2-Chloroethanol → HCID 131729245, Verbindung

HRID 554062

Reaktionsgleichung

Reaktionsgleichung von HRID 554062
[CH2:1]=[CH:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][CH:17]=1.ClCCO.C([O-])([O-])=O.[K+].[K+].[CH2:33]([N:42]=[C:43]=[O:44])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][N:39]=[C:40]=[O:41].[CH3:45][C:46]([C:48]([O:50][CH2:51][CH2:52][OH:53])=[O:49])=[CH2:47]>CN(C=O)C.O>[CH2:1]=[CH:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][CH:17]=1.[CH2:35]([CH2:34][CH2:33][N:42]=[C:43]=[O:44])[CH2:36][CH2:37][CH2:38][N:39]=[C:40]=[O:41].[CH3:47][C:46]([C:48]([O:50][CH2:51][CH2:52][OH:53])=[O:49])=[CH2:45]

Komponenten

8

Edukt 5

HCID 342-ChloroethanolHCID 11430Potassium CarbonateHCID 13192Hexamethylene diisocyanateHCID 133602-Hydroxyethyl MethacrylateHCID 11266523Cardanol2×

Produkt 1

HCID 131729245HCID 131729245, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Cardanol was modified by coupling it with 2-chloroethanol in presence of K2CO3 and KI in DMF under inert atmosphere. Hexamethylene diisocyanate [HMDI] (0.49 g, 0.003 moles) in 10 ml dry DMF was taken in a 100 ml two necked flask and the contents were cooled with ice. HEMA (0.38 g, 0.003 moles) was added drop wise with constant stirring under nitrogen. The reaction was allowed to proceed under ice cold condition for 2 hr. Then the reaction was kept at room temperature for 1 hr. After that the reaction was changed to ice cold condition and 3 drops of DBTDL was added as catalyst followed by drop wise addition of modified cardanol (1 g, 0.003 moles) in 10 ml DMF. It was left stirring under cold condition for a further 1 hr and allowed to attain room temperature. Then the reaction was heated to 50° C. for 12 hrs. The contents were poured to 150 ml water and extracted with dichloromethane. It was then washed with plenty of water and dried in vacuum oven at 60° C. for 12 hrs. Yield=62% (1.17 g). The same synthetic procedure is adopted for all types of variation in the diisocyanate chemistry or in the hydroxy(meth)acryloxy chemistry or natural resource with active hydrogen atom to obtain the final UV curable telechelic pre polymer with varying R1, R2, R3, R4, R5 and R6.

Aufarbeitung

  1. temperaturethe contents were cooled with ice
  2. customfor 2 hr
  3. additionwas added as catalyst
  4. waitIt was left
  5. stirringstirring under cold condition for a further 1 hr
  6. customto attain room temperature
  7. extractionextracted with dichloromethane
  8. washIt was then washed with plenty of water
  9. customdried in vacuum oven at 60° C. for 12 hrs
  10. customto obtain the final UV curable telechelic pre polymer with varying R1, R2, R3, R4, R5 and R6

Quellen und Nachweise

ORD-Eintrag
ord-40762ffc358245eabd6dd48c30a9c1a1
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048979B2

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