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Dimethyl ether

Names
Preferred IUPAC name Methoxymethane
Other names Dimethyl ether R-E170 Demeon Dimethyl oxide Dymel A Methyl ether Methyl oxide Mether Wood ether
Identifiers
CAS Number	115-10-6
3D model (JSmol)	Interactive image
Abbreviations	DME
Beilstein Reference	1730743
ChEBI	CHEBI:28887
ChEMBL	ChEMBL119178
ChemSpider	7956
ECHA InfoCard	100.003.696
EC Number	204-065-8
KEGG	C11144
MeSH	Dimethyl+ether
PubChem CID	8254
RTECS number	PM4780000
UNII	AM13FS69BX
UN number	1033
CompTox Dashboard (EPA)	DTXSID8026937
InChI InChI=1S/C2H6O/c1-3-2/h1-2H3Key: LCGLNKUTAGEVQW-UHFFFAOYSA-N InChI=1/C2H6O/c1-3-2/h1-2H3Key: LCGLNKUTAGEVQW-UHFFFAOYAU
SMILES COC
Properties
Chemical formula	C2H6O
Molar mass	46.069 g·mol
Appearance	Colorless gas
Odor	Ethereal
Density	2.1146 kg m (gas, 0 °C, 1013 mbar) 0.735 g/mL (liquid, −25 °C)
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	592.8 kPa
Magnetic susceptibility (χ)	−26.3×10 cm mol
Dipole moment	1.30 D
Thermochemistry
Heat capacity (C)	65.57 J K mol
Std enthalpy of formation (ΔfH298)	−184.1 kJ mol
Std enthalpy of combustion (ΔcH298)	−1460.4 kJ mol
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H220
Precautionary statements	P210, P377, P381, P403
NFPA 704 (fire diamond)	2 4 1
Flash point	−41 °C (−42 °F; 232 K)
Autoignition temperature	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 , 100 kPa). Y verify (what is  ?) Infobox references

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.

Production

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

2 CH₃OH → (CH₃)₂O + H₂O

The required methanol is obtained from synthesis gas (syngas). 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. 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.

From biomass

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

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

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:

CH₃OCH₃ + SO₃ → (CH₃)₂SO₄

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

(CH₃)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.

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. 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.

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

A potentially major use of dimethyl ether is as substitute for propane in LPG used as fuel in household and industry. Dimethyl ether can also be used as a blendstock in propane autogas.

It is also a promising fuel in diesel engines, 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. 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).

At the European Shell Eco Marathon, an unofficial World Championship for mileage, vehicle running on 100 % dimethyl ether drove 589 km/L (169.8 cm/100 km), fuel equivalent to gasoline with a 50 cm displacement 2-stroke engine. As well as winning they beat the old standing record of 306 km/liter (326.8 cm/100 km), set by the same team in 2007.

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

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. 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.

Safety

Unlike other alkyl ethers, dimethyl ether resists autoxidation. 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.

Data sheet

Routes to produce dimethyl ether

Vapor pressure

See also

• Methanol economy

References

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2. ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
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19. "A Pharmacist's Guide to OTC Therapy: OTC Treatments for Warts". July 2006. Archived from the original on 2010-06-17. Retrieved 2009-05-02.
20. "Archived copy" (PDF). Food and Drug Administration. Archived from the original (PDF) on 2009-04-20. Retrieved 2019-12-16.{{cite web}}: CS1 maint: archived copy as title (link)
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24. nycomb.se, Nycomb Chemicals company Archived 2008-06-03 at the Wayback Machine
25. "Haldor Topsoe - Products & Services - Technologies - DME - Applications - DME as Diesel Fuel". Archived from the original on 2007-10-08. Retrieved 2011-11-04. topsoe.com
26. "Archived copy" (PDF). Archived from the original (PDF) on 2009-01-07. Retrieved 2011-11-04.{{cite web}}: CS1 maint: archived copy as title (link), Conference on the Development and Promotion of Environmentally Friendly Heavy Duty Vehicles such as DME Trucks, Washington DC, March 17, 2006
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28. Shrestha, Krishna P.; Eckart, Sven; Elbaz, Ayman M.; Giri, Binod R.; Fritsche, Chris; Seidel, Lars; Roberts, William L.; Krause, Hartmut; Mauss, Fabian (2020). "A comprehensive kinetic model for dimethyl ether and dimethoxymethane oxidation and NO interaction utilizing experimental laminar flame speed measurements at elevated pressure and temperature". Combustion and Flame. 218: 57–74. doi:10.1016/j.combustflame.2020.04.016. hdl:10754/662921. S2CID 219772095. Archived from the original on 2022-05-04. Retrieved 2020-05-18.
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31. A comparative study on the autoxidation of dimethyl ether (DME) comparison with diethyl ether (DEE) and diisopropyl ether (DIPE), Michie Naito, Claire Radcliffe, Yuji Wada, Takashi Hoshino, Xiongmin Liu, Mitsuru Arai, Masamitsu Tamura. Journal of Loss Prevention in the Process Industries, Volume 18, Issues 4–6, July–November 2005, Pages 469–473 DOI
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External links

• The International DME Association Archived 2010-11-26 at the Wayback Machine
• NOAA site for NFPA 704
• XTL & DME Institute

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• Aerosol propellants
• Dialkyl ethers
• Fuels
• Synthetic fuels
• Symmetrical ethers
• Organic compounds with 2 carbon atoms
• Substances discovered in the 19th century