Methacrylic Acid → HCID 18373619, compound

HRID 2279695Notes

Reaction equation

HRID 2279695 reaction equation
[C:1]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:14]([OH:19])(=[O:18])[C:15]([CH3:17])=[CH2:16].[C:20]([O:25][CH3:26])(=[O:24])[C:21]([CH3:23])=[CH2:22]>C(C(C)=O)C.N(C(C)(C)C(OC)=O)=NC(C)(C)C(OC)=O>[C:1]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:14]([OH:19])(=[O:18])[C:15]([CH3:17])=[CH2:16].[C:20]([O:25][CH3:26])(=[O:24])[C:21]([CH3:23])=[CH2:22]

Participants

6

Reactant 3

HCID 4093Methacrylic AcidHCID 6658Methyl MethacrylateHCID 17236Benzyl methacrylate

Product 1

HCID 18373619HCID 18373619, compoundYield 228%

Reagents, catalysts & solvents 2

HCID 757631,1'-Dimethyl 2,2'-(1,2-diazenediyl)bis(2-methylpropanoate)Catalyst2×HCID 6569Methyl Ethyl KetoneSolvent3×

Conditions

Temperature
72 °C

Procedure

88 g of methyl ethyl ketone were added to a 1000 mL three-necked flask equipped with a stirrer and a condenser tube, and heated to 72° C. under a nitrogen atmosphere. To this, a solution obtained by dissolving 0.85 g of dimethyl 2,2′-azobis(isobutyrate), 60 g of benzyl methacrylate, 10 g of methacrylic acid, and 30 g of methyl methacrylate in 50 g of methyl ethyl ketone was added dropwise over 3 hours. After the dropwise addition was completed, the mixture was allowed to react for an additional one hour, and then a solution obtained by dissolving 0.42 g of dimethyl 2,2′-azobis(isobutyrate) in 2 g of methyl ethyl ketone was added thereto. The temperature was elevated to 78° C., and the mixture was heated for 4 hours. The resulting reaction liquid was reprecipitated twice with an excess of hexane, and the separated resin was dried. In this way, 96 g of a benzyl methacrylate/methacrylic acid/methyl methacrylate copolymer (=60/10/30 [mass ratio]) as a water-insoluble polymer dispersant P-1 were obtained (see, the following formula).

Workup

  1. customequipped with a stirrer and a condenser tube
  2. customTo this, a solution obtained
  3. additionwas added dropwise over 3 hours
  4. additionAfter the dropwise addition
  5. customto react for an additional one hour
  6. customa solution obtained
  7. additionwas added
  8. customwas elevated to 78° C.
  9. temperaturethe mixture was heated for 4 hours
  10. customThe resulting reaction liquid
  11. customwas reprecipitated twice with an excess of hexane
  12. customthe separated resin was dried

Sources & evidence

ORD record
ord-dbbb0ee1f1df42d5a882adba0429cf38
Source dataset
uspto-grants-2015_09
Patent number
US09133359B2

Reaction notes

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