TERT-BUTANOL

CAS Number: 75-65-0
EC Number :200-889-7
IUPAC name: 2-Methylpropan-2-ol
Chemical formula: C4H10O

Tert-Butanol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH).
Tert-Butyl's isomers are 1-butanol, isobutanol, and butan-2-ol.
Tert-Butanol is a colorless solid, which melts near room temperature and has a camphor-like odor.
Tert-Butyl is miscible with water, ethanol and diethyl ether.

Natural occurrence
Tert-Butanol has been identified in beer and chickpeas.
It is also found in cassava, which is used as a fermentation ingredient in certain alcoholic beverages.

Preparation
Tert-Butanol is derived commercially from isobutane as a coproduct of propylene oxide production.
Tert-Butanol 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-Butanol 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
Tert-Butanol is used as a solvent, ethanol denaturant, paint remover ingredient, and gasoline octane booster and oxygenate.
It 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.

Reactions
As a tertiary alcohol, Tert-Butanol is more resistant to oxidation than the other isomers of butanol.

Tert-Butanol is deprotonated with a strong base to give the alkoxide. Particularly common is potassium tert-butoxide, which is prepared by treating tert-butanol with potassium metal.

The Tert-butoxide is a strong, non-nucleophilic base in organic chemistry.
It readily abstracts acidic protons from substrates, but its steric bulk inhibits the group from participating in nucleophilic substitution, such as in a Williamson ether synthesis or an SN2 reaction.

Tert-Butanol reacts with hydrogen chloride to form tert-butyl chloride.

Pharmacology and toxicology
There is limited data on the pharmacology and toxicology of tert-butanol in humans and other animals.
Human exposure may occur due to fuel oxygenate metabolism.
Tert-butanol is poorly absorbed through skin but rapidly absorbed if inhaled or ingested.
Tert-butanol is irritating to skin or eyes. Toxicity of single doses is usually low but high doses can produce a sedative or anesthetic effect.

Consumer Uses of Tert-Butanol:
Tert-Butanol is used in the following products: coating products, washing & cleaning products and fillers, putties, plasters, modelling clay.
Other release to the environment of Tert-Butanol is likely to occur from: outdoor use and indoor use as processing aid.

Widespread uses by professional workers
Tert-Butanol is used in the following products: coating products, washing & cleaning products and laboratory chemicals. Tert-Butanol is used in the following areas: scientific research and development. Other release to the environment of Tert-Butanol is likely to occur from: indoor use as processing aid and outdoor use.

Formulation or re-packing of Tert-Butanol:
Tert-Butanol is used in the following products: coating products, washing & cleaning products, laboratory chemicals and pharmaceuticals.
Release to the environment of Tert-Butanol can occur from industrial use: formulation of mixtures.

Uses at industrial sites of Tert-Butanol:
Tert-Butanol is used in the following products: coating products, washing & cleaning products, laboratory chemicals and pharmaceuticals.
Tert-Butanol is used in the following areas: formulation of mixtures and/or re-packaging.
Tert-Butanol is used for the manufacture of: chemicals.

Release to the environment of Tert-Butanol can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates), manufacturing of the substance and as processing aid.

Molar mass: 74.123 g
Appearance: Colorless solid
Odor: Camphorous
Density: 0.775 g/mL

Melting point: 25 to 26 °C
Boiling point: 82 to 83 °C
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

XLogP3-AA: 0.5
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0

Exact Mass: 74.073164938
Monoisotopic Mass: 74.073164938
Topological Polar Surface Area: 20.2 Ų
Heavy Atom Count: 5

Complexity: 25.1
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0

Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Tert-Butanol is a tertiary alcohol.
Tert-Butanol 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 Tert-Butanol in the presence of 12-tungstophosphoric acid supported on zirconia (TPA/ZrO2) catalyst.
The interaction behavior of Tert-Butanol on the Si (001)-(2×1) surface has been assessed by using the ab-initio density functional theory (DFT) based on pseudopotential approach.

