Carbon Dioxide → Phenol

HRID 989476Notes

Reaction equation

HRID 989476 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C([OH:31])CCCCCCC(C)C.[OH-].[Mg+2:33].[OH-].[C:35](=[O:37])=[O:36]>O.C(O)(C)C>[C:1]1([OH:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]([O-:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Mg+2:33].[C:1]([O-:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:35](=[O:31])([O-:37])[O-:36]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 32898IsodecanolHCID 73981Magnesium Hydroxide2×HCID 445639Oleic Acid

Product 2

HCID 996PhenolYield 4.5%HCID 86749490HCID 86749490, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
140 fahrenheit

Procedure

A phenol-free magnesium oleate/carbonate containing about 4.5% magnesium was prepared by the following procedure. A mixture of 529.3 g of oleic acid, 600 g of Shellflex™ 6111 light mineral oil, 400 g of isopropyl alcohol, 350 g of isodecyl alcohol, 400 g of water was heated to 140° F. and 400 g of magnesium hydroxide was added. The neutralization of the acid with the magnesium hydroxide caused the temperature to rise to 167° F. Carbon dioxide gas was passed into the reaction mixture through a subsurface addition tube at a rate of 225 ml/minute for 6 hours, during which time the temperature was gradually raised to 223° F. and 720 ml of a mixture of water and isopropyl alcohol was removed. The temperature was raised to 305° F. and the remaining water was removed with the assistance of the carbon dioxide addition. The carbon dioxide addition was stopped, and the hot reaction mixture was filtered with suction with the assistance of filter aid, giving the overbased magnesium product as a clear light yellow mobile liquid. The product was analyzed to contain 4.5% magnesium by weight.

Workup

  1. customto rise to 167° F
  2. temperaturewas gradually raised to 223° F.
  3. custom720 ml of a mixture of water and isopropyl alcohol was removed
  4. temperatureThe temperature was raised to 305° F.
  5. customthe remaining water was removed with the assistance of the carbon dioxide addition
  6. additionThe carbon dioxide addition
  7. filtrationthe hot reaction mixture was filtered with suction with the assistance of filter aid

Sources & evidence

ORD record
ord-3b325acf4c4b46cc87b1516a5b6329d5
Source dataset
uspto-grants-2003_10
Patent number
US06639090B2

Reaction notes

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