2-Methyl-2-butanol
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2-Methyl-2-butanol
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CAS No:
75-85-4
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Formula:
C5H12O
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Chemical Name:
2-Methyl-2-butanol
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Synonyms:
2-Butanol,2-methyl-;tert-Pentyl alcohol;2-Methyl-2-butanol;tert-Amyl alcohol;Amylene hydrate;Dimethylethylcarbinol;tert-Pentanol;Ethyldimethylcarbinol;1,1-Dimethyl-1-propanol;2-Methyl-2-hydroxybutane;2-Ethyl-2-propanol;2-Hydroxy-2-methylbutane;NSC 25498
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CAS No:
Description
colourless liquid with a camphor-like odour Amyl alcohol is produced during the fermentation of grains, potatoes, and beets. It is also produced during the acid hydrolysis of petroleum fraction. Amyl alcohol is widely used in industry. For example, in the manufacturing of lacquers, paints, varnishes, perfumes, pharmaceuticals, plastics, rubber, explosives, hydraulic fl uids, for the extraction of fats, is also used in the petroleum refi nery industries Amyl alcohols (pentanols) have eight i
Tert-amyl alcohol appears as a clear, colorless liquid with an odor of camphor. Slightly soluble in water.|Liquid
Tert-amyl alcohol appears as a clear, colorless liquid with an odor of camphor. Slightly soluble in water.|2-methylbutan-2-ol is a tertiary alcohol that is propan-1-ol in which both of the hydrogens at position 1 have been replaced by methyl groups. It has a role as a protic solvent. It is a tertiary alcohol and an aliphatic alcohol.
2-Methyl-2-butanol Basic Attributes
88.15
88.15
1361351
200-908-9
69C393R11Z
760354|25498
1105
DTXSID0041436
Colorless liquid
29051500
Characteristics
20.2
0.9
Clear colorless Liquid
0.8096 g/cm3 @ Temp: 20 °C
-8.8 °C
102.4 °C @ Press: 760 Torr
20 °C
1.404-1.406
H2O: 120 g/L (20 ºC);Miscible with alcohol, ether, benzene, chloroform, glycerol, oils and acetone.
Flammables area
15.5 hPa (20 °C)
3 (vs air)
Oral-Rat LD50: 1000 mg/kg; Oral-Mouse LDL0:2500 mg/kg
In case of fire, high temperature, oxidant is more flammable; burning produces irritating smoke
1.3-9.6%(V)
Characteristic odor
Burning taste
Solution neutral to litmus
1.38e-05 atm-m3/mole|Henry's Law constant = 1.38X10-5 atm-cu m/mol
Wt/gal: 6.76 lb|Specific heat at 20 deg K = 3.15 J/g-deg K|Heat of fusion = 90.71 kcal/mol at 25 °C|Dielectric constant = 5.78 at 25 °C|Hydroxyl radical reaction rate constant = 4.9X10-12 cu cm/molecule-sec at 25 °C (est)
Highly flammable. Slightly soluble in water.
Alcohols and Polyols
Highly Flammable
TERT-AMYL ALCOHOL attacks plastics [Handling Chemicals Safely 1980. p. 236]. Reacts violently with acetyl bromide [Merck 11th ed. 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: an explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73 1967; J, Org. Chem. 28:1893 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M, 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].
819 °C
789.45 kcal/mol at 25 °C
Lower flammable limit: 1.2% by volume; Upper flammable limit: 9.0% by volume
40.11 kJ/mol at boiling point
Critical temperature = 272.0 °C; Critical pressure = 3880 kPa
Safety Information
II
3
UN 1105 3/PG 2
1
11-20-37/38-41-21
46-39-36/37-26
SC0175000
F,Xn
Treasury is ventilated, low temperature and dry; stored separately from oxidant
Explosive when mixed with air
Light sensitive. Highly flammable. Incompatible with strong oxidizing agents.
