Dimerization of Acrylic Acid

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Dimerization of Acrylic Acid

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Dimerization of Acrylic Acid

Acrylic acid (AA) spontaneously dimerizes upon standing. This reaction proceeds via an ionic mechanism and no inhibitors are known to effective for retarding or preventing it:
 
CH2=CH-COOH <———> CH2=CH-COO- + H+
Michael-type addition
CH2=CH-COO- + CH2=CH-COOH <———> CH2=CH-COO-CH2-CH-COOH ——H+—>
Acrylic Acid Dimer ("Diacrylic Acid")
CH2=CH-COO-CH2-CH2-COOH
or 2-carboxyethyl acrylate.
AA used in synthesis of acrylic esters ,FR-1025 for instance, contains oligomers- dimer, trimer and so on. We need to analyze quantitatively the 2-carboxyethyl acrylate content in AA.  2-carboxyethyl acrylate reagent vended by Aldrich contains ca 30% AA, 40% dimer and 20% trimer (area %). A preparative HPLC could be used in order to collect the dimer peak eluted from the column.
 
The question is how to obtain the pure dimer preventing its following polymerization?

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