Amines 2- naphthylamine

Dinitrobenzoates give crystalline complexes with aromatic amines. 1-Naphthylamine is especially suitable for identification purposes. Complex compounds are prepared by mixing both components in a mixture of alcohol and ether. These complexes crystallize well and serve as a second series of derivatives. They can also be used for the purification of 3,5-dinitrobenzoates which do not crystallize well. 

The most important color reaction of diazonium salts is their coupling with a suitable passive component, i.e., with a phenol in alkaline medium, or with an aromatic amine in acid medium (see p. 341). Among phenols, resorcinol and 2-naphthol or R-salt are suitable passive components among amines, 1-naphthylamine or N-l-naphthylethylenediamine are suitable. 

A) PRIMARY AROMATIC AMINES. RNH. Aniline, o-, m-, and p-toluidine (and other nuclear-substitiited anilines) 1- and 2-naphthylamines. (For note on Aliphatic Amines, cf. p. 375 )... 

Physical properties. Majority are liquids except p toluidine and 1- and 2-naphthylamine. All are colourless when pure, but rapidly darken on exposure to air and light. All are very sparingly soluble in water, but dissolve readily in dilute mineral acids (except the naphthyl-amines, which are only moderately soluble in adds). They form colourless crystalline salts e.g., CjHjNH2,HCl) which are soluble in water these aqueous solutions usually have an add reaction owing to hydrolysis, and give the reactions of both the amine and the acid from which they are derived. Addition of alkali to the acid solution liberates the amine. 

Basic Component. The filtrate from (a), or the HCl extract from b), now contains the basic component in the form of its hydrochloride. Add 30% aqueous NaOH solution until alkaline to litmus. Cool, and scratch the sides of the vessel with a glass rod a white precipitate indicates a solid amine, e.g, p-toluidine or a naphthylamine. Dilute, filter off, wash well with water (recrystallise if necessary), dry and identify. 

Some amines, such as the nitroanilines and the naphthylamines, give somewhat more stable diazonium compounds and may be diazotised at room temperature, when the reaction proceeds more rapidly. If the amine salt is only sparingly soluble in water, it should be suspended in the acid in a fine state of division (this is generally attained by cooling a hot solution and stirring vigorously), and it passes into solution as the soluble diazonium salt is formed. 

The initial product, nitrosobenzene, is so easily reduced to p-phenylhydroxyl-amine that it has never been isolated in the free state, but its presence has been established by reaction in solution with hydroxylamine to 3deld a phenyldi-azonium salt, which couples readily with a a-naphthylamine to form the dyestuff phenyl-azo-a-naphthylamine (compare Section IV,77) ... 

Chapter IV. a-Chloromethylnaphthalene (IV,23) benzylamine (Gabriel synthesis) (IV,39) i r.N -dialkylanilines (from amines and trialkyl orthophosphates) (IV,42) a-naphthaldehyde (Sommelet reaction) (IV,120) a-phenyl-cinnamic acid (Perkin reaction using triethylamine) (IV,124) p-nitrostyrene (IV,129) p-bromonaphthalene and p naphthoic acid (from 2 naphthylamine-1 -sulphonic acid) (IV,62 and IV,164) diphenic acid (from phenanthrene) (IV,165). 

AMINES - AMINES,AROMAHC - DIARYLAMINES] (Vol2) N-[4-(l-methyl-l-phenylethyl)phenyl]-l-naphthylamine [17418-49-4]... 

The metal coordination complexes of both sahcylaldehyde phenyhiydrazone (91) and sahcylaldoxime provide antioxidant (92) protection and uv stabihty to polyolefins (see Antioxidants). In addition, the imines resulting from the reaction of sahcylaldehyde and aromatic amines, eg, p- am in oph en o1 or a-naphthylamine, can be used at very low levels as heat stabiLizers (qv) in polyolefins (93). 

Phloroglucinol is Hsted in the Colourindex as Cl Developer 19. It is particularly valuable in the dyeing of acetate fiber but also has been used as a coupler for azoic colors in viscose, Odon, cotton (qv), rayon, or nylon fibers, or in union fabrics containing these fibers (157). For example, cellulose acetate fabric is treated with an aromatic amine such as (9-dianisidine or a disperse dye such as A-hydroxyphenylazo-2-naphthylamine and the amine diazotizes on the fiber the fabric is then rinsed, freed of excess nitrite, and the azo color is developed in a phloroglucinol bath at pH 5—7. Depending on the diazo precursor used, intense blue to jet-black shades can be obtained with excellent light-, bleach-, and mbfastness. 

As with the parent aromatic hydrocarbons, diarylamiaes based oa polycyclic aromatic amines also tead to be more harmful. Thus, /V-phenyl-2-naphthylamine [135-88-6] (PBNA) metaboli2es ia the body to produce small amouats of 2-aaphthylamiae, a known carciaogea (37). ACGIH has desigaated PBNA to be an "iadustrial substance suspect of carciaogenic potential for man."... 

Bake sulfonation is an important variant of the normal sulfonation procedure. The reaction is restricted to aromatic amines, the sulfate salts of which ate prepared and heated (dry) at a temperature of approximately 200°C in vacuo. The sulfonic acid group migrates to the ortho or para positions of the amine to give a mixture of orthanilic acid [88-21-1] and sulfanilic acid [121 -57-3] respectively. This tendency is also apparent in polynuclear systems so that 1-naphthylamine gives 1-naphthy1amine-4-su1fonic acid. 

Aldehyde-amines Aldol-naphthylamines Yes Not often used. Possibilities of carcinogenic hazard with some types. 

Naphtyl, n. naphthyl, -amin, n. naphthylamine. -aminsulfosaure, /. naphthylaminesulfonic acid, -blsu, n. naphthyl blue. 

