DE305347C - - Google Patents
Info
- Publication number
- DE305347C DE305347C DENDAT305347D DE305347DA DE305347C DE 305347 C DE305347 C DE 305347C DE NDAT305347 D DENDAT305347 D DE NDAT305347D DE 305347D A DE305347D A DE 305347DA DE 305347 C DE305347 C DE 305347C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- naphthylamine
- solvent naphtha
- alcohol
- 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
Links
- 235000019441 ethanol Nutrition 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 230000001476 alcoholic Effects 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- 238000004508 fractional distillation Methods 0.000 claims 2
- 239000000446 fuel Substances 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 2
- JZICUKPOZUKZLL-UHFFFAOYSA-N 2-methyl-1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2NC(C)CCC2=C1 JZICUKPOZUKZLL-UHFFFAOYSA-N 0.000 claims 1
- YJKJAYFKPIUBAW-UHFFFAOYSA-N 9H-carbazol-1-amine Chemical compound N1C2=CC=CC=C2C2=C1C(N)=CC=C2 YJKJAYFKPIUBAW-UHFFFAOYSA-N 0.000 claims 1
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 1
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N Quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 229940075930 picrate Drugs 0.000 claims 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 claims 1
- MIMJFNVDBPUTPB-UHFFFAOYSA-N potassium hexacyanoferrate(3-) Chemical compound [K+].[K+].[K+].N#C[Fe-3](C#N)(C#N)(C#N)(C#N)C#N MIMJFNVDBPUTPB-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- -1 α-naphthylamine dihydro-α-naphthylamine Chemical compound 0.000 claims 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 2
- JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Die Hydrierung von aromatischen Aminen mittels Alkalimetalle konnte bisher mit befriedigender Ausbeute nur unter Anwendung von höher siedenden Alkoholen ausgeführt werden. Erforderlich war dafür aber auchThe hydrogenation of aromatic amines by means of alkali metals has so far been more satisfactory Yield can only be carried out using higher boiling alcohols. But that was also necessary
- noch ein möglichst stürmischer Verlauf der Reaktion, eine Bedingung, die für die fabrikatorische Anwendung dieses Verfahrens nicht ohne Bedenken ist.- the reaction should proceed as stormily as possible, a condition that applies to the manufacturing process Applying this procedure is not without concern.
ίο So z.B.schreibt Bamberger, Ber.2i(i888), Seite 852, über die Hydrierung von a- und β - Naphtylamin zu Tetrahydronaphtylamin: »Ändert man die Methode der Darstellung wesentlich ab, indem man z. B. den Amylalkohol durch Äthylalkohol ersetzt, oder indem man das Natrium allmählich zur Wirkung bringt, so verringert sich die Ausbaute in ersterem Falle sogar erheblich.« Ferner Ber. 21 (1888), Seite 1124 giDt er an, »daß der Amyl-ίο For example, writes Bamberger, Ber.2i (i888), page 852, about the hydrogenation of a- and β-naphthylamine to tetrahydronaphthylamine: »If the method of representation is changed significantly by e.g. If, for example, the amyl alcohol is replaced by ethyl alcohol, or if the sodium is gradually brought into effect, the expansion in the first case is even considerably reduced. ”Further Ber. 21 (1888), page 1124 , does he state that “the amyl
alkohol dem Äthylalkohol, wenn es sich um den Zweck einer guten Ausbeute handelt, infolge der . höheren Reaktionstemperätur weit überlegen ist«; ferner »daß auch die Methode des raschen Hinzugebens der Flüssigkeit (kochende alkoholische Basenlösung) zum Natrium der anderen vorzuziehen ist«. Noch bestimmter urteilt Bamberger in Ber. 20, Seite 2916, Fußnote: »Wendet man dabei Äthylalkohol (an Stelle von Amylalkohol) an, so sinkt die Ausbeute auf ein Minimum herab, und der weitaus größte Teil des angewandten Naphtylamins geht unverändert aus dem Reaktionsprozeß hervor.«alcohol to ethyl alcohol, if it is a question of a good yield, as a result the . is far superior to higher reaction temperatures «; furthermore »that also the method the rapid addition of the liquid (boiling alcoholic base solution) to the sodium is preferable to the other «. Yet Bamberger judges more precisely in Ber. 20, page 2916, footnote: »If you use ethyl alcohol (instead of amyl alcohol), the yield drops to a minimum, and the vast majority of that used Naphthylamine leaves the reaction process unchanged emerge. "
Es wurde nun gefunden, daß man bei sehr ruhigem Verlauf der Reaktion eine gute Hydrierung von aromatischen Basen erzielen kann, wenn'man zu einem Gemisch von Alkali- oder Erdalkalimetall, einem passend gewählten indifferenten Lösungsmittel und der Base' Alkohol oder , eine alkoholische Lösung der Base bei einer für die gewünschte Hydrierungsstufe erforderlichen Temperatur allmählich zufließen läßt. Dieses läßt sich bei Anwendung von Alkoholen der verschiedensten Siedepunkte leicht erreichen, wenn man den Alkohol ungefähr in dem Tempo zufließen läßt, wie er durch die Reaktion als Alkoholat gebunden wird, oder wenn man bei schnellerer Zugabe von Alkohol den Überschuß, nötigenfalls unter Einhaltung von 5<> Überdruck, während der Reaktion abdestillieren läßt.It has now been found that if the reaction proceeds very smoothly, a good one can be obtained Hydrogenation of aromatic bases can be achieved if a mixture of alkali or alkaline earth metal, an appropriately selected inert solvent and the Base 'alcohol or, an alcoholic solution of the base at one for the desired Hydrogenation stage required temperature can gradually flow. This can easily reach when using alcohols of various boiling points, if the alcohol is allowed to flow in at approximately the same rate as it is due to the reaction Alcoholate is bound, or if, with faster addition of alcohol, the excess, If necessary, distill off during the reaction while maintaining 5 <> excess pressure leaves.
Dieses Verfahren hat gegenüber den von Bamberger und anderen Autoren beschriebenen Verfahren noch den großen Vorzug, daß bei der Fabrikation der teure und gesundheitsschädliche Amylalkohol z. B. durch den harmlosen und billigen Äthylalkohol vollkommen ersetzt werden kann. Außerdem zeichnet sich das Verfahren durch eine große Betriebssicherheit und Regulierbarkeit aus, weil z. B. einerseits die leicht entzündbaren AlkalimetalleThis procedure has opposite to that described by Bamberger and other authors Process still has the great advantage that in the manufacture of the expensive and harmful to health Amyl alcohol e.g. B. can be completely replaced by the harmless and cheap ethyl alcohol. Also draws the process is characterized by a high level of operational reliability and controllability, because z. B. on the one hand the highly flammable alkali metals
Claims (1)
Publications (1)
Publication Number | Publication Date |
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DE305347C true DE305347C (en) |
Family
ID=558868
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DENDAT305347D Active DE305347C (en) |
Country Status (1)
Country | Link |
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DE (1) | DE305347C (en) |
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0
- DE DENDAT305347D patent/DE305347C/de active Active
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