DEK0025088MA - - Google Patents
Info
- Publication number
- DEK0025088MA DEK0025088MA DEK0025088MA DE K0025088M A DEK0025088M A DE K0025088MA DE K0025088M A DEK0025088M A DE K0025088MA
- Authority
- DE
- Germany
- Prior art keywords
- hydrogenation
- nitriles
- aldehydes
- dianilinoethane
- water
- 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.)
- Active
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- 150000002825 nitriles Chemical class 0.000 claims description 4
- AZINJOAUEDYASP-UHFFFAOYSA-N 1-N,1-N'-diphenylethane-1,1-diamine Chemical compound C=1C=CC=CC=1NC(C)NC1=CC=CC=C1 AZINJOAUEDYASP-UHFFFAOYSA-N 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- WYEYGPJVIZYKNM-UHFFFAOYSA-N 1,3-diphenylimidazolidine Chemical class C1CN(C=2C=CC=CC=2)CN1C1=CC=CC=C1 WYEYGPJVIZYKNM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 230000000737 periodic Effects 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DUIOPKIIICUYRZ-UHFFFAOYSA-N Semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- FTZQFBUICLZGLZ-UHFFFAOYSA-N 1,3-diphenyl-2-propylimidazolidine Chemical compound CCCC1N(C=2C=CC=CC=2)CCN1C1=CC=CC=C1 FTZQFBUICLZGLZ-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 1-butanal Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N Butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000003301 hydrolyzing Effects 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Description
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
Tag der Anmeldung: 5. März 1955 Bekanntgemacht am 15. November 1956Registration date: March 5, 1955. Advertised on November 15, 1956
DEUTSCHES PATENTAMTGERMAN PATENT OFFICE
PATENTANMELDUNGPATENT APPLICATION
KLASSE 12ο GRUPPE 7o3 INTERNAT. KLASSE C 07c; dCLASS 12ο GROUP 7o3 INTERNAT. CLASS C 07c; d
K 25088 IVb/12 οK 25088 IVb / 12 ο
Dr. Hans Plieninger, HeidelbergDr. Hans Plieninger, Heidelberg
ist als Erfinder genannt wordenhas been named as the inventor
Knoll Aktiengesellschaft, Chemische Fabriken, Ludwigshafen/Rhein, Knollstr. 50Knoll Aktiengesellschaft, chemical factories, Ludwigshafen / Rhein, Knollstr. 50
Verfahren zur Herstellung von gesättigten Aldehyden aus NitrilenProcess for the preparation of saturated aldehydes from nitriles
Nach einem älteren Vorschlag besteht ein Verfahren zur Herstellung von Aldehyden aus Nitrilen durch katalytische Hydrierung darin, daß man die Hydrierung in Gegenwart von Metallen der VIII. Gruppe des Periodisoben Systems und von Semicarbazid durchführt und das erhaltene Semicarbazon in- an sich bekannter Weise spaltet.According to an older proposal, there is a process for the preparation of aldehydes from nitriles by catalytic hydrogenation in that the hydrogenation in the presence of metals VIII. Group of the Periodisobic System and of Semicarbazide and the resulting semicarbazone splits in a manner known per se.
Es wurde nun weiterhin gefunden, daß es besonders vorteilhaft ist, die katalytische Hydrierung der Nitrilei, anstatt in Gegenwart von Semicarbazid, in Gegenwart von Dianilinoäthan, C6H5 · NH-CH2-CH2-NH-C6H5, durchzuführen, wobei die besonders leicht zu den entsprechendenAldehyden spaltbaren. DiphenyltetrahydromidazoleIt has now also been found that it is particularly advantageous to carry out the catalytic hydrogenation of nitriles, instead of in the presence of semicarbazide, in the presence of dianilinoethane, C 6 H 5 .NH — CH 2 —CH 2 —NH — C 6 H 5 , whereby the particularly easily cleavable to the corresponding aldehydes. Diphenyl tetrahydromidazoles
CH2^-CH2 CH 2 ^ -CH 2
C6H5-N^ ^N-C6H6 CHC 6 H 5 -N ^ ^ NC 6 H 6 CH
als Zwischenprodukte erhalten werden.are obtained as intermediates.
«9 707/350«9 707/350
K 25088 IVb/12 οK 25088 IVb / 12 ο
Bei dieser Reaktion bleibt die Hydrierung bei dengebildeten Diphenyltetrahydroimidazolen stehen, die zum Unterschied von den Sernicarbazonen den Charakter von gesättigten Verbindungen besitzen. .Diese Zwischenverbindungen sind in Wasser schwer löslich, und, eignen sich daher auch, zur Darstellung von in Wasser leicht löslichen Aldehyden.In this reaction, the hydrogenation stops with the formed diphenyltetrahydroimidazoles, which, in contrast to the sernicarbazones, have the character of saturated compounds. These intermediate compounds are sparingly soluble in water and are therefore also suitable for representation of aldehydes which are readily soluble in water.
69 g Butyronitril werden mit einer Mischung aus 20 ecm Eisessig, 220 g Dianilinoäthan, 300 ecm
Methanol, 300 ecm Wasser und 20 g Raneynickel unter einem Wasserstoffdruck von 70 atü geschüttelt.
Nach Beendigung der Wasserstoffaufnahme wird vom Katalysator abnitriert, der Alkohol aus
dein Filtrat abgedampft:, und das Gemaseh mit.
Wasser versetzt,'worauf das I-Propyl72, ^d
tetrahydroimidazol auskristallisiert; F. 820 (aus Methanol), Ausbeute: 60% der Theorie.69 g of butyronitrile are shaken with a mixture of 20 ecm glacial acetic acid, 220 g dianilinoethane, 300 ecm methanol, 300 ecm water and 20 g Raney nickel under a hydrogen pressure of 70 atmospheres. After the uptake of hydrogen has ceased, the catalyst is removed by nitration, the alcohol is evaporated from the filtrate: and the mixture with it. Water is added, whereupon the I-propyl72, ^ d
tetrahydroimidazole crystallized out; F. 82 0 (from methanol), yield: 60% of theory.
Durch Spaltung des Propyldiphenyltetrahydroimidazols mit hydrolysierenden Mitteln erhält man in bekannter Weise den gesuchten Butyraldehyd.Cleavage of the propyldiphenyltetrahydroimidazole with hydrolyzing agents gives the butyraldehyde sought in a known manner.
Claims (1)
Family
ID=
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