1,4-Dichlorobenzene → α-Methylstyrene dimer

HRID 640035Notes

Reaction equation

HRID 640035 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.[C:30]1([C:36]([CH2:38]C(C2C=CC=CC=2)(C)C)=[CH2:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH3:11][C:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[CH2:10].[CH3:38][C:36]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[CH2:37]

Participants

5

Reactant 4

HCID 46851,4-DichlorobenzeneHCID 7837Glycidyl methacrylateHCID 807151,1'-(1,1-Dimethyl-3-methylene-1,3-propanediyl)bisbenzeneHCID 53627471Cumen hydroperoxide2×

Product 1

HCID 22521α-Methylstyrene dimer

Conditions

Temperature
90 °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 (1002.6), dichlorobenzene (497 g), glycidyl methacrylate (5.13 g, 0.0360 mol), 2,4-diphenyl-4-methyl-1-pentene (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). The solution was then heated to about 90° C. until exotherm. Peak temperature reached was 163° C. after which the mixture was heated to 190° C. over 5-10 min and held at 190° C. for 40-45 min. 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. customreached was 163° C.
  3. temperaturewas heated to 190° C. over 5-10 min
  4. temperatureHeating
  5. temperaturecooled to room temperature
  6. customThe material was split into four parts
  7. customEach part was precipitated into a 5-liter flask of 3400 mL acetone and 400 mL methanol
  8. filtrationThe precipitate was filtered over frit
  9. customdried at ambient temperature for about 14 h
  10. customoven dried at 110° C. for 8 h

Sources & evidence

ORD record
ord-55d192e28a5348398f8266c18f8abc84
Source dataset
uspto-grants-2010_04
Patent number
US07691947B2

Reaction notes

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