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Home > Encyclopedia > 1,3-Dioxolane

1,3-Dioxolane

1,3-Dioxolane structure

1,3-Dioxolane 

structure
  • CAS No:

    646-06-0

  • Formula:

    C3H6O2

  • Chemical Name:

    1,3-Dioxolane

  • Synonyms:

    1,3-Dioxolane;Dioxolane;1,3-Dioxole,dihydro-;Formal glycol;Glycolformal;1,3-Dioxolan;1,3-Dioxacyclopentane;Ethylene glycol formal;5-Crown-2;DIOX

  • Categories:

    Cosmetic Ingredient  >  Dissolving Agent

Description

Colourless Liquid


Dioxolane appears as a clear colorless liquid. Slightly denser than water. Vapors heavier than air.|Liquid|Colorless liquid.


Dioxolane appears as a clear colorless liquid. Slightly denser than water. Vapors heavier than air.|1,3-dioxolane is a cyclic acetal that is pentane in which the carbon atoms at positions 1 and 3 are replaced by oxygen atoms respectively. It is a dioxolane and a cyclic acetal.

1,3-Dioxolane Basic Attributes

74.08

74.08

211-463-5

Y57RBG19JL

1166

DTXSID4027284

Water-white liquid

29329970

Characteristics

18.5

-0.37

White to off-white Liquid

1.0600 g/cm3 @ Temp: 20 °C

-95 °C

78 °C @ Press: 765 Torr

35 °F

1.399-1.401

H2O: soluble

Refrigerator

70 mm Hg ( 20 °C)

2.6 (vs air)

Oral-Rat LD50: 3000 mg/kg; Oral-Mouse LD50: 3200 mg/kg

Inflammable in case of open flame, high temperature, oxidant; burning produces irritating smoke

2.1-20.5%(V)

2.45e-05 atm-m3/mole|Henry's Law constant = 2.4X10-5 atm-cu m/mole at 25 °C

Hydroxyl radical reaction rate constant = 1.12X10-11 cu cm/molec-sec at 25 °C (est)

Highly flammable. When exposed to air it undergoes autooxidation with formation of peroxides. In the distillation process peroxides will concentrate causing violent explosion. Soluble in water.

Ethers

Highly Flammable

Ethers, such as DIOXOLANE, can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.

Safety Information

II

3

UN 1166 3/PG 2

1

11

16

JH6760000

F

The warehouse is ventilated, low temperature and dry; stored separately from oxidants and acids

Below 4°C

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501

H225

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.

Potentially expolsive reaction with lithium perchlorate.|Lithium perchlorate-dioxolane electrolyte systems are unsafe for secondary battery applications, as an explosion occurred during overnight cyclic testing of a Li/TiS2 system. The effect was duplicated under all over-discharge or cell-reversal conditions.|... Can react with oxidizing materials.

EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans for 1,3-Dioxolane (November 2000). Summarizes information on usage patterns, toxicity, and ecological effects supplied by industry to the US EPA's HPV Challenge Program. Available from: http://cfpub.epa.gov/hpv-s/ as of September 06, 2006.

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016)|Flammable - 3rd degree, Reactive - 2nd degree

|Danger|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P264, P280, P281, P303+P361+P353, P305+P351+P338, P308+P313, P337+P313, P370+P378, P403+P235, P405, and P501|Aggregated GHS information provided by 578 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P210, P233, P240, P241, P242, P243, P264, P280, P281, P303+P361+P353, P305+P351+P338, P308+P313, P312, P332+P313, P337+P313, P370+P378, P403+P235, P405, and P501

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)

A very dangerous fire hazard when exposed to heat or flame.|Flammable, dangerous fire risk.

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 be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemial or carbon dioxide. /Dioxolane/

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. Attempt to stop leak if without undue personnel hazard. Use water spray to disperse vapors and dilute standing pools of liquid. /Dioxolane/|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. /Dioxolane/

/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Dioxolane/|/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Health: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution. /Dioxolane/|/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Dioxolane/|/GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Dioxolane/|For more DOT Emergency Guidelines (Complete) data for 1,3-DIOXOLANE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

A skin and severe eye irritant.

