CH201512A - Process for the preparation of p-dodecylaniline. - Google Patents
Process for the preparation of p-dodecylaniline.Info
- Publication number
- CH201512A CH201512A CH201512DA CH201512A CH 201512 A CH201512 A CH 201512A CH 201512D A CH201512D A CH 201512DA CH 201512 A CH201512 A CH 201512A
- Authority
- CH
- Switzerland
- Prior art keywords
- dodecylaniline
- aniline
- cobalt
- preparation
- dodecyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- KLPPPIIIEMUEGP-UHFFFAOYSA-N 4-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=C(N)C=C1 KLPPPIIIEMUEGP-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 8
- -1 cobalt halide Chemical class 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical group [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- SOANRMMGFPUDDF-UHFFFAOYSA-N 2-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=CC=C1N SOANRMMGFPUDDF-UHFFFAOYSA-N 0.000 description 1
- 229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- ASKVAEGIVYSGNY-UHFFFAOYSA-L cobalt(ii) hydroxide Chemical compound [OH-].[OH-].[Co+2] ASKVAEGIVYSGNY-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von p-Dodecylanilin. Im Patent Nr. 193616 ist ein Verfahren zur Herstellung einer neuen Verbindung, des p-Dodecylanilins durch Erhitzen von Anilin mit Dodecylalkohol in Gegenwart eines Zink halogenides, beschrieben.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung des p-Dodecyl- anilins, welches dadurch gekennzeichnet ist, dass man Anilin mit Dode(,ylalkt)hol und einem Kobalthalogenid erhitzt. Das Kobalt halogenid kann zum Beispiel Kobaltchlorid sein. Zwecks Erhöhung der Ausbeute kann auch eine Halogenwasserstoffsäure, z.B. Brom wasserstoffsäure, zugesetzt werden. p-Dodecyl- anilin stellt ein wertvolles Farbstoffzwischen- produkt dar.
Beispiel: 248,5 Teile Anilin, 352 Teile Dodecyl- alkohol, 288 Teile Kobaltchloridkristalle (Co0ls .6H20) und 24,5 Teile Chlorwasser stoffsäure werden zusammen während über 10 Stunden auf 200-240o C erhitzt. Wäh rend dieser Zeit destilliert Wasser ab; das Kobaltchlorid geht in Lösung über und es ergibt sich ein hellbläulich-grünes Gemisch. Das Erhitzen wird während weiterer 12 Stun den bei 235-240o C fortgesetzt und das Gemisch wird hierauf in ein grosses Quantum von Natriumhydroxydlösung gegossen.
Das Gemisch wird für eine weitere Stunde ge kocht, wodurch die gobaltkomplexe sich zer setzen und das Rohdodecylanilin auf einer wässerigen Suspension von Kobalthydroxyd als Öl schwimmt. Das Öl wird durch Dekan tieren und Filtrieren getrennt und ein etwaiger noch im Rückstand auf dem Filter verblei bender Rest wird mittelst Benzol oder Äther extrahiert. Das Ö1 wird durch Schütteln mit 10 Teilen warmer 30 o/oigerNatriumhydroxyd- flüssigkeit bei 50 C getrocknet, getrennt und im Vakuum destilliert; der bei 200-235 o C und 11 mm Druck destillierende Teil wird aufgefangen.
p-1)odecylanilin ist eine weisse, kristallini sche Substanz, deren Kristallisationspunkt bei 35 C und deren Siedepunkt bei 220-221 C unter<B>15</B> mm Druck liegt. Ihr Acetylderivat schmilzt bei 100 C.
Process for the preparation of p-dodecylaniline. Patent No. 193616 describes a process for the preparation of a new compound, p-dodecylaniline, by heating aniline with dodecyl alcohol in the presence of a zinc halide.
The subject of the present patent is a process for the preparation of p-dodecyl aniline, which is characterized in that aniline is heated with dodecyl alcohol and a cobalt halide. The cobalt halide can be cobalt chloride, for example. To increase the yield, a hydrohalic acid, e.g. Hydrobromic acid. p-Dodecyl aniline is a valuable intermediate dye product.
Example: 248.5 parts of aniline, 352 parts of dodecyl alcohol, 288 parts of cobalt chloride crystals (CoOls .6H20) and 24.5 parts of hydrochloric acid are heated together to 200-240 ° C. for over 10 hours. During this time, water distills off; the cobalt chloride goes into solution and a light bluish-green mixture results. Heating is continued for a further 12 hours at 235-240 ° C. and the mixture is then poured into a large quantity of sodium hydroxide solution.
The mixture is boiled for a further hour, as a result of which the cobalt complexes decompose and the crude dodecylaniline floats as an oil on an aqueous suspension of cobalt hydroxide. The oil is separated by decanting and filtering, and any residue remaining on the filter is extracted with benzene or ether. The oil is dried by shaking with 10 parts of warm 30% sodium hydroxide liquid at 50 ° C., separated and distilled in vacuo; the part that distills at 200-235 o C and 11 mm pressure is collected.
p-1) Odecylaniline is a white, crystalline substance, the crystallization point of which is 35 C and the boiling point 220-221 C under <B> 15 </B> mm pressure. Their acetyl derivative melts at 100 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB201512X | 1935-12-31 | ||
| CH193616T | 1936-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH201512A true CH201512A (en) | 1938-11-30 |
Family
ID=25722537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH201512D CH201512A (en) | 1935-12-31 | 1936-12-19 | Process for the preparation of p-dodecylaniline. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH201512A (en) |
-
1936
- 1936-12-19 CH CH201512D patent/CH201512A/en unknown
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