1,4-Dioxane

HCID 178781408

Grundinformationen

CAS
8031-47-8
Standard-SMILES
C1COCCO1
InChIKey
RYHBNJHYFVUHQT-UHFFFAOYSA-N
Summenformel
C4H8O2
Durchschnittliche Molmasse
88,11 g/mol

Überblick

1,4-Dioxane is a clear liquid that easily dissolves in water. It is used primarily as a solvent in the manufacture of chemicals and as a laboratory reagent; 1,4-dioxane also has various other uses that take advantage of its solvent properties. 1,4-Dioxane is a trace contaminant of some chemicals used in cosmetics, detergents, and shampoos. However, manufacturers now reduce 1,4-dioxane from these chemicals to low levels before these chemicals are made into products used in the home.

Namen und Bezeichner

Bevorzugter Name
1,4-Dioxane
IUPAC
1,4-dioxane
Englischer Name
p-Dioxane, Reagent
Summenformel
C4H8O2
Molmasse
88.11

Namen und Synonyme

1,4-DIOXANEDioxane123-91-1p-DioxaneDiethylene ether1,4-Diethylene dioxide1,4-DioxacyclohexaneDioxanTetrahydro-1,4-dioxinTetrahydro-p-dioxinDi(ethylene oxide)Diethylene dioxide
Weitere Namen anzeigen
p-Dioxane, Reagent
DioxanneDioxane-1,41,4-DioxanGlycol ethylene etherDioxan-1,4p-DioxanTetrahydro-para-dioxinDioxyethylene ether

Datenbank-Bezeichner

CAS
8031-47-8
ChEMBL
CHEMBL453716
ChEBI
CHEBI:47032
UNII
J8A3S10O7S
EC Number
204-661-8
Nikkaji
J2.502J

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,3
Polarare Oberfläche (TPSA)
18,5 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
0
Schwere Atome
6

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 3 Einträge

Hazardous Air Pollutants (HAPs)

Carcinogens

Volatile Organic Compound (VOC)

DrugsPharmaceuticals -> Listed in ZINC15
SolventsSolvents -> Ethers (<C12)
SpringerMaterials PropertiesSchoenflies notation
PesticidesPesticide -> EPA IRIS
LogP · 3 Einträge

log Kow = -0.27

-0.27

-0.27

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P318, P319, P337+P317, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P318, P319, P337+P317, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: 1,4-Dioxane

Hazard Traits - Carcinogenicity; Hematotoxicity; Hepatotoxicity and Digestive System Toxicity; Nephrotoxicity and Other Toxicity to the Urinary System; Neurotoxicity; Ocular Toxicity; Respiratory Toxicity

1,4-Dioxane is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Dioxane 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: 04-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15842

Substance: 1,4-dioxane

1,4-Dioxane: HSNO Approval: HSR001140 Approved with controls

Other Safety InformationEvaluation - 1,4-Dioxane
DOT LabelFlammable Liquid
Fire Hazards · 3 Einträge

Special Hazards of Combustion Products: Toxic vapors are generated when heated.

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

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive. Risk of fire and explosion on contact with incompatible substances. See Chemical Dangers.

Fire PotentialA very dangerous fire and explosion hazard when exposed to heat or flame.
Health Hazards · 2 Einträge

No significant irritation from brief exposure of skin; prolonged or repeated exposure may cause a rash or burn and absorption of toxic amounts leading to serious injury of liver and kidney. Chemical has poor warning properties; illness may be delayed. Moderately irritating to eyes; overexposure may cause corneal injury. (USCG, 1999)

· Inhalation or contact with material may irritate or burn skin and eyes.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

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

First Aid Measures · 4 Einträge

Fresh air, rest. Refer immediately for medical attention.

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

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth. Do NOT induce vomiting. Seek medical attention if you feel unwell.

Accidental Release Measures · 2 Einträge

· 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.

First Aid · 3 Einträge

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from strong oxidants, strong acids and incompatible materials. Cool. Dry. Well closed. Keep in the dark. Store only if stabilized. Store in an area without drain or sewer access.
Firefighting Hazards... Vapor is heavier than air ... and may travel considerable distance to source of ignition and flash back. ...

Toxikologische Informationen

Toxicological InformationCDC-ATSDR Toxicological Profile
Body Burden · 1 Eintrag

1,4-Dioxane was detected at mean levels of 0.2 ug/cu m (N = 110) and 0.05 ug/cu m (N = 24) in the exhaled breath of human subjects at two different locations in Los Angeles, CA. 1,4-Dioxane was also detected at a mean level of 0.2 ug/cu m (N = 67) in the exhaled breath of persons in Contra Costa, CA(1).

