Methanol → Butyl Methacrylate

HRID 1395285Notes

Reaction equation

HRID 1395285 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].CO[C:10]1[CH:16]=CC(O)=C[CH:11]=1.CO>C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Zr+4].C(O)CCC>[C:1]([O:6][CH2:7][CH2:11][CH2:10][CH3:16])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 6658Methyl Methacrylate2×HCID 90154-Methoxyphenol

Product 1

HCID 7354Butyl MethacrylateYield 99.2%

Reagents, catalysts & solvents 2

HCID 5463922Zirconium, tetrakis(acetylacetonato)-CatalystHCID 2631-ButanolSolvent2×

Procedure

An 74.1 g (1.0 mole) amount of n-butanol, 250.2 g (2.5 moles) of methyl methacrylate, 0.488 g (0.001 mole) of zirconium acetylacetonate and 0.28 g of hydroquinone monomethyl ether were added to a one liter flask fitted with an agitator, thermometer and fractionating tower and were heated and agitated. An azeotropic mixture of methyl methacrylate and methanol from the upper part (top) of the fractionating tower was removed at a reflux ratio of 5 to 10:1 to continuously advance the reaction. The reaction was conducted for 1.5 hours while the temperature at the top was 65° to 70° C. and the flask temperature was 104° to 130° C. The reaction showed a 99.5% conversion of n-butanol and a 99.2% yield of n-butyl methacrylate.

Workup

  1. customfitted with an agitator
  2. temperaturewere heated
  3. customwas removed at a reflux ratio of 5 to 10:1
  4. customthe reaction
  5. customwas 65° to 70° C.
  6. customwas 104° to 130° C

Sources & evidence

ORD record
ord-f865395c168049078ac25dbb9dae751f
Source dataset
uspto-grants-1980_05
Patent number
US04202990

Reaction notes

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