DE3410542A1 - Verfahren zur aromatisierung gesaettigter stickstoffhaltiger heterocyclen - Google Patents
Verfahren zur aromatisierung gesaettigter stickstoffhaltiger heterocyclenInfo
- Publication number
- DE3410542A1 DE3410542A1 DE19843410542 DE3410542A DE3410542A1 DE 3410542 A1 DE3410542 A1 DE 3410542A1 DE 19843410542 DE19843410542 DE 19843410542 DE 3410542 A DE3410542 A DE 3410542A DE 3410542 A1 DE3410542 A1 DE 3410542A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- alkaline earth
- aromatization
- dehydrogenation
- halide
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000005899 aromatization reaction Methods 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 32
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 11
- 229910052763 palladium Inorganic materials 0.000 claims description 10
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 8
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 239000010953 base metal Substances 0.000 claims description 2
- 239000001110 calcium chloride Substances 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- -1 3-ethyl pyrrolidine 3-ethyl pyrrole Chemical compound 0.000 description 3
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 description 3
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- COWPTMLRSANSMQ-UHFFFAOYSA-N 2,3-dimethylpiperazine Chemical compound CC1NCCNC1C COWPTMLRSANSMQ-UHFFFAOYSA-N 0.000 description 1
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 description 1
- DZFFQSFNUBWNSF-UHFFFAOYSA-N 3-ethylpyrrolidine Chemical compound CCC1CCNC1 DZFFQSFNUBWNSF-UHFFFAOYSA-N 0.000 description 1
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000004913 activation Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000007795 chemical reaction product 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
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- ZADYMNAVLSWLEQ-UHFFFAOYSA-N magnesium;oxygen(2-);silicon(4+) Chemical compound [O-2].[O-2].[O-2].[Mg+2].[Si+4] ZADYMNAVLSWLEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- ZNSWGHZWUUFFKV-UHFFFAOYSA-N piperidine;pyridine Chemical compound C1CCNCC1.C1=CC=NC=C1 ZNSWGHZWUUFFKV-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843410542 DE3410542A1 (de) | 1984-03-22 | 1984-03-22 | Verfahren zur aromatisierung gesaettigter stickstoffhaltiger heterocyclen |
| JP60050710A JPS60209563A (ja) | 1984-03-22 | 1985-03-15 | 飽和窒素含有複素環化合物の芳香族化方法 |
| EP85102997A EP0155649B1 (de) | 1984-03-22 | 1985-03-15 | Verfahren zur Aromatisierung gesättigter stickstoffhaltiger Heterocyclen |
| DE8585102997T DE3584845D1 (de) | 1984-03-22 | 1985-03-15 | Verfahren zur aromatisierung gesaettigter stickstoffhaltiger heterocyclen. |
| US07/058,622 US4762929A (en) | 1984-03-22 | 1987-06-04 | Aromatization of saturated nitrogen-containing heterocycles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843410542 DE3410542A1 (de) | 1984-03-22 | 1984-03-22 | Verfahren zur aromatisierung gesaettigter stickstoffhaltiger heterocyclen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3410542A1 true DE3410542A1 (de) | 1985-10-03 |
Family
ID=6231291
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843410542 Withdrawn DE3410542A1 (de) | 1984-03-22 | 1984-03-22 | Verfahren zur aromatisierung gesaettigter stickstoffhaltiger heterocyclen |
