CA1072563A - Process for the production of 3-methyl pyridine - Google Patents
Process for the production of 3-methyl pyridineInfo
- Publication number
- CA1072563A CA1072563A CA295,631A CA295631A CA1072563A CA 1072563 A CA1072563 A CA 1072563A CA 295631 A CA295631 A CA 295631A CA 1072563 A CA1072563 A CA 1072563A
- Authority
- CA
- Canada
- Prior art keywords
- ammonia
- acrolein
- propionaldehyde
- mole ratio
- aldehyde
- 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 abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 31
- 230000008569 process Effects 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims abstract description 42
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 40
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims abstract description 36
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 20
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 239000011148 porous material Substances 0.000 claims abstract description 14
- 229910000323 aluminium silicate Inorganic materials 0.000 claims abstract description 10
- 235000012211 aluminium silicate Nutrition 0.000 claims abstract description 10
- 150000001299 aldehydes Chemical class 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000011261 inert gas Substances 0.000 claims description 4
- 150000004760 silicates Chemical class 0.000 claims description 2
- 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 6
- 230000000875 corresponding effect Effects 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 239000005995 Aluminium silicate Substances 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
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000001164 aluminium sulphate Substances 0.000 description 1
- 235000011128 aluminium sulphate Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000001301 oxygen Substances 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
- 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
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000005496 tempering Methods 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
- C07D213/08—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)
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 (1)
| Publication Number | Publication Date |
|---|---|
| CA1072563A true CA1072563A (en) | 1980-02-26 |
Family
ID=5999552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA295,631A Expired CA1072563A (en) | 1977-01-26 | 1978-01-25 | Process for the production of 3-methyl pyridine |
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]) |
Families Citing this family (9)
| 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 |
| FI77025C (fi) * | 1981-03-18 | 1989-01-10 | Lonza Ag | Foerfarande foer framstaellning av 3-pikolin. |
| US4701530A (en) * | 1985-11-12 | 1987-10-20 | The Dow Chemical Company | Two-stage process for making trimethyl pyridine |
| DE3634259A1 (de) * | 1986-10-08 | 1988-04-21 | Basf Ag | Verfahren zur herstellung von substituierten pyridinen |
| DE3741160A1 (de) * | 1987-12-04 | 1989-06-15 | Basf Ag | Verfahren zur herstellung von substituierten pyridinen |
| DE3741159A1 (de) * | 1987-12-04 | 1989-06-15 | Basf Ag | Verfahren zur herstellung von cyano-pyridinen |
| 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 |
| 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 |
Family Cites Families (7)
| 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 |
| 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 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
Also Published As
| Publication number | Publication date |
|---|---|
| IL53817A (en) | 1980-09-16 |
| FR2378766B1 (en]) | 1983-02-04 |
| FR2378766A1 (fr) | 1978-08-25 |
| 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 |
| DE2703070A1 (de) | 1978-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |