Ethyl tert-butyl ether

Short description: Oxygenate gasoline additive in the production of gasoline from crude oil

Ethyl tert-butyl ether[1]

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

EC Number |

* 211-309-7

PubChem CID

* 12512

RTECS number |

* KN4730200

UNII |

* 3R9B16WR19 Y

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 pictograms |
GHS Signal word | Danger

GHS hazard statements

| H224, H225, H315, H319, H335, H336

GHS precautionary statements

| P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+352, P303+361+353, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P370+378, P403+233, P403+235, 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

Tracking categories (test):

* SizeSet

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.

## Contents

* 1 Production
* 2 See also
* 3 References
* 4 External links

## 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

## References

1. ↑ Merck Index, 11th Edition, 3732.
2. ↑ 2.0 2.1 Grömping, Matthias; Höper, Frank; Leistner, Jörg; Nierlich, Franz; Peters, Udo; Praefke, Jochen; Rix, Armin; Röttger, Dirk et al.. "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". Evonik Degussa GmbH. https://patents.google.com/patent/DE102005062722A1/en?q=verfahren+zur+herstellung+von&q=etbe&oq=verfahren+zur+herstellung+von+etbe.

## External links

* EC Joint Research Centre ETBE risk assessment report[yes|permanent dead link|dead link}}]
* Directive 98/70/EC of the European Parliament and of the Council of 13 October 1998 relating to the quality of petrol and diesel fuels and amending Council Directive 93/12/EEC
* An assessment of the impact of ethanol-blended petrol on the total NMVOC emission from road transport in selected countries

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*[CID]: Compound ID
*[H224]: Extremely flammable liquid and vapour
*[H225]: Highly flammable liquid and vapour
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[H336]: May cause drowsiness or dizziness
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P370+378]: In case of fire: Use … for extinction
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P403+235]: Store in a well ventilated place. Keep cool
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …