DE2117360C2 - Verfahren zur Herstellung von Gemischen aus C-substituierten Pyridinen und den entsprechenden hydrierten C-substituierten Pyridinen - Google Patents
Verfahren zur Herstellung von Gemischen aus C-substituierten Pyridinen und den entsprechenden hydrierten C-substituierten PyridinenInfo
- Publication number
- DE2117360C2 DE2117360C2 DE2117360A DE2117360A DE2117360C2 DE 2117360 C2 DE2117360 C2 DE 2117360C2 DE 2117360 A DE2117360 A DE 2117360A DE 2117360 A DE2117360 A DE 2117360A DE 2117360 C2 DE2117360 C2 DE 2117360C2
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- hydrogen
- oxohexanenitrile
- per
- substituted pyridines
- 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
- 239000000203 mixture Substances 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 10
- 150000003222 pyridines Chemical class 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003054 catalyst Substances 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- AEVMBQIIZGKQRB-UHFFFAOYSA-N 5-oxohexanenitrile Chemical group CC(=O)CCCC#N AEVMBQIIZGKQRB-UHFFFAOYSA-N 0.000 claims description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- NWVJJSXURDQKFU-UHFFFAOYSA-N 4-methyl-5-oxohexanenitrile Chemical compound CC(=O)C(C)CCC#N NWVJJSXURDQKFU-UHFFFAOYSA-N 0.000 claims description 3
- 239000000395 magnesium oxide Substances 0.000 claims description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- YJNQITHVCLOUMM-UHFFFAOYSA-N 5-oxoheptanenitrile Chemical compound CCC(=O)CCCC#N YJNQITHVCLOUMM-UHFFFAOYSA-N 0.000 claims 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 description 14
- 239000007789 gas Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 5
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- DRLFSUDDXLQHJT-UHFFFAOYSA-N 2,3-dimethylpiperidine Chemical compound CC1CCCNC1C DRLFSUDDXLQHJT-UHFFFAOYSA-N 0.000 description 2
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 description 2
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- POTIYWUALSJREP-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCCC2CCCCC21 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 description 1
- UKPBWLDHWHLVFV-UHFFFAOYSA-N 1-methyl-3,4-dihydro-2h-pyridine Chemical compound CN1CCCC=C1 UKPBWLDHWHLVFV-UHFFFAOYSA-N 0.000 description 1
- FTKZKUSQFCXEEL-UHFFFAOYSA-N 2-ethyl-3-methylpyridine Chemical compound CCC1=NC=CC=C1C FTKZKUSQFCXEEL-UHFFFAOYSA-N 0.000 description 1
- QBBKKFZGCDJDQK-UHFFFAOYSA-N 2-ethylpiperidine Chemical compound CCC1CCCCN1 QBBKKFZGCDJDQK-UHFFFAOYSA-N 0.000 description 1
- BXYHISUMXGPDKC-UHFFFAOYSA-N 4-methyl-5-oxoheptanenitrile Chemical compound CCC(=O)C(C)CCC#N BXYHISUMXGPDKC-UHFFFAOYSA-N 0.000 description 1
- YQDGQEKUTLYWJU-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline Chemical compound C1=CC=C2CCCCC2=N1 YQDGQEKUTLYWJU-UHFFFAOYSA-N 0.000 description 1
- -1 5-oxohexane nitride Chemical class 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 230000004580 weight loss Effects 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
- C07D213/08—Preparation by ring-closure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/12—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with only hydrogen atoms attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
- Quinoline Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7004993.A NL164029C (nl) | 1970-04-08 | 1970-04-08 | Bereiding van c-gesubstitueerde pyridinen eventueel ge- mengd met de overeenkomstige gehydrogeneerde c-ge- subtitueerde pyridinen. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2117360A1 DE2117360A1 (de) | 1971-10-28 |
| DE2117360C2 true DE2117360C2 (de) | 1986-12-18 |
Family
ID=19809794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2117360A Expired DE2117360C2 (de) | 1970-04-08 | 1971-04-08 | Verfahren zur Herstellung von Gemischen aus C-substituierten Pyridinen und den entsprechenden hydrierten C-substituierten Pyridinen |
Country Status (13)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4154933A (en) * | 1973-12-15 | 1979-05-15 | Stamicarbon, B.V. | Process for the preparation of quinolines |
| NL176260C (nl) * | 1973-12-15 | 1985-03-18 | Stamicarbon | Werkwijze voor de bereiding van mengsels die al of niet c-gesubstitueerd chinoline bevatten. |
| NL7809552A (nl) * | 1978-09-20 | 1980-03-24 | Stamicarbon | Werkwijze voor de bereiding van c-gesubstitueerde pyri- dinen en/of gehydrogeneerde c-gesubstitueerde pyridi- nen. |
| US4294968A (en) * | 1979-06-29 | 1981-10-13 | The Dow Chemical Company | Method for preparing α-picoline from 5-oxohexanenitrile |
| NL9000034A (nl) * | 1990-01-06 | 1991-08-01 | Stamicarbon | Werkwijze voor de bereiding van 5-oxohexaannitrillen alsmede de stof 2,4-dimethyl-5-oxohexaannitril. |
