tert-Butyl chloride

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tert-Butyl chloride
Names
IUPAC name
2-chloro-2-methyl propane
Other names
1,1-Dimethylethyl chloride
1-Chloro-1,1-dimethylethane
Chlorotrimethylmethane
Trimethylchloromethane
t-BuCl
t-Butyl chloride
tert-BuCl
Properties
C4H9Cl
(CH3)3CCl
Molar mass 92.57 g/mol
Appearance Colorless liquid
Density 0.851 g/cm3 (25 °C)[1]
Melting point −26 °C (−15 °F; 247 K)
Boiling point 51 °C (124 °F; 324 K)
0.288 g/ 100 ml (15 °C)
Slow hydrolysis, faster at higher temperatures
Solubility Slowly reacts with alcohols
Miscible with benzene, chloroform, diethyl ether, THF, toluene
Vapor pressure 34.9 kPa (20 °C)
Thermochemistry
-182.544 kJ/mol[3]
Hazards
Safety data sheet Sigma-Aldrich
Flash point −9 °C (16 °F; 264 K) (open cup)
−23 °C (-9.4 °F; 250 K) (closed cup)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

tert-Butyl chloride is an organochlorine compound, with the formula (CH3)3CCl, used as a precursor to many chemical compounds.

Properties

Chemical

Although t-butyl chloride is insoluble in water, prolonged contact will cause it to hydrolyze to t-butanol. If added to an alcohol, an ether of tert-butyl and said alcohol will be produced.

Physical

t-Butyl chloride is a volatile colorless liquid with a characteristic odor. It is insoluble in water, and will slowly hydrolyze in it, but miscible with ethers, esters, halocarbons. While it dissolves in alcohols, it will slowly react with them as well.

Availability

tert-Butyl chloride is sold by various chemical suppliers.

Preparation

tert-Butyl chloride can be easily synthesized by the reaction of tert-butyl alcohol with a stream of hydrogen chloride.

Concentrated hydrochloric acid can also be used, and this is much safer than handling gaseous HCl, although the yield will be lower, due to slight hydrolysis.[4][5][6]

Industrial production involves a gas phase reaction between isobutene and hydrogen chloride, in the presence of aluminum oxide at 100 °C.[7]

Projects

  • Make tert-butanol
  • Make t-butyl benzene

Handling

Safety

tert-Butyl chloride is irritant, volatile and flammable. Handle it with care.

Storage

In closed bottles, away from moisture.

Disposal

Can be safely neutralized to t-butanol by adding it in water. NaOH can also be added to accelerate the hydrolysis.

References

  1. Guerrero, Hernando; Ballesteros, Luz Marina; Garcia-Mardones, Monica; Lafuente, Carlos; Gascon, Ignacio; Journal of Chemical and Engineering Data; vol. 57; nb. 7; (2012); p. 2076 - 2083
  2. Howlett; Journal of the Chemical Society; (1955); p. 1784,1788
  3. Luo, Yu-Ran; Benson, Sidney W.; Journal of Physical Chemistry; vol. 92; nb. 18; (1988); p. 5255 - 5257
  4. https://www.prepchem.com/synthesis-of-tert-butyl-chloride
  5. https://www.youtube.com/watch?v=WjOz1NM_n8Q
  6. https://www.youtube.com/watch?v=aa_LTVt8QVg
  7. https://pubs.acs.org/doi/abs/10.1021/ie50358a017

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