JPS609712B2 - ３―ヒドロキシ―２―イミノ―１（２ｈ）―ピリジンスルホン酸―水塩の製造方法 - Google Patents
３―ヒドロキシ―２―イミノ―１（２ｈ）―ピリジンスルホン酸―水塩の製造方法Info
- Publication number
- JPS609712B2 JPS609712B2 JP52062040A JP6204077A JPS609712B2 JP S609712 B2 JPS609712 B2 JP S609712B2 JP 52062040 A JP52062040 A JP 52062040A JP 6204077 A JP6204077 A JP 6204077A JP S609712 B2 JPS609712 B2 JP S609712B2
- Authority
- JP
- Japan
- Prior art keywords
- furfural
- acid
- mol
- moles
- hydroxy
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- MEWPEKKXNPDJNC-UHFFFAOYSA-N 3-hydroxy-2-iminopyridine-1-sulfonic acid;hydrate Chemical compound O.OC1=CC=CN(S(O)(=O)=O)C1=N MEWPEKKXNPDJNC-UHFFFAOYSA-N 0.000 title description 6
- HYBBIBNJHNGZAN-UHFFFAOYSA-N Furaldehyde Natural products O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 71
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 19
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 12
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 claims description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 11
- 230000003647 oxidation Effects 0.000 claims description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- 239000011574 phosphorus Substances 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims description 8
- 235000019396 potassium bromate Nutrition 0.000 claims description 8
- XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 239000004153 Potassium bromate Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 229940094037 potassium bromate Drugs 0.000 claims description 7
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 7
- 229910001513 alkali metal bromide Inorganic materials 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 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 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims description 3
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 3
- 229940005657 pyrophosphoric acid Drugs 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 claims description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
- 229910001616 alkaline earth metal bromide Inorganic materials 0.000 claims 2
- 229910001617 alkaline earth metal chloride Inorganic materials 0.000 claims 2
- -1 imino-1(2H)-pyridine sulfonic acid hydrate Chemical compound 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 53
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 5
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 239000004071 soot Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BMTSZVZQNMNPCT-UHFFFAOYSA-N 2-aminopyridin-3-ol Chemical compound NC1=NC=CC=C1O BMTSZVZQNMNPCT-UHFFFAOYSA-N 0.000 description 1
- 241000545744 Hirudinea Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- OVLXOTUWFLHWQT-UHFFFAOYSA-N oxazolo[4,5-b]pyridin-2(3H)-one Chemical compound C1=CC=C2OC(=O)NC2=N1 OVLXOTUWFLHWQT-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- OCATYIAKPYKMPG-UHFFFAOYSA-M potassium bromate Chemical class [K+].[O-]Br(=O)=O OCATYIAKPYKMPG-UHFFFAOYSA-M 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater 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
- C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/690,497 US4052406A (en) | 1976-05-27 | 1976-05-27 | Process for the production of 3-hydroxy-2-imino-(2h)-pyridinesulphonic acid monohydrate |
| US690497 | 1976-05-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52144677A JPS52144677A (en) | 1977-12-02 |
| JPS609712B2 true JPS609712B2 (ja) | 1985-03-12 |
Family
ID=24772705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52062040A Expired JPS609712B2 (ja) | 1976-05-27 | 1977-05-27 | ３―ヒドロキシ―２―イミノ―１（２ｈ）―ピリジンスルホン酸―水塩の製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4052406A (Direct) |
| JP (1) | JPS609712B2 (Direct) |
| BE (1) | BE855066A (Direct) |
| CH (1) | CH628033A5 (Direct) |
| DE (1) | DE2723389A1 (Direct) |
| DK (1) | DK147259C (Direct) |
| FR (1) | FR2352802A1 (Direct) |
| GB (1) | GB1578886A (Direct) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6229407A (ja) * | 1985-07-26 | 1987-02-07 | アウデイ アクチエンゲゼルシヤフト | 緩衝脚における車輪接地点の横力の補整装置 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3706753A (en) * | 1965-04-29 | 1972-12-19 | Ciba Geigy Corp | Process for the preparation of 2-amino-3-pyridinol |
| CH449011A (de) * | 1965-04-29 | 1967-12-31 | Geigy Ag J R | Verfahren zur Herstellung von 2,3-Pyridindiol |
| US3808218A (en) * | 1970-06-26 | 1974-04-30 | Ciba Geigy Corp | 3h-oxazolo(4,5-b)pyridine-2-one,esters with 3-(-o-)or(-s-)-o,o'-diloweralkyl phosphates or thiophosphates |
-
1976
- 1976-05-27 US US05/690,497 patent/US4052406A/en not_active Expired - Lifetime
-
1977
- 1977-05-24 DE DE19772723389 patent/DE2723389A1/de not_active Withdrawn
- 1977-05-25 CH CH644177A patent/CH628033A5/de not_active IP Right Cessation
- 1977-05-25 GB GB22123/77A patent/GB1578886A/en not_active Expired
- 1977-05-26 DK DK232577A patent/DK147259C/da not_active IP Right Cessation
- 1977-05-26 FR FR7716128A patent/FR2352802A1/fr active Granted
- 1977-05-26 BE BE177928A patent/BE855066A/xx not_active IP Right Cessation
- 1977-05-27 JP JP52062040A patent/JPS609712B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6229407A (ja) * | 1985-07-26 | 1987-02-07 | アウデイ アクチエンゲゼルシヤフト | 緩衝脚における車輪接地点の横力の補整装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| US4052406A (en) | 1977-10-04 |
| GB1578886A (en) | 1980-11-12 |
| DK147259B (da) | 1984-05-28 |
| DK147259C (da) | 1984-11-26 |
| FR2352802A1 (fr) | 1977-12-23 |
| FR2352802B1 (Direct) | 1980-06-06 |
| DE2723389A1 (de) | 1977-12-08 |
| JPS52144677A (en) | 1977-12-02 |
| BE855066A (fr) | 1977-11-28 |
| DK232577A (da) | 1977-11-28 |
| CH628033A5 (de) | 1982-02-15 |
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