DE2703049C2 - Verfahren zur Herstellung von Pyridin und 3-Methylpyridin - Google Patents
Verfahren zur Herstellung von Pyridin und 3-MethylpyridinInfo
- Publication number
- DE2703049C2 DE2703049C2 DE2703049A DE2703049A DE2703049C2 DE 2703049 C2 DE2703049 C2 DE 2703049C2 DE 2703049 A DE2703049 A DE 2703049A DE 2703049 A DE2703049 A DE 2703049A DE 2703049 C2 DE2703049 C2 DE 2703049C2
- Authority
- DE
- Germany
- Prior art keywords
- methylpyridine
- acrolein
- pyridine
- acetaldehyde
- ammonia
- 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
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 title claims description 44
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 44
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 60
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 42
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 34
- 229910021529 ammonia Inorganic materials 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 17
- 239000011148 porous material Substances 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- -1 aluminum silicates Chemical class 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- LDDQLRUQCUTJBB-UHFFFAOYSA-O azanium;hydrofluoride Chemical compound [NH4+].F LDDQLRUQCUTJBB-UHFFFAOYSA-O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000005496 tempering Methods 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
- C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
- C07D213/12—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from unsaturated compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2703049A DE2703049C2 (de) | 1977-01-26 | 1977-01-26 | Verfahren zur Herstellung von Pyridin und 3-Methylpyridin |
| ES464217A ES464217A1 (es) | 1977-01-26 | 1977-11-17 | Procedimiento para la preparacion de piridina y 3-metilpiri-dina. |
| FR7736595A FR2378764A1 (fr) | 1977-01-26 | 1977-12-05 | Procede de preparation de pyridine et de 3-methylpyridine |
| GB328/78A GB1557526A (en) | 1977-01-26 | 1978-01-05 | Process for the production of pyridine and 3 methyl pyridine |
| NL7800217A NL7800217A (nl) | 1977-01-26 | 1978-01-06 | Werkwijze voor het bereiden van pyridine en 3-methylpyridine. |
| IL53819A IL53819A (en) | 1977-01-26 | 1978-01-16 | Process for the production of pyridine and 3-methylpyridine |
| IN76/CAL/78A IN147407B (US08063081-20111122-C00242.png) | 1977-01-26 | 1978-01-19 | |
| SU782568900A SU670218A3 (ru) | 1977-01-26 | 1978-01-20 | Способ получени пиридина и 3-метилпиридина |
| BR7800414A BR7800414A (pt) | 1977-01-26 | 1978-01-24 | Processo para a producao de piridina e 3-metilpiridina |
| US05/871,976 US4147874A (en) | 1977-01-26 | 1978-01-24 | Process for the production of pyridine and 3-methyl pyridine |
| IT47765/78A IT1155787B (it) | 1977-01-26 | 1978-01-24 | Procedimento per la produzione di piridina e 3-metil-piridina |
| SE7800931A SE425734B (sv) | 1977-01-26 | 1978-01-25 | Forfarande for framstellning av pyridin och 3-metylpyridin |
| BE6046327A BE863319A (fr) | 1977-01-26 | 1978-01-25 | Procede de fabrication de pyridine et de 3-methypyridine et produits obtenus |
| CA295,667A CA1063122A (en) | 1977-01-26 | 1978-01-25 | Process for the production of pyridine and 3-methyl pyridine |
| CH81878A CH633269A5 (de) | 1977-01-26 | 1978-01-25 | Verfahren zur herstellung von pyridin und 3-methylpyridin. |
| MX786791U MX5066E (es) | 1977-01-26 | 1978-01-25 | Procedimiento mejorado para la elaboracion de piridina y 3-metilpiridina |
| JP781378A JPS5392782A (en) | 1977-01-26 | 1978-01-26 | Method of producing pyridine and 33methylpyridine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2703049A DE2703049C2 (de) | 1977-01-26 | 1977-01-26 | Verfahren zur Herstellung von Pyridin und 3-Methylpyridin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2703049A1 DE2703049A1 (de) | 1978-07-27 |
| DE2703049C2 true DE2703049C2 (de) | 1987-04-16 |
Family
ID=5999532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2703049A Expired DE2703049C2 (de) | 1977-01-26 | 1977-01-26 | Verfahren zur Herstellung von Pyridin und 3-Methylpyridin |
Country Status (17)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2639701A1 (de) * | 1976-09-03 | 1978-03-09 | Degussa | Verfahren zur herstellung substituierter pyridine |
| US4220783A (en) * | 1979-05-09 | 1980-09-02 | Mobil Oil Corporation | Synthesis of pyridine and alkylpyridines |
| US4675410A (en) * | 1983-07-11 | 1987-06-23 | Nepera Inc. | Process for the production of pyridine or alkyl substituted pyridines |
| DE3476382D1 (en) * | 1983-07-11 | 1989-03-02 | Nepera Inc | Improved process for preparing pyridine-type bases in a fluid bed using a crystalline aluminosilicate zeolite catalyst |
| US4861894A (en) * | 1987-06-11 | 1989-08-29 | Mobil Oil Corp. | Pyridine and alkylpyridine synthesis using a crystalline silicate catalyst having the ZSM-5 structure |
| FR2952057B1 (fr) * | 2009-11-04 | 2011-11-18 | Arkema France | Procede de synthese de pyridine et picolines bioressourcees |
| RU2599573C2 (ru) * | 2015-02-25 | 2016-10-10 | Федеральное Государственное Бюджетное Учреждение Науки Институт Нефтехимии И Катализа Ран | Способ получения пиридина и метилпиридинов |
| WO2018074257A1 (ja) * | 2016-10-18 | 2018-04-26 | 東レ・ダウコーニング株式会社 | ポリエーテル変性シリコーン組成物、それを含む界面活性剤、整泡剤、ポリウレタン発泡体形成組成物、化粧料およびその製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB963887A (en) * | 1960-10-08 | 1964-07-15 | Distillers Co Yeast Ltd | Production of pyridine and ª‰-picoline |
| GB1005984A (en) * | 1963-05-16 | 1965-09-29 | Ici Ltd | Manufacture of pyridine and alkylpyridines |
| NL6405359A (US08063081-20111122-C00242.png) * | 1963-06-06 | 1964-12-07 | ||
| NL127993C (US08063081-20111122-C00242.png) * | 1964-10-15 | 1900-01-01 | ||
| BE790121A (fr) * | 1971-10-15 | 1973-02-01 | Degussa | Catalyseurs pour la preparation de pyridine et de 3-methylpyridine |
| DE2449340C2 (de) * | 1974-10-17 | 1987-04-09 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Pyridin und 3-Methylpyridin |
-
1977
- 1977-01-26 DE DE2703049A patent/DE2703049C2/de not_active Expired
- 1977-11-17 ES ES464217A patent/ES464217A1/es not_active Expired
- 1977-12-05 FR FR7736595A patent/FR2378764A1/fr active Granted
-
1978
- 1978-01-05 GB GB328/78A patent/GB1557526A/en not_active Expired
- 1978-01-06 NL NL7800217A patent/NL7800217A/xx not_active Application Discontinuation
- 1978-01-16 IL IL53819A patent/IL53819A/xx unknown
- 1978-01-19 IN IN76/CAL/78A patent/IN147407B/en unknown
- 1978-01-20 SU SU782568900A patent/SU670218A3/ru active
- 1978-01-24 US US05/871,976 patent/US4147874A/en not_active Expired - Lifetime
- 1978-01-24 IT IT47765/78A patent/IT1155787B/it active
- 1978-01-24 BR BR7800414A patent/BR7800414A/pt unknown
- 1978-01-25 CH CH81878A patent/CH633269A5/de not_active IP Right Cessation
