Acetic Anhydride → Sebacic Acid

HRID 2352747Notes

Reaction equation

HRID 2352747 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/C=C\CCCCCCCC.C(O)(=O)CCCCCCC/C=C\C/C=C\CCCCC.C([O:44][C:45](=[O:47])[CH3:46])(=O)C>>[C:45]([OH:44])(=[O:47])[CH2:46][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:20])=[O:19]

Participants

4

Procedure

The prepolymer of sebacic acid (SA) was prepared from the purified diacid monomer by refluxing in excess acetic anhydride for 30 minutes and evaporating the solvent to dryness. The hot clear viscous residue was dissolved in an equal volume of dichloromethane and precipitated in a mixture of ether/petroleum ether (1:1 v/v). The white precipitate was collected by filtration and dried by vacuum at room temperature. Acetyl terminated fatty acid anhydrides were prepared by dissolving the acids in acetic anhydride (120° C., 1:5 w/v) and refluxing for 20 min. Acetate anhydrides of oleic acid, linoleic acid and other cis-double bond containing fatty acid were prepared by refluxing the fatty acid in acetic anhydride for 20 min. and evaporating the solvent to dryness to obtain a liquid. Mixed prepolymers of diacids with the monoacid terminals were prepared similarly.

Workup

  1. customevaporating the solvent to dryness
  2. dissolutionThe hot clear viscous residue was dissolved in an equal volume of dichloromethane
  3. customprecipitated in a mixture of ether/petroleum ether (1:1 v/v)
  4. filtrationThe white precipitate was collected by filtration
  5. customdried by vacuum at room temperature
  6. customAcetyl terminated fatty acid anhydrides
  7. customwere prepared
  8. temperaturerefluxing for 20 min
  9. customwere prepared
  10. customevaporating the solvent to dryness
  11. customto obtain a liquid

Sources & evidence

ORD record
ord-a0d41e915711416f8c03b6f1830fb910
Source dataset
uspto-grants-2010_07
Patent number
US07749539B2

Reaction notes

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