DE819401C - Process for the preparation of bis-cyanoalkylanilines - Google Patents
Process for the preparation of bis-cyanoalkylanilinesInfo
- Publication number
- DE819401C DE819401C DEP52447A DEP0052447A DE819401C DE 819401 C DE819401 C DE 819401C DE P52447 A DEP52447 A DE P52447A DE P0052447 A DEP0052447 A DE P0052447A DE 819401 C DE819401 C DE 819401C
- Authority
- DE
- Germany
- Prior art keywords
- bis
- preparation
- cyanoalkylanilines
- acrylonitrile
- weight
- 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 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001448 anilines Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- -1 aliphatic amines Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Bis-cyanalkylanilinen Man hat schon a, ß-ungesättigte Nitrile mit Aminen kondensiert, wobei die aromatischen Amine wesentlich schwerer als die aliphatischen Amine mit den a, ß-ungesättigten Nitrilen, z.,B. Acrylnitril, reagieren. Während Anilin in Gegenwart von alkalischen oder sauren Mitteln Acrylnitril noch anlagert, reagiert z. B. Monomethylanilin mit Acrylnitril auch in Gegenwart sehr wirksamer Katalysatoren selbst bei r8o° nicht.Process for the preparation of bis-cyanoalkylanilines One already has a, ß-unsaturated nitriles condensed with amines, the aromatic amines being essential heavier than the aliphatic amines with the α, ß-unsaturated nitriles, e.g. Acrylonitrile, react. While aniline in the presence of alkaline or acidic Means acrylonitrile still attaches, z. B. monomethylaniline with acrylonitrile not even in the presence of very effective catalysts, even at r80 °.
Es wurde nun gefunden, daB man wertvolle Kondensationsprodukte erhalten kann, wenn .man N-Cyanmethvlaniline mit Acrylnitril in Gegenwart alkalisch wirkender -Mittel umsetzt. Die N-Cyanmethvlaniline sind leicht aus Anilin oder dessen Kernsubstitutionsprodukten, Blausäure und Formaldehyd, erhältlich. Als alkalisch wirkende Mittel kommen insbesondere die Alkalialkoholate in Betracht, doch kann man auch mit Alkalilaugen oder Aminen, wie Piperidin, Trimethylbenzylammoniumhydroxyd usw., arbeiten. Man nimmt zweckmäßig die Umsetzung in Gegenwart von Lösungsmitteln oder Verdünnungsmitteln vor.It has now been found that valuable condensation products are obtained can, if .man N-Cyanmethvlaniline with acrylonitrile in the presence of alkaline acting -Means implement. The N-Cyanmethvlaniline are easily made from aniline or its core substitution products, Hydrocyanic acid and formaldehyde, available. As alkaline agents come in particular the alkali alcoholates into consideration, but one can also use alkali lye or amines, such as piperidine, trimethylbenzylammonium hydroxide, etc., work. One takes appropriately the reaction in the presence of solvents or diluents before.
Die erhaltenen N-Cyanmethyl-N-cyanäthylaniline können als Zwischenprodukte für die Herstellung von Farbstoffen, Textilhilfsmitteln usw. Verwenc'.ung finden.The N-cyanomethyl-N-cyanoethylanilines obtained can be used as intermediates for the production of dyes, textile auxiliaries, etc. use.
Beispiel Man legt ein Gemisch aus 5o Gewichtsteilen Dioxan und r Gewichtsteil
festem Natriumäthylat vor
und trägt sodann bei 30° ein Gemisch aus
26 Gewichtsteilen N-Cyanmethylaniliii und .45 Gewichtsteilen Acrylnitril allmählich
ein, rührt nach beendetem Eintragen noch einige Zeit bei 30° nach, neutralisiert
mit Essigsäure und destilliert Dioxan und überschüssiges Acrylnitril ab. Der dunkelbraune,
dickflüssige Rückstand wird mit Benzol ausgekocht, wobei sich das Reaktionsprodukt
löst, während harzige Schmieren ungelöst bleiben. Man trennt die Benzollösung vom
Rückstand ab, destilliert das Benzol ab und erhält beim Kp2 mm 2o5° als hellgelbe
Kristalle N-Cyanmethyl-N-cyanäthylanilin vom Schmelzpunkt 52 bis 62°. Nach dem
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP52447A DE819401C (en) | 1949-08-20 | 1949-08-20 | Process for the preparation of bis-cyanoalkylanilines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP52447A DE819401C (en) | 1949-08-20 | 1949-08-20 | Process for the preparation of bis-cyanoalkylanilines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE819401C true DE819401C (en) | 1951-10-31 |
Family
ID=7385757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP52447A Expired DE819401C (en) | 1949-08-20 | 1949-08-20 | Process for the preparation of bis-cyanoalkylanilines |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE819401C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2809985A (en) * | 1956-04-10 | 1957-10-15 | Gen Aniline & Film Corp | Bis-cyanoethylated anilines |
-
1949
- 1949-08-20 DE DEP52447A patent/DE819401C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2809985A (en) * | 1956-04-10 | 1957-10-15 | Gen Aniline & Film Corp | Bis-cyanoethylated anilines |
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