Tert-Butanol (TBA) is used as a solvent; as a denaturant for ethanol and several other alcohols; in the manufacture of flotation agents, fruit essences, and perfumes; as an octane booster in gasoline; as a dehydrating agent; and as a chemical intermediate in the manufacture of methyl methacrylate.

Tert-Butanol's production for industrial uses may result in its direct release to the environment through various waste streams.
Tert-Butanol is also a likely degradation product of methyl tert-butyl ether (MTBE). Probable routes of human exposure to Tert-Butanol include inhalation, ingestion, and skin or eye contact.

Tert-Butanol is used as a solvent and ethanol denaturant.
Tert-Butanol is an active ingredient of paint remover.
Tert-Butanol acts as an intermediate in the production of methyl tertiary butyl ether and ethyl tertiary butyl ether by reaction with methanol and ethanol.
Tert-Butanol is also used in the preparation of tert-butyl chloride, tert-butyl hydroperoxide, isobutylene and methyl methacrylate.
Tert-Butanol serves as a fuel additive as well as a gasoline octane booster.

Demand for tert-butanol as a solvent in paint removers, cosmetics, pharmaceuticals, and other industries is increasing across the globe.
Excellent solvating characteristics of tertiary butanol are projected to drive the demand for tert-butanol and consequently, propel the market during the forecast period.
Tert-butanol is miscible with several solvents, also with water, which makes it ideal for numerous industrial applications.

Increase in usage of tert-butanol as a potential freeze-drying agent in the manufacturing of pharmaceutical compounds is expected to fuel its demand in the next few years.
However, rise in the availability of substitute products with bio-solvents and other oxo-alcohols is anticipated to restrain the market during the forecast period.
Therefore, companies, policymakers, visionaries, and end-users need to work together to increase growth opportunities in the global tert-butanol market.

Tert-butanol, also known as tertiary butyl alcohol (TBA), is one of the four isomers of butanol.
Tert-butanol is the simplest alcohol with a tertiary carbon atom.
Tert-butanol is naturally found in chickpeas and cassava (a fermentation ingredient for some alcoholic beverages).
Tert-butanol is commercially produced as a coproduct from isobutane during the manufacture of propylene oxide.

Majority of tertiary butanol is consumed as a chemical intermediate for various products.
Moreover, tert butanol cas is largely used as a solvent in various applications.
Tert-butanol is also employed as a paint remover ingredient, alcohol denaturant, etc.
Rise in demand for tert-butanol in the automotive industry is expected to boost the tert-butanol market size during the forecast period.

Tert-butanol is used as a solvent or co-solvent in paints, coatings, inks, and adhesives.
Additionally, it is used in varnishes, resins, gums, dyes, camphor, vegetable oils, fats, waxes,
rubbers, and alkaloids.
The global building & construction industry is expanding significantly across the globe, typically in expanding economies such as China, India, etc., due to rapid urbanization and industrialization.

Demand for tert-butanol in Asia Pacific is expected to rise significantly during the forecast period, owing to growth in the construction sector in the region, which comprises commercial establishments, public infrastructure and utilities, etc.

The global automotive industry has expanded significantly in the last few years in terms of manufacturing processes, materials, and geometries in order to meet the increase in requirements of consumers in terms of mileage and emissions.
Perfluoro-tert-butyl alcohol is used in the production of SO2-based electrolytes for rechargeable battery cells with improved stability for electric automotive applications.

Asia Pacific is rapidly becoming the global automotive hub for the last few years, primarily due to rise in consumer demand for vehicles.
Thus, increase in demand for tert-butanol in the automotive industry is likely to boost the global market during the forecast period.

Tert-butanol can be utilized as a denaturant in the production of ethyl alcohol.
Denatured alcohol is a form of ethanol and is also known as methylated spirit.
Ethyl alcohol is denatured by using certain denaturants or additives such as methanol, benzol, ether, and perfluoro-tert-butanol.

