甲基叔丁基醚

tert-Butyl methyl ether

HCID 15413CAS 1634-04-4

基本信息

标准SMILES
COC(C)(C)C
InChIKey
BZLVMXJERCGZMT-UHFFFAOYSA-N
分子式
C5H12O
平均分子量
88.15 g/mol
单同位素质量
88.088815

概述

Methyl tert-butyl ether (MTBE) is a flammable liquid with a distinctive, disagreeable odor. It is made from blending chemicals such as isobutylene and methanol, and has been used since the 1980s as an additive for unleaded gasolines to achieve more efficient burning.MTBE is also used to dissolve gallstones. Patients treated in this way have MTBE delivered directly to their gall bladders through special tubes that are surgically inserted.

名称与标识

首选名称
tert-Butyl methyl ether
IUPAC
2-methoxy-2-methylpropane
中文名
甲基叔丁基醚
英文名
tert-Butyl methyl ether
分子式
C5H12O
分子量
88.15

名称与别名

tert-Butyl methyl etherMethyl tert-butyl ether1634-04-42-Methoxy-2-methylpropaneMTBEMethyl t-butyl etherPropane, 2-methoxy-2-methyl-T-BUTYL METHYL ETHER2-Methyl-2-methoxypropaneMethyl tertiary-butyl etherEther, tert-butyl methylMethyl 1,1-dimethylethyl ether
展开更多名称
甲叔醚甲基叔丁醚叔丁基甲酯叔丁基甲醚叔丁基甲基醚甲基特丁基醚甲基異丁基醚甲基叔丁基醚甲基叔丁基谜甲基三級丁基醚TBMEMTBBOC-ARG(MTR)-OHMethyl tert-butyl ether, for residue analysis2-methoxy-2-methyl-PropaneMETHYL-T-BUTYL ETHER
1,1-dimethylethyl methyl etherDTXSID3020833CHEBI:2764229I4YB3S89TERT-BUTOXYMETHANEDTXCID30833methyl tert-butyl ether (mtbe)RefChem:818082

数据库标识

CAS
1634-04-4
PubChem CID
15413
DTXSID
DTXSID3020833
ChEMBL
CHEMBL1452799
ChEBI
CHEBI:27642
UNII
29I4YB3S89
EC Number
216-653-1
Nikkaji
J27.142J

性质

结构计算性质

XLogP
0.9
极性表面积
9.2 Ų
氢键供体
0
氢键受体
1
可旋转键
1
重原子
6

实验与物化性质

Chemical Classes · 3 条

Hazardous Air Pollutants (HAPs)

Flammable agents - 3rd degree

Volatile Organic Compound (VOC)

SolventsSolvents -> Ethers (<C12)
SpringerMaterials PropertiesSchoenflies notation
PesticidesPesticide -> EPA IRIS
LogP · 2 条

log Kow = 0.94

1.06

OdorTerpene-like odor

物理化学性质

熔点
-110 °C · -110 °C
沸点
55 · 55-56 °C(lit.)
密度
0.7404 · 0.7404
蒸气密度
3.1 · 3.1 (vs air)
蒸气压
4.05 psi · 4.05 psi ( 20 °C)
折射率
20 · n20/D 1.369(lit.)

化学性质

无色、低粘度液体,具有类似萜烯的臭味。微溶于水。与许多有机溶剂和汽油互溶。与一些极性溶剂如水、甲醇、乙醇等形成共沸物。有轻度麻醉作用。

安全与法规

GHS分类

GHS Classification · 6 条

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P264, P280, P302+P352, P303+P361+P353, P321, P332+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P264, P280, P302+P352, P303+P361+P353, P321, P332+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

危害信息

Regulatory Information · 6 条

Chemical: Propane, 2-methoxy-2-methyl-

Hazard Traits - Carcinogenicity; Dermatotoxicity; Hepatotoxicity and Digestive System Toxicity; Nephrotoxicity and Other Toxicity to the Urinary System; Neurotoxicity; Ocular Toxicity

Regulation (EC) No 178/2002 (amended)

Propane, 2-methoxy-2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propane, 2-methoxy-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: 18-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15543

Methyl t-butyl ether: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Propane, 2-methoxy-2-methyl-: Human health tier II assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 条

Special Hazards of Combustion Products: May contain irritating and toxic gases.

