JS-Naphthylamine

Dubois124 examined jS-naphthylamine at 150°C and 3660 A radiation. He found NO and 02 to be equally effective and good quenchers of fluorescence. 

Condensation also takes place between arsenious chloride and jS-naphthylamine, di-)3-naphthylamine, or di-a-naphthylaminc (not with a-naphthylamine), to yield li-chloro-U 7-dihydrodibenzophetiarsaisine (VI) in the case of the 0-compounds, and 7-chloro-7 U-dihi/drod enzo-pltenarmzitie (VII) with the a-compound ... 

The following derivatives are stable towards ammonium sulphide p - acetoxymercuri-o-nitroaniline, o - acetoxy mereuri-p-broniodimethyl-aniline, 2 4-diacetoxyniereuri-a-naphthylaniine, and p-dimethylamino-phenylmercuric acetate. If the latter compound be boiled with potassium iodide solution, then treated with hydrogen sulphide, only traces of mercuric sulphide are produced. Mercury compounds from jS-naphthylamine, j8-naphthylamine-C-sulphonic acid, 1 5-naphthyl amine sulphonic acid are decomposed b ammonium suli hide, wiiilst naphthi-onic acid derivatives are only slowty attacked. 

Aiylnaphthalenes. Arylnaphthalenes can be prepared by replacement of the amino group of naphthylamines by aryl groups. a-Phenyl-naphthalene can be prepared satisfactorily only through the stabilized diazonium salt method, but jS-phenylnaphthalene is obtained readily by several procedures. A considerable number of derivatives of 8-phenyl-naphthalene have been prepared. An example is 5-nitro-6-methoxy-2-phenylnaphthalene (XII), which can be obtained in 19% yield Irom the nitromethoxy-jS-naphthylamine and benzene. From the reaction between diazotized 8-naphthylamine and nitrobenzene and sodium acetate, j3-(2-nitrophenyl)-naphthalene (XIII 14%) and j3-(4-nitrophenyl)-naphthalene (XIV 26%) are formed. 

The primary routes of potential human exposure to coke oven emissions are inhalation and dermal contact. Occupational exposure to coke oven emissions may occur for those workers in the aluminum, steel, graphite, electrical, and construction industries. Coke oven emissions can have a deleterious effect on human health. Coke oven emissions contain literally several thousand compounds, several of which are known carcinogens and/or cocarcinogens including polycyclic organic matter from coal tar pitch volatiles, jS-naphthylamine, benzene, arsenic, beryllium, cadmium, chromate, lead, nickel subsulfide, nitric oxide, and sulfur dioxide. Most regulatory attention has been paid to coal tar pitch volatiles. 

The US Occupational Safety and Health Administration (OSHA) standard for jS-naphthylamine, 29 CFR 1910.1009, contains regulations covering periodic medical surveillance, examinations, and medical records for current employees who may have been exposed to 2NA. However, it should be noted that these regulations do not apply to former employees and that medical surveillance or treatment of former employees is not regulated or required by OSHA. 

Figure 12.10 Enrichment of jS-naphthylamine traces in methanol solutions by displacement with diethyl phthalate. Experimental (symbols) and calculated (solid lines) chromatograms. Calculations made with the equilibrium-dispersive model, a competitive Langmuir isotherm using the coefficients of the single-component isotherms, N = 3600 plates, and fluorescence quenching, (a) Displacement of 0.45 jig (6-naphthylamine by di-ethylphthalate (200 mg/mL) in methanol-water (70 30). (b) Same experiment with 275 mg/mL diethylphthalate. Reproduced with permission from R. Ramsey, A.M. Katti and G. Guio-chon, Anal. Chem., 62 (1990) 2557 (Figs. 7b and 8a). (5)1990, American Chemical Society.

Fluorescence arises from aromatic by-products which, however, can be entirely separated by careful work. Pure ac-tetrahydro-jS-naphthylamine gives no color with diazobenzene sulfonic acid. 

