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Home > Encyclopedia > tert-Amyl methyl ether

tert-Amyl methyl ether

tert-Amyl methyl ether structure

tert-Amyl methyl ether 

structure
  • CAS No:

    994-05-8

  • Formula:

    C6H14O

  • Chemical Name:

    tert-Amyl methyl ether

  • Synonyms:

    Butane,2-methoxy-2-methyl-;Ether,methyl tert-pentyl;2-Methoxy-2-methylbutane;Methyl tert-pentyl ether;2-Methyl-2-methoxybutane;tert-Amyl methyl ether;1,1-Dimethylpropyl methyl ether;Methyl 1,1-dimethylpropyl ether;tert-Pentyl methyl ether;TAME (ether);TAME;Methyl tert-amyl ether;t-Amyl methyl ether

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

CLEAR COLOURLESS LIQUID


GasVapor; Liquid|COLOURLESS LIQUID.|Colorless liquid.

tert-Amyl methyl ether Basic Attributes

102.17500

102.17

213-611-4

94525J1AP8

1496

3271

DTXSID8024521|DTXSID20745704|DTXSID60745940

2909199090

Characteristics

9.23000

1.82140

GasVapor; Liquid

0.7703 g/cm3 @ Temp: 20 °C

-105.78°C (estimate)

86.3 °C

11 °F

n20/D 1.389(lit.)

12.35g/L(20 ºC)

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.

75.2 mm Hg at 25 deg C

Relative vapour density (air = 1): 3.6

LD50 orl-rat: 2100 mg/kg JJATDK 15,313,1995

Explosive limits , vol% in air: 1.1-7.1

5.50e-12 cm3/molecule*sec

0.00 atm-m3/mole|Henry's Law constant = 1.32X10-3 atm-cu m/mol at 25 °C

Hydroxyl radical reaction rate constant = 5.50X10-12 cu cm/molec-sec at 25 °C

415 °C|430 °C

The vapour is heavier than air.

Safety Information

II

3.1

UN 3271 3/PG 2

3

R11;R20/22;R36/38

S16-S26-S39-S45-S36/37

EK4421000

F,Xn,T

Fireproof.

Stable under recommended storage conditions.

P210-P260-P280-P301 + P310 + P330-P308 + P311-P403 + P233

H225-H301 + H311 + H331-H370

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

Organization for Economic Cooperation and Development; SIDS Initial Assessment Profile (SIAP) for 2-Methoxy-2-methylbutane (TAME) (994-005-8) (SIAM 21, October, 2005). This OECD Initial Assessment is part of a series of OECD SIDS documents published by UNEP Chemicals to facilitate the access to information needed for health and environmental risk assessments of chemicals.[Available from, as of September 28, 2010: http://webnet.oecd.org/Hpv/ui/SponsoredSubstances.aspx]|European Commission, ESIS; IUCLID Dataset, 2-Methoxy-2-methylbutane (994-05-8) (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 28, 2010: http://esis.jrc.ec.europa.eu/]

Extremely flammable. Vapour/air mixtures are explosive.|Flammable - 4th degree

|Danger|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P303+P361+P353, P304+P340, P312, P330, P370+P378, P403+P233, P403+P235, P405, and P501|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|Aggregated GHS information provided by 78 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P312, P321, P337+P313, P370+P378, P403+P233, P403+P235, P405, and P501

Protective gloves, safety spectacles

Highly flammable

Lower explosive limit: 1.1%-vol; Upper explosive limit: 7.1%-vol|Vapor/air mixtures are explosive.|Explosive limits , vol% in air: 1.1-7.1

Foam, alcohol-resistant foam, dry powder, carbon dioxide ... Keep drums, etc., cool by spraying with water.|Wear self contained breathing apparatus for fire fighting if necessary.

Ventilation. Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Personal protection: filter respirator for organic gases and vapors.

Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.

TAME is not irritating to skin or eyes or sensitizing.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer. Do NOT let this chemical enter the environment.

Fireproof.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis. Exposure at high levels could cause lowering of consciousness.

The substance defats the skin, which may cause dryness or cracking.

NO open flames, NO sparks and NO smoking.

Use ventilation, local exhaust or breathing protection.

Protective gloves.

Wear safety spectacles.

tert-Amyl methyl ether was detected in 3.1% of 249 storm water samples collected from 46 different sampling locations in North Carolina from November 1998 through October 1999. The mean and maximum concentrations were 0.09 and 0.23 ug/L, respectively. Samples were collected from urban land-use areas where fuel oxygenates might have been expected to occur(1).

Toxicity

Human Health. tert-amyl methyl ether (TAME) is absorbed efficiently from the rat intestine. TAME is rapidly absorbed from lungs; the respiration net uptake is 40 %. Studies with tert-methyl butyl ether (MTBE) suggest one third or less of a dermal TAME dose is absorbed. In rats, TAME is distributed evenly in the body. Urine is the main route of elimination. Based on human volunteer studies, the half-lives in blood varied between 1.2 and 6.3 hours. The main urine metabolites are 2-methyl-2,3- butanediol, 2-hydroxy-2-methylbutyric acid and 3-hydroxy-3-methylbutyric acid. Free and conjugated TAA (tert-amyl alcohol) and TAME were only minor metabolites in urine. The acute toxicity of TAME is not high. The LC50 value via inhalation is over 5.3 mg/l. The predicted oral LD50 was for females 1602 mg/kg, males 2417 mg/kg and combined 2152 mg/kg. Although no dermal studies were available, toxicity via skin is not likely to be higher than via oral route. TAME is not irritating to skin or eyes or sensitizing. The toxicity caused by TAME in repeated exposures is not severe. A NOAEC of 250 ppm (1060 mg/cu m) is selected for respiratory exposure based on the organ weight increases of liver, adrenals and kidneys seen in a 90 day study in F-344 rat with both sexes. Via oral route, a LOAEL of 125 mg/kg was established based on the adrenal weight increase in the male rats. TAME did not cause point mutations in bacterial assays or in Chinese hamster ovary cell. In Chinese hamster ovary cells in vitro, TAME caused a clear dose-related increase of chromosome aberrations, which increased when metabolic activation was present. However, a micronucleus study conducted in mice was negative at all sampling times. In the light of present data, TAME cannot be considered mutagenic. No reliable carcinogenicity studies were available In a 2-generation reproductive study, TAME was not toxic to reproduction in rat (NOAEC of 3000 ppm (12720 mg/cu m). In the same study, NOAEC of 250 ppm was found for offspring toxicity and for adult systemic toxicity. In a developmental toxicity study with rats, the only noted effect was foetal weight reduction at 3500 ppm. From a developmental toxicity study with mice, a NOAEC of 250 ppm (1063 mg/cu m) was selected for developmental effects based on malformations (cleft palate) seen at 1500 ppm and 3500 ppm. It is plausible that cleft palates are a secondary effect related to anesthesia and/or maternal stress. Taking into consideration that the cleft palates were seen only at very high TAME concentrations, and because there were no adverse developmental effects seen in rats, the effect noted in mice is not likely to be of consequence to humans. Environment. TAME is a volatile (vp. 90 hPa at 20 o C) liquid which is hydrolytically stable and moderately soluble in water (11 g/L at 20 oC). Static equilibrium partitioning between environmental compartments at 20 oC is as follows: air 95.6, water 4.25, sediment 0.001 and soil 0.038 (EQC ver1.1). TAME is very mobile in soil and may easily leach to groundwater (transported with water). TAME is easily volatilized into the atmosphere from top soil and surface water. Photodegradation in the atmosphere is the primary route of removal in the environment and degradation half-life is ca. 3 to 5 days. Biodegradation in soil, sediment, surface- and groundwater is very slow and TAME may be regarded persistent in these compartments. However, in industrial waste water sewage treatment plants having continuous TAME exposure, adapted microbial population capable of effectively degrading TAME may exist. It is unlikely that TAME would bioconcentrate in high extent or would accumulate in biota for long time periods. The measured log Kow is 1.55 and the calculated BCF in fish is 4. The lowest valid aquatic acute and (one) chronic toxicity test results for fish, daphnids, algae and bacteria are below. Terrestrial toxicity results are not available. (1): Oncorhynchus mykiss: 96 hr-LC50 = 580 mg/L (2): Daphnia magna: 48 hr-EC50 = 100 mg/L and Americamysis bahia: 96 hr-LC50 = 14 mg/L, 28-day NOEC = 3.4 mg/L (3): Pseudokirchneriella subcapitata: 72 hr-EbC50 = 230 mg/L; 72 hr-ErC50 = 780 mg/L; 72 hr-NOEC = 77 mg/L (4): Pseudomonas putida, cell multiplication inhibition test: 16 hr-EC10 = 25 mg/L; 16 hr-EC50 580 mg/L The aquatic PNEC is 0.068 mg/L based on the Americamysis bahia chronic test result (AF=50) and the PNEC for intermittent release is 1.4 mg/L (AF=10). The PNEC for micro-organism is 25 mg/L (AF=1). The terrestrial PNEC is 0.035 mg/kg wwt calculated from the aquatic PNEC using the equilibrium partitioning method.

