Decalin?
Title: Decalin® (DuPont)
CAS Registry Number: 91-17-8
CAS Name: Decahydronaphthalene
Additional Names: perhydronaphthalene; bicyclo[4.4.0]decane; naphthalane; naphthane
Trademarks: DeKalin
Molecular Formula: C10H18
Molecular Weight: 138.25
Percent Composition: C 86.88%, H 13.12%
Literature References: Occurs in two forms: cis and trans. Hydrogenation of naphthalene in glacial acetic acid in the presence of platinum catalyst at 25° and 130 atm yields a mixture of 77% cis-Decalin and 23% trans-Decalin. Hydrogenation of Tetralin under the same conditions yields almost only cis-Decalin: Baker, Schuetz, J. Am. Chem. Soc. 69, 1250 (1947). Hydrogenation of D4a(8a)-octalin in ethanol in the presence of platinum yields trans-Decalin as the main component: Linstead et al., J. Chem. Soc. 1937, 1136. Separation of trans- and cis-forms: Seyer, Walker, J. Am. Chem. Soc. 60, 2125 (1938). Prepn of trans-Decalin from cis-Decalin: Zelinsky, Ber. 65, 1299 (1932). Conformation studies: Barton, J. Chem. Soc. 1948, 340; Moniz, Dixon, J. Am. Chem. Soc. 83, 1671 (1961). Toxicity data: Smyth et al., Arch. Ind. Hyg. Occup. Med. 4, 119 (1951).
Properties: Liquid. Slight odor resembling menthol. Pure Decalin does not smell of naphthalene. Volatile with steam. The commercial product may be practically all trans-Decalin, or a mixture contg up to 60% cis-Decalin. The commercial mixture has a flash pt (closed cup) of about 136°F (58°C). Autoignition temp 504°F. Insol in water. Very sol in alcohol, methanol, ether, chloroform. Miscible with propyl and isopropyl alcohol; miscible with most ketones and esters. LD50 orally in rats: 4.2 g/kg; LC (in air) in rats: 500 ppm (Smyth).
Flash point: flash pt (closed cup) of about 136°F (58°C)
Toxicity data: LD50 orally in rats: 4.2 g/kg; LC (in air) in rats: 500 ppm (Smyth)
 
Derivative Type: cis-Form
Properties: mp -43.26°. bp 195.7°; bp9 67.0°. d420 0.8963. nD20 1.48113.
Melting point: mp -43.26°
Boiling point: bp 195.7°; bp9 67.0°
Index of refraction: nD20 1.48113
Density: d420 0.8963
 
Derivative Type: trans-Form
Properties: mp -30.4°. bp 187.25°; bp9 62.0°. d420 0.8700. nD20 1.46968.
Melting point: mp -30.4°
Boiling point: bp 187.25°; bp9 62.0°
Index of refraction: nD20 1.46968
Density: d420 0.8700
 
Use: Solvent for naphthalene, fats, resins, oils, waxes; used instead of turpentine in lacquers, shoe polishes, floor waxes. In motor fuel and lubricants. As patent fuel in stoves.

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