From Wikipedia, the free encyclopedia
tert -Butyl alcohol
Skeletal formula of tert -butyl alcohol
Ball and stick model of tert -butyl alcohol
Names
Preferred IUPAC name
Other names
t -Butyl alcoholtert -Butanolt -Butanolt -BuOHTrimethyl carbinol
[1] 2-Methyl-2-propanol 2M2P
Identifiers
906698
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
100.000.809
EC Number
1833
MeSH
tert-Butyl+Alcohol
RTECS number
UNII
UN number
1120
InChI=1S/C4H10O/c1-4(2,3)5/h5H,1-3H3
Y Key: DKGAVHZHDRPRBM-UHFFFAOYSA-N
Y
Properties
C 4 H 10 O
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
miscible
[2]
log P
0.584
Vapor pressure
4.1 kPa (at 20 °C)
Acidity (pK a )
16.54
[3]
5.742× 10−5 cm3 /mol
1.387
1.31 D
Thermochemistry
215.37 J K−1 mol−1
189.5 J K−1 mol−1
−360.04 to −358.36 kJ mol−1
−2.64479 to −2.64321 MJ mol−1
Hazards
GHS labelling :
Danger
H225 ,
H319 ,
H332 ,
H335
P210 ,
P261 ,
P305+P351+P338
NFPA 704 (fire 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):
3559 mg/kg (rabbit, oral) 3500 mg/kg (rat, oral)
[4]
NIOSH (US health exposure limits):
TWA 100 ppm (300 mg/m3 )
[1]
TWA 100 ppm (300 mg/m3 ) ST 150 ppm (450 mg/m3 )
[1]
1600 ppm
[1]
Safety data sheet (SDS)
inchem.org
Related compounds
2-Butanol
n -Butanol
Isobutanol
Related compounds
2-Methyl-2-butanol
Trimethylsilanol
Nonafluoro-tert-butyl alcohol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
tert -Butyl alcohol is the simplest
tertiary alcohol , with a
formula of (CH3 )3 COH (sometimes
represented as t -BuOH). Its
isomers are
1-butanol ,
isobutanol , and
butan-2-ol . 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 .
Natural occurrence
tert -Butyl alcohol has been identified in
beer and
chickpeas .
[5] It is also found in
cassava ,
[6] which is used as a fermentation ingredient in certain
alcoholic beverages .
Preparation
tert -Butyl alcohol is derived commercially from
isobutane as a coproduct 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 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 (K2 CO3 ),
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.
[7]
Applications
tert -Butyl alcohol 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 -butyl alcohol is more resistant to oxidation than the other isomers of butanol.
tert -Butyl alcohol 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.
[8]
K + t -BuOH → t -BuO− K+ + 1 / 2 H2
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
SN 2 reaction.
tert -Butyl alcohol reacts with
hydrogen chloride to form
tert -butyl chloride .
O-Chlorination of tert-butyl alcohol with hypochlorous acid to give
tert-butyl hypochlorite :
[9]
(CH3 )3 COH + HOCl → (CH3 )3 COCl + H2 O
Pharmacology and toxicology
There is limited data on the pharmacology and toxicology of tert-butanol in humans and other animals.
[10] 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.
References
^
a
b
c
d NIOSH Pocket Guide to Chemical Hazards.
"#0078" .
National Institute for Occupational Safety and Health (NIOSH).
^
"ICSC 0114 – tert -Butanol" . Inchem.org . Retrieved 29 March 2018 .
^ Reeve, W.; Erikson, C. M.; Aluotto, P. F. (1979).
"tert-Butyl alcohol" . Can. J. Chem . 57 : 2747.
doi :
10.1139/v79-444 .
^
"tert-Butyl alcohol" . Immediately Dangerous to Life or Health Concentrations (IDLH) .
National Institute for Occupational Safety and Health (NIOSH).
^
"t -Butyl Alcohol" . National Library of Medicine HSDB Database . National Institute for Health. Retrieved 29 March 2018 .
^
"Archived copy" (PDF) . Archived from
the original (PDF) on 2016-03-04. Retrieved 2013-03-05 . {{
cite web }}
: CS1 maint: archived copy as title (
link )
^ Perrin, D. D.; Armarego, W. L. F. (1988).
Purification of Laboratory Chemicals (3rd ed.). Pergamon Press.
ISBN
9780080347141 .
^ Johnson, W. S.; Schneider, W. P. (1950). "β-Carbethoxy-γ,γ-diphenylvinylacetic acid".
Organic Syntheses . 30 : 18.
doi :
10.15227/orgsyn.030.0018 .
^ Mintz, H. M.; Walling, C. (1969). "t-Butyl Hypochlorite". Org. Synth . 49 : 9.
doi :
10.15227/orgsyn.049.0009 .
^ Douglas McGregor (2010). "Tertiary-Butanol: a toxicological review".
Critical Reviews in Toxicology . 40 (8): 697–727.
doi :
10.3109/10408444.2010.494249 .
PMID
20722584 .
S2CID
26041562 .
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