These additives make ethanol a poisonous liquid, with poor odor and taste.
This, in turn, makes it unsuitable for human consumption.
Rise in inclination of manufacturers toward better denaturant alternatives for denatured alcohol, such as isopropanol and tert-butanol, is expected to drive the global tert-butanol market during the
forecast period.

Tert-butanol is an excellent solvent and has high oxidation stability.
Increase in demand for effective chemical agents for alcohol denaturing is fueling market
demand for tert-butanol across the globe.

Increase in stringency of regulatory norms by governments of different countries across the globe to use denatured alcohol in gasoline blending is likely to propel the market during the forecast period.
Under the Renewable Fuel Standard (RFS), the Federal Government of the U.S. has mandated the use of renewable fuels, which is driving the use of domestic ethanol in the country.
Increase in applications of denatured alcohol in medical disinfectant, cosmetics, specimen preservation, sanding, fuel, pest control, etc., is anticipated to drive the global tert-butanol market in the next few years.

Tert-butanol, or TBA for short, is a pure C4 alcohol.
Tert-butanol is used as a high-purity, high-quality intermediate in the production of organic peroxides and antioxidants, and as a reaction component and solvent in the manufacture of fine chemicals and pharmaceuticals.
In addition, Tert-butanol is also used as an intermediate in the production of crop protection products and as a denaturant for cosmetic alcohols.

Tert-Butanol (CH3)3COH is a white crystalline solid or colorless liquid with a camphor-like odor.
Tert-Butanol is soluble in water and miscible with alcohol, ether, and other organic solvents.
Tert-Butanol 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.

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.
It 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, it also is used to create artificial musk, fruit essences, and perfume.
Tert-Butanol 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-Butanol 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.

Other names:
tert-Butanol
tert-Butyl alcohol
2-Methyl-2-propanol
2-Methylpropan-2-ol
75-65-0
t-Butanol
T-BUTYL ALCOHOL
1,1-Dimethylethanol
Trimethylcarbinol
t-Butyl hydroxide
Trimethyl carbinol
Trimethyl methanol
Tertiary-Butyl Alcohol
Trimethylmethanol
tert-butylalcohol
2-Propanol, 2-methyl-
Butanol tertiaire
Dimethylethanol
tertiary butanol
tertiary-Butanol
Alcool butylique tertiaire
tert- butyl alcohol
Methanol, trimethyl-
tertiary Butyl Alcohol
tert.-butanol
t-BuOH
NCI-C55367
t-Butyl alchohol
tert-BuOH
tert-Butyl hydroxide
2-Methyl n-propan-2-ol
MD83SFE959
CHEBI:45895
MFCD00004464
Arconol
25-65-0
Caswell No. 124A
t-butylalcohol
tert Butanol
tBuOH
tert Butyl Alcohol
HSDB 50
TBU
2-Methylpropanol-2
Alcohol, tert-Butyl
CCRIS 4755
EINECS 200-889-7
BRN 0906698
terbutanol
tertbutanol
tertiarybutanol
UNII-MD83SFE959
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
2methyl-2-propanol
tert. butyl alcohol
HOt-Bu
Tert.-butyl alcohol
tert-C4H9OH
2-methyl,2-propanol
Methyl-2 propanol-2
t-Bu-OH
1,1-dimethyl ethanol
2-methyl propan-2-ol
2-methyl-propan-2-ol
Ethanol, 1,1-Dimethyl-
2-methyl-2-propyl alcohol
EC 200-889-7
(CH3)3COH
HOC(CH3)3
CHEMBL16502
DTXSID8020204
AMY11058
ZINC1680021
STL282741
AKOS009029221
DB03900
BP-20656
B0706
FT-0688093
EN300-19307
C21389
A838477
Q285790
J-510082
F0001-1901