Amine trisulfonate

HN02 z=f=r ho3sno (HO S) NIOH J (ho3s) 3n Nitrous acid Nitrososulfonic Hydroxylamine Amine trisulfonic acid disulfonic acid acid... 

Further sulfonation to produce hydroxylamine disulfonate and amine trisulfonate. These sulfonates can hydrolyze to form sulfuric acid and reduced nitrogen species. The latter can undergo further reaction with bisulfite and nitrite. 

Nitrous acid Nitrososulfonic Hydroxylamine Amine trisulfonic... 

Many aminonaphthalenesulfonic adds arc important in the manufacture of azo dyes or are used to make intermediates for azo acid dyes, direct and fiber-reactive dyes. Usually, the aminonaphthalenesulfonic adds are made by either tile sulfonation of naphthaleneamines, the nitration-reduction of naphthalenesulfomc adds, the Bucherer-type amination of naphtholsulfomc acids, or the desulfonation of an aminonaphthalenedi- or trisulfonic acid. Most of these processes produce by-products or mixtures which often are separated in subsequent purification steps. A list of commercially important ammonaphlhalenesulfomc acids is given in Table 4. 

Derivation (3-naphthylamine sulfate is sulfonated with 66% oleum, the filtrate yields 2-naphthyl-amine-l,5,7-trisulfonic acid. On reaction with dilute sulfuric acid at 125C, this yields 2-naphthylamine-5,7-disulfonic acid from this J acid is obtained on reaction with 58% sodium hydroxide solution at 200C and 210 psi. 

Figure 12.3 Molecular structure of protonated amine photoacids 1-aminopyrene (lAP), /V-methyl-1-aminopyrene (MAP), /V,/V-dimethyl-l-aminopyrene (DMAP), 8-aminopyrene-l,3,6-trisulfonate (APTS).

Initially, only dipolar aprotic solvents such as tertiary amines, acetonitrile (MeCN), di-methylformamide (DMF), V-methylpyrrolidinone (NMP), and dimethylsulfoxide (DMSO), were common. However, as originally observed by Heck, the presence of water can accelerate certain coupling reactions, "" and consequently the development has gone to water-soluble triarylphosphane ligands (e.g., tiiphenylphosphane m-trisulfonate sodium salt (TPPTS) ) with which many alkene arylations superbly succeed in aqueous solvent mixtures. ° ... 

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