Tetralin

Other Classes -> Naphthalenes

Volatile Organic Compound (VOC)

3.78

3.49

ODOR RESEMBLING MIXTURE OF BENZENE & MENTHOL

MOLDY, TURPENTINE ODOR

Pungent odor

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

0.9702 G/ML @ 20 °C/4 °C

MOISTURE CONTENT NONE; RESIDUE ON EVAPORATION NONE; BULK DENSITY 8 LB/GAL

Relative density (water = 1): 0.9702

0.981 @25 °C

MISCIBLE WITH ETHANOL, BUTANOL, ACETONE, BENZENE, PETROLEUM ETHER, CHLOROFORM, &PETROLEUM ETHER, DECALIN; SOL IN METHANOL: 50.6% WT/WT; INSOL IN WATER.

SOL IN ANILINE

SOL IN ETHER

Solubility in water: very poor

176 °F (USCG, 1999)

82 °C

171 °F (77 °C) (OPEN CUP); 180 °F (82 °C) (CLOSED CUP)

160 °F (71 °C) (CLOSED CUP)

176 °C (Closed cup); 190 °F (Open cup)

77 °C o.c.

406 °F at 760 mmHg (USCG, 1999)

207.6 °C @ 760 MM HG

207.6 °C

207.2 °C @760 [mm Hg]

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 1.5% (11 of 729) of reports.

Danger

H304 (20.3%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]

Chemical: Naphthalene, 1,2,3,4-tetrahydro-

Naphthalene, 1,2,3,4-tetrahydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Naphthalene, 1,2,3,4-tetrahydro- 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: 11-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21076

1,2,3,4-Tetrahydronaphthalene: Does not have an individual approval but may be used under an appropriate group standard

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 77 °C explosive vapour/air mixtures may be formed.

Listed in table of Methemoglobinemia-inducing agents: industrial, environmental, and pharmaceutical; [Sullivan, p. 729]; Tetralin is a skin and mucous membrane irritant. When used in poorly ventilated areas, tetralin may cause central nervous system depression. Ingestion of tetralin has caused green urine and laboratory evidence of liver and kidney injury. [HSDB] A skin, eye, and respiratory tract irritant; Inhalation of high concentrations may cause CNS effects; May cause kidney injury; [ICSC]

BEAUMONT D, WAIGH RD; THE BETA-ADRENOMIMETIC ACTIVITY OF TETRAHYDROISOQUINOLINESAND TETRAHYDRONAPHTHALENES. PROG MED CHEM 18: 45-86 (1981). A REVIEW WITH 155 REFERENCES ON THE BETA-ADRENOMIMETIC ACTIVITY OF 1,2,3,4-TETRAHYDROISOQUINOLINE AND 1,2,3,4-TETRAHYDRONAPHTHALENE DERIVATIVES.

Nelson NA et al; Solvent Nephrotoxicity in Humans and Experimental Animals. Am J Nephrol 10 (1): 10-20 (1990). Evidence from human case reports, epidemiologic studies and animal experiments have suggested that exposure to organic solvents is associated with a wide spectrum of renal disorders, including tubular necrosis, interstitial disease, glomerulonephritis and neoplasia. This review summarizes what is known about solvent induced renal damage in humans and experimental animals, with emphasis on hypothesized mechanisms by which this broad range of disorders may occur.

TETRAHYDRONAPHTHALENE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick 1979 p.151-154].

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

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

Fresh air, rest. Refer for medical attention.

Rinse skin with plenty of water or shower. Remove contaminated clothes.

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

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

IN GENERAL MATERIALS ... TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS ... SHOULD BE STORED IN COOL ... VENTILATED PLACE, OUT OF ... SUN, AWAY FROM ... FIRE HAZARD ... BE PERIODICALLY INSPECTED & MONITORED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED.

Personal protection: chemical protection suit. Do NOT let this chemical enter the environment. Ventilation. Collect leaking and spilled liquid in covered containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

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.

TERRESTRIAL FATE: If released to soil, adsorption is expected to take place. However, it has been detected in groundwater beneath a municipal landfill(4) and the annual loadings of tetralin in runoff from land in the Canadian Ontario and Great Lakes water basins are estimated to be 1,053 and 2,270 kg/yr, respectively(5). Based on biodegradation half-lives of 4-13 days in aquatic systems(1-3), biodegradation in soil will be important(SRC).

AQUATIC FATE: Based on the estimated Henry's Law constant of 1.7X10-3 atm-cu m/mol at 25 °C(2), volatilization half-lives from a model river (1 m deep flowing 1 m/sec and wind velocity of 3 m/sec) and lake (1 m deep) can be estimated to be 4 hours and 5 days, respectively(1,SRC). An estimated Koc value of 1,800(3) suggests a high adsorption potential; furthermore, tetralin was detected in suspended solids from St. Louis Bay(4). Screening and grab sample tests indicate a biodegradation half-life of 4-13 days in seawater, groundwater, and river water(5-7). Bioconcentration in fish may be important in organisms that cannot metabolize tetralin(8).

ATMOSPHERIC FATE: Based on the experimental vapor pressure of 0.368 mm Hg at 25 °C(1), tetralin is expected to exist almost entirely in the vapor phase in the ambient atmosphere(2). Vapor phase tetralin will degrade rapidly in the ambient atmosphere by reaction with photochemically produced hydroxyl radicals with a half-life of about 11 hours(3,SRC). Vapor phase tetralin will also degrade in the ambient atmosphere at night-time by reaction with nitrate radicals with a half-life of about 3.6 days(4-5,SRC).

Cough. Dizziness. Headache. Nausea. Vomiting. Weakness.

Redness. Pain.

Pain. Redness. Blurred vision.

Abdominal pain. 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=119-64-2]

Tetralin was identified at a concn range of 13.3-154.3 ng/L in paper-mill effluents being discharged into the Rainy River(1). Tetralin was qualitatively identified in advanced waste treatment water from Lake Tahoe, CA in October of 1974(2). Tetralin was detected at a concn range of 2-58 ug/mL in 5 incinerator effluent extracts(3). Tetralin was detected 1 km from a Volvo assembly plant in Goteborg, Sweden at a concn of 4.6 ug/cu-m on January 14, 1981; regional Goteburg air contains less than 0.01 ug/cu-m tetralin(4). Also, 30 ug/cu-m tetralin was detected in air nearby a Saab assembly plant in Sweden on January 19, 1981(4). These data suggest tetralin is released from automobile assembly plants in emissions from solvents used during painting processes(4). Tetralin emission rates from well-tuned radiant and maltuned convective kerosene space heaters ranged from 100-240 ng/kJ(5).

Based upon monitoring data of runoff from land, approximately 1,053 and 2,271 kg tetralin/yr are input to the Canadian Lake Ontario and Canadian Great Lakes water basins, respectively(1). Tetralin was detected at a concn of 11 ng/g in wastewater from the petroleum refining industry after dissolved air flotation(2).

... IN HIGH CONCENTRATIONS, /SRP: CNS DEPRESSANT/ ... .

... VAPORS ARE KNOWN TO PRODUCE HEADACHE, NAUSEA, VOMITING, AND IRRITATION OF CONJUNCTIVA AND OF RESPIRATORY TRACT MUCOSA. HIGH CONCENTRATIONS PRODUCE /CNS DEPRESSION/.

Dermal exposure to tetralin has caused eczematous dermatitis, but only rarely, and exposure to tetralin fumes in poorly ventilated places has produced /CNS depressant/ effects including marked restless, eye irritation, headache, malaise, asthenia, nausea, and vomiting.

A hallmark for tetralin exposure in man is the production of green colored urine. ... Green urine /was reported/ from a man who had ingested 5.7 g of a pigment called di-tetralin. ... Two cases of "tetralin urine" /were reported/ in painters who used tetralin-containing varnishes in a poorly ventilated area; these workers also showed intense irritation of the mucous membranes, profuse lacrimation , headache, and stupor.

For more Human Toxicity Excerpts (Complete) data for TETRALIN (12 total), please visit the HSDB record page.

Tetralin was detected in small mouth bass (Micropterus dolomieui) at a concn of 75.3 ng/g and yellow perch (Perca flavescens) at concns of 73.2 and 34.5 ng/g from the Rainy River which forms an international boundary between the U.S. and Canada(1).

Tetralin is released to the environment in emissions from automobile and diesel engines(1), incinerators(2), kerosene space heaters(3), and from automobile assembly plants during painting processes(4). Tetralin is released in effluents from paper-mills(5), petroleum refineries(6), and in advanced waste treatment effluents(7). Tetralin may also be released to surface waters via runoff from land(8).

DEGRADATION IN SEA WATER BY OIL OXIDIZING MICROORGANISMS: 31% BREAKDOWN AFTER 21 DAYS AT 22 °C IN STOPPERED BOTTLES CONTAINING A 1000 PPM MIXTURES OF ALKANES, CYCLOALKANES, AND AROMATICS.

One screening test using sewage seed suggests that tetralin (initial concn of 3-10 ppm) biodegrades slowly in synthetic seawater; 3, 3, 2, and 3 percent theoretical BOD in 5, 10, 15, and 20 days, respectively(1). However, 0.0124 ppm tetralin was not detected after 10 days of incubation in artificial seawater at 25 °C indicating that tetralin is moderately oxidized(2). An initial concn of 0.0112 ppm tetralin was observed to degrade 100% in 8 days in a groundwater grab sample at 10 °C and pH 8(3). Tetralin (20.1 ppm initial concn) exhibited 18, 40, 58, 65, 70, and 75 percent theoretical CO2 production after 5, 10, 15, 20, 25, and 35 days, respectively, in water from the Ohio River at 22-25 °C and pH 7.2; the half-life in this study was 13 days and, after redosing, a half-life of 9 days was observed under the same conditions(4).

(1-(14)C)-TETRALIN IS METABOLIZED IN RABBITS BY HYDROXYLATION OF ALICYCLIC RING TO YIELD CONJUGATES OF AC-ALPHA-TETRALOL (60% OF DOSE), AC-BETA-TETRALOL (20%) & TETRALIN-1,2-DIOL (2.5%), & HYDROXYLATION OF AROMATIC RING ... YIELDING AR-BETA-TETRALOL (5,6,7,8-TETRAHYDRO-2-NAPHTHOL, 0.1%).

YIELDS 2-HYDROXYTETRALYLMERCAPTURIC ACID, 1,2,3,4-TETRAHYDRO-1-NAPHTHOL, 1,2,3,4-TETRAHYDRO-2-NAPHTHOL IN RABBIT. YIELDS 1,2,3,4-TETRAHYDRO-1,2-DIHYDROXYNAPHTHALENE, 5,6,7,8-TETRAHYDRO-2-NAPHTHOL IN RABBIT. /FROM TABLE/

In rabbits, the main urinary metabolite was the glucuronide of alpha-tetralol (52.4%). Other conjugated metabolites were beta-tetralol (25.3%), 4-hydroxy-alpha-tetralone (6.1%), and cis-tetralin-1,2-diol (0.4%). Using rat liver homogenates, it was shown that conversion of tetralin to tetralol requires reduced nicotinamide adenine dinucleotide phosphate and that tetralin hydroperoxide is a probable intermediate. Further study confirmed this possibility and indicated that tetralin hydroxylation proceeds via a radical mechanism similar to that of lipid peroxidation.

Tetralin, a component of fuels, solvents, and varnishes, is metabolized in male Fischer 344 rats to 1-tetralol, 2-tetralol, 2-hydroxyl-1-tetralone, 4-hydroxyl-1-tetralone, 1,2-tetralindiol, and 1,4-tetralindiol.

