Fluorine → Perfluorooctane sulfonic anhydride

HRID 2393963Notes

Reaction equation

[C:1]([S:26]([OH:29])(=[O:28])=[O:27])([C:4]([C:7]([C:10]([C:13]([C:16]([C:19]([C:22]([F:25])([F:24])[F:23])([F:21])[F:20])([F:18])[F:17])([F:15])[F:14])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].[P].FF>>[O:27]([S:26]([C:1]([C:4]([C:7]([C:10]([C:13]([C:16]([C:19]([C:22]([F:23])([F:24])[F:25])([F:20])[F:21])([F:17])[F:18])([F:15])[F:14])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2])(=[O:28])=[O:27])[S:26]([C:1]([C:4]([C:7]([C:10]([C:13]([C:16]([C:19]([C:22]([F:24])([F:25])[F:23])([F:21])[F:20])([F:18])[F:17])([F:15])[F:14])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2])(=[O:29])=[O:28]

Participants

Reactant 3

HCID 24524Fluorine

HCID 74483Perfluorooctanesulfonic acid

HCID 5462309Phosphorus

Product 1

HCID 54444622Perfluorooctane sulfonic anhydrideYield 37%

Procedure

Then, the first distillation of Example 14 was repeated, thereby to obtain 79.9 kg of (C8F17SO2)2O which is colorless and transparent. By chemical analysis, this first distillate was found to have a purity of 91 wt % and contain 5 wt % of C8F17 SO2.OC8F17, 2 wt % of C7F15SO2.OC7 F15, up to 0.5 wt % of C6F13SO2.OC6F13, 2 wt % of C8F17SO3H, up to 0.5 wt % of C7F15 SO3H, 620 wt ppm of phosphorus, and 4,100 wt ppm of free fluorine. The amount of (C8F17SO2)2O produced by the reaction was 72.7 kg, and the yield was 37%, based on the amount of C8 F17SO3H.

Sources & evidence

ORD record: ord-c3188986d6484896945b70e388b2a458
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05808149

Reaction notes

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