CH128902A - Process for the preparation of ar-tetrahydro-B-naphthylamine. - Google Patents
Process for the preparation of ar-tetrahydro-B-naphthylamine.Info
- Publication number
- CH128902A CH128902A CH128902TA CH128902A CH 128902 A CH128902 A CH 128902A CH 128902T A CH128902T A CH 128902TA CH 128902 A CH128902 A CH 128902A
- Authority
- CH
- Switzerland
- Prior art keywords
- tetrahydro
- naphthylamine
- preparation
- hydrogen
- metal
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 150000005840 aryl radicals Chemical group 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- -1 acyl radical Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von ar-Tetrahydro-ss-naphtylamin. Die bisher bekannten Verfahren zur Her stellung hydrierter aromatischer Aminover- bindungen geben keine befriedigenden Resul tate. Die von Jpatiew (siehe Bericht der Deutschen Chemischen Gesellschaft, Band 41, Seite 991) beschriebene Hydrierung von pri mären aromatischen Aminen mittelst Wasser stoff und Katalysatoren unter Druck erfolgt nur sehr langsam unter Bildung unerwünsch ter Nebenprodukte.
Auch das Verfahren von Sabatier und Senderens, die sekundäre und tertiäre Amine in Gegenwart von fein ver teiltem Nickel in gasförmigem Zustande re- cluzierten, blieb bezüglich Ausbeute und Reinheit der erhaltenen Produkte unbefrie digend (vergleiche Compt. rend., Band 188, Seite 457).
Es wurde nun gefunden, dass aromatische Aminoverbindungen der allgemeinen Formel:
EMI0001.0016
worin R einen Arylrest der Benzol- oder Naphthalinreihe, X, Wasserstoff oder einen Alkyl-, Aralkyl- oder Arylrest, X, einen Alkyl-, Aralkyl- oder Arylrest odar einen Acylrest bedeutet, in Gegenwart von metallhaltigen Katalysatoren unter Wasser stoffdruck Wasserstoff aufnehmen und hier bei in guter Ausbeute und Reinheit hydrierte Produkte bilden.
Bei Verwendung von Al kyl, Aralkyl- oder Arylderivaten werden die gewünschten hydrierten Basen unmittelbar erhalten, bei Verwendung von Acylderivaten kann zwecks Bildung der freien hydrierten Basen die Acylgruppe durch Verseifung ab gespalten werden.
Als Katalysatoren können die verschie denartigsten metallhaltigen Reduktionskata lysatoren Verwendung finden, solche, die Nickel, Kobalt oder Kupfer oder Gemische davon enthalten, haben sich als besonders wirksam erwiesen. Die erhaltenen Produkte sind teilweise neu und sollen zur Herstellung von Farb stoffen, pharmazeutischen und andern wert vollen technischen Produkten Verwendung finden.
Vorliegendes Patent bezieht sich nun auf die Darstellung von a.r-Tetrahydro-ss-naphtyl- amin der Formel
EMI0002.0003
durch Behandeln von Acet-ss-naphtylainin mit Wasserstoff bei Gegenwart eines me tallhaltigen Katalysators unter Wasserstoff druck und Abspalten der Acetylgruppe aus dem so erhaltenen Acetyl-a.r-tetrahydro-ss- naphthylamin mittelst verseifenden Mitteln.
Das ar-Tetrahydro-ss-naphtylamin siedet unter normalem Druck bei<B>271</B> bis<B>273'.</B> Beispiel <I>2:</I> 50 Teile reines Acet-ss-naphtylamin wer den im Autoklaven mit 200 Teilen Dekalin unter Zusatz eines geeigneten nickelhaltigen Katalysators unter einem Wasserstoffdruck von etwa 20 Atmosphären auf 200 bis '-)-90' erhitzt. Nach Aufnahme von 2 Molekülen Wasserstoff wird filtriert.
Nachdem das Deka.lin mit Wasserdampf übergetrieben ist, kann aus dem Rückstand das Acetyl-ar-tetra- hydro-ss-naphtyla.min mit Ä4-her ausgeschüt telt werden. Nach dem Abdampfen des 4thers hinterbleibt es als ein in der Kälte erstarrendes <B>01.</B> Durch Verseifen mit Salz säure lässt sich daraus das ar-Tetrahydro-ss- naplityla.min gewinnen.
Process for the preparation of ar-tetrahydro-ss-naphthylamine. The previously known processes for the preparation of hydrogenated aromatic amino compounds do not give satisfactory results. The hydrogenation of primary aromatic amines by means of hydrogen and catalysts under pressure described by Jpatiew (see report of the German Chemical Society, Volume 41, page 991) takes place only very slowly with the formation of undesired by-products.
The process of Sabatier and Senderens, which reduced secondary and tertiary amines in the presence of finely divided nickel in the gaseous state, remained unsatisfactory with regard to the yield and purity of the products obtained (see Compt. Rend., Volume 188, page 457). .
It has now been found that aromatic amino compounds of the general formula:
EMI0001.0016
where R is an aryl radical of the benzene or naphthalene series, X, hydrogen or an alkyl, aralkyl or aryl radical, X, an alkyl, aralkyl or aryl radical or an acyl radical, taking up hydrogen under hydrogen pressure in the presence of metal-containing catalysts and here form hydrogenated products in good yield and purity.
When using alkyl, aralkyl or aryl derivatives, the desired hydrogenated bases are obtained immediately; when using acyl derivatives, the acyl group can be cleaved off by saponification in order to form the free hydrogenated bases.
The most varied of metal-containing reduction catalysts can be used as catalysts; those containing nickel, cobalt or copper or mixtures thereof have proven to be particularly effective. Some of the products obtained are new and are intended to be used in the manufacture of dyes, pharmaceuticals and other valuable technical products.
The present patent now relates to the preparation of a.r-tetrahydro-ss-naphthylamine of the formula
EMI0002.0003
by treating acet-ß-naphtylainin with hydrogen in the presence of a metal-containing catalyst under hydrogen pressure and splitting off the acetyl group from the acetyl-a.r-tetrahydro-s-naphthylamine by means of saponifying agents.
The ar-tetrahydro-ss-naphtylamine boils under normal pressure at <B> 271 </B> to <B> 273 '. </B> Example <I> 2 </I> 50 parts of pure acet-ss-naphtylamine who heated the in the autoclave with 200 parts of decalin with the addition of a suitable nickel-containing catalyst under a hydrogen pressure of about 20 atmospheres to 200 to '-) - 90'. After absorbing 2 molecules of hydrogen, it is filtered.
After the Deka.lin has been blown over with water vapor, the acetyl-ar-tetra-hydro-ss-naphtyla.min can be shaken out from the residue with a 4-ring method. After the 4thers has evaporated, it remains as a <B> 01. </B> that solidifies in the cold. The ar-tetrahydro-ss- naplityla.min can be obtained from it by saponification with hydrochloric acid.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH128902T CH128902A (en) | 1927-04-28 | 1927-04-28 | Process for the preparation of ar-tetrahydro-B-naphthylamine. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH128902T CH128902A (en) | 1927-04-28 | 1927-04-28 | Process for the preparation of ar-tetrahydro-B-naphthylamine. |
| CH127524T | 1927-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH128902A true CH128902A (en) | 1928-11-16 |
Family
ID=25710894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH128902T CH128902A (en) | 1927-04-28 | 1927-04-28 | Process for the preparation of ar-tetrahydro-B-naphthylamine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH128902A (en) |
-
1927
- 1927-04-28 CH CH128902T patent/CH128902A/en unknown
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