Decane, 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-iodo- → 1,1,2,2-Tetrahydroperfluorodecanethiol

HRID 1936976

Reaktionsgleichung

Reaktionsgleichung von HRID 1936976
N[C:2](N)=[S:3].[F:5][C:6]([F:32])([CH2:29]CI)[C:7]([F:28])([F:27])[C:8]([F:26])([F:25])[C:9]([F:24])([F:23])[C:10]([F:22])([F:21])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14]>C(O)C>[F:5][C:6]([F:32])([CH2:29][CH2:2][SH:3])[C:7]([F:27])([F:28])[C:8]([F:25])([F:26])[C:9]([F:23])([F:24])[C:10]([F:21])([F:22])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14]

Komponenten

4

Edukt 2

HCID 74885Decane, 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-iodo-HCID 2723790Thiourea

Produkt 1

HCID 5427551,1,2,2-TetrahydroperfluorodecanethiolAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of thiourea (105.7 g, 1.39 moles), 2-(perfluorooctyl)ethyl iodide (531.5 g), 0.926 moles) and anhydrous ethanol (1000 mL) was heated at reflux for 6 hours. Approximately half of the alcohol was removed at reduced pressure and replaced with water. Solid sodium hydroxide (37.0 g) was added and the mixture heated under slow nitrogen purge. The volatile liquid products were collected by steam distillation using a modified Dean-Stark apparatus to yield 414 g (93.1 molar yield) of 2-(perfluorooctyl)ethyl mercaptan. After two consecutive water washes the product was suficiently pure by glc (99.3%) and used without further purification.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. customApproximately half of the alcohol was removed at reduced pressure
  4. additionSolid sodium hydroxide (37.0 g) was added
  5. temperaturethe mixture heated under slow nitrogen
  6. custompurge
  7. distillationThe volatile liquid products were collected by steam distillation

Quellen und Nachweise

ORD-Eintrag
ord-8992845735af4df482151e6c00fc53ea
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06391948B1

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