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Phosgene → p-Cyclododecylphenol

HRID 1897394
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1897394
C(N(CC)CC)C.C(Cl)(Cl)=O.ClC([O-])=O.[OH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2(C3C=CC(O)=CC=3)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1>C(Cl)Cl>[OH:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6371PhosgeneHCID 8471Triethylamine2×HCID 158500604,4'-(Cyclododecane-1,1-diyl)diphenol2×HCID 21226386Carbonochloridate

Produkt 1

HCID 19391072p-Cyclododecylphenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
18.75 °C

Versuchsvorschrift

43.6 g (0.124 mol) of 1,1-bis(4-hydroxyphenyl)-cyclododecane was suspended in 410 mL of methylene chloride, to which 25.0 g (0.248 mol) of triethylamine was added for dissolution. The obtained solution was dropped into a solution, which was prepared by dissolving 24.8 g (0.250 mol) of phosgene in 225 mL of methylene chloride, at 14 to 18.5 degrees C. for 2 hours and 50 minutes. After stirring at 18.5 to 19 degrees C. for one hour, 250 mL of methylene chloride was distilled away at 10 to 22 degrees C. 73 mL of deionized water, 4.5 mL of concentrated hydrochloric acid and 0.47 g of hydrosulphite were added to the residual solution for cleaning. Subsequently, cleaning with 330 mL of deionized water was repeated four times. A methylene chloride solution of a 1,1-bis(4-hydroxyphenyl)-cyclododecane oligomer having a chloroformate group at its molecular terminal was obtained. The obtained solution had a chloroformate concentration of 0.92 mol/L, a solid concentration of 0.23 kg/L and an average number of repeating units of 1.06. A content of an amide compound in the obtained 1,1-bis(4-hydroxyphenyl)-cyclododecane oligomer was found to be 210 mass ppm. A mass of nitrogen derived from triethylamine was 0.3 mass ppm. This obtained ingredient will be referred to as “CDE-CF” hereinafter.

Aufarbeitung

  1. additionwas added for dissolution
  2. additionThe obtained solution was dropped into a solution, which
  3. customwas prepared
  4. customat 14 to 18.5 degrees C
  5. custom50 minutes
  6. waitfor one hour
  7. distillation250 mL of methylene chloride was distilled away at 10 to 22 degrees C
  8. addition73 mL of deionized water, 4.5 mL of concentrated hydrochloric acid and 0.47 g of hydrosulphite were added to the residual solution for cleaning
  9. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-d4b72ec882c94d4bb486dee784e7f004
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08519082B2

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