DE2703070A1 - Verfahren zur herstellung von 3-methylpyridin - Google Patents
Verfahren zur herstellung von 3-methylpyridinInfo
- Publication number
- DE2703070A1 DE2703070A1 DE19772703070 DE2703070A DE2703070A1 DE 2703070 A1 DE2703070 A1 DE 2703070A1 DE 19772703070 DE19772703070 DE 19772703070 DE 2703070 A DE2703070 A DE 2703070A DE 2703070 A1 DE2703070 A1 DE 2703070A1
- Authority
- DE
- Germany
- Prior art keywords
- methylpyridine
- acrolein
- ammonia
- propionaldehyde
- yield
- 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.)
- Granted
Links
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 34
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 30
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 28
- 229910021529 ammonia Inorganic materials 0.000 claims description 15
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000011148 porous material Substances 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 5
- -1 aluminum silicates Chemical class 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 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
- 239000011261 inert gas Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver 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 (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772703070 DE2703070A1 (de) | 1977-01-26 | 1977-01-26 | Verfahren zur herstellung von 3-methylpyridin |
| ES464219A ES464219A1 (es) | 1977-01-26 | 1977-11-17 | Procedimiento para la preparacion de 3-metilpiridina. |
| FR7736600A FR2378766A1 (fr) | 1977-01-26 | 1977-12-05 | Procede de preparation de 3-methylpyridine |
| GB326/78A GB1560462A (en) | 1977-01-26 | 1978-01-05 | Process for the production of 3 - methyl pyridine |
| NL7800214A NL7800214A (nl) | 1977-01-26 | 1978-01-06 | Werkwijze voor het bereiden van 3-methylpyridine. |
| IL53817A IL53817A (en) | 1977-01-26 | 1978-01-16 | Process for the production of 3-methylpyridine |
| IN74/CAL/78A IN147430B (en]) | 1977-01-26 | 1978-01-19 | |
| SU782569345A SU679137A3 (ru) | 1977-01-26 | 1978-01-20 | Способ получени 3-метилпиридина |
| BR7800416A BR7800416A (pt) | 1977-01-26 | 1978-01-24 | Processo para a producao de 3-metilpiridina |
| US05/871,979 US4163854A (en) | 1977-01-26 | 1978-01-24 | Process for the production of 3-methyl pyridine |
| IT47767/78A IT1155789B (it) | 1977-01-26 | 1978-01-24 | Procedimento per la produzione di 3-metilpiridina |
| CA295,631A CA1072563A (en) | 1977-01-26 | 1978-01-25 | Process for the production of 3-methyl pyridine |
| CH81678A CH633267A5 (de) | 1977-01-26 | 1978-01-25 | Verfahren zur herstellung von 3-methylpyridin. |
| BE6046325A BE863317A (fr) | 1977-01-26 | 1978-01-25 | Procede de fabrication de 3-methylpyridine et produits obtenus |
| SE7800933A SE425735B (sv) | 1977-01-26 | 1978-01-25 | Forfarande for framstellning av 3-metylpyridin |
| JP53007811A JPS587623B2 (ja) | 1977-01-26 | 1978-01-26 | ３↓−メチルピリジンの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772703070 DE2703070A1 (de) | 1977-01-26 | 1977-01-26 | Verfahren zur herstellung von 3-methylpyridin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2703070A1 true DE2703070A1 (de) | 1978-07-27 |
| DE2703070C2 DE2703070C2 (en]) | 1987-07-30 |
Family
ID=5999552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772703070 Granted DE2703070A1 (de) | 1977-01-26 | 1977-01-26 | Verfahren zur herstellung von 3-methylpyridin |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4163854A (en]) |
| JP (1) | JPS587623B2 (en]) |
| BE (1) | BE863317A (en]) |
| BR (1) | BR7800416A (en]) |
| CA (1) | CA1072563A (en]) |
| CH (1) | CH633267A5 (en]) |
| DE (1) | DE2703070A1 (en]) |
| ES (1) | ES464219A1 (en]) |
| FR (1) | FR2378766A1 (en]) |
| GB (1) | GB1560462A (en]) |
| IL (1) | IL53817A (en]) |
| IN (1) | IN147430B (en]) |
| IT (1) | IT1155789B (en]) |
| NL (1) | NL7800214A (en]) |
| SE (1) | SE425735B (en]) |
| SU (1) | SU679137A3 (en]) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220783A (en) * | 1979-05-09 | 1980-09-02 | Mobil Oil Corporation | Synthesis of pyridine and alkylpyridines |
| EP0060551A1 (de) * | 1981-03-18 | 1982-09-22 | Lonza Ag | Verfahren zur Herstellung von 3-Picolin |
| EP0263464A3 (de) * | 1986-10-08 | 1990-05-23 | Degussa Ag | Verfahren zur Herstellung von substituierten Pyridinen |
| US4931564A (en) * | 1987-12-04 | 1990-06-05 | Basf Aktiengesellschaft | Preparation of cyanopyridines |
| EP2280002A1 (de) | 2009-07-29 | 2011-02-02 | Lonza Ltd. | Verfahren zur selektiven Herstellung von 3-Methylpyridin (3-Picolin) aus Acrolein und einem oder mehreren in Wasser gelösten Ammoniumsalzen |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2639701A1 (de) * | 1976-09-03 | 1978-03-09 | Degussa | Verfahren zur herstellung substituierter pyridine |
