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CAS NO:75-65-0
EC NO:200-889-7
T-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH).
T-Butyl alcohol is one of the four isomers of butanol.
T-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor.
T-Butyl alcohol is miscible with water, ethanol and diethyl ether.
Properties
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
Boiling point 82 to 83 °C; 179 to 181 °F; 355 to 356 K
Solubility in water miscible[2]
log P 0.584
Vapor pressure 4.1 kPa (at 20 °C)
Acidity (pKa) 16.54 [3]
Magnetic susceptibility (χ) 5.742×10−5 cm3/mol
Refractive index (nD) 1.387
Dipole moment 1.31 D
Natural occurrence
T-Butyl alcohol has been identified in beer and chickpeas.
T-Butyl alcohol is also found in cassava, which is used as a fermentation ingredient in certain alcoholic beverages.
Preparation
T-Butyl alcohol is derived commercially from isobutane as a coproduct of propylene oxide production.
T-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
T-Butyl alcohol is used as a solvent, ethanol denaturant, paint remover ingredient, and gasoline octane booster and oxygenate.
T-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.
T-Butyl alcohol is a tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2.
T-Butyl alcohol has a role as a human xenobiotic metabolite.
T-Butyl alcohol derives from a hydride of an isobutane.
T-Butyl alcohol is a colorless oily liquid with a sharp alcohol odor. Floats and mixes with water. Produces irritating vapor. Freezing point is 78°F.
USES
-For t-butyl alcohol (USEPA/OPP Pesticide Code: 001505) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses.
-The active ingredient is no longer contained in any registered products ... "cancelled.".
-The solvent sector is the major field of application. 2-Methyl-2-propanol is also used as an agent for introducing the tert-butyl group into organic compounds (e.g., tert-butylphenol for the preparation of oil-soluble resins and antioxidants, trinitro-tert-butyltoluene as artificial musk) and as a starting material for the preparation of peroxides (polymerization catalysts).
-Denaturant for ethanol, manufacture of flotation agents, flavors, perfumes; as organic solvent, in paint removers. Octane booster in gasoline.
Industry Uses
Fuels and fuel additives
Intermediates
Laboratory chemicals
Plasticizers
Processing aids, not otherwise listed
Solvents (for cleaning and degreasing)
Solvents (which become part of product formulation or mixture)
Consumer Uses
Fuels and related products
Laboratory Use
Other Commercial Manufacturing
Industry Processing Sectors
All other basic organic chemical manufacturing
All other chemical product and preparation manufacturing
All other petroleum and coal products manufacturing
Laboratory Use
Oil and gas drilling, extraction, and support activities
Petrochemical manufacturing
Plastics product manufacturing
General description
T-Butyl alcohol is a tertiary alcohol.
T-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.
Occurrence/Use
Solvent, ethanol denaturant, paint remover ingredient, and gasoline octane booster and oxygenate.
T-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.
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
T-Butyl alcohol is used as a solvent and ethanol denaturant.
T-Butyl alcohol is an active ingredient of paint remover.
T-Butyl alcohol acts as an intermediate in the production of methyl tertiary butyl ether and ethyl tertiary butyl ether by reaction with methanol and ethanol.
T-Butyl alcohol is also used in the preparation of tert-butyl chloride, tert-butyl hydroperoxide, isobutylene and methyl methacrylate.
T-Butyl alcohol serves as a fuel additive as well as a gasoline octane booster.
What is T-Butyl alcohol?
T-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH₃)₃COH.
T-Butyl alcohol is one of the four isomers of butanol.
T-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor.
Uses
Solvent, ethanol denaturant, paint remover ingredient, and gasoline octane booster and oxygenate.
T-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.
T-Butyl alcohol is a highly pure product obtained by hydrating isobutylene.
T-Butyl alcohol is used as raw material for pharmaceuticals and agricultural chemicals and as a special solvent or the like.
MAJOR USE: Stabilizer for chlorinated solvents, Raw material for organic peroxide and other organic syntheses, Solvent for watermiscible alkyd resin.
For HPLC and organic synthesis
High-purity, multipurpose solvents
High lot-to-lot consistency
Description
Colorless liquid or colorless or white crystals with a camphor-like odor.
Uses
Denaturant for ethanol, mfg flotation agents, flavors, perfumes.
T-Butyl alcohol is a clear liquid (or a colorless solid, depending on the ambient temperature) with a camphor-like odor.
T-Butyl alcohol is very soluble in water and miscible with ethanol and diethyl ether.
T-Butyl alcohol, or 2-methyl-2-propanol, is the simplest tertiary alcohol.
T-Butyl alcohol is one of the four isomers of butanol.
tert-Butanol is a clear liquid with a camphor-like odor.
T-Butyl alcohol is well soluble in water and miscible with ethanol and diethyl ether.
T-Butyl alcohol is unique among the isomers of butanol because it tends to be a solid at room temperature, with a melting point slightly above 25 degrees Celsius.
Applications
T-Butyl alcohol is used as a solvent, as a denaturant for ethanol, as an ingredient in paint removers, as an octane booster for gasoline, as an oxygenate gasoline additive, and as an intermediate in the synthesis of other chemical commodities such as flavors and perfumes.
Preparation
T-Butyl alcohol can be manufactured industrially by the catalytic hydration of isobutylene.
Chemistry
As a tertiary alcohol, T-Butyl alcohol is more stable to oxidation and less reactive than the other isomers of butanol.
When T-Butyl alcohol is deprotonated with a strong base, the product is an alkoxide anion. In this case, it is tert-butoxide. For example, when tert-butanol is deprotonated with sodium hydride, the resultant is sodium tert-butoxide.
