CH193616A - Process for the preparation of p-dodecylaniline. - Google Patents
Process for the preparation of p-dodecylaniline.Info
- Publication number
- CH193616A CH193616A CH193616DA CH193616A CH 193616 A CH193616 A CH 193616A CH 193616D A CH193616D A CH 193616DA CH 193616 A CH193616 A CH 193616A
- Authority
- CH
- Switzerland
- Prior art keywords
- dodecylaniline
- aniline
- added
- preparation
- reaction mixture
- Prior art date
Links
- KLPPPIIIEMUEGP-UHFFFAOYSA-N 4-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=C(N)C=C1 KLPPPIIIEMUEGP-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 3
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011592 zinc chloride Substances 0.000 claims description 4
- 235000005074 zinc chloride Nutrition 0.000 claims description 4
- -1 zinc halide Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 238000009835 boiling Methods 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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000007711 solidification Methods 0.000 claims 1
- 230000008023 solidification Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von p-Dodeeylanilin. Vorliegendes Patent betrifft ein Verfahren zur Herstellung von p-Dodecylanilin, welches dadurch gekennzeichnet ist, dass man Anilin mit Dodecylalkohol in Gegenwart eines Zink halogeriides erhitzt. Das Zinkhalogenid kann z. B. Zinkchlorid sein.
Zwecks Erhöhung der Ausbeute kann auch eine Halogenwasserstoffsäure zugesetzt wer den.
p-Dodecylanilin stellt ein wertvolles Farb- stoffzwischenprodukt dar.
<I>Beispiel:</I> 558 Teile Dodecylalkohol, 373 Teile Ani lin, 37 Teile Chlorwasserstoffsäure und 245 Teile Zinkchlorid werden zusammen während 10 Stunden auf 2400 C erhitzt, wobei das durch die Reaktion entstandene Wasser ab destillieren kann. Das Erhitzen. wird während weiterer 12 Stunden bei 2400 C fortgesetzt. Das Gemisch wird dann mit einem Über schuss an Natriumhydroxydlösung gekocht, wodurch die entstandene Doppelverbindung des Zinkchlorids zersetzt wird.
Das Öl wird abgetrennt und der Vakuumdestillation unter worfen, wobei der bei 200-235 C und 11 mm Druck destillierende Teil gesammelt wird. p-Dodecylanilin wird auf diese Weise in guter Ausbeute erhalten. p-Dodecylanilin ist eine neue Verbindung und ist eine weisse, kristallinische Substanz mit einem Erstarrungs- punkt von 35 C und einem Siedepunkt von 220-221<B>0</B> C bei 15 mm Druck. Ihr Acetyl- derivat schmilzt bei 100 C.
Process for the preparation of p-dodecylaniline. The present patent relates to a process for the preparation of p-dodecylaniline, which is characterized in that aniline is heated with dodecyl alcohol in the presence of a zinc halide. The zinc halide can e.g. B. be zinc chloride.
A hydrohalic acid can also be added to increase the yield.
p-Dodecylaniline is a valuable intermediate dye product.
<I> Example: </I> 558 parts of dodecyl alcohol, 373 parts of aniline, 37 parts of hydrochloric acid and 245 parts of zinc chloride are heated together to 2400 ° C. for 10 hours, the water formed by the reaction being able to distill off. The heating. is continued for a further 12 hours at 2400 C. The mixture is then boiled with an excess of sodium hydroxide solution, whereby the resulting double compound of zinc chloride is decomposed.
The oil is separated and subjected to vacuum distillation, collecting the part which distills at 200-235 ° C. and 11 mm pressure. p-Dodecylaniline is obtained in this way in good yield. p-Dodecylaniline is a new compound and is a white, crystalline substance with a freezing point of 35 C and a boiling point of 220-221 <B> 0 </B> C at 15 mm pressure. Your acetyl derivative melts at 100 C.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB193616X | 1935-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH193616A true CH193616A (en) | 1937-10-31 |
Family
ID=10128068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH193616D CH193616A (en) | 1935-12-31 | 1936-12-19 | Process for the preparation of p-dodecylaniline. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH193616A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0025934A1 (en) * | 1979-09-22 | 1981-04-01 | BASF Aktiengesellschaft | Process for the production of p-substituted aromatic amines |
-
1936
- 1936-12-19 CH CH193616D patent/CH193616A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0025934A1 (en) * | 1979-09-22 | 1981-04-01 | BASF Aktiengesellschaft | Process for the production of p-substituted aromatic amines |
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