基本情報
- 標準SMILES
C1COCOC1- InChIKey
VDFVNEFVBPFDSB-UHFFFAOYSA-N- 分子式
- C4H8O2
- 平均分子量
- 88.11 g/mol
- 単同位体質量
- 88.0524295
概要
1,3-dioxane is a clear colorless liquid. (NTP, 1992)
名称と識別子
- 優先名称
- 1,3-Dioxane
- IUPAC
- 1,3-dioxane
- 現地名
- 1,3-ジオキサン
- 英語名
- 1,3-Dioxane
- 分子式
- C4H8O2
- 分子量
- 88.11
名称と別名
名称をさらに表示
データベース識別子
- CAS
505-22-6- PubChem CID
- 10450
- DTXSID
DTXSID3025174- ChEMBL
CHEMBL5291273- ChEBI
CHEBI:46924- UNII
- B2C8M17I09
- EC Number
- 208-005-1
- Nikkaji
- J6.221I
物性
構造計算による物性
- XLogP
- -0.2
- 極性表面積
- 18.5 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 2
- 回転可能結合数
- 0
- 重原子数
- 6
- 形式電荷
- 0
- 複雑度
- 32.5
実験および物理化学的性質
Density
1.0342 at 68 °F (NTP, 1992) - Denser than water; will sink
1.0342 AT 20 °C/4 °C
Solubility
greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)
SOL IN WATER, ALC, ETHANOL, ACETONE, BENZENE
Flash Point
35.6 °F (NTP, 1992)
2 °C
Boiling Point
221 °F at 755 mmHg (NTP, 1992)
105 °C AT 755 MM HG
Melting Point
-44 °F (NTP, 1992)
-42 °C
Vapor Pressure
38.5 [mmHg]
Vapor pressure= 39 mm Hg at 25 °C (estimated)
Physical Description
1,3-dioxane is a clear colorless liquid. (NTP, 1992)
Colorless liquid; [CAMEO] Miscible in water; [HSDB]
物理化学的性質
- 融点
- -45 °C · -45 °C (lit.)
- 沸点
- 105 · 105-106 °C (lit.)
- 比重(密度)
- 1.032 g/mL · 1.032 g/mL at 25 °C (lit.)
- 屈折率
- 20 · n20/D 1.418(lit.)
- 闪点
- 59 °F · 59 °F
- 貯蔵温度
- Flammables area
- 外見
- clear liquid
- 色
- Colorless to Almost colorless
- 水溶解度
- 水に完全に混和します。
- 比熱容量
- 1.63 J/ · Cp(liquid): 1.63 J/(g·K), at 25℃
- BRN
- 102532 · 102532
- Henry's Law Constant
- 1.8 · 1.8×100 mol/(m3Pa) at 25℃, O'Farrell and Waghorne (2010)
- 安定性
- 安定。可燃性。酸化剤と相容れない。空気と接触すると、爆発性の過酸化物が生成される場合があります - 不活性ガス中に保管してください。
- InChI
- InChI=1S/C4H8O2/c1-2-5-4-6-3-1/h1-4H2
- InChIKey
- VDFVNEFVBPFDSB-UHFFFAOYSA-N
- SMILES
- O1CCCOC1
- EPAの化学物質情報
- 1 · 1,3-Dioxane (505-22-6)
化学的性質
化学的特性colourless liquid
安全と法規制
GHS分類
GHS Classification
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P317, P321, P330, P332+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 44 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
OSHA Standards
Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 100 ppm (360 mg/cu m). Skin Designation. /Dioxane/
Vacated 1989 OSHA PEL TWA 25 ppm (90 mg/cu m), skin designation, is still enforced in some states. /Dioxane/
Atmospheric Standards
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. Dioxane is produced, as an intermediate or final product, by process units covered under this subpart. /Dioxane/
安全と保護具
First Aid
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.
Storage Conditions
Dioxane must be stored in tightly closed containers in a cool, dry, well ventilated area away from heat, sparks, open flames, moisture, and strong oxidizers. Storage facilities should be designed to contain spills completely within a surrounding dike and to prevent contamination of workroom air. Dioxane when stored must be checked for peroxide content in accordance with the manufacturer's recommendations. /Dioxane/
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Preventive Measures
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers.
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.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter.
Wear appropriate personal protective clothing to prevent skin contact. /Dioxane/
Wear appropriate eye protection to prevent eye contact. /Dioxane/
Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. /Dioxane/
Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. (Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.) /Dioxane/
For more Personal Protective Equipment (PPE) (Complete) data for 1,3-DIOXANE (6 total), please visit the HSDB record page.
