1-Butanol → Butyl Acrylate

HRID 414876Notes

Reaction equation

HRID 414876 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5]C=CC=1.S(=O)(=O)(O)[OH:9].[CH2:13]([OH:17])[CH2:14][CH2:15]C>>[C:13]([O:17][CH2:5][CH2:6][CH2:1][CH3:7])(=[O:9])[CH:14]=[CH2:15]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 1140Toluene

Product 1

HCID 8846Butyl Acrylate

Conditions

Temperature
100 °C

Procedure

A typical cleavage reaction was performed by dispersing 0.1602 g GCNF-PBA3 into 100 mL toluene followed by adding 100 mL n-butanol and 5 mL concentrated sulfuric acid and refluxing the mixture at 100° C. for 9 days. Solvent was removed by rotary evaporation under reduced pressure. The residual solid was dispersed into 100 mL CHCl3 and extracted with water three times to remove any sulfuric acid. The organic dispersion was filtered through a 0.2 μm Nylon membrane and washed with CHCl3. The filtrate was distilled under reduced pressure to remove the solvent and dried in vacuum overnight at 40° C. Molecular weight and polydispersity of the cleaved PBA were measured by GPC. (Mw=31,300, Mw/Mn=1.73)

Workup

  1. customA typical cleavage reaction
  2. additionby dispersing 0.1602 g
  3. customSolvent was removed by rotary evaporation under reduced pressure
  4. additionThe residual solid was dispersed into 100 mL CHCl3
  5. extractionextracted with water three times
  6. customto remove any sulfuric acid
  7. filtrationThe organic dispersion was filtered through a 0.2 μm Nylon membrane
  8. washwashed with CHCl3
  9. distillationThe filtrate was distilled under reduced pressure
  10. customto remove the solvent
  11. customdried in vacuum overnight at 40° C

Sources & evidence

ORD record
ord-76d56f7fca0d4f9ebb5ec792baae2b6d
Source dataset
uspto-grants-2012_01
Patent number
US08088352B2

Reaction notes

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