Decalin

Other Classes -> Naphthalenes

Other Classes -> Naphthalenes

Other Classes -> Naphthalenes

Flammable agents - 2nd degree

0.89 at 68 °F (USCG, 1999) - Less dense than water; will float

0.8965 @ 22 °C

Vapor density: 4.77 (air= 1) /Trans-isomer/

Liquid water interfacial tension: 51.5 dynes/cm= 0.0515 N/m at 20 °C; liquid heat capacity= 0.391 BTU/lb-deg F @ 70 °F; liquid thermal conductivity= 0.735 BTU-in/hr-sq ft-deg F at 135 °C; saturated vapor density= 0.00269 lb/cu ft @ 130 °F

Relative density (water = 1): 0.87-0.90

0.8965 @ 22°C

Clear colorless liquid

Water-white liquid

Very sol in alcohol, methanol, ether, chloroform. Miscible with propyl and isopropyl alcohol; miscible with most ketones and esters.

In water, 0.889 mg/l @ 25 °C

Solubility in water at 25 °C: very poor

134 °F (USCG, 1999)

134 deg. F

129 °F; 54 °C (Closed cup) /Trans-isomer/

136 °F; 58 °C (CLOSED CUP)

57 °C c.c.

383 °F at 760 mmHg (USCG, 1999)

155.5 °C

185-195 °C

155.5 °C @760 [mm Hg]

-44 °F (USCG, 1999)

-43 °C

-40 °C

-43 °C

Danger

H226 (87.3%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P271, P273, P280, P301+P316, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P331, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 315 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H226 (97.7%): Flammable liquid and vapor [Warning Flammable liquids]

Chemical: Naphthalene, decahydro-

Chemical: Naphthalene, decahydro-, cis-

Chemical: Naphthalene, decahydro-, trans-

Naphthalene, decahydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Naphthalene, decahydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 06-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/10843

cis-Decahydronaphthalene: Does not have an individual approval but may be used under an appropriate group standard

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Above 57 °C explosive vapour/air mixtures may be formed.

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)

· May cause toxic effects if inhaled or absorbed through skin.

Causes liver and kidney injury in animal experiments; [HSDB] Defats skin and irritates nose and throat; [CAMEO] A skin and eye irritant; [Hawley] Causes CNS effects; [ICSC] See cis-Decahydronaphthalene.

Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract; [Sigma-Aldrich MSDS] See Decahydronaphthalene.

A skin and strong eye irritant; Harmful by inhalation; [Sigma-Aldrich MSDS] See Decahydronaphthalene. See Cyclohexane.

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.

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)

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].

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

Use powder, carbon dioxide, foam. In case of fire: keep drums, etc., cool by spraying with water.

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.

Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

INHALATION: remove to fresh air.

General First Aid:

· Wear positive pressure self-contained breathing apparatus (SCBA).

5.0 [ppm]

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.

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.

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.

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.

LC50 Leuciscus idus melanotus 4.3 mg/L/48 hr /Conditions of bioassay not specified/

LC50 Oryzias latipes 1.84 mg/L/48 hr /Conditions of bioassay not specified/

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).

Neurotoxin - Acute solvent syndrome

Dermatotoxin - Skin burns.

Neurotoxin - Acute solvent syndrome

/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. ...

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

Redness. Pain. Skin burns.

Redness. Pain. Severe deep burns.

Nausea. Vomiting. Abdominal pain. Further see Inhalation.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=91-17-8]

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).

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.

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. ...

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.

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. ...

Used as a solvent for naphthalene, fats, resins, oils, waxes, rubber, lacquers, shoe polishes, floor waxes, and lubricants; Used as a motor fuel additive, metal cleaner, spot remover, and stove fuel; [HSDB]

Metal Degreasing [Category: Clean]

Used as a solvent for naphthalene, fats, resins, oils, waxes, lacquers, shoe polishes, and floor waxes; Also used as a lubricant additive and fuel; [Merck Index]

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.

In research as pharmacological, noncarcinogenic vehicle in long-term skin painting and somatic mutation studies.

Solvent for oils, fats, waxes, resins, rubber. Substitute for turpentine: cleaning machinery; stain remover, shoe creams; floor waxes; cleaning fluids; lubricants; motor-fuel additives.

HYDROGENATION OF NAPHTHALENE IN GLACIAL ACETIC ACID IN PRESENCE OF PLATINUM CATALYST @ 25 °C & 130 ATM YIELDS MIXT OF 77% CIS-DECALIN & 23% TRANS-DECALIN. HYDROGENATION OF TETRALIN UNDER SAME CONDITIONS YIELDS ALMOST ONLY CIS-DECALIN. ... HYDROGENATION OF DELTA-4A(8A)-OCTALIN IN ETHANOL IN PRESENCE OF PLATINUM YIELDS TRANS-DECALIN AS MAIN COMPONENT.

BY TREATMENT OF NAPHTHALENE IN FUSED STATE (ABOVE 100 °C) WITH HYDROGEN IN PRESENCE OF COPPER OR NICKEL CATALYST.

Decalin is produced by liquid-phase hydrogenation of naphthalene under pressure in the presence of nickel catalysts. The proportion of the two stereoisomers formed depends on the reaction conditions.

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/

Plastics Product Manufacturing

Naphthalene, decahydro-: ACTIVE

Naphthalene, decahydro-, cis-: ACTIVE

Naphthalene, decahydro-, trans-: ACTIVE