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123-91-1

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Identification

Name
1,4-Dioxane
CAS
123-91-1
Synonyms
1,4-DIETHYLENE DIOXIDE
1,4-DIOXAN
1,4-DIOXANE
DIETHYLENE DIOXIDE
DIETHYLENE ETHER
DIETHYLENE OXIDE
DIOX
P-DIOXANE
1,4-Dioxacyclohexane
1,4-Dioxin, tetrahydro-
1,4-dioxin,tetrahydro
Diethyeneoxide
Diethylendioxid
Diethylene oxide ethe
Diokan
Dioksan
Diossano-1,4
Dioxaan-1,4
Dioxan
Dioxan-1,4
EINECS(EC#)
204-661-8
Molecular Formula
C4H8O2
MDL Number
MFCD00006571
Molecular Weight
88.11
MOL File
123-91-1.mol

Chemical Properties

Description
1,4-dioxane is a clear liquid with ether-like odour. It is highly flammable and forms explosive peroxides in storage (rate of formation increased by heating, evaporation, or exposure to light). 1,4-Dioxane is incompatible with oxidising agents, oxygen, halogens, reducing agents, and moisture. Industrial applications of 1,4-dioxane are extensive, for instance, as solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, and some dyes; as a solvent for paper, cotton, and textile processing; and for various organic and inorganic compounds and products. It is also used in automotive coolant liquid and in shampoos and other cosmetics as a degreasing agent and as a component of paint and varnish. Human exposures to 1,4-dioxane have been traced to multiple occupations and breathing of contaminated workplace air and drinking polluted water. Industrial uses of 1,4-dioxane are very many. For instance, it is used as solvent for celluloses, resins, lacquers, synthetic rubbers, adhesives, sealants, fats, oils, dyes, and protective coatings; as a stabiliser for chlorinated solvents and printing inks; and as a wetting and dispersing agent in textile processing agrochemicals and pharmaceuticals, in different processing of solvent-extraction processes, and in the preparation and manufacture of detergents.
Appearance
colourless liquid
mp 
12 °C
bp 
101 °C
density 
1.034 g/mL at 25 °C(lit.)
vapor density 
3 (vs air)

vapor pressure 
27 mm Hg ( 20 °C)

refractive index 
n20/D 1.422(lit.)

Fp 
54 °F

storage temp. 
Flammables area
Stability:
Stable. Incompatible with oxidizing agents, oxygen, halogens, reducing agents, moisture. Highly flammable-note wide explosive range. May form explosive peroxides in storage (rate of formation increased by heating, evaporation or exposure to light).
Water Solubility 
SOLUBLE
Sensitive 
Hygroscopic
Merck 
14,3300
BRN 
102551
CAS DataBase Reference
123-91-1(CAS DataBase Reference)
NIST Chemistry Reference
1,4-Dioxane(123-91-1)
Storage Precautions
Store under nitrogen;Moisture sensitive
EPA Substance Registry System
123-91-1(EPA Substance)

