Hydrogen Peroxide → Methyl Methacrylate

HRID 1972300Notes

Reaction equation

HRID 1972300 reaction equation
[CH3:1]C1(C)CC(CN=C=O)(C)CC(N=C=O)C1.[N-]=[C:18]=O.C(N)CN.[O:24]=[C:25]1[O:31][C@H:30]([C@H:32]([CH2:34]O)[OH:33])[C:28](O)=[C:26]1[OH:27].C(OO)(C)(C)C.OO>O.[Fe].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.C(N(CC)CC)C>[C:25]([O:31][CH3:30])(=[O:24])[C:26]([CH3:1])=[CH2:28].[CH3:18][O:27][C:26]1[CH:25]=[CH:34][C:32]([OH:33])=[CH:30][CH:28]=1

Participants

11

Reactant 6

HCID 784Hydrogen PeroxideHCID 3301EthylenediamineHCID 6410tert-Butyl hydroperoxideHCID 105034IsocyanateHCID 169132Isophorone diisocyanateHCID 54670067L-Ascorbic Acid

Product 2

HCID 6658Methyl MethacrylateHCID 90154-Methoxyphenol

Reagents, catalysts & solvents 3

HCID 3763004Ethylenediaminetetraacetic acid iron saltCatalystHCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

IPDI (262 g) was added to a reaction flask under dry air and heated to 80° C. A mixture of GALA (54.2 g), Neopentyl glycol (13.0 g), trimethylolpropane (3.05 g), a saturated polesterdiol (269 g, 1027 g/mol), methyl methacrylate (178.54 g), and p-methoxyphenol (250 mg) was prepared and added to the reactor to keep the temperature at 80° C. When the isocyanate content was 5.76%, triethylamine (23.0 g) was added and the mixture was added to water (2149 g) with stirring. To the dispersion was added 1,2-ethylene diamine (28.1 g) in water (84 g). The dispersion (850 g) was then transferred to a new reaction flask and purged with nitrogen. A mixture of diacetoneacrylamide (7.56 g), maleic anhydride (1.4 g), methyl methacrylate, (71 g), and butyl acrylate (55.5 g) was added slowly. The radical polymerization was initiated by addition of Fe-EDTA (10.5 g, 5 mM), ascorbic acid (6.3 g, 1%), and t-butylhydroperoxide (105 mg). The reaction mixture was kept at 60° C. for 1 h. Then, hydrogen peroxide was added (9.26 g, 30%) to give a dispersion of pH 6.07 and particle size Zave 88 nm.

Workup

  1. customunder dry air
  2. additionA mixture of GALA (54.2 g), Neopentyl glycol (13.0 g), trimethylolpropane (3.05 g)
  3. additionadded to the reactor
  4. customat 80° C
  5. additionwas added
  6. customThe dispersion (850 g) was then transferred to a new reaction flask
  7. custompurged with nitrogen
  8. additionA mixture of diacetoneacrylamide (7.56 g), maleic anhydride (1.4 g), methyl methacrylate, (71 g), and butyl acrylate (55.5 g)
  9. additionwas added slowly
  10. customThe radical polymerization
  11. customto give a dispersion of pH 6.07 and particle size Zave 88 nm

Sources & evidence

ORD record
ord-c879a407e16f4356833e6cc9210f1a22
Source dataset
uspto-grants-2013_04
Patent number
US08431748B2

Reaction notes

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