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1-Chloro-1,1,3,3,3-pentafluoro-2-propanone → 1-(1,1,1,2,3,3-Hexafluoro-3-chloro-2-propoxy)-pentafluoro-2-propene

HRID 1578333
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1578333
[F-:1].[K+].[Cl:3][C:4]([F:12])([F:11])[C:5]([C:7]([F:10])([F:9])[F:8])=[O:6].S(F)(O[C:17]([F:24])([F:23])[C:18]([F:22])=[C:19]([F:21])[F:20])(=O)=O>COCCOCCOC>[F:8][C:7]([F:10])([F:9])[C:5]([F:1])([O:6][C:17]([F:24])([F:23])[C:18]([F:22])=[C:19]([F:21])[F:20])[C:4]([F:12])([F:11])[Cl:3]
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Komponenten

5

Edukt 3

HCID 66011-Chloro-1,1,3,3,3-pentafluoro-2-propanoneHCID 522689Potassium FluorideHCID 2776028Pentafluoroallyl fluorosulphate

Produkt 1

HCID 234562201-(1,1,1,2,3,3-Hexafluoro-3-chloro-2-propoxy)-pentafluoro-2-propeneAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A suspension of potassium fluoride (5.80 g, 0.10 mol) and diglyme (100 ml) was stirred at 20° C. in a cooling bath while chlorpentafluoroacetone (18.3 g, 0.10 mol) was distilled in. After the potassium fluoride had dissolved, perfluoroallyl fluorosulfate (23.0 g, 0.10 mol) was added rapidly with cooling of the reaction mixture. The resulting exothermic reaction was accompanied by the precipitation of solid. The mixture was stirred at 25° C. for one hour, and then the volatile components were transferred to a trap cooled to -80° C. by heating the reaction mixture at 42` C. (5 mm Hg). The volatile product was distilled from phosphorus pentoxide to give 1-(1,1,1,2,3,3-hexafluoro-3-chloro-2-propoxy)-pentafluoro-2-propene, (19.6 g, 0.059 mol, 59%)pb 85°-86° C. which was characterized by: λmax 5.55 (CF=CF2) and 7-10 μm (CF, C--O); 19F NMR, -68.6 (m) 2F, CF2Cl, -69.1 (m) 2F, CF2O, -78.8 (m) 3F, CF3, -93.2 (d J=54.7 Hz, each member d J=39.8 Hz, t J=7.5 Hz), 1F, cis--CF2 -CF=CF, -105.9 (d J=116.7 Hz, each member, d J=54.7 Hz, t J=24.0 Hz) 1F, trans-CF2 -CF=CF, -141.2 (t J=22.8 Hz, each member m) 1F, CF, and -190.4 ppm (d J=116.7 Hz, each member d J=39.8 Hz, t J=13.4 Hz) 1F, --CF2CF=C.

Aufarbeitung

  1. distillationwas distilled in
  2. dissolutionAfter the potassium fluoride had dissolved
  3. temperaturewith cooling of the reaction mixture
  4. customThe resulting exothermic reaction
  5. customwas accompanied by the precipitation of solid
  6. customthe volatile components were transferred to a trap
  7. temperaturecooled to -80° C.
  8. temperatureby heating the reaction mixture at 42` C
  9. distillationThe volatile product was distilled from phosphorus pentoxide

Quellen und Nachweise

ORD-Eintrag
ord-672db983c42a4458b18fc6c582e76c27
Quelldatensatz
uspto-grants-1981_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04292449

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