Methanol

Not to be confused with menthol or methanal.
Methanol
Names
Preferred IUPAC name
Methanol[1]
Other names
Carbinol
Columbian spirits
Hydroxymethane
Methyl alcohol
Methyl hydrate
Methyl hydroxide
Methylic alcohol
Methylol
Pyroligneous spirit
Wood alcohol
Wood naphtha
Wood spirit
Identifiers
67-56-1 YesY
3D model (Jmol) Interactive image
3DMet B01170
1098229
ChEBI CHEBI:17790 YesY
ChEMBL ChEMBL14688 YesY
ChemSpider 864 YesY
ECHA InfoCard 100.000.599
EC Number 200-659-6
449
KEGG D02309 YesY
MeSH Methanol
PubChem 887
RTECS number PC1400000
UNII Y4S76JWI15 YesY
UN number 1230
Properties
CH
3OH
Molar mass 32.04 g mol−1
Appearance Colorless liquid
Density 0.792 g·cm−3[2]
Melting point −97.6 °C (−143.7 °F; 175.6 K)
Boiling point 64.7 °C (148.5 °F; 337.8 K)
miscible
log P -0.69
Vapor pressure 13.02 kPa (at 20 °C)
Acidity (pKa) 15.5[3]
1.33141[4]
Viscosity 0.545 mPa×s (at 25 °C) [5]
1.69 D
Hazards[6]
Safety data sheet See: data page
GHS pictograms [7]
GHS signal word Danger [7]
H225, H301, H311, H331, H370[7]
P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+310, P303+361+353, P304+340, P330[7]
F T
R-phrases R11, R23/24/25, R39/23/24/25
S-phrases (S1/2), S7, S16, S36/37, S45
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
3
1
0
Flash point 11 to 12 °C (52 to 54 °F; 284 to 285 K)
470[8] °C (878 °F; 743 K)
Explosive limits 6%-36%[9]
Lethal dose or concentration (LD, LC):
5628 mg/kg (rat, oral)
7300 mg/kg (mouse, oral)
12880 mg/kg (rat, oral)
14200 mg/kg (rabbit, oral)[10]
64,000 ppm (rat, 4 hr)[10]
33,082 ppm (cat, 6 hr)
37,594 ppm (mouse, 2 hr)[10]
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 200 ppm (260 mg/m3)[9]
REL (Recommended)
 TWA 200 ppm (260 mg/m3) ST 250 ppm (325 mg/m3) [skin][9]
IDLH (Immediate danger)
 6000 ppm[9]
Related compounds
Related compounds
 Methanethiol
Silanol
Supplementary data page
Refractive index (n),
Dielectric constant (εr), etc.
Thermodynamic
data
 Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Methanol (/ˈmɛθənɒl/), also known as methyl alcohol among others, is a chemical with the formula CH3OH (often abbreviated MeOH). Methanol acquired the name "wood alcohol" because it was once produced chiefly as a byproduct of the destructive distillation of wood. Today, industrial methanol is produced in a catalytic process directly from carbon monoxide, carbon dioxide, and hydrogen.

Methanol is the simplest alcohol, being only a methyl group linked to a hydroxyl group. It is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to that of ethanol (drinking alcohol).[11] However, unlike ethanol, methanol is highly toxic and unfit for consumption. At room temperature, it is a polar liquid, and is used as an antifreeze, solvent, fuel, and as a denaturant for ethanol. It is also used for producing biodiesel via transesterification reaction.

Methanol is produced naturally in the anaerobic metabolism of many varieties of bacteria, and is commonly present in small amounts in the environment. As a result, the atmosphere contains a small amount of methanol vapor. But in only a few days, atmospheric methanol is oxidized by sunlight to produce carbon dioxide and water.

Methanol is also found in abundant quantities in star forming regions of space, and is used in astronomy as a marker for such regions. It is detected through its spectral emission lines.[12]

Methanol when drunk is metabolized first to formaldehyde and then to formic acid or formate salts.[13] These are poisonous to the central nervous system and may result in blindness, coma, and death. Because of these toxic properties, methanol is frequently used as a denaturant additive for ethanol manufactured for industrial uses. This addition of methanol exempts industrial ethanol (commonly known as "denatured alcohol" or "methylated spirit") from liquor excise taxation in the US and some other countries.

