1,4-Dichlorobenzene → α-Methylstyrene dimer

HRID 640037Notes

Reaction equation

HRID 640037 reaction equation
[O-]O.[C:3]1([CH:9]([CH3:11])[CH3:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C(Cl)=CC=C(Cl)C=1.C(OCC1OC1)(=O)C(C)=C>>[CH3:11][C:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[CH2:10].[CH3:11][C:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[CH2:10]

Participants

4

Reactant 3

HCID 46851,4-DichlorobenzeneHCID 7837Glycidyl methacrylateHCID 53627471Cumen hydroperoxide2×

Product 1

HCID 22521α-Methylstyrene dimer

Conditions

Temperature
900 °C

Procedure

A high temperature initiator, cumene hydroperoxide, was included in this run to drive the polymerization further towards completion and to reduce residual monomer. The flask was charged with brominated styrene monomer (10002.6), dichlorobenzene (497 g), glycidyl methacrylate (5.13 g, 0.0360 mol), 2,4-diphenyl-4-methyl-l-pentane (20.26 g, 0.08571 mol), VAZO-52™ azo type initiator (1.05 g, 4.22 mmol) and cumene hydroperoxide (1.06 g, 6.96 mmol). In one embodiment, the monomer/polymerization initiator blend may be reacted under conditions effective to polymerize at least about 80% of the monomers in a time of between about 1 minute and about 20 minutes. The solution was then heated to about 900° C. until exotherm. Peak temperature reached was 163° C. after which the mixture was heated the mixture was heated to 190° C. over 5-10 mm and held at 190° C. for 40-45 mm. Heating was halted; the solution (1513.7 g) was transferred to a 2-liter bottle, and cooled to room temperature. The material was split into four parts. Each part was precipitated into a 5-liter flask of 3400 mL acetone and 400 mL methanol. The precipitate was filtered over frit, dried at ambient temperature for about 14 h and oven dried at 110° C. for 8 h. A white powder (883 g) was isolated.

Workup

  1. customthe polymerization further towards completion
  2. customIn one embodiment, the monomer/polymerization initiator blend may be reacted under conditions effective
  3. customreached was 163° C.
  4. temperaturewas heated the mixture
  5. temperaturewas heated to 190° C. over 5-10 mm
  6. customheld at 190° C. for 40-45 mm
  7. temperatureHeating
  8. temperaturecooled to room temperature
  9. customThe material was split into four parts
  10. customEach part was precipitated into a 5-liter flask of 3400 mL acetone and 400 mL methanol
  11. filtrationThe precipitate was filtered over frit
  12. customdried at ambient temperature for about 14 h
  13. customoven dried at 110° C. for 8 h

Sources & evidence

ORD record
ord-ba32ac6c40284fb99ae842ba46899513
Source dataset
uspto-grants-2010_04
Patent number
US07691954B2

Reaction notes

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