기본 정보
- 표준 SMILES
CCOC(C)(C)C- InChIKey
NUMQCACRALPSHD-UHFFFAOYSA-N- 분자식
- C6H14O
- 평균 분자량
- 102.17 g/mol
- 단동위원소 질량
- 102.10446507
이름 및 식별자
- 우선 이름
- Ethyl tert-butyl ether
- IUPAC
- 2-ethoxy-2-methylpropane
- 현지명
- 삼차뷰틸 에틸 에테르
- 영어명
- tert-Butyl ethyl ether
- 분자식
- C6H14O
- 분자량
- 102.17
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
637-92-3- PubChem CID
- 12512
- DTXSID
DTXSID0025604- ChEMBL
CHEMBL1409831- ChEBI
CHEBI:141564- UNII
- 3R9B16WR19
- EC Number
- 211-309-7
- Nikkaji
- J45.669A
물성
구조 계산 물성
- XLogP
- 1.4
- 극성 표면적
- 9.2 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 1
- 회전 가능 결합 수
- 2
- 무거운 원자 수
- 7
- 형식 전하
- 0
- 복잡도
- 42
실험 및 물리화학적 성질
Density
0.7519 at 77 °F (NTP, 1992) - Less dense than water; will float
0.736 g/cu cm at 25 °C
Relative density (water = 1): 0.75
0.7519
Solubility
less than 1 mg/mL at 70 °F (NTP, 1992)
Very soluble in ethanol, ethyl ether
In water, 1.2X10+4 mg/L at 20 °C
Solubility in water, g/100ml at 25 °C: 1.2 (poor)
Flash Point
-3 °F (NTP, 1992)
-19 °C (-2 °F) - closed cup
-19 °C c.c.
-3 °F
Boiling Point
163.6 °F at 760 mmHg (NTP, 1992)
72.6 °C
70-73 °C
163.6 °F
Melting Point
-137 °F (NTP, 1992)
-94 °C
-94 °C
-137 °F
Vapor Pressure
10 mmHg at 77 °F ; 185 mmHg at 122 °F; 447 mmHg at 158 °F (NTP, 1992)
124.0 [mmHg]
124 mm Hg at 25 °C (extrapolated)
Vapor pressure, kPa at 20 °C: 12.8
10 mmHg
물리화학적 성질
- 녹는점
- 97 °C · −97 °C(lit.)
- 끓는 점
- 72 · 72-73 °C(lit.)
- 밀도
- 0.742 g/mL · 0.742 g/mL at 25 °C(lit.)
- 증기압
- 155 mm · 155 mm Hg ( 25 °C)
- 굴절률
- 20 · n20/D 1.375(lit.)
- 인화점
- -19 °C · -19 °C
- 저장 조건
- 30 °C · Store below +30°C.
- 용해도
- 20 °C에서 · 물: 20°C에서 용해성1.2g/100g(lit.)
- 물리적 상태
- 분말/고체
- 색상
- 하얀색
- 폭발한계
- 1.23 · 1.23-7.7%(V)
- 수용성
- 알코올, 에틸에테르와 혼합 가능. 물과 약간 섞임.
- Merck
- 14 · 14,3774
- BRN
- 1731469 · 1731469
- Henry's Law Constant
- 7.2 · 7.2×10-3 mol/(m3Pa) at 25℃, Brockbank (2013)
- 안정성
- 안정적이지만 공기와 반응하여 과산화물을 형성할 수 있습니다. 개봉한 후에는 불활성 대기에 보관하고 사용하기 전에 과산화물이 있는지 테스트하십시오. 가연성이 높습니다. 강한 산화제와 호환되지 않습니다.
- 주요 응용
- 환경
- InChI
- 1S/C6H14O/c1-5-7-6(2,3)4/h5H2,1-4H3
- InChIKey
- NUMQCACRALPSHD-UHFFFAOYSA-N
- SMILES
- CCOC(C)(C)C
- 표면장력
- 19.73 mN/m · 19.73mN/m at 298.15K
- EPA
- Ethyl tert-butyl ether (637-92-3)
화학적 성질
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.
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 2% (3 of 151) of reports.
Danger
H224 (14.6%): Extremely flammable liquid and vapor [Danger Flammable liquids];H225 (83.4%): Highly Flammable liquid and vapor [Danger Flammable liquids];H315 (28.5%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (29.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (17.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H336 (77.5%): May cause drowsiness or dizziness [Warning Specific target organ toxicity, single exposure; Narcotic effects]
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 151 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 3 of 151 reports by companies.;There are 16 notifications provided by 148 of 151 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
유해성 정보
Regulatory Information
Chemical: Propane, 2-ethoxy-2-methyl-;Specific Information Requirement: Obligations to provide information apply. You must tell us within 28 days if the circumstances of your importation or manufacture (introduction) are different to those in our assessment.
Hazard Traits - Carcinogenicity; Reproductive Toxicity;Authoritative List - CWA 303(c); IARC Carcinogens - 2B;Report - regardless of intended function of ingredient in the product
Regulation (EC) No 178/2002 (amended)
Propane, 2-ethoxy-2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propane, 2-ethoxy-2-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 21-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15520
Ethyl tert-butyl ether: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Fire Hazards
This chemical is flammable. (NTP, 1992)
Highly flammable. Vapour/air mixtures are explosive.
