789007T2 (de) | 1994-05-11 |
| HUT48214A (en) | 1989-05-29 |
| CA1301763C (en) | 1992-05-26 |
| IL84153A0 (en) | 1988-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |