tert-Butyl alcohol

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tert-Butyl alcohol
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Names
Preferred IUPAC name
2-Methylpropan-2-ol
Other names
Identifiers
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3D model (JSmol)
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Abbreviations Me3COH
t-BuOH
tBuOH
tBuOH
906698
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EC Number Page Template:Plainlist/styles.css has no content.
1833
MeSH tert-Butyl+Alcohol
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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[1]
Solubility Miscible with ethanol and diethyl ether
log P 0.584
Vapor pressure 4.1 kPa (at 20 °C)
Acidity (pKa) 16.54[2]
5.742×10−5 cm3/mol
1.387
1.31 D
Thermochemistry
215.37 J/(K·mol)
189.5 J/(K·mol)
−360.04 to −358.36 kJ/mol
−2.64479 to −2.64321 MJ/mol
Hazards
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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)[3]
REL (Recommended)
 TWA 100 ppm (300 mg/m3) ST 150 ppm (450 mg/m3)[3]
IDLH (Immediate danger)
 1600 ppm[3]
Safety data sheet (SDS) inchem.org
Related compounds
Related butanols
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Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of Page Module:Chem2/styles.css has no content.(CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and 2-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.

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 (Page Module:Chem2/styles.css has no content.K2CO3), calcium sulfate (Page Module:Chem2/styles.css has no content.CaSO4), or magnesium sulfate (Page Module:Chem2/styles.css has no content.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 (Page Module:Chem2/styles.css has no content.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

Unlike other isomers of butanol, tert-butyl alcohol, as a tertiary alcohol, has no hydrogen atom next to hydroxy-group, which makes it resistant to oxidation to carbonyl compounds.

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]

Page Module:Chem2/styles.css has no content.2 K + 2 (CH3)3COH → 2 (CH3)3CO−K+ + 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 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]

Page Module:Chem2/styles.css has no content.(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 of tert-butyl alcohol can produce a sedative or anesthetic effect.

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content."ICSC 0114 – tert-Butanol". Inchem.org. Retrieved 29 March 2018.
  2. ^ Page Module:Citation/CS1/styles.css has no content.Reeve, W.; Erikson, C. M.; Aluotto, P. F. (1979). "tert-Butyl alcohol". Can. J. Chem. 57: 2747. doi:10.1139/v79-444.
  3. ^ a b c Page Module:Citation/CS1/styles.css has no content.NIOSH Pocket Guide to Chemical Hazards. "#0078". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ Page Module:Citation/CS1/styles.css has no content."tert-Butyl alcohol". Immediately Dangerous to Life or Health Concentrations. National Institute for Occupational Safety and Health.
  5. ^ Page Module:Citation/CS1/styles.css has no content."t-Butyl Alcohol". National Library of Medicine HSDB Database. National Institute for Health. Archived from the original on April 12, 2017. Retrieved 29 March 2018.
  6. ^ Page Module:Citation/CS1/styles.css has no content."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. ^ Page Module:Citation/CS1/styles.css has no content.Perrin, D. D.; Armarego, W. L. F. (1988). Purification of Laboratory Chemicals (3rd ed.). Pergamon Press. ISBN 9780080347141.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Johnson, W. S.; Schneider, W. P. (1950). "β-Carbethoxy-γ,γ-diphenylvinylacetic acid". Organic Syntheses. 30: 18. doi:10.15227/orgsyn.030.0018.
  9. ^ Page Module:Citation/CS1/styles.css has no content.Mintz, H. M.; Walling, C. (1969). "t-Butyl Hypochlorite". Org. Synth. 49: 9. doi:10.15227/orgsyn.049.0009.
  10. ^ Page Module:Citation/CS1/styles.css has no content.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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