Toxicity

Main article: Methanol toxicity

Methanol toxicity is poisoning from methanol.[14] Symptoms may include a decreased level of consciousness, poor coordination, vomiting, abdominal pain, and a specific smell on the breath.[14][15] Decreased vision may start as early as twelve hours after exposure.[15] Long term outcomes may include blindness and kidney failure. Toxicity and death may occur even after drinking a small amount.[14]

Methanol poisoning most commonly occurs following the drinking of windshield washer fluid.[15] This may be accidental or done purposefully in an attempt to cause death. Toxicity may also rarely occur through skin exposure or breathing in the fumes.[14] When methanol is broken down by the body it results in formaldehyde, formic acid, and formate which cause much of the toxicity.[15] The diagnosis may be suspected when there is acidosis or an increased osmol gap and confirmed by directly measuring blood levels.[14][15] Other conditions that can produce similar symptoms include infections, exposure to other toxic alcohols, serotonin syndrome, and diabetic ketoacidosis.[15]

Early treatment increases the chance of a good outcome. Treatment consists of stabilizing the person, followed by the use of an antidote. The preferred antidote is fomepizole, with ethanol used if this is not available. Hemodialysis may also be used in those where there is organ damage or a high degree of acidosis. Other treatments may include sodium bicarbonate, folate, and thiamine.[15]

Outbreaks have occurred due to contamination of drinking alcohol. This is more common in the developing world.[15] In 2013 more than 1700 cases occurred in the United States. Those affected are often adults and male.[16] Outcomes may be good with early treatment.[14] Toxicity to methanol has been described as early as 1856.[17]

Applications

Methanol is used primarily as a feedstock for the manufacture of chemicals, and as a fuel for specialized vehicles. As mentioned above, it is a common de-naturing agent. As a common laboratory solvent, is especially useful for HPLC, UV/VIS spectroscopy, and LCMS due to its low UV cutoff.

Chemical industry

Methanol is primarily used in making other chemicals. About 40% of methanol is converted to formaldehyde, and from there into products as diverse as plastics, plywood, paints, explosives, and permanent press textiles.

In the early 1970s, a process was developed by Mobil for producing gasoline fuel for vehicles. One such industrial facility was built at Motunui in New Zealand in the 1980s. In the 1990s, large amounts of methanol were used in the United States to produce the gasoline additive methyl tert-butyl ether (MTBE). While MTBE is no longer marketed in the U.S., it is still widely used in other parts of the world. Methanol (or less commonly, ethanol) is a component in the transesterification of triglycerides for production of biodiesel.

Other chemical derivatives of methanol include dimethyl ether (DME), which has replaced chlorofluorocarbons as an aerosol spray propellant, and acetic acid. Dimethyl ether can be blended with liquified petroleum gas (LPG) for home heating and cooking, and can be used as a replacement for transportation diesel fuel.

Of high interest to the petrochemical marketplace, methanol is an important ingredient in new and lower-cost methods for producing propylene, which is much in demand. Such methods include Methanol-to-Olefins (MTO), Methanol-to-Propylene (MTO/MTP), Metathesis, Propane Dehydrogenation (PDH), High Severity FCC, and Olefins Cracking.

The market for proponyl became tight when the ethane prices fell in the USA with the exploration of shale gas reserves. The low priced ethylene produced from this raw material has given chemical producers in North America a feedstock advantage. Such change has put naphtha-fed steam crackers at a disadvantageous position, with many of them shutting down or revamping to use ethane as feedstock. Nevertheless, the propylene output rates from ethane-fed crackers are negligible.[18]

