Tridecane → 1H,1H,2H-Perfluorocyclopentane

HRID 2186582Notes

Reaction equation

HRID 2186582 reaction equation
CCCCCCCCCCCCC.[H][H].[F:16][C:17]1[C:21]([F:23])([F:22])[C:20]([F:25])([F:24])[C:19]([F:27])([F:26])[CH:18]=1>[Pd]>[F:26][C:19]1([F:27])[CH2:18][CH:17]([F:16])[C:21]([F:22])([F:23])[C:20]1([F:24])[F:25].[F:22][C:21]1([F:23])[CH2:17][CH2:18][C:19]([F:27])([F:26])[C:20]1([F:24])[F:25]

Participants

6

Reactant 3

HCID 12388Tridecane2×HCID 117693841,3,3,4,4,5,5-Heptafluoro-Cyclopentene2×HCID 178418361HCID 178418361, compound

Product 2

HCID 38532451H,1H,2H-PerfluorocyclopentaneHCID 109975961,1,2,2,3,3-hexafluorocyclopentane

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
40 °C

Procedure

One percent by weight of n-tridecane (dielectric constant 2.0), a low-polarity compound, was dissolved in crude 1,3,3,4,4,5,5-heptafluorocyclopentene having a purity of 99.9 GC %. An autoclave having a capacity of 100 ml was charged with a catalyst of activated carbon having supported thereon 5% by weight of powdered palladium. After the deaeration under reduced pressure, n-tridecane-containing 1,3,3,4,4,5,5-heptafluorocyclopentene prepared previously was poured. While the mixture was stirred at 40° C., the reaction was conducted by repeating block charge of hydrogen at a gauge pressure in the range of 0 to 6 kgf/cm2. After the completion of the reaction, the product was analyzed through gas chromatography. Consequently, a fluorinated saturated hydrocarbon containing 94 mol % of 1,1,2,2,3,3,4-heptafluorocyclopentane (HFCPA) and 6 mol % of 1,1,2,2,3,3-hexafluorocyclopentane was obtained.

Workup

  1. additionwas charged with a catalyst of activated carbon having
  2. customprepared previously
  3. additionwas poured
  4. customAfter the completion of the reaction

Sources & evidence

ORD record
ord-0b3179cf86ec40ebab1bbcb08969096b
Source dataset
uspto-grants-2002_06
Patent number
US06403846B1

Reaction notes

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