DE1903879A1 - Verfahren zur Herstellung von alpha-und gamma-Picolin - Google Patents
Verfahren zur Herstellung von alpha-und gamma-PicolinInfo
- Publication number
- DE1903879A1 DE1903879A1 DE19691903879 DE1903879A DE1903879A1 DE 1903879 A1 DE1903879 A1 DE 1903879A1 DE 19691903879 DE19691903879 DE 19691903879 DE 1903879 A DE1903879 A DE 1903879A DE 1903879 A1 DE1903879 A1 DE 1903879A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- alumina
- fluoride
- silica
- amount
- 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
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 title description 4
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 title 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 239000000377 silicon dioxide Substances 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- 239000003607 modifier Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 150000002736 metal compounds Chemical class 0.000 claims description 4
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 claims description 4
- 229910052793 cadmium Inorganic materials 0.000 claims description 3
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 3
- YAFKGUAJYKXPDI-UHFFFAOYSA-J lead tetrafluoride Chemical compound F[Pb](F)(F)F YAFKGUAJYKXPDI-UHFFFAOYSA-J 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- LVEULQCPJDDSLD-UHFFFAOYSA-L cadmium fluoride Chemical compound F[Cd]F LVEULQCPJDDSLD-UHFFFAOYSA-L 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910000464 lead oxide Inorganic materials 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 239000012808 vapor phase Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- CXKCTMHTOKXKQT-UHFFFAOYSA-N cadmium oxide Inorganic materials [Cd]=O CXKCTMHTOKXKQT-UHFFFAOYSA-N 0.000 claims 1
- CFEAAQFZALKQPA-UHFFFAOYSA-N cadmium(2+);oxygen(2-) Chemical compound [O-2].[Cd+2] CFEAAQFZALKQPA-UHFFFAOYSA-N 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 5
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
- 239000005956 Metaldehyde Substances 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- -1 acetates Chemical class 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- PIJPYDMVFNTHIP-UHFFFAOYSA-L lead sulfate Chemical compound [PbH4+2].[O-]S([O-])(=O)=O PIJPYDMVFNTHIP-UHFFFAOYSA-L 0.000 description 1
- HWSZZLVAJGOAAY-UHFFFAOYSA-L lead(II) chloride Chemical compound Cl[Pb]Cl HWSZZLVAJGOAAY-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GKKDCARASOJPNG-UHFFFAOYSA-N metaldehyde Chemical compound CC1OC(C)OC(C)OC(C)O1 GKKDCARASOJPNG-UHFFFAOYSA-N 0.000 description 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
- 229960003868 paraldehyde Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 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
-
- 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
- B01J27/12—Fluorides
-
- 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
- C07D213/10—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from acetaldehyde or cyclic polymers thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB437868A GB1188891A (en) | 1968-01-27 | 1968-01-27 | Picolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1903879A1 true DE1903879A1 (de) | 1969-10-30 |
Family
ID=9776040
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691903879 Pending DE1903879A1 (de) | 1968-01-27 | 1969-01-27 | Verfahren zur Herstellung von alpha-und gamma-Picolin |
| DE19691903878 Pending DE1903878A1 (de) | 1968-01-27 | 1969-01-27 | Verfahren zur Herstellung von Pyridin und ss-Picolin |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691903878 Pending DE1903878A1 (de) | 1968-01-27 | 1969-01-27 | Verfahren zur Herstellung von Pyridin und ss-Picolin |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE727469A (enrdf_load_stackoverflow) |
| DE (2) | DE1903879A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2000862A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1188891A (enrdf_load_stackoverflow) |
| NL (2) | NL6900935A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0173336A3 (en) * | 1984-08-31 | 1988-09-21 | Toyota Jidosha Kabushiki Kaisha | Roof door structure for vehicles |
| WO1990003366A1 (en) * | 1988-09-30 | 1990-04-05 | Reilly Industries, Inc. | Pyridine base synthesis process and catalyst for same |
