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Home > Encyclopedia > Hydroxyethyl vinyl ether

Hydroxyethyl vinyl ether

Hydroxyethyl vinyl ether structure

Hydroxyethyl vinyl ether 

structure
  • CAS No:

    764-48-7

  • Formula:

    C4H8O2

  • Chemical Name:

    Hydroxyethyl vinyl ether

  • Synonyms:

    Ethanol,2-(ethenyloxy)-;Ethanol,2-(vinyloxy)-;2-(Ethenyloxy)ethanol;Ethylene glycol vinyl ether;Ethylene glycol monovinyl ether;2-(Vinyloxy)ethanol;2-Hydroxyethyl vinyl ether;Vinyloxyethanol;Monovinyl glycol ether;Hydroxyethyl vinyl ether;2-Vinyloxy-1-ethanol;2-(Ethenyloxy)ethan-1-ol;2-Ethenoxyethanol

  • Categories:

    Chemical Reagents  >  Organic Reagents

Hydroxyethyl vinyl ether Basic Attributes

88.11

88.11

212-124-4

34CNR2NAC8

DTXSID4075457

2909499000

Characteristics

29.5

0.1

0.9821 g/cm3 @ Temp: 20 °C

141.6 °C

50.0±16.9 °C

1.418

Soluble in ethanol, ether, and benzene

LD50 oral in rat: 3910mg/kg

Safety Information

3.2

3271

2

3

S16-S36

KM5495000

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

H226

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.

|Warning|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 56 companies from 2 notifications to the ECHA C&L Inventory.|H226: Flammable liquid and vapor [Warning Flammable liquids]

Toxicity

LD50 Mouse oral 2900 mg/kg|LD50 Rat oral 3910 mg/kg

Ethylene glycol monovinyl ether's production and use in the manufacture of plastics and lacquers(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 1(SRC), determined from a structure estimation method(2), indicates that ethylene glycol monovinyl ether is expected to have very high mobility in soil(SRC). Volatilization of ethylene glycol monovinyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.8X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of ethylene glycol monovinyl ether from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 2.2 mm Hg(SRC), determined from a fragment constant method(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that ethylene glycol monovinyl ether is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.8X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -0.55(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethylene glycol monovinyl ether, which has an estimated vapor pressure of 2.2 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase ethylene glycol monovinyl ether is degraded in the atmosphere by reactions with photochemically-produced hydroxyl radicals and ozone(SRC); the half-lives for these reactions in air are estimated to be 2.8 and 31 hrs, respectively(SRC), calculated from their rate constants of 4.5X10-11 cu cm/molecule-sec and 0.88X10-17 cu cm/molecule-sec at 25 °C, respectively(SRC), that were derived using a structure estimation method(3).

The rate constant for the vapor-phase reaction of ethylene glycol monovinyl ether with photochemically-produced hydroxyl radicals has been estimated as 4.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.8 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of ethylene glycol monovinyl ether with photochemically-produced ozone has been estimated as 0.88X10-17 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 31 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). Ethylene glycol monovinyl ether is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC).

An estimated BCF of 3 was calculated for ethylene glycol monovinyl ether(SRC), using an estimated log Kow of -0.55(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).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for ethylene glycol monovinyl ether can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that ethylene glycol monovinyl ether is expected to have very high mobility in soil(SRC).

The Henry's Law constant for ethylene glycol monovinyl ether is estimated as 2.5X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that ethylene glycol monovinyl ether is expected to be essentially nonvolatile from water surfaces(2). The potential for volatilization of ethylene glycol monovinyl ether from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 2.2 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to ethylene glycol monovinyl ether may occur through inhalation and dermal contact with this compound at workplaces where ethylene glycol monovinyl ether is produced or used. (SRC)

Drug Information

/2-(Vinyloxy)ethanol/ metab in the body occurs via hydrolysis to form acetaldehyde which is rapidly oxidized and is therefore not important in the pathogenesis of intoxication. The detached ethylene glycol selectively attacks the kidneys- either itself or through its separation products.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. 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 normal saline 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/|Basic treatment: Establish a patent airway. 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 normal saline 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 or in respiratory arrest. Positive pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Consider vasopressors to treat hypotension without signs of hypovolemia ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethylene glycol, glycols, and related compounds/

ethylene glycol monovinyl ether

Hydroxyethyl vinyl ether Use and Manufacturing

According to HSDB , EGME has been used in the manufacture of plastics and lacquers and also in the production of protective coatings.

Computed Properties

Molecular Weight:88.11
XLogP3:0.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:88.052429494
Monoisotopic Mass:88.052429494
Topological Polar Surface Area:29.5
Heavy Atom Count:6
Complexity:34.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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