PL96925B1 - Sposob wytwarzania 8-hydroksychinoliny - Google Patents
Sposob wytwarzania 8-hydroksychinoliny Download PDFInfo
- Publication number
- PL96925B1 PL96925B1 PL1975183966A PL18396675A PL96925B1 PL 96925 B1 PL96925 B1 PL 96925B1 PL 1975183966 A PL1975183966 A PL 1975183966A PL 18396675 A PL18396675 A PL 18396675A PL 96925 B1 PL96925 B1 PL 96925B1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- mol
- nitrophenol
- acrolein
- aminophenol
- Prior art date
Links
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 35
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 21
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 229960003540 oxyquinoline Drugs 0.000 claims description 16
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 12
- 239000011707 mineral Substances 0.000 claims description 12
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- TXECTBGVEUDNSL-UHFFFAOYSA-N 1-acetyloxyprop-2-enyl acetate Chemical compound CC(=O)OC(C=C)OC(C)=O TXECTBGVEUDNSL-UHFFFAOYSA-N 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- 235000010755 mineral Nutrition 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 241000746935 Nolina Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000004325 8-hydroxyquinolines Chemical class 0.000 description 1
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005614 Skraup synthesis reaction Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- -1 acrolein acetals Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000002308 calcification Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7434398A FR2288090A1 (fr) | 1974-10-14 | 1974-10-14 | Procede de preparation de la 8-hydroxyquinoleine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL96925B1 true PL96925B1 (pl) | 1978-01-31 |
Family
ID=9144036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1975183966A PL96925B1 (pl) | 1974-10-14 | 1975-10-13 | Sposob wytwarzania 8-hydroksychinoliny |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4044011A (en, 2012) |
| JP (1) | JPS5165771A (en, 2012) |
| BE (1) | BE834299A (en, 2012) |
| BG (1) | BG27082A3 (en, 2012) |
| DE (1) | DE2545704A1 (en, 2012) |
| DK (1) | DK139967B (en, 2012) |
| ES (1) | ES441748A1 (en, 2012) |
| FR (1) | FR2288090A1 (en, 2012) |
| GB (1) | GB1479383A (en, 2012) |
| HU (1) | HU171607B (en, 2012) |
| IE (1) | IE41810B1 (en, 2012) |
| IT (1) | IT1047268B (en, 2012) |
| LU (1) | LU73575A1 (en, 2012) |
| NL (1) | NL7512013A (en, 2012) |
| PL (1) | PL96925B1 (en, 2012) |
| RO (1) | RO65958A (en, 2012) |
| SU (1) | SU544371A3 (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105777630A (zh) * | 2016-04-05 | 2016-07-20 | 叶芳 | 一种8-羟基喹啉及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR977687A (fr) * | 1942-10-12 | 1951-04-04 | Méthode d'obtention des bases quinoléiques à partir de l'acroléine | |
| JPS4812745B1 (en, 2012) * | 1970-12-25 | 1973-04-23 |
-
1974
- 1974-10-14 FR FR7434398A patent/FR2288090A1/fr active Granted
-
1975
- 1975-10-02 IT IT69444/75A patent/IT1047268B/it active
- 1975-10-03 JP JP50119025A patent/JPS5165771A/ja active Pending
- 1975-10-08 BE BE160772A patent/BE834299A/xx unknown
- 1975-10-09 US US05/621,024 patent/US4044011A/en not_active Expired - Lifetime
- 1975-10-11 DE DE19752545704 patent/DE2545704A1/de active Pending
- 1975-10-11 RO RO7583581A patent/RO65958A/ro unknown
- 1975-10-13 SU SU2180254A patent/SU544371A3/ru active
- 1975-10-13 PL PL1975183966A patent/PL96925B1/pl unknown
- 1975-10-13 ES ES441748A patent/ES441748A1/es not_active Expired
- 1975-10-13 GB GB41864/75A patent/GB1479383A/en not_active Expired
- 1975-10-13 HU HU75KU00000496A patent/HU171607B/hu unknown
- 1975-10-13 IE IE2221/75A patent/IE41810B1/en unknown
- 1975-10-13 LU LU73575A patent/LU73575A1/xx unknown
- 1975-10-13 NL NL7512013A patent/NL7512013A/xx not_active Application Discontinuation
- 1975-10-13 DK DK459175AA patent/DK139967B/da unknown
- 1975-10-14 BG BG031220A patent/BG27082A3/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU544371A3 (ru) | 1977-01-25 |
| IE41810L (en) | 1976-04-14 |
| RO65958A (fr) | 1979-06-15 |
| GB1479383A (en) | 1977-07-13 |
| BE834299A (fr) | 1976-04-08 |
| IE41810B1 (en) | 1980-03-26 |
| DK459175A (en, 2012) | 1976-04-15 |
| JPS5165771A (en) | 1976-06-07 |
| HU171607B (hu) | 1978-02-28 |
| FR2288090A1 (fr) | 1976-05-14 |
| ES441748A1 (es) | 1977-03-16 |
| DE2545704A1 (de) | 1976-04-22 |
| IT1047268B (it) | 1980-09-10 |
| DK139967B (da) | 1979-05-28 |
| FR2288090B1 (en, 2012) | 1977-03-18 |
| NL7512013A (nl) | 1976-04-20 |
| LU73575A1 (en, 2012) | 1976-06-11 |
| DK139967C (en, 2012) | 1979-10-29 |
| US4044011A (en) | 1977-08-23 |
| BG27082A3 (bg) | 1979-08-15 |
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