Tert Butanol Synthesis Essay

Names
Preferred IUPAC name
Other names
  • t-Butyl alcohol
  • tert-Butanol
  • Trimethyl carbinol[1]
  • 2-Methyl-2-propanol
  • 2M2P
Identifiers

CAS Number

3D model (JSmol)

Beilstein Reference

906698
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.000.809
EC Number200-889-7

Gmelin Reference

1833
MeSHtert-Butyl+Alcohol

PubChemCID

RTECS numberEO1925000
UNII
UN number1120

InChI

  • InChI=1S/C4H10O/c1-4(2,3)5/h5H,1-3H3 Y
    Key: DKGAVHZHDRPRBM-UHFFFAOYSA-N Y
Properties

Chemical formula

C4H10O
Molar mass74.12 g·mol−1
AppearanceColorless liquid
OdorCamphorous
Density0.775 g/mL
Melting point25 to 26 °C; 77 to 79 °F; 298 to 299 K
Boiling point82 to 83 °C; 179 to 181 °F; 355 to 356 K

Solubility in water

miscible[2]
log P0.584
Vapor pressure4.1 kPa (at 20 °C)
Acidity (pKa)16.54 [3]

Magnetic susceptibility (χ)

-57.42·10−6 cm3/mol

Refractive index (nD)

1.387
Thermochemistry

Specific
heat capacity (C)

215.37 J K−1 mol−1

Std molar
entropy (S298)

189.5 J K−1 mol−1

Std enthalpy of
formation (ΔfH298)

−360.04–−358.36 kJ mol−1

Std enthalpy of
combustion (ΔcH298)

−2.64479–−2.64321 MJ mol−1
Hazards
Safety data sheetinchem.org
GHS pictograms
GHS signal wordDANGER

GHS hazard statements

H225, H319, H332, H335

GHS precautionary statements

P210, P261, P305+351+338
NFPA 704
Flash point11 °C (52 °F; 284 K)

Autoignition
temperature

480 °C (896 °F; 753 K)
Explosive limits2.4–8.0%
Lethal dose or concentration (LD, LC):

LD50 (median dose)

3559 mg/kg (rabbit, oral)
3500 mg/kg (rat, oral)[4]
US health exposure limits (NIOSH):

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]
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).

Y verify (what is YN ?)
Infobox references

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.[5]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[edit]

tert-Butyl alcohol has been identified in beer and chickpeas.[6] It is also found in cassava[7] which is used as fermentation ingredient in certain alcoholic beverages.

Preparation[edit]

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 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.[8]

Applications[edit]

tert-Butyl alcohol is used as a solvent, ethanol denaturant, paint remover ingredient, and gasolineoctane 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[edit]

As a tertiary alcohol, tert-butyl alcohol is more resistant to oxidation and less reactive than the other isomers of butanol.

When tert-butyl alcohol is deprotonated with a strong base, the product is an alkoxide anion. In this case, it is tert-butoxide. For example, the commonly used organic reagent potassium tert-butoxide is prepared by refluxing dry tert-butanol with potassium metal.[9]

K + tBuOH → tBuOK+ + 0.5 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.

It also reacts with sodium in liquid ammonia.

References[edit]

External links[edit]

  1. ^ abcd"NIOSH Pocket Guide to Chemical Hazards #0078". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^http://www.inchem.org/documents/icsc/icsc/eics0114.htm
  3. ^Reeve, W.; Erikson, C.M.; Aluotto, P.F. Can. J. Chem, 1979, 57, 2747.
  4. ^"Tert-Butyl alcohol". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). 
  5. ^In tert-butyl alcohol, three methyl groups substitute for three hydrogen atoms in methanol, just as two methyl groups substitute for two hydrogen atoms in isopropyl alcohol, and one methyl group substitutes for one hydrogen atom in ethanol.
  6. ^http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+50
  7. ^http://www.sc.mahidol.ac.th/scbc/bc_internet/publication/696.pdf
  8. ^D.D. Perrin, W.L.F. Armarego (1988). Purification of Laboratory Chemicals (3rd ed.). Pergamon Press Ltd. 
  9. ^Johnson, W. S.; Schneider, W. P. (1950). "β-Carbethoxy-γ,γ-diphenylvinylacetic acid". Organic Syntheses. 30: 18. ; Collective Volume, 4, p. 132 

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