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P312, P304+P340, P312, P321, P332+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
H225
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.|Incineration /SRP: with appropriate emissions controls/. /Amyl alcohols/
Forms explosive mixture with air. Contact with strong oxidizers and hydrogen trisulfide may cause fire and explosions. Incompatible with strong acids. Violent reaction with alkaline earth metals forming hydrogen, a flammable gas. /Amyl alcohols/
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016)|Flammable - 3rd degree
|Danger|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P312, P304+P340, P312, P321, P332+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P332+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 766 companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P307+P311, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|Wear solvent resistant gloves and clothing to prevent any reasonable probability of skin contact. ACGIH and safety equipment suppliers/manufacturers recommend polyvinyl alcohol, polyvinyl chloride, neoprene, butyl rubber, neoprene + styrene-butadiene rubber (SBR), polyurethane, SBR, and SBR/neoprene as protective materials. All protective clothing (suits, gloves, footwear, headgear) should be clean, available for work each day, and put on before work. Contact lenses should not be worn when working with this chemical. Wear splash-proof chemical goggles and face shield unless full face-piece respiratory protection is worn. Employees should wash immediately with soap when skin is wet or contaminated. Remove nonimpervious clothing immediately if wet or contaminated. Provide emergency showers and eyewash. /Amyl alcohols/
FLAMMABLE, DANGEROUS FIRE RISK.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Amyl alcohols/
Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or similar material and deposit in sealed containers. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable. /Amyl alcohols/|The objective of this study was to operate a novel, field-scale, aerobic bioreactor and assess its performance in the ex situ treatment of groundwater contaminated with gasoline from a leaking underground storage tank in Pascoag, RI. The groundwater contained elevated concentrations of MTBE (methyl tert-butyl ether), TBA (tert-butyl alcohol), TBF (tert-butyl formate), BTEX (benzene, toluene, ethyl benzene, and xylene isomers), and other gasoline additives (tert-amyl methyl ether, di-isopropyl ether, tert-amyl alcohol, methanol, and acetone). The bioreactor was a gravity-flow membrane-based system called a Biomass Concentrator Reactor (BCR) designed to retain all biomass within the reactor. It was operated for six months at an influent flow rate that ultimately reached 5 gpm. The goal was to achieve a removal of all contaminants to <5 ug/L, which is the California Drinking Water advisory for MTBE. The concentration of TBA, an MTBE biodegradation byproduct, was consistently lower than that of MTBE. The other daughter compound detected in the influent, TBF, was degraded to concentrations below the detection limit of 0.02 ug/L. BTEX were consistently degraded to significantly lower levels in the effluent throughout the duration of the study (<1 ug/L). A similar high removal efficiency of the other gasoline oxygenates present in the groundwater (TAME, DIPE, and TAA) was also achieved. ...|Environmental considerations-land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Amyl alcohols/|Environmental considerations-water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Amyl alcohols/|Environmental considerations-air spill Apply water spray or mist to knock down vapors. /Amyl alcohols, combustible liquid/
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Amyl alcohols/|Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and waterg. /Amyl alcohols/|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
... Skin contact can cause irritation. Inhalation can irritate the eyes and respiratory system ... /Amyl alcohols/
| 1 - Materials that, under emergency conditions, can cause significant irritation.| 3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.| 0 - Materials that in themselves are normally stable, even under fire conditions.
2-Methyl-2-butanol was identified in final effluent from an oil refinery in Lockport, IL(1). It was present in trench leachate at the Maxey Flats, KY and West Valley, NY radioactive waste disposal sites(2). It was tentatively identified in the effluent of a sewage treatment works in Luton, England that fed into the River Lee(3).
Toxicity
moderately toxic
2-Methyl-2-butanol (4.1 mmol/kg) induced a behavioral intoxication in rats (male, Sprague-Dawley, 160 to 300 g) at 8 min after the intraperitoneal administration of the pentanol. The intoxication was scored on a scale of 0 to 4, where 3 = 'very little or no recovery of righting reflex, heavy sedation, no spontaneous locomotor activity, flaccid muscles, absence of pelvic and abdominal elevation' and 2 = 'heavy sedation, pronounced motor coordination and sluggish movement, limbs extended away from the body'. After 2-methyl-2-butanol alone the intoxication was scored as approximately 2.9. The prior administration of the imidazobenzodiazepine Ro15-4513 (5 min before the alcohol) partially reversed the intoxication by 2-methyl-2-butanol and the score decreased to approximately 1.8. The Ro15-4513 was more effective at reducing the intoxication after treatment with ethanol than after treatment with the pentanol.
LD50 Rat oral 1.0-2.0 g/kg|LD50 Rabbit oral 2.0 g/kg|LD50 Mouse iv 0.61 g/kg|LD50 Rabbit dermal 1.72 g/kg
/AQUATIC SPECIES/ 2-Methyl-2-butanol induced /CNS depression/ in tadpoles at 58 mM (lowest active concentration) and also induced /CNS depression/ in isolated frog heart at 182 mM (lowest active concentration). In a similar study, the threshold /CNS depressant/ concentrations in tadpoles was 55 mM for 2-methyl-2-butanol.
2-Methyl-2-butanol has been identified as a volatile in cassava(1) and fried bacon(2) suggesting that it may be a naturally-occurring chemical(SRC).
2-Methyl-2-butanol's production and use as a solvent for resins (1), floatation agent, and in organic synthesis(2) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 73(SRC), determined from a log Kow of 0.89(2) and a regression-derived equation(3), indicates that 2-methyl-2-butanol is expected to have high mobility in soil(SRC). Volatilization of 2-methyl-2-butanol from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.38X10-5 atm-cu m/mole(4). 2-Methyl-2-butanol is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 16.7 mm Hg(5). 2-Methyl-2-butanol is expected to be resistant to biodegradation in soil(SRC) based on results from several screening studies (6-9). 2-Methyl-2-butanol contains a tertiary structure which is expected to decrease its biodegradability(10).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 73(SRC), determined from a log Kow of 0.89(2) and a regression-derived equation(3), indicates that 2-methyl-2-butanol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.38X10-5 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 2 and 22 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 2-Methyl-2-butanol is expected to be resistant to biodegradation in water(SRC) based on results from several screening studies (7-10). 2-Methyl-2-butanol contains a tertiary structure which is expected to decrease its biodegradability(11).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-methyl-2-butanol, which has a vapor pressure of 16.7 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-methyl-2-butanol 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 3.3 days(SRC), calculated from its rate constant of 4.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2-Methyl-2-butanol 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 2-methyl-2-butanol with photochemically-produced hydroxyl radicals has been estimated as 4.9X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Methyl-2-butanol is not expected to undergo hydrolysis in the environment as alcohols are stable under environmental conditions(2). 2-Methyl-2-butanol 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 3 was calculated in fish for 2-methyl-2-butanol(SRC), using a log Kow of 0.89(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 2-methyl-2-butanol is estimated as 73(SRC), using a log Kow of 0.89(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-methyl-2-butanol is expected to have high mobility in soil.
The Henry's Law constant for 2-methyl-2-butanol is 1.38X10-5 atm-cu m/mole(1). This Henry's Law constant indicates that 2-methyl-2-butanol is expected to volatilize 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 2 days(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 22 days(SRC). 2-Methyl-2-butanol's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 2-Methyl-2-butanol is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 16.7 mm Hg(3).
DRINKING WATER: 2-Methyl-2-butanol has been identified in drinking water concentrates from tap water in New Orleans, LA(1). The water was from the Mississippi River.
2-Methyl-2-butanol has been identified as a volatile in cassava(1) and fried bacon(2).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 57 workers are potentially exposed to 2-methyl-2-butanol in the US(1). Occupational exposure to 2-methyl-2-butanol may occur through inhalation and dermal contact with this compound at workplaces where 2-methyl-2-butanol is produced or used. Monitoring data indicate that the general population may be exposed to 2-methyl-2-butanol via ingestion of food and drinking water, and dermal contact with this compound and other products containing 2-methyl-2-butanol(SRC).
The urine of Finnish gasoline road-tanker drivers involved in loading and unloading 95- and 98-octane unleaded gasoline contained 2-methyl-2-butanol, a metabolite of methyl tert-amyl ether, at concentrations of 40 nmol/L (first urine after the work shift) and 20 nmol/L (next morning sample)(1). 2-Methyl-2-butanol was not detected in either blood or urine samples of gasoline road-tanker drivers collected in either October 1994 (n=13, urine; n=14, blood) or August 1995 (n=20, blood and urine samples; limit of quantitation <100 nmol/L)(2).
Drug Information
Dog weighing 11 kg, when injected sc with dose of 0.1 mL of 2-methyl-2-butanol...exhaled 65% of it within 5.75 hr. Another dog given slightly larger dose of same alc iv exhaled 52% within 6 hr. Cats also exhaled large quantity unchanged.|When rabbits were injected with 2 levels of dosage ... they exhaled, in first instance 21% of alc in unchanged form within 4 hr, & in second, 22% within 3 hr. ... rat given 1 g/kg of same isomer eliminated 26.4% unchanged in expired air and 8.9% in the urine within 50 hr.|The rate of elimination of amyl alcohols from the blood of rats decreases in the order of primary, secondary, and tertiary. tert-Amyl alcohol did not disappear from the blood of rats until 50 hr following an ip dose of 1 g/kg.|Small amts of the primary and secondary alcohols, and appreciable amts of the tertiary isomer, are excreted unchanged in the respired air and urine. /Amyl alcohols/|... /The authors/ Found a conc of 12.5 mg percent of tert-amyl alcohol in the blood of rats 1 hr following an ip dose of 1.0 kg. They also found a conc of 191 mg percent in the jugular blood of rats at the time of death from respiratory failure. Conc in the plasma of rats about 0.6 hr after they had inhaled 150, 500, or 1500 ppm of tert-amyl alcohol for 6 hr were 9.6, 59.9, and 337 ug/mL, respectively.
... the biotransformation of tert-Amyl methyl ether (TAME) /was studied/ in rats and one human volunteer after inhalation of (12)C- or (13)C-labeled TAME. In addition, the biotransformation of [(13)C]-tert-amyl alcohol was studied in rats after gavage. ... 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 ... 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)C]TAME-treated rats. Our results suggest that TAME is extensively metabolized by rats and humans to tert-amyl alcohol which may be further oxidized to diols and carboxylic acids. These reactions are likely mediated by cytochrome P450-dependent oxidations.|... The objective of this study was to use a physiologically-based pharmacokinetic (PBPK) model to describe the disposition of tert-amyl methyl ether (TAME) and its major metabolite, tert-amyl alcohol (TAA), in male Fischer-344 rats. The model compartments for TAME and TAA were flow-limited. The TAME physiological model had 6 compartments: lung, liver, rapidly perfused tissues, slowly perfused tissues, fat, and kidney. The TAA model had 3 compartments: lung, liver, and total-body water. The 2 models were linked through metabolism of TAME to TAA in the liver. Model simulations were compared with data on blood concentrations of TAME and TAA taken from male Fischer-344 rats during and after a 6-hour inhalation exposure to 2500, 500, or 100 ppm TAME. The PBPK model predicted TAME pharmacokinetics when 2 saturable pathways for TAME oxidation were included. The TAA model, which included pathways for oxidation and glucuronide conjugation of TAA, underpredicted the experimental data collected at later times postexposure. To account for biological processes occurring during this time, three hypotheses were developed: nonspecific binding of TAA, diffusion-limited transport of TAA, and enterohepatic circulation of TAA glucuronide. These hypotheses were tested using three different model structures. Visual inspection and statistical evaluation involving maximum likelihood techniques indicated that the model incorporating nonspecific binding of TAA provided the best fit to the data. ...|The biotransformation of ... tert-amyl methyl ether (TAME) was studied in humans and in rats after inhalation of 4 and 40 ppm of ... TAME ... for 4 hours, and the biotransformation of ... TAME was studied after ingestion exposure in humans to 5 and 15 mg in water. .../Following ingestion/ 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 ... TAME /was/ 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 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 ... TAME /was/ ... rapidly absorbed from the gastrointestinal tract. Hepatic first-pass metabolism ... was not observed, and a significant part of the administered dose was transferred into blood and cleared by exhalation. Metabolic pathways for ... TAME and kinetics of excretion were identical after ingestion and inhalation exposures. ...