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Partial Deuterium Labeling of Dimethacrylate Monomers

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Summary.

Methacrylic acid-d5 was prepared in a yield of 30% with 98.6% deuterium incorporation using a two step synthesis. A solution of acetone-d6 and KCN in D2O was treated with glacial acetic acid to give the cyanohydrin of acetone-d6. The latter compound was then dehydrated in anhydrous sulfuric acid at 120°C and subsequently hydrolysed in water at 90°C to form methacrylic acid-d5. Hydrolysis of commercial nonaethyleneglycol dimethacrylate gave a mixture of ethylene glycols. These glycols were combined with methacrylic acid-d5 in the presence of p-TsOH in benzene to form nonaethyleneglycol dimethacrylate-d10 with ∼21% deuterium incorporation. Deuterated bisGMA was also prepared from methacrylic acid-d5 and diglycidyl ether of bisphenol-A.

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Authors and Affiliations

  1. CRC for polymers, 3168, Notting Hill, VIC, Australia

    Cornelis M. Moorhoff & Wayne D. Cook

  2. School of Physics and Materials Engineering, Monash University, 3800, VIC, Australia

    Wayne D. Cook

  3. CSIRO, Molecular Science, Bag 10, 3169, Clayton South, VIC, Australia

    Cornelis M. Moorhoff

Authors
  1. Cornelis M. Moorhoff
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  2. Wayne D. Cook
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Correspondence to Cornelis M. Moorhoff.

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Present address: Boron Molecular Pty Ltd, PO Box 756, Noble Park, VIC 3174, Australia

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Moorhoff, C., Cook, W. Partial Deuterium Labeling of Dimethacrylate Monomers. Monatsh. Chem. 137, 449–454 (2006). https://doi.org/10.1007/s00706-005-0453-1

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  • DOI: https://doi.org/10.1007/s00706-005-0453-1

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