Water → Methacrylate maleate

HRID 464475Notes

Reaction equation

HRID 464475 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.C([O:12]OC(C)(C)C)(C)(C)C.[C:18]([OH:23])(=[O:22])[C:19]([CH3:21])=[CH2:20].O>C(C(C)=O)C(C)C>[C:18]([O-:23])(=[O:22])[C:19]([CH3:21])=[CH2:20].[C:1]([O-:6])(=[O:7])/[CH:2]=[CH:3]\[C:4]([O-:12])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 4093Methacrylic Acid2×HCID 7923Maleic AnhydrideHCID 8033Di-tert-butyl peroxide

Product 1

HCID 86738935Methacrylate maleate

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent2×

Conditions

Temperature
115 °C

Procedure

In a 3-neck, 300 ml round bottom flask equipped with reflux condenser, nitrogen inlet, mechanical stirrer and pressure-equalizing dropping funnel were combined 58.8 g (0.60 mole) maleic anhydride, 14.6 g di-t-butyl peroxide, 115 g methyl isobutyl ketone and 3.4 g (0.040 mole) glacial methacrylic acid. The system was purged with nitrogen and then heated to reflux under a static positive nitrogen pressure. A small amount of solids momentarily precipitated and then redissolved at about 100° C. When the reaction mixture reached reflux (about 115° C.), the remaining 31.0 g (0.36 mole) methacrylic acid in 60 g of methyl isobutyl ketone was added continuously over a 3-hour period. The reaction solution was refluxed for 15 minutes following the addition, 150 g of water was then added, and the ketone-water mixture refluxed for an additional hour. The isolation procedure of Example 4 was followed to produce a 57 weight percent aqueous solution of homogeneous hydrolyzed methacrylate/maleate copolymer of weight average molecular weight of 3390 and number average molecular weight of 610 in 98 weight percent yield.

Workup

  1. customIn a 3-neck, 300 ml round bottom flask equipped
  2. temperaturewith reflux condenser, nitrogen inlet, mechanical stirrer
  3. customThe system was purged with nitrogen
  4. temperatureheated
  5. temperatureto reflux under a static positive nitrogen pressure
  6. customA small amount of solids momentarily precipitated
  7. dissolutionredissolved at about 100° C
  8. temperatureThe reaction solution was refluxed for 15 minutes
  9. additionwas then added

Sources & evidence

ORD record
ord-ace20cb2f06242b5907b7878daeb5c5d
Source dataset
uspto-grants-1985_10
Patent number
US04547559

Reaction notes

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