Partial Deuterium Labeling of Dimethacrylate Monomers |
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| Authors: | Cornelis M Moorhoff Wayne D Cook |
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| Institution: | (1) CRC for polymers, 3168 Notting Hill, VIC, Australia;(2) School of Physics and Materials Engineering, Monash University, 3800, VIC, Australia;(3) CSIRO, Molecular Science, Bag 10, 3169 Clayton South, VIC, Australia |
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| Abstract: | 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.
Present address: Boron Molecular Pty Ltd, PO Box 756, Noble Park, VIC 3174, Australia |
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| Keywords: | , Methacrylic acid-d5, SANS, Nonaethylene glycol dimethacrylate, bisGMA-nonaethyleneglycol dimethacrylate-d10, bisGMA-d10, |
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