Methyl-red

In a 250 ml. flask place 75 ml, of water, 24 g. (20 ml.) of concentrated hydrochloric acid and 14g. (13-7 ml.) of aniline. Shake vigorously (1) and then add 50 g. of crushed ice. Rim in a solution of 5-2 g. of so um nitrite in 12 ml. of water, with constant shaking, during a period of 5-10 minutes. Allow to stand with frequent shaking (1) for 15 minutes, and add a solution of 21 0 g. of crystallised sodium acetate in 40 ml. of water during 5 minutes. A yellow precipitate of diazoaminobenzene begins to form immediately allow to stand with frequent shaking for 45 minutes and do not allow the temperature to rise above 20° (add ice. 

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Titration. The solution of ammonia absorbed in saturated boric acid may now be titrated as an alkali directly with 0 025 A.HCl (best obtained by dilution of commercially available standard A.HCl in a graduated flask). Three drops of indicator (mixed methyl-red/methyl-ene-blue being most satisfactory) are added to the liquid in the receiver and the 0 025 A.HCl run in from an accurate burette. 

The solution in A is now treated with mercuric chloride and methyl-red, and then titrated with Ml 10 HCl until its colour matches that of the solution in B. The difference in the volume of HCl run in from the burettes A and Bi is a measure of the amount of urea present. 

Meanwhile add 4 drops of methyl-red and 1 ml. of 10% ammonium chloride solution to B. The colour will normally be yellow if so, add A//10 HCl from Bh drop by drop, until a red colour is just obtained. 

I) The solution may be analysed approximately as follows. Remove 25 ml. of the ether solution and run it into 25 ml. of water contained in a small separatory funnel shake. Run off the aqueous layer into a 250 ml. conical flask and extract the ether layer with two 25 ml. portions of water. Titrate the combined aqueous extracts with 0 - IN sulphuric acid, using methyl red as indicator. 

The valuable indicator methyl red (o-carboxybenzene-azo-dimethylaniline) is obtained by coupling diazotised anthranilic acid with dimethylaniline ... 

The sodium salt of methyl red may be prepared by dissolving the crude product in an equal weight of 35 per cent, sodium hydroxide which has been diluted to 350 ml., hitoring, and evaporating under diminished pressure (Fig. II, 37, I). The resulting sodium salt forms orange leaflets. This water-soluble product is very convenient for use as an indicator. Incidentally, the toluene extraction is avoided. 

Methyl red may also be recrystallised from glacial acetic acid. 

Meihylamine hydrochloride method. Place 100 g. of 24 per cent, methyl-amine solution (6) in a tared 500 ml. flask and add concentrated hydrochloric acid (about 78 ml.) until the solution is acid to methyl red. Add water to bring the total weight to 250 g., then introduce lSO g. of urea, and boil the solution gently under reflux for two and three-quarter hours, and then vigorously for 15 minutes. Cool the solution to room temperature, dissolve 55 g. of 95 per cent, sodium nitrite in it, and cool to 0°. Prepare a mixture of 300 g. of crushed ice and 50 g. of concentrated sulphuric acid in a 1500 ml. beaker surrounded by a bath of ice and salt, and add the cold methylurea - nitrite solution slowly and with mechanical stirring and at such a rate (about 1 hour) that the temperature does not rise above 0°. It is recommended that the stem of the funnel containii the methylurea - nitrite solution dip below the surface of the acid solution. The nitrosomethylurea rises to the surface as a crystalline foamy precipitate. Filter at once at the pump, and drain well. Stir the crystals into a paste with about 50 ml. of cold water, suck as dry as possible, and dry in a vacuum desiccator to constant weight. The yield is 55 g. (5). 

The procedures for the preparation of a number of azo dyestuffs are described in Sections IV, 76-1V,82 these include the indicators methyl orange and methyl red. Experimental details for the preparation of other typical dyestuffs and indicators are given in the following pages. 

Grote s reagent is useful for the determination of 2-aminothiazoie in blood and wine (145), This thiazole may be extracted from its aqueous solution and then titrated in nonaqueous medium (MeOH) with HCIO4 in the presence of a mixed methyl red-methylene blue indicator (146). 

Alkaline arsenite, O.IA As(lll) to As(V). Dissolve 4.9460 g of primary standard grade AsjOj in 40 mL of 30% NaOH solution. Dilute with 200 mL of water. Acidify the solution with 6N HCl to the acid color of methyl red indicator. Add to this solution 40 g of NaHC03 and dilute to 1 L. 

Why is the acid-base indicator methyl red added to the solution ... 

Several properties of the filler are important to the compounder (279). Properties that are frequentiy reported by fumed sihca manufacturers include the acidity of the filler, nitrogen adsorption, oil absorption, and particle size distribution (280,281). The adsorption techniques provide a measure of the surface area of the filler, whereas oil absorption is an indication of the stmcture of the filler (282). Measurement of the sdanol concentration is critical, and some techniques that are commonly used in the industry to estimate this parameter are the methyl red absorption and methanol wettabihty (273,274,277) tests. Other techniques include various spectroscopies, such as diffuse reflectance infrared spectroscopy (drift), inverse gas chromatography (igc), photoacoustic ir, nmr, Raman, and surface forces apparatus (277,283—290). 

Sodium bicarbonate is generally added to increase alkalinity and muriatic acid (HCl) or sodium bisulfate (NaHSO ) to reduce it. In general, with acidic sanitizers such as chlorine gas or trichloroisocyanuric acid, ideal total alkalinity should be in the 100—120 ppm range, whereas, with alkaline products such as calcium, lithium, or sodium hypochlorite, a lower ideal total alkalinity of 80—100 ppm is recommended (14). Alkalinity is deterrnined by titration with standard sulfuric acid using a mixed bromcresol green—methyl red indicator after dechlorination of the sample with thiosulfate. Dechlorination with thiosulfate causes higher readings due to formation of hydroxyl ion (32) ... 

The sodium carbonate content may be deterrnined on the same sample after a slight excess of silver nitrate has been added. An excess of barium chloride solution is added and, after the barium carbonate has setded, it is filtered, washed, and decomposed by boiling with an excess of standard hydrochloric acid. The excess of acid is then titrated with standard sodium hydroxide solution, using methyl red as indicator, and the sodium carbonate content is calculated. 

Methyl Red (4-dimethylaminoazobenzene-2 -carboxylic acid) [493-52-7] M 269.3, m 181-182 , Cl 13020, pK j 2.30, pK2 4.82. The acid is extracted with boiling toluene using a Soxhlel apparatus. The crystals which separated on slow cooling to room temperature are filtered off, washed with a little toluene and recrysld from glacial acetic acid, benzene or toluene followed by pyridine/waler. Alternatively, dissolved in aq 5% NaHC03 soln, and ppted from hot soln by dropwise addition of aq HCl. Repealed until the extinction coefficients did not increase. 

Zone refining purified naphthalene from anthracene, 2,4-dinitrophenylhydrazine, methyl violet, benzoic acid, methyl red, chrysene, pentacene and indoline. 

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