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Butyl vinyl ether

Butyl vinyl ether structure

Butyl vinyl ether 

structure
  • CAS No:

    111-34-2

  • Formula:

    C6H12O

  • Chemical Name:

    Butyl vinyl ether

  • Synonyms:

    Butane,1-(ethenyloxy)-;Ether,butyl vinyl;1-(Ethenyloxy)butane;n-Butyl vinyl ether;BVE;Vinyl n-butyl ether;Vinyl butyl ether;Butoxyethene;Butoxyethylene;1-Butoxyethene;Butyl vinyl ether;1-(Vinyloxy)butane;NSC 8264;NBVE

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

BUTYL VINYL ETHER, STABILIZED is a liquid. Less dense than water. Vapors heavier than air. May irritate skin and eyes. Used to make other chemicals.


Butyl vinyl ether, stabilized appears as a liquid. Less dense than water. Vapors heavier than air. May irritate skin and eyes. Used to make other chemicals.


Butyl vinyl ether, stabilized appears as a liquid. Less dense than water. Vapors heavier than air. May irritate skin and eyes. Used to make other chemicals.

Butyl vinyl ether Basic Attributes

100.15900

100.16

203-860-7

321YRT7173

8264

2352

DTXSID5051575

Liquid

2909199090

Characteristics

9.23000

1.94660

Butyl vinyl ether, stabilized appears as a liquid. Less dense than water. Vapors heavier than air. May irritate skin and eyes. Used to make other chemicals.

0.7888 g/cm3 @ Temp: 20 °C

-92 °C

94 °C

-9ºC

1.4005-1.4025

H2O: 3 g/L (20 ºC);Very sol in ethyl alcohol, acetone; miscible in ethyl ether

0-6ºC

42 mm Hg ( 20 °C)

3.5 (vs air)

Moderately explosive by spontaneous chemical reaction.

Hydroxyl radical rate constant = 4.3X10-11 cu cm/molecule-sec @ 25 °C

Highly flammable. Slightly soluble in water. Ethers tend to form unstable peroxides when exposed to oxygen. Ethyl, isobutyl, ethyl tert-butyl, and ethyl tert-pentyl ether are particularly hazardous in this respect. Ether peroxides can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid.

Ethers

Highly Flammable

Ethers, such as BUTYL VINYL ETHER 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.

n-Butyl vinyl ether|D: Other compounds that may form peroxides|Kelly|Explosion possible during industrial synthesis. See Bretherick's.|Glikin, M. A. et al., Chem. Abs., 1978, 89, 30115

255 °C

Safety Information

II

3

UN 2352

2

R11; R19

S16-S33-S9

KN5950000

F

May form explosive peroxides.

P210

H225

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.|This compound should be susceptible to removal from waste water by air stripping. /Bis(2-chloroethyl)ether/

... Can react with oxidizing materials.

Excerpt from ERG Guide 127P [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 - 1st degree

|Danger|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P272, P280, P302+P352, P303+P361+P353, P321, P332+P313, P333+P313, P362, P363, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 148 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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

Flammable, dangerous fire risk.|Fire hazard: Dangerous, when exposed to heat or flame.

... Explosion hazard of industrial synthesis of butyl vinyl ether ... . /Details not given/|Moderately explosive by spontaneous chemical reaction.

Water may be ineffective ... alcohol foam is recommended ... . /From table/|... Carbon dioxide, dry chemical, foam, alcohol foam.

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.

/GUIDE 127P: 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. 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. /Butyl vinyl ether, inhibited; Butyl vinyl ether, stabilized/|/GUIDE 127P: 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. /Butyl vinyl ether, inhibited; Butyl vinyl ether, stabilized/|/GUIDE 127P: 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. /Butyl vinyl ether, inhibited; Butyl vinyl ether, stabilized/|/GUIDE 127P: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Butyl vinyl ether, inhibited; Butyl vinyl ether, stabilized/|For more DOT Emergency Guidelines (Complete) data for BUTYL VINYL ETHER (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.

Mildly toxic by ingestion, skin contact, and inhalation. A skin and eye irritant.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 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.

Butyl vinyl ether was detected, but not quantified, at 1 of 4 sites in the Houston, TX, area sampled in Nov 1974(1). It was not found in any of the samples from the 5 sites in the Los Angeles Basin sampled in March and April 1975 or the 2 sites in the Kanawha Valley, WV sampled in Sept 1974 and it was not detected in any of the night ambient air samples in the study(1).

