Oxygen → Cyclohexanol

HRID 1174065Notes

Reaction equation

HRID 1174065 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:7]N1C(=O)[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2C1=O.[O:19]=[O:20]>O>[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:10]1([OH:19])[CH2:11][CH2:14][CH2:15][CH2:16][CH2:17]1.[CH:1]1([O:19][OH:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 977OxygenHCID 8078Cyclohexane2×HCID 10665N-Hydroxyphthalimide

Product 3

HCID 7966CyclohexanolHCID 7967CyclohexanoneHCID 69835Cyclohexyl hydroperoxide

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 (0.95 mol) of cyclohexane, 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, 5.9 mmol of cyclohexane reacted (with a conversion of 0.7%) and thereby yielded 0.3 mmol of cyclohexanone (with a selectivity of 5.1%), 0.2 mmol of cyclohexanol (with a selectivity of 3.4%), and 3.8 mmol of cyclohexyl hydroperoxide (with a selectivity of 64.4%). The total yield of cyclohexanone, cyclohexanol, and cyclohexyl hydroperoxide was 0.45%. 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-512212e3db2b4042b214549768b6d7e5
Source dataset
uspto-grants-2010_11
Patent number
US07834217B2

Reaction notes

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