Ethyl tert-butyl ether
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Ethyl tert-butyl ether
structure -
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CAS No:
637-92-3
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Formula:
C6H14O
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Chemical Name:
Ethyl tert-butyl ether
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Synonyms:
Propane,2-ethoxy-2-methyl-;Ether,tert-butyl ethyl;2-Ethoxy-2-methylpropane;tert-Butyl ethyl ether;Ethyl tert-butyl oxide;Ethyl 1,1-dimethylethyl ether;1,1-Dimethylethyl ethyl ether;Ethyl tert-butyl ether;NSC 1069
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CAS No:
Description
tert-Butyl ethyl ether is a colourless to light yellow liquid at a temperature range of -94 to 72.6 °C. It is soluble in ethanol, ethyl ether, and water. tert-Butyl ethyl ether has a strong, highly objectionable odor and taste at relatively low concentrations. This chemical is highly flammable and reacts with strong oxidizing agents. tert-Butyl ethyl ether is stable when stored at room temperature in tightly closed containers.
2-methyl-2-ethoxypropane is a clear light yellow liquid. (NTP, 1992)|GasVapor; Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.|Clear light yellow liquid.
2-methyl-2-ethoxypropane is a clear light yellow liquid. (NTP, 1992)|Tert-butyl ethyl ether is an ether having ethyl and tert-butyl as the two alkyl components. It is used as an engine fuel additive to reduce emissions of carbon monoxide and soot. It has a role as a fuel additive. It is an ether and a volatile organic compound.
Ethyl tert-butyl ether Basic Attributes
102.175
102.17
211-309-7
3R9B16WR19
1706
1069
1179
DTXSID0025604
Liquid
2909199090
Characteristics
9.23000
1.68
2-methyl-2-ethoxypropane is a clear light yellow liquid. (NTP, 1992)
0.7404 g/cm3 @ Temp: 20 °C
-94 °C
73.1 °C
-19.4±0.0 °C
1.387
Miscible with alcohol, ethyl ether. Slightly miscible with water.
Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Store in cool place.
155 mm Hg ( 25 °C)
Relative vapour density (air = 1): 3.5
Explosive limits , vol% in air: 1.2-7.7
Characteristic strong odor ... reminiscent of ether, gasoline, or varnish or as being sweet
Characterized as highly objectionable
8.84e-12 cm3/molecule*sec
0.00 atm-m3/mole|Henry's Law constant = 1.64X10-3 atm-cu m/mol at 25 °C
BP also reported as 73.1 °C. Specific heat (liquid) at 25 °C: 0.51 cal/g|When heated to decomposition it emits acrid smoke and irritating vapors.|Hydroxyl radical reaction rate constant = 8.84X10-12 cu cm/molec-sec at 25 °C
Highly flammable. This chemical may react with air to form dangerous peroxides. (NTP, 1992). Insoluble in water.
Ethers
Highly Flammable
2-METHYL-2-ETHOXYPROPANE can act as a base to form salts with strong acids and addition complexes with Lewis acids. May react violently with strong oxidizing agents. Relatively inert in other reactions, which typically involve the breaking of the carbon-oxygen bond.
t-Butyl ethyl ether|B*: Compounds that form peroxides on concentration (distillation/evaporation)|Cameo
375 °C
The vapour is heavier than air and may travel along the ground; distant ignition possible. As a result of flow, agitation, etc., electrostatic charges can be generated.
73.4 cal/g
Safety Information
II
3
UN 1179 3/PG 2
1
R11
S16-S26
KN4730200
F: Flammable;Xi: Irritant;
Fireproof. Separated from oxidants. Cool. Well closed. Keep in the dark. Store in an area without drain or sewer access.
Stable, but may react with air to form peroxides. Once opened, store under an inert atmosphere and test for the presence of peroxides before use. Highly flammable. Incompatible with strong oxidizing agents.
P210-P261
H225-H336
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.
