IL37468A - Manufacture of bipyridyls - Google Patents
Manufacture of bipyridylsInfo
- Publication number
- IL37468A IL37468A IL37468A IL3746871A IL37468A IL 37468 A IL37468 A IL 37468A IL 37468 A IL37468 A IL 37468A IL 3746871 A IL3746871 A IL 3746871A IL 37468 A IL37468 A IL 37468A
- Authority
- IL
- Israel
- Prior art keywords
- pyridine
- process according
- bipyridyl
- bipyridyls
- temperature
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 77
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 claims description 2
- PVMNPAUTCMBOMO-UHFFFAOYSA-N 4-chloropyridine Chemical compound ClC1=CC=NC=C1 PVMNPAUTCMBOMO-UHFFFAOYSA-N 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims 1
- RMHQDKYZXJVCME-UHFFFAOYSA-N 2-pyridin-4-ylpyridine Chemical group N1=CC=CC=C1C1=CC=NC=C1 RMHQDKYZXJVCME-UHFFFAOYSA-N 0.000 claims 1
- BSDGZUDFPKIYQG-UHFFFAOYSA-N 4-bromopyridine Chemical compound BrC1=CC=NC=C1 BSDGZUDFPKIYQG-UHFFFAOYSA-N 0.000 claims 1
- RTLUPHDWSUGAOS-UHFFFAOYSA-N 4-iodopyridine Chemical compound IC1=CC=NC=C1 RTLUPHDWSUGAOS-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 17
- 229910052736 halogen Inorganic materials 0.000 description 13
- 150000002367 halogens Chemical class 0.000 description 13
- -1 4-substituted pyridine Chemical class 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical group C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 150000005751 4-halopyridines Chemical class 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001030 gas--liquid chromatography Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- OHWLDHSSZYNNLN-UHFFFAOYSA-M 2-pyridin-1-ium-1-ylpyridine;chloride Chemical compound [Cl-].C1=CC=CC=[N+]1C1=CC=CC=N1 OHWLDHSSZYNNLN-UHFFFAOYSA-M 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical class C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- ZFTKWAVDJBKFCS-UHFFFAOYSA-N iodine;pyridine Chemical compound [I].C1=CC=NC=C1 ZFTKWAVDJBKFCS-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- YHBDIEWMOMLKOO-UHFFFAOYSA-I pentachloroniobium Chemical compound Cl[Nb](Cl)(Cl)(Cl)Cl YHBDIEWMOMLKOO-UHFFFAOYSA-I 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- OEIMLTQPLAGXMX-UHFFFAOYSA-I tantalum(v) chloride Chemical compound Cl[Ta](Cl)(Cl)(Cl)Cl OEIMLTQPLAGXMX-UHFFFAOYSA-I 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3948170A GB1338399A (en) | 1970-08-17 | 1970-08-17 | Manufacture of bipyridyls |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL37468A0 IL37468A0 (en) | 1971-12-29 |
| IL37468A true IL37468A (en) | 1974-09-10 |
Family
ID=10409786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL37468A IL37468A (en) | 1970-08-17 | 1971-08-06 | Manufacture of bipyridyls |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3787427A (ro) |
| JP (1) | JPS5637226B1 (ro) |
| AT (1) | AT311346B (ro) |
| AU (1) | AU450859B2 (ro) |
| BE (1) | BE771430A (ro) |
| BR (1) | BR7105298D0 (ro) |
| CA (1) | CA962683A (ro) |
| CH (2) | CH583727A5 (ro) |
| CS (3) | CS171238B2 (ro) |
| DE (1) | DE2140529A1 (ro) |
| DK (1) | DK140548B (ro) |
| ES (1) | ES394301A1 (ro) |
| FR (1) | FR2102296B1 (ro) |
| GB (1) | GB1338399A (ro) |
| HU (1) | HU163559B (ro) |
| IE (1) | IE35486B1 (ro) |
| IL (1) | IL37468A (ro) |
| NL (1) | NL7111252A (ro) |
| PL (1) | PL87152B1 (ro) |
| RO (1) | RO56865A (ro) |
| SE (1) | SE368008B (ro) |
