Azobisisobutyronitrile → HCID 86587525, compound

HRID 1276014Notes

Reaction equation

HRID 1276014 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:9]=[CH2:10].[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[CH:16]=[CH2:17].[C:24]([O:28][CH3:29])(=[O:27])[CH:25]=[CH2:26].[C:30]([OH:34])(=[O:33])[CH:31]=[CH2:32].N(C(C)(C)C#N)=NC(C)(C)C#N>O1CCCC1>[C:4]1(=[O:5])[O:6][C:1](=[O:7])[CH:2]=[CH:3]1.[CH2:8]([Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:9]=[CH2:10].[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[CH:16]=[CH2:17].[C:24]([O:28][CH3:29])(=[O:27])[CH:25]=[CH2:26].[C:30]([OH:34])(=[O:33])[CH:31]=[CH2:32]

Participants

8

Reactant 6

HCID 6547AzobisisobutyronitrileHCID 6581Acrylic AcidHCID 7294Methyl AcrylateHCID 7923Maleic Anhydride2×HCID 15458tert-Butyl acrylateHCID 69808Allyltrimethylsilane

Product 1

HCID 86587525HCID 86587525, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
64 °C

Procedure

In a 250 ml, round bottom flask equipped with a reflux condenser and a gas inlet was combined maleic anhydride (8.76 g, 0.089 mol) and tetrahydrofuran (30 ml). The mixture was stirred under a N2 atmosphere until all the maleic anhydride was dissolved. To this solution was added allyltrimethylsilane (10.23 g, 0.089 mol), t-butyl acrylate (8.82 g, 0.069 mol), methyl acrylate (1.20 g, 0.014 mol), acrylic acid (1.0 g, 0.014 mol) and 2,2'-azobisisobutyronitrile (0.146 g, 0.9 mmol). The mixture was heated to 64° C., and the mixture was stirred at this temperature for 18 h. The reaction mixture was cooled to room temperature and added dropwise to hexanes (500 ml). The precipitate was filtered, and the solid was dried in vacuo (12 mm Hg) at room temperature for 1 h. The solid was dissolved in tetrahydrofuran (50 ml), and the solution was added dropwise to hexanes (500 ml). The precipitate was filtered, and the solid was dried in vacuo (0.2 mm Hg) 50° C. for 16 h giving poly(maleic anhydride-allyltrimethylsilane-t-butyl acrylate-methyl acrylate-acrylic acid) (23.9 g, 79.7%) as a white powder. 1H NMR (d6-acetone, 250 MHz): 30.0 mole % maleic anhydride, 30.0 mole % allyltrimethylsilane, 25.4 mole % t-butyl acrylate, 14.8 mol % methyl acrylate. GPC V software, Phenogel-10, 7.8×250 mm column: 10-4A, 500A & 50A, THF eluent]): Mw =14, 921; Polydispersity=2.51; Rmin =2.5 Å/sec.

Workup

  1. customIn a 250 ml, round bottom flask equipped with a reflux condenser and a gas inlet
  2. dissolutionwas dissolved
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationThe precipitate was filtered
  5. customthe solid was dried in vacuo (12 mm Hg) at room temperature for 1 h
  6. dissolutionThe solid was dissolved in tetrahydrofuran (50 ml)
  7. additionthe solution was added dropwise to hexanes (500 ml)
  8. filtrationThe precipitate was filtered
  9. customthe solid was dried in vacuo (0.2 mm Hg) 50° C. for 16 h

Sources & evidence

ORD record
ord-8546be89373443d9a322c5a80707b84d
Source dataset
uspto-grants-2000_12
Patent number
US06165682

Reaction notes

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