Acrylic Acid → Prop-2-enoic acid--6-methylheptyl prop-2-enoate (1/1)

HRID 1941012Notes

Reaction equation

HRID 1941012 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])(=[O:4])[CH:2]=[CH2:3].[C:14]([OH:18])(=[O:17])[CH:15]=[CH2:16].C1C=CC(C(OOC(C2C=CC=CC=2)=O)=O)=CC=1>CCCCCCC.C(OCC)(=O)C>[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])(=[O:4])[CH:2]=[CH2:3].[C:14]([OH:18])(=[O:17])[CH:15]=[CH2:16]

Participants

6

Reactant 3

HCID 6581Acrylic AcidHCID 7187Benzoyl PeroxideHCID 165746Isooctyl acrylate2×

Product 1

HCID 165745Prop-2-enoic acid--6-methylheptyl prop-2-enoate (1/1)

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent4×HCID 8900HeptaneSolvent

Conditions

Temperature
60 °C

Procedure

A flask equipped with an agitator, condenser, nitrogen inlet tube and an addition funnel is charged with isooctyl acrylate (72.0 g), acrylic acid (8.0 g) and ethyl acetate (78.1 g). The mixture is heated to 60° C. with medium agitation and purged with nitrogen to remove oxygen. Lucidol 75 (0.07 g, available from Elf Atochem North America) premixed in ethyl acetate (3.0 g) is added to initiate reaction. The reaction temperature is maintained at 60° C. Ethyl acetate (1.5 g) is added to the polymer solution every 30 minutes until the conversion of isooctyl acrylate to polymer reaches a minimum of 95%, typically 20-30 hours. An additional charge of Lucidol 75 (0.07 g) premixed with ethyl acetate (3.0 g) is added after 5 hours and nine hours reaction time. When 95% minimum reaction conversion is achieved, the resulting polymer solution is diluted with heptane to 20-23% solids, cooled and drained. The inherent viscosity in ethyl acetate at 0.15 g,/dl is measured at 1.7-2.0 dl/g. The inherent viscosity is measured by conventional means using a Canon-Fenske #50 viscometer in a water bath controlled at 27° C. to measure the flow time of 10 milliliters of the polymer solution. The test procedure and apparatus are described in detail in "Textbook of Polymer Science", F. W. Billmeyer, Wiley Interscience, Second Edition, 1971, pages 84 and 85.

Workup

  1. customA flask equipped with an agitator, condenser, nitrogen inlet tube and an addition funnel
  2. custompurged with nitrogen
  3. customto remove oxygen
  4. additionLucidol 75 (0.07 g, available from Elf Atochem North America) premixed in ethyl acetate (3.0 g)
  5. additionis added
  6. customreaction
  7. temperatureThe reaction temperature is maintained at 60° C
  8. customa minimum of 95%, typically 20-30 hours
  9. additionis added after 5 hours and nine hours
  10. customreaction time
  11. temperaturecooled
  12. customcontrolled at 27° C.

Sources & evidence

ORD record
ord-04a15e5605df463a8b18e3f25bc4b57b
Source dataset
uspto-grants-1997_12
Patent number
US05702720

Reaction notes

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