DE1795315A1 - Verfahren zur katalytischen Dehydrierung von Pyrrolidin zu Pyrrol - Google Patents
Verfahren zur katalytischen Dehydrierung von Pyrrolidin zu PyrrolInfo
- Publication number
- DE1795315A1 DE1795315A1 DE19681795315 DE1795315A DE1795315A1 DE 1795315 A1 DE1795315 A1 DE 1795315A1 DE 19681795315 DE19681795315 DE 19681795315 DE 1795315 A DE1795315 A DE 1795315A DE 1795315 A1 DE1795315 A1 DE 1795315A1
- Authority
- DE
- Germany
- Prior art keywords
- pyrrolidine
- pyrrole
- catalyst
- silica gel
- hydrogen
- 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.)
- Pending
Links
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title claims description 54
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 19
- 230000003197 catalytic effect Effects 0.000 title claims description 12
- 238000006356 dehydrogenation reaction Methods 0.000 title claims description 9
- 239000003054 catalyst Substances 0.000 claims description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- 239000000741 silica gel Substances 0.000 claims description 11
- 229910002027 silica gel Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229910020175 SiOH Inorganic materials 0.000 claims description 9
- 125000005372 silanol group Chemical group 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 5
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 5
- 239000012808 vapor phase Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 231100000572 poisoning Toxicity 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 230000004580 weight loss Effects 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/08—Silica
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66737467A | 1967-09-13 | 1967-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1795315A1 true DE1795315A1 (de) | 1972-01-05 |
Family
ID=24677967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681795315 Pending DE1795315A1 (de) | 1967-09-13 | 1968-09-11 | Verfahren zur katalytischen Dehydrierung von Pyrrolidin zu Pyrrol |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3522269A (enExample) |
| AT (1) | AT277232B (enExample) |
| CH (1) | CH497421A (enExample) |
| DE (1) | DE1795315A1 (enExample) |
| FR (1) | FR1579449A (enExample) |
| GB (1) | GB1184862A (enExample) |
| NL (1) | NL6813153A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1222948B (de) * | 1960-03-08 | 1966-08-18 | Ind Companie Kleinewefers Kons | Rekuperativ-Waermeaustauscher |
| EP1046639A1 (de) * | 1999-04-23 | 2000-10-25 | Basf Aktiengesellschaft | Verfahren zur Herstellung von Pyrrolen |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2757923A1 (de) * | 1977-12-24 | 1979-06-28 | Hoechst Ag | Verfahren zur herstellung von 3-pyridazonen |
| DE3123302A1 (de) * | 1981-06-12 | 1983-01-05 | Basf Ag, 6700 Ludwigshafen | "verfahren zur herstellung von pyrrolen" |
| DE10144631A1 (de) | 2001-09-11 | 2003-03-27 | Basf Ag | Verfahren zur Herstellung von Pyrrol und Pyridin |
| US7943547B2 (en) * | 2005-09-14 | 2011-05-17 | Hamilton Sundstrand Space Systems International, Inc. | Selective catalytic oxidation of ammonia to water and nitrogen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB832855A (en) * | 1957-11-01 | 1960-04-13 | Ici Ltd | Catalytic dehydrogenation of n-methylpyrrolidine |
| US3008965A (en) * | 1959-10-21 | 1961-11-14 | Ansul Chemical Co | Dehydrogenation of nitrogen heterocyclics |
-
1967
- 1967-09-13 US US667374A patent/US3522269A/en not_active Expired - Lifetime
-
1968
- 1968-09-02 CH CH1314168A patent/CH497421A/de not_active IP Right Cessation
- 1968-09-11 DE DE19681795315 patent/DE1795315A1/de active Pending
- 1968-09-12 AT AT890668A patent/AT277232B/de not_active IP Right Cessation
- 1968-09-12 FR FR1579449D patent/FR1579449A/fr not_active Expired
- 1968-09-12 GB GB43329/63A patent/GB1184862A/en not_active Expired
- 1968-09-13 NL NL6813153A patent/NL6813153A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1222948B (de) * | 1960-03-08 | 1966-08-18 | Ind Companie Kleinewefers Kons | Rekuperativ-Waermeaustauscher |
| EP1046639A1 (de) * | 1999-04-23 | 2000-10-25 | Basf Aktiengesellschaft | Verfahren zur Herstellung von Pyrrolen |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6813153A (enExample) | 1969-03-17 |
| CH497421A (de) | 1970-10-15 |
| AT277232B (de) | 1969-12-10 |
| US3522269A (en) | 1970-07-28 |
| FR1579449A (enExample) | 1969-08-22 |
| GB1184862A (en) | 1970-03-18 |
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