| DE8585102997T Expired - Lifetime DE3584845D1 (de) | 1984-03-22 | 1985-03-15 | Verfahren zur aromatisierung gesaettigter stickstoffhaltiger heterocyclen. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8585102997T Expired - Lifetime DE3584845D1 (de) | 1984-03-22 | 1985-03-15 | Verfahren zur aromatisierung gesaettigter stickstoffhaltiger heterocyclen. |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4762929A (enExample) |
| EP (1) | EP0155649B1 (enExample) |
| JP (1) | JPS60209563A (enExample) |
| DE (2) | DE3410542A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102023120080A1 (de) * | 2023-07-28 | 2025-01-30 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Verfahren und Vorrichtung zur Dehydrierung von Wasserstoffträgern |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR900003091B1 (ko) * | 1987-12-31 | 1990-05-07 | 재단법인 한국화학연구소 | 피라진류의 제조방법 |
| DE19918568A1 (de) * | 1999-04-23 | 2000-10-26 | Basf Ag | Verfahren zur Herstellung von Pyrrolen |
| DE10144631A1 (de) | 2001-09-11 | 2003-03-27 | Basf Ag | Verfahren zur Herstellung von Pyrrol und Pyridin |
| CN101384525B (zh) | 2006-02-15 | 2012-09-05 | 巴斯夫欧洲公司 | 脱氢方法 |
| CN107573272A (zh) * | 2017-10-09 | 2018-01-12 | 迈奇化学股份有限公司 | 一种n‑甲基吡咯的制备方法 |
| CN113617354B (zh) * | 2021-07-08 | 2023-06-27 | 南京红太阳生物化学有限责任公司 | 一种3-甲基哌啶脱氢催化剂及其制备方法与应用 |
| CN119215942A (zh) * | 2024-09-04 | 2024-12-31 | 中国天辰工程有限公司 | 一种用于制备氮杂芳环的脱氢催化剂及其制备方法与应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA653723A (en) * | 1962-12-11 | G. Jeffers Francis | Catalytic dehydrogenation of n-methylpyrrolidine to n-methylpyrrole | |
| DE1024080B (de) * | 1953-06-19 | 1958-02-13 | Ici Ltd | Verfahren zur katalytischen Dehydrierung von Piperidin zu Pyridin |
| DE1192648B (de) * | 1955-11-04 | 1965-05-13 | Hoechst Ag | Verfahren zur Herstellung von Pyridin durch katalytische Dehydrierung von dampffoermigem Piperidin |
| GB1393088A (en) * | 1971-06-09 | 1975-05-07 | Ici Ltd | Dehydrogenation of piperidine using palladium on silica catalyst |
| GB1393086A (en) * | 1971-06-09 | 1975-05-07 | Ici Ltd | Palladium on silica catalyst |
| US4118400A (en) * | 1977-09-22 | 1978-10-03 | Fmc Corporation | Process for preparing 2,3-dihydro-7-benzofuranols and benzodioxole intermediate therefor |
| FR2503156A1 (fr) * | 1981-04-01 | 1982-10-08 | Rhone Poulenc Spec Chim | Procede de preparation de pyridine et de pyridines substituees |
| DE3123302A1 (de) * | 1981-06-12 | 1983-01-05 | Basf Ag, 6700 Ludwigshafen | "verfahren zur herstellung von pyrrolen" |
| DE3227022A1 (de) * | 1982-07-20 | 1984-01-26 | Rütgerswerke AG, 6000 Frankfurt | Verfahren zur katalytischen dehydrierung von piperidin |
| JPS60169468A (ja) * | 1984-02-15 | 1985-09-02 | Koei Chem Co Ltd | ピラジン類を製造する方法 |
-
1984
- 1984-03-22 DE DE19843410542 patent/DE3410542A1/de not_active Withdrawn
-
1985
- 1985-03-15 DE DE8585102997T patent/DE3584845D1/de not_active Expired - Lifetime
- 1985-03-15 EP EP85102997A patent/EP0155649B1/de not_active Expired - Lifetime
- 1985-03-15 JP JP60050710A patent/JPS60209563A/ja active Granted
-
1987
- 1987-06-04 US US07/058,622 patent/US4762929A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102023120080A1 (de) * | 2023-07-28 | 2025-01-30 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Verfahren und Vorrichtung zur Dehydrierung von Wasserstoffträgern |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3584845D1 (de) | 1992-01-23 |
| EP0155649B1 (de) | 1991-12-11 |
| JPH0535140B2 (enExample) | 1993-05-25 |
| EP0155649A3 (en) | 1988-06-01 |
| US4762929A (en) | 1988-08-09 |
| JPS60209563A (ja) | 1985-10-22 |
| EP0155649A2 (de) | 1985-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |