tert-Butyl alcohol

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tert-Butyl alcohol
Skeletal formula of tert-butyl alcohol
Skeletal formula of tert-butyl alcohol
Ball and stick model of tert-butyl alcohol
Ball and stick model of tert-butyl alcohol
Sample of partially crystallized tert-butyl alcohol
Names
Preferred IUPAC name
2-Methylpropan-2-ol
Other names
  • t-Butyl alcohol
  • tert-Butanol
  • t-Butanol
  • t-BuOH
  • Trimethyl carbinol[1]
  • 2-Methyl-2-propanol
  • 2M2P
Identifiers
3D model (
JSmol
)
906698
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.000.809 Edit this at Wikidata
EC Number
  • 200-889-7
1833
MeSH tert-Butyl+Alcohol
RTECS number
  • EO1925000
UNII
UN number 1120
  • InChI=1S/C4H10O/c1-4(2,3)5/h5H,1-3H3 checkY
    Key: DKGAVHZHDRPRBM-UHFFFAOYSA-N checkY
  • CC(C)(C)O
Properties
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
miscible[2]
log P 0.584
Vapor pressure 4.1 kPa (at 20 °C)
Acidity (pKa) 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
Std enthalpy of
formation
(ΔfH⦵298)
 −360.04 to −358.36 kJ mol−1
Std enthalpy of
combustion
(ΔcH⦵298)
 −2.64479 to −2.64321 MJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark
Danger
H225, H319, H332, H335
P210, P261, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
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):
PEL (Permissible)
 TWA 100 ppm (300 mg/m3)[1]
REL (Recommended)
 TWA 100 ppm (300 mg/m3) ST 150 ppm (450 mg/m3)[1]
IDLH
(Immediate danger)
 1600 ppm[1]
Safety data sheet (SDS) inchem.org
Related compounds
Related butanols
 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).
checkY verify (what is checkY☒N ?)

tert-Butyl alcohol is the simplest

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

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

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-

SN2
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)3COH + HOCl → (CH3)3COCl + H2O

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

  1. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0078". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ "ICSC 0114 – tert-Butanol". Inchem.org. Retrieved 29 March 2018.
  3. doi:10.1139/v79-444
    .
  4. ^ "tert-Butyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ "t-Butyl Alcohol". National Library of Medicine HSDB Database. National Institute for Health. Retrieved 29 March 2018.
  6. ^ "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)
  7. ISBN 9780080347141
    .
  8. doi:10.15227/orgsyn.030.0018
    .
  9. doi:10.15227/orgsyn.049.0009
    .
  10. S2CID 26041562
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Tert-Butyl_alcohol&oldid=1210834003"