DEP0052447DA - Process for the preparation of bis-cyanoalkylanilines - Google Patents
Process for the preparation of bis-cyanoalkylanilinesInfo
- Publication number
- DEP0052447DA DEP0052447DA DEP0052447DA DE P0052447D A DEP0052447D A DE P0052447DA DE P0052447D A DEP0052447D A DE P0052447DA
- Authority
- DE
- Germany
- Prior art keywords
- thy
- lani
- cyanine
- acrylonitrile
- melting point
- 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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 238000002844 melting Methods 0.000 claims 2
- 230000008018 melting Effects 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- -1 aliphatic amines Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 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
- 239000007859 condensation product Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000203 mixture Substances 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
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Description
CHEMISCHE WERKE HÜLS &*m»b«üe Harl, den 17*8*1949CHEMISCHE WERKE HÜLS & * m »b« ü e Harl, 17 * 8 * 1949
- Patentbüro - EraRecklinghausen- Patent Office - EraRecklinghausen
Unser Zeichen Our sign t t 0«,Z» 3870 ", Z" 387
Verfahren zur Herstellung Method of manufacture
lan hat schon ^fρ -ungesättigte Nitrile ?jit Aminen kondensiert* wobei die aromatischen Amine wesentlich schwerer als die aliphatischen Amine mit den d> ,/3 »ungesättigten Nitrilen, z«Ba Acrylnitril, reagieren» Während Anilin in Gegenwart von alkalischen sauren Mitteln Acrylnitril noch anlagert» reagiert ζ J3« Mo-lan has already condensed ^ f ρ -unsaturated nitriles? jit amines * whereby the aromatic amines react much more heavily than the aliphatic amines with the d>, / 3 "unsaturated nitriles, z" Ba acrylonitrile, "while aniline reacts in the presence of alkaline acidic agents Acrylonitrile still accumulates »reacts ζ J3« mo-
nomethylanilin sii"b Acrylnitril auch in Gegenwart sehr wirksamer Katalysatoren selbst bei 180° nicht«,nomethylaniline sii "b acrylonitrile not even in the presence of very effective catalysts even at 180 °",
Es wurde nun gefunden, dass man wertvolle Eondensationsprodukte erhalten kann, wenn man H-Cyanmethyl-aniline mit Acrylnitril in Gegenwart alkalisch wirkender Mittel umsetzt« Die /V -Cyanmethylaniline sind leicht aus Anilin oder dessen Kernsubstitutionsprodukten, Blausäure und Formaldehyd erhältlich.«. Als alkalisch wirkende Mittel kommen insbesondere die Alkalialkoholate in Betrachtf 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 can be obtained if H-cyanomethyl-aniline is mixed with acrylonitrile The presence of alkaline agents reacts «The / V -cyanomethylanilines are easily derived from aniline or its core substitution products, Hydrocyanic acid and formaldehyde available. «. Alkali alcoholates are particularly suitable as alkaline agents but one can also work with alkaline solutions or amines, such as piperidine, trimethylbenzylammonium hydroxide, etc. the implementation in the presence of solvents or diluents before «
Die erhaltenen A/-Cyamethyl~/V-oyanäthylaniline können als Zwischenprodukte für die Herstellung von Farbstoffen, Textilhilfs» mitteln usw« Verwendung finden«The obtained A / -Cyamethyl ~ / V-oyanäthylaniline can be used as intermediate products for the production of dyes, textile auxiliaries » means etc. «find use«
lan legt ein Gemisch aus 50 Gewichtsteilen Dioxan und 1 Gewichtsteil festem Hatriumäthylat vor und trägt sodann bei 30° ein Ge» misch aus 26 Gewichtsteilen A/-Cyanmethy 1 anilin 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 unge-lan presents a mixture of 50 parts by weight of dioxane and 1 part by weight of solid sodium ethylate and then carries a weight at 30 ° Mixing 26 parts by weight of A / -Cyanmethy 1 aniline and 45 parts by weight of acrylonitrile gradually, stirs when the end of the introduction for some time at 30 °, neutralized with acetic acid and distilled off dioxane and excess acrylonitrile # The dark brown, viscous residue is boiled with benzene, whereby the reaction product dissolves, while resinous smear un-
Claims (1)
Family
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