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CAS Number: 75-65-0
EC Number: 200-889-7
Molecular Weight: 74.12
Linear Formula: (CH3)3COH
What is tert-Butyl alcohol?
Tert-butyl alcohol is the simplest tertiary alcohol, with a formula of (CH₃)₃COH.
tert-Butyl alcohol is one of the four isomers of butanol.
tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor.
tert-Butyl alcohol is a simple organic compound that contains only carbon (C), hydrogen (H) and oxygen (O).
The chemical formula for TBA is C4H10O.
As tert-Butyl alcohols name suggests, this chemical contains a tertiary butyl group that consists of three methyl groups (‐CH3), each separately attached to a central (tertiary) carbon.
TBA also contains an alcohol group (‐OH) that is also attached to the central tertiary carbon
tert-Butyl alcohol is a chemical used in coating products, washing & cleaning products, adhesives and sealants, fuels, lubricants and greases, fillers, putties, plasters, and modeling clay.
tert-Butyl alcohol is a low to moderate hazard material and risk of adverse health effects associated with both occupational and consumer use of this chemical is anticipated to be low.
tert-Butyl alcohol is used as a solvent (e.g., for paints, lacquers, and varnishes); as a denaturant for ethanol and several other alcohols; as an octane booster in gasoline; as a dehydrating agent; as a chemical intermediate in the manufacturing of methyl methacrylate; and in the manufacturing of flotation agents, fruit essences, and perfumes.
tert-Butyl alcohol is used in the production of tert-butyl chloride, tert-butyl phenol, andisobutylene; in the preparation of artificial musk; and in denatured alcohols.
Plastics, lacquers, cellulose esters, fruit essences, perfumes, and chemical intermediates; additive to unleaded gasoline
tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH).
tert-Butyl alcohol is one of the four isomers of butanol.
tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor.
tert-Butyl alcohol is miscible with water, ethanol and diethyl ether.
tert-Butanol has been used for a variety of other purposes, including as a dehydrating agent and solvent.
tert-butanol is a polar organic solvent that is used in such large scale applications as the manufacture of flavors, perfumes, and paint removers.
tert-Butyl alcohol is also utilized as a denaturant for ethyl alcohol.
Tert-butanol is a metabolite of the gasoline additive methyl tert-butyl ether (MTBE).
tert-Butanol also is used to manufacture methyl methacrylate plastics and flotation devices.
Cosmetic and food-related uses include the manufacture of flavors, and, because of its camphor-like aroma, tert-Butyl alcohol also is used to create artificial musk, fruit essences, and perfume.
tert-Butyl alcohol is used in coatings on metal and paperboard food containers and industrial cleaning compounds, and can be used for chemical extraction in pharmaceutical applications.
tert-Butyl alcohol is derived commercially from isobutane as a coproduct of propylene oxide production.
tert-Butyl alcohol can also be produced by the catalytic hydration of isobutylene, or by a Grignard reaction between acetone and methylmagnesium chloride.
Purification cannot be performed by simple distillation due to formation of an azeotrope with water, although initial drying of the solvent containing large amounts of water is performed by adding benzene to form a tertiary azeotrope and distilling off the water.
Smaller amounts of water are removed by drying with calcium oxide (CaO), potassium carbonate (K2CO3), calcium sulfate (CaSO4), or magnesium sulfate (MgSO4), followed by fractional distillation.
Anhydrous tert-butyl alcohol is obtained by further refluxing and distilling from magnesium activated with iodine, or alkali metals such as sodium or potassium.
General description of tert-Butyl alcohol:
tert-Butanol (tBA) is a tertiary alcohol.
tert-Butyl alcohol undergoes dehydration by reactive distillation in the presence of solid acid catalyst to form isobutylene with high selectivity.
Lipase-mediated alcoholysis of soybean oil deodorizer distillate (SODD) has been conducted in tBA (as reaction medium) to generate biodiesel.
Formation of 2-tert-butyl-p-cresol (TBC), 2,6-di-tert-butyl-p-cresol (DTBC) and tert-butyl-p-tolyl ether has been reported when p-cresol undergoes butylation by tBA in the presence of 12-tungstophosphoric acid supported on zirconia (TPA/ZrO2) catalyst.
The interaction behavior of tBA on the Si (001)-(2×1) surface has been assessed by using the ab-initio density functional theory (DFT) based on pseudopotential approach.
Uses and Applications of tert-Butyl alcohol:
tert-Butyl alcohol is primarily utilized for its solvent power and fuel oxygenates.
tert-Butyl alcohol is used for the removal of water from substances, in the extraction of drugs, in the manufacture of perfumes, in the recrystallization of chemicals, and as a chemical intermediate.
tert-Butyl alcohol is an authorized denaturant for ethyl alcohol and for several specially denatured alcohols.
Solvent, ethanol denaturant, paint remover ingredient, and gasoline octane booster and oxygenate.
tert-Butyl alcohol is a chemical intermediate used to produce MTBE and ETBE by reaction with methanol and ethanol, and TBHP by reaction with hydrogen peroxide.
Natural occurrence of tert-Butyl alcohol:
tert-Butyl alcohol has been identified in beer and chickpeas.
tert-Butyl alcohol is also found in cassava, which is used as a fermentation ingredient in certain alcoholic beverages.
Preparation of tert-Butyl alcohol:
tert-Butyl alcohol is derived commercially from isobutane as a coproduct of propylene oxide production.
tert-Butyl alcohol can also be produced by the catalytic hydration of isobutylene, or by a Grignard reaction between acetone and methylmagnesium chloride.
Purification cannot be performed by simple distillation due to formation of an azeotrope with water, although initial drying of the solvent containing large amounts of water is performed by adding benzene to form a tertiary azeotrope and distilling off the water.
Smaller amounts of water are removed by drying with calcium oxide (CaO), potassium carbonate (K2CO3), calcium sulfate (CaSO4), or magnesium sulfate (MgSO4), followed by fractional distillation.
Anhydrous tert-butyl alcohol is obtained by further refluxing and distilling from magnesium activated with iodine, or alkali metals such as sodium or potassium.
Other methods include the use of 4 Å molecular sieves, aluminium tert-butylate, calcium hydride (CaH2), or fractional crystallization under inert atmosphere.
Applications of tert-Butyl alcohol:
tert-Butyl alcohol is used as a solvent, ethanol denaturant, paint remover ingredient, and gasoline octane booster and oxygenate.
tert-Butyl alcohol is a chemical intermediate used to produce methyl tert-butyl ether (MTBE) and ethyl tert-butyl ether (ETBE) by reaction with methanol and ethanol, respectively, and tert-butyl hydroperoxide (TBHP) by reaction with hydrogen peroxide.
Tert-Butanol Formula
Tert-Butanol, also known by the name tert-butyl alcohol or t-BuOH, is an isomer of the butanol (alcohols of 4 members) used as solvent, as component of fuels and also as intermediate or reagent in organic synthesis.
Formula and structure: The chemical formula of tert-butanol is C4H9OH and its extended formula is (CH3)3COH.
tert-Butyl alcohols molar mass is 74.12 g mol-1.
The molecule is formed by a central carbon atom which has 3 methyl groups -CH3 attached and 1 hydroxyl group -OH forming a tetrahedrical structure around this central carbon.
Tert-butanol is one of the 4 isomers of the 4 carbon alcohol family.
The chemical structure can be written as below, in the common representations used for organic molecules.
Occurrence: Tert-butanol can be found in nature, particularly in chickpeas and ginger.
tert-Butyl alcohol has also been found in some products that are manufactured by fermentation, for example beers and cassava.
Other methods include the use of 4 Å molecular sieves, aluminium tert-butylate, calcium hydride (CaH2), or fractional crystallization under inert atmosphere
Applications
tert-Butyl alcohol is used as a solvent, ethanol denaturant, paint remover ingredient, and gasoline octane booster and oxygenate.
tert-Butyl alcohol is a chemical intermediate used to produce methyl tert-butyl ether (MTBE) and ethyl tert-butyl ether (ETBE) by reaction with methanol and ethanol, respectively, and tert-butyl hydroperoxide (TBHP) by reaction with hydrogen peroxide.
Preparation: Tert-butanol is obtained as by-side product during the preparation of propylene oxide from the alkane isobutane.
Other methods are the addition of water to 2-methylpropene in an acid-condition or by the reaction of Grignard reaction between acetone and methylmagnesium chloride.
Physical properties: Tert-butanol is a colorless liquid or also a white solid with a sharp alcohol or camphor-like odor.
The density is 0.775g mL-1.
tert-Butyl alcohols melting point is 25 °C and its boiling point is 83 °C.
tert-Butyl alcohol is miscible in water and also soluble in organic solvent as ethyl acetate, ethanol, methanol, benzene and acetone.
Chemical properties: Tert-butanol is one of the four butanol isomers.
tert-Butyl alcohol is the least reactive of this family due to the central carbon is a tertiary carbon (it means that is bond to 3 carbon atoms) which able to get a high stabilization of positive net, thus tert-Butyl alcohol is less reactive.
However, tert-Butyl alcohol can also be deprotonated using a strong base to generated the tert-butoxide anion which is a nucleofile widely used in organic synthesis.
Uses: Tert-butanol is used as an additive in fuels and also as a intermediate in the preparation of plasticizers and other chemical compounds.
tert-Butyl alcohol is a solvent using in laboratory and also a solvent for cleaning and degreasing products.
As a nucleofile, tert-Butyl alcohol is largely used in nucleofilic substitution reactions.
Butyl alcohol (C4H9OH), any of four organic compounds having the same molecular formula but different structures: normal (n-) butyl alcohol, secondary (sec-) butyl alcohol, isobutyl alcohol, and tertiary (t-) butyl alcohol.
All four of these alcohols have important industrial applications.
n-Butyl alcohol is a solvent for paints, resins, and other coatings, and tert-Butyl alcohol is a component of hydraulic brake fluids.
A large quantity of n-butyl alcohol is converted to esters, which have various applications; for example, butyl acetate is used as a paint solvent, and dibutyl phthalate is used as a plasticizer (to keep plastics from becoming brittle).
sec-Butyl alcohol is used in solvents and in esters to a limited extent; larger amounts are oxidized to methyl ethyl ketone (2-butanone), an important solvent for the manufacture of plastics, fabrics, and explosives.
Similar to n-butyl alcohol, isobutyl alcohol is used in solvents and in plasticizers.
Its esters are also used in fruit flavourings.
t-Butyl alcohol is also used as a solvent and as a denaturing agent for ethyl alcohol.
In smaller quantities it is used in flavourings and in perfumes.
Commercial n-butyl alcohol is made by fermentation of corn (maize) or molasses or by condensation and reduction of acetaldehyde.
sec-Butyl alcohol is produced from butene by reaction with sulfuric acid, followed by hydrolysis.
t-Butyl alcohol is similarly produced from isobutylene (2-methylpropene).
Isobutyl alcohol can be made by the hydroformylation of propylene, giving isobutyraldehyde, followed by reduction.
Methyl tertiary-butyl ether (MTBE) is not the only highly soluble, potentially toxic fuel oxygenate found at gasoline release sites.
tert-Butyl alcohol (TBA) can also be found at many sites around the country.
Although often used itself as an octane enhancer an may be a co-contaminant with MTBE, there is some evidence from laboratory studies in the literature that it can be produced from the biological de-methylation of MTBE under aerobic conditions.
We examined these potential sources of TBA to ground-water systems using two approaches.
Physical properties
tert-Butanol is a colorless liquid or crystals with a camphor-like odor.
A detection odor threshold concentration of 2,900 mg/m3 (957 ppmv) was experimentally determined by Dravnieks.
In a later study, Nagata and Takeuchi reported an odor threshold concentration 220 ppbv.
Production Methods of tert-Butyl alcohol:
t-Butyl alcohol is produced as a by-product from the isobutane oxidation process for manufacturing propylene oxide.
t-Butyl alcohol is also produced by the acidcatalyzed hydration of isobutylene, a process no longer used in the United States.
Definition
Tert-butanol is a tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2.
tert-Butyl alcohol has a role as a human xenobiotic metabolite.
tert-Butyl alcohol derives from a hydride of an isobutane.
General Description
Colorless oily liquid with a sharp alcohol odor.
Floats and mixes with water.
Produces irritating vapor.
Freezing point is 78°F.
Air & Water Reactions
Highly flammable. Water soluble.
Preferred IUPAC name
2-Methylpropan-2-ol
Organic chemicals often have several different names.
Some of the other commonly used names for TBA are tert‐butanol, tert‐butyl alcohol, t‐butanol, 2‐methyl‐2‐propanol, 2‐methylpropan‐2‐ol, trimethylcarbinol, and trimethyl methanol.
Each chemical has a unique CAS (Chemical Abstracts Service) Registry Number.
The CAS number for TBA is 75‐65‐0.
This number can be used to obtain specific information about TBA from a wide variety of sources.
What are the main sources of TBA in ground water?
Ultimately, gasoline is likely to be the main source of TBA found in ground water.
To contaminate ground water, gasoline must enter the subsurface.
This can occur through a variety of routes involving, among others, gasoline distribution and end use (e.g., storage system releases and pipe lines) and consumers (e.g., refueling spills, automobile accidents, poor consumer disposal practices).
One important reason why gasoline is an important source of TBA is because biodegradation of other gasoline components such as ether oxygenates (e.g.,methyl‐and ethyl tertiary butyl ether [MTBE and ETBE]) can generate TBA.
Why is only “older” gasoline a potential source of TBA?
Historically, TBA is most closely associated with gasoline that contained fuel oxygenates.
By definition, all oxygenates contain oxygen (O).
This oxygen can increase the efficiency of fuel combustion and decrease automobile emissions of air pollutants such as carbon monoxide.
Is gasoline always a source of TBA?
Gasoline currently sold in the United States is not considered to be a source of TBA while older gasoline already present in the subsurface may be a potential source of TBA.
The reason for this is the composition of gasoline changes over time due to technological advances, environmental regulations, and other factors.
For example, gasoline sold in the United States before the mid 1980’s often contained significant amounts of lead whereas gasoline sold after the mid 1980’s did not.
The composition of gasoline also varies regionally.
For example, currently, much of the gasoline sold in the United State contains approximately 10% ethanol.
Ten years ago, ethanol use in gasoline was largely restricted to the Midwest where tert-Butyl alcohol was produced.
Can TBA in ground water come from non‐gasoline sources?
Several potential non‐gasoline‐related sources of TBA exist.
For example, tertiary butyl acetate (TBAc) is an ester that is widely used as a low volatility solvent.
TBAc degrades both biologically and chemically to TBA.
TBA is also generated from the chemical decomposition of tertiary butyl hydroperoxide, a component of some hydraulic fracturing solutions.
TBA is also a co‐product of commercial propylene oxide production.
Microorganisms that grow on volatile n‐alkanes (methane, propane etc.) can generate TBA from isobutane and so can bacteria that actually grow on isobutane.
Low concentrations of isobutane occur in gasoline but the major sources of isobutane in the environment are sources such as natural gas seeps.
Microorganisms are typically single‐celled organisms that are too small to be seen with the naked eye.
These include, among others, bacteria, archaea and fungi.
Bacteria are the most metabolically versatile microorganisms and in many instances individual bacterial species or microbial communities containing multiple bacterial species can grow on and degrade organic compounds in ground water.
In the case of gasoline, these compounds include both MTBE and TBA, as well as normal and branched alkanes and alkenes, alicyclics and monoaromatic (e.g. BTEX) hydrocarbons.
Microbial growth on these compounds removes these compounds from contaminated environments by converting them to innocuous products such as carbon dioxide (CO2).
Other names: tert-Butyl alcohol; tert-Butanol; Ethanol, 1,1-Dimethyl-; Trimethylcarbinol; Trimethylmethanol
1,1-Dimethylethanol; 2-Methyl-2-propanol; tert-C4H9OH; t-Butanol; tert-Butyl hydroxide; 2-Methylpropanol-2
2-Methylpropan-2-ol; Alcool butylique tertiaire; Butanol tertiaire; t-Butyl hydroxide; Methanol, trimethyl-
NCI-C55367; 2-Methyl n-propan-2-ol; Methyl-2 propanol-2; Tert.-butyl alcohol
Chemical formula: C4H10O
Molar mass: 74.123 g·mol−1
Appearance: Colorless solid
Odor: Camphorous
Density: 0.775 g/mL
Melting point: 25 to 26 °C; 77 to 79 °F; 298 to 299 K
CAS Number: 75-65-0
Beilstein Reference: 906698
CHEBI:45895
ChEMBL: ChEMBL16502
ChemSpider: 6146
DrugBank: DB03900
ECHA InfoCard: 100.000.809
EC Number: 200-889-7
Gmelin Reference: 1833
MeSH: tert-Butyl+Alcohol
PubChem CID: 6386
RTECS number: EO1925000
UNII: MD83SFE959
UN number: 1120
CompTox Dashboard (EPA): DTXSID8020204
What Is tert-Butyl alcohol?
t-Butyl Alcohol is a clear liquid with a camphor-like odor.
In cosmetics and personal care products, t-Butyl Alcohol is used in the formulation of perfumes, colognes, hair sprays, aftershave lotions, nail polish and shaving products.
Why is tert-Butyl alcohol used in cosmetics and personal care products?
t-Butyl Alcohol is used as a denaturant and a solvent.
Scientific Facts about tert-Butyl alcohol:
tert- or t-Butyl Alcohol, a tertiary alcohol, is used as an alcohol denaturant for a number of cosmetic and noncosmetic uses.
A tertiary alcohol means that the carbon that is bound to the hydroxyl group (-OH) is bound to three other carbon atoms.
Chemical Properties of tert-Butyl alcohol:
tert-butyl alcohol, (CH3)3COH, also known as tert-Butanol, is a white crystalline solid or colorless liquid (above 77 °F) with a camphor-like odor.
tert-Butyl alcohol is soluble in water and miscible with alcohol, ether, and other organic solvents (IPCS, 1987a).
tert-Butyl alcohol is highly flammable and easily ignited by heat, sparks, or flames; vapors may form explosive mixtures with air.
Fire and explosion may result from contact with oxidizing agents, strong mineral acids, or strong hydrochloric acid.
CAS Number: 75-65-0
Synonym: tert-Butanol, 2-Methylpropan-2-ol, Trimethyl carbinol, 2-Methyl-2-propanol
Occurrence/Use:
Solvent, ethanol denaturant, paint remover ingredient, and gasoline octane booster and oxygenate.
tert-Butyl alcohol is a chemical intermediate used to produce MTBE and ETBE by reaction with methanol and ethanol, and TBHP by reaction with hydrogen peroxide.
Synonym: tert-Butyl Alcohol, t-Butanol, tert-Butanol
Quality Specifications
Purity: 99.65% min
sec.-Butanol: 0.25% max
Water: 0.03% max
Bromine number (g/100g): 0.02 max
Acid number (mg KOH/g): 0.01 max
Color (APHA): 10 max
Physical Properties
Appearance: Colorless liquid with a Camphor odor, solidified at room temperature
Molecular Weight: 74.12
Relative Density: 0.781 - 0.785 (g/cm 3)
Melting Point: 25.5°C (77.9°F)
Boiling Point: 82.5°C (180.5°F)
Specific Heat (at 30°C): 2.97 kJ/kg K
Viscosity (at 30°C): 3.3 mPa s
In the United States, the most widely used ether‐based oxygenate, MTBE, was added to gasoline from approximately 1980 to 2006.
From the early 1990’s onwards, many urban areas of the United States were required to use fuel oxygenates.
MTBE and ethanol were most frequently used to conform to this federal requirement.
In other areas of the country, MTBE was also included in gasoline to increase the fuel octane rating.
MTBE‐containing gasoline is considered a potential source of TBA for the following reasons:
a.TBA as an oxygenate:
Beginning in 1979 and into the early 1980’s, and in a small proportion of the gasoline supply, TBA itself was sometimes added to gasoline as an octane‐enhancer, with methanol as a cosolvent.
b.TBA in fuel grade ether oxygenates:
As a byproduct of the manufacturing process, low concentrations of TBA (~2 wt%) were common in the “fuel grade” ether oxygenates such as MTBE.
c. TBA as a product of ether oxygenate biodegradation:
TBA is well‐established as a product of MTBE biodegradation processes catalyzed by microorganisms in the environment.
What are the properties of TBA in ground water and how do they compare to MTBE?
Like many other alcohols such as ethanol, TBA is fully miscible with water.
Consequently, TBA can rapidly dissolve out of gasoline and high dissolved concentrations of TBA can occur in gasoline‐impacted ground water.
In contrast, the aqueous solubility of MTBE is ~50g L‐1 while that of benzene is less than 2 g/L‐1.
TBA also has a low vapor pressure (~40 mm Hg @ 25o C) compared to MTBE (~250 mm Hg @ 25o C).
TBA also has a much lower Henry’s Law Constant than MTBE, so while MTBE can be volatilized from contaminated ground water using air stripping, TBA does not strip and remains in solution.
Neither MTBE nor TBA sorb strongly to organic matter which limits the remedial efficacy of activated carbon and also means that both compounds travel at the rate of ground water flow.
What are microorganisms and how can they impact contaminants like MTBE and TBA in ground water?
Boiling point: 82 to 83 °C; 179 to 181 °F; 355 to 356 K
Solubility in water: miscible
log P: 0.584
Vapor pressure: 4.1 kPa (at 20 °C)
Acidity (pKa): 16.54
Magnetic susceptibility (χ): 5.742×10−5 cm3/mol
Refractive index (nD): 1.387
Dipole moment: 1.31 D
What compounds do bacteria in ground water need to be active?
To grow and be active, bacteria require a carbon source (to generate new biomolecules or cells), an energy source known as an electron donor, and an electron acceptor.
Like many other bacteria that grow on gasoline components, bacteria that can grow on MTBE and TBA also use these compounds as both a carbon source and electron donor.
Some bacteria can use oxygen (O2) as an electron acceptor.
These organisms are called aerobes and these bacteria can only function and grow if oxygen is present in their immediate environment.
Many of the bacteria that can biodegrade MTBE and TBA are aerobes.
Many types of bacteria can also use compounds other than oxygen as an electron acceptor.
These organisms are called anaerobes.
Anaerobic electron acceptors include many compounds that can be present at in ground water such as nitrate, ferric iron, sulfate and others.
In ground water systems the type of electron acceptors that are present strongly impacts the type of biodegradation processes that can occur.
Both MTBE and TBA can be biodegraded under anaerobic conditions.
How are contaminants biodegraded?
To be able to grow on contaminants such as MTBE and TBA, bacteria have to breakdown (biodegrade) these compounds.
The biochemical mechanisms bacteria use to degrade contaminants is strongly impacted by the available electron acceptors.
The most significant differences in biodegradation processes are dictated by whether or not the process occurs under aerobic or anaerobic conditions.
To characterize biodegradation processes, microbiologists typically use pure cultures of microorganisms.
These cultures are pure as they only contain one type of microorganisms
To date, many pure cultures of microorganisms have been identified that biodegrade MTBE and TBA in the presence of oxygen.
Biodegradation of MTBE and TBA can also be enhanced in contaminated environments through the addition of oxygen to stimulate the activities of these types of organisms.
In contrast, no pure cultures of microorganisms have been identified that biodegrade MTBE or TBA in the absence of oxygen.
However, this lack of pure cultures does not mean that biodegradation of these compounds only occurs in the presence of oxygen.
Anaerobic biodegradation studies using a wide variety of environmental samples (ground water, sediments, aquifer solids and activated sludge) have demonstrated that MTBE, and to a lesser extent TBA, can biodegrade in the presence of all of the electron acceptors that support anaerobic microbial growth in ground water.
These include nitrate, ferrous iron, sulfate and carbon dioxide.
Our current understanding of MTBE and TBA biodegradation is very similar to what we know about benzene, another important gasoline‐derived ground water contaminant.
Numerous strains of aerobic benzene‐biodegrading bacteria have been characterized and aerobic biotreatment is widely recognized as an effective treatment option for this compound.
In contrast, and despite many years of research, very few pure cultures of anaerobic benzene‐degrading microorganisms have been identified.
Current evidence suggests that benzene, like many other contaminants, is biodegraded through the combined activities of diverse anaerobic bacteria operating as a microbial community.
Identification of individual organisms capable of catalyzing all of the activities required for anaerobic benzene biodegradation may therefore be unrealistic.
However, anaerobic benzene biodegradation frequently occurs in gasoline‐impacted environments and this process is recognized in monitored natural attenuation (MNA) protocols for gasoline‐impacted sites.
Synonym(s): 2-Methyl-2-propanol, tert-Butyl alcohol, Trimethyl carbinol
Linear Formula: (CH3)3COH
CAS Number: 75-65-0
Molecular Weight: 74.12
Beilstein/REAXYS Number: 906698
EC Number: 200-889-7
MDL number: MFCD00004464
PubChem Substance ID: 57650901
NACRES: NA.21
In recent years, small amphiphilic molecules have gained a lot of attention from the researchers because of their fascinating behavior.
For example, the molecule tert-butyl alcohol (TBA) does not favor the folded state of protein; whereas its isostere trimethylamine N-oxide (TMAO) stabilizes the native state.
Another amphiphilic molecule dimethyl sulfoxide acts as a protein stabilizer in an aqueous binary mixture below the mole fraction of 0.15.
After this concentration, an opposite effect has been observed.
Therefore, the structural features of different amphiphiles and their extent of interactions with the solvent molecules are very much important to predict their behavior.
Considering the two small organic molecules TBA and TMAO, both have the same hydrophobic composition (i.e., three methyl groups).
On the contrary, TBA contains a tertiary butyl group, and TMAO has an N-oxide moiety in their hydrophilic counterparts.
In spite of this small difference, the aqueous solution behavior of the two molecules is quite different.
Previous literature reports have suggested self-aggregation of TBA molecules in dilute aqueous solutions; however, TMAO does not exhibit a similar tendency.
It is reported that TMAO forms an aggregate with water by strong hydrogen bonding.
In a word, the solution behavior should depend on the type of aggregation (i.e., TBA–TBA or TMAO–water).
Quality Level: 100
grade: anhydrous
vapor density: 2.5 (vs air)
The invention applies to the technical field of preparation of isobutylene and provides a method for preparing isobutylene from tert-butyl alcohol.
According to the method, slurry is prepared from deionized water and a catalyst in a slurry mixer and is pumped into a catalytic distillation column and has a dehydration reaction with tert-butyl alcohol as the raw material
A material discharged from the bottom of the catalytic distillation column is a mixture of small amount of tert-butyl alcohol, water and the catalyst, the mixture is circulated back to the slurry mixer.
An overhead product is condensed by a condenser and enters a reflux tank, part of the overhead product flows back to the catalytic distillation column, part of the overhead product is pumped into a purification distillation column, and high-purity isobutylene id distilled out of the top of the purification distillation column.
On the basis, the method adopts slurry catalytic distillation, the efficiency of the catalyst is improved, catalytic elements are not needed to be manufactured, the catalytic distillation equipment is simplified, catalyst replacement without shutdown is realized, and the production efficiency is improved.
vapor pressure:
31 mmHg ( 20 °C)
44 mmHg ( 26 °C)
assay: ≥99.5%
form: solid or liquid
autoignition temp.: 896 °F
expl. lim.: 8 %
impurities: <0.005% water
evapn. residue: <0.0003%
refractive index: n20/D 1.387 (lit.)
pH: 7 (20 °C)
bp: 83 °C (lit.)
mp: 23-26 °C (lit.)
solubility: water: miscible
What are the characteristics of anaerobic MTBE biodegradation?
Gasoline contains many readily biodegradable compounds and when this mixture is introduced into the subsurface rapid biodegradation can occur and deplete oxygen and other available electron acceptors.
Consequently, it is important to understand the biodegradation process that impact MTBE and TBA under anaerobic conditions as these conditions are frequently encountered at gasoline‐impacted sites.
When MTBE biodegradation occurs under anaerobic conditions, TBA frequently accumulates as a byproduct.
As we currently do not have pure cultures of anaerobic MTBE‐degrading microorganisms, the biochemical reactions involved in this process have not been fully established.
However, there is strong evidence that CO2‐utilizing anaerobic microorganisms known as acetogens play an important role in this process.
Acetogens are a diverse group of widely distributed bacteria that generate acetate (CH3COOH) as a product of their biodegradation activities.
Based on what is known about the biodegradation of other ether‐containing compounds by acetogens, these organisms use the methoxy methyl group of MTBE as their electron donor and CO2 as their electron acceptor.
The carbon from the methyl group is incorporated into acetate and both acetate and TBA are excreted as byproducts.
Acetate excreted by acetogens can be biodegraded by other common soil microorganisms called methanogens that often grow under the same environmental conditions as acetogens.
Methanogens excrete methane (CH4) as the terminal product of their own distinctive metabolic activities.
A similar pathway of MTBE biodegradation to TBA may also occur with other anaerobic microorganisms.
density: 0.775 g/mL at 25 °C (lit.)
SMILES string: CC(C)(C)O
InChI: 1S/C4H10O/c1-4(2,3)5/h5H,1-3H3
InChI key: DKGAVHZHDRPRBM-UHFFFAOYSA-N
2-Propanol, 2-methyl-; tert-Butyl Alcohol; tert-Butanol; Ethanol, 1,1-Dimethyl-; Trimethylcarbinol; Trimethylmethanol
1,1-Dimethylethanol; 2-Methyl-2-propanol; tert-C4H9OH; t-Butanol; tert-Butyl hydroxide; 2-Methylpropanol-2
2-Methylpropan-2-ol; Alcool butylique tertiaire; Butanol tertiaire; t-Butyl hydroxide; Methanol, trimethyl-
NCI-C55367; 2-Methyl n-propan-2-ol; Methyl-2 propanol-2; t-Butyl alcohol; Terz-butanolo
CAS: 75-65-0
Formula: C₄H₁₀O
Synonyms: 2-methyl-2-propanol; trimethylcarbinol; TBA
We have investigated the effects of tert-butyl alcohol (TBA) on the structure and dynamics of water at the liquid–vapor interface.
The structure of interfacial water has been studied by calculating the structural correlations and vibrational sum frequency generation (VSFG) spectrum from molecular dynamics simulations.
It is found that the dangling peak of the VSFG spectrum of the air–water interface near ∼3700 cm–1 almost disappears in presence of TBA at the chosen concentration which means that the interfacial region is covered by the solute molecules.
The hydrogen-bonded peak in the VSFG spectrum is found to be red-shifted by ∼100 cm–1 as compared to that of pure the air–water interface despite the fact that the strength of hydrogen bonds in the interfacial region is found to be similar to that of the bulk.
This red shift in the VSFG spectrum is found to be a consequence of the cancellation of the nonlinear responses from “up-” and “down”-oriented O–H modes of water in that region.
The local structure around the interfacial water is found to be similar to that of bulk water where the oxygen of TBA provides an environment similar to the oxygen of water in the bulk.
However, the dynamical properties like the orientational relaxation and vibrational spectral diffusion are found to slow down when one moves from bulk toward the TBA layer at the surface.
The effects of intra- and inter-molecular coupling and third-order susceptibility on the VSFG spectrum are also discussed.
Remediation of tert-butyl alcohol (TBA) in subsurface waters should be taken into consideration at reformulated gasoline contaminated sites since it is a biodegradation intermediate of methyl tert-butyl ether (MTBE), ethyl tert-butyl ether (ETBE), and tert-butyl formate (TBF).
The effect of temperature on TBA biodegradation has not been not been published in the literature.
What is the fate of TBA under anaerobic conditions?
In MTBE‐degrading laboratory cultures the biodegradation of MTBE is often accompanied by a near stoichiometric accumulation of TBA.
In these cultures TBA is typically stable and does not undergo further biodegradation.
A substantially similar effect has been observed in field studies of MTBE biodegradation.
However, in the environment there is also evidence that TBA can often undergo further biodegradation.
Based on the time course of these reactions, it is likely that the further biodegradation of TBA is brought about by a separate group of microorganisms whose activities are only stimulated once sufficient TBA has accumulated to support their growth and activities.
As is the case with MTBE, no pure cultures of anaerobic TBA‐utilizing organisms are currently available.
However, laboratory studies with mixed cultures have indicated that TBA can be biodegraded under nitrate, iron– and sulfate‐reducing conditions.
CAS Number: 75-65-0
Formula: CH33COH
Density: 0.8 g/mL
Boiling and Freezing Point: 83°C, 25°C
Solubility: Water, miscible with Alcohol and Ether
Synonyms: tert-Butanol, 2-Methyl-2-propanol
Methyl tert-butyl ether (MTBE) is a contaminant of concern to groundwater resources due to its persistence in subsurface environments.
MTBE appears to be degraded readily in the presence of oxygen but is recalcitrant under the anaerobic conditions prevalent in the subsurface, and can be converted into the more toxic compound tert-butanol (TBA).
As ethanol is being promoted as a renewable fuel and a replacement for MTBE in gasoline formulations, its potential impact on the biodegradation of preexisting contaminants and on other components of petroleum must be examined.
The purpose of this study is to investigate the effect of ethanol release on existing MTBE plumes and the fate of TBA under sulfate-reducing conditions.
Our results suggest that TBA, MTBE and ethanol-induced methane concentrations are strong determinants of the composition of the indigenous microbial community that develops during MTBE transformation.
Some of the changes in microbial communities induced by ethanol may be long lasting, thus potentially altering the natural attenuation capacity of the impacted aquifer.
tert-Butanol is a crystalline solid below 25°C and a colorless, volatile liquid with a camphorlike odor above 25°C.
The odor threshold is 47 ppm.
tert-Butanol is used in perfumes, cosmetics, aerosol sprays, paint removers, and defoaming agents; industrially, it is used in production processes, separations, and cleaning and as a gasoline additive and dehydrating agent.
Analysis of air from recent space-shuttle flights showed that this alcohol is found in about 15% of the air samples at concentrations that sometimes exceed 1 mg/m3.
Synonyms: 2-methyl-2-propanol, tert-butyl alcohol, tertiary butanol, t-butanol
Formula: (CH3)3COH
CAS number: 75-65-0
Molecular weight: 74.1
Boiling point: 82°C
Melting point: 25°C
Specific gravity: 0.79
Vapor pressure: 42 mmHg at 25°C
Lower flammability limit: 2.4%
Solubility:
Soluble in water, miscible with ethanol and other organic solvents
Conversion factors:
1 ppm = 3.08 mg/m3
1 mg/m3 = 0.325 ppm
What are the characteristics of MTBE and TBA biodegradation under aerobicconditions?
Like many other ground water contaminants, both MTBE and TBA can be more rapidly biodegraded under aerobic conditions than anaerobic conditions.
As many aerobic MTBE‐ and TBA‐degrading microorganisms have been isolated and characterized, more is known about the biodegradation mechanisms and the organisms responsible for these activities than the equivalent anaerobic processes.
A number of aerobic bacteria have been isolated that can grow on MTBE and all of these organisms also have the ability to grow on TBA.
Conversely, there are examples of bacteria.
Despite this difference and to the extent this process has been analyzed, the pathway of TBA biodegradation appears to be very similar in all of these organisms.
A key feature of many aerobic biodegradation processes is that oxygen is introduced into the contaminant as an early part of the biodegradation process.
For examples, n‐alkanes are generally unreactive compounds.
The vast majority of aerobic n‐alkane biodegradation processes are initiated by bacteria thatuse diverse oxygenase enzymes to insert O atoms from O2 into these compounds.
This has the effect of “activating” the inert n‐alkanes by converting them into readily biodegradable alcohols.
The same is also true of MTBE and TBA.
Formula: C4H10O / (CH3)3COH
Molecular mass: 74.1
Boiling point: 83°C
Melting point: 25°C
Relative density (water = 1): 0.8
Solubility in water: miscible
Vapour pressure, kPa at 20°C: 4.1
Relative vapour density (air = 1): 2.6
Relative density of the vapour/air-mixture at 20°C (air = 1): 1.06
Flash point: 11°C c.c.
Auto-ignition temperature: 470°C
Explosive limits, vol% in air: 1.7-8.0
Octanol/water partition coefficient as log Pow: 0.3
The activation of these compounds by oxygenase enzymes is particularly important as both MTBE and TBA contain a branched hydrocarbon structure, the tertiary butyl group.
As a general rule, branched structures are more resistant to biodegradation than their straight‐chained hydrocarbon equivalent.
In the case of MTBE, the presence of an ether‐bonded methoxy group also contributes to the stability of this compound.
Current research indicates aerobic microorganisms consistently use oxygenase enzymes to initiate the degradation of both MTBE and TBA.
In the case of MTBE, an oxygen atom from O2 is first added onto the methoxy carbon in a reaction that generates an unstable intermediate.
This intermediate then decomposes to generate TBA.
A second oxygenase enzyme is then used to initiate the further biodegradation of TBA to intermediates that the active organisms can subsequently use as a carbon and energy source.
Since MTBE‐degrading organisms do not obtain significant amounts of energy from the initial conversion of MTBE to TBA, the organisms technically grow on TBA rather than MTBE.
So organisms that grow on MTBE rarely allow TBA to accumulate as it is rapidly consumed and converted to CO2.
Both MTBE and TBA can also be biodegraded by bacteria that grow on other compounds but cannot grow on either MTBE or TBA alone.
This process is called cometabolism.
Many research studies have shown alkane components of gasoline can support the growth of diverse bacterial strains that can cometabolically convert MTBE to TBA.
In some instances TBA can also be further biodegraded by these organisms although TBA is often excreted as a byproduct of MTBE cometabolism.
As aerobic TBA‐utilizing microorganisms are widely distributed in the environment, the accumulation of TBA as a result of a cometabolic conversion of MTBE to TBA can stimulate the growth and activity of these separate TBA‐utilizing microorganisms.
This is another example of how the metabolic activities of separate groups of microorganisms can be combined and can result in the full biodegradation of a contaminant to CO2.
The rapid biodegradation of both MTBE and TBA under aerobic conditions has been exploited in several in situ and ex‐situ bioremediation approaches for these compounds.
For example, the introduction of oxygen into the sub surface using biobarriers has been shown to be very effective for the treatment of large dissolved plumes of MTBE.
Likewise, various aerobic bioreactor configurations have been developed and commercialized for the ex‐situ treatment of MTBE and TBA.
Although less well studied, aerobic conditions can also be reasonably expected to promote the natural attenuation of both TBA and MTBE in contaminated ground water.
The dehydration of tert-butyl alcohol to water and isobutene was studied using an ion-exchange resin catalyst at temperatures between 60 and 90 °C.
A temperature-dependent equilibrium constant for the dehydration reaction was obtained that gave a reaction enthalpy of 26 kJ mol-1, in good agreement with values in the literature.
Measured data were used for kinetic modeling of the reaction.
The best model with physically meaningful parameters was of Langmuir−Hinshelwood type where isobutene does not adsorb on the catalyst.
The activation energy for the reaction in this case was 18 kJ mol-1.
What is Butyl alcohol?
Butyl alcohol (C4H9OH), also known as butanol, is a clear, colorless and flammable liquid used as an organic solvent.
Butyl alcohol has four isomers, n-butyl, isobutyl, secondary butyl, and tertiary butyl alcohol.
Common cosmetic and pharmaceutical uses for butanol include: cosmetics, such eye makeup, foundations, lipsticks, nail care products, personal hygiene products and shaving products; and use in drug manufacturing for antibiotics, hormones, and vitamins.
Other names
t-Butyl alcohol
tert-Butanol
t-Butanol
t-BuOH
Trimethyl carbinol
2-Methyl-2-propanol
2M2P
Alcool butylique tertiaire
t-BuOH
Methanol, trimethyl-
tertiary Butyl Alcohol
tert.-butanol
tert- butyl alcohol
t-butylalcohol
tertiary butanol
NCI-C55367
t-Butyl alchohol
tBuOH
tert-BuOH
UNII-MD83SFE959
tert-Butyl hydroxide
MFCD00004464
2-Methyl n-propan-2-ol
MD83SFE959
CHEBI:45895
tert-Butanol-d10
Arconol
tert-Butanol, ACS reagent
tert-Butyl alcohol, anhydrous
2-Methyl-2-propan(ol-d)
Caswell No. 124A
tert-Butanol, 99.5%, extra pure
tert Butanol
tert-Butanol, 99.5%, for analysis
Butanol tertiaire [French]
tert Butyl Alcohol
HSDB 50
TBU
2-Methylpropanol-2
Alcohol, tert-Butyl
CCRIS 4755
Alcool butylique tertiaire [French]
EINECS 200-889-7
BRN 0906698
terbutanol
tertbutanol
tertiarybutanol
ter-butanol
tert.butanol
t-Butylalkohol
t-butyl-alcohol
terbutyl alcohol
AI3-01288
tert -butanol
tertbutyl alcohol
tert. Butanol
t- butanol
HOtBu
ter-butyl alcohol
tert-buyl alcohol
tert-butyl-alcohol
tert.-butylalcohol
tert.butyl alcohol
Trimethyl-Methanol
tert-Butanol, AR
2methyl-2-propanol
tert. butyl alcohol
HOt-Bu
Tert.-butyl alcohol
tert-C4H9OH
2-methyl,2-propanol
PubChem3012
33500-15-1
Methyl-2 propanol-2
t-Bu-OH
1,1-dimethyl ethanol
tert-Butyl-d9 alcohol
2-methyl propan-2-ol
2-methyl-propan-2-ol
ACMC-209ozd
tert-Butanol HPLC grade
tert-Butanol ACS reagent
Ethanol, 1,1-Dimethyl-
2-methyl-2-propyl alcohol
EC 200-889-7
(CH3)3COH
4-01-00-01609 (Beilstein Handbook Reference)
HOC(CH3)3
CHEMBL16502
tert-Butyl alcohol reagent
DTXSID8020204
A838477
Q285790
J-510082
2-Methyl-2-propanol, Trimethylcarbinol, tert-Butanol
TERT-BUTYL-1,1,1-D3 ALCOHOL,98 ATOM % D
F0001-1901
tert-Butanol, puriss. p.a., ACS reagent, >=99.7% (GC)
UNII-WB09NY83YA component DKGAVHZHDRPRBM-UHFFFAOYSA-N
2-Methyl-2-propanol, tert-Butyl alcohol, Trimethyl carbinol
tert-Butanol, certified reference material, 5000 mug/mL in methanol
t-butyl alcohol
tert-Butanol
tert-Butyl alcohol
2-Methyl-2-propanol
2-Methylpropan-2-ol
75-65-0
t-Butanol
1,1-Dimethylethanol
Trimethylcarbinol
T-BUTYL ALCOHOL
t-Butyl hydroxide
Trimethyl methanol
2-Propanol, 2-methyl-
Tertiary-Butyl Alcohol
Trimethylmethanol
tert-butylalcohol
Butanol tertiaire
Trimethyl carbinol
Dimethylethanol
tertiary-Butanol
tert Butyl Alcohol
tert-Butyl Alcohol
tert-butyl alcohol, anhydrous
tert-butylalcohol
tertiary alcohol
TERTIARY BUTANOL
tertiary-Butanol
Trimethyl carbinol
(CH3)3C-OH
tert-Butanol [Wiki]
200-659-6 [EINECS]
200-889-7 [EINECS]
2-Methyl-2-propanol [ACD/IUPAC Name]
2-Methyl-2-propanol [German] [ACD/IUPAC Name]
2-Méthyl-2-propanol [French] [ACD/IUPAC Name]
2-Methylpropan-2-ol
2-Methyl-propan-2-ol
2-Methylpropan-2-olato
2-Propanol, 2-methyl- [ACD/Index Name]
75-65-0 [RN]
906698 [Beilstein]
Alcool butylique tertiaire [French]
Butanol tertiaire [French]
Methanol, trimethyl-
propan-2-ol, 2-methyl-
TBA
tBuOH [Formula]
T-BUTANOL
1,1,1,3,3,3-Hexadeuterio-2-(trideuteriomethyl)propan-2-ol
1,1,1-Trideuterio-2-methylpropan-2-ol
1,1-DIMETHYL ETHANOL
1,1-dimethylethanol
tert-butanol
tert-butyl alcohol
butyl alcohol tertiary
tert-butylalcohol
1,1-dimethyl ethanol
2-methyl propan-2-ol
2-methyl-2-propanol
2-methyl-propan-2-ol
2-methylpropan-2-ol
propan-2-ol, 2-methyl-
2-propanol, 2-methyl-
trimethyl carbinol
trimethyl methanol
trimethylcarbinol
trimethylmethanol
InChI=1S/C4H10O/c1-4(2,3)5/h5H,1-3H3
Methyl-2 propanol-2
methyl-2-propanol
MPD
MRD
tert-Butanol, for HPLC, >=99.5%
tert-Butanol, technical grade, 95.0%
tert-Butanol, ACS reagent, >=99.0%
25-65-0
BP-20656
Butyl Alcohol (tert)- Reagent Grade ACS
tert-Butanol 100 microg/mL in Acetonitrile
tert-Butanol, SAJ first grade, >=98.0%
B0706
FT-0688093
tert-Butanol, TEBOL(R) 99, >=99.3%
tert-Butanol, SAJ special grade, >=99.0%
2-Methyl n-propan-2-ol
2-Methylpropan-2-(2H)ol
2-Propan-1,1,1,3,3,3-d6-ol-d, 2-(methyl-d3)-
32149-57-8 [RN]
4-01-00-01609 (Beilstein Handbook Reference) [Beilstein]
937174-76-0 [RN]
Alcohol, tert-Butyl
Alcool butylique [French]
Arconol
Dimethylethanol
Ethanol, 1,1-Dimethyl-
Hemosty
pMethylolpropane
TBU
t-butyl alchohol
t-butyl hydroxide
t-Butylalkohol
tert-Butanol, >=99% (GC)
tert-Butanol, analytical standard
tert-Butanol, p.a., 99.0%
AMY11058
ZINC1680021
ANW-36647
STL282741
tert-Butanol, anhydrous, >=99.5%
AKOS009029221
DB03900
MCULE-2451492095
Tert- butyl alcohol
tert-Butanol 100 µg/mL in Acetonitrile
tert-Butanol 100 µg/mL in Methanol
tert-Butanol ACS reagent
tert-Butanol HPLC grade
tert-Butyl alcohol, 2-Methyl-2-propanol, Trimethylcarbinol
tert-Butyl Alcohol-OD
tert-butyl hydroxide
tert-C4H9OH
tertiary Butyl Alcohol
Trimethyl methanol
trimethylcarbinol
trimethylmethanol
Trimethyl-Methanol
WLN: Q4
叔丁醇
