SU624573A3 - Способ получени 4,4,-бипиридилов и / или 2,2,-бипиридилов или их солей - Google Patents
Способ получени 4,4,-бипиридилов и / или 2,2,-бипиридилов или их солейInfo
- Publication number
- SU624573A3 SU624573A3 SU721802654A SU1802654A SU624573A3 SU 624573 A3 SU624573 A3 SU 624573A3 SU 721802654 A SU721802654 A SU 721802654A SU 1802654 A SU1802654 A SU 1802654A SU 624573 A3 SU624573 A3 SU 624573A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- bipyridyls
- paragraphs
- salts
- weight
- halopyridine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 150000003839 salts Chemical class 0.000 title claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 26
- 229910052763 palladium Inorganic materials 0.000 claims description 14
- 150000005748 halopyridines Chemical class 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 239000012429 reaction media Substances 0.000 claims description 5
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000005749 2-halopyridines Chemical class 0.000 claims 1
- 150000005751 4-halopyridines Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 7
- PVMNPAUTCMBOMO-UHFFFAOYSA-N 4-chloropyridine Chemical compound ClC1=CC=NC=C1 PVMNPAUTCMBOMO-UHFFFAOYSA-N 0.000 description 6
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FEEUBWQZGMDPGX-UHFFFAOYSA-N 2,2-dimethyl-4-pyridin-4-yl-1H-pyridine Chemical group CC1(NC=CC(=C1)C1=CC=NC=C1)C FEEUBWQZGMDPGX-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical group C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 description 1
- GEFCQVXTSKQUPS-UHFFFAOYSA-N 4-chloro-2-methylpyridine;hydrochloride Chemical compound Cl.CC1=CC(Cl)=CC=N1 GEFCQVXTSKQUPS-UHFFFAOYSA-N 0.000 description 1
- DZNXMHJMXLSNIR-UHFFFAOYSA-N 4-chloro-3-methylpyridine Chemical compound CC1=CN=CC=C1Cl DZNXMHJMXLSNIR-UHFFFAOYSA-N 0.000 description 1
- XGAFCCUNHIMIRV-UHFFFAOYSA-N 4-chloropyridine;hydron;chloride Chemical compound Cl.ClC1=CC=NC=C1 XGAFCCUNHIMIRV-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- -1 halopyridine hydrochloride Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2958471 | 1971-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU624573A3 true SU624573A3 (ru) | 1978-09-15 |
Family
ID=10293854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU721802654A SU624573A3 (ru) | 1971-06-24 | 1972-06-24 | Способ получени 4,4,-бипиридилов и / или 2,2,-бипиридилов или их солей |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3804845A (OSRAM) |
| JP (1) | JPS5632310B1 (OSRAM) |
| BE (1) | BE785107Q (OSRAM) |
| BR (1) | BR7204137D0 (OSRAM) |
| CA (1) | CA980779A (OSRAM) |
| CH (1) | CH572038A5 (OSRAM) |
| DD (1) | DD101891A5 (OSRAM) |
| DE (1) | DE2230562A1 (OSRAM) |
| FR (1) | FR2143443B1 (OSRAM) |
| GB (1) | GB1340006A (OSRAM) |
| HU (1) | HU165933B (OSRAM) |
| IT (1) | IT956820B (OSRAM) |
| NL (1) | NL7208473A (OSRAM) |
| SU (1) | SU624573A3 (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5200427A (en) * | 1984-07-27 | 1993-04-06 | The Board Of Trustees Of The Univ. Of Illinois | Porphyric insecticides |
| ZA855561B (en) * | 1984-07-27 | 1986-03-26 | Univ Illinois | Photodynamic herbicides |
| US5300526A (en) * | 1984-07-27 | 1994-04-05 | The Board Of Trustees Of The University Of Illinois | Porphyric insecticides |
| WO1986000785A1 (en) * | 1984-07-27 | 1986-02-13 | University Of Illinois | Photodynamic herbicides |
| US5242892A (en) * | 1984-07-27 | 1993-09-07 | The Board Of Trustees Of The University Of Illinois | Chlorophyll biosynthesis modulators |
| JPH04137314A (ja) * | 1990-09-26 | 1992-05-12 | Sekisui Chem Co Ltd | 光ファイバケーブル |
| US5736274A (en) * | 1994-10-22 | 1998-04-07 | Daikin Industries, Ltd. | Conjugated N-fluoropyridinium salt-containing polymer and use of the same |
| US6500956B1 (en) | 1998-04-29 | 2002-12-31 | Axiva Gmbh | Method for the catalytic production of substituted bipyridyl derivatives |
| JP4744163B2 (ja) * | 2005-02-28 | 2011-08-10 | 広栄化学工業株式会社 | ビピリジン類の製造方法 |
-
1971
- 1971-06-24 GB GB2958471A patent/GB1340006A/en not_active Expired
-
1972
- 1972-06-19 BE BE785107A patent/BE785107Q/xx active
- 1972-06-19 US US00264237A patent/US3804845A/en not_active Expired - Lifetime
- 1972-06-21 HU HUIE510A patent/HU165933B/hu unknown
- 1972-06-21 NL NL7208473A patent/NL7208473A/xx not_active Application Discontinuation
- 1972-06-22 DE DE2230562A patent/DE2230562A1/de active Pending
- 1972-06-22 CA CA145,465A patent/CA980779A/en not_active Expired
- 1972-06-23 IT IT26156/72A patent/IT956820B/it active
- 1972-06-23 BR BR4137/72A patent/BR7204137D0/pt unknown
- 1972-06-23 FR FR7222906A patent/FR2143443B1/fr not_active Expired
- 1972-06-23 DD DD163945A patent/DD101891A5/xx unknown
- 1972-06-23 CH CH946772A patent/CH572038A5/xx not_active IP Right Cessation
- 1972-06-23 JP JP6249472A patent/JPS5632310B1/ja active Pending
- 1972-06-24 SU SU721802654A patent/SU624573A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| CH572038A5 (OSRAM) | 1976-01-30 |
| BE785107Q (fr) | 1972-12-19 |
| IT956820B (it) | 1973-10-10 |
| BR7204137D0 (pt) | 1973-06-14 |
| DE2230562A1 (de) | 1973-02-08 |
| FR2143443A1 (OSRAM) | 1973-02-02 |
| HU165933B (OSRAM) | 1974-12-28 |
| JPS5632310B1 (OSRAM) | 1981-07-27 |
| US3804845A (en) | 1974-04-16 |
| DD101891A5 (OSRAM) | 1973-11-20 |
| NL7208473A (OSRAM) | 1972-12-28 |
| AU4368572A (en) | 1974-01-03 |
| GB1340006A (en) | 1973-12-05 |
| CA980779A (en) | 1975-12-30 |
| FR2143443B1 (OSRAM) | 1977-12-23 |
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