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

HRID 2287920Notes

Reaction equation

HRID 2287920 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 was charged with isooctyl acrylate (72.0 g), acrylic acid (8.0 g) and ethyl acetate (78.1 g). The mixture was 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) was added to initiate reaction. The reaction temperature was maintained at 60° C. Ethyl acetate (1.5 g) was added to the polymer solution every 30 minutes until the conversion of isooctyl acrylate to polymer reached a minimum of 95%, typically 20-30 hours. An additional charge of Lucidol 75 (0.07 g) premixed with ethyl acetate (3.0 g) was added after 5 hours and nine hours reaction time. When 95% minimum reaction conversion was achieved, the resulting polymer solution was diluted with heptane to 20-23%, solids, cooled and drained. The inherent viscosity in ethyl acetate at 0.15 g/dl was measured at 1.7-2.0 dl/g. The inherent viscosity was 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. additionwas added
  6. customreaction
  7. temperatureThe reaction temperature was maintained at 60° C
  8. customa minimum of 95%, typically 20-30 hours
  9. additionwas added after 5 hours and nine hours
  10. customreaction time
  11. temperaturecooled
  12. customcontrolled at 27° C.

Sources & evidence

ORD record
ord-1937db5e09554444b4d9e29811224a4f
Source dataset
uspto-grants-2000_07
Patent number
US06086911

Reaction notes

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