Di naphthalenes

Brown HT (El55, Cl Food Brown 3, Chocolate brown) is a bis azo dye, with the chemical name disodium 4,4 -(2,4-dihydroxy-5-hydroxymethyl-l,3-phenylene-bisazo) di(naphthalene-l-sulfonate). The calcium and potassium salts are also permitted. Brown HT is a reddish-brown powder or granules, soluble in water, insoluble in ethanol, with a maximum absorption in water at 460 nm, pH 7, = 403). 

Chocolate brown HT E 156 20285 A Di sodium-4,4 -(2,4-dihydroxy-5-hydroxymethyl-l,3-phenylene bisazo)di(naphthalene-l-sulfonate) C27H18N4Na209S2 652.57 460... 

Figure 36 Quenching effects on photoluminescence (PL) and electroluminescence (EL) of fluorescent Alq3 and phosphorescent Ir(ppy)3 emitters due to aging by operation of an Alq3-based LED at 50mA/cm2 (a) and by exposing a 150nm-thick Ir(ppy)3 film to the UV-radiation (=313 nm) under ambient conditions (b). The data of part (a) have been obtained with the EL structure as shown in the inset ITO /N, AP-di(naphthalene- l-yl)-iV /AP-diphenyl-benzidine...

The fluorescence spectra of 2,5-diarylpyrazines have been studied the presence of electron-donating substituents on each aryl group, as in 2,5-bis(p-methoxyphenyl)pyrazine (246), strengthened fluorescence on photoexcitation the fluorescence of 2,5-di(naphthalen-2-yl)pyrazine (247) proved stronger than that of the isomeric 2,5-di(naphthalen-l-yl)pyrazine due to reduced planarity in the latter structure.1288 p-Bis[2-(pyrazin-2-yl)vinyl]benzene (248) proved to be an efficient blue laser dye (emission A-max 438 nm in Me2SO solution) on excitation by a nitrogen laser at 337 nm.1484... 

Since MBH reactions carried out with common ionic liquids, such as [bmim]pC], give lower to moderate yields, more recently, Tsai el al. have synthesized a new and highly active di-naphthalene imidazolium salt. They found that l,3-bis[2-(naphthalene-2-yloxy)propyl]imidazolium bromide (306) promoted... 

S,5S)-2,5-Di(naphthalen-2-yl)pyrrolidine (V) (25, 55)-2,5-Di (naphthalen-2-yl)-2,5-dihydro-liS-pyrrole 7 (0.142g, 0.442 mmol, 1 equiv) (or the corresponding HBr salt) was dissolved in CH2CI2 (10 mL) at room temperature, an oxygen atmosphere was applied (balloon), and the reaction mixture was stirred extremely... 

Figure 9.14 Shows the chemical structure of three hole transporter molecules, (a) N,N -diphenyl-A,A -bis(3-methylphenyl)-l,l-biphenyl-4,4 -diamine or NPD, (b) A,A -di(naphthalene-l-yl)-A,A -diphenyl-benzidine or TPD, and (c) 4,4 -N,N -dicarbazole biphenyl or CPB.

Sulfonation. Sulfonation of naphthalene with sulfuric acid produces mono-, di-, tri-, and tetranaphthalenesulfonic acids (see Naphthalene derivatives), ah of the naphthalenesulfonic acids form salts with most bases. Naphthalenesulfonic acids are important starting materials in the manufacture of organic dyes (15) (see Azo dyes). They also are intermediates used in reactions, eg, caustic fusion to yield naphthols, nitration to yield nitronaphthalenesulfonic acids, etc. 

Chlorine Addition. Chlorine addition and some chlorine substitution occurs at normal or slightly elevated temperatures in the absence of catalysts. The chlorination of molten naphthalene under such conditions yields a mixture of naphthalene tetrachlorides, a monochloronaphthalene tetrachloride, and a dichloronaphthalene tetrachloride, as well as mono- and dichloronaphthalenes (35). Sunlight or uv radiation initiates the addition reaction of chlorine and naphthalene resulting in the production of the di- and tetrachlorides (36). These addition products are relatively unstable and, at ca 40—50°C, they decompose to form the mono- and dichloronaphthalenes. 

Isopropylnaphthalenes can be prepared readily by the catalytic alkylation of naphthalene with propjiene. 2-lsopropylnaphthalene [2027-17-0] is an important intermediate used in the manufacture of 2-naphthol (see Naphthalenederivatives). The alkylation of naphthalene with propjiene, preferably in an inert solvent at 40—100°C with an aluminum chloride, hydrogen fluoride, or boron trifluoride—phosphoric acid catalyst, gives 90—95% wt % 2-isopropylnaphthalene however, a considerable amount of polyalkylate also is produced. Preferably, the propylation of naphthalene is carried out in the vapor phase in a continuous manner, over a phosphoric acid on kieselguhr catalyst under pressure at ca 220—250°C. The alkylate, which is low in di- and polyisopropylnaphthalenes, then is isomerized by recycling over the same catalyst at 240°C or by using aluminum chloride catalyst at 80°C. After distillation, a product containing >90 wt % 2-isopropylnaphthalene is obtained (47). 

Mixtures containing various concentrations of mono-, di-, and polyisopropylnaphthalenes have been prepared by treating molten naphthalene with concentrated sulfuric acid and propjiene at 150—200°C followed by distillation (39). Products comprised of such isomeric mixtures have extremely low pour points, ie, ca —50° C, are excellent multipurpose solvents, and have been evaluated as possible Hquid-phase heat-transfer oils. 

