Benzene-phenylene-diamine

The most noteworthy reaction of azo-compounds is their behaviour on reduction. Prolonged reduction first saturates the azo group, giving the hydrazo derivative (C NH-NH C), and then breaks the NH NH linkage, with the formation of two primary amine molecules. If method (1) has been employed to prepare the azo-compound, these two primary amines will therefore be respectively (a) the original amine from which the diazonium salt was prepared, and (6) the amino derivative of the amine or phenol with which the diazonium salt was coupled. For example, amino-azobenzene on complete reduction gives one equivalent of aniline, and one of p-phenylene diamine, NHaCeH NH benzene-azo-2-naphthoI similarly gives one equivalent of aniline and one of... 

Formation of a Quinoxaline. Heat together for 5 minutes under reflux 0 2 g. of phenanthraquinone dissolved in i ml. of glacial acetic acid and 0-2 g. of O -phenylene diamine also dissolved in i ml, of glacial acetic acid. The yellow substituted quinoxaline (p. 305) separates rapidly. Cool, filter and recrystallise from benzene m.p. 225 . 

The diaminobenzenes are made from benzene by a combination chlorination-nitration route although para-phenylene diamine is also made directly from aniline. orr/to-Phenylene diamine is widely used for the preparation of biologically active compounds such as fungicides and veterinarian medicines. The mera-diamine is used in fire-retardant textile fibers ( Nomex ) while the / ara-diamine finds use in high-strength textile fibers used for bullet-proof vests, sails, army helmets, and other types of fiber-reinforced plastics ( Kevlar ). 

In the present work a series of N.N -diphenyltetramethylcyclodisilazanes with substituents on the benzene ring were prepared from bis(phenylamino)silanes (23) (for spectroscopic data, see (ID) and, the parent compound Hlb was treated with aniline and phenylene-diamines in the melt at 200-300°C. 

DIAMINOBENZENE AMD DERIVATIVES Di ami no benzene, Phenylenediamine, or Amino-aniline (called Diamino-benzol or Phenylen-diamin in Ger), N.CgH. NH mw 106.12,... 

N,N -bis(2,2, 2-Trinitroethyl)-o-phenylene-diamine bis(Trinitroethylaimne-o-phenylene or o-bis (2,2,2-Trinitroethylamino) benzene,... 

A considerable number of acylarylamines, among them o-chloroacet-anilide, 2,6-dichloro-4-nitroacetanilide, and l-acetamido-2-methylan-thraquinone, form abnormal nitroso compounds with nitrous fumes others, such as 4-dimethylamino-4 -acetamidoazobenzene, benzene-p-toluidide, and diacetyl-1,3-phenylene diamine, do not yield nitroso compounds with nitrous fumes a third group, which includes p-nitroacet-anilide and a- and /3-acetamidoanthraquinone, is recovered unchanged after the same treatment.63 In general, the acetamido group submits to nitrosation, whereas the benzoyl and benzenesulfonyl and toluenesul-fonyl derivatives of amines are resistant to the notion of nitrous fumes. 

These investigations have not been satisfactorily concluded, which is also the case with those of Foelsing,1 who, by the oxidation of p-phenylenediamine and benzene-p-phenylene-diamine, obtained indigo-blue dyes. 

Antioxidants used were commercial products qualified for Navy fuel use DA=phenylene diamine (1,4-diamino benzene) HP=hindered phenol (2,6-di-tert-butyl-4-methylphenol). 

Beilstein Handbook Reference) Aceto DIPP Agerite White AgeRite W AI3-14324 Antigene F Antioxidant 123 Antioxidant DNP ASM-DNT 1,4-Benzenediamine, N,N -di-2-naphthalenyl- N,N -Bis-(2-naftyl)-p-fenylendiamin 1,4-Bis(2-naphthylamino)-benzene N,N -Bis((3-naphthyl)-p-phenylenediamine N,N -Bis(2-naphthyl)-p-phenylenediamine BRN 2224419 CCRIS 6026 Oi-(3-naphthyl-p-phenyldi-amine Di-(J-naphthyl-p-phenylenediamine s-Di(P-naphthyl)-p-phenylenediamine N,N -Di-p-naphlhyl-p-phenylene-diamine N,N -Di-2-naphthalenyl-1,4-benz-enediamine N,N -Di-2-naphthyl-p-phenylenediamine Diafen NN DNPD Dnpda Dwu-p-naftylo-p-fenylodwuamina EINECS 202-249-2 Nonox CL NSC 3410 p-Phenylenediamine, N,N -(di-2-naphthyl)- N,N -p-Phenylenebis(2-naphthylamine) Santowhite CL Tisperse MB-2X. Antioxidant, An antidegradant for latex, nitrile rubber, styrene-butadiene and nitrile-butadiene rubber. Solid mp = 224-230° d n 1.22-1.28 insoluble in H2O, EtOH, soluble in organic solvents LDso (rat orl) = 4500 mg/kg. Vanderbilt R. T. Co. Inc. 

The dyes of this class are derived from aromatic azo compounds, such as azobenzene, CeHs—N = N—CeHs. They are prepared by treating a diazonium salt with an amine or a phenol. Thus, if a solution of m-phenylene diamine is added to a dilute solution of benzene-diazonium chloride, the hydrochloride of diamino-azobenzene, which is the dye chrysoidine, is formed —... 