MNN is obtained in 3—5% yield by the nitration of naphthalene and is present at this level in coml MNN. It is best prepd by indirect methods for example, by the removal of an amino group from an appropriately substituted nitro-naphthylamine. The amine is treated with Na nitrite and acid to form the diazonium salt which is replaced with a H atom by redn with EtOH (Ref 7). It may also be prepd by treatment of 6-nitro-l, 2,3,4-tetrahydronaphthalene with Br to form a dibromo compn (probably the 1,4-isomer), followed by removal of two moles of H bromide by distn in the presence of base (Ref 10). 2-Naphthalenediazonium fluoroborate... 

Dinitronaphthalene (Delta-dinitronaphtha-lenet 1,6-DNN). Crysts from acet ac, mp 166-67°, bp at 10mm 235°, 360° with decompn (Refs 2 31) CA Registry No 60746-5. It is prepd by the nitration of 2-nitronaphtha- ene with nitric ac/sulfuric ac in hot acet ac (Ref 21) by diazotization of 5-nitro-2-naphthyl-amine followed by treatment of the diazonium salt with Na cobaltinitrite, yield 40% (Ref 36) or by removal of the amino group from 1,6-dinitro-2-naphthylamine by diazotization followed by redn (Ref 17). The temp of expin is 492°(Refl7)... 

If relatively basic and nucleophilic aromatic amines are diazotized in nitrosylsul-furic acid, C- instead of TV-nitrosation takes place as shown by Blangey (1938) for 1-naphthylamine, which gave in this system 4-nitroso-l-naphthylamine. A possible mechanistic explanation of Blangey s observation is given in Section 3.2. 

Primary aromatic amines (e.g., aniline) and secondary aliphatic-aromatic amines (e. g., 7V-methylaniline) usually form triazenes in coupling reactions with benzenedi-azonium salts. If the nucleophilicity of the aryl residue is increased by addition of substituents or fused rings, as in 3-methylaniline and 1- and 2-naphthylamine, aminoazo formation takes place (C-coupling). However, the possibility has also been noted that in aminoazo formation the initial attack of the diazonium ion may still be at the amine N-atom, but the aN-complex might rearrange too rapidly to allow its identification (Beranek and Vecera, 1970). 

In a more recent paper (Stovpovoi et al., 1991b) Bagal and coworkers interpret their observation that Arrhenius plots of the rates of various N- and C-couplings of aromatic amines (e. g., 1-naphthylamine, 2,6-naphthylaminesulfonic acid, and 4-me-thylaniline) are linear only in aqueous systems, but not in aprotic solvents such as nitromethane or acetonitrile. Their explanation is based on an extension of the clas-... 

The reaction of naphthols with ammonia and sodium bisulfite is called the Bucherer reaction. Primary amines can be used instead of ammonia, in which case N-substituted naphthylamines are obtained. In addition, primary naphthylamines can be converted to secondary, by a transamination reaction ... 

Note Other aromatic amines, e. g. 1- or 2-naphthylamine in acetic acid solution (Griess reagent), can be used as coupling agent instead of N-(l-naphthyl)-ethylenediamine ... 

The amination reaction is reversible thus p-naphthylamine can be reconverted into p-naphthol by heating with aqueous so um bisulphite solution, th adding allmli and boiling until all the ammonia is expelled. 

Amines. Aniline Benzidine a-Naphthylamine p-Nitroaniline Dimethylaniline. 

Plasticiser/oil in rubber is usually determined by solvent extraction (ISO 1407) and FTIR identification [57] TGA can usually provide good quantifications of plasticiser contents. Antidegradants in rubber compounds may be determined by HS-GC-MS for volatile species (e.g. BHT, IPPD), but usually solvent extraction is required, followed by GC-MS, HPLC, UV or DP-MS analysis. Since cross-linked rubbers are insoluble, more complex extraction procedures must be carried out. The determination of antioxidants in rubbers by means of HPLC and TLC has been reviewed [58], The TLC technique for antidegradants in rubbers is described in ASTM D 3156 and ISO 4645.2 (1984). Direct probe EIMS was also used to analyse antioxidants (hindered phenols and aromatic amines) in rubber extracts [59]. ISO 11089 (1997) deals with the determination of /V-phenyl-/9-naphthylamine and poly-2,2,4-trimethyl-1,2-dihydroquinoline (TMDQ) as well as other generic types of antiozonants such as IV-alkyl-AL-phenyl-p-phenylenediamines (e.g. IPPD and 6PPD) and A-aryl-AL-aryl-p-phenylenediamines (e.g. DPPD), by means of HPLC. 

Abstract Hazardous effects of various amines, produced in the environment from the partial degradation of azo dyes and amino acids, adversely affect the quality of human life through water, soil and air pollution and therefore needed to be degraded. A number of such studies are already available in the literature, with or without the use of ultrasound, which have been summarized briefly. The sono-chemical degradation of amines and in the combination with a photocatalyst, TiC>2 has also been discussed. Similar such degradation studies for ethylamine (EA), aniline (A), diphenylamine (DPA) and naphthylamine (NA) in the presence of ultrasound, Ti02 and rare earths (REs) La, Pr, Nd, Sm and Gd, in aqueous solutions at 20 kHz and 250 W power have been carried out and reported, to examine the combinatorial efficacy of ultrasound in the presence of a photocatalyst and rare earth ions with reactive f-electrons. 

Cytotoxicity of methylamine [45], kidney liver and myocardial damage due to ethylamine [46], hepatosplenomegaly and eosinophilia due to aniline [47], euphoria, dyspnea, teratogenicity, renal failure, hematuria, proteinurea, anorexia and methanoglobinemia due to a-naphthylamine and diphenylamine have been reported in the literature [48-54]. Therefore the remediation and mineralization of amines is... 

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