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Home > Encyclopedia > Decalin

Decalin

Decalin structure

Decalin 

structure
  • CAS No:

    91-17-8

  • Formula:

    C10H18

  • Chemical Name:

    Decalin

  • Synonyms:

    Naphthalene,decahydro-;Decahydronaphthalene;Bicyclo[4.4.0]decane;Dec;Naphthan;Perhydronaphthalene;Decalin;Dekalin;Decaline;NSC 406139

  • Categories:

    Analytical Chemistry  >  Standard

Description

colourless liquid


Decahydronaphthalene appears as a clear colorless liquid with an aromatic odor. Flash point 134°F. Less dense than water and insoluble in water. Vapors heavier than air.|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.


Decahydronaphthalene appears as a clear colorless liquid with an aromatic odor. Flash point 134°F. Less dense than water and insoluble in water. Vapors heavier than air.|Decalin is an ortho-fused bicyclic hydrocarbon that is the decahydro- derivative of naphthalene. It has a role as a solvent.

Decalin Basic Attributes

138.25

138.25

878165

202-046-9

88451Q4XYF

1548

406139|77453|77452

1147

DTXSID1024912

Clear colorless liquid|Water-white liquid

29021990

Characteristics

0

4.6

Clear Liquid

0.8965 g/cm3 @ Temp: 22 °C

-43 °C

155.5 °C

57 °C

n20/D 1.474(lit.)

H2O: 6 mg/L at 20 ºC

Store below +30°C.

42 mm Hg ( 92 °C)

4.76 (vs air)

Oral-Rat LD50: 4170 mg/kg

Combustible in case of open flame, high temperature, strong oxidant; burning emits irritating smoke

0.7-4.9%, 100°F

Slight odor resembling menthol; pure decalin does not smell of naphthalene

2.01e-11 cm3/molecule*sec

MP: -42.9 °C; BP: 195.8 °C; density: 0.8999 @ 20 °C; index of refraction: 1.4695 @ 20 °C; insoluble in water; miscible in ethanol; very soluble in ethyl ether, acetone, benzene; chloroform /cis-Form/|MP: -30.3 °C; BP: 187.3 °C; density: 0.8965 @ 20 °C; index of refraction: 1.4810 @ 20 °C; insoluble in water; miscible in ethanol; very soluble in ethyl ether, acetone; miscible in benzene /trans-Form/|Air pollution factors: 1 mg/cu m = 0.17 ppm, 1 ppm = 5.75 mg/cu m|Conversion factors: 1 ppm= 5.65 mg/cu m|Volatile with steam|Heat of vaporization: 41.0 kJ/mol /Cis-isomer/|Heat of vaporization: 40.2 kJ/mol /Trans-isomer/|Enthalpy of formation: -52.45 kcal/mol; Gibbs energy of formation: 16.47 kcal/mol; Entropy: 63.34 kcal/mol; Heat capacity: 55.45 kcal/mol /Cis-isomer/|Enthalpy of formation: -55.14 kcal/mol; Gibbs energy of formation: 13.79 kcal/mol; Entropy: 63.32 kcal/mol ; Heat capacity: 54.61 kcal/mol /Trans-isomer/|Viscosity: 2.99 cP @ 25 °C /Cis-isomer/; 1.936 cP @ 25 °C /Trans-isomer/|For more Other Experimental Properties (Complete) data for DECAHYDRONAPHTHALENE (10 total), please visit the HSDB record page.

Flammable. Insoluble in water.

Hydrocarbons, Aliphatic Saturated

Highly Flammable

Saturated aliphatic hydrocarbons, such as DECAHYDRONAPHTHALENE, 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].

Decahydronaphthalene (decalin)|B: Compounds that form peroxides on concentration (distillation/evaporation)|Kelly

482 °F (USCG, 1999)|482 °F; 250 °C (491 °F; 255 °C /Trans-isomer/)|255 °C

-19,200 BTU/lb= -10,700 cal/g= -447x10+5 J/kg

LOWER 0.7% @ 100 °C; UPPER 4.9% @ 100 °C|LOWER 0.7%; UPPER 5.4% /TRANS-ISOMER/

As a result of flow, agitation, etc., electrostatic charges can be generated.

130 BTU/lb= 71 cal/g= 3.0x10+5 J/kg

Safety Information

III

3

UN 1147 3/PG 3

1

20-34-51/53-36/37/38-65

26-36/37/39-45-60-24/25-23-62-61

QJ3150000

C,N,Xi

Complete packaging, light loading and unloading; warehouse ventilated, away from open flame, high temperature, and stored separately from oxidant

Explosive when mixed with air

Stable. Incompatible with oxidizing agents. Combustible. May form explosive peroxides. Heat and light accelerate peroxide formation.

P261-P273-P280-P301 + P310-P305 + P351 + P338-P310

H226-H304-H314-H331-H411

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

... Can react with oxidizing materials.

SCHMELTZ I ET AL; VOL 3, POLYNUCLEAR AROMATIC HYDROCARBONS. SECOND INTERNATIONAL SYMPOSIUM ON ANALYSIS, CHEMISTRY, & BIOLOGY. SEPT 1977, ISBN 0-89004-241-1: 47-60 (1978). BIOASSAYS OF NAPHTHALENE FOR COCARCINOGENIC ACTIVITY RELATION TO TOBACCO CARCINOGENESIS WAS DISCUSSED. /NAPHTHALENE & ALKYL NAPHTHALENES/|WHO; Environmental Health Criteria 119: Principles and Methods for the Assessment of Nephrotoxicity Associated with Exposure to Chemicals (1991)

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: 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. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016)|Flammable. Above 57 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree

|Danger|H226 (85.66%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P273, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P311, P312, P321, P331, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 279 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P273, P280, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P363, P370+P378, P391, P403+P235, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P284, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P314, P320, P321, P331, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Air mask or self-contained breathing apparatus if in enclosed tank; rubber gloves or protective cream; goggles or face shield. (USCG, 1999)|Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles.|/NIOSH approved respirators/ ... or self contained breathing apparatus if in enclosed tank; ... protective cream ... face shield.

MODERATE, WHEN EXPOSED TO HEAT OR FLAME ...

0.7-4.9%|May form explosive peroxides.|Explosive limits , vol% in air: 0.7-5.4

TO FIGHT FIRE USE FOAM, CARBON DIOXIDE, DRY CHEMICAL.|If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock down vapors.|Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/Noxious)/ Fire or Explosion: 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. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.|/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/Noxious)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.|/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/Noxious)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.|/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/Noxious)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.|For more DOT Emergency Guidelines (Complete) data for DECAHYDRONAPHTHALENE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Decalin is irritating to the eyes, skin, and mucous membranes ...

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Ventilation. Collect leaking liquid in sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Fireproof. Separated from oxidants. Cool. Keep in the dark. Well closed.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is corrosive to the skin and eyes. The vapour is irritating to the respiratory tract. The substance may cause effects on the central nervous system. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis.

Repeated or prolonged contact with skin may cause dermatitis.

NO open flames, NO sparks and NO smoking. Above 57 °C use a closed system, ventilation and explosion-proof electrical equipment. Prevent build-up of electrostatic charges (e.g., by grounding).

PREVENT GENERATION OF MISTS!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.

The major hazards encountered in the use and handling of decahydronaphthalene stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal absorption), exposure to this clear, colorless, slightly menthol-smelling liquid may occur from its use as a chemical intermediate, in the manufacture of paints, lacquers, varnishes, shoe creams, and floor waxes, rubber, asphalt, and printing inks. Effects from exposure may include contact burns to the skin and eyes, irritation of the mucous membranes, defatting dermatitis and eczema (from prolonged or repeated contact), numbness, headache, CNS depression (dizziness), vomiting, and fatal chemical pneumonitis (if the liquid is aspirated). In activities and situations where over-exposure may occur, wear a self-contained breathing apparatus and chemical protective clothing. If contact should occur, immediately flush affected eyes and skin with running water for at least 15 minutes. Remove contaminated clothing and shoes at the site. This material may be ignited by heat, sparks, or flames. Further, its heavier than air vapor may travel to a source of ignition and flash back. Containers may explode in the heat of a fire. For fires involving decahydronaphthalene, extinguish with dry chemical, CO2, Halon, water spray, fog, or standard foam. Isolate for 1/2 mile in all directions if a tank car or truck is involved in the fire. Decahydronaphthalene may be shipped domestically via air, rail, road, or water. Storage should be away from sources of ignition and oxidizing materials. Also, avoid prolonged exposure of this substance to air because of the possible formation of dangerous peroxides. Take up small spills of decahydronaphthalene with sand or other noncombustible absorbent and place into containers for later disposal. Dike far ahead of large spills to prevent decahydronaphthalene from entering confined spaces such as sewers where its vapor may create an explosion hazard. Before implementing land disposal of waste decahydronaphthalene, consult with environmental regulatory agencies for guidance.

