Diacetyl monoxime

Methyl ethyl ketone is allowed to react with n-butyl or iso-amyl nitrite in the presence of hydrochloric acid to yield diacetyl monoxime (nitrosomethyl ethyl ketone) ... 

The diacetyl monoxime condenses readily with hydroxylamine hydrochloride or sulphate with the formation of dimethylglyoxime (diacetyl dioxime) ... 

Diacetonamine hydrogen oxalate, 14,85 Diacetone alcohol, 10, no Diacetyl monoxime, 10, 22 Diallylcyanamide, 10, no Diaminodurene, 10, 41... 

The base was being prepared by distilling a mixture of hydroxylamine hydrochloride and sodium hydroxide in methanol under reduced pressure, and a violent explosion occurred towards the end of distillation [1], probably owing to an increase in pressure above 53 mbar. It explodes when heated under atmospheric pressure [2], Traces of hydroxylamine remaining after reaction with acetonitrile to form acetamide oxime caused an explosion during evaporation of solvent. Traces can be removed by treatment with diacetyl monoxime and ammoniacal nickel sulfate, forming nickel dimethylglyoxime [3], An account of an extremely violent explosion towards the end of vacuum distillation had been published previously [4], Anhydrous hydroxylamine is usually stored at 10°C to prevent internal oxidation-reduction reactions which occur at ambient temperature [5], See other REDOX REACTIONS... 

Rozet, E., Wascotte, V., Lecouturier, N., Preat, V., Dewe, W., Boulanger, B., Hubert, P. Improvement of the decision efficiency of the accuracy profile by means of a desirability function for analytical methods validation application to a diacetyl-monoxime colorimetric assay used for the... 

Brydon and Roberts- added hemolyzed blood to unhemolyzed plasma, analyzed the specimens for a variety of constituents and then compared the values with those in the unhemolyzed plasma (B28). The following procedures were considered unaffected by hemolysis (up to 1 g/100 ml hemoglobin) urea (diacetyl monoxime) carbon dioxide content (phe-nolphthalein complex) iron binding capacity cholesterol (ferric chloride) creatinine (alkaline picrate) uric acid (phosphotungstate reduction) alkaline phosphatase (4-nitrophenyl phosphate) 5 -nucleotidase (adenosine monophosphate-nickel) and tartrate-labile acid phosphatase (phenyl phosphate). In Table 2 are shown those assays where increases were observed. The hemolysis used in these studies was equivalent to that produced by the breakdown of about 15 X 10 erythrocytes. In the bromocresol green albumin method it has been reported that for every 100 mg of hemoglobin/100 ml serum, the apparent albumin concentration is increased by 100 mg/100 ml (D12). Hemolysis releases some amino acids, such as histidine, into the plasma (Alb). 

Although the major research and development effort on oxime reactivators has focused on the positively charged pyridinium ring, the poor ability of the charged oximes to cross the blood-brain barrier (BBB) has prompted several studies on noncharged aliphatic oximes in an effort to increase reactivation of OP-inhibited AChE in the central nervous system. The most smdied noncharged oximes are mono isonitrosoacetone (MINA, 44) and diacetyl monoxime (DAM, 45) " . 

Jager, B.V., and Stagg, G.N. Toxicity of diacetyl monoxime and of pyridine-2-aldoxime methiodide in man. Bull. Johns Hopkins Hosp. 102 203-211, 1958. 

Meeter, E. The effect of diacetyl monoxime (DAM) on the neuromuscular junction. Acta Physiol. Pharmacol. Neerl. 10 286-287,... 

The adverse effects of various oximes (Including diacetyl-monoxime, which was not used at Edgewood) in humans are listed In Tables 2-2 through 2-7. These tables list only significant findings. 

Diacetyl monoxime + semicarbazide, thiosemicarbazide or selenosemicarbazide [Cr(LH)L] [Cr(LH)(H20)3lCl2 (semicarbazone only) 20... 

To prepare for the colorimetric assay, a saturated semidine solution is made by mixing 200 mg of semidine (N-ph cn y 1 -p-ph cny 1 cncdiam i n c-HC1, Fluka 07920) with 10 ml of 95% ethanol, followed by dilution to 100 ml with double-distilled water (ddH20). After filtering to remove the undissolved particles, the saturated semidine solution is stable at 4 °C for up to 6 weeks. A 3% diacetyl monoxime solution is made by dissolving 3 g of 2,3-butanedione 2-oxime (Fluka 31550) in 100 ml... 

The sample, air, and saline are mixed and pumped through the dialyzer and then discarded. The recipient fluid contains the diacetyl monoxime reagent properly segmented with air. After exiting from the dialyzer, concentrated sulfuric acid containing arsenic pentoxide is added to the recipient stream, mixed, and passed through the heating bath. The color developed is then read at 480 mp in a 6-mm cell and recorded in the usual manner. 

Immediately before use, prepare the color reagent by mixing well two parts of antipyrine-H2S04 reagent with one part of diacetyl-monoxime reagent. 

Reference to Table 7.26 shows the dysprosium diacetyl monoxime complex to have seven molecules of water. This complex loses two molecules of lattice water at 160°C. At 230°C, the remaining five coordinated water molecules are lost from the complex. 

S g. (0.84 g. atom) of zinc dust, and 52.5 g. (0.46 mole) of 3-methylpentane-2,4-dione (Note 1). The contents of the flask are stirred vigorously (Note 2), and a solution of 42 g. (0.415 mole) of diacetyl monoxime in 150 ml. of glacial acetic acid is added from a separatory funnel at a rate to maintain the temperature of the mixture at 65-70°. The addition takes 1 hour. When the addition is complete, the mixture is refluxed with stirring for an additional 30 minutes. The flask is then fitted for distillation with steam under nitrogen 500 ml. of water is added and steam is introduced. Steam distillation (Note 3) is continued until no more tetramethylpyrrole comes over. This takes 1-2 hours and the distillate amounts to 1-2 1. The tetramethylpyrrole crystallizes from the steam distillate and is collected by filtration, washed with water, and dried over phosphorus pentoxide in a vacuum desiccator. There is obtained 15-18 g. of white plates, m.p. 110-111° (lit., m.p. 112°). 

The monoxime method is a colorimetric approach where urea is measured directly using diacetyl monoxime. Difficulties associated with the monoxime method include precipitate formation when the sample cools and rapid loss of color (Mulvaney and Bremer, 1979). The method also needs a higher reaction... 

Cozzi, S. (2004). A new application of the diacetyl monoxime method to the automated determination of dissolved urea in seawater. Mar. Biol. 145, 843—848. 

Mulvaney, R. L., and Bremer, J. M. (1979). A modified diacetyl monoxime method for colorimetric determination of urea in soU extracts. Commun. Soil Sci. Plant. Anal. 10, 1163—1170. 

A solution of diacetyl monoxime (1.01 g, lOmmol), D(/ )-methionine (0.89 g, 10 mmol) and 30% formalin solution (1.5 g) in ethanol (100 ml) is refluxed (3 h), then cooled and filtered. Rotary evaporation of the filtrate, treating the residue with dry acetone, again filtering, then addition of dry ether precipitates the product, which can be recrystallized from chloroform-hexane and added methanol as colourless crystals (2.35g, 96%), m.p.l78-181°C. 

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