Fuel for vehicles

Main articles: Methanol fuel and methanol economy

Methanol is occasionally used to fuel internal combustion engines. Pure methanol is required by rule to be used in Champcars, Monster Trucks, USAC sprint cars (as well as midgets, modifieds, etc.), and other dirt track series, such as World of Outlaws, and Motorcycle Speedway, mainly because, in the event of an accident, methanol does not produce an opaque cloud of smoke. Since the late 1940s, Methanol is also used as the primary fuel ingredient in the powerplants for radio control, control line, free flight airplanes, cars and trucks; such engines use a platinum filament glow plug that ignites the methanol vapor through a catalytic reaction. Drag racers, mud racers, and heavily modified tractor pullers also use methanol as the primary fuel source. Methanol is required with a supercharged engine in a Top Alcohol Dragster and, until the end of the 2006 season, all vehicles in the Indianapolis 500 had to run on methanol. As a fuel for mud racers, methanol mixed with gasoline and nitrous oxide produces more power than gasoline and nitrous oxide alone.

Methanol burns in oxygen, including open air, forming carbon dioxide and water:

2 CH3OH + 3 O2 → 2 CO2 + 4 H2O

One problem with high concentrations of methanol in fuel is that alcohols corrode some metals, particularly aluminium. An acid, albeit weak, methanol attacks the oxide coating that normally protects the aluminum from corrosion:

6 CH3OH + Al2O3 → 2 Al(OCH3)3 + 3 H2O

The resulting methoxide salts are soluble in methanol, resulting in a clean aluminium surface, which is readily oxidized by dissolved oxygen. Also, the methanol can act as an oxidizer:

6 CH3OH + 2 Al → 2 Al(OCH3)3 + 3 H2

This reciprocal process effectively fuels corrosion until either the metal is eaten away or the concentration of CH3OH is negligible. Methanol's corrosivity has been addressed with methanol-compatible materials and fuel additives that serve as corrosion inhibitors.

Organic methanol, produced from wood or other organic materials (bioalcohol), has been suggested as a renewable alternative to petroleum-based hydrocarbons. Low levels of methanol can be used in existing vehicles with the addition of cosolvents and corrosion inhibitors.

Methanol fuel has been proposed for ground transportation. The chief advantage of a methanol economy is that it could be adapted to gasoline internal combustion engines with minimum modification to the engines and to the infrastructure that delivers and stores liquid fuel.

Safety in automotive fuels

Pure methanol has been used in open wheel auto racing since the mid-1960s. Unlike petroleum fires, methanol fires can be extinguished with plain water. A methanol-based fire burns invisibly, unlike gasoline, which burns with a visible flame. If a fire occurs on the track, there is no flame or smoke to obstruct the view of fast approaching drivers, but this can also delay visual detection of the fire and the initiation of fire suppression. The decision to permanently switch to methanol in American IndyCar racing was a result of the devastating crash and explosion at the 1964 Indianapolis 500, which killed drivers Eddie Sachs and Dave MacDonald.[19] In 2007 IndyCars switched from methanol to ethanol.[20]

Government policy

The European Fuel Quality Directive allows up to 3% methanol with an equal amount of cosolvent to be blended with gasoline sold in Europe. China uses more than one billion gallons of methanol per year as a transportation fuel in low level blends for conventional vehicles and high level blends in vehicles designed for methanol fuels.

In the US, the Open Fuel Standard Act of 2011 was introduced in the US Congress to encourage car manufacturers to build cars capable of using methanol, gasoline, or ethanol fuels. The bill is being championed by the Open Fuel Standard Coalition.

Production of synthesis gas

Stoichiometry for methanol production of syngas requires the ratio of H2 / CO to equal 2. The partial oxidation process yields a ratio of 2, and the steam reforming process yields a ratio of 3. The H2 / CO ratio can be lowered to some extent by the reverse water-gas shift reaction,

CO2 + H2 → CO + H2O,

to provide the appropriate stoichiometry for methanol synthesis.

Energy carrier

Methanol is useful as an energy carrier because it is easier to store than hydrogen and burns cleaner than fossil fuels.

