Methanol → Undecylenyl Triethyl Ammonium Iodide Eicosene

HRID 373757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373757
[CH2:1]([I:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[CH2:13]([NH+:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:14].[CH2:20]=[CH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].[Cl-].C([Al+]CC)C.CO>C1(C)C=CC=CC=1>[I-:12].[CH2:1]([N+:15]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[CH2:20]=[CH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Komponenten

6

Edukt 4

HCID 887Methanol2×HCID 189361-EicoseneHCID 16686102Diethyl aluminum chlorideHCID 19383009Triethylammonium undecylenyl iodide

Produkt 1

HCID 131717651Undecylenyl Triethyl Ammonium Iodide EicoseneAusbeute 146,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

Triethyl ammonium undecylenyl iodide (7.5 grams), eicosene (22.5 grams) and toluene (60 grams) were added to a glass screw cap jar under an argon atmosphere. Diethyl aluminum chloride (25 milliliters of a 1.8 molar solution in toluene) and 1.25 teaspoons of TiCl3 --AA (available from Alfa, about 5 grams) were added. After 1.5 hours, the reaction was treated with methanol until the mixture turned green. The mixture was added to methanol in a Waring blender to precipitate the polymer which was washed successively with water and then methanol. The solid polymer was isolated by filtration and dried in vacuo to afford 19 grams of a white powder. Solid state 13C NMR analysis was consistent with the attachment of 5 weight percent of quaternary ammonium groups. The DSC of this product showed two semicrystalline melting endotherms at 45° and 81° C. and a melting peak at 117° C. attributed to the quaternary ammonium iodide group.

Aufarbeitung

  1. customcap jar under an argon atmosphere
  2. customto precipitate the polymer which
  3. washwas washed successively with water
  4. customThe solid polymer was isolated by filtration
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-84efca4cae5649659ab94a8493f5b6dc
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166026

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