Data from September 2, 1979 identified decahydronaphthalene as a gaseous emission of the vehicle traffic through the Allegheny Mountain Tunnel of the Pennsylvania Turnpike(1). Decahydronaphthalene was detected in the municipal wastewaters from sewage treatment plants in Falmouth, MA(2).

SEDIMENT: Sediment cores from rural Larto Lake, Catahoula Parish and urban/suburban Lac des Allemands, Barataria Basin in Louisiana were analyzed for pollutant deposition over the years 1950 through 1991(1). Decaydronaphthalene concns in Larto Lake ranged from not detected to 3.4 ng/g and in Lac des Allemands, not detected to 9.2 ng/g(1).

URBAN/SUBURBAN: Decahydronaphthalene was detected not quantified in the ambient air of Paris, France in 1972(1).|SOURCE DOMINATED: Data from September 2, 1979 identified decahydronaphthalene as an air pollution contaminant in the Allegheny Mountain Tunnel of the Pennsylvania Turnpike(1).

Toxicity

moderately toxic

LD50 Rabbit dermal 5900 mg/kg|LD50 Rat oral 4.2 g/kg|LC50 Rat inhalation 710 ppm/4 hr

/AQUATIC SPECIES/ Mussel larvae (Mytilus edulis) /showed a/ 20% reduction of growth rate at 10 ppm and 50 ppm; /also a/ 5% reduction of growth rate at 100 ppm.|/AQUATIC SPECIES/ ...The growth rate of the fungus Cladosporium resinae, which was cultured on a 10 mmolar solution of dodecane, was inhibited by about 60% in the presence of 138 mg decahydronaphthalene; and effect on the biomass yield per gram dodecane was not observed. ...

Decahydronaphthalene is a natural component of petroleum naphtha(1).

Decahydronaphthalene's production and use as a solvent, in motor fuels and lubricants, and as a substitute for turpentine in various consumer products(1) may result in its release to the environment through various waste streams(SRC).|Decahydronaphthalene is emitted to the environment by effluents from petroleum refining and coal tar distillation(1). The combustion of gasoline and diesel fuels releases decahydronaphthalene to the atmosphere(2). The compound has been detected in emissions from unvented kerosene space heaters at rates of 43, 150, and 3 ng/kJ from two radiant and one maltuned convective space heaters, respectively(3).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,600(SRC), determined from a water solubility of 0.889 mg/l(2) and a regression-derived equation(3), indicates that decahydronaphthalene is expected to have slight to no mobility in soil(SRC). Volatilization of decahydronaphthalene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant estimated as 0.47 atm-cu m/mole(SRC) derived from its vapor pressure, 2.3 mm Hg(4), and water solubility, 0.889 mg/l(2). The potential for volatilization of decahydronaphthalene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 2.3 mm Hg(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Decahydronaphthalene was not degraded using sediment grab samples from an oiled and pristine beach areas and mud from an intertidal zone(5), indicating that biodegradation may not be an important fate process in soil.|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,600(SRC), determined from a water solubility of 0.889(2) and a regression-derived equation(3), indicates that decahydronaphthalene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant estimated as 0.470 atm-cu m/mole(SRC), derived from its vapor pressure, 2.3 mm Hg(4), and water solubility(2). Using this Henry's Law constant and an estimation method(3), estimated volatilization half-lives for a model river and model lake are 3.5 hrs and 5 days, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 28 days if adsorption is considered(5). According to a classification scheme(6), BCF's of 839-2,380 for the cis-isomer and 1,170-3,050 for the trans-isomer(7), suggest the potential for bioconcentration in aquatic organisms is very high(SRC). That decahydronaphthalene was not degraded using marine water but was degraded in water from a stagnant pond that had been acclimated to oil(8) indicates that biodegradation may be an important fate process in acclimated aquatic environments.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), decahydronaphthalene, which has a vapor pressure of 2.3 mm Hg at 25 °C(2), is expected to exist primarily as a vapor in the ambient atmosphere. Vapor-phase decahydronaphthalene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 19 hrs(SRC), calculated from its rate constant of 2.02X10-11 cu cm/molecule-sec at 25 °C(3).