ABSORBED VAPOR IS EXCRETED BY KIDNEYS AS ALPHA- AND BETA-TETRAHYDRONAPHTHOLS ANDTHEIR GLUCURONIDES ... .

RADIOACTIVE TETRALIN, WHEN ADMIN TO RABBIT, WAS EXCRETED IN URINE AS GLUCURONIDEAT 87-99% AND IN FECES AT 0.6-1.8% OF ORIGINAL DOSE. ... WAS ABSORBED BY MUSSEL BUT NOT METABOLIZED; ... UP TO 80% WAS RELEASED IN UNCHANGED FORM WHEN THE ORGANISM WAS TRANSFERRED TO FRESH SEAWATER.

When radioactive tetralin was fed to rabbits, 87-90% of the activity was excreted in the urine in 2 days and 0.5-3.7% on the third day. The feces contained only 0.6-1.8%. No radioactivity was found in the breath, and negligible amounts were retained in the tissues. About 90-99% of the dose was accounted for.

Used in the solvent, paint, varnish, and rubber industries; tetralin is used in shoe polish and floor wax; [HSDB]

Painting (Solvents) [Category: Paint]

SOLVENT FOR CAMPHOR, SULFUR & IODINE; IN PAINT THINNERS; AS PAINT REMOVER WHEN MIXED WITH DECALIN OR WHITE SPIRIT; AS INSECTICIDE FOR CLOTHES MOTH; AS SUBSTITUTE FOR TURPENTINE & PETROL IN GERMANY.

SOLVENT FOR NAPHTHALENE, FATS, RESINS, OILS, WAXES, USED INSTEAD OF TURPENTINE IN LACQUERS, SHOE POLISHES, FLOOR WAXES; DEGREASING AGENT.

IN PLANT PATHOLOGY, TETRALIN HAS BEEN SUCCESSFUL IN TOTAL DESTRUCTION OF CROWN GALL AND OLIVE KNOT NEOPLASMS.

A COMBINATION OF 31% TETRAHYDRONAPHTHALENE AND 0.03% CUPRIC OLEATE (CUPREX) IS PROMOTED AS A PEDICULICIDE AND MITICIDE, BUT ITS TRUE EFFICACY REMAINS TO BE DETERMINED.

2023: <50,000 lb

(1975) GREATER THAN 9.08X10+5 G

(1972) PROBABLY GREATER THAN 4.54X10+5 G

BY CATALYTIC HYDROGENATION OF PURIFIED NAPHTHALENE.

... FORMED DURING ACIDIC, CATALYTIC HYDROCRACKING OF PHENANTHRENE.

ISOLATED FROM MIDDLE FRACTION OF COAL OIL.

Hydrogenation of naphthalene in the presence of a catalyst at 150 °C.

"ESSENCE OF TETRALIN" IS COMMERCIAL MIXTURE OF TETRALIN & HEXALIN, PALE YELLOW LIQUID WHICH IS BETTER SOLVENT OF RESINS THAN TETRALIN ALONE ... .

GRADES OR PURITY: 90+%

THE COMMERCIAL PRODUCT TYPICALLY HAS A TETRAHYDRONAPTHALENE CONTENT OF >97 wt%.

Grade: Technical

Naphthalene, 1,2,3,4-tetrahydro-: ACTIVE

PEROXIDE FORMATION /FROM CONTACT WITH AIR/ IS PREVENTED BY THE ADDITION OF AN ANTIOXIDANT, SUCH AS HYDROQUINONE.

Compatible with natural and synthetic vehicles.

The germicidal action of quaternary ammonium cmpd was increased by a factor of 3 with the addition of tetralin.

Tetralin ring used in a group of new fungicidal phenols, which have lower phyto and mammalian toxicity as compared to known phenolic fungicides.

Used as a chemical intermediary in the formation of acylisopropyltetramethylindans which have a musk aroma and enhance the aroma of perfume cmpd and colognes.