| US4701530A (en) * | 1985-11-12 | 1987-10-20 | The Dow Chemical Company | Two-stage process for making trimethyl pyridine |
| DE3741160A1 (de) * | 1987-12-04 | 1989-06-15 | Basf Ag | Verfahren zur herstellung von substituierten pyridinen |
| RU2474473C1 (ru) * | 2011-09-16 | 2013-02-10 | Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации | КАТАЛИЗАТОР, СПОСОБ ЕГО ПРИГОТОВЛЕНИЯ И СПОСОБ ПОЛУЧЕНИЯ β-ПИКОЛИНА |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2449340A1 (de) * | 1974-10-17 | 1976-04-22 | Degussa | Verfahren zur herstellung von pyridin und 3-methylpyridin |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6405359A (en]) * | 1963-06-06 | 1964-12-07 | ||
| NL127993C (en]) * | 1964-10-15 | 1900-01-01 | ||
| GB1182705A (en) * | 1966-09-21 | 1970-03-04 | Lummus Co | Improvements in or relating to the Vapour Phase Production of Pyridine of Alkyl Pyridines |
| BE790121A (fr) * | 1971-10-15 | 1973-02-01 | Degussa | Catalyseurs pour la preparation de pyridine et de 3-methylpyridine |
| DE2224160C3 (de) * | 1972-05-18 | 1979-10-04 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von Katalysatoren für die Herstellung von Pyridin und 3-Methylpyridin |
| DE2239801C3 (de) * | 1972-08-12 | 1979-08-23 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von Katalysatoren |
-
1977
- 1977-01-26 DE DE19772703070 patent/DE2703070A1/de active Granted
- 1977-11-17 ES ES464219A patent/ES464219A1/es not_active Expired
- 1977-12-05 FR FR7736600A patent/FR2378766A1/fr active Granted
-
1978
- 1978-01-05 GB GB326/78A patent/GB1560462A/en not_active Expired
- 1978-01-06 NL NL7800214A patent/NL7800214A/xx not_active Application Discontinuation
- 1978-01-16 IL IL53817A patent/IL53817A/xx unknown
- 1978-01-19 IN IN74/CAL/78A patent/IN147430B/en unknown
- 1978-01-20 SU SU782569345A patent/SU679137A3/ru active
- 1978-01-24 US US05/871,979 patent/US4163854A/en not_active Expired - Lifetime
- 1978-01-24 IT IT47767/78A patent/IT1155789B/it active
- 1978-01-24 BR BR7800416A patent/BR7800416A/pt unknown
- 1978-01-25 SE SE7800933A patent/SE425735B/sv not_active IP Right Cessation
- 1978-01-25 CH CH81678A patent/CH633267A5/de not_active IP Right Cessation
- 1978-01-25 CA CA295,631A patent/CA1072563A/en not_active Expired
- 1978-01-25 BE BE6046325A patent/BE863317A/xx not_active IP Right Cessation
- 1978-01-26 JP JP53007811A patent/JPS587623B2/ja not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2449340A1 (de) * | 1974-10-17 | 1976-04-22 | Degussa | Verfahren zur herstellung von pyridin und 3-methylpyridin |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220783A (en) * | 1979-05-09 | 1980-09-02 | Mobil Oil Corporation | Synthesis of pyridine and alkylpyridines |
| EP0060551A1 (de) * | 1981-03-18 | 1982-09-22 | Lonza Ag | Verfahren zur Herstellung von 3-Picolin |
| EP0263464A3 (de) * | 1986-10-08 | 1990-05-23 | Degussa Ag | Verfahren zur Herstellung von substituierten Pyridinen |
| US5079367A (en) * | 1986-10-08 | 1992-01-07 | Basf Aktiengesellschaft | Preparation of 3-hydrocarbyl substituted pyridines |
| US4931564A (en) * | 1987-12-04 | 1990-06-05 | Basf Aktiengesellschaft | Preparation of cyanopyridines |
| EP2280002A1 (de) | 2009-07-29 | 2011-02-02 | Lonza Ltd. | Verfahren zur selektiven Herstellung von 3-Methylpyridin (3-Picolin) aus Acrolein und einem oder mehreren in Wasser gelösten Ammoniumsalzen |
| WO2011012252A1 (en) | 2009-07-29 | 2011-02-03 | Lonza Ltd | Process for the selective preparation of 3-methylpyridine (3-picoline) from acrolein and one or more ammonium salts dissolved in water |
Also Published As
| Publication number | Publication date |
|---|---|
| IL53817A (en) | 1980-09-16 |
| FR2378766B1 (en]) | 1983-02-04 |
| FR2378766A1 (fr) | 1978-08-25 |
| CA1072563A (en) | 1980-02-26 |
| CH633267A5 (de) | 1982-11-30 |
| IT1155789B (it) | 1987-01-28 |
| SU679137A3 (ru) | 1979-08-05 |
| SE425735B (sv) | 1982-11-01 |
| IL53817A0 (en) | 1978-04-30 |
| DE2703070C2 (en]) | 1987-07-30 |
| ES464219A1 (es) | 1978-07-16 |
| GB1560462A (en) | 1980-02-06 |
| IN147430B (en]) | 1980-02-23 |
| BE863317A (fr) | 1978-07-25 |
| NL7800214A (nl) | 1978-07-28 |
| JPS587623B2 (ja) | 1983-02-10 |
| US4163854A (en) | 1979-08-07 |
| BR7800416A (pt) | 1978-08-22 |
| IT7847767A0 (it) | 1978-01-24 |
| JPS5392780A (en) | 1978-08-15 |
| SE7800933L (sv) | 1978-07-27 |
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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 |