Ethyl tert-butyl ether

Ethyl tert-butyl ether[1]
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
2-Ethoxy-2-methylpropane
Other names
Ethyl tert-butyl ether
Ethyl tertiary butyl ether
Ethyl tert-butyl oxide
tert-Butyl ethyl ether
Ethyl t-butyl ether
Identifiers
CAS Number
3D model (JSmol)
Abbreviations ETBE
ChEBI
ChemSpider
ECHA InfoCard 100.010.282
EC Number
  • 211-309-7
PubChem CID
RTECS number
  • KN4730200
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H14O/c1-5-7-6(2,3)4/h5H2,1-4H3 checkY
    Key: NUMQCACRALPSHD-UHFFFAOYSA-N checkY
  • InChI=1/C6H14O/c1-5-7-6(2,3)4/h5H2,1-4H3
    Key: NUMQCACRALPSHD-UHFFFAOYAB
SMILES
  • O(C(C)(C)C)CC
Properties
Chemical formula
 C6H14O
Molar mass 102.18
Appearance Clear colorless liquid
Density 0.7364 g/cm3
Melting point −94 °C (−137 °F; 179 K)
Boiling point 69 to 71 °C (156 to 160 °F; 342 to 344 K)
Solubility in water
 1.2 g/100 g
Hazards
GHS labelling:
Pictograms
 GHS02: FlammableGHS07: Exclamation mark
Signal word
 Danger
Hazard statements
 H224, H225, H315, H319, H335, H336
Precautionary statements
 P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
Flash point −19 °C (−2 °F; 254 K)
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 ?)
Infobox references

Ethyl tertiary-butyl ether (ETBE), also known as ethyl tert-butyl ether, is commonly used as an oxygenate gasoline additive in the production of gasoline from crude oil. ETBE offers equal or greater air quality benefits than ethanol, while being technically and logistically less challenging. Unlike ethanol, ETBE does not induce evaporation of gasoline, which is one of the causes of smog, and does not absorb moisture from the atmosphere.

Production

Ethyl tert-butyl ether is manufactured industrially by the acidic etherification of isobutylene with ethanol at a temperature of 30–110 °C and a pressure of 0.8–1.3 MPa. The reaction is carried out with an acidic ion-exchange resin as a catalyst.[2]

Synthesis of Ethyl tert-butyl ether
Synthesis of Ethyl tert-butyl ether

Suitable reactors are fixed-bed reactors such as tube bundle or circulation reactors in which the reflux can be cooled optionally.[2]

Ethanol, produced by fermentation and distillation, is more expensive than methanol, which is derived from natural gas. Therefore, MTBE, made from methanol, is cheaper than ETBE, made from ethanol.

See also

References

  1. ^ Merck Index, 11th Edition, 3732.
  2. ^ a b Grömping, Matthias; Höper, Frank; Leistner, Jörg; Nierlich, Franz; Peters, Udo; Praefke, Jochen; Rix, Armin; Röttger, Dirk; Santiago Fernandez, Silvia. "Preparing ethyl tertiary butylether from hydrocarbon mixture, useful as fuel additive, comprises reacting isobutene with ethanol, separating the hydrocarbon, reacting separated isobutene with ethanol and separating unconverted hydrocarbon". Google Patents. Evonik Degussa GmbH. Retrieved 5 March 2019.
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