Toxicity

LD50 Rat single oral 10.30 (8.40-12.63 g/kg in a single vehicle). /From table/|LD50 Rabbit single percutaneous 4.24 (3.02-5.95) ml/kg. /From table/|Concentrated vapor inhalation by rats, max for no death: 5 min. /From table/|Inhalation of metered vapor concn by rats: Concn: 8000 ppm Time: 4 hr Mortality: 0/6. /From table/|For more Non-Human Toxicity Values (Complete) data for BUTYL VINYL ETHER (6 total), please visit the HSDB record page.

Butyl vinyl ether's production and use in synthesis and copolymerization(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 53(SRC), determined from a water solubility of 3,000 mg/l(2) and a regression-derived equation(3), indicates that butyl vinyl ether is expected to have very high mobility in soil(SRC). Volatilization of butyl vinyl ether from moist soil surfaces is expected to be important(3,SRC) given an estimated Henry's Law constant of 2.2X10-3 atm-cu m/mole(SRC), calculated from its water solubility(2) and vapor pressure(4). The potential for volatilization of butyl vinyl ether from dry soil surfaces may exist(SRC) based on a vapor pressure of 49 mm Hg(4). Limited data are present in the scientific literature regarding the biodegradation of butyl vinyl ether(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 53(SRC), determined from a water solubility of 3,000 mg/l(2) and a regression-derived equation(3), indicates that butyl vinyl ether is not expected to adsorb to suspended solids and sediment in water(SRC). Butyl vinyl ether is expected to volatilize rapidly from water surfaces(3,SRC) based on an estimated Henry's Law constant of 2.2X10-3 atm-cu m/mole(SRC), calculated from its water solubility(2) and vapor pressure(4). Estimated volatilization half-lives for a model river and model lake are 3 hours and 4 days, respectively(3,SRC). Butyl vinyl ether may be susceptible to appreciable hydrolysis in certain environmental waters(5,SRC). The calculated half-lives for hydrolysis of butyl vinyl ether are 9.5 hours, 40 days, and 10.9 years at pH 5, 7, and 9, respectively(5,SRC). According to a classification scheme(6), an estimated BCF of 7(3,SRC), from butyl vinyl ether's water solubility(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Limited data are present in the scientific literature regarding the biodegradation of butyl vinyl ether(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), butyl vinyl ether, which has a vapor pressure of 49 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase butyl vinyl ether 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 9 hours(3,SRC). Butyl vinyl ether may be susceptible to photooxidation via vapor phase reaction with ozone; the half-life for this reaction in air is estimated to be 6.5 days(4,SRC). Direct photolysis will not be an important removal process since butyl vinyl ether does not absorb light at wavelengths >290 nm(5).

The rate constant for the vapor phase reactions of butyl vinyl ether with photochemically produced hydroxyl radicals has been measured to be 4.3X10-11 cu cm/molecule-sec at 25 °C(1) which corresponds to a half-life of 9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm (SRC). The rate constant for the vapor phase reactions of butyl vinyl ether with photochemically produced ozone has been estimated to be 1.75X10-18 cu cm/molecule-sec at 25 °C(2) which corresponds to a half-life of 6.5 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(SRC). Direct photolysis will not be an important removal process since aliphatic ethers do not absorb light at wavelengths >290 nm(3). Butyl vinyl ether is susceptible to appreciable hydrolysis in certain environmental waters, especially at acidic pH, based upon a measured acid catalyzed hydrolysis rate constant of 2.02 M-1 s-1 at 25 °C(4). This hydrolysis rate constant corresponds to half-lives for hydrolysis of 9.5 hr, 40 days, and 10.9 yr at pH 5, 7, and 9, respectively(4,SRC).

An estimated BCF of 7 was calculated for butyl vinyl ether(SRC), using a water solubility of 3,000 mg/l(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.

The Koc of butyl vinyl ether is estimated as approximately 53(SRC), using a water solubility of 3,000 mg/l(1) and a regression-derived equation(2,SRC). According to a classification scheme(3), this estimated Koc value suggests that butyl vinyl ether is expected to have very high mobility in soil(SRC).

The Henry's Law constant for butyl vinyl ether is estimated as 2.2X10-3 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 49 mm Hg(2), and water solubility, 3,000 mg/l(1). This Henry's Law constant indicates that butyl vinyl ether is expected to volatilize rapidly from water surfaces(3,SRC). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is approximately 3 hours(3,SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is approximately 4 days(3,SRC). Butyl vinyl ether's Henry's Law constant(1,2,SRC) indicates that rapid volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of butyl vinyl ether from dry soil surfaces may exist(SRC) based on a vapor pressure of 49 mm Hg(2).

