Sulfuric Acid → Tetrafluorosuccinyl fluoride

HRID 1764485Notes

Reaction equation

HRID 1764485 reaction equation
S(=O)(=O)(O)O.IC(F)(F)C(F)(F)C(F)(F)C(F)([F:12])I.[F:20][C:21]1([F:31])[C:26]([F:28])([F:27])[C:25]([F:30])(F)[O:24][C:22]1=[O:23]>>[F:27][C:26]([F:28])([C:21]([F:31])([F:20])[C:22]([F:12])=[O:23])[C:25]([F:30])=[O:24]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 78993Perfluoro-1,4-diiodobutaneHCID 125616193,3,4,4,5,5-Hexafluorooxolan-2-one

Product 1

HCID 2776618Tetrafluorosuccinyl fluorideYield 11%

Conditions

Temperature
85 °C

Procedure

Into a four necked flask equipped with a thermometer, a reflux condenser, a dropping funnel and a magnetic stirrer, 4950 g (18.5 moles as SO3) of fuming sulfuric acid containing 30% of SO3 were charged. The flask was heated to 85° C. and then, 990 g (2.2 moles) of 1,4-diiodoperfluorobutane having the forumla I (CF2)4I were added dropwise to the flask. The reaction was conducted for 6 hours while maintaining the temperature in the reactor at 85° to 95° C. The reaction mixture discharged from the reflux condenser, was passed through a gas washing bottle containing concentrated sulfuric acid and was collected in a flask cooled with a dryice-ethanol coolant. The collected reaction products in the flask were separated by distillation whereby 247 g of a fraction of a boiling point of 18° C. were obtained. According to F19NMR analysis of the fractions, the fraction having a boiling point of 18° C. consisted of 200g (yield of 47%) of perfluoro- γ-butyrolactone and 47 g (yield of 11%) of perfluorosuccinic difluoride. Another fraction having a boiling point of 1° C., 45 g (yield of 11% ) of perfluoroetrahydrofuran was also obtained.

Workup

  1. additionwere charged
  2. temperaturewhile maintaining the temperature in the reactor at 85° to 95° C
  3. washwashing bottle
  4. additioncontaining concentrated sulfuric acid
  5. customwas collected in a flask
  6. temperaturecooled with a dryice-ethanol coolant
  7. customThe collected reaction products in the flask
  8. customwere separated by distillation whereby 247 g of a fraction of a boiling point of 18° C.
  9. customwere obtained

Sources & evidence

ORD record
ord-f688288e941d441ea70829f3997dffb7
Source dataset
uspto-grants-1978_09
Patent number
US04116977

Reaction notes

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