Tetraline

It is a typically aromatic compound and gives addition and substitution reactions more readily than benzene. Can be reduced to a series of compounds containing 2-10 additional hydrogen atoms (e.g. tetralin, decalin), which are liquids of value as solvents. Exhaustive chlorination gives rise to wax-like compounds. It gives rise to two series of monosubstitution products depending upon... 

Or by a naphthenic ring which can also be substituted for two adjacent hydrogen atoms forming a naphthene aromatic such as tetralin or tetra.hydronaphthaiLene. ... 

The luminometer index (ASTM D 1740) is a characteristic that is becoming less frequently used. It is determined using the standard lamp mentioned above, except that the lamp is equipped with thermocouples allowing measurement of temperatures corresponding to different flame heights, and a photo-electric cell to evaluate the luminosity. The jet fuel under test is compared to two pure hydrocarbons tetraline and iso-octane to which are attributed the indices 0 and 100, respectively. The values often observed in commercial products usually vary between 40 and 70 the official specification is around 45 for TRO. 

Method 2 by the action of bromine upon tetrahydronaphthalene (tetralin). The reaction may be represented by the equation ... 

A further example is given below illustrating the use of a dibasic anhydride (succinic anhydride) the succinoylation reaction is a valuable one since it leads to aroyl carboxylic acids and ultimately to polynuclear hydrocarbons. This general scheme of synthesis of substituted hydrocarbons through the use of succinic anhydride is sometimes called the Haworth reaction. Thus a-tetralone (see below) may be reduced by the Clemmensen method to tetralin (tetrahydronaphthalene) and the latter converted into naphthalene either catal3d.ically or by means of sulphur or selenium (compare Section, VI,33). 

Commercial tetraUn may be purlfled as follows. Wash the technical pr uct repeatedly with 10 per cent, of its volume of concentrated sulphuric acid, then with 10 per cent, sodium carbonate solution, followed by water, dry with anhydrous calcium sulphate, filter from the desiccant, reflux over sodium, and finally distil from sodium. Collect the pure tetralin at 206-207°. 

Tetralin shows evidence in n.m.r. spectroscopy, similar to that mentioned above, for the formation of one or more addition complexes. Tetralin (like indan) is known to undergo acetoxylation. ... 

There are variations in representation of rings in different disciplines. The dye industry does not designate aromaticity or double bonds in rings. AH double bonds and aromaticity are shown in the Encyclopedia as a matter of course. For example, tetralin has an aromatic ring and a saturated ring and its stmcture appears in the Encyclopedia with its common name. Registry Number enclosed in brackets, and parenthetical CA index name, ie, tetralin [119-64-2] (1,2,3,4-tetrahydronaphthalene). With names and stmctural formulas, and especiaHy with CAS Registry Numbers, the aim is to help the reader have a concise means of substance identification. 

Dihydioxytetiahydionapthacenedione derivatives, used as intermediates for the anthracycline antibiotics have been prepared by Friedel-Crafts reaction of tetralin derivatives with orthophthaloyl chlotide [88-95-9J in high yields (93). 

Eriedel-Crafts reaction of naphthalene or tetrahydronaphthalene derivatives with those of styrene or alkylbenzenes has been used in the preparation of high viscous fluids for traction drive (195). Similarly, Eriedel-Crafts reaction of tetraline and a-methylstyrene followed by catalytic hydrogenation provided l-(l-decalyl)-2-cyclohexyl propane, which is used as a highly heat resistant fluid (196). 

Tetralin. Tetralin is a trade name of Du Pont for 1,2,3,4-tetrahydronapththalene [119-64-2] C qH 2- Tetralin, a derivative of naphthalene, is made by hydrogenating one ring completely and leaving the other unchanged. Tetralin is produced by several manufacturers and is one of the oldest heat-transfer fluids. Tetralin can be used both in Hquid- and vapor-phase systems. The normal boiling point is 207°C. 

Property Tetralin cis Decalin Mixed isomers trans... 

Tetralin and decalin, respectively data from Ref. 24 unless otherwise noted. Ref. 23. 

Tetrahydronaphthalene [119-64-2] (Tetralin) is a water-white Hquid that is insoluble in water, slightly soluble in methyl alcohol, and completely soluble in other monohydric alcohols, ethyl ether, and most other organic solvents. It is a powerhil solvent for oils, resins, waxes, mbber, asphalt, and aromatic hydrocarbons, eg, naphthalene and anthracene. Its high flash point and low vapor pressure make it usehil in the manufacture of paints, lacquers, and varnishes for cleaning printing ink from rollers and type in the manufacture of shoe creams and floor waxes as a solvent in the textile industry and for the removal of naphthalene deposits in gas-distribution systems (25). The commercial product typically has a tetrahydronaphthalene content of >97 wt%, with some decahydronaphthalene and naphthalene as the principal impurities. 

Tetrahydronaphthalene is not a highly toxic compound. A threshold limit value of 25 ppm or 135 mg/m has been suggested for Tetralin. Tetralin vapor is an irritant to the eyes, nose, and throat, and dermatitis has been reported in painters working with it (28). The single-dose oral toxicity LD q for rats is 2.9 g/kg (29). 

Decahydronaphthalene [91-17-8] (Decalin) is the product of complete hydrogenation of naphthalene. Like Tetralin, it is a clear, colorless Hquid with... 

Tetralin, American Petroleum Institute Monograph Series, PubHcation 705, API, Washington, D.C., Oct. 1978. 

Tetralin and Decalin Solvents, Bulletin, E. I. du Pont de Nemours Co. Inc., Organic and Chemicals Division, Wilmington, Del., 1976. 

The most important process to produce 1-naphthalenol was developed by Union Carbide and subsequently sold to Rhc ne-Poulenc. It is the oxidation of tetralin, l,2,3,4-tetrahydronaphthalene/719-64-2] in the presence of a transition-metal catalyst, presumably to l-tetralol—1-tetralone by way of the 1-hydroperoxide, and dehydrogenation of the intermediate ie, l-tetralol to 1-tetralone and aromatization of 1-tetralone to 1-naphthalenol, using a noble-metal catalyst (58). 1-Naphthol production in the Western world is around 15 x 10 t/yr, with the United States as the largest producer (52). 

At room temperature, HDPE is not soluble in any known solvent, but at a temperature above 80—100°C, most HDPE resins dissolve in some aromatic, aflphatic, and halogenated hydrocarbons. The solvents most frequently used for HDPE dissolution are xylenes, tetralin, decalin 1,2,4-trimethylbenzene, o-dichlorobenzene, and 1,2,4-ttichlorobenzene. 

Chemical Properties and Reactivity. LLDPE is a saturated branched hydrocarbon. The most reactive parts of LLDPE molecules are the tertiary CH bonds in branches and the double bonds at chain ends. Although LLDPE is nonreactive with both inorganic and organic acids, it can form sulfo-compounds in concentrated solutions of H2SO4 (>70%) at elevated temperatures and can also be nitrated with concentrated HNO. LLDPE is also stable in alkaline and salt solutions. At room temperature, LLDPE resins are not soluble in any known solvent (except for those fractions with the highest branching contents) at temperatures above 80—100°C, however, the resins can be dissolved in various aromatic, aUphatic, and halogenated hydrocarbons such as xylenes, tetralin, decalin, and chlorobenzenes. 

Above 100°C, most polyolefins dissolve in various aHphatic and aromatic hydrocarbons and their halogenated derivatives. For example, polybutene dissolves in benzene, toluene, decalin, tetralin, chloroform, and chlorobenzenes. As with other polyolefins, solubiHty of PB depends on temperature, molecular weight, and crystallinity. 

---