Naphthalene tetrachloride

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. 

Napthalene resembles benzene closely in its behavior with reagents. When it is treated with a mixture of potassium chlorate and hydrochloric acid, the chlorine set free adds directly to the hydrocarbon and naphthalene tetrachloride is formed. The four chlorine atoms add to one of the rings. 

Use a 500 ml. three-necked flask equipped as in Section IV,19, but mounted on a water bath. Place 128 g. of naphthalene and 45 ml. of dry carbon tetrachloride in the flask, and 177 g. (55 ml.) of bromine in the separatory funnel. Heat the mixture to gentle boiling and run in the bromine at such a rate that little, if any, of it is carried over with the hydrogen bromide into the trap this requires about 3 hours. Warm gently, with stirring, for a further 2 hours or until the evolution of hydrogen bromide ceases. Replace the reflux condenser by a condenser set for downward distillation, stir, and distil off the carbon tetrachloride as completely as possible. Mix the residue with 8 g. of sodium... 

Naphthalene is very slightly soluble in water but is appreciably soluble in many organic solvents, eg, 1,2,3,4-tetrahydronaphthalene, phenols, ethers, carbon disulfide, chloroform, ben2ene, coal-tar naphtha, carbon tetrachloride, acetone, and decahydronaphthalene. Selected solubiUty data are presented in Table 4. 

The following reductions have been carried out at 80° with the use of an excess of 2-propanol as the reaction medium (see Note 3) carbon tetrachloride to methane (47%), 1-bromonaph-thalene to naphthalene (90%), /3-bromostyrene to styrene (72%), jfi-bromoaniline to aniline (61%), p-bromophenol to phenol (66%), and monochloroacetone to acetone (30%). 

Oscik and Chojnacka [63] use TEC adsorption in the investigation of six aromatic hydrocarbons (naphthalene, diphenyl, anthracene, pyrene, chrysene, and acenaphthene) on silica gel G by elution with different binary mobile phases (trichloroethylene-benzene, carbon tetrachloride-benzene, n-heptane-trichloroethylene. 

Dissolve 71 g. of P-methylnaphthalene in 460 g. (283 ml.) of A.B. carbon tetrachloride and place the solution in a 1 -litre three-necked flask equipped with a mechanical stirrer and reflux condenser. Introduce 89 g. of JV-bromosuccinimide through the third neck, close the latter with a stopper, and reflux the mixture with stirring for 16 hours. Filter ofiT the succinimide and remove the solvent under reduced pressure on a water bath. Dissolve the residual brown oil (largely 2-bromomethyl naphthalene) in 300 ml. of A.R. chloroform, and add it to a rapidly stirred solution of 84 g. of hexamine in 150 ml. of A.R. chloroform contained in a 2-litre three-necked flask, fitted with a reflux condenser, mechanical stirrer and dropping funnel maintain the rate of addition so that the mixture refluxes vigorously. A white solid separates almost immediately. Heat the mixture to reflux for 30 minutes, cool and filter. Wash the crystalline hexaminium bromide with two 100 ml. portions of light petroleum, b.p. 40-60°, and dry the yield of solid, m.p. 175-176°, is 147 g. Reflux the hexaminium salt for 2 hours with 760 ml. of 60 per cent, acetic acid, add 160 ml. of concentrated hydrochloric acid, continue the refluxing for 5 minutes more, and cool. Extract the aldehyde from the solution with ether, evaporate the ether, and recrystallise the residue from hot -hexane. The yield of p-naphthaldehyde, m.p. 69-60°, is 60 g. 

The above method has been found to be more convenient and to give considerably better yields than that described previously.1 Bromination of naphthalene in carbon tetrachloride solution has also recently been described by Blicke.2... 

NAPHTHALENE THIOL, 51, 139 Titanium tetrachloride, 54, 93 o-Tolualdehyde, by reduction of... 

In the case of naphthalene, transitions to the two lowest excited states (again, often indicated with Lb and La) are two-photon forbidden, as in benzene. However, due to vibronic coupling, the Lb band is visible in the 2PA spectrum of naphthalene in the 575-650 nm region (see Fig. 5), while La gains intensity in the IPA spectrum and peaks around 275 nm [44-46], but is basically absent from the 2PA spectrum this is again in line with predictions based on the pseudoparity of the states. Polarization ratio data were used to aid the band assignment. A weak 0-0 peak of the Lb band can actually be seen in the 2PA spectrum (at 630.5 nm for naphthalene in cyclohexane [45] and at 631.8 nm in carbon tetrachloride [47]), probably because of local perturbation of the symmetry due to the solvent environment or other effects [44,45]. The 2PA... 