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Vapour/air mixtures are explosive.

Fire PotentialFlammable when exposed to heat or flame.
Health Hazards · 2 条

INHALATION: May cause dizziness or suffocation. Contact may irritate or burn eyes or skin. May be harmful if swallowed. (USCG, 1999)

· Inhalation or contact with material may irritate or burn skin and eyes.

安全与防护

Fire Fighting · 2 条

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

Use powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 条

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

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.

Rinse mouth. Give a slurry of activated charcoal in water to drink. Do NOT induce vomiting. Refer for medical attention .

Accidental Release Measures · 2 条

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 条

INHALATION: Move victim to fresh air; call emergency medical care. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.

General First Aid:

Safe StorageFireproof. Separated from strong oxidants and strong acids.
Firefighting HazardsHazardous decomposition products formed under fire conditions - Carbon oxides

毒理信息

Toxicological InformationCDC-ATSDR Toxicological Profile
Body Burden · 2 条

In Stamford, CT in 1993, venous blood samples were collected from 14 commuters and from 30 other persons who worked in the vicinity of traffic or automobiles(1). The highest levels of methyl t-butyl ether were measured among gasoline service station attendants, range 7.6 to 28.9 ug/L, median 15 ug/L; blood levels of methyl t-butyl ether among persons who worked in car repair shops ranged from 0.17 to 36.7 ug/L, median 1.73 ug/L(1). Concentrations of methyl t-butyl ether in the blood of commuters were generally the lowest, range <0.05 to 2.60 ug/L, median 0.11 ug/L(1). Blood levels of methyl t-butyl ether correlated strongly with personal-breathing-zone samples(1). In Fairbanks, AK, during an oxygenated fuel program in Dec 1992, 18 workers exposed to motor vehicle exhaust or gasoline fumes had a median post-shift methyl t-butyl ether blood concentration of 1.8 ug/L, range 0.2 to 37.0 ug/L; in Feb 1993 after the oxygenated fuel program had been suspended, the median post-shift methyl t-butyl ether blood concentration in 28 workers exposed to motor vehicle exhaust or gasoline fumes was 0.24 ug/L, range 0.05 to 1.44 ug/L(2). Alveolar breath samples contained methyl t-butyl ether at concentrations ranging from 7.76 to 9.58 ug/cu m(3).

On average, levels of methyl t-butyl ether in urine samples from Finnish gasoline road-tanker drivers after a work shift and 16 hours later were reported to be 113 and 18 nmol/L, respectively(1). Breathing zone concentrations among Finnish gasoline lorry drivers were reported at a geometric mean of 4.3 (October 1994) and 6.4 mg/cu m (August 1995). Concentrations in blood were 143 and 213 nmol/L, for October and August, respectively; levels in urine ranged from <5 to 401 nmol/L and 30 to 253 nmol/L 3 and 23 hours post exposure in October, respectively; 17 to 488 nmol/L and <5 to 562 nmol/L 3 and 23 hours post exposure in August, respectively(2). According to the 1999-2000 US National Health and Nutrition Examination Survey (NHANES) methyl t-butyl ether was detected in 26.3% of 354 personal air samples and in 98.6% of 276 blood samples from 851 persons aged 20-59 years(3).

Target Organs · 2 条

Gastrointestinal (Stomach and Intestines, part of the digestive system), Hepatic (Liver), Neurological (Nervous System), Renal (Urinary System or Kidneys), Respiratory (From the Nose to the Lungs)

Hepatic

Ecotoxicity Values · 2 条

LC50; Species: Nitocra spinipes (Harpacticoid copepod); Conditions: saltwater, static, salinity 7 ppt; Concentration: >1000000 ug/L for 96 hr /formulation/

LC50; Species: Alburnus alburnus (Bleak); Conditions: saltwater, static, salinity 7 ppt; Concentration: >1000000 ug/L for 96 hr /formulation/

Environmental Fate · 3 条

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 11-12(2,3) indicates that methyl t-butyl ether is expected to have very high mobility in soil(SRC). Volatilization of methyl t-butyl ether from moist soil is expected to be an important fate process(SRC) given a Henry's Law constant of 5.87X10-4 atm-cu m/mole(4). Methyl t-butyl ether is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 250 mm Hg at 25 °C(5). Utilizing the Japanese MITI test, 0% of the Theoretical BOD was reached in 4 weeks(6) indicating that biodegradation is not an important environmental fate process in soil(SRC). No degradation of methyl t-butyl ether occurred after 40 days using a top soil and activated sludge inoculum(7).

