Methyl Methacrylate → Stearyl methacrylate

HRID 1764757Notes

Reaction equation

HRID 1764757 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:8](O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]C.[C-]#N.[K+].COC1C=CC(O)=CC=1>>[C:1]([O:6][CH2:7][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Reactant 4

HCID 6658Methyl MethacrylateHCID 8221Stearyl AlcoholHCID 90154-MethoxyphenolHCID 9032Potassium Cyanide

Product 1

HCID 122600Stearyl methacrylate

Conditions

Temperature
75 °C

Procedure

300 g of methyl methacrylate (3 mole), 135 g of stearyl alcohol (0.5 mole), 4.35 g of KCN (1%) and 0.108 g of hydroquinone methyl ether (250 ppm) are added to a 1 liter round-bottomed flask. The mixture is heated to about 75° C. by conducting air through it and the methyl methacrylate/methanol-azeotrope is removed at a temperature of 65° C. at the head of the column by way of a 1 m vigreux column. The trans-esterification is completed after 3.5 hours. After cooling down of the flask, the sump is filtered to remove the potassium cyanide, and the filter residue is washed with a little methyl methacrylate. The filtrate is concentrated at 40° C. under a water jet vacuum. A white, crystalline residue of stearyl methacrylate of 162 g = 96% will result.

Workup

  1. customthe methyl methacrylate/methanol-azeotrope is removed at a temperature of 65° C. at the head of the column by way of a 1 m vigreux column
  2. temperatureAfter cooling down of the flask
  3. filtrationthe sump is filtered
  4. customto remove the potassium cyanide
  5. washthe filter residue is washed with a little methyl methacrylate
  6. concentrationThe filtrate is concentrated at 40° C. under a water jet vacuum

Sources & evidence

ORD record
ord-45e06bf162dd41209c860029ac67eea3
Source dataset
uspto-grants-1978_09
Patent number
US04117238

Reaction notes

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