The rate constant for the vapor-phase reaction of decahydronaphthalene with photochemically-produced hydroxyl radicals is 2.02X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 19 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Decahydronaphthalene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption by cyclic alkanes in the environmental UV spectrum (>290 nm)(3).

1.76e+03|An estimated BCF of 660 was calculated for decahydronaphthalene(SRC), using a water solubility of 0.889 mg/l(1) and a regression-derived equation(2). Over a test period of 8 weeks and using orange-red killifish (Oryzias latipes), BCF's of 839-2,380 at a test concn of 2.1 mg/l and 1,290-2,400 at a test concn of 0.21 mg/l were measured for the cis-isomer; BCF's of 1,170-3,050 at a test concn of 2.8 mg/l and 1,300-2,510 at a test concn of 0.28 mg/l were measured for the trans-isomer(3). According to a classification scheme(4), these BCF values suggest the potential for bioconcentration in aquatic organisms is very high(SRC).

4.68e+03 L/kg|The Koc of decahydronaphthalene is estimated as 4,600(SRC), using a water solubility of 0.889 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that decahydronaphthalene is expected to have slight mobility in soil.

The Henry's Law constant for decahydronaphthalene is estimated as 0.47 atm-cu m/mole(SRC) derived from its vapor pressure, 2.3 mm Hg(1), and water solubility, 0.889 mg/l(2). This Henry's Law constant indicates that decahydronaphthalene is expected to volatilize rapidly from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 3.5 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 5 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 28 days if adsorption is considered(4). Decahydronaphthalene's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of decahydronaphthalene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 2.3 mm Hg(1).

GROUND WATER: Decahydronaphthalene was identified in ground water contaminated by a sewage treatment facility at Falmouth, MA(1).|DRINKING WATER: Decahydronaphthalene was listed as a contaminant found in drinking water in Tuscaloosa, AL(1).|SURFACE WATER: Decahydronaphthalene is listed as a contaminant of coastal waters off Narragansett Bay, RI(1) and Los Angeles River storm waters(2).

Decahydrohapthalene was identified, not quantified in floured chickpea seed (Cicer arietinum L.)(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 249 workers (74 of these are female) are potentially exposed to decahydronaphthalene in the US(1). Occupational exposure to decahydronaphthalene may occur through inhalation and dermal contact with this compound at workplaces where decahydronaphthalene is produced or used(SRC). Monitoring data indicate that the general population may be exposed to decahydronaphthalene via inhalation of ambient air and air in the vicinity of kerosene space heaters, ingestion of contaminated drinking water, and thru use of consumer products containing this compound(SRC).

Drug Information

Decalin is metabolized and excreted in the urine conjugated with glucuronic acid.|...Studies were conducted using decalin (mixture of cis and trans isomers) to (1) characterize systemic elimination of decalin in rats and mice and (2) evaluate disposition of decalin, its metabolites, and kidney alpha2u-globulin in young and old rats of both sexes following a single 6 hr whole-body inhalation exposure at up to 400 ppm decalin. Additionally, a separate group of young male F344/N rats were administered either cis- or trans-decalin iv at doses up to 20 mg/kg to assess disposition of each isomer, its metabolites, and kidney alpha2u-globulin. Decalin was eliminated from blood in a dose-dependent manner, regardless of sex, age, or species. C0 and AUC infinity increased supra-proportionally with exposure concentration. Mice were more efficient in eliminating decalin than rats at lower exposure concentrations, but nonlinear elimination kinetics were more noticeable at 400 ppm. Sex differences in blood decalin elimination were observed in rats; females had a consistently higher AUC infinity at all exposure concentrations. ...

