Ethyl tert-butyl ether

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.

Ethyl tert-butyl ether^[1]

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	637-92-3 Y
3D model (JSmol)	Interactive image
Abbreviations	ETBE
ChEBI	CHEBI:141564
ChemSpider	11996 Y
ECHA InfoCard	100.010.282
EC Number	211-309-7
PubChem CID	12512
RTECS number	KN4730200
UNII	3R9B16WR19 Y
CompTox Dashboard (EPA)	DTXSID601024578 DTXSID0025604, DTXSID601024578
InChI InChI=1S/C6H14O/c1-5-7-6(2,3)4/h5H2,1-4H3 Y Key: NUMQCACRALPSHD-UHFFFAOYSA-N Y 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
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). Y verify (what is YN ?) Infobox references

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

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

• Methyl tert-butyl ether (MTBE)
• tert-Amyl methyl ether (TAME)
• Tetraethyllead (TEL)
• List of gasoline additives