|... Male mice of ICR strain were exposed to about 5% /isopentane/ for one hour while the oxygen in the environmental air was maintained at about 20%. Then their blood and liver tissue were collected and analyzed by means of GC and GC-MS. The metabolites thus obtained were ... 3-methyl-2-butanol, 2-methyl-2-butanol and 3-methyl-2-butanone were detected as the resultant metabolites. In the presence of the NADPH-generating system liver microsomes were made to react to the substrate of saturated ... isopentane aqueous solution at 37 degrees C for one hour. As a result, the same metabolites were produced as obtained in the exposure experiment. It was therefore suggested that ... isopentane /was/ metabolized chiefly by liver microsomes. Male mice of ICR strain were fed with 80 mg/kg b.w. of phenobarbital for consecutive four days and exposed to ... isopentane for one hour. This resulted in an increase in the amount of ... 2-methyl-2-butanol in the isopentane inhalation experiment. ...|For more Metabolism/Metabolites (Complete) data for 2-METHYL-2-BUTANOL (7 total), please visit the HSDB record page.|Tert-amyl alcohol is a known human metabolite of tert-amyl methyl ether.
Upon repeated exposure to 50 ppm, the material /2-methyl-2-butanol/ was cleared by rats (t1/2 = 47 min) and dogs (t1/2 = 69 min) in an apparent first-order manner.|Following repeated exposure to 1000 ppm the plasma clearance was more rapid in the mouse than in either the rat or the dog exposed to 50 ppm, the t1/2 times being 29, 47, and 69 min, respectively ... The data demonstrate that the kinetics of tert-amyl alcohol are highly species- and conc-dependent.
Typical impurities are other monomeric alcohols, dimeric alcohols, acetals and several miscellaneous substances ... typically free of suspended matter.
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 2016)
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)
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. /Higher alcohols (>3 carbons) and related compounds/|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. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema 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. Administer activated charcoal ... . /Higher alcohols (>3 carbons) and related compounds/|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 as 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 ... . Monitor for signs of hypoglycemia (decreased LOC, tachycardia, pallor, dilated pupils, diaphoresis, and/or dextrose strip or glucometer readings below 50 mg) and administer 50% dextrose if necessary ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Higher alcohols (>3 carbons) and related compounds/
/SIGNS AND SYMPTOMS/ All /amyl alcohols/ are appreciably irritating to the eyes and capable of causing transient corneal opacity. All are somewhat irritating to the uncovered skin when exposures are repeated and severely irritating when confined to the skin. All can be absorbed through the skin of animals in toxic amts when exposures are severe. High conc of vapor are irritating to the mucous membranes and typically cause central nervous system effects and death by respiratory failure. /Amyl alcohols/|/SIGNS AND SYMPTOMS/ No effects upon the nerves of the skin of men, and no local wheal formation, erythema, or hyperemia were observed ... following the application of tert-amyl alcohol to the skin.|/CASE REPORTS/ The ingestion of 27 g of 2-methyl-2-butanol (amylene hydrate) by an adult female resulted in unconsciousness within 0.5 hr, marked signs of intoxication through the following day, and complete recovery after 14 days. Ingestion of 18 g of 2-methyl-2-butanol by an adult resulted in unconsciousness, a deep sleep lasting more than one day, and a slow recovery. The administration of an enema of approximately 29 g of 2-methyl-2-butanol to an adult male resulted in death after 53 hr, but the case was complicated by concurrent pneumonia in the patient.|/CASE REPORTS/ A neurasthenic brewery manager who inhaled the vapors (primary active amyl and isoamyl isomers) from fermentation vats exhibited ... /CNS/ stimulation, insomnia, and chromatopsia. /Amyl alcohols/|For more Human Toxicity Excerpts (Complete) data for 2-METHYL-2-BUTANOL (6 total), please visit the HSDB record page.