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. Dioxilane is produced, as an intermediate or a final product, by process units covered under this subpart.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.| 2 - Materials that readily undergo violent chemical changes at elevated temperatures and pressures.|W - No water: Materials that react violently or explosively with water.

1,3-Dioxolane was qualitatively detected in 4 samples of final effluents taken from 3 publicly owned treatment works (POTWs) and 1 oil refinery in Lockport (oil refinery), Roselle, Danville, and Decatur, Illinois(1).

Toxicity

moderately toxic

LD50 Rat inhalation 20650 mg/cu m/4 hr|LC50 Rat inhalation 68.4 mg/L/4 hr|LC50 Rat (male) inhalation 87 mg/L/4 hr|LC50 Guinea pig inhalation 166 mg/L/4 hr|For more Non-Human Toxicity Values (Complete) data for 1,3-DIOXOLANE (10 total), please visit the HSDB record page.

/AQUATIC SPECIES/ ... Dioxolane was tested for growth inhibition of / the green algae/ Selenastrum capricornutum ... Algae growth was measured out to 14 days past initial exposure at levels of 1000, 5000 or 10,000 mg/L with counts recorded on day 3 and later. Significant inhibition was seen only at 5000 mg/L and above ... 1000 mg/L was determined to be the NOEC.|/AQUATIC SPECIES/ ... Sheepshead minnows (Cyprinodon variegates, five per group) were exposed to dioxolane at concentrations of 7500, 11,000, 13,000, 15,000 and 25,000 mg/L ... the 48-hr LC50 was reported to be 12,000 mg/L and ... the 96-hour LC50 was reported to be 10,000 mg/L. A clear dose-response was established with a 24-hour mortality of 5/5 at 25,000 mg/L.

1,3-Dioxolane's production and use as a low-boiling solvent and extractant for oils, fats, waxes, dyes and cellulose derivatives(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 15(SRC), determined from a log Kow of -0.37(2) and a regression-derived equation(3), indicates that 1,3-dioxolane is expected to have very high mobility in soil(SRC). Volatilization of 1,3-dioxolane from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.45X10-5 atm-cu m/mole(4). 1,3-Dioxolane is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 79 mm Hg(5). Biodegradation data were not available(SRC, 2006).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 15(SRC), determined from a log Kow of -0.37(2) and a regression-derived equation(3), indicates that 1,3-dioxolane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 2.45X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 33 hours and 13 days, respectively(SRC). The aquatic oxidation rate for the reaction of 1,3-dioxolane with photochemically produced hydroxyl radicals has been experimentally determined to be 4.0X10+9 L/mol-s (pH not stated)(5). Based on this rate and a hydroxyl radical concn of 1X10-17 mol/L in water under continuous sunlight(6), the half-life for the aquatic oxidation of 1,3-dioxolane can be estimated to be 200 days(SRC). According to a classification scheme(7), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2006).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3-dioxolane, which has a vapor pressure of 79 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3-dioxolane 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 37 hours(SRC), calculated from its rate constant of 1.04X10-11 cu cm/molecule-sec at 25 deg(3).

The rate constant for the vapor-phase reaction of 1,3-dioxolane with photochemically-produced hydroxyl radicals has been measured as 1.04X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 37 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). The aquatic oxidation rate for the reaction of 1,3-dioxolane with photochemically produced hydroxyl radicals has been experimentally determined to be 4.0X10+9 L/mol-s (pH not stated)(3). Based on this rate and a hydroxyl radical concn of 1X10-17 mol/L in water under continuous sunlight(4), the half-life for the aquatic oxidation of 1,3-dioxolane can be estimated to be 200 days(SRC). 1,3-Dioxolane is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(5).

An estimated BCF of 3 was calculated in fish for 1,3-dioxolane(SRC), using a log Kow of -0.37(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of 1,3-dioxolane is estimated as 15(SRC), using a log Kow of -0.37(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,3-dioxolane is expected to have very high mobility in soil.

