Sulfuric Acid → C4F9CH2CF2CH2CH2OH

HRID 640772Notes

Reaction equation

HRID 640772 reaction equation
[C:1]([CH2:14][C:15]([CH2:18][CH2:19]I)([F:17])[F:16])([C:4]([C:7]([C:10]([F:13])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].S(=O)(=O)(O)[OH:22]>>[C:1]([CH2:14][C:15]([CH2:18][CH2:19][OH:22])([F:17])[F:16])([C:4]([C:7]([C:10]([F:13])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 858357771,1,1,2,2,3,3,4,4,6,6-Undecafluoro-8-iodooctane

Product 1

HCID 57526216C4F9CH2CF2CH2CH2OH

Conditions

Temperature
60 °C

Procedure

Ethylene (25 g) was introduced to an autoclave charged with C4F9CH2CF2I (217 g) and d-(+)-limonene (1 g), and the reactor heated at 240° C. for 12 hours. The product was isolated by vacuum distillation to provide C4F9CH2CF2CH2CH2I. Fuming sulfuric acid (70 mL) was added slowly to 50 g of C4F9CH2CF2CH2CH2I and mixture was stirred at 60° C. for 1.5 hours. The reaction was quenched with ice-cold 1.5 wt % Na2SO3 aqueous solution and heated at 95° C. for 0.5 hours. The bottom layer was separated and washed with 10 wt % aqueous sodium acetate and distilled to provide C4F9CH2CF2CH2CH2OH bp 54-57° C. at 2 mmHg (267 Pa).

Workup

  1. customThe reaction was quenched with ice-cold 1.5 wt % Na2SO3 aqueous solution
  2. temperatureheated at 95° C. for 0.5 hours
  3. customThe bottom layer was separated
  4. washwashed with 10 wt % aqueous sodium acetate
  5. distillationdistilled

Sources & evidence

ORD record
ord-19ba2cc6e1304ef88f6f8041ada8a29a
Source dataset
uspto-grants-2010_04
Patent number
US07692035B2

Reaction notes

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