Methanol is readily biodegradable in both aerobic (oxygen present) and anaerobic (oxygen absent) environments. Methanol will not persist in the environment. The half-life for methanol in groundwater is just one to seven days, while many common gasoline components have half-lives in the hundreds of days (such as benzene at 10–730 days). Since methanol is miscible with water and biodegradable, it is unlikely to accumulate in groundwater, surface water, air or soil.[21]

Other applications

Methanol is a traditional denaturant for ethanol, the product being known as "denatured alcohol" or "methylated spirit". This was commonly used during the Prohibition to discourage consumption of bootlegged liquor, and ended up causing several deaths.[22]

Methanol is used as a solvent and as an antifreeze in pipelines and windshield washer fluid.

In some wastewater treatment plants, a small amount of methanol is added to wastewater to provide a carbon food source for the denitrifying bacteria, which convert nitrates to nitrogen gas and reduce the nitrification of sensitive aquifers.

During World War II, methanol was used as a fuel in several German military rocket designs, under the name M-Stoff, and in a roughly 50/50 mixture with hydrazine, known as C-Stoff.

Methanol was used as an automobile coolant antifreeze in the early 1900s.[23]

Methanol is used as a destaining agent in polyacrylamide gel electrophoresis.

Direct-methanol fuel cells are unique in their low temperature, atmospheric pressure operation, allowing them to be miniaturized to an unprecedented degree.[24][25] This, combined with the relatively easy and safe storage and handling of methanol, may open the possibility of fuel cell-powered consumer electronics, such as laptop computers and mobile phones.[26]

Methanol is also a widely used fuel in camping and boating stoves. Methanol burns well in an unpressurized burner, so alcohol stoves are often very simple, sometimes little more than a cup to hold fuel. This lack of complexity makes them a favorite of hikers who spend extended time in the wilderness. Similarly, the alcohol can be gelled to reduce risk of leaking or spilling, as with the brand "Sterno".

Methanol is mixed with water and injected into high performance diesel and gasoline engines for an increase of power and a decrease in intake air temperature in a process known as water methanol injection.

Production

Human metabolite

Small amounts of methanol is a natural endogenous compound found in normal, healthy humans. A study found a mean of 4.5 ppm in the exhaled breath of subjects.[27] The mean endogenous methanol production in humans of 0.45 g/d may be metabolized from pectin found in fruit; one kilogram of apple produces up to 1.4 g methanol.[28]

From synthesis gas

Carbon monoxide and hydrogen react over a catalyst to produce methanol. Today, the most widely used catalyst is a mixture of copper and zinc oxides, supported on alumina, as first used by ICI in 1966. At 5–10 MPa (50–100 atm) and 250 °C (482 °F), the reaction is characterized by high selectivity (>99.8%):

CO + 2 H2 → CH3OH

Since the production of synthesis gas from methane produces three moles of hydrogen for every mole of carbon monoxide, whereas the synthesis consumes only two moles of hydrogen gas per mole of carbon monoxide. One way of dealing with the excess hydrogen is to inject carbon dioxide into the methanol synthesis reactor, where it, too, reacts to form methanol according to the equation:

CO2 + 3 H2 → CH3OH + H2O

In terms of mechanism, the process occurs via initial conversion of CO into CO2, which is then hydrogenated:[29]

CO2 + 3 H2 → CH3OH + H2O

where the H2O byproduct is recycled via the water-gas shift reaction

CO + H2O → CO2 + H2,

This gives an overall reaction, which is the same as listed above.

CO + 2 H2 → CH3OH

Other

The catalytic conversion of methane to methanol has long been sought as a route to methanol. This route is effected by enzymes such as methane monooxygenases but commercial routes remain elusive because of the tendency for over-oxidation, i.e., methanol is more readily oxidized than is methane.[30][31]

Quality specifications and analysis

Laboratory use

Methanol is available commercially in various purity grades for fine chemicals:

Commercial methanol

In addition to laboratory grades, commercial methanol is generally classified according to ASTM purity grades A and AA. Methanol for chemical use normally corresponds to Grade AA. In addition to water, typical impurities include acetone and ethanol (which are very difficult to separate by distillation). When methanol is delivered by ships or tankers used to transport other substances, contamination by the previous cargo must be expected. Comparative ultraviolet spectroscopy has proved a convenient, quick test method for deciding whether a batch can be accepted and loaded. Traces of all chemicals derived from aromatic parent substances, as well as a large number of other compounds, can be detected. Further tests for establishing the quality of methanol include measurements of boiling point range, density, permanganate number, turbidity, color index, and acid number. More comprehensive tests include water determination according to the Karl Fischer method and gas chromatographic determination of byproducts. However, the latter is relatively expensive and time-consuming because several injections using different columns and detectors must be made due to the variety of byproducts present.