AQUATIC FATE: Based on a classification scheme(1), a Koc range of 11-12(2,3) indicates that methyl t-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 5.87X10-4 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 4 hours and 4 days, respectively(SRC). According to a classification scheme(6), a BCF of 1.5(7) suggests the potential for bioconcentration in aquatic organisms is low(SRC). Methyl t-butyl ether persists in groundwater under both aerobic and anaerobic conditions because it resists physical, chemical, and microbial degradation(8). Utilizing the Japanese MITI test, 0% of the Theoretical BOD was reached in 4 weeks(9) indicating that biodegradation is not an important environmental fate process in water(SRC). No degradation of methyl t-butyl ether occurred after 60 days using an inoculum of sandy aquifer material(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl t-butyl ether, which has a vapor pressure of 250 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl t-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 7 days(SRC), calculated from its rate constant of 2.94X10-12 cu cm/molecule-sec at 25 °C(3). Aliphatic ethers, such as methyl t-butyl ether, do not absorb light at wavelengths >290 nm(4), and, therefore, methyl t-butyl ether is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome

法规信息

TSCA Requirements · 2 条

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. Propane, 2-methoxy-2-methyl- is included on this list. Effective date: 12/15/86; Sunset date: 12/15/96.

A testing consent order is in effect for methyl tert-butyl ether for health effects testing. Federal Register publication date: March 31, 1988.

Atmospheric Standards · 1 条

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Methyl tert butyl ether is included on this list.

CERCLA Reportable Quantities · 1 条

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

State Drinking Water Standards · 4 条

(CA) CALIFORNIA 13 ug/L /Secondary enforceable standard/

(DE) DELAWARE 10 ug/L

(NJ) NEW JERSEY 70 ug/L

(NY) NEW YORK 10 ug/L

State Drinking Water Guidelines · 5 条

(CA) CALIFORNIA 13 ug/L

(CT) CONNECTICUT 70 ug/L

(FL) FLORIDA 35 ug/L

(MA) MASSACHUSETTS 70 ug/L

For more State Drinking Water Guidelines (Complete) data for Methyl t-butyl ether (7 total), please visit the HSDB record page.

Federal Drinking Water GuidelinesEPA 20-40 ug/L

安全数据

F
3-10
wgk
3
tsca
TSCA listed
毒性
. LC50 in mice (15 min): 1.6 mmol/liter of atmosphere (Marsh)
RTECS号
KN5250000
包装类别
II
毒性防护 · 3 条

急性毒性口服-大鼠 LD50: 4000 毫克/公斤; 吸入-小鼠 LC50: 141克/立方米/15分

刺激数据皮肤-兔子 10 毫克/24小时 轻度; 眼睛-兔子 50 微克 重度

职业标准TWA 100 毫克/立方米; STEL 200 毫克/立方米

包装储运 · 4 条

爆炸物危险特性与空气混合形成爆炸性混合物

可燃性危险特性易燃; 火场排放辛辣刺激烟雾

储运特性库房通风低温干燥; 与氧化剂分开储运存放

灭火剂干粉, 二氧化碳; 1211; 泡沫

化学与工业

药理信息

Biological Half-Life · 5 条

MTBE is rapidly metabolized and excreted with a half-life of approximately 30 min /Rats/.

Groups of male and female rats /strain not specified/ received a single 6 hr exposure to methyl tert-butyl ether (MTBE) vapor in nose-only inhalation chambers at targeted MTBE concentrations of 400 and 8000 ppm and daily repeat 6 hr exposures for 15 days at a targeted MTBE concentration of 400 ppm ... The elimination half-life (t1/2) of MTBE was approximately the same after single low- and high-concentration exposures (0.52 and 0.63 hr, respectively). After the repeat exposures, the MTBE t1/2 was slightly shorter (0.48 and 0.51, respectively). The TBA /tert-butyl alcohol/ t1/2 ranged from 2.8 to 3.4 hr after the low- and high-concentration single exposures. After the repeat exposure regimen, the TBA t1/2 was significantly lower (1.8 and 1.5 hr in the male and female rats, respectively).

Healthy male volunteers were exposed via inhalation to gasoline oxygenates methyl tert-butyl ether (MTBE)... The half-times for MTBE in blood were about 1.7 and 3.8 hr. In urine, /MTBE/ showed half-times of about 4 hr ... .

MTBE was rapidly cleared from blood with a half-life of 2.6 +/- 0.9 hr in humans and 0.5 +/- 0.2 hr in 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. ... 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. ... All metabolites of MTBE and ETBE excreted with urine were eliminated with half-times of less than 20 hours. ...

Metabolism/Metabolites · 6 条

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. ...

Methyl tert-butyl ether (MTBE) is ... metabolized to tert-butanol in rats. The metabolism of (14)C-MTBE has been studied in Fischer 344 rats exposed by the inhalation, oral, dermal, and intravenous routes. Respiratory and urinary metabolites were generally similar following exposure of Fischer 344 rats by all routes, indicating pathways are not route-dependent. After exposure by all routes, most of the exhaled radioactivity was due to unchanged MTBE and tert-butanol, with MTBE predominating. Only a small amount of (14)C-carbon dioxide was detected. MTBE and tert-butanol were generally not found in the urine, but four urinary metabolites were isolated, with two identified as alpha-hydroxyisobutyric acid and 2-methyl-1,2-propanediol. The two other metabolites remained unidentified. After inhalation and oral exposure, there was a larger fraction of exhaled tert-butanol in low dose rats than in high dose rats. In inhalation experiments, rats were exposed to (14)C-MTBE at 400 or 8000 ppm for 6 hr or to 400 ppm unlabeled MTBE for 6 hr per day for 14 days, then to 400 ppm (14)C-MTBE on day 15. tert-Butanol accounted for 25 and 30% of the recovered radioactivity in expired air at 3 hr after the single and repeated low exposure concentration, respectively. Exposure to the higher concentration for 6 hr resulted in a lower fraction recovered (7-10%) as a result of to tert-butanol. At 3-6 hr after exposure, tert-butanol represented 72-80% of the radioactivity at the low dose in the single and repeated exposure experiments and 43-54% at the high dose. Results of dosing Fischer 344 rats with (14)C-MTBE intravenously were similar to those obtained by the inhalation, oral and dermal routes. In Charles River CD (Sprague-Dawley) rats injected with a single intraperitoneal dose of 232 mg/kg (14)C-MTBE, blood, tissue, expired air, urine, and feces were sampled at various times up to 48 hr. At 6 hr about 92% of the radioactive dose was eliminated in expired air, 99.1% of which was unchanged MTBE. An average of 7.38% of the administered dose was expired as radiolabeled carbon dioxide. Analysis of the urine revealed that radiolabeled formic acid accounted for 96.6% of the urinary radioactivity. The remaining radioactivity in the urine was assumed to be radiolabeled methanol and formaldehyde. Methanol and formic acid were also detected in plasma, kidney, and liver. No tert-butanol was found in the urine. The metabolism of MTBE to formaldehyde was studied using liver microsomes from control and phenobarbital-pretreated rats (strain not specified). Phenobarbital pretreatment approximately doubled the formation of formaldehyde from MTBE. Further metabolism of formaldehyde yields methanol and/or formic acid; the probable enzymes and cofactors are alcohol dehydrogenase and NADH for the formation of methanol and aldehyde dehydrogenase and NAD for the formation of formic acid.