Physical properties for naphthalene mono-, di-, tri-, and tetracarboxyhc acids are summari2ed in Table 9. Most of the naphthalene di- or polycarboxyLic acids have been made by simple routes such as the oxidation of the appropriate dior polymethylnaphthalenes, or by complex routes, eg, the Sandmeyer reaction of the selected antinonaphthalenesulfonic acid, to give a cyanonaphthalenesulfonic acid followed by fusion of the latter with an alkah cyanide, with simultaneous or subsequent hydrolysis of the nitrile groups. 

The most abundant aromatics ia the mid-distiUate are mono-, di-, and trimethyl naphthalenes. Other one- and two-ting aromatics are undoubtedly present ia smaU quantities as either naphtheno or alkyl homologues ia the addition to these homologues of alkylben2enes, tetralins, and... 

Copolymers of diallyl itaconate [2767-99-9] with AJ-vinylpyrrolidinone and styrene have been proposed as oxygen-permeable contact lenses (qv) (77). Reactivity ratios have been studied ia the copolymerization of diallyl tartrate (78). A lens of a high refractive iadex n- = 1.63) and a heat distortion above 280°C has been reported for diallyl 2,6-naphthalene dicarboxylate [51223-57-5] (79). Diallyl chlorendate [3232-62-0] polymerized ia the presence of di-/-butyl peroxide gives a lens with a refractive iadex of n = 1.57 (80). Hardness as high as Rockwell 150 is obtained by polymerization of triaHyl trimeUitate [2694-54-4] initiated by benzoyl peroxide (81). 

Alkylphenols, ammonia, asbestos, chlorinated paraffins, 4-chloroaniline, cyanide, detergents, di- -butyl phthalate, polyaromatic hydrocarbons (PAHs e.g. anthracene, benzopyrene, methylcholanthrene, /i-naphthoflavone), nitrate, nitrite, petroleum oil, phenol, pentachlorophenol, 4-nitrophenol, dinitro-o-cresol, polychlorinated biphenyls (PCBs especially coplanar), polychlorinated dioxins, polybrominated naphthalenes, /i-sitosterol, sulfide, thiourea, urea, acid water, coal dust... 

Naphthalene-1,8-dicarboxylic add, its nitro-substituted derivatives, and naphthalene-1,4,5,8 tetracarboxylic acid, on treatment with sulfur tetrafluoride at 0 C, undergo dehydration to form quantitatively the corresponding anhydrides [218, 221] Unsubstituted and mononitrated monoanhydndes react further at 200-250 °C to give derivatives of 1,1,3,3-tetrafluoro-l// naphtho[I,8 c,d]pyran Dinitronaphthalene-l,8-di-carboxyhc acid anhydndes and naphthalene 1,4,5,8 tetracarboxylic acid dianhydnde give the respective tetra- and octafluoroethers only in the presence of an excess of anhydrous hydrogen fluoride [221] (equabons 113 and 114)... 

The technical method for obtaining phenol is by shaking out with caustic soda the middle oil of the coal-tar distill ate,. after some of the naphthalene has crystallised out. The phenol dis-soKes m the alkali, and is then lemoved fiom insoluble oils. The alkaline liquid is acidified, the phenol separated, distilled, and finally purified by freezing. 

Figure 14.19 Typical GC chromatogram of the separated di-aromatics fraction of a middle distillate sample Peak identification is as follows 1, naphthalene 2, 2-methylnaphthalene 3, 1-methylnaphthalene 4, biphenyl 5, C2-naphthalenes 6, C3-naphthalenes 7, C4-naph-thalenes 8, C5+-naphthalenes 9, benzothiophene 10, methylbenzothiophenes 11, C2-ben-zotliiopIrenes. Note the clean baseline between naphthalene and the methylnaphthalenes, which means that no overlap with the previous (mono-aromatics) fraction has occuned.

The method illustrates the ability of the sodium hydride-dimethylformamide system to effect the alkylation of aromatic sulfonamides under mild conditions and in good yield. The method appears to be fairly general. The submitters have prepared N,N-diethyl- and N,N-di- -butyl- >-toluenesulfonamide as well as 2-(/ -tolyIsuIfonyl)benz[/]isoindoline from 2,3-bis-(bromomethyl)naphthalene, and 1 %-tolylsulfony])pyrrolidine from 1,4-dichIorobutane the yield of purified product exceeded 75% in each case. 

Besides a parent ion, the mass spectra of benzo- and dibenzothiepins show the corresponding naphthalene or phenanthrene radical cations as the base peak.2-16 The mass spectra of 1-benzo-thiepin 1-oxides and 1,1-dioxides show the same naphthalene radical cation, formed by loss of sulfur monoxide or sulfur dioxide, respectively.14 In contrast, in the mass spectrum of 2,7-di-terf-butylthiepin peaks resulting from the loss of sulfur are not found.17... 

A mixture of l,4-di(hexyloxy)naphthalene-2,3-dicarbonitrile (756 mg, 2 mmol), Ni(OAc)2 (175 mg, 0.7 mmol), and DBU (1.5 mL) in hexan-l-ol (25 mL) was heated under N2 for 24 h under reflux. The cooled green-brown solution was poured into MeOH/H20 (1 1,150 mL) and the precipitate formed was filtered, washed with MeOH, and dried in vacuo. Further purification was achieved by column chromatography (silica gel, CHC13) in the dark to yield the title compound as a light-brown powder yield 480 mg (61 %). 

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