毒性情報
Environmental Fate
TERRESTRIAL FATE: No experimental data are available pertaining to the chemical or biochemical degradation of 1,3-dioxane in soil. The miscibility of 1,3-dioxane in water(1) suggests that leaching through soil to associated groundwaters may be possible(SRC).
AQUATIC FATE: No experimental data are available pertaining to the chemical or biochemical degradation of 1,3-dioxane in natural water. The chemical structure of 1,3-dioxane suggests that aqueous hydrolysis will not occur(1,SRC). The miscibility of 1,3-dioxane in water(2) suggest that bioconcentration in aquatic organisms and adsorption to sediments will not be important. Volatilization from environmental waters is expected to be slow based on estimated half-lives of 7.2 days, 77.5 days, and 35.5 months from a shallow model river, a model environmental pond, and Lake Zurich, respectively(1,3,SRC).
ATMOSPHERIC FATE: Based on an estimated vapor pressure of 39 mm Hg at 25 °C(1,SRC), 1,3-dioxane can be expected to exist almost entirely in the vapor-phase in the ambient atmosphere(2,SRC). By analogy to 1,4-dioxane, vapor-phase 1,3-dioxane will be degraded relatively rapidly in the atmosphere by reaction with photochemically formed hydroxyl radicals(3,SRC); the half-life for this reaction in average air is approximately 2 days(3,SRC). Due to its miscibility in water(4), physical removal of 1,3-dioxane from the atmosphere via wet deposition may be possible(SRC).
Human Toxicity Excerpts
An occupational fatality in which a man had been exposed to dioxane for just 1 week /is described/. The 21 year old man, who had a history of heavy beer consumption, had used dioxane to clean a workbench and to keep his hands free of resin-type glue. He kept an uncovered bucket of dioxane between his knees for these purposes. Neither a respirator nor an exhaust ventilation system was employed. After 1 week of dioxane exposure, he was hospitalized with severe epigastric pain and rising blood pressure which reached 220/120 about 3 hours after admission. Within a few hours, he developed severe convulsions followed by unconsciousness and anuria. The anuria lasted 5 days during which time his blood nonprotein nitrogen rose to 181 mg/100 ml compared to a normal value of 15-40 mg/100 ml. His condition continued to deteriorate even after he regained kidney function, and he died on the 6th day of hospitalization. Autopsy findings included centrilobular liver necrosis and necrosis of the renal cortex with extensive interstitial hemorrhage and occassional hyalinization of glomeruli. There were microscopic findings in the brain that were considered to be secondary to anoxia and cerebral edema. /Dioxane/
The effects on five volunteers /of a 1 minute exposure to/ inhaled air containing 5,500 ppm dioxane /is described/. Signs and symptoms of exposure included eye irritation, a burning sensation in the nose and throat, and, in three subjects, slight vertigo that disappeared "quickly" after they left the exposure chamber. When the same five subjects were exposed to air containing 1,600 ppm dioxane for 10 minutes, they experienced an immediate slight burning of the eyes with lacrimation, and a slight irritation of the nose and throat. The alcohol-like odor of dioxane, easily noticeable at first, decreased in intensity with continued exposure. Lacrimation and nasal irritation persisted throughout the test. No vertigo was noticed, but one subject complained of an upset stomach after the exposure had been completed. The specifications of the exposure chamber, the purity of the dioxane, and the methods of generating and measuring the dioxane atmospheres were not reported. /Dioxane/
Environmental Bioconcentration
Based upon an estimated log Kow of -0.419(1), the BCF for 1,3-dioxane can be estimated to be 0.3 from a recommended regression-derived equation(2,SRC). In addition, 1,3-dioxane has been reported to be miscible in water(3). The estimated BCF and water solubility of 1,3-dioxane indicate that bioconcentration in aquatic organisms is not important(SRC).
Volatilization from Water/Soil
The Henry's Law Constant for 1,4-dioxane has been experimentally measured to be 4.88X10-6 atm cu m/mole at 25 °C(1); the Henry's Law Constant for 1,3-dioxane is expected to have a similar value(SRC). This value of Henry's Law Constant indicates that volatilization from environmental waters is expected to be relatively slow(2). Based on this Henry's Law Constant, the volatilization half-life from a model river (1 m deep flowing 1 m/sec with a wind velocity of 3 m/sec) can be estimated to be about 7.2 days(2,SRC); the volatilization half-lives from a model environmental pond and from Lake Zurich (Switzerland) can be estimated to be 77.5 days and 35.5 months, respectively(3,SRC).