Exposure to methyl tertiary-butyl ether (MTBE) previously /has/ been shown to alter various muscle, kidney, and liver metabolic activities. In the present study, the metabolism of MTBE by liver microsomes from acetone- or phenobarbital-treated Sprague-Dawley rats was studied at concn of up to 5 mM MTBE. Equimolar amounts of tertiary- butanol, as measured by head-space gas chromatography, and formaldehyde were formed. The Vmax for the demethylation increased by 4 fold and 5.5 fold after acetone and phenobarbital treatments, respectively. The apparent Km value of 0.70 mM using control microsomes was decreased slightly after acetone treatment, but was increased by 2 fold after phenobarbital treatment. The metabolism of MTBE (1 mM) was inhibited by 35% by monoclonal antibodies against p450IIE1, the acetone/ethanol inducible form of cytochrome p450, suggesting a partial contribution by this isozyme. A single 18 hr pretreatment of rats with 1 or 5 mL/kg MTBE (ip) resulted in a 50 fold induction of liver microsomal pentoxyresorufin dealkylase activity but no change in N-nitrosodimethylamine demethylase activity. These trends in activity agreed with immunoblot analysis which showed an elevation in p450IIB1 but no change in p450IIE1 level.

/The/ human liver is active in the oxidative metabolism of ETBE and TAME. A large interindividual variation in metabolizing these gasoline ethers was observed in 15 human liver microsomal samples. The microsomal activities in metabolizing methyl tert-butyl ether (MTBE), ethyl tert-butyl ether (ETBE), and tert-amyl methyl ether (TAME) were highly correlated among each other (r, 0.91-0.96), 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 liver microsomes showed that the highest degree of correlation was with human CYP2A6 (r, 0.90-0.95) ... CYP2A6 displayed the highest turnover number in metabolizing gasoline ethers among a battery of human CYP enzymes expressed in human B-lymphoblastoid cells. Kinetic studies on MTBE metabolism with three human liver microsomes exhibited apparent Km values that ranged from 28 to 89 uM and the V(max) values from 215 to 783 pmol/min/mg, with similar catalytic efficiency values (7.7 to 8.8 uL/min/mg protein). 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 Methyl t-butyl ether (9 total), please visit the HSDB record page.

Tert-butyl methyl ether has known human metabolites that include tert-butanol.

MeSH Pharmacological Classification · 2 条

Any substance in the air which could, if present in high enough concentration, harm humans, animals, vegetation or materials. Substances include GASES; PARTICULATE MATTER; and volatile ORGANIC CHEMICALS.

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.

Absorption, Distribution and Excretion · 5 条

... 10 healthy male volunteers /were exposed/ to methyl tert-butyl ether (MTBE) vapor at 5, 25 and 50 ppm for 2 hr during light physical exercise. Uptake and disposition were studied by measuring MTBE and tert-butyl alcohol (TBA) in inhaled and exhaled air, blood and urine. Low uptake, high post-exposure exhalation, and low blood clearance indicate slow metabolism of MTBE relative to many other solvents. A low recovery of TBA in urine (below 1% of uptake) indicates further metabolism of TBA. The concentration of MTBE and TBA in blood was proportional to exposure level suggesting linear kinetics up to 50 ppm. The half life of 7-10 hr in blood and urine indicates that TBA would be more suitable than the parent compound as a biomarker for MTBE exposure. Subjective ratings (discomfort, irritative symptoms, CNS effects) and eye (redness, tear film break-up time, conjunctival damage, blinking frequency) and nose (peak expiratory flow, acoustic rhinometry, inflammatory markers in nasal lavage) measurements indicated no or minimal effects of MTBE.

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. ...

Groups of male and female rats /strain not specified/ received a single 6 hr exposure to methyl tert-butyl ether (MTBE) vapor in nose-only inhalation chambers at targeted MTBE concentrations of 400 and 8000 ppm and daily repeat 6 hr exposures for 15 days at a targeted MTBE concentration of 400 ppm. Four rats/sex/group were then euthanized and examined. Steady-state plasma concentrations were reached at approximately 4 to 6 hr for MTBE and roughly 6.5 hr for TBA /tert-butyl alcohol/, the principal metabolite of MTBE. MTBE-metabolizing enzymes were saturated during high-concentration exposure. The elimination half-life (t1/2) of MTBE was approximately the same after single low- and high-concentration exposures (0.52 and 0.63 hr, respectively). After the repeat exposures, the MTBE t1/2 was slightly shorter (0.48 and 0.51, respectively). The TBA t1/2 ranged from 2.8 to 3.4 hr after the low- and high-concentration single exposures. After the repeat exposure regimen, the TBA t1/2 was significantly lower (1.8 and 1.5 hr in the male and female rats, respectively). There was a slight, but statistically significant, sex difference in the pharmacokinetics of MTBE (e.g., plasma clearance was faster in females), but no sex differences in the elimination kinetics of TBA were observed.

In a group of 2 healthy men and 2 healthy women experimentally exposed to 1.7 ppm methyl tert-butyl ether (MTBE) for 1 hr, mean blood levels of MTBE rose steeply from a level of 0.83 ug/L preexposure to 17.14 ug/L at the end of the 1-hr exposure, followed by a decline to an average level of 9.74 ug/L at 40 minutes postexposure and 6.32 ug/L at 60 minutes postexposure.

For more Absorption, Distribution and Excretion (Complete) data for Methyl t-butyl ether (9 total), please visit the HSDB record page.

用途与制造

Uses · 6 条

Nearly all methyl tert-butyl ether produced in the United States is used as an additive in unleaded gasoline to increase octane levels and reduce carbon monoxide emissions. It was used in the past to produce isobutene.

Used as a additive for unleaded gasolines to improve combustion; it has been used to dissolve gallstones by delivering MTBE into the gallbladder through surgical tubing; [ATSDR ToxFAQs]

EPA announced in March 2000 plans to ban MTBE because of problems with groundwater contamination.

Octane booster for unleaded gasoline (up to 7% by volume), manufacture of isobutene.

Chromatographic eluent

Methyl tert-butyl ether is also used in the petrochemical industry. By reversal of its formation reaction, MTBE can be cracked to isobutene and methanol on acidic catalysts at higher temperature than MTBE synthesis. In principle, the decomposition of MTBE could be carried out at an acid resin catalyst in the liquid phase, but since the reaction is endothermic and due to equilibrium limitations at lower temperature, this decomposition process should be operated at higher temperatures (> 150 °C) in the gas phase. Several companies have developed process technologies for the MTBE decomposition (e.g. Snamprogetti, Exxon, Sumitomo and Evonik Oxeno).

U.S. Production · 6 条

2023: 7,000,000,000 - <8,500,000,000 lb

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1981) 3.45X10+11 GRAMS

(1990) 8.89 billion lb

(1991) 9.57 billion lb

For more U.S. Production (Complete) data for Methyl t-butyl ether (13 total), please visit the HSDB record page.

Consumption Patterns · 3 条

Gasoline octane component, 100%.

CHEMICAL PROFILE: Methyl tert-butyl ether. Demand: 1988: 65,500 barrels per day; 1989: 72,500 barrels per day; 1993 /projected/: 90,000 barrels per day (average daily consumption; foreign trade is negligible).

CHEMICAL PROFILE: MTBE. Demand: 1994, 176,000 barrels per day; 1995, 220,000 barrels per day; 1999 (projected), 350,000 barrels per day (average daily consumption).

Consumer UsesLaboratory chemicals
Industry UsesFuel
Methods of Manufacturing · 4 条

Methyl tert-butyl ether can be obtained by the acid-catalyzed addition of methanol to isobutene. Suitable catalysts are solid acids such as bentonites, zeolites and-commonly used in industrial world scale MTBE-production units-macroporous acidic ion-exchange resins. The addition reaction is weakly exothermic with a heat of reaction of -37.7 kJ/mol.

LIQUID-PHASE SELECTIVE REACTION OF ISOBUTYLENE FROM A MIXED C4 STREAM WITH METHANOL IN THE PRESENCE OF AN ION EXCHANGE RESIN CATALYST, EG, SULFONATED STYRENE CROSSLINKED WITH DIVINYL BENZENE.

Catalytic reaction of methanol and isobutene (38-93 °C at 100-200 psi). There are several variations of the process.

From methanol and t-butyl alcohol; from methanol and isobutylene; from t-butyl alcohol and diazomethane.

