Dichloramine-T

Dichloramine-T. Dilute 80 ml, of freshly prepared 2N sodium hypochlorite soluticMi (preparation, p. 525) with 80 ml. of w ter, and then add with stirring 5 g. of finely powdered toluene-p-sulphonamide, a clear solution being rapidly obtained. Cool in ice-water, and then add about 50 ml. of a mixture of equal volumes of glacial acetic acid and water slowly with stirring until precipitation is complete the dichloro-amide separates at first as a fine emulsion, which rapidly forms brittle colourless crystals. Filter off the latter at the pump, wash well with... 

Both chloramine-T and dichloramine-T have marked antiseptic properties, chloramine-T being most frequently used because of its solubility in water. Aqueous solutions of chloramine-T can be used either for external application, or for internal application to the mouth, throat, etc, as chloramine-T in moderate quantities is non-toxic its aqueous solution can also be effectively used when the skin has come in contact with many of the vesicant liquid poison-gases, as the latter are frequently organic sulphur or arsenic derivatives which combine with or are oxidised by chloramine-T and are thus rendered harmless. 

Both chloramine-T and dichloramine-T can be readily estimated, because they liberate iodine from potassium iodide quantitatively in the presence of... 

Dichloramine-T and chloramine-T. When p toluenesulphonamide is dissolved in excess of sodium (01 calcium) hypochlorite solution, it is converted into the soluble salt of the N-monochloro derivative ... 

Upon the addition of a weak acid (e.g., acetic acid), it reacts with the liberated hypochlorous acid giving NA -dichloro-p-toluenesulphonamide (dichloramine-T) which, being insoluble in water, crystallises rapidly ... 

When the dichloramine-T is heated with sodium hydroxide solution, the reverse change occurs and sodium N-chloro-p-toluenesulphoiiamide (chloramine-T) crystallises out on cooling at a suitable concentration ... 

Both chloramine-T and dichloramine-T slowly liberate hypochlorous aeid in eontaet with water and are therefore employed as antiseptics the former is employed in the form of a dilute (e.g., 0-2 per eent.) aqueous solution, and the latter (which is insoluble in water) as a solution in an organic solvent, such as a chlorinated paraffin. 

Dichloramine-T, A/ W-dichloro-T -toluenesulfonamide [473-34-7] is insoluble in water, but soluble in a number of organic solvents, including chlorinated paraffin. Its medical usage appears to have declined. 

Acidification of chloramine T with sulfuric acid produces the formation of dichloramine T (DCT) and hypochlorous acid (HCIO), species which react with C=C bonds of the butadiene units. The effectiveness of the treatment is ascribed to the introduction of chlorine and oxygen moieties on the mbber surface. A decrease in the pH of the chloramine T aqueous solutions produced more extended surface modifications and improved adhesion properties in the joints produced with waterborne polyurethane adhesive (Figure 27.9). The adhesive strength obtained is slightly lower than that obtained for the rubber treated with 3 wt% TCI/MEK, and its increases as the pH of the chloramine T solution decreases (Figure 27.9). A cohesive failure in the rubber is generally obtained. 

A number of organic chlorine, or chloramine, compounds are now available for disinfection and antisepsis. These are the N-chloro (=N-C1) derivatives of, for example, sulphonamides giving compounds such as chloramine-T and dichloramine-T and halazone (Fig. 10.5), which may be used for the disinfection of contaminated drinking water. 

The success of this reaction was ascribed to the solubility of the chlorozinc intermediate, whereas other chloramine-T derivatives (e.g. the sodium salt) are insoluble. An alternative non-nitrene pathway was not eliminated from consideration. On the other hand, no aromatic substitution or addition, characteristic of a free sulphonyl nitrene (see below), took place on treatment of jV,lV-dichloromethanesulphonamides with zinc powder in benzene in the cold or on heating. The only product isolated was that of hydrogen-abstraction, methanesulphonamide 42>, which appears to be more characteristic of the behaviour of a sulphonyl nitrene-metal complex 36,37). Photolysis of iV.iV-dichloromethanesulphonamide, or dichloramine-B, or dichloramine-T in benzene solution led to the formation of some unsubstituted sulphonamide and some chlorobenzene but no product of addition of a nitrene to benzene 19>. 

On the other hand, thermolysis of ferrocenylsulpkonyl azide (14) in aliphatic solvents may lead to the predominant formation of the amide (16) 17>. A 48.4% yield of (16) was obtained from the thermolysis in cyclohexane while an 85.45% yield of 16 was formed in cyclohexene. Photolysis of 14 in these solvents led to lower yields of sulphonamide 32.2% in cyclohexane, 28.2% in cyclohexene. This suggests again that a metal-nitrene complex is an intermediate in the thermolysis of 14 since hydrogen-abstraction appears to be an important made of reaction for such sulphonyl nitrene-metal complexes. Thus, benzenesulphonamide was the main product (37%) in the copper-catalyzed decomposition of the azide in cyclohexane, and the yield was not decreased (in fact, it increased to 49%) in the presence of hydroquinone 34>. On the other hand, no toluene-sulphonamide was reported from the reaction of dichloramine-T and zinc in cyclohexane. 

Dichloramine, 23 101, 102-103 Dichloramine-B, 23 109 2V,2V-Dichloramines, 23 106 Dichloramine-T, 23 109 Dichlorine dioxide, oxidation state and stability, 8 545t Dichlorine heptoxide, 18 275... 

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