CH622008A5 - Process for the catalytic preparation of beta-substituted 2-ethylpyridines - Google Patents

Process for the catalytic preparation of beta-substituted 2-ethylpyridines Download PDF

Info

Publication number: CH622008A5
Authority: CH; Switzerland
Prior art keywords: alcohols; amines; compounds; cobaltocene; reaction
Prior art date: 1976-10-15

Application number

CH1307976A

Other languages

German (de)

English (en)

Inventor

Peter Dr Dipl Chem Hardt

Original Assignee

Lonza Ag

Priority date (The priority date 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 date listed.)

1976-10-15

Filing date

1976-10-15

Publication date

1981-03-13

1976-04-08 Priority to DE2615309A priority Critical patent/DE2615309C2/de

1976-10-15 Application filed by Lonza Ag filed Critical Lonza Ag

1976-10-15 Priority to CH1307976A priority patent/CH622008A5/de

1977-09-21 Priority to DE19772742541 priority patent/DE2742541A1/de

1977-09-21 Priority to DE19772742542 priority patent/DE2742542A1/de

1977-10-14 Priority to BE181780A priority patent/BE859767R/fr

1977-10-17 Priority to US05/843,033 priority patent/US4196287A/en

1981-03-13 Publication of CH622008A5 publication Critical patent/CH622008A5/de

Links

-1 beta-substituted 2-ethylpyridines Chemical class 0.000 title claims description 15
238000000034 method Methods 0.000 title claims 13
230000003197 catalytic effect Effects 0.000 title claims 5
238000002360 preparation method Methods 0.000 title claims 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 13
ILZSSCVGGYJLOG-UHFFFAOYSA-N cobaltocene Chemical compound [Co+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 ILZSSCVGGYJLOG-UHFFFAOYSA-N 0.000 claims description 13
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 8
238000004821 distillation Methods 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 4
239000012043 crude product Substances 0.000 claims description 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
239000000047 product Substances 0.000 claims description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims 8
150000001412 amines Chemical class 0.000 claims 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
239000003054 catalyst Substances 0.000 claims 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 2
NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical class CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 claims 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
229910021529 ammonia Inorganic materials 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
230000001590 oxidative effect Effects 0.000 claims 2
150000003141 primary amines Chemical class 0.000 claims 2
150000005619 secondary aliphatic amines Chemical class 0.000 claims 2
150000003335 secondary amines Chemical class 0.000 claims 2
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
230000017525 heat dissipation Effects 0.000 claims 1
150000002440 hydroxy compounds Chemical class 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
MTPJEFOSTIKRSS-UHFFFAOYSA-N 3-(dimethylamino)propanenitrile Chemical compound CN(C)CCC#N MTPJEFOSTIKRSS-UHFFFAOYSA-N 0.000 description 3
OOWFYDWAMOKVSF-UHFFFAOYSA-N 3-methoxypropanenitrile Chemical compound COCCC#N OOWFYDWAMOKVSF-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
QRBVCAWHUSTDOT-UHFFFAOYSA-N Methyridine Chemical compound COCCC1=CC=CC=N1 QRBVCAWHUSTDOT-UHFFFAOYSA-N 0.000 description 2
AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000007701 flash-distillation Methods 0.000 description 2
PMDWLPBLYZHLHW-UHFFFAOYSA-N n,n-diethyl-2-pyridin-2-ylethanamine Chemical compound CCN(CC)CCC1=CC=CC=N1 PMDWLPBLYZHLHW-UHFFFAOYSA-N 0.000 description 2
FXHJGPDCPMCUKW-UHFFFAOYSA-N n,n-dimethyl-2-pyridin-2-ylethanamine Chemical compound CN(C)CCC1=CC=CC=N1 FXHJGPDCPMCUKW-UHFFFAOYSA-N 0.000 description 2
XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 description 1
LFFKXGFSDGRFQA-UHFFFAOYSA-N 3-(diethylamino)propanenitrile Chemical compound CCN(CC)CCC#N LFFKXGFSDGRFQA-UHFFFAOYSA-N 0.000 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000006837 decompression Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000002040 relaxant effect Effects 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
- C07D213/24—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 with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
- 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
- C07D213/24—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 with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)

