DE963329C - Process for the production of saturated aldehydes from nitriles - Google Patents
Process for the production of saturated aldehydes from nitrilesInfo
- Publication number
- DE963329C DE963329C DEK25088A DEK0025088A DE963329C DE 963329 C DE963329 C DE 963329C DE K25088 A DEK25088 A DE K25088A DE K0025088 A DEK0025088 A DE K0025088A DE 963329 C DE963329 C DE 963329C
- Authority
- DE
- Germany
- Prior art keywords
- nitriles
- production
- saturated aldehydes
- aldehydes
- hydrogenation
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000002825 nitriles Chemical class 0.000 title claims description 4
- 229920006395 saturated elastomer Polymers 0.000 title claims description 4
- 150000001299 aldehydes Chemical class 0.000 title 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
- 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
- 230000000737 periodic effect Effects 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- -1 aldehydes Nitriles Chemical class 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
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 2
- 150000007659 semicarbazones Chemical class 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
- WYEYGPJVIZYKNM-UHFFFAOYSA-N 1,3-diphenylimidazolidine Chemical class C1CN(C=2C=CC=CC=2)CN1C1=CC=CC=C1 WYEYGPJVIZYKNM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Herstellung von gesättigten Aldehyden aus Nitrilen 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 Periodischen Systems und von Semicarbazid durchführt und das erhaltene Semicarbazon in an sich bekannter Weise spaltet.Process for the preparation of saturated aldehydes from nitriles To an older proposal consists of a process for the preparation of aldehydes Nitriles by catalytic hydrogenation in that the hydrogenation is carried out in the presence of metals of Group VIII of the Periodic Table and of semicarbazide and the semicarbazone obtained cleaves in a manner known per se.
Es wurde nun weiterhin gefunden, daß es besonders vorteilhaft ist, die katalytische Hydrierung der Nitrile, anstatt in Gegenwart von Semicarbazid, in Gegenwart von Dianilinoäthan, CH5 NH # CH2 # CH2 # NH # C6 H5, durchzuführen, wobei die besonders leicht zu den entsprechendenAldehyden spaltbaren D iphenyltetraäydromidazole als Zwischenprodukte erhalten werden.It has now also been found that it is particularly advantageous to carry out the catalytic hydrogenation of the nitriles, instead of in the presence of semicarbazide, in the presence of dianilinoethane, CH5 NH # CH2 # CH2 # NH # C6 H5, which is particularly easy to give the corresponding aldehydes cleavable diphenyltetraydromidazoles are obtained as intermediates.
Bei dieser Reaktion bleibt die Hydrierung bei den gebildeten Diphenyltetrahydroimidazolen stehen, die zum Unterschied von den Semicarbazonen den Charakter von gesättigten Verbindungen besitzen. In this reaction, the hydrogenation remains with the diphenyltetrahydroimidazoles formed which, in contrast to the semicarbazones, have the character of saturated Own connections.
Diese Zwischenverbindungen sind in Wasser schwer löslich und eignen sich daher auch zur Darstellung von in Wasser leicht löslichen Aldehyden. These intermediate compounds are sparingly soluble in water and are suitable therefore also suitable for the preparation of aldehydes which are readily soluble in water.
Beispiel 69 g Butyronitril werden mit einer Mischung aus 20 ccm Eisessig, 220 g Dianilinoäthan, 300 ccm Methanol, 300 ccm Wasser -und 20 g Raneynid<el unter einem Wasserstoffdruck von 70 atü geschüttelt. Nach Beendigung der Wasserstoffaufnahme wird vom Katalysator abfiltriert, der Alkohol aus dem Filtrat abgedampft und das Gemisch mit Wasser versetzt, worauf das 1-Propyl-2,4-diphenyltetrahydroimidazol auskristallisiert: F. 82° faus Methanol), Ausbeute: 60% der Theorie. Example 69 g of butyronitrile are mixed with a mixture of 20 ccm of glacial acetic acid, 220 g of dianilinoethane, 300 ccm of methanol, 300 ccm of water and 20 g of Raneynide <el shaken under a hydrogen pressure of 70 atmospheres. After the hydrogen uptake has ceased the catalyst is filtered off, the alcohol is evaporated from the filtrate and the Mixture mixed with water, whereupon the 1-propyl-2,4-diphenyltetrahydroimidazole crystallized out: mp 82 ° from methanol), yield: 60% of theory.
Durch Spaltung des Propyldiphenyltetrahydroimidazol mit hydrolysierenden Mitteln erhält man in bekannter Weise den gesuchten Butyraldehyd. By cleavage of the propyldiphenyltetrahydroimidazole with hydrolyzing The sought-after butyraldehyde is obtained in a known manner.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK25088A DE963329C (en) | 1955-03-06 | 1955-03-06 | Process for the production of saturated aldehydes from nitriles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK25088A DE963329C (en) | 1955-03-06 | 1955-03-06 | Process for the production of saturated aldehydes from nitriles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE963329C true DE963329C (en) | 1957-05-09 |
Family
ID=7217209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK25088A Expired DE963329C (en) | 1955-03-06 | 1955-03-06 | Process for the production of saturated aldehydes from nitriles |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE963329C (en) |
-
1955
- 1955-03-06 DE DEK25088A patent/DE963329C/en not_active Expired
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