History

In their embalming process, the ancient Egyptians used a mixture of substances, including methanol, which they obtained from the pyrolysis of wood. Pure methanol, however, was first isolated in 1661 by Robert Boyle, when he produced it via the distillation of buxus (boxwood).[32] It later became known as "pyroxylic spirit". In 1834, the French chemists Jean-Baptiste Dumas and Eugene Peligot determined its elemental composition.[33]

They also introduced the word "methylene" to organic chemistry, forming it from Greek methy = "alcoholic liquid" + hȳlē = wood (patch of trees), with Greek language errors: "wood (substance)" (Greek ξύλον, xylon) was intended, and the components are in the wrong order for Greek. The term "methyl" was derived in about 1840 by back-formation from "methylene", and was then applied to describe "methyl alcohol". This was shortened to "methanol" in 1892 by the International Conference on Chemical Nomenclature.[34] The suffix -yl used in organic chemistry to form names of carbon groups, was extracted from the word "methyl".

In 1923, the German chemists Alwin Mittasch and Mathias Pier, working for Badische-Anilin & Soda-Fabrik(BASF), developed a means to convert synthesis gas (a mixture of carbon monoxide, carbon dioxide, and hydrogen) into methanol. US patent 1,569,775 was applied for on 4 Sep 1924 and issued on 12 January 1926; the process used a chromium and manganese oxide catalyst with extremely vigorous conditions—pressures ranging from 50 to 220 atm, and temperatures up to 450 °C. Modern methanol production has been made more efficient through use of catalysts (commonly copper) capable of operating at lower pressures. The modern low pressure methanol (LPM) was developed by ICI in the late 1960s US 3326956  with the technology now owned by Johnson Matthey, which is a leading licensor of methanol technology.

Methanol is one of the most heavily traded chemical commodities in the world, with an estimated global demand of around 27 to 29 million metric tons. In recent years, production capacity has expanded considerably, with new plants coming on-stream in South America, China and the Middle East, the latter based on access to abundant supplies of methane gas. Even though nameplate production capacity (coal-based) in China has grown significantly, operating rates are estimated to be as low as 50 to 60%. No new production capacity is scheduled to come on-stream until 2015.

The main applications for methanol are the production of formaldehyde (used in construction and wooden boarding), acetic acid (basis for a.o. PET-bottles), MTBE (fuel component and replacement for the very volatile diethyl ether) and more recently for the formation of methyl esters in the production of bio-diesel. In China, demand is expected to grow exponentially, not only caused by a growing internal market of the traditional applications, but accelerated by new applications, such as direct blending (with gasoline), Methanol-To-Olefins (e.g. propylene) and DME. Methanol can also be used to produce gasoline.

Artist’s impression of the disc around the young star TW Hydrae.[35]

The use of methanol as a motor fuel received attention during the oil crises of the 1970s due to its availability, low cost, and environmental benefits. By the mid-1990s, over 20,000 methanol "flexible fuel vehicles" capable of operating on methanol or gasoline were introduced in the U.S. In addition, low levels of methanol were blended in gasoline fuels sold in Europe during much of the 1980s and early-1990s. Automakers stopped building methanol FFVs by the late-1990s, switching their attention to ethanol-fueled vehicles. While the methanol FFV program was a technical success, rising methanol pricing in the mid- to late-1990s during a period of slumping gasoline pump prices diminished the interest in methanol fuels.[36]

In 2006, astronomers using the MERLIN array of radio telescopes at Jodrell Bank Observatory discovered a large cloud of methanol in space, 288 billion miles across.[37][38] In 2016, astronomers detected methyl alcohol in a planet-forming disc around the young star TW Hydrae using ALMA radio telescope.[39]

