Dimethyl ether

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This article is about dimethyl ether. It is not to be confused with dimethoxyethane.
Dimethyl ether

Names
Preferred IUPAC name
Methoxymethane
Other names
Dimethyl ether
R-E170
Demeon

Dimethyl oxide
Dymel A
Methyl ether
Mether

Wood ether
Identifiers
 115-10-6
CAS Number
 Interactive image
3D model (JSmol)
Abbreviations DME
Beilstein Reference 1730743
 CHEBI:28887
ChEBI
 7956
ChemSpider
ECHA InfoCard 100.003.696
EC Number 204-065-8
 C11144
KEGG
MeSH Dimethyl+ether
 8254
PubChem CID
RTECS number PM4780000
 AM13FS69BX
UNII
UN number 1033
InChI[show]
SMILES[show]
Properties
Chemical formula C2H6O
Molar mass 46.07 g·mol−1
Appearance Colorless gas
Odor Typical
2.1146 kg/m3 (gas, 0 °C, 1013
Density mbar)[1]
0.735 g/mL (liquid, -25 °C)[1]
Melting point −141 °C; −222 °F; 132 K
Boiling point −24 °C; −11 °F; 249 K
Solubility in water 71 g/L (at 20 °C (68 °F))
log P 0.022
Vapor pressure >100 kPa
Magnetic
-26.3·10−6 cm3/mol
susceptibility (χ)
Dipole moment 1.30 D
Thermochemistry
Specific
65.57 J K−1 mol−1
heat capacity (C)
Std enthalpy of
−184.1 kJ mol−1
formation (ΔfHo298)
Std enthalpy of
o −1.4604 MJ mol−1
combustion (ΔcH 298)
Hazards
See: data page
Safety data sheet
≥99% Sigma-Aldrich

GHS pictograms

GHS signal word Danger

GHS hazard
H220
statements
GHS precautionary
P210, P410+403
statements
NFPA 704

4
 1
1
Flash point −41 °C (−42 °F; 232 K)
Autoignition
350 °C (662 °F; 623 K)
temperature
Explosive limits 27%
Related compounds
Diethyl ether
Related ethers
Polyethylene glycol
Ethanol
Related compounds
Methanol
Supplementary data page
Structure and Refractive index (n),
properties Dielectric constant (εr), etc.
Thermodynamic Phase behaviour
data solid–liquid–gas
Spectral data UV, IR, NMR, MS
Except where otherwise noted, data are given for
materials in their standard state (at 25 °C [77 °F],
100 kPa).
verify (what is ?)
Infobox references

Dimethyl ether (DME), also known as methoxymethane, is the organic compound with
the formula CH3OCH3, simplified to C2H6O. The simplest ether, it is a colorless gas that is a
useful precursor to other organic compounds and an aerosol propellant that is currently
being demonstrated for use in a variety of fuel applications. It is an isomer of ethanol.

Contents
 1 Production
 2 Applications
o 2.1 Laboratory reagent and solvent
o 2.2 Niche applications
 3 Research
o 3.1 Fuel
o 3.2 Processes
o 3.3 Refrigerant
 4 Safety
 5 References
 6 External links
Production
Approximately 50,000 tons were produced in 1985 in Western Europe by dehydration of
methanol:[2]

2 CH3OH → (CH3)2O + H2O

The required methanol is obtained from synthesis gas (syngas).[3] In principle, the methanol
could be obtained from organic waste or biomass. Other possible improvements call for a
dual catalyst system that permits both methanol synthesis and dehydration in the same
process unit, with no methanol isolation and purification.[3][4]

Both the one-step and two-step processes above are commercially available. Currently,
there is more widespread application of the two-step process, since it is relatively simple
and start-up costs are relatively low. There is also a one-step liquid-phase process in
development.[3][5]

Applications
The largest use of dimethyl ether is as the feedstock for the production of the methylating
agent, dimethyl sulfate, which entails its reaction with sulfur trioxide:

CH
3OCH
3 + SO
3 → (CH
3)
2SO
4

Dimethyl ether can also be converted into acetic acid using carbonylation technology
related to the Monsanto acetic acid process:[2]

(CH
3)
2O + 2 CO + H2O → 2 CH3CO2H

Laboratory reagent and solvent

Dimethyl ether is a low-temperature solvent and extraction agent, applicable to specialised

laboratory procedures. Its usefulness is limited by its low boiling point (−23 °C (−9 °F)),
but the same property facilitates its removal from reaction mixtures. Dimethyl ether is the
precursor to the useful alkylating agent, trimethyloxonium tetrafluoroborate.[6]

Niche applications
A mixture of dimethyl ether and propane is used in an over-the-counter device to treat
warts, by freezing them.[7][8]

Dimethyl ether is the main constituent of "freeze spray", a spot-coolant used in field testing
of electronic components.[9] In this role it has supplanted halocarbon compounds (Freon),
which have been suspected of contributing to ozone depletion in the Earth's atmosphere.

Dimethyl ether is also a component of certain high temperature "MAP-plus" blowtorch gas
blends, supplanting the use of methyl acetylene and propadiene mixtures.[10]

Dimethyl either is also used as a propellant in aerosol products. Such products include hair
spray, bug spray and some aerosol glue products.

Research
Fuel

Installation of BioDME synthesis towers at Chemrec's pilot facility

A potentially major use of dimethyl ether is as substitute for propane in LPG used as fuel in
household and industry.[11]

It is also a promising fuel in diesel engines,[12] petrol engines (30% DME / 70% LPG), and
gas turbines. For diesel engines, an advantage is the high cetane number of 55, compared to
that of diesel fuel from petroleum, which is 40–53.[13] Only moderate modifications are
needed to convert a diesel engine to burn dimethyl ether. The simplicity of this short carbon
chain compound leads during combustion to very low emissions of particulate matter, NOx,
and CO. For these reasons as well as being sulfur-free, dimethyl ether meets even the most
stringent emission regulations in Europe (EURO5), U.S. (U.S. 2010), and Japan (2009
Japan).[14] Mobil uses dimethyl ether in their methanol to gasoline process.[citation needed]

Dimethyl ether is being developed as a synthetic second generation biofuel (BioDME),

which can be manufactured from lignocellulosic biomass.[15] Currently the EU is
considering BioDME in its potential biofuel mix in 2030;[16] the Volvo Group is the
coordinator for the European Community Seventh Framework Programme project
BioDME[17][18] where Chemrec's BioDME pilot plant based on black liquor gasification is
nearing completion in Piteå, Sweden.[19]
At the European Shell Eco Marathon, an unofficial World Championship for mileage,
vehicle running on 100% dimethyl ether drove 589 km/liter, fuel equivalent to gasoline
with a 50 cc 2-stroke Diesel engine. As well as winning they beat the old standing record of
306 km/liter, set by the same team in 2007.[20]

Processes

The image below illustrates some of processes from various raw materials to dimethyl
ether.

Refrigerant

Dimethyl ether is a refrigerant with ASHRAE refrigerant designation R-E170. It is also

used in refrigerant blends with e.g. ammonia, carbon dioxide, butane and propene.[21]

Safety
Unlike other alkyl ethers, dimethyl ether resists autoxidation. Dimethyl ether is also
relatively non-toxic, although it is highly flammable