Health Hazards
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 asphyxiation, especially when in closed or confined areas. Runoff from fire control or dilution water may cause environmental contamination. (ERG, 2024)
Hazards Summary
At lethal concentrations, exposed animals experience general anesthetic effects. [ChemIDplus] A skin and eye irritant; NOAEL = 500 ppm for CNS effects in rats; In 90 day inhalation studies of rats, causes liver changes (5000 ppm) and degenerative changes of spermatocytes in seminiferous tubules (1750-5000 ppm); [ACGIH]
Special Reports
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/]
TSCA Requirements
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Ethyl-tert-butyl ether is included on this list. Effective date: 12/28/94; Sunset date: 6/30/98.
Reactivity Profile
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.
안전 및 보호
Fire Fighting
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Use powder, alcohol-resistant foam, water in large amounts, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
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).
Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.
First Aid
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)
Fire Fighting Procedures
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.
Cleanup Methods
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.
Nonfire Spill Response
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)
Disposal Methods
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.
Spillage Disposal
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.
Preventive Measures
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.
Isolation and Evacuation
Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:;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 tank car or highway tank 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, 2024)
독성 정보
Environmental Fate
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).
Adverse Effects
Neurotoxin - Acute solvent syndrome;Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.;ACGIH Carcinogen - Not Classifiable.
Signs and Symptoms
Cough. Drowsiness. Unconsciousness.
Dry skin. Redness.
Redness. Pain.
Sore throat. Aspiration hazard! Further see Inhalation.
Effluent Concentrations
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).
EPA IRIS Information
Ethyl Tertiary Butyl Ether (ETBE)
Hepatic
Urinary
Human Toxicity Excerpts
/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. ...
Artificial Pollution Sources
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).
규제 정보
Regulatory Information
Chemical: Propane, 2-ethoxy-2-methyl-;Specific Information Requirement: Obligations to provide information apply. You must tell us within 28 days if the circumstances of your importation or manufacture (introduction) are different to those in our assessment.
Hazard Traits - Carcinogenicity; Reproductive Toxicity;Authoritative List - CWA 303(c); IARC Carcinogens - 2B;Report - regardless of intended function of ingredient in the product
Regulation (EC) No 178/2002 (amended)
Propane, 2-ethoxy-2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propane, 2-ethoxy-2-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 21-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15520
Ethyl tert-butyl ether: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
TSCA Requirements
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Ethyl-tert-butyl ether is included on this list. Effective date: 12/28/94; Sunset date: 6/30/98.
안전 데이터
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- KN4730200
- ridadr
- UN 1179 3/PG 2
- HS 번호
- 29091990
- risk_code
- 11-36/38-67
- hazard_code
- F,Xi
- safety_code
- 16-26
- 포장분류
- II
- 위험 등급
- 3
- 기존화학 물질
- KE-13450
- F 고인화성물질
- 23
- Hazard Classifications
- Flam. Liq. 2STOT SE 3
- 스토리지 클래스
- 3 - Flammable liquids
- 유해 물질 데이터
- 637-92-3(Hazardous Substances Data)
화학 및 산업
약리 정보
Metabolism/Metabolites
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
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.
Absorption, Distribution and Excretion
... 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 d
... 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.
용도 및 제조
Uses
An alternative gasoline additive to decrease carbon monoxide emissions; [ACGIH]
Gasoline additive
U.S. Production
2023: 1,000,000,000 - <5,000,000,000 lb;2022: 2,500,000,000 - <4,000,000,000 lb;2021: 1,000,000,000 - <5,000,000,000 lb;2020: 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#7604]
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.
General Manufacturing Information
Wholesale and Retail Trade;Petrochemical Manufacturing;Petroleum Refineries;All other Petroleum and Coal Products Manufacturing
Propane, 2-ethoxy-2-methyl-: ACTIVE
응용 분야
역사In the 1990s, the production of other fuel oxygenates began, with the appearance of ethyl tertiary-butyl ether, CAS RN 637- 92-3 (ETBE), first produced in France in 1992, and tertiary-amyl methyl ether, CAS RN 994-05-8 (TAME). To their number others have been added, such as diisopropyl ether, CAS RN 108-20-3 (DIPE) and, most recently, tertiary-amyl ethyl ether, CAS RN 919-94-8 (TAEE), which is being produced in Germany; however, the use of these oxygenates is currently small scale. Alcohols, such as ethanol, CAS RN 64-17-5 (EtOH) and methanol, may also be used as fuel oxygenates, but methanol is not used as such, although it is used in China as a liquid fuel for passenger cars and for synthesis of dimethyl ether as an alternative to diesel fuel for trucks and buses. Ethers have the advantage over alcohols in currently designed engines because alcohols in petrol tend to make the blend very volatile and water soluble, possibly creating problems in the fueldistribution system and vehicle engine. Perhaps the larger-scale use of ethanol in fuel oxygenation is in the production of ETBE or coblending with ETBE.
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