Non-Human Toxicity Excerpts
Results of the mutagenesis testing in Drosophila of 20 coded compounds (including 1,3-dioxane, 94-96% pure) for the National Toxicology Program (NTP) are presented. The chemicals were first assayed in the sex-linked recessive lethal (SLRL) test in an adult feeding experiment. If results were negative, the chemical was retested by injecting adults. ... 1,3-Dioxane was not mutagenic to Drosophila melanogaster /in the sex linked recessive lethal test by either injection or feeding/.
Effects of nonlethal and lethal doses of dioxane administered intragastrically to an unspecified number of rabbits were reported. Dioxane doses of 0.2 ml/kg in 10 ml water, 1.0 ml/kg in 5 ml water, or 2 ml/kg in 20 ml water were administered as single doses to an unspecified number of rats. Doses of 0.2 ml/kg, repeated at weekly intervals for an unspecified number of weeks, did not appear to affect the rabbits at all; one rabbit received as many as 15 weekly doses of 0.2 ml/kg without effect. A state described as drunkenness was seen with 1 ml doses, but single doses of 2 ml/kg administered to five nonfasting rabbits killed them. The minimal lethal intragastric dose of dioxane was found to be 2.0 ml/kg in 20 ml water. Microscopic changes observed in the kidney and liver were similar to those seen in rabbits given iv injections of dioxane; they were hydropic degeneration of the convoluted tubules of the kidneys and vacuolization of liver cells. /Dioxane/
Effects of dioxane administered intraveneously to rabbits were reported. Four rabbits received a single dose of 1, 2, 3, or 5 ml of 80% dioxane diluted with saline to a total volume of 10 ml. Three other rabbits each were given two 5 ml injections of dioxane mixed with 5 ml of saline with an interval of 48 hours between injections. One rabbit, used as a control, received 10 ml of saline. The immediate effect of dioxane injection in all rabbits was violent struggling, which began as soon as the first few drops were injected. With doses of 4 or 5 ml of dioxane, the struggling was followed by convulsions and collapse; then the rabbits returned to normal. The four rabbits given the single doses of 80% dioxane were killed 1 month later. Degeneration of the renal cortices with hemorrhages was observed by microscopic examination. In the rabbit administered the 3 ml dioxane dose, the degenerative changes extended into the medulla, and the liver showed extensive and gross cellular degeneration starting at the periphery of the lobules. No abnormality was found in other organs. The livers of the rabbits given the 1 and 5 ml doses showed no microscopic abnormalities, and areas of cloudy swelling were seen in the liver of the rabbit given 2 ml of dioxane. /Dioxane/
The effects of dioxane resulting from its absorption through the skin of rabbits were reported. Undiluted dioxane was applied to a shaved area of the belly which represented approximately 15% of the rabbit's body surface. Dioxane was in contact with the skin of two to four rabbits, used in groups, for 1.7, 3.0, 4.1, and 4.8 hours. A control rabbit was treated with water for 6 hours and another for 7.7 hours. Three rabbits showed evidence of intracutaneous and subcutaneous hemorrhages at the end of exposure. When dioxane was administered to two rabbits for 1.7 hours, unsteadiness and incoordination were noticed in both animals; one died within 24 hours and the other was alive 2 weeks after exposure. When four rabbits were exposed to undiluted dioxane for 3 hours, all showed unsteadiness and incoordination; two died within 3 days, one on the 5th day, and the other was alive 2 weeks after exposure. One rabbit exposed for 4.1 hours and another for 4.8 hours appeared to be in a state of CNS depression with very weak or absent corneal reflexes and both died at the end of exposure. Dioxane caused skin erythema in the two surviving rabbits that cleared in a matter of days with a superficial scaling and without any evidence of permanent damage. /Dioxane/
An unspecified number of guinea pigs /were exposed/ to dioxane at concentrations of 1,000, 2,000, 3,000, 10,000, and 30,000 ppm, and observed the duration of exposure in minutes up to a maximum of 8 hours required to produce signs such as nasal irritation, eye irritation, retching movements, changes in respiration, and CNS depression. The composition of the dioxane vapor air mixture was calculated from the quantity of liquid vaporized and the quantity of air contained in, or flowing through, the animal exposure chamber. The calculated composition of the dioxane air mixture was always checked by sorption of the vapor from a measured volume of the mixture by air equilibrated activated charcoal and determination of the gain in weight. Guinea pigs that were exposed at 30,000 ppm for 3 hours developed a state of marked CNS depression during exposure, and the animals died within 2 days. Congestion and edema of the lungs, hyperemia of the surface of the brain, and paleness of the liver were seen in guinea pigs that were killed immediately after the exposure at 30,000 ppm for 30 minutes; patches of congestion in the lung and hyperemia of the surface of the brain occurred in those that were killed 4 or 5 days after the test; and there were no pathologic changes in the animals killed 9 or 10 days after exposure. Congestion of the lung and a few hemorrhagic areas in the mucous membranes of the stomach were seen in the guinea pigs that died within 1 day of exposure at 30,000 ppm dioxane and bronchopneumonia and severe congestion of the surface vessels of the brain in the animal that died 2 days after exposure. Fifteen control animals showed no gross pathologic changes resembling those seen in the exposed animals. /Dioxane/
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of 1,3,5-trioxane with photochemically produced hydroxyl radicals has been experimentally measured to be 7.9X10-12 cu cm/molecule-sec at 25 °C, which corresponds to an atmospheric half-life of about 2 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC); 1,3-dioxane is expected to have a similar rate of reaction with atmospheric hydroxyl radicals because of the structural similartiy(SRC). Ethers are generally resistant to aqueous environmental hydrolysis(2); therefore, 1,3-dioxane is not expected to undergo aqueous hydrolysis in environmental waters(SRC).