Cancer Sites · 2 Einträge

Gastrointestinal

[in animals: lung, liver & nasal cavity tumors]

Interactions · 2 Einträge

... /In Swiss Webster mice/ skin paintings /with 0.2 mL of unspecified concn of 1,4-dioxane/ were preceded 1 wk earlier by application of 50 ug 7,12-dimethylbenzanthracene (DMBA); 4 males and 5 females survived 59 wk of treatment. Among 15 mice examined, 8 skin tumors were observed (2 papillomas, 2 squamous-cell carcinomas and 4 sarcomas); in addition 24 other tumors (mainly malignant lymphomas and lung tumors) occurred. 8 skin papillomas and 1 malignant lymphoma occurred in 55 animals receiving 50 ug DMBA followed by thrice weekly paintings with acetone alone.

Dioxane ... was investigated as a rat liver altered foci promoter in an initiation/promotion protocol. Animals were initiated with diethylnitrosamine, 30 mg/kg, injected ip 24 hr after 2/3 partial hepatectomy. The chemical under study was administered by gavage once a day, 5 times a week for 7 weeks. Ten days after the last administration the animals were killed. Liver sections were stained for gamma-glutamyl-transpeptidase (GGT) and the number and total volume of gamma-glutamyl-transpeptidase-positive foci was studied. Dioxane (1000 mg/kg) significantly increased the number and total volume of foci ... .

Target Organs · 3 Einträge

Cancer, Developmental (effects while organs are developing), Hepatic (Liver), Ocular (Eyes), Renal (Urinary System or Kidneys), Respiratory (From the Nose to the Lungs)

Hepatic

Eyes, skin, respiratory system, liver, kidneys

Health Effects · 1 Eintrag

1,4-Dioxane for short period of time cause eye and nose irritation at low levels, and severe kidney and liver effects and possibly death at very high levels. For long-term exposure, studies in animals have shown that breathing vapors of 1,4-dioxane, swallowing liquid 1,4-dioxane or contaminated drinking water, or having skin contact with liquid 1,4-dioxane affects mainly the liver and kidneys. Studies in workers did not indicate whether 1,4-dioxane causes cancer, but animal studies suggest that it is a probable human carcinogen. (L1189)

Regulatorische Informationen

FDA RequirementsDioxane is an indirect food additive for use only as a component of adhesives. /Dioxane/
RCRA Requirements · 1 Eintrag

U108; As stipulated in 40 CFR 261.33, when 1,4-diethylene oxide, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Atmospheric Standards · 2 Einträge

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. 1,4-Dioxane is produced, as an intermediate or a final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 1,4-Dioxane is included on this list.

CERCLA Reportable Quantities · 1 Eintrag

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

State Drinking Water Guidelines · 5 Einträge

(CA) CALIFORNIA 3 ug/L

(FL) FLORIDA 5 ug/L

(MA) MASSACHUSETTS 0.3 ug/L

(ME) MAINE 32 ug/L

(NH) NEW HAMPSHIRE 3 ug/L

Chemie und Industrie

Pharmakologische Informationen

Biological Half-Life · 4 Einträge

/Humans/ exposed to 50 ppm for 6 hr /exhibited/ a half-life of 0.98 + or - 0.12 hr in plasma.

Four male Sprague-Dawley rats with jugular vein cannulas were placed in a 1 liter "head-only" chamber under dynamic air flow conditions. The flow rate of 1,4-dioxane vapor was adjusted to give a chamber concentration of 180 mg/cu m (50 ppm). During and after the 6-hr exposure urine was collected and analysed. ... A half life of 1.01 hours was calculated. ...

Six rats received iv doses of 3, 10, 30, 100, 300 or 1,000 mg (14)C-1,4-dioxane/kg bw and samples of blood were obtained via the right jugular vein every 5 minutes for estimating radioactivity in plasma. Two additional rats were used to estimate radioactivity in expired air (1,4-dioxane and (14)CO2) as well as in urine and feces. These rats were equipped with jugular and ureter cannulas. At the lowest iv doses given, 3 and 10 mg/kg bw, radioactivity was eliminated from the plasma by apparently linear kinetics with a t1/2 of 1.1 hours. At higher doses, radioactivity was eliminated from plasma progressively more slowly. At dose levels >/=100 mg/kg bw, elimination was retarded till a peak level of about 100 ug/mL plasma was reached, whereafter elimination occurred with the same t1/2 as that at lower doses. ...

Four volunteers /were exposed/ to 50 ppm [180 mg/m3] 1,4-dioxane vapor for 6 h. It was rapidly taken up, with plasma levels reaching a plateau after 3 h. The major metabolite, b-hydroxyethoxyacetic acid (HEAA), was detected during the exposure period. At the end of the exposure, plasma levels of 1,4-dioxane fell with a half life of 59 min. ...

Metabolism/Metabolites · 6 Einträge

1,4-Dioxane and beta-hydroxyethoxyacetic acid (HEAA) were found in urine of plant personnel exposed to time-weighted average concentration of 1.6 ppm dioxane for 7.5 hr. Average concentration of dioxane and HEAA in urine were 3.5 and 414 umoles/L, respectively.

From urine of rats given dioxane gas chromatography revealed a hepatic carcinogen identified as p-dioxane-2-one, a major metabolite.