| US5254712A (en) * | 1990-01-06 | 1993-10-19 | Stamicarbon B.V. | Process for the preparation of 5-oxohexane nitriles and the compound 2,4-dimethyl-5-oxohexane nitrile |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE904532C (de) * | 1940-11-02 | 1954-02-18 | Bayer Ag | Verfahren zur Herstellung von Piperidinverbindungen |
| US3007931A (en) * | 1959-03-09 | 1961-11-07 | Phillips Petroleum Co | Production of unsaturated heterocyclic nitrogen bases |
-
1970
- 1970-04-08 NL NL7004993.A patent/NL164029C/xx not_active IP Right Cessation
-
1971
- 1971-04-06 ES ES389955A patent/ES389955A1/es not_active Expired
- 1971-04-07 ZA ZA712221A patent/ZA712221B/xx unknown
- 1971-04-07 BE BE765409A patent/BE765409A/xx not_active IP Right Cessation
- 1971-04-07 BR BR2091/71A patent/BR7102091D0/pt unknown
- 1971-04-07 CH CH508671A patent/CH551971A/xx not_active IP Right Cessation
- 1971-04-07 SE SE7104613A patent/SE389865B/xx unknown
- 1971-04-08 AT AT300171A patent/AT306018B/de not_active IP Right Cessation
- 1971-04-08 FR FR7112478A patent/FR2089392A5/fr not_active Expired
- 1971-04-08 DE DE2117360A patent/DE2117360C2/de not_active Expired
- 1971-04-08 CA CA109,973A patent/CA981268A/en not_active Expired
- 1971-04-08 JP JP46022041A patent/JPS5212197B1/ja active Pending
- 1971-04-19 GB GB2613171*A patent/GB1304155A/en not_active Expired
-
1975
- 1975-12-09 JP JP50146791A patent/JPS51105077A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS532872B2 (enrdf_load_stackoverflow) | 1978-02-01 |
| BR7102091D0 (pt) | 1973-04-17 |
| GB1304155A (enrdf_load_stackoverflow) | 1973-01-24 |
| SE389865B (sv) | 1976-11-22 |
| AT306018B (de) | 1973-03-26 |
| NL164029C (nl) | 1980-11-17 |
| BE765409A (fr) | 1971-10-07 |
| ES389955A1 (es) | 1974-03-01 |
| FR2089392A5 (enrdf_load_stackoverflow) | 1972-01-07 |
| CH551971A (de) | 1974-07-31 |
| JPS51105077A (en) | 1976-09-17 |
| CA981268A (en) | 1976-01-06 |
| NL164029B (nl) | 1980-06-16 |
| ZA712221B (en) | 1971-12-29 |
| DE2117360A1 (de) | 1971-10-28 |
| JPS5212197B1 (enrdf_load_stackoverflow) | 1977-04-05 |
| NL7004993A (enrdf_load_stackoverflow) | 1971-10-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3130805A1 (de) | Neue ruthenium/kohle-hydrierkatalysatoren, deren herstellung und verwendung zur selektiven hydrierung von ungesaettigten carbonylverbindungen | |
| DE2117360C2 (de) | Verfahren zur Herstellung von Gemischen aus C-substituierten Pyridinen und den entsprechenden hydrierten C-substituierten Pyridinen | |
| DE2902986C2 (de) | Verfahren zur Herstellung von Maleinsäureanhydrid | |
| EP0048378B1 (de) | Verfahren zur Herstellung ungesättigter Kohlenwasserstoffe | |
| DE1925965C3 (de) | Verfahren zur Herstellung von Acrylsäure durch Oxydation von Propylen | |
| DE69006475T2 (de) | Verfahren zur Herstellung von Isocyanatverbindung. | |
| DE2235103C3 (de) | Verfahren zur Herstellung von Essigsäure | |
| EP0057890B1 (de) | Verfahren zur Herstellung von Pyridinen oder Pyrrolen aus alpha,omega-Dinitrilen | |
| DE3780616T2 (de) | Verfahren zur herstellung eines 2-alkyl- oder 2-phenyl-1,4,5,6-tetrahydropyrimidins und verfahren zur herstellung von 2-alkyl- oder 2-phenyl-pyrimidinen. | |
| DE68920543T2 (de) | Herstellungsverfahren von Homoallylalkoholen. | |
| EP0089417A1 (de) | Verfahren zur Herstellung von Phthalid | |
| DE3018575C2 (de) | Verfahren zur Herstellung eines Alkalimetallsalzes einer 3-(17β-Hydroxyandrosten-3-on-acetal-17α-yl)-propiolsäure | |
| DE2308365C2 (de) | Verfahren zur Herstellung von 3,4-Dihydrocumarin | |
| DE2558399C3 (de) | Verfahren zur Herstellung von 3,6-Dichlorpicolinsäure | |
| DE2459095C2 (de) | Verfahren zur Herstellung von Chinolinen | |
| EP2801563A1 (de) | Decarboxylierung von 6-Methylsalicylsäure | |
| EP1232145B1 (de) | Verfahren zur herstellung von hydroxymethylpyridinen | |
| EP0211205A2 (de) | Verfahren zur Herstellung von 2-Methyl-2-alkenalen | |
| DE2061491A1 (de) | Verfahren zur katalytischen Isomerisierung von olefinisch ungesättigten Verbindungen | |
| DE2736269C2 (de) | Verfahren zur Herstellung von Pyridin | |
| DE2703077A1 (de) | Verfahren zur herstellung von cyclohexandion-(1,4)-tetramethyl- diketal | |
| DE2202249A1 (de) | Isolierung von alpha-Cedren aus Zedernholzoelkohlenwasserstoffen | |
| DE2539014C3 (de) | Verfahren zur Herstellung von Humulonen und dabei gebildete Zwischenprodukte | |
| DE950908C (de) | Verfahren zur Herstellung von Butyraldehyd | |
| DE1095275B (de) | Verfahren zur Herstellung von Cyclohexanon aus Cyclohexylamin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8128 | New person/name/address of the agent |
Representative=s name: ASSMANN, E., DIPL.-CHEM. DR.RER.NAT. ZUMSTEIN, F., |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |