Methyl Methacrylate → Cyclohexyl methacrylate

HRID 1764758

Reaction equation

HRID 1764758 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH:8]1(O)[CH2:13][CH2:12]C[CH2:10][CH2:9]1.C1(NC2C=CC(C3C=CC(NC4C=CC=CC=4)=CC=3)=CC=2)C=CC=CC=1.[C-]#N.[K+].C(OC)(=O)C(C)=C.CO>>[C:1]([O:6][CH:7]1[CH2:12][CH2:13][CH2:8][CH2:9][CH2:10]1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 5

HCID 6658Methyl MethacrylateHCID 7966CyclohexanolHCID 9032Potassium CyanideHCID 68280N,N'-DiphenylbenzidineHCID 19593510Methyl methacrylate methanol

Product 1

HCID 7561Cyclohexyl methacrylate

Conditions

Temperature
75 °C

Procedure

400 g of methyl methacrylate (4 mole), 200 g of cyclohexanol (2 mole) and 0.30 g of N,N'-diphenylbenzidine (500 ppm) are added to a 1 liter round-bottomed flask. Azeotropic dehydration is accomplished by conducting air through the resulting mixture, by way of a 1 m vigreux column. After cooling of the contents of the flask to about 75° C., 3 g of potassium cyanide (0.5%) are added, and the methyl methacrylate/methanol-azeotrope is distilled-off at a temperature of 65° C. at the head of the column. The trans-esterification is completed after 3.5 hours. After cooling 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 residue of cyclohexyl methacrylate of 310 g = 85% will result.

Workup

  1. customis distilled-off at a temperature of 65° C. at the head of the column
  2. temperatureAfter cooling 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-19270db3b1b14bd99ccff77ff090aace
Source dataset
uspto-grants-1978_09
Patent number
US04117238

Linked notes

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