Hazard Information

Chemical Properties
1,4-dioxane is a clear liquid with an ether-like odor. It is highly flammable and forms explosive peroxides in storage (rate of formation is increased by heating, evaporation, or exposure to light). 1,4-Dioxane is incompatible with oxidizing agents, oxygen, halogens, reducing agents, and moisture. 1,4-Dioxane is used as a solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, some dyes, as a solvent for paper, cotton, and textile processing, and for various organic and inorganic compounds and products. It is also used in automotive coolant liquid, in shampoos and other cosmetics as a degreasing agent, and as a component of paint and varnish. Human exposures to 1,4-dioxane have been traced to multiple occupations, breathing of contaminated workplace air, and drinking polluted water. There are many industrial uses of 1,4-dioxane, i.e., as a solvent for celluloses, resins, lacquers, synthetic rubbers, adhesives, sealants, fats, oils, dyes, and protective coatings; as a stabilizer for chlorinated solvents, printing inks; as a wetting and dispersing agent in textile processing, agrochemicals, and pharmaceuticals, and in the preparation and manufacture of detergents.
General Description
A clear colorless liquid with a faint ethereal odor. Flash point 55°F. Slightly denser than water and soluble in water. Vapors heavier than air. Susceptible to autooxidation to form peroxides.
Reactivity Profile
DIOXANE is a flammable liquid; when exposed to air DIOXANE undergoes autooxidation with formation of peroxides. In the distillation process peroxides will concentrate causing violent explosion. The addition complex with sulfur trioxide (1:1) sometimes decomposes violently on storing at room temperature [Sisler, H. H. et al., Inorg. Synth., 1947, 2, p. 174]. Evaporation of boron trifluoride in aqueous dioxane with nitric acid led to an explosion upon addition of perchloric acid [MCA Guide, 1972, p. 312]. Explosive reaction with Raney nickel catalyst above 210° C {Mozingo R., Org. Synth., 1955, Coll. Vol. 3, p. 182].
Air & Water Reactions
Highly flammable. When exposed to air DIOXANE(123-91-1) undergoes autooxidation with formation of peroxides. In the distillation process peroxides will concentrate causing violent explosion. Water soluble.
Health Hazard
Laboratory studies in experimental animals indicate that repeated exposures to large amounts of 1,4-dioxane in drinking water, in air, or on the skin cause convulsions, collapse, and damage to the liver and kidneys in animals. On inhalation of 1,4-dioxane, occupational workers suffered from severe poisoning. The symptoms of poisoning included coughing, irritation of eyes, drowsiness, vertigo, headache, anorexia, stomach pains, nausea, vomiting, irritation of the upper respiratory passages, coma, and death. 1,4-Dioxane also caused hepatic and renal lesions, and demyelination and edema of the brain among workers. (See the literature for more information.)
Health Hazard
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.

Safety Data

Hazard Codes 
Xn,F,T
Risk Statements 
R45:May cause cancer.
R11:Highly Flammable.
R36/38:Irritating to eyes and skin .
R48/23/24/25:Toxic: danger of serious damage to health by prolonged exposure through inhalation, in contact with skin and if swallowed .
R65:Harmful: May cause lung damage if swallowed.
R66:Repeated exposure may cause skin dryness or cracking.
R40:Limited evidence of a carcinogenic effect.
R36/37:Irritating to eyes and respiratory system .
R19:May form explosive peroxides.
R41:Risk of serious damage to eyes.
R37/38:Irritating to respiratory system and skin .
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R48/20/22:Harmful: danger of serious damage to health by prolonged exposure through inhalation and if swallowed .
R38:Irritating to the skin.
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Statements 
S9:Keep container in a well-ventilated place .
S16:Keep away from sources of ignition-No smoking .
S36/37:Wear suitable protective clothing and gloves .
S46:If swallowed, seek medical advice immediately and show this container or label .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S53:Avoid exposure-obtain special instruction before use .
S7:Keep container tightly closed .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S24/25:Avoid contact with skin and eyes .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
RIDADR 
UN 1993 3/PG 2

WGK Germany 
3

RTECS 
JG8225000


8
HazardClass 
3
PackingGroup 
II
HS Code 
29329900
Precautions
Workers Should be careful during handling of 1,4-Dioxane and avoid open flames, sparks and smoking. Workers should wear proper protectives since 1,4-Dioxane in known as hazardous, cause damage to eyes, respiratory tract, liver and kidney.
Safety Profile
Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenicdata. Poison by intraperitoneal route. Moderately toxic by ingestion and inhalation. Mildly toxic by skin contact. Human systemic effects by inhalation: lachrymation, conjunctiva irritation, convulsions, hgh blood pressure, unspecified respiratory and gastrointestinal system effects. Mutation data reported. An eye and slun irritant. The irritant effects probably provide sufficient warning, in acute exposures, to enable a worker to leave exposure before being seriously affected. Repeated exposure to low concentrations has resulted in human fatahties, the organs chefly affected being the liver and kidneys. A very dangerous fire and explosion hazard when exposed to heat or flame; can react vigorously with oxidizing materials. Violent reaction with (H2 + Raney Ni), AgClO4. Can form dangerous peroxides when exposed to air. Potentially explosive reaction with nitric acid + perchloric acid, Raney nickel catalyst (above 210°C). Forms explosive mixtures with decaborane (impactsensitive), triethynylaluminum (sensitive to heating or drying). Violent reaction with sulfur trioxide. Incompatible with sulfur trioxide. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS.
Hazardous Substances Data
123-91-1(Hazardous Substances Data)

