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Methacrylic Acid → HCID 20273141, compound

HRID 616709
Notes
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Reaction equation

HRID 616709 reaction equation
[C:1]([O-:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:7]([Sn+:11]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH3:10].C(O)(=O)C(C)=C.CCCC[Sn](CCCC)CCCC.[OH].[C:40]([O:45][CH3:46])(=[O:44])[C:41]([CH3:43])=[CH2:42].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[C:1]([O-:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:16]([Sn+:11]([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:12][CH2:13][CH2:14][CH3:15])[CH2:17][CH2:18][CH3:19].[C:40]([O:45][CH3:46])(=[O:44])[C:41]([CH3:43])=[CH2:42]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 4093Methacrylic AcidHCID 6658Methyl MethacrylateHCID 7187Benzoyl PeroxideHCID 6336496TributylstannyloxyHCID 21946344Tributyl tin methacrylate2×

Product 1

HCID 20273141HCID 20273141, compound

Reagents, catalysts & solvents

1
HCID 241BenzeneSolvent2×

Procedure

The monomers of P30 were first synthesized. Tri-n-butyltin methacrylate prepared according to Montermoso et al U.S. Pat. No. 3,016,369. Uninhibited methacrylic acid (37.8 ml, 0.444 mole) and tri-n-butyltin oxide (112.5 ml, 0.222 mole) were reacted in 200 of dischloromethane. Upon refluxing for 1 hour, 4.5 ml of water were collected azeotropically. After the reaction was completed, the solvent was evaporated under vacuum. The product ester was a yellow transparent liquid. The monomers were then copolymerized in a 1-liter, 3-necked flask equipped with a reflux condenser, a thermometer, such that it read the temperature of the reactants, and a mechanical stirrer. Tri-n-butyltin methacrylate (50 grams, 0.140 mole), uninhibited methyl methacrylate (50 grams, 0.580 mole), and benzoyl peroxide (0.5% by weight) were reacted in 200 ml of benzene. The solution polymerization was allowed to reflux for 8 hours. The resultant polymer was clear and could be cast as a film from the benzene solution.

Workup

  1. customThe monomers of P30 were first synthesized
  2. temperatureUpon refluxing for 1 hour
  3. custom4.5 ml of water were collected azeotropically
  4. customthe solvent was evaporated under vacuum
  5. customcopolymerized in a 1-liter, 3-necked flask
  6. customequipped with a reflux condenser
  7. customThe solution polymerization
  8. temperatureto reflux for 8 hours

Sources & evidence

ORD record
ord-700fc3a3c4424fba9af17898bbf63163
Source dataset
uspto-grants-1978_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04075319

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes