Decolorisation

Decolorise a solution of potassium manganate(Vll) acidified with dilute sulphuric acid. 

In acid solution, the manganate(VII) ion is reduced to the manganesefll) ion with decolorisation ... 

When titanium dissolves in dilute hydrochloric acid, a violet solution containing titanium(III) ions is formed. This solution rapidly decolorises acidified aqueous potassium permanganate at room temperature. Titanium(IV) chloride is a colourless covalent liquid completely hydrolysed by water. Titanium(III) chloride forms hydrated titanium(III) ions in water and disproportionates when heated in a vacuum. 

Decolorisation by Animal Charcoal. It sometimes hap pens (particularly with aromatic and heterocyclic compounds) that a crude product may contain a coloured impurity, which on recrystallisation dissolves in the boiling solvent, but is then partly occluded by crystals as they form and grow in the cooling solution. Sometimes a very tenacious occlusion may thus occur, and repeated and very wasteful recrystallisation may be necessary to eliminate the impurity. Moreover, the amount of the impurity present may be so small that the melting-point and analytical values of the compound are not sensibly affected, yet the appearance of the sample is ruined. Such impurities can usually be readily removed by boiling the substance in solution with a small quantity of finely powdered animal charcoal for a short time, and then filtering the solution while hot. The animal charcoal adsorbs the coloured impurity, and the filtrate is usually almost free from extraneous colour and deposits therefore pure crystals. This decolorisation by animal charcoal occurs most readily in aqueous solution, but can be performed in almost any organic solvent. Care should be taken not to use an excessive quantity... 

Sometimes termed activated or decolorising charcoal, to distinguish it from wood charcoal, which absorbs gases. 

Students should distinguish carefully between the animal charcoal used for decolorisation, and the wood charcoal which is used for absorbing easily liquefiable gases, and which is therefore used in gas respirators and also, when chilled in liquid air, for obtaining high vacua. 

Note that many readily oxidisable compounds (e.g., aldehydes) will also decolorise alkaline potassium permanganate in the cold. 

Action of bromine water. To a concentrated aqueous solution of the phenol or to the phenol itself, add bromine water gradually. At first the bromine is decolorised and then on adding an excess a white or yellowish-white precipitate of a polybromo-derivative is produced with all except catechol, hydroquinone, i- and 2 naphthol. 

On adding i drop of bromine water to catechol, a deep red coloration is produced immediately. On gradually adding bromine water to a solution of hydroquinone, a deep red coloration is produced, followed by the separation of deep green crystals which then dissolve giving a yellow solution, i- and 2-Naphthol will decolorise hromine water, but usually no precipitate of the bromo compound can be obtained. 

Reduction of acid permanganate. Add a few ml. of dil. HgSO to 1 ml. of a solution of oxalic acid or of an oxalate. Warm gently and add a dilute solution of KMn04 drop by drop and note the decolorisation. 

Oxidation, (a) Unsaturation test. Dissolve about o-i g. of cinnamic acid or of a soluble cinnamate in about 5 ml. of 10% NajCOg solution. To the cold solution add 1% aqueous KMn04 drop by drop. Immediate decolorisation denotes unsaturation. (Note. Many easily oxidisable substances, e.g.y formic acid, acetaldehyde, etc.y also rapidly decolorise alkaline permanganate. Cinnamates, however, do not reduce Fehling s solution.)... 

Phthalcin reaction. Fuse together very gently in a dry test-tube 01 g. of phthalimide, O l g. of phenol and 2 drops of cone. HjSO, Cool, add waier and then NaOH solution in excess. A red coloration is produced which is decolorised by acids. (Note. Succinimide gives no definite coloration in these circumstances.)... 

Sorensen s reaction. First read carefully the Estimation of Glycine, p. 463. Dissolve 0 2 g. of glycine in a few ml. of water in a test-tube A, add 2 drops of phenolphthalein and then very dilute NaOH solution drop by drop until the solution just turns pink. In a second test-tube B place 2 ml. of 40% formalin solution, add 2 drops of phenolphthalein solution and then the dil. NaOH solution until the solution just turns pink. Pour the contents of B into A and note the immediate decolorisation of the phenolphthalein, the solution now being acid. Observe also that several drops of dil. NaOH solution can now be added before the pink colour is restored. 

Diazotisation. Dissolve 0 2 g. of the substance in about 5 ml. of dil. HCl, warming if necessary. Cool in ice-water and add sodium nitrite solution drop by drop the end of the diazotisation is marked by the complete decolorisation of the solution. Pour the diazonium solution into a cold solution of 2-naphthol in a considerable excess of NaOH solution a brilliant red dye is produced. 

Dibromide formation. Dissolve 0 2 ml. of styrene in 0 5 ml. of CCI4 in a test-tube. Add slowly, drop by drop, a 10% solution of bromine in CCI4. Note the decolorisation of the bromine and absence of HBr fumes (therefore reaction by addition and not by substitution). Continue to add the bromine solution until a faint brown colour persists. Scratch the sides of the tube and cool it in ice-water. Filter off the crystals that separate and recrystallise the styrene dibromide from methanol m.p. 72 . 

Stilbene decolorises bromine only on heating. Proceed as above, but keep the stilbene solution hot during the addition of the CCI4 solution of bromine. Stilbene dibromide has m.p. 237 . 

Several variations of the chemical method are in use. In the one described below, a freshly prepared Fehling s solution is standardised by titrating it directly against a standard solution of pure anhydrous glucose when the end-point is reached, I. e., when the cupric salt in the Fehling s solution is completely reduced to cuprous oxide, the supernatant solution becomes completely decolorised. Some difficulty is often experienced at first in determining the end-point of the reaction, but with practice accurate results can be obtained. The titrations should be performed in daylight whenever possible, unless a Special indicator is used (see under Methylene-blue, p. 463). 

Place 5 ml. of milk in each of two test-tubes A and B. Boil the milk in B thoroughly for 2 minutes to destroy the enzyme, and cool. Then in each test-tube place i ml. of the acetaldehyde solution and i ml of the methylene-blue solution. Mix gently by inverting the tubes avoid shaking with air. Now place A and B in a water-bath maintained at 40-50. After a time (usually about 20 minutes) the dye in A is completely decolorised except at the surface, while B is unaffected. 

Because of their zwitterionic nature, amino acids are generally soluble in water. Their solubility in organic solvents rises as the fat-soluble portion of the molecule increases. The likeliest impurities are traces of salts, heavy metal ions, proteins and other amino acids. Purification of these is usually easy, by recrystallisation from water or ethanol/water mixtures. The amino acid is dissolved in the boiling solvent, decolorised if necessary by boiling with Ig of acid-washed charcoal/lOOg amino acid, then filtered hot, chilled, and set aside for several hours to crystallise. The crystals are filtered off, washed with ethanol, then ether, and dried. 

Water-soluble salts are best purified by preparing a concentrated aqueous solution to which, after decolorising with charcoal and filtering, ethanol or acetone is added so that the salts crystallise. They are collected, washed with aqueous ethanol or aqueous acetone, and dried. In some cases, water-soluble salts can be recrystallised satisfactorily from alcohols. Water-insoluble salts are purified by Soxhlet extraction, first with organic solvents and then with water, to remove soluble contaminants. The purified salt is recovered from the thimble. 

V-Allylthiourea (thiosinamine) [109-57-9] M 116.2, m 70-73 , 78 . Recrystd from H2O. Soluble in 30 parts of cold H2O, soluble in EtOH but insoluble in "CeHg. Also recrystd from acetone, EtOH or ethyl acetate, after decolorising with charcoal. The white crystals have a bitter taste with a slight garlic odour and are TOXIC. [Anal Chem 21 421 7949.]... 

Aminophenol [95-55-6] M 109.1, m 175-176 , pKj 4.65, pKj 9.75. Purified by soln in hot water, decolorised with activated charcoal, filtered and cooled to induce crystn. Maintain an atmosphere of N2 over the hot phenol soln to prevent its oxidation [Charles and Preiser J Am Chem Soc 74 1385 7952]. Can also be crystd from EtOH. 

Biquinolyl (a,a -diquinolyl) [119-91-5] M 256.3, m 196 , pKe, 4.2. Decolorised in CHCI3 soln (charcoal), then crystd to constant melting point from EtOH or pet ether [Cumper, Ginman and Vogel J Chem Soc 1188 1962]. 

Bromotetronic acid [21151-51-9] M 179.0, m 183°(dec), pK 2.23. Decolorised, and free bromine was removed by charcoal treatment of an ethyl acetate soln, then recrystd from ethyl acetate [Schuler, Bhatia and Schuler J Phys Chem 78 1063 1974]. 

Nitroindole [6146-52-7] M 162,1, m 141-142 , pK -7,4 (aq H2SO4). Decolorised (charcoal) and recrystd twice from aqueous EtOH. 

Potassium hydrogen malate [4675-64-3] M 172.2. A saturated aqueous solution at 60° was decolorised with activated charcoal, and filtered. The filtrate was cooled in water-ice bath and the salt was ppted by addition of EtOH. After being crystallised five times from ethanol-water mixtures, it was dried overnight at 130° in zir [Edenand Bales J Res Nat Bur Stand 62 161 1959],... 

Sodium p-toluenesulfinate [824-79-3] M 178.2, pK 2.80 (1.99)(for -S02 ). Crystd from water (to constant UV spectrum), and dried under vacuum or extracted with hot benzene, then dissolved in EtOH-H20 and heated with decolorising charcoal. The solution was filtered and cooled to give crystals of the dihydrate. 

Trisodium 8-hydroxy-l,3,6-pyrenetrisulfonate [6358-69-6J M 488.8, m >300(dec). Purified by chromatography with an alumina column, and eluted with -propanol-water (3 1, v/v). Recrystd from aqueous acetone (5 95, v/v) using decolorising charcoal. 

Nicotelline, CjoHgNj. This base, isolated by Pictet and Rotschy, forms colourless needles, m.p. 147-8°, b.p. above 300° its aqueous solution is neutral to litmus. Unlike other tobacco bases it yields a sparingly soluble, crystalline dichromate. It does not decolorise acid permanganate, and appears not to be a pyrrole derivative. ... 

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