应用领域 · 6 条

简介甲基叔丁基醚(MTBE)曾有一段时间被认为是不可替代的高辛烷值汽油组分,被称为80年代“第三代石油化学品”。由于其可提高无铅汽油的氧含量,使汽油燃烧更充分,减少一氧化碳和苯等有害物质的排放,并可替代四乙基铅作抗暴剂,满足了生产高辛烷值无铅汽油的要求,导致其需求量迅速增长,是理想的高辛烷值汽油添加剂。MTBE是生产无铅、高辛烷值、含氧汽油的理想调合组份,不仅能有效提高汽油辛烷值,而且还能改善汽车性能,降低排气中CO含量,同时降低汽油生产成本。另外甲基叔丁基醚还是一种重要化工原料,可以重新裂解为异丁烯,作为橡胶及其它化工产品的原料。但目前MTBE去产能化明显。

应用目前MTBE主要有三种应用:作为汽油添加剂;裂解为高纯度异丁烯,用于生产MMA、丁基橡胶;医药用途。其中超过90%用于汽油添加剂,调和汽油用途依旧是MTBE产业发展的主导方向。

用途甲基叔丁基醚(MTBE)主要用作汽油添加剂,具有优良的抗爆性。它与汽油的混溶性好,吸水少,对环境无污染。MTBE能改善汽油的冷起动特性和加速性能,对气阻没有不良影响。虽然甲基叔丁基醚热值低,但行车试验证明使用含10%MTBE的汽油能使燃料消耗下降7%,并使废气中含铅量、CO量特别是致癌多环芳烃的排放物明显降低。作为有机合成原料,可制高纯度的异丁烯。还可用于生产2-甲基丙烯醛、甲基丙烯酸及异戊二烯等。另外,还可用作分析溶剂、萃取剂。

用途主要用作汽油添加剂,代替四乙基铅,提高辛烷值,亦可裂解制得异丁烯。

用途溶剂。色谱中尤其是高压液相色谱中用作脱剂。有机合成。无铅汽油中辛烷传爆剂。

用途该品主要用作汽油添加剂,具有优良的抗爆性。它与汽油的混溶性好,吸水少,对环境无污染。MTBE能改善汽油的冷起动特性和加速性能,对气阻没有不良影响。虽然甲基叔丁基醚热值低,但行车试验证明使用含10%MTBE的汽油能使燃料消耗下降7%,并使废气中含铅量、CO量特别是致癌多环芳烃的排放物明显降低。作为有机合成原料,可制高纯度的异丁烯。还可用于生产2-甲基丙烯醛、甲基丙烯酸及异戊二烯等。另外,还可用作分析溶剂、萃取剂。

制备方法

生产方法以混合丁烯和甲醇为原料,在酸性催化剂存在下,进行放热反应而得。具有代表性的工艺是德国赫斯和意大利斯纳姆普罗吉蒂法。美国化学研究、许可证公司和新化学公司开发的一种催化精馏新工艺已于1981年开始应用。此法把催化固定床反应器与蒸馏塔合于同一设备内,利用反应的释热于甲基叔丁基醚的蒸馏提纯,使过程的能耗降低。原料消耗定额:甲醇361kg/t、异丁烯(100%)650kg/t。

生产方法以混合丁烯和甲醇为原料,在酸性催化剂存在下,进行放热反应而得。具有代表性的工艺是德国赫斯和意大利斯纳姆普罗吉蒂法。美国化学研究、许可证公司和新化学公司开发的一种催化精馏新工艺已于1981年开始应用。此法把催化固定床反应器与蒸馏塔合于同一设备内,利用反应的释热于甲基叔丁基醚的蒸馏提纯,使过程的能耗降低。原料消耗定额:甲醇361kg/t、异丁烯(100%)650kg/t。

试剂价格

L14030 · 2500ml
叔丁基甲醚tert-Butyl methyl ether — 585元
041839 · 1L
叔丁基甲醚, HPLC级, 99+%, 氩气下可重封的ChemSeal™瓶包装tert-Butyl methyl ether, HPLC grade, 99+%, packaged under Argon in resealable ChemSeal™ bottles, Thermo Scientific Chemicals — 732元

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