| YU (1) | YU35761B (ro) |
| ZA (1) | ZA715125B (ro) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1399099A (en) * | 1971-11-15 | 1975-06-25 | Ici Ltd | Manufacture of bipyridyls |
| GB1445367A (en) * | 1973-10-25 | 1976-08-11 | Birkbeck College | Electrochemical production of substituted pyridines |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3040052A (en) * | 1962-06-19 | Preparation of z | ||
| US2962502A (en) * | 1958-01-24 | 1960-11-29 | Ici Ltd | Preparation of 2, 2'-bipyridyl |
| FR1236734A (fr) * | 1958-09-18 | 1960-07-22 | Ici Ltd | Procédé de production de polypyridyles |
-
1970
- 1970-08-17 GB GB3948170A patent/GB1338399A/en not_active Expired
-
1971
- 1971-08-02 ZA ZA715125A patent/ZA715125B/xx unknown
- 1971-08-03 CA CA119,693A patent/CA962683A/en not_active Expired
- 1971-08-03 IE IE978/71A patent/IE35486B1/xx unknown
- 1971-08-05 PL PL1971149861A patent/PL87152B1/pl unknown
- 1971-08-06 IL IL37468A patent/IL37468A/en unknown
- 1971-08-11 HU HUIE463A patent/HU163559B/hu unknown
- 1971-08-12 DE DE19712140529 patent/DE2140529A1/de not_active Ceased
- 1971-08-12 US US00171349A patent/US3787427A/en not_active Expired - Lifetime
- 1971-08-16 RO RO67975A patent/RO56865A/ro unknown
- 1971-08-16 NL NL7111252A patent/NL7111252A/xx not_active Application Discontinuation
- 1971-08-16 YU YU2103/71A patent/YU35761B/xx unknown
- 1971-08-16 AU AU32383/71A patent/AU450859B2/en not_active Expired
- 1971-08-16 FR FR7129822A patent/FR2102296B1/fr not_active Expired
- 1971-08-17 BR BR5298/71A patent/BR7105298D0/pt unknown
- 1971-08-17 JP JP6207571A patent/JPS5637226B1/ja active Pending
- 1971-08-17 CH CH1202671A patent/CH583727A5/xx not_active IP Right Cessation
- 1971-08-17 DK DK402671AA patent/DK140548B/da unknown
- 1971-08-17 BE BE771430A patent/BE771430A/xx unknown
- 1971-08-17 CS CS3147*[A patent/CS171238B2/cs unknown
- 1971-08-17 CS CS3148*[A patent/CS171239B2/cs unknown
- 1971-08-17 ES ES394301A patent/ES394301A1/es not_active Expired
- 1971-08-17 SE SE10464/71A patent/SE368008B/xx unknown
- 1971-08-17 CS CS5938A patent/CS171237B2/cs unknown
- 1971-08-17 AT AT717571A patent/AT311346B/de not_active IP Right Cessation
-
1976
- 1976-09-22 CH CH1202671A patent/CH592063A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2102296A1 (ro) | 1972-04-07 |
| AT311346B (de) | 1973-11-12 |
| DK140548C (ro) | 1980-02-25 |
| YU210371A (en) | 1980-12-31 |
| DK140548B (da) | 1979-10-01 |
| CS171239B2 (ro) | 1976-10-29 |
| YU35761B (en) | 1981-06-30 |
| ES394301A1 (es) | 1973-12-16 |
| IE35486B1 (en) | 1976-03-03 |
| DE2140529A1 (de) | 1972-03-23 |
| RO56865A (ro) | 1974-09-01 |
| CH583727A5 (ro) | 1977-01-14 |
| HU163559B (ro) | 1973-09-27 |
| CS171238B2 (ro) | 1976-10-29 |
| IL37468A0 (en) | 1971-12-29 |
| ZA715125B (en) | 1972-04-26 |
| CA962683A (en) | 1975-02-11 |
| BE771430A (fr) | 1972-02-17 |
| AU3238371A (en) | 1973-02-22 |
| CS171237B2 (ro) | 1976-10-29 |
| BR7105298D0 (pt) | 1973-02-15 |
| AU450859B2 (en) | 1974-07-25 |
| US3787427A (en) | 1974-01-22 |
| JPS5637226B1 (ro) | 1981-08-29 |
| PL87152B1 (ro) | 1976-06-30 |
| GB1338399A (en) | 1973-11-21 |
| SE368008B (ro) | 1974-06-17 |
| FR2102296B1 (ro) | 1975-07-11 |
| IE35486L (en) | 1972-02-17 |
| NL7111252A (ro) | 1972-02-21 |
| CH592063A5 (ro) | 1977-10-14 |
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