Materials to avoid: Strong oxidizing agents Hazardous decomposition
European Commission, ESIS; IUCLID Dataset, 2-Ethoxy-2-methylpropane (637-92-3) (2000 CD-ROM edition) contains information on use, toxicology, and environmental effects of this chemical as supplied to the European Union by industry.[Available from, as of September 27, 2010: http://esis.jrc.ec.europa.eu/]
This chemical is flammable. (NTP, 1992)|Highly flammable. Vapour/air mixtures are explosive.|Flammable - 3rd degree
|Danger|H224 (15.17%): Extremely flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 148 companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
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)
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. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing 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. STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, and store it at refrigerated temperatures. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)
RECOMMENDED RESPIRATOR: When working with this chemical, wear a NIOSH-approved full face chemical cartridge respirator equipped with the appropriate organic vapor cartridges. If that is not available, a half face respirator similarly equipped plus airtight goggles can be substituted. However, please note that half face respirators provide a substantially lower level of protection than do full face respirators. (NTP, 1992)|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Hand protection: Handle with gloves. Eye protection: Face shield and safety glasses Skin and body protection: Choose body protection according to the amount and concentration of the dangerous substance at the work place.
Flammable liquid
Lower explosive limit: 1.24% Vol; Upper explosive limit: 7.7% Vol|Vapors may form explosive mixture with air.|Explosive limits , vol% in air: 1.2-7.7
For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Use water spray to cool unopened containers. Wear self contained breathing apparatus for fire fighting if necessary.
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with non-combustible absorbent material, (e.g. sand, earth, diatomaceous earth, vermiculite) and place in container for disposal according to local / national regulations.
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.|Avoid contact with skin and eyes. Avoid inhalation of vapour or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.
Remove all ignition sources. Consult an expert! Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.
Fireproof. Separated from oxidants. Cool. Well closed. Keep in the dark. Store in an area without drain or sewer access.
A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C when dispersed.
The substance is irritating to the eyes, skin and respiratory tract. If swallowed the substance easily enters the airways and could result in aspiration pneumonitis. The substance may cause effects on the central nervous system. Exposure could cause lowering of consciousness.
Repeated or prolonged contact with skin may cause dermatitis.
NO open flames, NO sparks and NO smoking. Closed system, ventilation, explosion-proof electrical equipment and lighting. Do NOT use compressed air for filling, discharging, or handling.
PREVENT GENERATION OF MISTS!
Use ventilation, local exhaust or breathing protection.
Protective gloves.
Wear safety spectacles or eye protection in combination with breathing protection.
| 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.| 0 - Materials that in themselves are normally stable, even under fire conditions.
Ethyl tert-butyl ether was not detected in 249 storm water samples collected from 46 different sampling locations in North Carolina from November 1998 through October 1999. Samples were collected from urban land-use areas where fuel oxygenates might have been expected to occur(1). It is present in the gas phase at 200 and 34,600 ug/km in catalyst-equipped and non-catalyst-equipped emissions, respectively, tailpipe emissions from an in-use fleet of gasoline-powered automobiles and light-duty trucks (production year ranged from 1969 through 1994) tested in California(2).
URBAN/SUBURBAN: Ethyl tert-butyl ether was tested for but not detected in air samples from Boston, MA and Houston, TX, sampled every 14 days from August 1990 through April 1991(1).
Toxicity
LD50 Rat oral > 2000 mg/kg bw|LD50 Rat dermal >20 mg/kg bw|LC50 Rat inhalation >5880 mg/cu m/4 hr|LD50 Rabbit dermal >2,000 mg/kg
Ethyl tert-butyl ether's production and use as a gasoline additive(1) may result in its release to the environment through various waste streams(SRC). It has been suggested that ethyl tert-butyl ether may leach from silane cross-linked polyethylene plastic plumbing pipe(2).
TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 9 to 160(2,3) indicates that ethyl tert-butyl ether is expected to have very high to moderate mobility in soil(SRC). Volatilization of ethyl tert-butyl ether from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.64X10-3 atm-cu m/mole(4). Ethyl tert-butyl ether is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 124 mm Hg at 25 °C(5). No biodegradation was observed when incubated in soils with previous exposure to methyl tert-butyl ether(6), suggesting that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), a Koc range of 9 to 160(2,3) indicates that ethyl tert-butyl ether is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 1.64X10-3 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 3 hrs and 4 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 9(SRC), from an estimated log Kow of 1.92(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Ethyl tert-butyl ether was not biodegraded using inoculums derived from a gasoline-impacted aquifer, fuel impacted river sediment, nor industrial and sewage impacted creek sediments(9), suggesting that biodegradation is not an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl tert-butyl ether, which has a vapor pressure of 124 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl tert-butyl 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 2 days(SRC), calculated from its rate constant of 8.84X10-12 cu cm/molecule-sec at 25 °C(3). Ethyl tert-butyl ether does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of ethyl tert-butyl ether with photochemically-produced hydroxyl radicals is 8.84X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of ethyl tert-butyl ether with photochemically-produced nitrate radicals is 2.48X10-12 cu cm/molecule-sec at 257-367 K. Degradation products identified were tert-butyl formate, tert-butyl acetate, formaldehyde, and methyl nitrate(2). Ethyl tert-butyl ether is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Ethyl tert-butyl ether does not contain chromophores that absorb at wavelengths >290 nm(3), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 9 was calculated in fish for ethyl tert-butyl ether(SRC), using an estimated log Kow of 1.92(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).
Koc values of ethyl tert-butyl have been reported to range from 9 to 160(1,2). According to a classification scheme(3), these Koc values suggest that ethyl tert-butyl ether is expected to have very high to moderate mobility in soil.
The Henry's Law constant for ethyl tert-butyl ether is 1.64X10-3 atm-cu m/mole(1). This Henry's Law constant indicates that ethyl tert-butyl ether is expected to volatilize rapidly 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 3 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 4 days(SRC). Modeling results indicate that in shallow, fast-moving streams, the compound volatilizes at a faster rate than methyl tert-butyl ether; in deep, slow-moving streams, rates are similar to the methyl ester as well as benzene, toluene, ethylbenzene, and xylene(3). Ethyl tert-butyl ether's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Ethyl tert-butyl ether is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 124 mm Hg(4).
GROUNDWATER: Ethyl tert-butyl ether was not detected in contaminated groundwater samples collected from Dusseldorf, Germany in June, 2003; detection limit of 0.009 ug/L(1). The compound exhibited a 8.9% detection frequency as a result of data compiled from 7,200 monitoring wells at 868 leaking underground fuel tank sites in Los Angeles, CA; concentrations were as follows (ug/L): 0.35 minimum; 7,500 maximum; 260 mean(2). Ethyl tert-butyl ether was detected in 2 out of 37 Dutch samples in concentrations between 0.1 and 1 ug/L collected from 2002 to 2007(3).|DRINKING WATER: Ethyl tert-butyl ether was detected not quantified in 120 of 579 groundwater sources and 375 surface-water sources, randomly collected from May 3, 1999 through October 2000 from throughout the US, Native American lands, and Puerto Rico. The compound was detected only where methyl tert-butyl ether was also detected.(1).|SURFACE WATER: Ethyl tert-butyl ether was detected in samples from 196 Dutch water collection areas at concentrations near to the odor and flavor thresholds of 0.1-1 ug/L; sampling was conducted from 2002-2007. Concentrations of ethyl tert-butyl ether surface water from the Rhine River at Loeth ranged from 0-5.1 ug/L during 2005-2008. A maximum of 29 ug/L was reported on November 1, 2006, corresponding to a chemical spill(1).
