Sulfuric Acid → Butyl Acrylate

HRID 2394933Notes

Reaction equation

HRID 2394933 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].S(=O)(=O)(O)O.CO[C:13]1[CH:19]=CC(O)=[CH:15][CH:14]=1>C(O)CCC>[C:1]([O:5][CH2:19][CH2:13][CH2:14][CH3:15])(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6581Acrylic AcidHCID 90154-Methoxyphenol

Product 1

HCID 8846Butyl Acrylate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent4×

Procedure

For comparison, a known esterification process was carried out using only one reaction region. In this Comparative Example, 4 mol/h of acrylic acid, 4 mol/h of fresh butanol and 1.6 mol/h of recycled butanol (distillate from the butanol recovery) were fed to a circulation evaporator (2.5 l, level of fill 2 l). The residence time was 2.5 h. The esterification was carried out in the presence of 9.7% by weight (based on the reaction mixture) of sulfuric acid at 126° C. The reactor was connected to a bubble-cap column (30 trays), which was stabilized with 15 ml/h of hydroquinone monomethyl ether (MeHQ) in butanol. Butyl acrylate formed was removed via the top by adding 340 ml/h of water as a reflux (azeotropic entraining agent) to the column. In addition, 175 ml/h of organic reflux were added to the column in order to suppress the acrylic acid.

Workup

  1. customone reaction region
  2. customat 126° C

Sources & evidence

ORD record
ord-fc51c4a9161f48b9bfc4e03a9e1b30a4
Source dataset
uspto-grants-1998_09
Patent number
US05811574

Reaction notes

Loading…