Oxygen → Cyclohexanol

HRID 1174062Notes

Reaction equation

HRID 1174062 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:7]N1[C:12](=[O:13])[CH2:11][CH2:10][C:9]1=O.[O:15]=[O:16]>>[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:12]1([OH:13])[CH2:11][CH2:10][CH2:9][CH2:2][CH2:1]1.[CH:1]1([O:15][OH:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 977OxygenHCID 8078Cyclohexane2×HCID 80170N-Hydroxysuccinimide2×

Product 3

HCID 7966CyclohexanolHCID 7967CyclohexanoneHCID 69835Cyclohexyl hydroperoxide

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 and 2 g of a 5 percent by weight N-hydroxysuccinimide aqueous solution which contained 100 mg of N-hydroxysuccinimide dissolved therein, 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 aqueous solution therein was stirred at 150° C. for 1 hour. As a result, 36 mmol of cyclohexane reacted (with a conversion of 3.8%) and thereby yielded 9.2 mmol of cyclohexanone (with a selectivity of 25.6%), 4.6 mmol of cyclohexanol (with a selectivity of 12.8%), and 12.3 mmol of cyclohexyl hydroperoxide (with a selectivity of 34.2%). The total yield of cyclohexanone, cyclohexanol, and cyclohexyl hydroperoxide was 2.7%.

Workup

  1. customequipped with a stirrer
  2. dissolutiondissolved
  3. customat room temperature
  4. custom(25° C.)
  5. customThe autoclave was hermetically sealed

Sources & evidence

ORD record
ord-22ad10dbd2494f6dae1f524c349f3119
Source dataset
uspto-grants-2010_11
Patent number
US07834217B2

Reaction notes

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