Sodium hydroxylamine disulfonate

Note 7) followed by a mixture of 550 cc. of concentrated hydrochloric add (sp. gr. 1.19) with 400 g. of shaved ice (Note 8). The entire solution should always remain below o°, further ice being added if there is a tendency for the temperature to rise. The solution should now become acid to Congo Red paper and contain 6 or more moles of the sodium hydroxylamine disulfonate, which rapidly hydrolyzes to an acid solution of the monosulfonate. 

The reaction is reversible, but the state of equilibrium highly favors the desired products. Preparations of large quantities for synthetic work are illustrated for methyl ethyl ketoxime, cyclohexanone oxime, hept-aldoxime, and benzophenone oxime, the procedures varying somewhat with the nature of the carbonyl compound. In some instances, a readily available and cheap reagent like sodium hydroxylamine disulfonate, HON(SO,Na)j, is first prepared from sodium nitrite and sodium bisulfite and, without isolation, treated with the carbonyl compound, Hydioxylamine-O sulfonic add, Ii,NOSO,H, is still another reagent and, like sodium hydroxylamine disulfonate, is used in the absence of a base. The preparation of hydroxylamine hydrochloride is described. ... 

The reagent is prepared by oxidizing sodium hydroxylamine disulfonate with permanganate, removing the MnOi by filtration, and salting out with potassium chloride. Teuber and co-workers have studied extensively the oxidation of sub-... 

Preparation of Sodium Hydroxylamine Disulfonate 39-2. Preparation of Methyl Ethyl Ketoxime 39-3. Preparation of Phenylglyoxime... 

A classical method of preparing a standard solution of sodium hydroxylamine disulfonate is given here. Some disagreement exists in the literature as to the exact nature of this reagent. Sometimes it is referred to as sodium hydroxylamine monosulfonate [3,4]. 

In a 5-liter flask equipped with an efficient stirrer and surrounded with a large ice-salt bath is placed 4-liters of distilled water, 325 gm (3 moles) of anhydrous sodium carbonate, and 420 gm (5.8 moles) of 95 % pure sodium nitrite. The mixture is stirred and cooled. When the temperature has reached — 5°C, sulfur dioxide is passed into the solution at such a rate that the solution temperature never exceeds 0°C. With efficient cooling, the reduction is completed in approximately 4 hr. The end of the reduction is indicated by a drop in the pH of the solution to the acid side. Just before the reaction turns acid, the solution becomes slightly brown in color. The solution is approximately 1.2 Af in sodium hydroxylamine disulfonate and may be used directly for the preparation of oximes. 

In using sodium hydroxylamine disulfonate, the reagent is treated with a carbonyl compound, warmed, and cooled. Only at this point is the reaction mixture neutralized with an alkaline solution [6]. This method is suitable for the preparation of a range of carbonyl compounds. Negative results were obtained in the case of benzil and qui-none monoxime, either because the oximes are not sufficiently soluble in the reaction medium or because the oximes produced are not stable in the acidic reaction solution. 

With suitable precautions, to 1 liter of the sodium hydroxylamine disulfonate solution from Preparation 39 2 (approx. 1.2 moles) is added 72 gm (1 mole) of methyl ethyl ketone. The mixture is warmed to TO C. Then the reaction flask is wrapped with insulation and allowed to cool slowly for 12 hr. 

Preparation. Singhla reports an improved procedure for the preparation based on a patent by H.-J. Teuber. Hydroxylamine disulfonate, HON(SOaNa)2, is prepared from sodium nitrite, sodium bicarbonate, and sulfur dioxide and then oxidized with potassium permanganate with pH-control. Manganese dioxide is removed by centrifugation followed by filtration. Fremy s salt separates from the filtrate after addition of KC1 and is recrystallized from 1 N KOH. Material prepared in this way can be stored in the cold for several months. 

The cheaper sodium hydroxylamine-A,A-disulfonate may be used for preparation of oximes in place of the relatively expensive hydroxylamine. This salt is readily obtained from sodium nitrite, sodium hydrogen sulfite,... 

The yellow species formed in the reaction between sodium nitrite and thiosulfate in acidic, aqueous solution has been identified as the 5-nitrosated thiosulfate (03SSN0) , which is suggested to be formed by parallel pathways involving the nitrosonium ion and dinitrogen trioxide. The much studied reaction between nitrite and sulfite to give hydroxylamine disulfonate has received further attention and some apparent discrepancies have been clarified. For the pH range 4.5 to 7 the rate equation is given by (11). 

Sample Treatments. Blood (1 ml) and fecal samples (1 g dry-matter) were ashed on hot plates by sequential treatment with concentrated nitric acid and 30% hydrogen peroxide. The white residue of each sample was dissolved in 3-5 ml of 6 N HCl, and the final volume was brought up to 25 ml with 6 N HCl. Several 0.1 ml aliquots were transferred to test tubes, and iron concentrations were determined by a colorimetric method using the Batho-reagent (17) which contains hydroxylamine hydrochloride (10%), sodium acetate (1.5 M), and bathophenan-throline disulfonate (0.5 mM). The analytical precision of iron quantification was evaluated by measuring the iron concentrations of 13 replicates of one imenriched fecal sample. The mean of these measurements was 365.7 ug per gram of dry feces, with a relative standard deviation of 2. 8%. 

Ammonium nonoxynol-4 sulfate Ammonium nonoxynol-6 sulfate Ammonium phosphate Antimony trichloride Butylated PVP Ceteareth-4 Ceteareth-6 Ceteareth-8 Ceteareth-10 Ceteareth-11 Ceteareth-14 Ceteareth-18 Ceteareth-80 Chitosan Chloro-2-hydroxypropyl trimonium chloride Cyanamide-formaldehyde resin Dibehenyidimonium chloride Diethylene glycol Disodium arsenate Hydrogenated tallowalkonium chloride Hydroxylamine sulfate lsodeceth-6 Lauryl hydroxyethyl imidazoline Lysolecithin MEA-dodecylbenzene sulfonate Octoxynol-25 Oleth-18 Oxalic acid dihydrate PCA PEG-80 castor oil PEG lauramine PEG laurate PEG-20 laurate PEG-14 oleate PEG-5 stearate PEG-23 stearate PEG-8 tallate Potassium acid tartrate Sodium arsenate Sodium chromate Sodium dodecyl diphenyloxide disulfonate Sodium methyl oleoyl taurate Sodium methyl tallow taurate Sodium sulfate... 

Metal Chelate Addition. Metal chelates, such as ferrous ethylene-diamine-tetra-acetate (Fe(II) EDTA), enhance the absorption of NO, into aqueous solutions by reacting quickly with dissolved NO to form the complex Fe(II) EDTA NO. The coordinated NO can react with sulfite and bisulfite ions, forming hydroxylamine-N-disulfonates (HADS) and releasing the ferrous chelate to react with additional NO. When the aqueous solution is a sodium or calcium-based SO2 absorbent, the addition of ferrous chelate results in a combined NO,/SO, control process. 

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