1-Butanol → Butyl Acrylate

HRID 2248071Notes

Reaction equation

HRID 2248071 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[C:6](OC)(=[O:9])[CH:7]=[CH2:8].COC1C=CC(O)=CC=1.C1C2NC3C(=CC=CC=3)SC=2C=CC=1.C(N(CC)O)C>CO>[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])(=[O:9])[CH:7]=[CH2:8]

Participants

7

Reactant 5

HCID 2631-ButanolHCID 7108PhenothiazineHCID 7294Methyl Acrylate2×HCID 90154-MethoxyphenolHCID 19463Diethylhydroxylamine

Product 1

HCID 8846Butyl Acrylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

One hundred forty eight grams (2.0 moles) of n-butanol, 516 g (6.0 moles) methyl acrylate, 1.15 g hafnium acetylacetonate, 0.10 g of MEHQ inhibitor, 0.1 g phenothiazine, and 0.10 g diethylhydroxylamine were added to a 2 liter flask equipped as described in Example 3. The solution was heated at reflux (atmospheric pressure) while an azeotropic mixture of methyl acrylate and methanol was removed from the top of the column. The reaction was continued in this manner for 2 hours while the temperature at the top of the column was 62°-64° C. and the temperature in the reaction vessel was 82°-97° C. GLC analysis of the reaction mixture showed >99% conversion of the n-butanol to butyl acrylate.

Workup

  1. customequipped
  2. temperatureThe solution was heated
  3. temperatureat reflux (atmospheric pressure)
  4. customwas removed from the top of the column
  5. customwas 62°-64° C.
  6. customwas 82°-97° C

Sources & evidence

ORD record
ord-371ed2d4996d4413989b57804232e1b0
Source dataset
uspto-grants-1991_08
Patent number
US05037978

Reaction notes

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