Oxygen → Cyclopentanol

HRID 1174064Notes

Reaction equation

HRID 1174064 reaction equation
[CH2:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.ON1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15]C=C2C1=O.[O:18]=[O:19]>O>[C:11]1(=[O:12])[CH2:10][CH2:13][CH2:14][CH2:15]1.[CH:11]1([OH:12])[CH2:10][CH2:13][CH2:14][CH2:15]1.[CH:1]1([O:18][OH:19])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 977OxygenHCID 9253Cyclopentane2×HCID 10665N-Hydroxyphthalimide

Product 3

HCID 7298CyclopentanolHCID 8452CyclopentanoneHCID 13926501Cyclopentaneperoxol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

In a 350-ml autoclave made of stainless steel SUS 316 and equipped with a stirrer were placed 80 g (1.14 mol) of cyclopentane, 100 mg of N-hydroxyphthalimide, and 1.9 g of water (these formed a slurry at room temperature (25° C.)). The autoclave was hermetically sealed, pressurized to 3 MPa (gauge pressure) with a gaseous mixture of 50 percent by volume oxygen and 50 percent by volume nitrogen, and the mixture therein was stirred at 150° C. for 1 hour. As a result, 8.2 mmol of cyclopentane reacted (with a conversion of 0.7%) and thereby yielded 0.5 mmol of cyclopentanone (with a selectivity of 6.1%), 0.2 mmol of cyclopentanol (with a selectivity of 2.4%), and 5.2 mmol of cyclopentyl hydroperoxide (with a selectivity of 63.4%). The total yield of cyclopentanone, cyclopentanol, and cyclopentyl hydroperoxide was 0.52%. N-hydroxyphthalimide has a solubility in water (25° C.) of 0.01 g/100 g-H2O or less.

Workup

  1. customequipped with a stirrer
  2. customthese formed a slurry at room temperature (25° C.))
  3. customThe autoclave was hermetically sealed

Sources & evidence

ORD record
ord-9cdfce36702542e8ae70b1a7ab376f98
Source dataset
uspto-grants-2010_11
Patent number
US07834217B2

Reaction notes

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