DE2159846A1 - Herstellung von Pyridin und gegebenenfalls 2,6-Lutidin als Nebenprodukt - Google Patents
Herstellung von Pyridin und gegebenenfalls 2,6-Lutidin als NebenproduktInfo
- Publication number
- DE2159846A1 DE2159846A1 DE19712159846 DE2159846A DE2159846A1 DE 2159846 A1 DE2159846 A1 DE 2159846A1 DE 19712159846 DE19712159846 DE 19712159846 DE 2159846 A DE2159846 A DE 2159846A DE 2159846 A1 DE2159846 A1 DE 2159846A1
- Authority
- DE
- Germany
- Prior art keywords
- picoline
- catalyst
- lutidine
- pyridine
- water vapor
- 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.)
- Ceased
Links
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 title claims description 34
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 24
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 12
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 title claims description 6
- 239000006227 byproduct Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 230000017858 demethylation Effects 0.000 claims description 8
- 238000010520 demethylation reaction Methods 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 3
- 238000004508 fractional distillation Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 10
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WZOZCAZYAWIWQO-UHFFFAOYSA-N [Ni].[Ni]=O Chemical compound [Ni].[Ni]=O WZOZCAZYAWIWQO-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-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
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7017718.A NL167158C (nl) | 1970-12-04 | 1970-12-04 | Werkwijze voor de bereiding van pyridine door demethy- lering van alfa-picoline. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2159846A1 true DE2159846A1 (de) | 1972-06-22 |
Family
ID=19811721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712159846 Ceased DE2159846A1 (de) | 1970-12-04 | 1971-12-02 | Herstellung von Pyridin und gegebenenfalls 2,6-Lutidin als Nebenprodukt |
Country Status (14)
-
1970
- 1970-12-04 NL NL7017718.A patent/NL167158C/xx not_active IP Right Cessation
-
1971
- 1971-11-25 CA CA128,528A patent/CA949972A/en not_active Expired
- 1971-11-26 GB GB5509471A patent/GB1357207A/en not_active Expired
- 1971-11-29 ZA ZA717998A patent/ZA717998B/xx unknown
- 1971-12-01 CH CH1748771A patent/CH562796A5/xx not_active IP Right Cessation
- 1971-12-01 JP JP46097099A patent/JPS5024316B1/ja active Pending
- 1971-12-01 FR FR7143069A patent/FR2117222A5/fr not_active Expired
- 1971-12-01 AT AT1034571A patent/AT310752B/de not_active IP Right Cessation
- 1971-12-02 DE DE19712159846 patent/DE2159846A1/de not_active Ceased
- 1971-12-02 BE BE776165A patent/BE776165A/xx not_active IP Right Cessation
- 1971-12-02 BR BR8022/71A patent/BR7108022D0/pt unknown
- 1971-12-03 SE SE7115570A patent/SE391923B/xx unknown
- 1971-12-03 IT IT54520/71A patent/IT945266B/it active
- 1971-12-03 ES ES397650A patent/ES397650A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5024316B1 (enrdf_load_stackoverflow) | 1975-08-14 |
| ES397650A1 (es) | 1974-05-16 |
| IT945266B (it) | 1973-05-10 |
| GB1357207A (en) | 1974-06-19 |
| SE391923B (sv) | 1977-03-07 |
| FR2117222A5 (enrdf_load_stackoverflow) | 1972-07-21 |
| NL7017718A (enrdf_load_stackoverflow) | 1972-06-06 |
| CA949972A (en) | 1974-06-25 |
| NL167158C (nl) | 1981-11-16 |
| BE776165A (fr) | 1972-06-02 |
| BR7108022D0 (pt) | 1973-04-12 |
| ZA717998B (en) | 1972-08-30 |
| AT310752B (de) | 1973-10-10 |
| CH562796A5 (enrdf_load_stackoverflow) | 1975-06-13 |
| NL167158B (nl) | 1981-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8131 | Rejection |