Environmental Fate/Exposure Summary
No data are available pertaining to either artificial or natural sources of environmental release of 1,3-dioxane. Limited prediction of environmental fate is based entirely on physical properties, chemical structure and analogy to similar compounds since experimental data are not available. If released to the atmosphere, 1,3-dioxane is expected to exist in the gas phase where it will be degraded relatively rapidly (estimated half-life of 2 days) by reaction with photochemically formed hydroxyl radicals. If released to soil, leaching may be possible since 1,3-dioxane is miscible in water. If released to water, volatilization is expected to be slow based on estimated half-lives of 7.2 days, 77.5 days, and 35.5 months from a shallow model river, a model environmental pond, and Lake Zurich, respectively. Aquatic hydrolysis, bioconcentration, and adsorption to sediment are not expected to be important. No data are available pertaining to the biodegradation of 1,3-dioxane in the environment. There are no data available to suggest that the general population of the USA is currently exposed to 1,3-dioxane. (SRC)
法規制情報
Atmospheric Standards
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. Dioxane is produced, as an intermediate or final product, by process units covered under this subpart. /Dioxane/
安全データ
- wgk
- 3
- rtecs
- JG8224000
- ridadr
- UN 1165 3/PG 2
- hs_code
- 2932.99.9090
- risk_code
- 11-20/21/22
- 消防法
- 危-4-1-II
- hazard_code
- F,Xn
- safety_code
- 16
- hazard_class
- 3.1
- packing_group
- II
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralFlam. Liq. 2
- ストレージクラス
- 3 - Flammable liquids
- 有毒物質データの
- 505-22-6(Hazardous Substances Data)
化学と産業
薬理情報
Metabolism/Metabolites
beta-Hydroxyethoxyacetic acid, rather than oxalic acid or diglycolic acid, was the major urinary metabolite of dioxane in rats. Uniformly labeled (14)C dioxane was administered to two rats by oral intubation. Composite 24 hr urine samples were collected and analyzed for metabolites using thin layer ion exchange column chromatography and gas chromatography-mass spectrometry, and by nuclear magnetic resonance spectroscopy. One major and two minor (14)C containing compounds were confirmed by thin layer chromatography. The two minor compounds were identical to (14)C dioxane and (14)C diethylene glycol. The major compound was identified as beta-hydroxyethoxyacetic acid using the other four analytical methods. beta-Hydroxyethoxyacetic acid accounted for approximately 85% of the radioactivity in the urine, with dioxane and diethylene glycol accounting for the remaining 15%. /Dioxane/
用途と製造
Uses
Used as a monomer for acetyl resins (no evidence of current use); [HSDB]
MONOMER FOR ACETYL RESINS (NO EVIDENCE OF CURRENT USE)
U.S. Production
(1977) NOT PRODUCED COMMERCIALLY IN USA
(1979) NOT PRODUCED COMMERCIALLY IN USA
応用分野
使用1,3-Dioxane has been employed as solvent in the synthesis of 8- and 9-membered dioxazocines and dioxazonines.
一般的な説明Clear colorless liquid.
調製方法
製造方法1,3-dioxane is prepared by the reaction of formaldehyde and 1,3-propanediol in the presence of Brnsted or Lewis acid catalysts.
純化方法Dry the dioxane with sodium and fractionally distil it. [Beilstein 19/1 V 11.]
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