CH1307976A 1975-09-18 1976-10-15 Process for the catalytic preparation of beta-substituted 2-ethylpyridines CH622008A5 (en)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
DE2615309A DE2615309C2 (de)	1975-09-18	1976-04-08	Verfahren zur katalytischen Herstellung von 2-substituierten Pyridinen
CH1307976A CH622008A5 (en)	1976-10-15	1976-10-15	Process for the catalytic preparation of beta-substituted 2-ethylpyridines
DE19772742541 DE2742541A1 (de)	1975-09-18	1977-09-21	Verfahren zur katalytischen herstellung von beta-substituierten 2-aethyl- pyridinen
DE19772742542 DE2742542A1 (de)	1975-09-18	1977-09-21	Verfahren zur herstellung von 2-n, n-disubstituierten aminopyridinen
BE181780A BE859767R (fr)	1976-10-15	1977-10-14	Procede de preparation catalytique de pyridines substituees en position 2
US05/843,033 US4196287A (en)	1975-09-18	1977-10-17	Process for the catalytic production of 2-substituted pyridines

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1307976A CH622008A5 (en)	1976-10-15	1976-10-15	Process for the catalytic preparation of beta-substituted 2-ethylpyridines

Publications (1)

Publication Number	Publication Date
CH622008A5 true CH622008A5 (en)	1981-03-13

Family

ID=4389104

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1307976A CH622008A5 (en)	1975-09-18	1976-10-15	Process for the catalytic preparation of beta-substituted 2-ethylpyridines

Country Status (2)

Country	Link
BE (1)	BE859767R (fr)
CH (1)	CH622008A5 (fr)

1976
- 1976-10-15 CH CH1307976A patent/CH622008A5/de not_active IP Right Cessation
1977
- 1977-10-14 BE BE181780A patent/BE859767R/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE859767R (fr)	1978-04-14

Legal Events

Date	Code	Title	Description
1989-06-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE3235933A1 (de)	1984-03-29	Verfahren zur herstellung bicyclischer orthoesteramide
DE69206250T2 (de)	1996-05-02	Verfahren zur herstellung von nitrilen.
EP0352504B1 (fr)	1992-09-16	Procédé pour la préparation simultanée de 3-dialkylaminopropionitriles, de bis-(2-cyanoéthyl)-éther et, le cas échéant, de la cyanhydrine d'éthylène
DE1200281B (de)	1965-09-09	Verfahren zur Herstellung von Acetessigsaeureestern
DE69513869T2 (de)	2000-06-29	Verfahren zur Wiedergewinnung von Propylenoxid
DE69417308T2 (de)	1999-08-26	Decarboxylierungsverfahren
DE2540972C3 (de)	1979-03-22	Verfahren zur Herstellung von 5-Oxohexansäure und deren Derivaten
DE2615309C2 (de)	1987-02-12	Verfahren zur katalytischen Herstellung von 2-substituierten Pyridinen
DE2443142C2 (de)	1985-10-03	Verfahren zur Herstellung von Cyclopropancarbonsäurenitril
DE2804115C2 (fr)	1988-03-10
DE2742541A1 (de)	1978-04-20	Verfahren zur katalytischen herstellung von beta-substituierten 2-aethyl- pyridinen
EP0171046B1 (fr)	1988-11-09	Procédé de préparation de la pantolactone
DE2729974B2 (de)	1980-12-11	Verfahren zur Herstellung von wäßrigen Lösungen bzw. feinteiligen wäßrigen Dispersionen von Polyenyltriarylphosphoniumsalzen
DE958840C (de)	1957-02-28	Verfahren zur Herstellung von Cyclohexanonoxim aus Cyclohexan
EP0013254B1 (fr)	1982-08-04	Procédé de préparation des acides oxo-5-hexanoiques, de leurs esters et de leurs nitriles
EP0292674A2 (fr)	1988-11-30	Procédé de préparation du propinol
DE912810C (de)	1954-06-03	Verfahren zur Herstellung von monomeren Vinylestern
DE2121635C3 (fr)	1974-11-14
EP0132681A1 (fr)	1985-02-13	Procédé pour la préparation d'acides fluorocarboxyliques
EP0097244A1 (fr)	1984-01-04	Méthode de préparation de cyanacétaldéhyde-acétals
CH633278A5 (de)	1982-11-30	Verfahren zur herstellung von 2-alkyl- bzw. 2-cycloalkyl-4-methyl-6-hydroxypyrimidinen.
AT255399B (de)	1967-07-10	Verfahren zur Herstellung von substituierten oder unsubstituierten Adipinsäuren
DE1913123C (de)	1971-07-29	Verfahren zur Herstellung eines Gemisches aus einem aromatischen Aldehyd und einem aromatischen Alkohol mit über wiegendem Aldehydanteil
AT256066B (de)	1967-08-10	Verfahren zur Herstellung von 6-Formyloxycapronsäuren und gegebenenfalls ɛ-Caprolactonen
DE1668853C3 (de)	1975-10-16	Verfahren zur Herstellung von Acetamiden