The Henry's Law constant for 1,3-dioxolane is 2.45X10-5 atm-cu m/mole(1). This Henry's Law constant indicates that 1,3-dioxolane is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 33 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 13 days(SRC). 1,3-Dioxolane's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 1,3-Dioxolane is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 79 mm Hg(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 74,950 workers (747 of these are female) are potentially exposed to 1,3-dioxolane in the US(1). Occupational exposure to 1,3-dioxolane may occur through inhalation and dermal contact with this compound at workplaces where 1,3-dioxolane is produced or used(SRC).

Drug Information

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. (See all compounds classified as Mutagens.)

The compound was able to penetrate human skin.|The site of uptake of inhaled vapors profoundly influences which respiratory tract tissues receive the highest doses. How the site of uptake depends on the physicochemical properties of inhaled vapors has been the subject of experiment and speculation for decades, but remains undefined. Using techniques that distinguish between vapor uptake in the nose and lung during cyclic breathing by Beagle dogs, uptake of the vapors of 2,4-dimethypentane, propyl ether, butanone, dioxolane, and ethanol was examined. These compounds have blood/air partition coefficients ranging from 1 to 2000. The effect of altering respiratory rates on vapor uptake was examined for 2,4-dimethypentane and dioxolane vapors. Deposition of vapors in the nasal cavity during inhalation was highly dependent on the partition coefficient. Vapor deposited in the nasal mucosa during inhalation was desorbed to a substantial extent during exhalation. Lung uptake of total inhaled vapor was limited by the amount available after passage through the nose, but in no case did it exceed 50% of the available amount. The data suggest that the diffusion of vapor molecules through the tissue barrier separating the air/tissue interface from the tissue/blood interface constitutes a significant resistance for both nasal uptake and lung uptake of many inhaled vapors. The data were used to validate a mathematical model describing nasal uptake of vapors.|... Three beagle dogs were exposed to dioxolane at nominal vapor concentrations of 500 ppm; vapor sampling was triggered for the entire inspiratory and expiratory portions of the breathing cycle during 10-min exposures. After correcting data to account for vapor that desorbed from the nasal passages during exhalation (after initially being absorbed in the nose during inhalation), net nasal uptake of dioxolane was 66.6%. Lung uptake was 2.1% for dioxolane. It can be concluded from this study that upper respiratory tract uptake of dioxolane is an important absorption mechanism for dogs under these experimental conditions. Upper respiratory tract absorption is likely to also be an important uptake mechanism in humans.

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Keep victim calm and warm. (ERG, 2016)

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Ethylene glycol, glycols, and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethylene glycol, glycols, and related compounds/

1,3-dioxolane

1,3-Dioxolane Use and Manufacturing

Methods of Manufacturing

Derived from paraformaldehyde and ethylene glycol. Paraformaldehyde and ethylene glycol were put into the reaction kettle at a molar ratio of 1:1.25, using strong acid ion exchange resin as a catalyst, and the reaction was carried out at 90-110°C under normal pressure. 70-74℃ azeotrope was distilled from the top of the distillation column, after salting out with sodium chloride and dehydration with anhydrous calcium chloride, and then distillation purification, cut 71-74℃ fractions, using molecular sieve to remove moisture to 200ppm, that is Get the finished product. Another operation is to make paraformaldehyde react with ethylene glycol in the presence of concentrated sulfuric acid, salt out with sodium chloride, dry with solid alkali, and rectify to obtain the product. Raw material consumption quota: paraformaldehyde (93-95%) 750kg/t, ethylene glycol 200kg/t.

Uses

Intermediate for the preparation of Acyclovir-d4


Intermediates


Adhesives and sealants

Production

10,000,000 - 50,000,000 lb|This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5535]

Adhesive manufacturing|1,3-Dioxolane: ACTIVE

Fire Hazards -> Flammable - 3rd degree, Reactive - 2nd degree

Computed Properties

Molecular Weight:74.08
XLogP3:-0.4
Hydrogen Bond Acceptor Count:2
Exact Mass:74.036779430
Monoisotopic Mass:74.036779430
Topological Polar Surface Area:18.5
Heavy Atom Count:5
Complexity:24.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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