Sulfuric Acid → Hexafluoroacetylacetone

HRID 1934872Notes

Reaction equation

HRID 1934872 reaction equation
[CH2:1]([C:9](O)([OH:14])[C:10]([F:13])([F:12])[F:11])[C:2](O)([OH:7])[C:3]([F:6])([F:5])[F:4].S(=O)(=O)(O)O>>[CH2:1]([C:2]([C:3]([F:4])([F:5])[F:6])=[O:7])[C:9]([C:10]([F:11])([F:13])[F:12])=[O:14]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 1441991,1,1,5,5,5-Hexafluoro-2,2,4,4-pentane-t etrol, 97

Product 1

HCID 73706Hexafluoroacetylacetone

Procedure

To the obtained crude 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate 70 ml of toluene were added, followed by stirring for 1 hr at room temperature with a magnetic mixer, then filtration and then drying, thereby obtaining 27.3 g of 1,1,1,,5,5,5-hexafluoroacetylacetone dihydrate (see Table). A 100-ml glass reaction vessel, equipped with a thermometer, a stirrer and a reflux condenser filled with glass spheres, was charged with 27.3 g of the obtained 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate and 55 g of 98% sulfuric acid, while nitrogen gas was allowed to flow through the reaction vessel. Then, the mixture was gradually heated to 80° C. with stirring by a magnetic mixer. During this heating, 21.0 g of a distillate of about 70° C. was collected. This distillate was found by the same gas chromatography as that of Example 1 to be 1,1,1,5,5,5-hexafluoroacetylacetone having a purity of 99.9%.

Workup

  1. additionwere added
  2. filtrationfiltration
  3. customdrying
  4. customobtaining 27.3 g of 1,1,1,,5,5,5-hexafluoroacetylacetone dihydrate (see Table)
  5. customequipped with a thermometer, a stirrer and a reflux condenser
  6. additionfilled with glass spheres
  7. temperatureThen, the mixture was gradually heated to 80° C.
  8. stirringwith stirring by a magnetic mixer
  9. distillationDuring this heating, 21.0 g of a distillate of about 70° C. was collected

Sources & evidence

ORD record
ord-7c319a972d1c44e0a94d898942bdda42
Source dataset
uspto-grants-2002_05
Patent number
US06384286B1

Reaction notes

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