According to the 2006 TSCA Inventory Update Report, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use for ethyl tert-butyl ether is 100-999; the data may be greatly underestimated(1).|Occupational exposure to ethyl tert-butyl ether may occur through inhalation and dermal contact with this compound at workplaces where ethyl tert-butyl ether is produced or used. The compound was not detected in air samples from within a North Carolina furniture factory, outdoor air from a paint incineration facility, in a machine shop, nor in office air from Boston, MA and Houston, TX, sampled every 14 days from August 1990 through April 1991(1). Limited monitoring data indicate that the general population may be exposed to ethyl tert-butyl ether via inhalation of ambient air and ingestion of drinking water(SRC).
Drug Information
... Inhalation is the most likely mode of exposure, with about 30% of inhaled ethyl tert-butyl ether (ETBE) being retained by the lungs and distributed around the body. ...|After inhalation exposure methyl tert-butyl ether (MTBE), ethyl tert-butyl ether (ETBE) and tert-amyl methyl ether (TAME) are rapidly taken up by both rats and humans; after termination of exposure, clearance by exhalation and biotransformation to urinary metabolites is rapid in rats. In humans, clearance by exhalation is slower in comparison to rats. Biotransformation of MTBE and ETBE is both qualitatively and quantitatively similar in humans and rats after inhalation exposure under identical conditions. The extent of biotransformation of TAME is also quantitatively similar in rats and humans; the metabolic pathways, however, are different. ...|To contribute to the characterization of potential adverse effects of ethyl tert-butyl ether (ETBE), its biotransformation was compared in humans and rats after inhalation exposure. Human volunteers (3 males and 3 females) and rats (5 males and 5 females) were exposed to 4 (4.5+/-0.6) and 40 (40.6+/-3.0) ppm ETBE for 4 hr in a dynamic exposure system. Urine samples from rats and humans were collected for 72 hr at 6-hr intervals, and blood samples were taken in regular intervals for 48 hr. In urine, ETBE and the ETBE-metabolites tert-butanol (t-butanol), 2-methyl-1,2-propane diol, and 2-hydroxyisobutyrate were quantified; ETBE and t-butanol were determined in blood samples. After the end of the exposure period to inhalation of 40-ppm ETBE, blood concentrations of ETBE were found at 5.3+/-1.2 uM in rats and 12.1+/-4.0 uM in humans. The ETBE blood concentrations, after inhalation of 4-ppm ETBE, were 1.0+/-0.7 uM in rats and 1.3+/-0.7 uM in humans. ETBE was rapidly cleared from blood. After the end of the 40-ppm ETBE exposure period, the blood concentrations of t-butanol were 13.9+/-2.2 uM in humans and 21.7+/-4.9 uM in rats. After 4-ppm ETBE exposure, blood concentrations of t-butanol were 1.8+/-0.2 uM in humans and 5.7+/-0.8 uM in rats. t-Butanol was cleared from human blood with a half-life of 9.8+/-1.4 hr in humans after 40-ppm ETBE exposure. In urine samples from controls and in samples collected from the volunteers and rats before the exposure, low concentrations of t-butanol, 2-methyl-1,2-propane diol, and 2-hydroxyisobutyrate were present. In the urine of both humans and rats exposed to ETBE, the concentrations of these compounds were significantly increased. 2-Hydroxy-isobutyrate was recovered in urine as the major excretory product formed from ETBE; t-butanol and 2-methyl-1,2-propane diol were minor metabolites. All metabolites of ETBE excreted with urine were rapidly eliminated in both species after the end of the ETBE exposure. Excretion half-lives for the different urinary metabolites of ETBE were between 10.2 and 28.3 hr in humans and 2.6 and 4.7 hr in rats. The obtained data indicate that ETBE biotransformation and excretion are similar for rats and humans, and that ETBE and its metabolites are rapidly excreted by both species. Between 41 and 53% of the ETBE retained after the end of the exposure was recovered as metabolites in the urine of both humans and rats.