DE1276644B - Verfahren zur Herstellung von Alkylpyridinen - Google Patents
Verfahren zur Herstellung von AlkylpyridinenInfo
- Publication number
- DE1276644B DE1276644B DES93642A DES0093642A DE1276644B DE 1276644 B DE1276644 B DE 1276644B DE S93642 A DES93642 A DE S93642A DE S0093642 A DES0093642 A DE S0093642A DE 1276644 B DE1276644 B DE 1276644B
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- phosphate
- ammonia
- aluminum
- aldehyde
- 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
- -1 alkyl pyridines Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 32
- 229910021529 ammonia Inorganic materials 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- AJJBCQJUDJPUJP-UHFFFAOYSA-K aluminum cobalt(2+) phosphate Chemical compound P(=O)([O-])([O-])[O-].[Al+3].[Co+2] AJJBCQJUDJPUJP-UHFFFAOYSA-K 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- 229910000831 Steel Inorganic materials 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 239000010959 steel Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000008246 gaseous mixture Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 22
- 150000001299 aldehydes Chemical class 0.000 description 12
- QLUUXTUCKOZMEL-UHFFFAOYSA-N 2-ethyl-3,5-dimethylpyridine Chemical compound CCC1=NC=C(C)C=C1C QLUUXTUCKOZMEL-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 235000021317 phosphate Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 4
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- CZESXOCCJVKONH-UHFFFAOYSA-N 2-(2-methylpropyl)-3,5-di(propan-2-yl)pyridine Chemical compound CC(C)CC1=NC=C(C(C)C)C=C1C(C)C CZESXOCCJVKONH-UHFFFAOYSA-N 0.000 description 1
- SCJHPUGWYHCYAZ-UHFFFAOYSA-N 3,5-diethyl-2-propylpyridine Chemical compound CCCC1=NC=C(CC)C=C1CC SCJHPUGWYHCYAZ-UHFFFAOYSA-N 0.000 description 1
- WWMYVQLEAVFYAP-UHFFFAOYSA-N 4-ethyl-3,5-dimethylpyridine Chemical compound CCC1=C(C)C=NC=C1C WWMYVQLEAVFYAP-UHFFFAOYSA-N 0.000 description 1
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910017119 AlPO Inorganic materials 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 101100356682 Caenorhabditis elegans rho-1 gene Proteins 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- RHBRWKIPYGZNMP-UHFFFAOYSA-N [O--].[O--].[O--].[Al+3].[Cr+3] Chemical compound [O--].[O--].[O--].[Al+3].[Cr+3] RHBRWKIPYGZNMP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012808 vapor phase 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
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
- B01J27/18—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr with metals other than Al or Zr
- B01J27/1802—Salts or mixtures of anhydrides with compounds of other metals than V, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, e.g. phosphates, thiophosphates
-
- 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
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/185—Phosphorus; Compounds thereof with iron group metals or platinum group metals
- B01J27/1853—Phosphorus; Compounds thereof with iron group metals or platinum group metals with iron, cobalt or nickel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Pyridine Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1051706D GB1051706A (enrdf_load_stackoverflow) | 1964-10-06 | ||
| DES93642A DE1276644B (de) | 1964-10-06 | 1964-10-06 | Verfahren zur Herstellung von Alkylpyridinen |
| DE19651620272 DE1620272A1 (de) | 1964-10-06 | 1965-05-10 | Verfahren zur Herstellung von Alkylpyridinen |
| US473221A US3433792A (en) | 1964-10-06 | 1965-07-19 | Alkylpyridine production |