Raw materials And Preparation Products

Material Safety Data Sheet(MSDS)

msds information
1,4-dioxane(123-91-1).msds

Questions And Answer

description
1,4-Dioxane is a hexahydroxy heterocyclic compound containing two oxygen heteroatoms. molecular formula C4H8O2,a colorless, flammable liquid, slight ether smell, photosensitive. Its Vapor can easily form explosive peroxides by absorbing oxygen in the air. Explosion limit 1.97%-1.97% (volume), It should be disposed by reducing agent in distillation process. Melting point 11.8 ℃, boiling point of 101 ℃ (750 mmHg), density 1.0337 (20/4 ℃), refractive index 1.4224, flash point12℃. Soluble in water, ethanol, ether and other organic solvents. It can form azeotrope with water (water content 18.6%) and the boiling point is 87.8 ℃. It turns bright yellow when reacting with tetranitromethane. Trace amount of 2,6-Di-tert-butyl-4-methylphenol(BHT) is often added to the commodity as a stabilizer. Low toxicity, half lethal dose (rats, oral) 4200 mg/kg. A possible carcinogen, an irritating chemical. 1,4-Dioxane can be prepared by dehydration of ethylene glycol by sulfuric acid and it is the indirect product in the production of epoxy ethane. As a good organic solvent, it has a wide application such as the solvent for cellulose acetate and lots of resins. It Is mainly used in the pharmaceutical industry as extraction agent, as a stabilizer in the production of 1,1,1 – trichloroethane as a volatile solvent in the production of polyurethane in place of dimethylformamide and tetrahydrofuran, as stripping agent in the crafts of coating and painting, as a solvent and dispersant in the dye industry, as a stabilizer in printing ink, and also as treatment agent for metal surface. In addition , it can also be used in cosmetics, spices manufacture, electroplating, etc.
uses
Industrial applications of 1,4-dioxane are extensive, for instance, as solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, and some dyes; as a solvent for paper, cotton, and textile processing; and for various organic and inorganic compounds and products. It is also used in automotive coolant liquid and in shampoos and other cosmetics as a degreasing agent and as a component of paint and varnish. Human exposures to 1,4-dioxane have been traced to multiple occupations and breathing of contaminated workplace air and drinking polluted water. Industrial uses of 1,4-dioxane are very many. For instance, it is used as solvent for celluloses, resins, lacquers, synthetic rubbers, adhesives, sealants, fats, oils, dyes, and protective coatings; as a stabiliser for chlorinated solvents and printing inks; and as a wetting and dispersing agent in textile processing agrochemicals and pharmaceuticals, in different processing of solvent-extraction processes, and in the preparation and manufacture of detergents.
Production
1,4-Dioxane can be prepared by dehydration of ethylene glycol orpolyglycol ether by the catalysis of sulfuric acid and can also be prepared by direct dimerization of Ethylene oxide. The dimerization process was carried out in the presence of acid catalysts such as sulfuric acid, Sodium bisulfate, boron trifluoride, etc. Powdered sodium hydroxide can be added to 1,4-Dioxane of industrial grade to remove the acid and water, by filtering the solid and distillation to get prurified product.
Mechanism of action
An inhalation study in four male volunteers exposed to 50 ppm of dioxane determined that the majority (99.3%) of dioxane is eliminated by metabolism to β-hydroxyethoxyacetic acid (HEAA) with the remaining 0.7% being excreted through the urine (Young et al., 1977). Further studies suggest that the metabolism of dioxane is mediated by cytochrome P450 (Woo et al., 1978). The concentrations of HEAA were found to be 118% higher than the concentration of dioxane, suggesting rapid and extensive metabolism with a calculated metabolic clearance rate of 75 m/min. This same study concluded that repeated daily exposures to 50 ppm of dioxane would not cause adverse effects because accumulated concentrations would never exceed those attained at 50 ppm or less. β-Hydroxyethoxyacetic acid also accounted for >99% of the total urinary excretion of inhaled dioxane in rats (Young et al., 1978). Conversely, when dioxane is intravenously injected in rats, the metabolic clearance decreased indicating metabolic saturation at high doses (1000 mg/kg). Saturation was found to occur at doses >10 mg/kg/bw resulting in accumulation of 1,4-dioxane (HSDB, 1995).

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