|... Eight healthy male volunteers were exposed to ethyl tert-butyl ether (ETBE) vapor (0, 5, 25, and 50 ppm) during 2 hr of light physical exercise. ETBE and the proposed metabolites tert-butyl alcohol (TBA) and acetone were analyzed in exhaled air, blood, and urine. Compared to a previous MTBE study lower respiratory uptake of ETBE (32-34%) was seen as well as a slightly higher respiratory exhalation (45-50% of absorbed ETBE). The kinetic profile of ETBE could be described by four phases in blood (average half-times of 2 min, 18 min, 1.7 hr, and 28 hr) and two phases in urine (8 min and 8.6 hr). Postexposure half-times of TBA in blood and urine were on average 12 and 8 hr, respectively. The 48-hr pulmonary excretion of TBA accounted for 1.4-3.8% of the absorbed ETBE, on an equimolar basis. Urinary excretion of ETBE and TBA was low, below 1% of the ETBE uptake, indicating further metabolism of TBA or other routes of metabolism and elimination. The kinetics of ETBE and TBA were linear up to 50 ppm. ...|For more Absorption, Distribution and Excretion (Complete) data for Ethyl tert-butyl ether (7 total), please visit the HSDB record page.
Following cessation of exposure, the blood concentration of ethyl tert-butyl ether (ETBE) falls rapidly, largely as a result of its metabolism to tertiary-butyl alcohol (TBA) and acetaldehyde. TBA may be further metabolized, first to 2-methyl-1,2-propanediol and then to 2-hydroxyisobutyrate, the two dominant metabolites found in urine of volunteers and rats. ...|The biotransformation of methyl tert-butyl ether (MTBE), ethyl tert-butyl ether (ETBE), and tert-amyl methyl ether (TAME) was studied in humans and in rats after inhalation of 4 and 40 ppm of MTBE, ETBE, and TAME, respectively, for 4 hours, and the biotransformation of MTBE and TAME was studied after ingestion exposure in humans to 5 and 15 mg in water. tert-Butyl alcohol (TBA), a TBA conjugate, 2-methyl-1,2-propanediol, and 2-hydroxyisobutyrate were found to be metabolites of MTBE and ETBE. tert-Amyl alcohol (TAA), free and glucuronidated 2-methyl-2,3-butanediol (a glucuronide of TAA), 2-hydroxy-2-methyl butyrate, and 3-hydroxy-3-methyl butyrate were found to be metabolites of TAME. After inhalation, MTBE, ETBE, and TAME were rapidly taken up by both rats and humans; after termination of exposure, clearance from blood of the ethers by exhalation and biotransformation to urinary metabolites occurred with half-times of less than 7 hours in rats and humans. Biotransformation of MTBE and ETBE was similar in humans and rats after inhalation exposure. 2-Hydroxyisobutyrate was recovered as a major product in urine. All metabolites of MTBE and ETBE excreted with urine were eliminated with half-times of less than 20 hours. Biotransformation of TAME was qualitatively similar in rats and humans, but the metabolic pathways were different. In humans, 2-methyl-2,3-butanediol, 2-hydroxy-2-methyl butyrate, and 3-hydroxy-3methyl butyrate were recovered as major urinary products. In rats, however, 2-methyl-2,3-butanediol and its glucuronide were major TAME metabolites recovered in urine. After ingestion of MTBE and TAME, both compounds were rapidly absorbed from the gastrointestinal tract. Hepatic first-pass metabolism of these ethers was not observed, and a significant part of the administered dose was transferred into blood and cleared by exhalation. Metabolic pathways for MTBE and TAME and kinetics of excretion were identical after ingestion and inhalation exposures. ...