| Identification | More | [Name]
Decahydronaphthalene | [CAS]
91-17-8 | [Synonyms]
DECAHYDRONAPHTHALENE
DECALIN
DECALINE
DECALIN(R)
DEKALIN
NAPHTHALANE
NAPHTHANE
PERHYDRONAPHTHALENE
Bicyclo(4,4,0)decane
bicyclo(4.4.0)decane
bicyclo(4.4.o)decane
Bicyclo[4.4.0]decane
Bicyclo[4.4.0]decane(mixtureofcis/transisomers)
decahydro-naphthalen
Decahydronaphthalene,c&t
decahydronaphthalene,mixtureofcisandtrans
Decalin,c&t
Decanhydronaphthalene
Dekalina
dekalina(polish) | [EINECS(EC#)]
202-046-9 | [Molecular Formula]
C10H18 | [MDL Number]
MFCD00004130 | [Molecular Weight]
138.25 | [MOL File]
91-17-8.mol |
| Chemical Properties | Back Directory | [Appearance]
colourless liquid | [Melting point ]
−125 °C(lit.)
| [Boiling point ]
189-191 °C(lit.)
| [density ]
0.896 g/mL at 25 °C(lit.)
| [vapor density ]
4.76 (vs air)
| [vapor pressure ]
42 mm Hg ( 92 °C)
| [refractive index ]
n20/D 1.474(lit.)
| [Fp ]
57 °C
| [storage temp. ]
Store below +30°C. | [solubility ]
0.006g/l (experimental) | [form ]
Liquid | [color ]
Clear | [Odor]
Aromatic, like turpentine; mild, characteristic. | [Stability:]
Stable. Incompatible with oxidizing agents. Combustible. May form explosive peroxides. Heat and light accelerate peroxide formation. | [explosive limit]
0.7-4.9%, 100°F | [Water Solubility ]
6 mg/L at 20 ºC | [Sensitive ]
Hygroscopic | [Merck ]
14,2846 | [BRN ]
878165 | [Henry's Law Constant]
7.00, 8.37, 10.6, 11.7, and 19.9 (x 10-2 atm?m3/mol) at 10, 15, 20, 25, and 30 °C, respectively (EPICS, Ashworth et al.,
1988) | [Dielectric constant]
2.2（20℃） | [InChIKey]
NNBZCPXTIHJBJL-UHFFFAOYSA-N | [LogP]
4.2 | [CAS DataBase Reference]
91-17-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Naphthalene, decahydro-(91-17-8) | [EPA Substance Registry System]
91-17-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C,N,Xi | [Risk Statements ]
R20:Harmful by inhalation.
R34:Causes burns.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S24/25:Avoid contact with skin and eyes .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . | [RIDADR ]
UN 1147 3/PG 3
| [WGK Germany ]
1
| [RTECS ]
QJ3150000
| [Autoignition Temperature]
482 °F | [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29021990 | [Safety Profile]
Moderately toxic by
inhalation and ingestion. Questionable
carcinogen with experimental carcinogenic
and neoplastigenic data. Mildly toxic by skin
contact. Human systemic effects by
inhalation: conjunctiva irritation, unspecified
olfactory and pulmonary system changes.
Can cause kidney damage. Mutation data
reported. A skin and eye irritant. Flammable
liquid when exposed to heat or flame, can
react with oxidzing materials. To fight fire,
use foam, CO2, dry chemical. When heated
to decomposition it emits acrid smoke and
fumes. | [Hazardous Substances Data]
91-17-8(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 4.2 g/kg; LC (in air) in rats: 500 ppm (Smyth) |
| Hazard Information | Back Directory | [General Description]
A clear colorless liquid with an aromatic odor. Flash point 134°F. Less dense than water and insoluble in water. Vapors heavier than air. | [Reactivity Profile]
Saturated aliphatic hydrocarbons, such as DECAHYDRONAPHTHALENE(91-17-8), may be incompatible with strong oxidizing agents like nitric acid. Charring of the hydrocarbon may occur followed by ignition of unreacted hydrocarbon and other nearby combustibles. In other settings, aliphatic saturated hydrocarbons are mostly unreactive. They are not affected by aqueous solutions of acids, alkalis, most oxidizing agents, and most reducing agents. Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154]. | [Air & Water Reactions]
Flammable. Insoluble in water. | [Health Hazard]
Inhalation or ingestion irritates nose and throat, causes numbness, headache, vomiting; urine may become blue. Irritates eyes. Liquid de-fats skin and causes cracking and secondary infection; eczema may develop. | [Fire Hazard]
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. | [Chemical Properties]
colourless liquid | [Physical properties]
Clear, colorless, flammable liquid with a mild methanol or hydrocarbon-like odor | [Uses]
Solvent for naphthalene, fats, resins,
oils; alternate for turpentine in lacquers, shoe
polishes, and waxes; component in motor fuels
and lubricants | [Uses]
Solvent for naphthalene, waxes, fats, oils, resins, rubbers; motor fuel and lubricants;
cleaning machinery; substitute for turpentine; shoe-creams; stain remover. | [Definition]
ChEBI: An ortho-fused bicyclic hydrocarbon that is the decahydro- derivative of naphthalene. | [Production Methods]
Decalin occurs naturally in crude oil and is produced commercially
by the catalytic hydrogenation of naphthalene. It is also a
product of combustion and is released from natural fires. | [Chemical Reactivity]
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. | [Environmental Fate]
Photolytic. The following rate constants were reported for the reaction of decahydronaphthalene
and OH radicals in the atmosphere: 1.96 x 10-11 and 2.02 x 10-11 cm3/molecule?sec at 299 K for cis
and trans isomers, respectively (Atkinson, 1985). A photooxidation reaction rate constant of 2.00
x 10-11 was reported for the reaction of decahydronaphthalene (mixed isomers) and OH radicals in
the atmosphere at 298 K (Atkinson, 1990).