2-methyl-2-butanol
2-Methyl-2-butanol Use and Manufacturing
(1) Using acetone and acetylene as raw materials, it is obtained by acetylation and hydrogenation. The acetylene is dissolved in liquid ammonia, mixed with acetone and catalyst, and then sent to the acetylation reactor. The reaction liquid is flashed to separate the unreacted acetylene and ammonia, and the unreacted acetone is evaporated to obtain methyl butynol Enter the hydrogenation reactor to react to generate tert-amyl alcohol, which is dehydrated and refined to obtain the product. (2) It is made from isoamylene and water. (3) It is produced by fractional distillation of mixed alcohols produced by chlorination and hydrolysis of pentane. The raw material pentane is first dehydrated with anhydrous hydrogen chloride, evaporated and mixed with chlorine to enter the reactor, and the reaction temperature is 250-300°C. The reaction product is rectified and separated by four rectification towers to obtain chloropentane. In the hydrolyzer, sodium oleate is used as a catalyst, and chloropentane is hydrolyzed with sodium hydroxide aqueous solution. The crude pentanol is separated from water and distilled to obtain pentanol containing 59% primary alcohol, 36% secondary alcohol, and 5% tertiary alcohol. . By using acetone and acetylene as raw materials, a product with a purity of 99% can be obtained. Raw material consumption quota: acetone 1040kg/t, calcium carbide 1500kg/t, hydrogen (99.5%) 650m3, liquid ammonia 135kg/t, potassium carbonate 340kg/t.
It is mainly used in the production of new pesticides rustin, pinazone, triazolone, triazolinol, seed protector, etc.; it can also be used to synthesize indane musk and as a coupler for color film. Methylbutynol, an intermediate product for the production of tert-amyl alcohol, is also a useful pharmaceutical intermediate and terpene flavor intermediate, and is used to manufacture acid corrosion inhibitors, viscosity stabilizers, viscosity reducers, and for the manufacture of nickel plating and plating Polishing agent for copper, stabilizer for chlorinated hydrocarbons, etc.
Processing aids, not otherwise listed
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4999]|This chemical is listed as an Extended High Production Volume (EHPV). Chemicals listed as EHPV were produced in or imported into the U.S. in >1 million pounds according to the 2002 Toxic Substances Control Act (TSCA) Inventory Update. The EHPV program is a voluntary initiative that allows companies to demonstrate that adequate screening data exist for organic HPV chemicals.
Grades: Technical; CP; NF.
All other basic organic chemical manufacturing|2-Butanol, 2-methyl-: ACTIVE|The oxo process is the principal one in practice today; only minor quantities, mainly in Europe are obtained from separation of fusel oil. tert-Amyl alcohol is produced on a commercial scale in lower volume by hydration of amylenes.
Method: USGS-NWQL O4024-03; Procedure: gas chromatography/mass spectrometry; Analyte: 1,1-dimethyl-1-propanol; Matrix: whole-water; Detection Limit: 0.2155 ug/kg.
METHOD FOR DETERMINING TERTIARY AMYL ALC IN PLASMA (RAT) EMPLOYS DIRECT INJECTION OF HEPARINIZED PLASMA, SEPARATION BY GAS-LIQ-SOLID CHROMATOGRAPHY & SUBSEQUENT QUANTIFICATION VIA SELECTIVE ION MONITORING MASS SPECTROMETRY.
Food additives -> Flavoring Agents|Fire Hazards -> Flammable - 3rd degree
Flavoring Agents
Computed Properties
Molecular Weight:88.15
XLogP3:0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:88.088815002
Monoisotopic Mass:88.088815002
Topological Polar Surface Area:20.2
Heavy Atom Count:6
Complexity:39.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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