- 1978-01-25 MX MX786791U patent/MX5066E/es unknown
- 1978-01-25 BE BE6046327A patent/BE863319A/xx not_active IP Right Cessation
- 1978-01-25 CA CA295,667A patent/CA1063122A/en not_active Expired
- 1978-01-25 SE SE7800931A patent/SE425734B/sv not_active IP Right Cessation
- 1978-01-26 JP JP781378A patent/JPS5392782A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1557526A (en) | 1979-12-12 |
| US4147874A (en) | 1979-04-03 |
| JPS5392782A (en) | 1978-08-15 |
| BE863319A (fr) | 1978-07-25 |
| SE425734B (sv) | 1982-11-01 |
| CA1063122A (en) | 1979-09-25 |
| IL53819A0 (en) | 1978-04-30 |
| SE7800931L (sv) | 1978-07-27 |
| FR2378764A1 (fr) | 1978-08-25 |
| IN147407B (US08063081-20111122-C00242.png) | 1980-02-16 |
| IT7847765A0 (it) | 1978-01-24 |
| FR2378764B1 (US08063081-20111122-C00242.png) | 1983-04-15 |
| BR7800414A (pt) | 1978-08-22 |
| SU670218A3 (ru) | 1979-06-25 |
| JPS6154785B2 (US08063081-20111122-C00242.png) | 1986-11-25 |
| IL53819A (en) | 1980-09-16 |
| IT1155787B (it) | 1987-01-28 |
| DE2703049A1 (de) | 1978-07-27 |
| CH633269A5 (de) | 1982-11-30 |
| NL7800217A (nl) | 1978-07-28 |
| MX5066E (es) | 1983-03-09 |
| ES464217A1 (es) | 1978-07-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2350212C3 (de) | Verfahren zur Herstellung von Cyanwasserstoff | |
| DE2732952C2 (de) | Verfahren zur Herstellung von Methacrylderivaten aus tert.-Butylgruppen enthaltenden Verbindungen | |
| DE2151417C3 (de) | Verfahren zur Herstellung von Katalysatoren | |
| DE2704991B2 (de) | Verfahren zur Herstellung von Methacrylsäure | |
| EP0170182B1 (de) | Verfahren zur Gewinnung von 2-Butenen aus 1-Buten und gegebenenfalls 2-Butene enthaltenden C4-Kohlenwasserstoffgemischen | |
| DE3149979A1 (de) | Verfahren zur herstellung von carbonsaeureestern | |
| DE2703049C2 (de) | Verfahren zur Herstellung von Pyridin und 3-Methylpyridin | |
| DE2703070C2 (US08063081-20111122-C00242.png) | ||
| EP0266689B1 (de) | Verfahren zur Herstellung von 4-Pentensäureestern | |
| DE2703069C2 (US08063081-20111122-C00242.png) | ||
| EP0249976B1 (de) | Verfahren zur Herstellung von Carbonsäuren | |
| DE2449340C2 (de) | Verfahren zur Herstellung von Pyridin und 3-Methylpyridin | |
| DE2739779C2 (de) | Molybdän, Vanadin, Phosphor sowie gegebenenfalls Kupfer, Zinn, Eisen, Blei und/oder Cer enthaltender Katalysator und dessen Verwendung zur Herstellung von Methacrylsäure | |
| DE69621628T2 (de) | Verfahren zur herstellung von ammoxidationskatalysatoren | |
| DE2726005C3 (de) | Verfahren zur Herstellung von Dimethylformamid | |
| DE69309106T2 (de) | Prozess zur herstellung von (meth)acrylnitril durch ammoxidation | |
| DE2641846A1 (de) | Uranoxid-antimonoxidverbindung sowie herstellung und verwendung derselben als katalysator | |
| DE2357248C2 (de) | Verfahren zur Herstellung von Acryl- bzw. Methacrylnitril | |
| DE69019301T2 (de) | Herstellungsverfahren von Indolen. | |
| DE2712694C2 (US08063081-20111122-C00242.png) | ||
| DE1964786C3 (de) | Verfahren zur Herstellung von Acrylnitril aus Propan | |
| CH638786A5 (de) | Verfahren zur herstellung substituierter pyridine. | |
| DE1177628B (de) | Verfahren zur Herstellung von Akrolein oder Methakrolein durch katalytisch Oxydation von Propylen oder Isobutylen. | |
| DE2112938A1 (de) | Oxydationskatalysator und seine Verwendung | |
| CH543510A (de) | Verfahren zur Herstellung von Pyridincarbonsäuren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |