Oxygen → 2-Hexanone

HRID 2083272Notes

Reaction equation

HRID 2083272 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6].C([OH:10])(C)C.O=O>[Pd](Cl)Cl.O>[CH3:1][C:2](=[O:10])[CH2:3][CH2:4][CH2:5][CH3:6].[CH3:1][CH2:2][C:3](=[O:10])[CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 3

HCID 977OxygenHCID 3776IsopropanolHCID 115971-Hexene

Product 2

HCID 115093-HexanoneYield 20%HCID 115832-HexanoneYield 41%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

The operating conditions are substantially those of example 29: 0.236 mole of 1-hexene (30 cc), 65 cc of anhydrous isopropanol, 2 millimoles of palladium chloride, 4 millimoles of Cu (ClO4)2 (HMPT)4 complex and 5 cc water are introduced into a heat-insulated reactor and stirred at 40° C at a pH of about 7. After 4 hours of reaction, 25 millimoles of oxygen is absorbed; 25 millimoles of 2-hexanone (selectivity: 41%) and 12 millimoles of 3-hexanone (selectivity: 20%) is formed; 60 millimoles of 1-hexene is consumed. Thus, not only the activity is low but it is found that a mixture of two ketones is formed, instead of only 2-hexanone as in example 29.

Workup

  1. customis absorbed

Sources & evidence

ORD record
ord-d7e39f46b5df4597b8c449b1385bcd85
Source dataset
uspto-grants-1978_04
Patent number
US04085145

Reaction notes

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