Both cis- and trans-decalin gave rise in the rabbit to racemic decanols, which were excreted in the urine, conjugated with glucuronic acid. /cis- and trans- isomers/|The metabolism of naphthalene in mammals has been extensively studied. Naphthalene is first metabolized by hepatic mixed function oxidases to the epoxide, naphthalene-1,2-oxide. This epoxide has the distinction of being the first arene oxide metabolite to have been isolated. Epoxide formation is an obligatory step. The epoxide can be enzymatically converted into the dihydrodiol, 1,2-dihydroxy-1,2-dihydronaphthalene or conjugated with glutathione. The dihydrodiol can then be conjugated to form a polar compound with glucuronic acid or sulfate or be further dehydrogenated to form the highly reactive 1,2-dihydroxynaphthalene. This too can be enzymatically conjugated with sulfate or glucuronic acid or spontaneously oxidized to form another highly reactive compound, 1,2-naphthoquinone. /Naphthalene/|...There was a dose-dependent increase in kidney decalin, decalone, and alpha2u-globulin in male rats exposed to decalin. Kidney alpha2u-globulin and decalone concentrations in old male rats were substantially lower than those in young males, but were similar to those observed in all (young and old) females. Compared to old males and all females, young male rats had significantly lower urinary decalol concentrations, but higher kidney decalin, decalone, and alpha2u-globulin concentrations. Administration of decalin to male rats as either the cis or trans isomer revealed that more cis -decalone is produced per unit dose as compared to trans-decalone, and that more trans-decalin accumulated in the kidney (as alpha2u-globulin-ligand complexes) compared to cis-decalin. These patterns of isomer-specific metabolism were also reflected in the cis/trans ratios of decalin in blood, as well as urinary decalol metabolites. The ratio of alpha2u-globulin to the total amount of decalin plus decalone measured in the male rat kidney was approximately 1.0. Therefore, alpha2u-globulin was a key factor in the accumulation of decalin and decalone in kidneys of young male rats, decalin and decalone were practically absent in all females and in old males.|After administration of cis- or trans-decahydronaphthalene, cis,trans-1-decalol and cis,cis-2-decalol or trans,cis-2-decalol were found in the urine of female and male rats, with cis,cis-1-decalol or trans,trans-1-decalol additionally detected in the urine of male rats. The hydroxylated metabolites were present in the urine in either glucuronidized or sulfatized form.

A diverse group of chemicals including... decalin... cause alpha2u-globulin nephropathy or hyaline droplet nephropathy. This nephropathy occurs in male rats, is characterized by the accumulation of protein droplets in the S2 segment of the proximal tubule, and results in single-cell necrosis, the formation of granular casts at the junction of the proximal tubule and the thin loop of Henle, and cellular regeneration. Chronic exposure to these compounds results in progression of these lesions and ultimately in chronic nephropathy.|...Several strains of male rats that produce alpha2u-globulin (Fischer-344, Sprague-Dawley, Buffalo, and Norway Brown) demonstrate spontaneous renal cortical hyaline droplets which are exacerbated after exposure to decalin. In all cases, a close correlation exists between hyaline droplet formation observed histologically and alpha 2u-globulin accumulation measured biochemically. In stark contrast, the NCI-Black-Reiter strain, which does not produce measurable quantities of alpha 2u-globulin, neither forms hyaline droplets nor accumulates any filtered protein in its kidney cortex either spontaneously or after exposure to decalin. Also, female rats injected ip with male rat alpha 2u-globulin exhibit increased hyaline droplet formation and alpha 2u-globulin accumulation when treated with decalin. ...

... The major impurity ... 1,2,3,4-tetrahydronaphthalene. /Commercial product/

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. (USCG, 1999)