Acronyms Tg - glass transition temperature. DGEBA = diglycidyl ether of bisphenoSA, MPD = m-phenylene diamine, DCD dicyandiamide, DACH = diaminocycbhexane. DDS = diaminodiphenyl sulfone, PIP = piperidine, IPD = ist orone diamine, AEP = aminoetiiyl piperazine, BA = n-butyl acrylate, B = butadiene, S styrene, MMA methyl methacrylate, AN acrylonitrile, GMA glycidyl methacrylate, DVB divinyl benzene, EA = ethyl acrylate. 

Diamino-3,3 -dimethyldiphenylmethane p-Phenylene diamine 1,4-Bis(4-aminophenoxy)benzene... 

Preparation of rosaniline, crysaniline, safranine, and p-lenk-aniline — Acetanilide — Amido-bydroquinone — Preparation of p-phenylene-diamine—Electrolysis of benzene— p-phenylene-diamine.62-63... 

Folsing obtained p-phenylene-diamine by the electrolytic reduction of amido-azo-benzene. 

The first step in m-phenylene diamine (MPD) synthesis is the nitration of benzene in 20% oleum (Equation 13.1). The nitration is a two-stage continuous process [38] replacing two protons on the benzene ring with two nitro groups by the catalytic action of sulfuric acid. The m-isomer is the dominant product. 

Synthesis of N,N,-bis(4-nitrophenyl)-N, N -bis[4-(2-phenyl-2-isopropyl) phenyl]- ,4-phenylene-diamine (3). In a 250 ml three neck round-bottom lisk was placed bis- [4-(2-pheiiyl- 2-isopropyl)phenyl]-4-aminopheitylamine (2) (7.26 g, 14.63 mmol), 4-Qtoro-nitro- benzene (4.13 g, 29.27 mmol), cesium Qioride (4.41 g, 29.27 mmol), and 80 ml DMSO. The mixture was heated with stirring at 120"C for 24 hr. The reaction mixture was cooled and then poured into 500 ml methanol. The red precipitate was collected by titration and dried under vacuum. The product was puriffed by sihca gel colunrn chromatography ( -hexane dichloromethane = 1 1) to afford dinitio compoimd (3) in a 65% yield mp 224-225 "C (by DSC 10°C /min). 

Several solvents, such as n-decane, n-hex-ane, benzene, chlorobenzene and dichloro-methane, which are immiscible with water, were used. The effect of solvent on conversion is shown in Figure 13.3.3. The order of die conversion of o-phenylene diamine CgH4(NH2)2 in various organic solvents is dichloromethane > chlorobenzene > benzene > n-hexane > n-decane, which is consistent with the order of solvent polarity, i.e., the greater the polarity of solvent the higher the conversion of o-phenylene diamine. 

The a-acids form crystalline adducts with 1,2-diaminobenzene (o-phenylene diamine) and repeated recrystallization of the adduct of the mixed a-acids from benzene or cyclohexane affords the humulone complex, m.p. 118°, free of that of cohumulone. Decomposition of the adduct with hydrochloric acid gives pure humulone. 

Synonyms Agerite DPPD N,N -diphenyl-p-phenylenediamine 1,4-dianilinobenzene diphenyl PPD DPPD N,N -diphenyl-i,4-benzenediamine i,4-bis(phenylamino) benzene N,N -diphenyl-i,4-diaminobenzene 4,4 -diphenyl-p-phenylenediamine diphenyl-p-phenylenediamine Flexamine G JZF Nonox DPPD p-phenylaminodiphenylamine p-phenylenediphenyldiamine Diafen Diafen FF N,N -diphenyl-i,4-phenylenediamine Altofane dip Nonflex H Permanax 18 Stabilizer DPPD p-bis(phenylamino)benzene Nocrac DP Permanax DPPD DFFD Antage DP Ekaland DPPD Naugard J N,N -diphenyl-p-phenylene diamine... 

Pyromellitic dianhydride (PMDA) was obtained from commercial sources and purified by vacuum sublimation, m.p. 285°. The m-phenylenediamine was recrystallised three times from dry benzene and dried at room temperature over CaCl at 2)mm. The monomer was further purified by sublimation, m.p. 59 . p-Phenylene diamine was siiblimed twice (80 /3mnO from activated charcoal and stored under nitrogen. Dimethyl formamide (DMF) (b.p. 79 /38mm) was distilled from calcium hydride and stored over molecular sieves. 

Various amines such as m-phenylene diamine, p-phenylene diamine and hexamethylene diamine have been used for the preparation of polyamideimide. It has been found that the molecular weight of the polymers as evident from inherent viscosity values is low. It may be explained on the basis of unequal reactivity of the two acyl chloride groups of RMIDC. The acyl chloride group attached to the benzene ring of p-amino benzoic acid moiety is sterically less bin-... 

Double ring closure. A mixture of bicyclo[3.3.1]nonane-3,7-dione, o-phenylene-diamine, and molecular sieve 3A refluxed 2 hrs. in benzene product. Y 81%. R. Yamagudii, K. H. Yang, and M. Kawanisi, Bull. Chem. Soc. Japan 46, 673 (1973). 

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