Chemical/Physical. Decahydronaphthalene will not hydrolyze because it has no hydrolyzable
functional group. | [Purification Methods]
Then the organic phase is separated, washed with water, saturated aqueous Na2CO3, again with water, dried with CaSO4 or CaH2 (and perhaps dried further with Na), filtered and distilled under reduced pressure (b 63-70o/10mm). It has also been purified by repeated passage through long columns of silica gel previously activated at 200-250o, followed by distillation from LiAlH4 and storage under N2. Type 4A molecular sieves can be used as a drying agent. Storage over silica gel removes water and other polar substances. [For the separation of cis and trans isomers see Seyer & Walker J Am Chem Soc 60 2125 1938, and Baker & Schuetz J Am Chem Soc 69 1250 1949.] |
| Questions And Answer | Back Directory | [Description]
Decahydronaphthalene also referred to as Decalin is an organic compound that dissolves rubber, resins, waxes, fats, and oils. It is a colorless, aromatic hydrocarbon which is used as an alternative to turpentine, as a cleaning fluid and as a stain remover. Decahydronaphthalene was also used as a varnish remover for oil-based paintings in the past.
| [Chemical and Physical Properties]
Decahydronaphthalene has a molecular weight of 138.254 g/mol, a monoisotopic mass of 138.141 g/mol and an exact mass of 138.141 g/mol. It has a heavy atom count of 10 and a complexity of 80.6. It is a clear, colorless liquid with a characteristic odor that resembles that of methanol.
Decahydronaphthalene has a flash point of 134°F and it is less dense than water. It indicates poor solubility in water at 250℃ and its vapours are denser than air. It has a density of 0.89 at 68°F220℃.
Decalin is very soluble in chloroform, ether, methanol and alcohol, and it is miscible with isopropyl alcohol, propyl, esters and a majority of the ketones. Decalin has a boiling point of 383/ 155.50℃ at 760 mm Hg and a melting point of -44°F -40°C.
After long periods of exposure, Decalin forms toxic concentrations of peroxides. When Decalin is heated to decomposition, it released acrid fumes and smoke.
| [Preparation]
Decahydronaphthalene is prepared by the hydrogenation of tetralin at low pressure with rhodium as the catalyst. Decalin can be oxidized to yield a significant amount of the hydroperoxide derivative. The cis isomer of Decahydronaphthalene can be oxidized at a higher rate than the combination of the trans and cis isomers, or the trans isomer solely. Therefore, when Decahydronaphthalene is synthesized through the hydrogenation of an unsaturated homolog such as 1,2,3,4-tetrahydronaphthalene for application in the synthesis of hydroperoxide, the resulting product is made of the cis isomer primarily. This method results in Decahydronaphthalene that is saturated with the cis isomer. Such high-pressure processes are technical to execute, and they are relatively expensive. A low-pressure preparation process that entails the hydrogenation of tetralin to obtain cis Decahydronaphthalene is yet to be developed.
The rhodium catalyst is maintained on an inert support such as carbon or alumina, and the reaction is best conducted in the presence of a solvent, which may include a lower saturated carboxylic acid such as acetic acid. Other solvents such as propionic acid, mineral acids and non-acid solvents which may consist of water, hydrocarbons, ethers, esters, amines, amides and alcohol can also be used. The portion of the solvent should be one in which the reaction apparatus can withstand, while in some instances it may be best to omit the solvent. Acetic acid yields a higher rate of the cis isomer when it is applied as the solvent as opposed to the application of alumina as the support substance for the catalyst. The rhodium catalyst is applied as the hydrogenation catalyst, and it is best prepared through reduction of rhodium salts, which may include oxide or chloride. The progress of the hydrogenation reaction may depend on the quantity of the rhodium catalyst applied to the reaction. The tetralin to rhodium ratio is also dependent on the positioning of rhodium with an inert support, the configuration of the support and the apparatus used during the hydrogenation process. For instance, if the rhodium catalyst on an inert support such as carbon or alumina is about 5%, the reaction will yield satisfactory results. Furthermore, approximately 12-25g of the catalyst per mole of the Tetralin may result in satisfactory results. The optimum temperatures for this reaction are 50 C but the rate of the reaction may increase if the temperature is increased gradually from approximately 200 C250 C. The main advantage of this method is the fact that it can be conducted under low pressures of hydrogen, which may be as low as 0.5 atmospheres. Based on the above catalyst concentrations and reaction conditions, the total conversion of tetralin to Decahydronaphthalene may be obtained in about 1-2 hours. This reaction also yields the cis isomer which could be more than 90% of the product, which is relative to the total hydrogenation process which may be ascertained by the absorption of the theoretical amount of hydrogen by tetralin. To attain the desired cis Decahydronaphthalene, the reaction contents should be passed through a conventional fractional distillation to remove any trans isomers. It is fundamental to exercise care while conducting the distillation process using a basic packed column to yield a chromatographically pure cis Decahydronaphthalene.
| [Hazard Statements]
Decalin is a flammable liquid, and it may also cause acute toxicity upon inhalation. It may cause skin irritation/corrosion upon contact as well as severe eye irritation/damage.
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