Fate of dioxane in rats is markedly dose dependent because of limited capacity of rats to metabolize to beta-hydroxyethoxyacetic acid, (HEAA). At saturation, max velocity of metabolism to HEAA was about 18 mg/kg. At high daily doses dioxane induced its own metabolism. There is an apparent threshold for toxic effects of dioxane that coincides with saturation of metabolic pathway for its detoxification.

Another proposed metabolite of dioxane is 1,4-dioxane-2-one. However, whether 1,4-dioxane is first metabolized to HEAA, which can cyclize to 1,4-dioxane-2-one, or the parent is metabolized directly to 1,4-dioxane-2-one remains unanswered.

For more Metabolism/Metabolites (Complete) data for 1,4-DIOXANE (8 total), please visit the HSDB record page.

Exposure to 1,4-dioxane may occur by inhalation, ingestion, and to a lesser extent by dermal contact. 1,4-Dioxane is quickly absorbed and metabolized to beta-hydroxyethoxyacetic acid (HEAA) by mixed-function oxidase enzymes. HEAA can then be converted to 1,4-dioxane-2-one under acidic conditions. Both of these products are rapidly and extensively eliminated in the urine (>95%). Unchanged 1,4-dioxane can also be excreted in the urine and in exhaled air, but mainly after high-dose exposure. (L1189)

Absorption, Distribution and Excretion · 5 Einträge

... Readily absorbed through the intact skin ...

Dioxane can be absorbed after inhalational or dermal exposure. Dermal absorption occurs but to a much lesser extent than absorption via other routes.

In male rats given single oral doses of 10, 100 or 1000 mg/kg (14)C 1,4-dioxane, excretion of unchanged 1,4-dioxane in expired air was 0.043 mg/kg (0.43%) at lowest dose and 252 mg/kg (25%) at highest dose.

Plasma concentration time curves for dioxane given iv to rats at levels of 3-1000 mg/kg and for inhalation of 50 ppm vapor for 6 hr were linear by each route with half-life of about 1 hr. Above 10 mg/kg, plasma clearance rate decrease, /beta-hydroxyethoxyacetic acid/ (HEAA) excretion decreased and excretion as dioxane increased.

For more Absorption, Distribution and Excretion (Complete) data for 1,4-DIOXANE (17 total), please visit the HSDB record page.

Verwendung und Herstellung

Uses · 6 Einträge

1,4-Dioxane is used as a solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, some dyes, and other organic and inorganic compounds.

Used as a solvent for cellulose esters, ethers, and other organic chemicals; [ACGIH] Used as a solvent in resins, polymers, oils, waxes, dyes, wood pulping, adhesives, varnishes lacquers, paints, and cosmetics; [HSDB]

Metal Degreasing [Category: Clean]

Stabilizer in chlorinated solvents. Organic solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, oil and spirit-soluble dyes, and many other organic as well as some inorganic compounds.

The largest single use of 1,4-dioxane is the stabilization of 1,1,1-trichloroethane against chemical attack by aluminum.

Historically, 1,4-dioxane has been used as a stabilizer for the solvent 1,1,1-trichloroethane. However, this use is no longer expected to be important due to the 1990 Amendments to the Clean Air Act and the Montreal Protocol, which mandate the eventual phase-out of 1,1,1-trichloroethane production in the U.S.

Impurities · 4 Einträge

1,4-Dioxane may contain bis(2-chloroethyl) ether ... as an impurity.

The tendency of 1,4-dioxane to form peroxides may be lessened by the addition of a reducing agent, such as stannous chloride or ferrous sulfate.

Peroxides: 0.003% max (certified reagent), 50 mg/kg max (technical); acetic acid: 0.01% max (certified reagent), 0.1% max (technical); Water : 0.02% max (certified), 0. 1% max (technical); Non-volatile matter : 0.004% max (certified), 0.0025% max (technical) ; 2-methyl-1,3-dioxolane: not reported (certified), 0.05%. /From table/

Certified reagent grade: carbonyl : 0.05% max; heavy metals (Pb) : 0.25 ppm max; iron: 0.25 ppm max. /From table/

U.S. Exports · 3 Einträge

(1978) No Data

(1982) No Data

(1987) No Data

U.S. Imports · 3 Einträge

(1977) AT LEAST 9.08X10+7 G

(1982) No Data

(1987) No Data

U.S. Production · 6 Einträge

2023: 75,000 - <100,000 lb

(1982) 6.80X10+9 G

(1973) 7.357X10+9 G

(1974) 8.003X10+9 G

(1975) 5.712X10+9 G

For more U.S. Production (Complete) data for 1,4-DIOXANE (15 total), please visit the HSDB record page.

Consumption Patterns... /Approximately/ 90% of the 1,4-dioxane produced annually is used as a stabilizer for chlorinated solvents, particularly, 1,1,1-trichloroethane. ... The remainder of the 1,4-dioxane production is used in solvent applications (1985).

Zugehörige Reaktionen

0

Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.

Notizen zur Verbindung

Wird geladen…