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Tert-butyl alcohol

tert-Butyl alcohol
Skeletal formula of tert-butanol
Ball and stick model of tert-butanol
Sample of partially crystalised tert-butanol
Names
Preferred IUPAC name
2-Methylpropan-2-ol
Other names
tert-Butyl alcohol
tert-Butanol
Trimethyl carbinol,
2-Methyl-2-propanol
2M2P
Identifiers
75-65-0 YesY
3D model (Jmol) Interactive image
906698
ChEBI CHEBI:45895 YesY
ChEMBL ChEMBL16502 YesY
ChemSpider 6146 YesY
DrugBank DB03900 YesY
ECHA InfoCard 100.000.809
EC Number 200-889-7
1833
MeSH tert-Butyl+Alcohol
PubChem 6386
RTECS number EO1925000
UNII MD83SFE959 YesY
UN number 1120
Properties
C4H10O
Molar mass 74.12 g·mol−1
Appearance Colorless liquid
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
miscible
log P 0.584
Vapor pressure 4.1 kPa (at 20 °C)
Acidity (pKa) 16.54
-57.42·10−6 cm3/mol
1.387
Thermochemistry
215.37 J K−1 mol−1
189.5 J K−1 mol−1
−360.04–−358.36 kJ mol−1
−2.64479–−2.64321 MJ mol−1
Hazards
Safety data sheet inchem.org
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H225, H319, H332, H335
P210, P261, P305+351+338
Highly Flammable F Harmful Xn
R-phrases R11, R20, R36/37
S-phrases (S2), S9, S16, S46
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 11 °C (52 °F; 284 K)
480 °C (896 °F; 753 K)
Explosive limits 2.4–8.0%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
3559 mg/kg (rabbit, oral)
3500 mg/kg (rat, oral)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 100 ppm (300 mg/m3)
REL (Recommended)
TWA 100 ppm (300 mg/m3) ST 150 ppm (450 mg/m3)
IDLH (Immediate danger)
1600 ppm
Related compounds
Related butanols
2-Butanol

n-Butanol
Isobutanol

Related compounds
2-Methyl-2-butanol
Trimethylsilanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

n-Butanol
Isobutanol

tert-Butyl alcohol (TBA), also called tert-butanol, is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). It 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. It is miscible with water, ethanol and diethyl ether.

t-Butyl alcohol has been identified in beer and chickpeas. It is also found in cassava which is used as fermentation ingredient in certain alcoholic beverages.

tert-Butyl alcohol is derived commercially from isobutane as a co-product of propylene oxide production. It can also be produced by the catalytic hydration of isobutylene, or by a Grignard reaction between acetone and methylmagnesium chloride.

Purification can not 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 CaO, K2CO3, CaSO4, or MgSO4, followed by fractional distillation. Anhydrous t-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 4A MO sieves, aluminum tert-butylate, CaH2, or fractional crystallization under inert atmosphere.


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