NaH + tBuOH → tBuO−Na+ + H2
The tert-butoxide species is itself useful as a strong, non-nucleophilic base in organic chemistry.
T-Butyl alcohol is able to abstract acidic protons from the substrate molecule readily, but its steric bulk inhibits the group from participating in nucleophilic addition, such as in a Williamson ether synthesis or an SN2 reaction.
Conversion to alkyl halide
T-Butyl alcohol (also tert-butyl alcohol) reacts with hydrogen chloride to form tert-butyl chloride and water via an SN1 mechanism.
Chemical Properties
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 (IPCS, 1987a; NIOSH, 2005).
T-Butyl alcohol is soluble in water and miscible with alcohol, ether, and other organic solvents (IPCS, 1987a).
T-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 (NIOSH,1992).
T-Butyl alcohol 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.
T-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).
T-Butyl alcohol 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 (HSDB, 2007).
T-Butyl alcohol is used in coatings on metal and paperboard food containers (Cal/EPA, 1999) and industrial cleaning compounds, and can be used for chemical extraction in pharmaceutical applications (HSDB, 2007).
Physical properties
T-Butyl alcohol 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 (1974). In a later study, Nagata and Takeuchi (1990) reported an odor threshold concentration 220 ppbv.
Uses
T-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.
Uses
T-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.
Uses
Plastics, lacquers, cellulose esters, fruit essences, perfumes, and chemical intermediates; additive to unleaded gasoline
Production Methods
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
T-Butyl alcohol is a tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2.
T-Butyl alcohol has a role as a human xenobiotic metabolite.
T-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.
Together with heat, tert-butyl alcohol is used to generate reactive palladium (0) in this reaction. Generally, tert-butyl alcohol is used as a common solvent. As a tertiary alcohol, tert-butyl alcohol is more stable to oxidation.
T-Butyl alcohols conjugate base, tert-butoxide is a strong base. Since it is bulky, tert-butoxide normally does not participate in nucleophilic substitution, such as in a Williamson ether synthesis or an SN2 reaction.
About this substance
Helpful information
T-Butyl alcohol is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 000 to < 10 000 000 tonnes per annum.
T-Butyl alcohol is used by consumers, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses
T-Butyl alcohol is used in the following products: coating products, washing & cleaning products and fillers, putties, plasters, modelling clay.
Other release to the environment of T-Butyl alcohol is likely to occur from: outdoor use and indoor use as processing aid.
Article service life
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers
T-Butyl alcohol is used in the following products: coating products, washing & cleaning products and laboratory chemicals.
T-Butyl alcohol is used in the following areas: scientific research and development.
Other release to the environment of T-Butyl alcohol is likely to occur from: indoor use as processing aid and outdoor use.
Formulation or re-packing
T-Butyl alcohol is used in the following products: coating products, washing & cleaning products, laboratory chemicals and pharmaceuticals.
Release to the environment of T-Butyl alcohol can occur from industrial use: formulation of mixtures.
Uses at industrial sites
T-Butyl alcohol is used in the following products: coating products, washing & cleaning products, laboratory chemicals and pharmaceuticals.
T-Butyl alcohol is used in the following areas: formulation of mixtures and/or re-packaging.
T-Butyl alcohol is used for the manufacture of: chemicals.
Release to the environment of T-Butyl alcohol 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.
Manufacture
Release to the environment of T-Butyl alcohol can occur from industrial use: manufacturing of the substance and as an intermediate step in further manufacturing of another substance (use of intermediates).
T-Butyl alcohol is used as a solvent and an ethanol denaturant.
T-Butyl alcohol is an active ingredient paint remover.
T-Butyl alcohol acts as an intermediate in the production of methyl tertiary butyl ether and ethyl tertiary butyl ether by reaction with methanol and ethanol.
T-Butyl alcohol is also used in the preparation of tert-butyl chloride, tert-butyl hydroperoxide, isobutylene and methyl methacrylate.
T-Butyl alcohol serves as a fuel additive as well as a gasoline octane booster.
T-Butyl alcohol is used in industrial synthesis, as a dehydrating agent, as a chemical intermediate and solvent in pharmaceutical manufacture, denaturant for ethanol and antiknock agent.
T-Butyl alcohol is our low-cost alternative to high-purity qualities.
T-Butyl alcohol is used as an organic solvent.
T-Butyl alcohol is also used in the synthesis of proteosome inhibitors that are quite potent.
IUPAC names
2-Methyl-2-propanol
2-methyl-2-propanol
2-Methyl-propan-2-ol
2-methyl-propan-2-ol
2-Methylpropan-2-ol
2-methylpropan-2-ol
2-methylpropan-2-ol
2-methylpropan-2-ol tert-butyl alcohol
2-Propanol, 2-methyl-
2-Propanol, 2-methyl- (9CI)
t-butanol
t-Butanol
t-Butyl alcohol
TBA
TERT-BUTANOL
tert-Butanol
TERT-BUTYL ALCOHOL
tert-Butyl alcohol
tert-butyl alcohol
Tert. Butanol
Tert.-Butanol
Tertiary butyl alcohol (TBA)
tertiary butyl alcohol, tert-butyl alcohol and tert-Butanol
SYNONYMS:
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
t-butyl alcohol
tert Butyl Alcohol
tert-Butyl Alcohol
tert-butyl alcohol, anhydrous
tert-butylalcohol
tertiary alcohol
TERTIARY BUTANOL
tertiary-Butanol
Trimethyl carbinol
