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 | |
| Std enthalpy of
formation (ΔfH |
-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.
Contents
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
- ↑ 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
- ↑ Howlett; Journal of the Chemical Society; (1955); p. 1784,1788
- ↑ Luo, Yu-Ran; Benson, Sidney W.; Journal of Physical Chemistry; vol. 92; nb. 18; (1988); p. 5255 - 5257
- ↑ https://www.prepchem.com/synthesis-of-tert-butyl-chloride
- ↑ https://www.youtube.com/watch?v=WjOz1NM_n8Q
- ↑ https://www.youtube.com/watch?v=aa_LTVt8QVg
- ↑ https://pubs.acs.org/doi/abs/10.1021/ie50358a017
