Dimethyl ether

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Dimethyl Ether
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Names
IUPAC name
Methoxymethane
Preferred IUPAC name
Methoxymethane[1]
Other names
Dimethyl ether[1]
R-E170
Demeon
Dimethyl oxide
Dymel A
Methyl ether
Methyl oxide
Mether
Wood ether
2-oxapropane
Identifiers
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3D model (JSmol)
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Abbreviations DME
1730743
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MeSH Dimethyl+ether
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UN number 1033
  • InChI=1S/C2H6O/c1-3-2/h1-2H3 checkY
    Key: LCGLNKUTAGEVQW-UHFFFAOYSA-N checkY
  • InChI=1/C2H6O/c1-3-2/h1-2H3
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  • COC
Properties
C2H6O
Molar mass 46.069 g·mol−1
Appearance Colorless gas
Odor Ethereal[2]
Density 2.1146 kg m−3 (gas, 0 °C, 1013 mbar)[2]
0.735 g/mL (liquid, −25 °C)[2]
Melting point −141 °C; −222 °F; 132 K
Boiling point −24 °C; −11 °F; 249 K
71 g/L (at Template:Cvt)
log P 0.022
Vapor pressure 592.8 kPa[3]
−26.3×10−6 cm3 mol−1
1.30 D
Thermochemistry
65.57 J K−1 mol−1
−184.1 kJ mol−1
−1460.4 kJ mol−1
Hazards
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2
4
1
Flash point −41 °C (−42 °F; 232 K)
350 °C (662 °F; 623 K)
Explosive limits 27 %
Safety data sheet (SDS) ≥99% Sigma-Aldrich
Related compounds
Related ethers
 Diethyl ether

Polyethylene glycol

Related compounds
 Ethanol

Methanol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

Dimethyl ether (DME; also known as methoxymethane) is the organic compound with the formula CH3OCH3, (sometimes ambiguously simplified to C2H6O as it is an isomer of ethanol). 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.

Dimethyl ether was first synthesised by Jean-Baptiste Dumas and Eugene Péligot in 1835 by distillation of methanol and sulfuric acid.[5]

Production

Approximately 50,000 tons were produced in 1985 in Western Europe by dehydration of methanol:[6]

Page Module:Chem2/styles.css has no content.2 CH3OH → (CH3)2O + H2O

The required methanol is obtained from synthesis gas (syngas).[7] 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.[7][8] Both the one-step and two-step processes above are commercially available. The two-step process is relatively simple and start-up costs are relatively low. A one-step liquid-phase process is in development.[7][9]

From biomass

Dimethyl ether is a synthetic second generation biofuel (BioDME), which can be produced from lignocellulosic biomass.[10] The EU is considering BioDME in its potential biofuel mix in 2030;[11] It can also be made from biogas or methane from animal, food, and agricultural waste,[12][13] or even from shale gas or natural gas.[14]

The Volvo Group is the coordinator for the European Community Seventh Framework Programme project BioDME[15][16] where Chemrec's BioDME pilot plant is based on black liquor gasification in Piteå, Sweden.[17]

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:

CHA3OCHA3+SOA3⟶(CHA3)A2SOA4

Dimethyl ether can also be converted into acetic acid using carbonylation technology related to the Monsanto acetic acid process:[6]

CHA3−O−CHA3+2CO+HA2O⟶2CHA3COOH

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.[18]

Niche applications

A mixture of dimethyl ether and propane is used in some over-the-counter "freeze spray" products to treat warts by freezing them.[19][20] In this role, it has supplanted halocarbon compounds (Freon).

Dimethyl ether is also a component of certain high temperature "Map-Pro" blowtorch gas blends, supplanting the use of methyl acetylene and propadiene mixtures.[21]

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

Research

Fuel

File:Chemrec 5 - small.JPG
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.[22] Dimethyl ether can also be used as a blendstock in propane autogas.[23]

It is also a promising fuel in diesel engines,[24] 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.[25] Only moderate modifications are needed to convert a diesel engine to burn dimethyl ether. The simplicity of this short carbon chain compound leads to very low emissions of particulate matter during combustion. 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).[26]

At the European Shell Eco Marathon, an unofficial World Championship for mileage, a vehicle running on 100 % dimethyl ether achieved a fuel economy of 0.170L/100km, fuel equivalent to gasoline with a 50 cm3 displacement 2-stroke engine. [27]

To study the dimethyl ether for the combustion process a chemical kinetic mechanism[28] is required which can be used for Computational fluid dynamics calculation.

Refrigerant

Dimethyl ether is a refrigerant with ASHRAE refrigerant designation R-E170.[29] It is also used in refrigerant blends with e.g. ammonia, carbon dioxide, butane and propene. Dimethyl ether was the first refrigerant. In 1876, the French engineer Charles Tellier bought the ex-Elder-Dempster a 690 tons cargo ship Eboe and fitted a methyl-ether refrigerating plant of his design. The ship was renamed Le Frigorifique and successfully imported a cargo of refrigerated meat from Argentina. However the machinery could be improved and in 1877 another refrigerated ship called Paraguay with a refrigerating plant improved by Ferdinand Carré was put into service on the South American run.[30]

Safety

Unlike other alkyl ethers, dimethyl ether resists autoxidation.[31] Dimethyl ether is also relatively non-toxic, although it is highly flammable. On July 28, 1948, a BASF factory in Ludwigshafen suffered an explosion after 30 tonnes of dimethyl ether leaked from a tank and ignited in the air. 200 people died, and a third of the industrial plant was destroyed.[32]

Data sheet

Routes to produce dimethyl ether

File:DME process diagram.svg

Vapor pressure

Experimental vapor pressures of dimethyl ether[33]
Temperature (K) Pressure (kPa)
233.128 54.61
238.126 68.49
243.157 85.57
248.152 105.59
253.152 129.42
258.16Template:Figure space 157.53
263.16Template:Figure space 190.44
268.161 228.48
273.153 272.17
278.145 321.87
283.16Template:Figure space 378.66
288.174 443.57
293.161 515.53
298.172 596.21
303.16Template:Figure space 687.37
305.16Template:Figure space 726.26
308.158 787.07
313.156 897.59
316.154 968.55
318.158 1018.91
323.148 1152.35
328.149 1298.23
333.157 1457.5Template:Figure space
333.159 1457.76
338.154 1631.01
343.147 1818.8Template:Figure space
348.147 2022.45
353.146 2242.74
353.158 2243.07
358.145 2479.92
363.148 2735.67
368.158 3010.81
373.154 3305.67
378.15Template:Figure space 3622.6Template:Figure space
383.143 3962.25
388.155 4331.48
393.158 4725.02
398.157 5146.82
400.378 5355.8Template:Figure space

See also

References

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