Azobisisobutyronitrile → Methyl methacrylate linoleyl methacrylate methacrylic acid

HRID 1076454Notes

Reaction equation

HRID 1076454 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:8](Cl)(=[O:12])[C:9]([CH3:11])=[CH2:10].N(C(C)(C)C#N)=NC(C)(C)C#N.[CH2:26]([OH:44])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]/[CH:34]=[CH:35]\[CH2:36]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OC)(=O)CCCCCCC/C=C\C/C=C\CCCCC>C1C=CC=CC=1>[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:8]([O:44][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]/[CH:34]=[CH:35]\[CH2:36]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])(=[O:12])[C:9]([CH3:11])=[CH2:10].[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

8

Reactant 6

HCID 6547AzobisisobutyronitrileHCID 6658Methyl MethacrylateHCID 13528Methacryloyl chlorideHCID 5284421Methyl linoleateHCID 5365682Linoleyl alcoholHCID 21226445Aluminium lithium hydride

Product 1

HCID 86733418Methyl methacrylate linoleyl methacrylate methacrylic acid

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 90 parts of methyl methacrylate, 10 parts of methacrylyl chloride, and 2 parts of azobisisobutyronitrile was added, over a period of 3 hours, to 250 parts of dry benzene maintained at reflux under a nitrogen atmosphere. The mixture was refluxed for an additional 14 hours, cooled to 20°C and then stirred for 1 hour with 19 parts of linoleyl alcohol, prepared by lithium aluminium hydride reduction of technical methyl linoleate. The mixture was washed with water then evaporated in vacuo to yield a methyl methacrylate/linoleyl methacrylate/methacrylic acid copolymer. 10 parts of the copolymer was dissolved in 20 parts of toluol and then mixed with 100 parts of a commercial silica-alumina coated rutile titania pigment, and dried in vacuo at 50°C. The resultant solid was finely ground, then oxidised by air in a fluidised bed at 50°C for 24 hours to yield a product containing 0.02m. equiv./g of peroxidic species. When incorporated in polyethylene by the method of Example 1, a polyethylene of improved toughness was obtained.

Workup

  1. temperaturemaintained
  2. temperatureat reflux under a nitrogen atmosphere
  3. temperatureThe mixture was refluxed for an additional 14 hours
  4. washThe mixture was washed with water
  5. customthen evaporated in vacuo

Sources & evidence

ORD record
ord-75da238e3f634f2a9c3cce95704c38b6
Source dataset
uspto-grants-1976_05
Patent number
US03957526

Reaction notes

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