CH145308A - Process for the preparation of a derivative of cyclohexylbenzene. - Google Patents
Process for the preparation of a derivative of cyclohexylbenzene.Info
- Publication number
- CH145308A CH145308A CH145308DA CH145308A CH 145308 A CH145308 A CH 145308A CH 145308D A CH145308D A CH 145308DA CH 145308 A CH145308 A CH 145308A
- Authority
- CH
- Switzerland
- Prior art keywords
- methoxy
- amino
- preparation
- hexahydrodiphenyl
- derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical class [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000003502 gasoline Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Abkömmlings des Cykloliexylbenzols. Vorliegendes Patent bezieht sich auf ein Verfahren zur Darstellung von 4-Amino-3- methoxy-hexahydrodiphenyl, dadurch ge kennzeichnet, dass man 4.4'-Diamino=3.3'- dimethoxy-diphenyl-cyklohexan durch Er hitzen auf höhere Temperatur in 4-Amino-3- methoxy-tetrahydrodiphenyl überführt und dieses mit Wasserstoff in Gegenwart eines Schwermetallkatalysators unter Druck be handelt.
Die Reaktion wird zweckmässig in einem Arbeitsgang ohne Abscheidung des Tetrahydrodiphenylderivates ' durchgeführt.
Das so erhaltene noch nicht beschriebene 4-Amino-3-methoxy-hexahydrodiphenyl kri- stallisiert Toluol oder Benzin in Form breiter, glänzender farbloser Schuppen vom Schmelzpunkt 107 .
Das Produkt soll als Zwischenprodukt zur Herstellung von Farbstoffen und von pharmazeutischen Produkten Verwendung finden. <I>Beispiel:</I> 4. 4'-Diamino - 3 . 3' - dimethoxy-diphenyl- cyklohexan, wie es nach dem Verfahren des Schweizer Patentes Nr.<B>138194</B> erhalten wird, wird durch Destillation im Vakuum in zwei Fraktionen zerlegt. Die Fraktion, die unter einem Druck von 12 mm bei 180-220 über geht, wird über das schwer lösliche salzsaure Salz gereinigt.
57 kg des so erhaltenen 4-Amino-3-me- thoxy-tetrahydro-diphenyl werden mit .1(1 kg 'Dekahydronaphthalin und 2,5 kg eines zuvor reduzierten Hydrierungskatalysators im Rührautoklaven bei 50-80 Atmosphären Wasserstoff erhitzt.
Die Aufnahme der auf 1 Mol. berechneten Menge vollzieht sich rasch bei<B>80-100'.</B> Bei der Aufarbeitung erhält man das bisher noch nicht beschrie bene 4-Amino-3-methoxy-hexahydrodiphenyl: Zum gleichen Produkt gelangt man, wenn man 4. 4'-Diamino - 3 . 3'-dimethoxy - cylklo- hexan unmittelbar mit Wasserstoff behan delt.
Process for the preparation of a derivative of cycloliexylbenzene. The present patent relates to a process for the preparation of 4-amino-3-methoxy-hexahydrodiphenyl, characterized in that 4.4'-diamino = 3.3'-dimethoxy-diphenyl-cyclohexane by heating to a higher temperature in 4-amino 3-methoxy-tetrahydrodiphenyl transferred and this is treated with hydrogen in the presence of a heavy metal catalyst under pressure.
The reaction is expediently carried out in one operation without separation of the tetrahydrodiphenyl derivative.
The 4-amino-3-methoxy-hexahydrodiphenyl obtained in this way, which has not yet been described, crystallizes toluene or gasoline in the form of broad, glossy, colorless flakes with a melting point of 107.
The product is intended to be used as an intermediate in the manufacture of dyes and pharmaceutical products. <I> Example: </I> 4. 4'-Diamino - 3. 3'-dimethoxy-diphenyl-cyclohexane, as obtained by the process of Swiss patent no. 138194, is broken down into two fractions by distillation in vacuo. The fraction, which passes under a pressure of 12 mm at 180-220, is purified using the sparingly soluble hydrochloric acid salt.
57 kg of the 4-amino-3-methoxy-tetrahydro-diphenyl obtained in this way are heated with .1 (1 kg of decahydronaphthalene and 2.5 kg of a previously reduced hydrogenation catalyst in a stirred autoclave at 50-80 atmospheres of hydrogen.
The uptake of the amount calculated to 1 mol. Takes place rapidly at <B> 80-100 '. </B> During work-up, the as yet not described 4-amino-3-methoxy-hexahydrodiphenyl is obtained: the same product is obtained if you have 4. 4'-diamino - 3. 3'-dimethoxy - cyclohexane treated directly with hydrogen.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE145308X | 1928-04-30 | ||
| CH143386T | 1929-04-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH145308A true CH145308A (en) | 1931-02-15 |
Family
ID=25714262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH145308D CH145308A (en) | 1928-04-30 | 1929-04-26 | Process for the preparation of a derivative of cyclohexylbenzene. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH145308A (en) |
-
1929
- 1929-04-26 CH CH145308D patent/CH145308A/en unknown
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