Water → 2-Dodecanone

HRID 1580329Notes

Reaction equation

HRID 1580329 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[OH2:13].O=O>CO.[Pd](Cl)Cl.[Ti]>[CH3:1][C:2](=[O:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 3

HCID 962WaterHCID 977Oxygen2×HCID 81831-Dodecene3×

Product 1

HCID 225562-Dodecanone

Reagents, catalysts & solvents 3

HCID 23963TitaniumCatalystHCID 24290Palladium ChlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

2-dodecanone is prepared from 1-dodecene according to the process of the present invention as follows: A catalyst solution is prepared by dissolving .04 moles of palladium chloride in a mixture of 137 grams of methanol, 252 grams of polypropylene glycol having an average molecular weight of 430, and 15 grams of water. The catalyst solution is then charged to a 2 liter titanium autoclave where the catalyst solution is heated to a temperature of 60°C; while being stirred at 1,000 r.p.m. with the reactor being pressurized to 100 p.s.i.g. with oxygen. Using a piston pump, 600 grams of 1-dodecene is introduced to the autoclave over a period of 21/2 hours. During this period of addition, the reaction temperature is maintained at 60°C by cooling, with the reaction pressure of 100 p.s.i.g. being maintained by repressuration with oxygen. Stirring is continued for about 1/2 hour after the addition of 1-dodecene is completed.

Workup

  1. customA catalyst solution is prepared
  2. additionDuring this period of addition
  3. temperaturethe reaction temperature is maintained at 60°C
  4. stirringStirring

Sources & evidence

ORD record
ord-2580148b27af4a819588a656e8a0d8df
Source dataset
uspto-grants-1976_01
Patent number
US03932521

Reaction notes

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