Dimethyl ether
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Names | |||
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Preferred IUPAC name
Methoxymethane[1] | |||
Other names | |||
Identifiers | |||
3D model (
JSmol ) |
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Abbreviations | DME | ||
1730743 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
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100.003.696 | ||
EC Number |
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KEGG | |||
MeSH | Dimethyl+ether | ||
PubChem CID
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RTECS number
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UNII | |||
UN number | 1033 | ||
CompTox Dashboard (EPA)
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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 20 °C (68 °F)) | |||
log P | 0.022 | ||
Vapor pressure | 592.8 kPa[3] | ||
−26.3×10−6 cm3 mol−1 | |||
1.30 D | |||
Thermochemistry | |||
Heat capacity (C)
|
65.57 J K−1 mol−1 | ||
Std enthalpy of (ΔfH⦵298)formation |
−184.1 kJ mol−1 | ||
Std enthalpy of (ΔcH⦵298)combustion |
−1460.4 kJ mol−1 | ||
Hazards | |||
GHS labelling:[4] | |||
Danger | |||
H220, H280 | |||
P210, P377, P381, P403 | |||
NFPA 704 (fire diamond) | |||
Flash point | −41 °C (−42 °F; 232 K) | ||
350 °C (662 °F; 623 K) | |||
Explosive limits
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27 % | ||
Safety data sheet (SDS) | ≥99% Sigma-Aldrich | ||
Related compounds | |||
Related ethers
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Diethyl ether | ||
Related compounds
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Ethanol | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
Production
Approximately 50,000 tons were produced in 1985 in Western Europe by dehydration of methanol:[6]
- 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
The
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
- (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
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
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.[22] Dimethyl ether can also be used as a blendstock in propane autogas.[23]
It is also a promising fuel in
At the European Shell Eco Marathon, an unofficial World Championship for mileage, vehicle running on 100 % dimethyl ether drove 589 km/L (169.8 cm3/100 km), fuel equivalent to gasoline with a 50 cm3 displacement 2-stroke engine. As well as winning they beat the old standing record of 306 km/liter (326.8 cm3/100 km), set by the same team in 2007.[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
Safety
Unlike other alkyl ethers, dimethyl ether resists autoxidation.[31] Dimethyl ether is also relatively non-toxic, although it is highly flammable. BASF Explosion Disaster on July 28, 1948 in Ludwigshafen was caused by this compound—200 people died, a third of the industrial plant was destroyed.[32]
Data sheet
Routes to produce dimethyl ether
Vapor pressure
Temperature (K) | Pressure (kPa) |
---|---|
233.128 | 54.61 |
238.126 | 68.49 |
243.157 | 85.57 |
248.152 | 105.59 |
253.152 | 129.42 |
258.16 | 157.53 |
263.16 | 190.44 |
268.161 | 228.48 |
273.153 | 272.17 |
278.145 | 321.87 |
283.16 | 378.66 |
288.174 | 443.57 |
293.161 | 515.53 |
298.172 | 596.21 |
303.16 | 687.37 |
305.16 | 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 | 1457.5 |
333.159 | 1457.76 |
338.154 | 1631.01 |
343.147 | 1818.8 |
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 |
378.15 | 3622.6 |
383.143 | 3962.25 |
388.155 | 4331.48 |
393.158 | 4725.02 |
398.157 | 5146.82 |
400.378 | 5355.8 |
See also
References
- ^ ISBN 978-0-85404-182-4.
- ^ a b c Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ "Dimethylether". 19 October 2018. Archived from the original on 6 November 2021. Retrieved 10 November 2020.
- ^ GHS: Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ Ann. chim. phys., 1835, [2] 58, p. 19
- ^
- ^ a b c "CHEMSYSTEMS.COM" (PDF). www.chemsystems.com. Archived from the original (PDF) on 22 November 2009. Retrieved 1 April 2018.
- ^ P.S. Sai Prasad et al., Fuel Processing Technology, 2008, 89, 1281.
- ^ "Air Products Technology Offerings". airproducts.com. Archived from the original on 12 December 2007. Retrieved 1 April 2018.
- ^ "BioDME". www.biodme.eu. Archived from the original on 10 April 2020. Retrieved 1 April 2018.
- ^ "Biofuels in the European Union, 2006" (PDF). europa.eu. Archived (PDF) from the original on 3 December 2019. Retrieved 1 April 2018.
- ^ "Oberon Fuels Brings Production Units Online, Launching the First North American Fuel-grade DME Facilities". 7 June 2013. Archived from the original on 2021-05-06. Retrieved 2018-08-04.
- ^ "Associated Gas Utilization via mini GTL" (PDF). Archived (PDF) from the original on 2018-08-04. Retrieved 2018-08-04.
- ISBN 9780444515995.
- ^ "Home | Volvo Group". Archived from the original on 2009-05-25. Retrieved 2011-11-04.
- ^ "Volvo Group - Driving prosperity through transport solutions". www.volvo.com. Archived from the original on 6 June 2020. Retrieved 1 April 2018.
- ^ Chemrec press release September 9, 2010 Archived June 12, 2017, at the Wayback Machine
- ^ T. J. Curphey (1988). "Trimethyloxonium tetrafluoroborate". Organic Syntheses; Collected Volumes, vol. 6, p. 1019.
- ^ "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.
- ^ "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) - ^ "Archived copy" (PDF). Archived from the original (PDF) on 2016-12-20. Retrieved 2016-03-02.
{{cite web}}
: CS1 maint: archived copy as title (link) - ^ "IDA Fact Sheet DME/LPG Blends 2010 v1" (PDF). aboutdme.org. Archived (PDF) from the original on 24 July 2011. Retrieved 1 April 2018.
- from the original on 2022-05-04. Retrieved 2020-11-21.
- ^ nycomb.se, Nycomb Chemicals company Archived 2008-06-03 at the Wayback Machine
- ^ "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
- ^ "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 - ^ "The Danish Ecocar Team - List of achievements". dtu.dk. Archived from the original on 17 October 2009. Retrieved 1 April 2018.
- from the original on 2022-05-04. Retrieved 2020-05-18.
- ^ A history of the frozen meat trade, page 26-28
- ^ http://www.ashrae.org/technology/page/1933#et Archived 2012-01-03 at the Wayback Machine ASHRAE list of refrigerants
- ^ 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
- ^ Welt im Film 167/1948 Archived 2021-01-29 at the Wayback Machine. filmothek.bundesarchiv.de
- from the original on 2022-05-04. Retrieved 2022-01-07.