| BE670493D BE670493A (enrdf_load_stackoverflow) | 1964-10-06 | 1965-10-04 | |
| FR33666A FR1449245A (fr) | 1964-10-06 | 1965-10-04 | Procédé de préparation d'une pyridine alcoylée |
| NL6512874A NL6512874A (enrdf_load_stackoverflow) | 1964-10-06 | 1965-10-05 | |
| DE19651620310 DE1620310A1 (de) | 1964-10-06 | 1965-10-06 | Verfahren zur Herstellung von alkylsubstituierten Pyridinen |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES93642A DE1276644B (de) | 1964-10-06 | 1964-10-06 | Verfahren zur Herstellung von Alkylpyridinen |
| DES0097026 | 1965-05-10 | ||
| US473188A US3412096A (en) | 1965-07-19 | 1965-07-19 | Alkylpyridine production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1276644B true DE1276644B (de) | 1968-09-05 |
Family
ID=27212904
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES93642A Pending DE1276644B (de) | 1964-10-06 | 1964-10-06 | Verfahren zur Herstellung von Alkylpyridinen |
| DE19651620272 Pending DE1620272A1 (de) | 1964-10-06 | 1965-05-10 | Verfahren zur Herstellung von Alkylpyridinen |
| DE19651620310 Pending DE1620310A1 (de) | 1964-10-06 | 1965-10-06 | Verfahren zur Herstellung von alkylsubstituierten Pyridinen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651620272 Pending DE1620272A1 (de) | 1964-10-06 | 1965-05-10 | Verfahren zur Herstellung von Alkylpyridinen |
| DE19651620310 Pending DE1620310A1 (de) | 1964-10-06 | 1965-10-06 | Verfahren zur Herstellung von alkylsubstituierten Pyridinen |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE670493A (enrdf_load_stackoverflow) |
| DE (3) | DE1276644B (enrdf_load_stackoverflow) |
| GB (1) | GB1051706A (enrdf_load_stackoverflow) |
| NL (1) | NL6512874A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2331636C1 (ru) * | 2006-12-29 | 2008-08-20 | Институт нефтехимии и катализа РАН | Способ получения 2-этил-3,5-диметилпиридина |
| RU2333908C1 (ru) * | 2007-04-16 | 2008-09-20 | Институт нефтехимии и катализа РАН | Способ получения 2-этил-3,5-диметилпиридина |
| RU2334739C1 (ru) * | 2007-04-16 | 2008-09-27 | Институт нефтехимии и катализа РАН | Способ получения 2,3,5-триалкилпиридинов |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1058058B (de) * | 1954-02-27 | 1959-05-27 | Basf Ag | Verfahren zur Herstellung von Alkylpyridinen |
-
0
- GB GB1051706D patent/GB1051706A/en active Active
-
1964
- 1964-10-06 DE DES93642A patent/DE1276644B/de active Pending
-
1965
- 1965-05-10 DE DE19651620272 patent/DE1620272A1/de active Pending
- 1965-10-04 BE BE670493D patent/BE670493A/nl unknown
- 1965-10-05 NL NL6512874A patent/NL6512874A/xx unknown
- 1965-10-06 DE DE19651620310 patent/DE1620310A1/de active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1058058B (de) * | 1954-02-27 | 1959-05-27 | Basf Ag | Verfahren zur Herstellung von Alkylpyridinen |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2331636C1 (ru) * | 2006-12-29 | 2008-08-20 | Институт нефтехимии и катализа РАН | Способ получения 2-этил-3,5-диметилпиридина |
| RU2333908C1 (ru) * | 2007-04-16 | 2008-09-20 | Институт нефтехимии и катализа РАН | Способ получения 2-этил-3,5-диметилпиридина |
| RU2334739C1 (ru) * | 2007-04-16 | 2008-09-27 | Институт нефтехимии и катализа РАН | Способ получения 2,3,5-триалкилпиридинов |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6512874A (enrdf_load_stackoverflow) | 1966-04-07 |
| DE1620310A1 (de) | 1970-02-19 |
| GB1051706A (enrdf_load_stackoverflow) | |
| BE670493A (enrdf_load_stackoverflow) | 1966-04-04 |
| DE1620272A1 (de) | 1970-10-22 |
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