DE2140649C3 - Verfahren zur Herstellung von Tetraalkylpyrazinen - Google Patents
Verfahren zur Herstellung von TetraalkylpyrazinenInfo
- Publication number
- DE2140649C3 DE2140649C3 DE2140649A DE2140649A DE2140649C3 DE 2140649 C3 DE2140649 C3 DE 2140649C3 DE 2140649 A DE2140649 A DE 2140649A DE 2140649 A DE2140649 A DE 2140649A DE 2140649 C3 DE2140649 C3 DE 2140649C3
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- ammonia
- butanolamine
- weight
- copper
- 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
- 239000003054 catalyst Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 15
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- FINHMKGKINIASC-UHFFFAOYSA-N Tetramethylpyrazine Chemical compound CC1=NC(C)=C(C)N=C1C FINHMKGKINIASC-UHFFFAOYSA-N 0.000 description 13
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 12
- 229910021529 ammonia Inorganic materials 0.000 description 12
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 10
- 239000010949 copper Substances 0.000 description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 229910052802 copper Inorganic materials 0.000 description 8
- LCZUOKDVTBMCMX-UHFFFAOYSA-N 2,5-Dimethylpyrazine Chemical compound CC1=CN=C(C)C=N1 LCZUOKDVTBMCMX-UHFFFAOYSA-N 0.000 description 6
- 239000011651 chromium Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910052804 chromium Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003216 pyrazines Chemical class 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000001934 2,5-dimethylpyrazine Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FSHMPNBRNOGDDK-UHFFFAOYSA-N 1,2,3,4,4a,5,5a,6-octahydrophenazine Chemical compound C1=CCC2NC(CCCC3)C3=NC2=C1 FSHMPNBRNOGDDK-UHFFFAOYSA-N 0.000 description 1
- PQMCFTMVQORYJC-UHFFFAOYSA-N 2-aminocyclohexan-1-ol Chemical compound NC1CCCCC1O PQMCFTMVQORYJC-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JYYRTWNCBVRKMN-UHFFFAOYSA-N Octahydrophenazine Natural products C1CCCC2=C1N=C1CCCCC1=N2 JYYRTWNCBVRKMN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GUQRKZPMVLRXLT-UHFFFAOYSA-N n-cyclohexylhydroxylamine Chemical compound ONC1CCCCC1 GUQRKZPMVLRXLT-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2140649A DE2140649C3 (de) | 1971-08-13 | 1971-08-13 | Verfahren zur Herstellung von Tetraalkylpyrazinen |
| BE787367A BE787367A (fr) | 1971-08-13 | 1972-08-09 | Procede de preparation de tetraalkylpyrazines et produits obtenus |
| JP47079570A JPS4828478A (cg-RX-API-DMAC10.html) | 1971-08-13 | 1972-08-10 | |
| CH1182472A CH572045A5 (cg-RX-API-DMAC10.html) | 1971-08-13 | 1972-08-10 | |
| US280015A US3925378A (en) | 1971-08-13 | 1972-08-11 | Tetraalkyl pyrazines from alkanolamines by copper-chromite catalysis |
| FR7229135A FR2150092A5 (cg-RX-API-DMAC10.html) | 1971-08-13 | 1972-08-11 | |
| NL7211045A NL7211045A (cg-RX-API-DMAC10.html) | 1971-08-13 | 1972-08-11 | |
| GB3763772A GB1382468A (en) | 1971-08-13 | 1972-08-11 | Process for making tetraalkylpyrazines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2140649A DE2140649C3 (de) | 1971-08-13 | 1971-08-13 | Verfahren zur Herstellung von Tetraalkylpyrazinen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2140649A1 DE2140649A1 (de) | 1973-02-22 |
| DE2140649B2 DE2140649B2 (de) | 1980-06-04 |
| DE2140649C3 true DE2140649C3 (de) | 1981-02-19 |
Family
ID=5816696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2140649A Expired DE2140649C3 (de) | 1971-08-13 | 1971-08-13 | Verfahren zur Herstellung von Tetraalkylpyrazinen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3925378A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS4828478A (cg-RX-API-DMAC10.html) |
| BE (1) | BE787367A (cg-RX-API-DMAC10.html) |
| CH (1) | CH572045A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2140649C3 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2150092A5 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1382468A (cg-RX-API-DMAC10.html) |
| NL (1) | NL7211045A (cg-RX-API-DMAC10.html) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4064124A (en) * | 1974-05-25 | 1977-12-20 | Basf Aktiengesellschaft | Manufacture of pyrazines |
| JPS5337675A (en) | 1976-09-20 | 1978-04-06 | Tokai Electro Chemical Co | Production of pyrazines |
| US4855431A (en) * | 1983-01-13 | 1989-08-08 | Mobil Oil Corp. | Process for making alkyl pyrazines |
| US4788289A (en) * | 1986-10-24 | 1988-11-29 | Texaco Inc. | Process for preparing pyrazines from hydroxyamines |
| US5304648A (en) * | 1992-09-29 | 1994-04-19 | Nestec S.A. | Pyrazine preparation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2813869A (en) * | 1957-03-29 | 1957-11-19 | Wyandotte Chemicals Corp | Vapor phase synthesis of carbon-substituted pyrazines and piperazines |
-
1971
- 1971-08-13 DE DE2140649A patent/DE2140649C3/de not_active Expired
-
1972
- 1972-08-09 BE BE787367A patent/BE787367A/xx unknown
- 1972-08-10 CH CH1182472A patent/CH572045A5/xx not_active IP Right Cessation
- 1972-08-10 JP JP47079570A patent/JPS4828478A/ja active Pending
- 1972-08-11 NL NL7211045A patent/NL7211045A/xx not_active Application Discontinuation
- 1972-08-11 FR FR7229135A patent/FR2150092A5/fr not_active Expired
- 1972-08-11 GB GB3763772A patent/GB1382468A/en not_active Expired
- 1972-08-11 US US280015A patent/US3925378A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| Nichts ermittelt * |
Also Published As
| Publication number | Publication date |
|---|---|
| US3925378A (en) | 1975-12-09 |
| GB1382468A (en) | 1975-01-29 |
| BE787367A (fr) | 1972-12-01 |
| CH572045A5 (cg-RX-API-DMAC10.html) | 1976-01-30 |
| JPS4828478A (cg-RX-API-DMAC10.html) | 1973-04-14 |
| DE2140649A1 (de) | 1973-02-22 |
| USB280015I5 (cg-RX-API-DMAC10.html) | 1975-01-28 |
| DE2140649B2 (de) | 1980-06-04 |
| FR2150092A5 (cg-RX-API-DMAC10.html) | 1973-03-30 |
| NL7211045A (cg-RX-API-DMAC10.html) | 1973-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OGA | New person/name/address of the applicant | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |