Decalin physical properties

Table 3 Physical properties of F-octyl bromide (PFOB, 1) and F-decalin (FDC, 6)...

Prior to 1960 the only perhydronaphthalenes for which physical properties were available were the cis and trans isomers of decalin. Soon thereafter, our investigation of the hydrogenation of the two monomethylnaphthalenes led to the isolation, identification, and measurement of the physical properties of all eight of the resulting isomeric monomethyldecalins (5). The 68 dimethyldecalins, obtainable by hydrogenation of the 10 dimethylnaphthalenes, will be described in this contribution... 

Physical properties determined on a few well-spaced and easily isolated dimethyldecalins are listed in Table XXVI. These results, along with similar data on the monomethyldecalins from Table XVII and available data on cis- and retention time. The correlations are good but are probably more valuable for estimating properties than for predicting structures. 

As good examples for the analytical approach for dicyclic terpanes we chose camphane and decalin. Camphane derives from its ketone precursor (i.e. camphor) and decalin is the fully hydrogenated naphthalene. The two bicyclic compounds exhibit large differences in their physical properties and also in their chemical reactivity. The camphane belongs to the bridged bicyclics whereas the decalin is a fused dicycloalkane. Hence in decalin we have cis, trans isomers. In the cis the two hydrogens point in the same direction, whilst in the trans they point in different directions. 

Simple rotations of groups about carbon—carbon bonds do not interconvert cis- and tw r-decalins. They are stereoisomers and they have different physical properties. 

The relationship between these compounds is stereoisomeric (as in the previous section). These two compounds are not interconvertible by ring flipping. They are two diflferent compounds with different physical properties. Many naturally occurring compoimds, such as steroids, incorporate decalin systems into their structures. Steroids are a class of compoimds comprised of four fused rings (three six-membered rings and one five-membered ring). Below are two examples of steroids ... 

Polymer materials possess varying physical and structural properties dependent upon the route of synthesis and polymerization, as was discussed in Section 4.1. Properties also depend upon their actual physical form or state. The as prepared samples obtained by chemical polymerization are in the state of powder. Polymer films are prepared by dissolving the powder in an appropriate organic solvent and then letting the solution dry by slow evaporation. Common solvents with poly(alkylthiophene)s are chloroform, tetrachlormethane, toluene, tetrahydrofuran, decaline, anisole, thiophene and some others, whereas acetone. 

Chemical Designations — Synonyms Bicyclo [4.4.0] Decane Naphthalane Perhydronaphthlene Dec Decalin De Kalin Naphthane sic- or trans-Decahydronaphthalene Chemical Formula C,oH,g. Observable Characteristics — Physical State (as normally shipped) Liquid Color Colorless Odor Aromatic, like turpentine mild, characteristic. Physical and Chemical Properties — Physical State at 15"C and 1 atm. Liquid Molecular Weight 138.2 Boiling Point at 1 atm. 383, 195, 468 Freezing Point -44, -42, 231 Critical Temperature Not pertinent Critical Pressure Not pertinent Specific Gravity 0.89 at 20 C (liquid) Vapor (Gas) Density Not pertinent Ratio of Specific Heats of Vapor (Gas) Not pertinent Latent Heat of Vaporization 130, 71, 3.0 Heat of Combustion -19,200, -10,700, -447 Heat of Decomposition Not pertinent. Health Hazards Information — Recommended Personal Protective Equipment Air mask or self-... 

---