Sulfonation of / -naphthylamine leads to somewhat more precise orientation of the substituents. When special attention is paid to conditions such as temperature and S03 content of the sulfonation mixture, either 6- and 7-amino-l-naphthalenesulfonic acid or 6- and 7-amino-2-naphthylaminesulfonic acid can be obtained. When the concentration of S03 is increased, di- and tri-sulfonic acids of jS-naphthylamine are formed from the monosulfonic acids.151,152... 

Solely epidermal lesions were pointed out by Sato (1961) in guinea pigs sensitized with phenyl-jS-naphthylamine. 

A large number of antioxidants of organic structure, of the type of amines and phenols, were investigated in [42, 43]. The additives were introduced by powdering the capron in the form of crumbs before spinning of the fiber, as well as into the fused caprolactam before polymerization. The antioxidants beloi ing to the amine class, such as N,N -di-/3 -naphthyl-p-phenylenediamine, N, N-phenylcyclohexyl-p-phenylenedi-amine, N,N -diphenyl-p-phenylenediamine, and phenyl-jS-naphthylamine, preserve the strength of the fiber by 70-95% when it is heated for 2 hr... 

Under the influence of small additions of amines, phenols, and certain other classes of compounds, the process of polymer oxidation is sharply decelerated for example, 1% phenyl-jS-naphthylamine reduces the rate of oxidation of polybutadiene during the steady-state period at 70°C more than six-fold, while the duration of this period increases sharply. By decelerating the oxidation process, the inhibitor naturally reduces the rate and even changes the character of the structural changes in the polymers. 

In the case of diphenylamine the minimum is displaced toward higher concentrations in comparison with phenyl-jS-naphthylamine. The curve of di-/3, -naphthylamine does not pass through a minimum, but approaches a constant value. The cause of this is the low activity of the dinaphthylnitrogen radical, which is incapable of initiating oxidation of the rubber. 

In reaction (4) the material AH actually acts as a pro-oxidant. If reaction (5a) is more likely than reaction (2b) and the reaction rate of (5b) is low, AH can function as an oxidation retarder. By terminating chain reactions as in (6a) and (6b) the material acts as a chainbreaking antioxidant. A single antioxidant may act in all of these ways more or less simultaneously so that whilst in some circumstances the material may appear primarily as an antioxidant in other circumstances it may show pro-oxidant tendencies. Shelton and Cox (1954) found that when phenyl-jS-naphthylamine (PBN) was used in natural rubber above a critical concentration the oxidation rate increased (Fig. 9.1.). The most important chain-breaking antioxidants are amines and phenols (see Section 9.5). 

Shlyapnikov et al. [929] have reported distillation in vacuo at different temperatures (from 20° to 200°C), with indications of the degree of extraction from 0.02-0.1 g PE for 0.2-2.0% diphenylamine, phenyl-a-naphthylamine (Neozon A), phenyl-jS-naphthylamine (Neozon D), A-phenyl-A -cyclo-hexyl-p-phenylenediamine, A,A -di-/3-naphthyl-p-phenylenediamine, lonol, 2,4,6-tri-f-butylphenol, propyl gallate, a-naphthene, 2,2 -methylenebis(4-methyl-6-f-butylphenol), 2,2 -thiobis(4-methyl-6-f-butylphenol), 2,2 -methylenebis(4-chloro-6-f-butyl-phenol), 2,6-bis(2-hydroxy-3-f-butyl-5 -methylben-zyl)-4-methylphenol, and Tinuvin 326 reported accuracy of 1-2% using derivative (n = 2) UV spectrophotometry. 

Heating arylamines with carbon dioxide at 200°C (8500 atm) gives good yields of 3-aryl derivatives of 2,4-dihydroxyquinazoline (see 5e). The method is unsatisfactory when riitro, halo, and phenolic anilines and o- or jS-naphthylamines are used. 

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