INHALATION: remove to fresh air. EYES: flush with water for at least 15 min. SKIN: wash with water and mild soap. INGESTION: give emetic such as warm salt water, followed by a mild cathartic; direct physician to conserve liver and kidney function. (USCG, 1999)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Naphthalene and Related Compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Start an IV with lactated Ringer's. Adequate hydration must be maintained to prevent renal failure secondary to myoglobinuria unless signs of cerebral or pulmonary edema are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Naphthalene and related compounds/|Maintain an open air way and assist ventilation if necessary. Treat coma and seizures if they occur. Treat hemolysis and resulting hemoglobinuria if they occur by intravenous hydration and urinary alkalinization. There is no specific antidote. Administer activated charcoal if available. Do not induce vomiting, because of the risk of lethargy and seizures. Do not administer milk, fats or oils, which may enhance absorption|NAPHTHALENE toxicosis caused by vapor inhalation can usually be managed simply by removing the individual to fresh air. Skin contamination should be removed promptly by washing with soap and water. Eye contamination should be removed by flushing with copious amounts of clear water. Irritation may be severe, and if it persists, should receive medical attention. SRP: /It may be helpful to empty stomach and administer dose of activated charcoal/ Examine the plasma for evidence of hemolysis: a reddish-brown tinge. Examine the blood smear for "ghosts" and Heinz bodies. If /hemolysis is/ present, monitor red blood cell count and hematocrit for anemia, urine for protein, and cells. Measure direct- and indirect-reacting bilirubin in the plasma. Monitor fluid balance and blood electrolytes. If possible, monitor urinary excretion of naphthol to assess severity of poisoning and clinical progress. If hemolysis is clinically significnt, administer intravenous fluids to accelerate urinary excretion of the naphthol metabolite and protect the kidney from products of hemolysis. Use Ringer's-lactate or sodium bicarbonate to keep urine pH above 7.5. Consider use of mannitol, or furosemide, to promote diuresis. If urine flow declines, intravenous infusions must be carefully monitored to avoid fluid overload. Institute hemodialysis. Consider charcoal hemoperfusion in tandem to extract naphthalene and end-products. If anemia is severe, blood transfusions may be needed. Hydrocortisone may be of some benefit if significant hemolysis is present. /Fumigant poisoning/

/HUMAN EXPOSURE STUDIES/ Dermatitis and conjunctival irritation. systemic toxicity is not well defined but no serious industrial poisonings are known.|/HUMAN EXPOSURE STUDIES/ Liq alicyclic hydrocarbons will dehydrate & delipidize the skin on ... contact & cause dermatitis. Direct contact ... with lung tissue (aspiration) will cause pulmonary edema, pneumonitis, & hemorrhage. The vapors in sufficient concn will cause irritation of mucous membranes. /alicyclic hydrocarbons/|/HUMAN EXPOSURE STUDIES/ A brownish green urine was reported in workers exposed to a mixture of decalin and tetralin.|/HUMAN EXPOSURE STUDIES/ Excessive exposure to high concn causes numbness, nausea, headache, and vomiting.|For more Human Toxicity Excerpts (Complete) data for DECAHYDRONAPHTHALENE (6 total), please visit the HSDB record page.

decahydronaphthalene

The substance can be absorbed into the body by inhalation of its vapour.

Cough. Sore throat. Headache. Dizziness. Nausea. Vomiting.


Redness. Pain. Skin burns.


Redness. Pain. Severe deep burns.

Decalin Use and Manufacturing

Methods of Manufacturing

Industrially, naphthalene is catalytically hydrogenated in the presence of a nickel catalyst to obtain an equal mixture of two isomers. If purer isomers are required, industrial-grade decalin can be washed with concentrated sulfuric acid until the acid layer is colorless. Then alkaline wash, water wash, separate water layer, dry with desiccant. Vacuum rectification, in a tower with 130 theoretical plates, the reflux ratio is close to 145:1, and can obtain cis-isomer with a purity of 99.93% (weight); in a tower with 200 theoretical plates, the reflux ratio The ratio is 160:1, and the trans isomer with a purity of 99.97% can be obtained.

Uses

Used as a liquid for refractive index measurement and as a solvent


Fuels and fuel additives


Fuels and related products

GRADE: TECHNICAL.|The commercial product may be practically all trans-Decalin, or a mixture containing up to 60% cis-Decalin.|Grades or purity: ... mixture of cis-(35%) and trans-(65%) isomers. ... Spectro grade.|The commercial product typically has a decahydronaphthalene content > or equal to 97% wt% ... /Commercial product/

All other petroleum and coal products manufacturing|Naphthalene, decahydro-: ACTIVE|Naphthalene, decahydro-, cis-: ACTIVE|Naphthalene, decahydro-, trans-: ACTIVE

Fire Hazards -> Flammable - 2nd degree

Computed Properties

Molecular Weight:138.25
XLogP3:4.6
Exact Mass:138.140850574
Monoisotopic Mass:138.140850574
Heavy Atom Count:10
Complexity:80.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Downstream Products

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