Methacrylic anhydride → Methacrylic Acid

HRID 1816081Notes

Reaction equation

HRID 1816081 reaction equation
[C:1]([O:6][C:7](=O)[C:8](C)=C)(=[O:5])[C:2]([CH3:4])=[CH2:3].OC(=C)C([O-])=O>>[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

4

Reactant 2

HCID 12974Methacrylic anhydride2×HCID 178473601HCID 178473601, compound

Product 2

HCID 4093Methacrylic AcidHCID 7343Ethyl Methacrylate

Procedure

It is just as possible to use an excess of methacrylic anhydride, for example 20 mol %. In this case, after the reaction of the hydroxyacrylate (II) is as complete as possible, the excess methacrylic anhydride is destroyed by adding a low molecular weight alcohol such as methanol, ethanol, or isopropanol. This method is particularly recommended with longer-chained compounds (n=3-100). The excess methacrylic anhydride guarantees the most complete possible conversion of the hydroxy compound; the subsequent reaction of the methacrylic anhydride to give ethyl methacrylate and methacrylic acid, for example, ensures easier separation of these components with lower boiling points than methacrylic anhydride.

Workup

  1. customis destroyed
  2. additionby adding a low molecular weight alcohol such as methanol, ethanol, or isopropanol
  3. customthe subsequent reaction of the methacrylic anhydride

Sources & evidence

ORD record
ord-6e3c636e6f1c475e867cf99c7cef1fe1
Source dataset
uspto-grants-2005_04
Patent number
US06881858B2

Reaction notes

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