Acrylic Acid → HCID 131724291, compound

HRID 2119765Notes

Reaction equation

HRID 2119765 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:9][C:10]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH2:11].[C:17]([O:21][CH2:22][CH2:23][CH2:24][OH:25])(=[O:20])[CH:18]=[CH2:19].[C:26]([O:31][CH2:32][CH2:33][CH2:34][CH3:35])(=[O:30])[C:27]([CH3:29])=[CH2:28].[C:36]([OH:40])(=[O:39])[CH:37]=[CH2:38].[C:41]([O:45][CH2:46][CH2:47][CH2:48][CH3:49])(=[O:44])[CH:42]=[CH2:43]>C(OCCCC)(=O)C>[CH3:11][C:10]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH2:9].[C:17]([O:21][CH2:22][CH2:23][CH2:24][OH:25])(=[O:20])[CH:18]=[CH2:19].[C:26]([O:31][CH2:32][CH2:33][CH2:34][CH3:35])(=[O:30])[C:27]([CH3:29])=[CH2:28].[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:36]([OH:40])(=[O:39])[CH:37]=[CH2:38].[C:41]([O:45][CH2:46][CH2:47][CH2:48][CH3:49])(=[O:44])[CH:42]=[CH2:43]

Participants

8

Reactant 6

HCID 6581Acrylic AcidHCID 7354Butyl MethacrylateHCID 7501Styrene2×HCID 78682,4,4-Trimethyl-1-penteneHCID 8846Butyl AcrylateHCID 331012-Propenoic acid, 3-hydroxypropyl ester

Product 1

HCID 131724291HCID 131724291, compound

Reagents, catalysts & solvents 1

HCID 31272Butyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

Charge 1 was added to a 4-liter stirred stainless steel pressure reactor. The reactor was then pressurized with nitrogen providing a 5 psig pad on the reactor. The agitation on the reactor was set at 500 rpm and the reactor temperature was adjusted to 150° C. Charge 2 was added to the reactor at addition rate of 52 grams/hour over 2.5 hours. After 15 minutes Charge 3 was added to reactor at the addition rate 500 grams/hour over 2 hours. During the monomer addition the temperature was maintained at 150° C. at 100 PSI. After charge 2 and charge 3 were in the reactor, the reaction mixture was held for 2 hours. The reactor was then cooled to 25° C., and vented. GC analysis of the reaction mixture showed that all acrylates, methacrylates and styrene were reacted. The reaction mixture was transferred to a 3 L flask, and was vacuum-stripped at 130° C. The final solids of the resulting polymer was determined by adding 200 grams of butyl acetate to the polymer mixture. The solids were measured at 82.2% at 110° C. for one hour. The copolymer had Mn=1560 and Mw/Mn=2.2. The 13C NMR spectrum is consistent with a molar copolymer composition of 20.4% Diisobutylene, 36.3% Hydroxypropyl acrylate, 16.1% Butyl methacrylate, 8.1% Styrene, 2.4% Acrylic acid, and 17.6% Butyl acrylate.

Workup

  1. additionCharge 1
  2. additionwas added to a 4-liter
  3. customwas adjusted to 150° C
  4. additionCharge 2
  5. additionwas added to the reactor at addition rate of 52 grams/hour over 2.5 hours
  6. additionAfter 15 minutes Charge 3
  7. additionwas added to reactor at the addition rate 500 grams/hour over 2 hours
  8. additionDuring the monomer addition the temperature
  9. additionAfter charge 2
  10. additioncharge 3
  11. temperatureThe reactor was then cooled to 25° C.
  12. customwere reacted
  13. customThe reaction mixture was transferred to a 3 L flask
  14. customwas vacuum-stripped at 130° C
  15. waitThe solids were measured at 82.2% at 110° C. for one hour

Sources & evidence

ORD record
ord-3bb6efbc73ca47609198bff4aaf791a1
Source dataset
uspto-grants-2004_02
Patent number
US06686432B2

Reaction notes

Loading…