LD50 Rat oral ca. 2.1 g/kg|LD50 Rat oral 2100 mg/kg|LD50 Rat oral 1602 mg/kg|LC50 Rat inhalation >5,400 mg/cu m /4 hr

tert-Amyl methyl ether's production and use as a gasoline additive as an octane booster(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 19-160(2), indicates that tert-amyl methyl ether is expected to have very high to moderate mobility in soil(SRC). Volatilization of tert-amyl methyl ether from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.32X10-3 atm-cu m/mole(3). tert-Amyl methyl ether is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 75.2 mm Hg at 25 °C(4). tert-Amyl methyl ether did not pass the ready biodegradability test of 60% in 28 days using the Closed Bottle test(5), suggesting that biodegradation is not an important environmental fate process in soil(SRC, 2010).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 19 to 160(2), indicates that tert-amyl methyl ether is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is(3) based upon a Henry's Law constant of 1.32X10-3 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 4 hours and 4 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 5(SRC), from its log Kow of 1.55(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). tert-Amyl methyl ether did not pass the ready biodegradability test of 60% in 28 days using the Closed Bottle test(8), 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), tert-amyl methyl ether, which has a vapor pressure of 75.2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase tert-amyl methyl 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 3 days(SRC), calculated from its rate constant of 5.50X10-12 cu cm/molecule-sec at 25 °C(3). tert-Amyl methyl 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 tert-amyl methyl ether with photochemically-produced hydroxyl radicals is 5.50X10-12 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of tert-amyl methyl ether with photochemically-produced nitrate radicals is 1.218X10-12 cu cm/molecule-sec at 257-367 K. Degradation products identified were tert-amyl formate, formaldehyde, and tert-amyl nitrate(2). tert-Amyl methyl ether is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). tert-Amyl methyl 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 5 was calculated in fish for tert-amyl methyl ether(SRC), using a log Kow of 1.55(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).

The Koc of tert-amyl methyl ether has been reported to range from 19 to 160(1,2). According to a classification scheme(3), these Koc values suggest that tert-amyl methyl ether is expected to have very high to moderate mobility in soil. Using a model system simulating horizontal ground water flow in the saturated zone, consisting of only soil and water phases (an unconfined sand aquifer was selected as an example case), a Koc of 60 was calculated(4).

The Henry's Law constant for tert-amyl methyl ether is 1.32X10-3 atm-cu m/mole(1). This Henry's Law constant indicates that tert-amyl methyl 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 4 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). tert-Amyl methyl ether's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). tert-Amyl methyl ether is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 75.2 mm Hg(3).

GROUNDWATER: tert-Amyl methyl ether was detected at an average concentration of 0.05 ug/L (median 0.4 ug/L) in contaminated groundwater samples collected from Dusseldorf, Germany in June, 2003; detection limit of 0.013 ug/L(1). The compound exhibited a 18.3% 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): 0.38 minimum; 12,000 maximum; 240 mean(2).|DRINKING WATER: The U.S. Geological Survey surveyed 1,206 well samples in 2006; tert-amyl methyl ether was detected in 6 samples, detection frequency 0.50%(1). tert-Amyl methylether was detected (range of 0.4-0.7 ug/L) in 1.4% of 579 groundwater sources and 375 surface-water sources, randomly collected from May 3, 1999 through October 200 from throughout the US, Native American lands, and Puerto Rico(2).

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use for tert-amyl methyll ether is 1000 or greater; the data may be greatly underestimated(1).|Occupational exposure to tert-amyl methyl ether may occur through inhalationand dermal contact with this compound at workplaces where tert-amyl methyl ether is produced or used. On average, gasoline road-tanker drivers in Finland are exposed to tert-amyl methyl ether vapors at a mean concentration of 0.3 mg/cu m during a three-hour shift(1). Limited and use monitoring data indicate that the general population may be exposed to tert-amyl methyl ether via inhalation of ambient air and ingestion of drinking water(SRC).

On average, levels of tert-amyl methyl ether in urine samples from Finnish gasoline road-tanker drivers after a work shift and 16 hours later were reported to be 16 and 9 nmol/L, respectively(1). Breathing zone concentrations among Finnish gasoline lorry drivers were reported at a geometric mean of 0.98 mg/cu m, range of 0.22 to 6.9 mg/cu m; study conducted in August, 1995. Concentrations in blood and urine were 79 to 151 and 7 to 40 nmol/L, respectively(2).