| WO2021086679A1 (en) | 2019-10-29 | 2021-05-06 | W.R. Grace & Co.-Conn. | Modified zeolite catalyst compositions and methods of use |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3946020A (en) * | 1970-12-28 | 1976-03-23 | Koei Chemical Co., Ltd. | Process for producing pyridine bases |
| JPS5347111B2 (enrdf_load_stackoverflow) * | 1972-05-02 | 1978-12-19 | ||
| ATE5719T1 (de) * | 1980-05-23 | 1984-01-15 | Lonza Ag | Verfahren zur herstellung von 3-picolin. |
| EP0131887B1 (en) * | 1983-07-11 | 1989-01-25 | Nepera, Inc. | Improved process for preparing pyridine-type bases in a fluid bed using a crystalline aluminosilicate zeolite catalyst |
| US5218122A (en) * | 1988-09-30 | 1993-06-08 | Reilly Industries, Inc. | Pyridine base synthesis process and catalyst for same |
-
1968
- 1968-01-27 GB GB437868A patent/GB1188891A/en not_active Expired
-
1969
- 1969-01-20 NL NL6900935A patent/NL6900935A/xx unknown
- 1969-01-21 NL NL6900997A patent/NL6900997A/xx unknown
- 1969-01-27 DE DE19691903879 patent/DE1903879A1/de active Pending
- 1969-01-27 DE DE19691903878 patent/DE1903878A1/de active Pending
- 1969-01-27 FR FR6901494A patent/FR2000862A1/fr not_active Withdrawn
- 1969-01-27 BE BE727469D patent/BE727469A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0173336A3 (en) * | 1984-08-31 | 1988-09-21 | Toyota Jidosha Kabushiki Kaisha | Roof door structure for vehicles |
| WO1990003366A1 (en) * | 1988-09-30 | 1990-04-05 | Reilly Industries, Inc. | Pyridine base synthesis process and catalyst for same |
| WO2021086679A1 (en) | 2019-10-29 | 2021-05-06 | W.R. Grace & Co.-Conn. | Modified zeolite catalyst compositions and methods of use |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2000862A1 (enrdf_load_stackoverflow) | 1969-09-12 |
| GB1188891A (en) | 1970-04-22 |
| BE727469A (enrdf_load_stackoverflow) | 1969-07-28 |
| NL6900935A (enrdf_load_stackoverflow) | 1969-07-29 |
| NL6900997A (enrdf_load_stackoverflow) | 1969-07-29 |
| DE1903878A1 (de) | 1969-09-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1643087C3 (de) | Verfahren zur Herstellung von Acrylsäure durch Oxidation von Acrolein | |
| DE1903879A1 (de) | Verfahren zur Herstellung von alpha-und gamma-Picolin | |
| DE68916195T2 (de) | Verfahren zur Herstellung von Heteropolysäurekatalysatoren. | |
| DE2652989B2 (enrdf_load_stackoverflow) | ||
| DE1282823B (de) | Verfahren zum hydrierenden Spalten von Kohlenwasserstoffen | |
| DE2746177C2 (de) | Verfahren zur Herstellung von Pyridinbasen | |
| EP0235841A1 (de) | Verfahren zur Herstellung von Kupferhydroxid | |
| DE1289528B (de) | Verfahren zur kontinuierlichen Herstellung von ª‡- und ª†-Picolin | |
| DE1177628B (de) | Verfahren zur Herstellung von Akrolein oder Methakrolein durch katalytisch Oxydation von Propylen oder Isobutylen. | |
| DE2234719C3 (de) | Verfahren zur Herstellung von Calciumphosphat | |
| DE3880272T2 (de) | Katalysatoren und deren verwendung in der hydrolyse von nitrilen. | |
| DE1468073A1 (de) | Verfahren zur Herstellung von chlorierten Kohlenwasserstoffen | |
| DE2038641B2 (de) | Durch ionisierende strahlung haertbare anstrichmittel sowie deren verwendung | |
| DE939720C (de) | Galvanisches Versilberungsbad | |
| DE394816C (de) | Verfahren zur Herstellung festhaftender Metallueberzuege auf Aluminium und Aluminiumlegierungen | |
| DE1125899B (de) | Verfahren zur Herstellung von AEthylenoxyd | |
| DE1593470C2 (enrdf_load_stackoverflow) | ||
| AT221078B (de) | Verfahren zur Herstellung eines verbesserten Katalysators auf Basis von Silber zur katalytischen Oxydation von Olefinen | |
| DE3635219A1 (de) | Verfahren zur oxidation von waschwaessern geringer thiosulfatkonzentration | |
| DE2359546A1 (de) | Katalysator und verfahren zur herstellung von acrylnitril, acrylsaeure und acrolein und verfahren zur herstellung des katalysators | |
| DE1211607B (de) | Verfahren zur Herstellung von Silberkatalysatoren fuer die Herstellung von AEthylenoxyd | |
| DE125490C (enrdf_load_stackoverflow) | ||
| DE1801301A1 (de) | Verfahren zur Herstellung von Ketonen und/oder Aldehyden aus Olefinen | |
| DE2004253C (de) | Verfahren zur Herstellung von Ruß in Gegenwart von Zusätzen, die die Rußeigenschaften beeinflussen | |
| DE1442521C (de) | Verfahren zur Herstellung von Platin katalysatoren |