Aniline → 2-(1,3-Dimethylbutyl)aniline

HRID 883810

Reaktionsgleichung

Reaktionsgleichung von HRID 883810
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][CH:9]([CH3:13])[CH2:10][CH:11]=[CH2:12].[OH-].[Na+]>CC[Al](Cl)CC.CC[Al](Cl)Cl>[CH3:12][CH:11]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:1])[CH2:10][CH:9]([CH3:13])[CH3:8]

Komponenten

5

Edukt 3

HCID 6115AnilineHCID 127244-Methyl-1-penteneHCID 14798Sodium Hydroxide

Produkt 1

HCID 115284412-(1,3-Dimethylbutyl)anilineAusbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 25508Ethylaluminum sesquichlorideKatalysator

Versuchsvorschrift

Aniline (209.5 g, 2.25 mol) was treated with ethylaluminum sesquichioride (39.0 g, 0.158 mol) in the reactor as described in Example 1. 4-Methyl-1-pentene (190 g, 2.26 mol) was added and the mixture was held at 260-262° C. for 17 hours. Reactor contents were cooled to ambient temperature and treated with 25% aqueous sodium hydroxide solution. Aqueous phase was removed and the organic phase (388 g) was analyzed to contain 21.9 wt % aniline and 41.1 wt % 2-(1,3-dimethylbutyl)aniline. Aniline conversion was found to be 59.4% and 2-(1,3-dimethylbutyl)aniline yield was found to be 40% based on aniline charged or 67.3% based on aniline reacted. Crude product from this and from another similar experiment were combined and the total (767 g) was fractionally distilled at reduced pressure to give 290 g of pure 2-(1,3-dimethylbutyl)aniline (290 g, 36% yield based on aniline charged).

Aufarbeitung

  1. customAqueous phase was removed
  2. customyield
  3. additioncharged
  4. customreacted
  5. distillationthe total (767 g) was fractionally distilled at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f04efa5944ab41e082e1794d737ad245
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236988B2

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