|Oxidative demethylation of methyl tert-butyl ether (MTBE) and tert-amyl methyl ether (TAME) and deethylation of ethyl tert-butyl ether (ETBE) by CYP enzymes results in the formation of tertiary alcohols and aldehydes, both potentially toxic. The metabolism of these three alkoxyethers was studied in a panel of 12 human liver microsomes. The relatively low apparent Km(1) was 0.25+/-0.17 (mean+/-SD), 0.11+/-0.08 and 0.10+/-0.07 mM and the high apparent Km(2) was 2.9+/-1.8, 5.0+/-2.7 and 1.7+/-1.0 mM for MTBE, ETBE and TAME, respectively. Kinetic data, correlation studies, chemical inhibition and metabolism by heterologously expressed human CYPs support the assertion that the major enzyme involved in MTBE, ETBE and TAME metabolisms is CYP2A6, with a minor contribution of CYP3A4 at low substrate concentration.|/The/ human liver is active in metabolizing methyl tert-butyl ether (MTBE) to tert-butyl alcohol (TBA), a major circulating metabolite and an exposure marker of MTBE. The activity is localized in the microsomal fraction but not in the cytosol. Formation of TBA in human liver microsomes is NADPH-dependent and is significantly inhibited by carbon monoxide, which inhibits cytochrome P450 (CYP) enzymes. These results provide strong evidence that CYP enzymes play a critical role in the metabolism of MTBE in human livers. Human liver is also active in the oxidative metabolism of 2 other gasoline ethers, ethyl tert-butyl ether (ETBE) and tert-amyl methyl ether (TAME). ... A large interindividual variation in metabolizing these gasoline ethers /was observed/ in 15 microsomal samples prepared from normal human livers. The activity level (pmol metabolite/min/mg) ranged from 204 to 2,890 for MTBE; 179 to 3,134 for ETBE; and 271 to 8,532 for TAME. The microsomal activities in metabolizing MTBE, ETBE, and TAME correlated highly with each other (r = 0.91 to 0.96), suggesting that these ethers are metabolized by the same enzyme(s). Correlation analysis of the ether-metabolizing activities with individual CYP enzyme activities in the human liver microsomes showed that the highest degree of correlation was with CYP isoform 2A6 (CYP2A6)+ (r = 0.94 for MTBE, 0.95 for ETBE, and 0.90 for TAME), which is constitutively expressed in human livers and known to be polymorphic. CYP2A6 displayed the highest turnover number in metabolizing gasoline ethers among a battery of human CYP enzymes expressed in human B-lymphoblastoid cells. CYP2A6 coexpressed with human CYP reductase by a baculovirus expression system was also more active than CYP isoform 2E1 (CYP2E1) in the metabolism of MTBE, ETBE, and TAME. Kinetic studies on MTBE metabolism with human liver microsomes (n = 3) exhibited an apparent Michaelis constant (Km) of 28 to 89 uM and a maximum rate of metabolism (Vmax) of 215 to 783 pmol/min/mg. Metabolism of MTBE, ETBE, and TAME by human liver microsomes was inhibited by coumarin, a known substrate of human CYP2A6, in a concentration-dependent manner. Monoclonal antibody against human CYP2A6 caused a significant inhibition (75% to 95%) of the metabolism of MTBE, ETBE, and TAME in human liver microsomes. ...|For more Metabolism/Metabolites (Complete) data for Ethyl tert-butyl ether (9 total), please visit the HSDB record page.|Tert-butyl ethyl ether (ETBE) has known human metabolites that include tert-butanol.
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)
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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Fresh air, rest. Seek medical attention if you feel unwell.
First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again.
Rinse with plenty of water (remove contact lenses if easily possible).