Drug Information

Healthy male volunteers were exposed via inhalation to gasoline oxygenates methyl tert-butyl ether (MTBE) or tert-amyl methyl ether (TAME). The 4-hr exposures were carried out in a dynamic chamber at 25 and 75 ppm for MTBE and at 15 and 50 ppm for TAME. The overall mean pulmonary retention of MTBE was 43 +/- 2.6%; the corresponding mean for TAME was 51 +/- 3.9%. Approximately 52% of the absorbed dose of MTBE was exhaled within 44 hr following the exposure; for TAME, the corresponding figure was 30%. MTBE and TAME in blood and exhaled air reached their highest concentrations at the end of exposure, whereas the concentrations of the metabolites tert-butanol (TBA) and tert-amyl alcohol (TAA) concentrations were highest 0.5-1 hr after the exposure and then declined slowly. Two consecutive half-times were observed for the disappearance of MTBE and TAME from blood and exhaled air. The half-times for MTBE in blood were about 1.7 and 3.8 hr and those for TAME 1.2 and 4.9 hr. For TAA, a single half-time of about 6 hr best described the disappearance from blood and exhaled air; for TBA, the disappearance was slow and seemed to follow zero-order kinetics for 24 hr. In urine, maximal concentrations of MTBE and TAME were observed toward the end of exposure or slightly (< or = 1 hr) after the exposure and showed half-times of about 4 hr and 8 hr, respectively. Urinary concentrations of TAA followed first-order kinetics with a half-time of about 8 hr, whereas the disappearance of TBA was slower and showed zero-order kinetics at concentrations above approx. 10 umol/L. Approximately 0.2% of the inhaled dose of MTBE and 0.1% of the dose of TAME was excreted unchanged in urine, whereas the urinary excretion of free TBA and TAA was 1.2% and 0.3% within 48 hr. The blood/air and oil/blood partition coefficients, determined in vitro, were 20 and 14 for MTBE and 20 and 37 for TAME. By intrapolation from the two experimental exposure concentrations, biomonitoring action limits corresponding to an 8-hr time-weighted average (TWA) exposure of 50 ppm was estimated to be 20 umol/L for post-shift urinary MTBE, 1 umol/L for exhaled air MTBE in a post-shift sample, and 30 umol/L for urinary TBA in a next-morning specimen. For TAME and TAA, concentrations corresponding to an 8-hr TWA exposure at 20 ppm were estimated to be 6 umol/L (TAME in post-shift urine), 0.2 umol/L (TAME in post-shift exhaled air), and 3 umol/L (TAA in next morning urine).|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. ...|Tert-amyl methyl ether (TAME) is absorbed efficiently from the rat intestine. TAME is rapidly absorbed from lungs; the respiration net uptake is 40 %. Studies with tert-methyl butyl ether (MTBE) suggest one third or less of a dermal TAME dose is absorbed. In rats, TAME is distributed evenly in the body. Urine is the main route of elimination.|The effect of dose level, duration of exposure and route of administration on the metabolism and distribution of tert-amyl methyl ether (TAME) were investigated in male and female F344 rats and CD-1 mice following inhalation or gavage administration. By 48 hr after exposure, >96% of the administered radioactivity was expired in air (16-71%) or eliminated in urine and feces (28-72%). Following inhalation exposure, mice had a two- to threefold greater relative uptake of [14C]TAME compared with rats. Metabolites were excreted in urine of rats and mice that are formed by glucuronide conjugation of tertiary amyl alcohol (TAA), oxidation of TAA to 2,3-dihydroxy-2-methylbutane and glucuronide conjugation of 2,3-dihydroxy-2-methylbutane. A saturation in the uptake and metabolism of TAME with increased exposure concentration was indicated by a decreased relative uptake of total [14C]TAME equivalents and an increase in the percentage expired as volatiles. A saturation of P-450 oxidation of TAA was indicated by a disproportional decrease of 2,3-dihydroxy-2-methylbutane and its glucuronide conjugate with increased exposure concentration.|For more Absorption, Distribution and Excretion (Complete) data for Tert-amyl methyl ether (8 total), please visit the HSDB record page.