DRINKING WATER: Butyl vinyl ether was tentatively identified, but not quantified, in a drinking water concentrate from Seattle, WA sampled in Nov 1976(1).|SURFACE WATER: Butyl vinyl ether has been detected, not quantified, in samples of water from the southern basin of Lake Michigan(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 851 workers (187 of these are female) are exposed to butyl vinyl ether in the USA(1). The most probable routes of general population exposure to butyl vinyl ether are via inhalation of contaminated air(1,SRC) and ingestion of contaminated drinking water(2,3,SRC). Exposure through dermal contact may occur in occupational settings(SRC). Inhalation and dermal exposure will be expected to be highest in workplaces where butyl vinyl ether is made and used(SRC).

Drug Information

Excerpt from ERG Guide 127P [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 127P [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. 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. Provide a low-stimulus environment. 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 ... . Treat frostbite by rapid rewarming ... . /Ethers and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W TKO /SRP: To keep open, "minimal flow rate"/. Use lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethers and related compounds/

butyl vinyl ether

Butyl vinyl ether Use and Manufacturing

Methods of Manufacturing

Reaction of acetylene with n-butyl alcohol.|Acetylene + n-butanol (ethynylation)

Uses

Butyl vinyl ether is used in the synthesis of copolymers.

Grade: Technical (98%)

Butane, 1-(ethenyloxy)-: ACTIVE

NIOSH Method 1610: A gas chromatographic method for the analysis of ethyl ether, consists of a stainless steel column, 1.2 m x 6 mm OD, packed with Porapak Q (50/80 mesh), with hydrogen-air flame ionization detection, and nitrogen as the carrier gas at a flow rate of 30 ml/min, is a NIOSH approved method. A sample injection volume of 5 ul is suggested, the column temperature is 175 °C, the injection temperature is 195 °C, and the detection temperature is 250 °C. This method has a estimated detection limit of 0.01 mg/sample, and a relative standard deviation of 0.024 at 1.8 to 7.1 mg/sample over a working range of 100 to 2500 mg/sample. /Diethyl ether/|EPA Method 1624: An isotope dilution gas chromatography/mass spectrometry method for the determination of volatile organic compounds in municipal and industrial discharges is described. This method is designed to meet the survey requirements of Effluent Guidelines Division (EGD) and the National Pollution Discharge Elimination System (NPDES). Under the prescribed conditions, unlabeled diethyl ether has a minimum level of 50 ug/l and a mean retention time of 820 sec. The labeled compound has a minimum level of 50 ug/l, a mean retention time of 804 sec, and a characteristic primary m/z of 74/84. /Diethyl ether/|EPA Method 8015: Nonhalogenated Volatile Organics. For the analysis of solid waste, a representative sample (solid or liquid) is collected in a standard 40 ml glass screw-cap VOA vial equipped with a Teflon-faced silicone septum. Sample agitation, as well as contamination of the collected sample with air, must be avoided. Two VOA vials are filled per sample location, then placed in separate plastic bags for shipment and storage. Samples can be analyzed by direct injection or purge-and trap gas chromatography. A temperature program is used in the gas chromatograph to separate the organic compounds. Column 1 is an 8-ft by 0.1-in I.D. stainless steel or glass column packed with 1% SP-1000 on Carbopack-B 60/80 mesh or equivalent. Column 2 is a 6-ft by 0.1-in I.D. stainless steel or glass column packed with n-octane on Porasil-C 100/120 mesh (Durapak) or equivalent. Detection is achieved by a flame ionization detector (FID). Under the prescribed conditions, diethyl ether can be detected using this method. No statistical analysis was determined; specific method performance information will be provided as it becomes available. /Diethyl ether/|AOAC 928.10. Ether in drugs is analyzed using a dichromate oxidation method (See 10th edition 32.370). /Diethyl ether/|EPA Method 5030: Purge and Trap: An inert gas is bubbled through the solution at ambient temperature, and the volatile components are efficiently transferred from the aqueous phase to the vapor phase. After purging is complete, the sorbent column is heated and backflushed with inert gas to desorb the components onto a GC column. Water samples can be analyzed directly, while preparation is necessary for water-miscible liquids, solids, and wastes and soil/sediments. /Diethyl ether/

Ether in blood or urine is analyzed by direct injection of the specimen into a gas chromatograph equipped with a flame-ionization detector and a molecular sieve column. This method has a sensitivity of 10 mg/l, linearity of 10-200 mg/l, cv of 3-5% within-run, and a relative recovery of 96-100%. /Diethyl ether/

Fire Hazards -> Flammable - 3rd degree, Reactive - 1st degree

Computed Properties

Molecular Weight:100.16
XLogP3:2.1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:100.088815002
Monoisotopic Mass:100.088815002
Topological Polar Surface Area:9.2
Heavy Atom Count:7
Complexity:41.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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