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Esters and related compounds/|/SRP:/ 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. 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 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 ... . Treat frostbite by rapid rewarming ... . /Esters and related compounds/|/SRP:/ 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) or 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 ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/
/HUMAN EXPOSURE STUDIES/ ... Eight healthy male volunteers were exposed to ethyl tert-butyl ether (ETBE) vapor for 2 hr at four levels (0, 5, 25, and 50 ppm) during light physical exercise. The subjects rated irritative symptoms, discomfort, and central nervous system effects in a questionnaire. Ocular (eye redness, tear film break-up time, conjunctival epithelial damage, and blinking frequency), nasal (acoustic rhinometry and analysis of inflammatory markers and cells in nasal lavage fluid), and pulmonary (peak expiratory flow, forced expiratory volume in 1 s, forced vital capacity, vital capacity, and transfer factor) measurements were performed. Significantly increased ratings of solvent smell (p = 0.001, repeated-measures ANOVA) were seen during exposures and correlated to exposure levels. Furthermore, significantly elevated ratings of discomfort in throat and airways were seen during and after 50 ppm compared to the control exposure (p = 0.02). Increased nasal swelling (p = 0.001) and blinking frequency (p = 0.01) were noted at all exposure levels, but their magnitudes were not related to exposure levels. A slightly impaired pulmonary function was seen at 25 and 50 ppm, since forced vital capacity (p = 0.02) and vital capacity (p = 0.04) differed significantly from the clean air exposure. ...
2-ethoxy-2-methylpropane
The substance can be absorbed into the body by inhalation of its vapour and by ingestion.
Cough. Drowsiness. Unconsciousness.
Dry skin. Redness.
Redness. Pain.
Ethyl tert-butyl ether Use and Manufacturing
Ethyl tert-butyl ether (ETBE) can be manufactured from ethanol and isobutene.
Gasoline additive. tert-Butyl ethyl ether is synthesized from ethanol and isobutene and is used primarily as an oxygenate that is added to gasoline to improve the automobile exhaust quality by reducing the ozone and carbon monoxide emissions (HSDB, 2012). tert-Butyl ethyl ether has similar utility compared to another widely used oxygenate, methyl tertiary butyl ether (MTBE), and thus is a potential replacement for MTBE.Usage of ETBE as a fuel additive has halted in the United States, falling from 2 to 4 million barrels per month in 2005 to 0 barrels in 2006 (DOE, 2007). tert-Butyl ethyl ether continues to be used widely in Europe (EFOA, 2010). Since ETBE is used almost exclusively in fuels, contamination of groundwater as a result of spillage or leakage of the underground storage tanks is a major source of environmental release.
Fuels and fuel additives
Fuels and related products
1,000,000,000 - 5,000,000,000 lb|Propane, 2-ethoxy-2-methyl- is listed as a High Production Volume (HPV) chemical (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).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7616]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Propane, 2-ethoxy-2-methyl-. Aggregated National Production Volume: 500 million to < 1 billion pounds.
Petroleum lubricating oil and grease manufacturing|Propane, 2-ethoxy-2-methyl-: ACTIVE
Method: EPA-OGWDW/TSC 524.3; Procedure: gas chromatography/mass spectrometry; Analyte: ethyl tert-butyl ether; Matrix: finished drinking waters; Detection Limit: 0.01 ug/L.|Method: EPA-OSW 5030C; Procedure: purge-and-trap; Analyte: ethyl tert-butyl ether; Matrix: water; Detection Limit: not provided.|Method: USGS-NWQL O-4024-03; Procedure: gas chromatography/mass spectrometry; Analyte: ethyl tert-butyl ether; Matrix: whole-water; Detection Limit: 0.0524 ug/L.|Method: USGS-NWQL O-4127-96; Procedure: gas chromatography/mass spectrometry; Analyte: ethyl tert-butyl ether; Matrix: surface- or ground-water; Detection Limit: 0.06 ug/L.
Fire Hazards -> Flammable - 3rd degree
Computed Properties
Molecular Weight:102.17
XLogP3:1.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:102.104465066
Monoisotopic Mass:102.104465066
Topological Polar Surface Area:9.2
Heavy Atom Count:7
Complexity:42.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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