REACTIVE SKIN DECONTAMINANT REACTIVITY STUDIES: THE EFFECT OF O-ACETYL 2,3-BUTANEDIONE MONOOXIME ON THE STABILITY OF 2,3-BUTANEDIONE MONOOXIMATE

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Authors
  1. Clewley, R.G.
  2. Purdon, J.G.
  3. Chenier, C.L.
Corporate Authors
Defence Research Establishment Suffield, Ralston ALTA (CAN)
Abstract
The reaction of acetic anhydride with 2,3-butanedione monooximate, to generate in situ O-acetyl 2,3-butanedione monooxime, has been examined in four solvents. In water, the initially formed O-acetyl oxime undergoes a general-base catalysed Beckmann rearrangement; if present in excess, one equivalent of oximate is consumed by every equivalent of acetic anhydride. In acetonitrile, O-acetyl 2,3-butanedione monooxime catalyses the disproportionation of 2,3-butanedione monooximate. In RSD formulations employing polyethylene glycol monomethyl ether of average molecular weight 550 (MPEG-550) and 10% w/w water/MPEG-550 less than one equivalent of oximate is consumed by every equivalent of acetic anhydride. While O-acetyl 2,3-butanedione monooxime catalysed disproportionation of 2,3-butanedione monooximate does not occur in the medium employed for the RSD, it may place a significant constraint on the use of this nucleophile in decontaminants which employ aprotic media.
Report Number
DRES-M-1382 — Memorandum
Date of publication
15 Mar 1992
Number of Pages
17
DSTKIM No
92-01887
CANDIS No
104772
Format(s):
Document Image stored on Optical Disk;Originator's fiche received by DSIS

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