Similarly with the raising of the b.p. in violet or reddish-violet soln. of iodine in benzophenone, carbon disulphide, ethyl chloride, chloroform, carbon tetrachloride, ethylene chloride or benzene or in brown soln. of ethyl alcohol, methyl alcohol, thymol, ethyl ether, methylal, or acetone. The values for the last three solvents were rather low, presumably because of the chemical action of solute on solvent. High values with benzene are attributed to the formation of a solid soln. of solvent and solid. Confirmatory results were found by J. Hertz with naphthalene, and by E. Beckmann and P. Wantig with pyridine. The results by I. von Ostromisslensky (o-nitrotoluene), by G. Kriiss and E. Thiele (glacial acetic acid), and by H. Gautier and G. Charpy indicate polymerization, but they are not considered to be reliable. 

The action of carbon tetrachloride or a mixture of chlorine with a hydrocarbon or carbon monoxide on the oxide.—H. N. Warren 9 obtained aluminium chloride by heating the oxide to redness with a mixture of petroleum vapour and hydrogen chloride or chlorine, naphthalene chloride or carbon tetrachloride was also used. The bromide was prepared in a similar manner. E. Demarpay used the vapour of carbon tetrachloride, the chlorides of chromium, titanium, niobium, tantalum, zirconium, cobalt, nickel, tungsten, and molybdenum H. Quantin, a mixture of carbon monoxide and chlorine and W. Heap and E. Newbery, carbonyl chloride. 

Chemicals which can damage (a) the liver include carbon tetrachloride, paracetamol, bromobenzene, isoniazid, vinyl chloride, ethionine, galactosamine, halothane, dimethyl-nitrosamine (b) the kidney include hexachlorobutadiene, cadmium and mercuric salts, chloroform, ethylene glycol, aminoglycosides, phenacetin (c) the lung include paraquat, ipomeanol, asbestos, monocrotaline, sulfur dioxide, ozone, naphthalene (d) the nervous system include MPTP, hexane, organophosphoms compounds, 6-hydroxydopamine, isoniazid (e) the testes include cadmium, cyclophosphamide, phthalates, ethanemethane sulfonate, 1,3-dinitrobenzene (f) the heart include allylamine, adriamycin, cobalt, hydralazine, carbon disulfide (g) the blood include nitrobenzene, aniline, phenyl-hydrazine, dapsone. 

Thiocyanation can be directed, by choice of suitable reaction conditions, to the nucleus or side chain of most aralkyl hydrocarbons. For example 1-methylnaphthalene gives exclusively l-methyI-4-cyanato-naphthalene in acetic acid in darkness but gives exclusively 1-thio-cyanatomethylnaphthalene on irradiated carbon tetrachloride solution. Mixtures of the two, in varying proportions, are obtained from solutions allowed to stand in ordinary sunlight. 

Zinc dust, hexachloroethane and aluminium Phosphorous pentoxide and phosphoric acid Sulfur, potassium nitrate and pitch Potassium chlorate, naphthalene and charcoal Zinc dust, hexachloroethane and naphthalene Silicon tetrachloride and ammonia vapour Auramine, potassium chlorate, baking soda and sulfur Auramine, lactose, potassium chlorate and chrysoidine Rhodamine red, potassium chlorate, antimony sulfide Rhodamine red, potassium chlorate, baking soda, sulfur Auramine, indigo, potassium chlorate and lactose Malachite green, potassium chlorate, antimony sulfide Indigo, potassium chlorate and lactose Methylene blue, potassium chlorate, antimony sulfide... 

While no spectroscopic evidence of a ground-state complex between anthracene and carbon tetrachloride, naphthalene or 1,2-benzanthracene and carbon tetrabromide has been found, Nemzek and Ware [7] were unable to explain their steady-state fluorescence quenching measurements with the parameters deduced from the determination of the time-dependent rate coefficients unless a ground-state complex was present. This cannot be regarded as a satisfactory and consistent analysis because the time-dependent rate coefficient would be modified by the presence of the initial distribution of quencher and fluorophor in the ground state. 

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