The biotransformation of tert-amyl methyl ether (TAME) in rats and one human volunteer after inhalation of (12)C- or (13)C-labeled TAME /was studied/. In addition, the biotransformation of [(13)C]-tert-amyl alcohol was studied in rats after gavage. Urinary metabolites were identified by GC/MS and (13)C NMR. Rats (two males and two females) were individually exposed to 2000 ppm ((12)C or (13)C-TAME for 6 hr, and urine was collected for 48 hr. Free and glucuronidated 2-methyl-2,3-butanediol and a glucuronide of tert-amyl alcohol were identified by (13)C NMR, GC/MS, and LC/MS/MS as major urinary metabolites on the basis of the relative intensities of the (13)C NMR signals. The presence of several minor metabolites was also indicated by (13)C NMR; they were identified as tert-amyl alcohol, 2-hydroxy-2-methylbutyric acid, and 3-hydroxy-3-methylbutyric acid. One human volunteer was exposed to an initial concentration of 27,000 ppm (13)C-TAME by inhalation for 4 min from a 2 L gas sampling bag, and metabolites of TAME excreted in urine were analyzed by (13)C NMR. All TAME metabolites identified in rats were also present in the human urine samples. To study tert-amyl alcohol biotransformation, male rats (n = 3) were treated with 250 mg/kg (13)C-tert-amyl alcohol dissolved in corn oil by gavage, and urine was collected for 48 hr. (13)C NMR of the urine samples showed the presence of metabolites identical to those in the urine of (13)CTAME-treated 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. ...|The main urine metabolites are 2-methyl-2,3- butanediol, 2-hydroxy-2-methylbutyric acid and 3-hydroxy-3-methylbutyric acid. Free and conjugated TAA (tert-amyl alcohol) and tert-amyl methyl ether (TAME) were only minor metabolites in urine.|The purpose of this study was to investigate the blood pharmacokinetics of the oxygenate tertiary amyl methyl ether (TAME), its major metabolite tertiary amyl alcohol (TAA) and acetone in rats and mice following inhalation exposure to TAME. Species differences in the area under the curve (AUC) for TAME were significant at each exposure concentration. For rats, the blood TAME AUC increased in proportion with an increase in exposure concentration. For mice, an increase in exposure concentration (100-500 ppm) resulted in a disproportional increase in the TAME AUC. Mice had greater (two- to threefold) blood concentrations of TAA compared with rats following exposure to 2500 or 500 ppm TAME. Mice had a disproportional increase in the TAA AUC with an increase in exposure concentration (100-500 ppm). This difference could result from saturation of a process (e.g. oxidation, glucuronide conjugation) that is involved in the further metabolism of TAA. For each species, gender and exposure concentration, acetone increased during exposure and returned to control values by 16 h following exposure. ...|For more Metabolism/Metabolites (Complete) data for Tert-amyl methyl ether (8 total), please visit the HSDB record page.|Tert-amyl methyl ether has known human metabolites that include tert-amyl alcohol.

Based on human volunteer studies, the half-lives in blood varied between 1.2 and 6.3 hr.

Fresh air, rest.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

/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/

/SIGNS AND SYMPTOMS/ Effects of short-term exposure: If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis. Exposure at high levels could cause lowering of consciousness. Effects of long-term exposure: The liquid defats the skin.

2-methoxy-2-methylbutane

The substance can be absorbed into the body by inhalation and by ingestion.

Dizziness. Drowsiness. Weakness.


Dry skin.

tert-Amyl methyl ether Use and Manufacturing

Methods of Manufacturing

TAME /tert-amyl methyl ether/ is produced from compounds already present in the gasoline and characterized by the highest octane rating in the C5 fractions ...|Methyl tert-amyl ether (TAME), /is/ made by a catalytic process from methanol (qv) and the corresponding isomeric olefin.

Uses

Fuel additive for gasoline.


Fuels and fuel additives


Fuels and related products

Production

500,000,000 - 750,000,000 lb|Butane, 2-methoxy-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#7619]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Butane, 2-methoxy-2-methyl-. Aggregated National Production Volume: 1 billion pounds and greater.

Petroleum lubricating oil and grease manufacturing|Butane, 2-methoxy-2-methyl-: ACTIVE|PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Method: EPA-OGWDW/TSC 524.3; Procedure: gas chromatography/mass spectrometry; Analyte: tert-amy methyl ether; Matrix: finished drinking waters; Detection Limit: 0.017 ug/L.|Method: EPA-OSW 5030C; Procedure: purge-and-trap; Analyte: tert-amyl methyl ether; Matrix: water; Detection Limit: not provided.|Method: USGS-NWQL O-4024-03; Procedure: gas chromatography/mass spectrometry; Analyte: tert-amyl methyl ether; Matrix: whole-water; Detection Limit: 0.035 ug/L.|Method: USGS-NWQL O-4127-96; Procedure: gas chromatography/mass spectrometry; Analyte: tert-amyl methyl ether; Matrix: surface- or ground-water; Detection Limit: 0.06 ug/L.

Fire Hazards -> Flammable - 4th degree

Computed Properties

Molecular Weight:102.17
XLogP3:1.6
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:48.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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