See also

References

  1. ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 692. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ↑ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. ISBN 0-8493-0486-5.
  3. ↑ Ballinger, P.; Long, F.A. (1960). "Acid Ionization Constants of Alcohols. II. Acidities of Some Substituted Methanols and Related Compounds". J. Am. Chem. Soc. 82 (4): 795–798. doi:10.1021/ja01489a008.
  4. ↑ Refractive index of Methanol, CH3OH (MeOH) [LIQUIDS] – RefractiveIndex.INFO
  5. ↑ González, Begoña (2007). "Density, dynamic viscosity, and derived properties of binary mixtures of methanol or ethanol with water, ethyl acetate, and methyl acetate at T = (293.15, 298.15, and 303.15) K". The Journal of Chemical Thermodynamics. 39 (12): 1578–1588. doi:10.1016/j.jct.2007.05.004.
  6. ↑ "The Emergency Response Safety and Health Database: Systematic Agent: METHANOL". Centers for Disease Control and Prevention. Retrieved 26 August 2009.
  7. 1 2 3 4 "Methanol" (PDF). Lab Chem. Valtech. Retrieved 10 March 2016.
  8. ↑ http://www.methanol.org/Health-And-Safety/Safety-Resources/Health---Safety/Methanex-TISH-Guide.aspx
  9. 1 2 3 4 "NIOSH Pocket Guide to Chemical Hazards #0397". National Institute for Occupational Safety and Health (NIOSH).
  10. 1 2 3 "Methanol". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
  11. ↑ National Institute for Occupational Safety and Health (22 August 2008). "The Emergency Response Safety and Health Database: Methanol". Retrieved 17 March 2009.
  12. ↑ Brooks Hays (17 April 2015). "Why astronomers hate the lawn-mowing Roomba". Space Daily.
  13. ↑ Barceloux, DG; Bond, GR; Krenzelok, EP; Cooper, H; Vale, JA; American Academy of Clinical Toxicology Ad Hoc Committee on the Treatment Guidelines for Methanol, Poisoning (2002). "American Academy of Clinical Toxicology practice guidelines on the treatment of methanol poisoning.". Journal of toxicology. Clinical toxicology. 40 (4): 415–46. PMID 12216995.
  14. 1 2 3 4 5 6 Kruse, JA (October 2012). "Methanol and ethylene glycol intoxication.". Critical care clinics. 28 (4): 661–711. PMID 22998995.
  15. 1 2 3 4 5 6 7 8 Beauchamp, GA; Valento, M (September 2016). "Toxic Alcohol Ingestion: Prompt Recognition And Management In The Emergency Department.". Emergency medicine practice. 18 (9): 1–20. PMID 27538060.
  16. ↑ Ferri, Fred F. (2016). Ferri's Clinical Advisor 2017: 5 Books in 1. Elsevier Health Sciences. p. 794. ISBN 9780323448383.
  17. ↑ Clary, John J. (2013). The Toxicology of Methanol. John Wiley & Sons. p. 3.4.1. ISBN 9781118353103.
  18. ↑ "Propylene Production from Methanol". by Intratec, ISBN 978-0-615-64811-8.
  19. ↑ McDonald, Norris (21 April 2007). "Green no longer bad luck at Indy". Toronto Star. Retrieved 12 May 2010.
  20. ↑ "IndyCar Series Teams Begin Use of Ethanol-Blended Fuel". Indycar.com. 1 December 2005. Retrieved 7 November 2010.
  21. ↑ Evaluation of the Fate and Transport of Methanol in the Environment, Malcolm Pirnie, Inc., January 1999.
  22. ↑ Blum, Deborah (19 February 2010). "The little-told story of how the U.S. government poisoned alcohol during Prohibition". Slate Magazine. Retrieved 10 June 2010.
  23. ↑ Yant, W. P.; Schrenk, H. H.; Sayers, R. R. (1931). "Methanol Antifreeze and Methanol Poisoning". Industrial & Engineering Chemistry. 23 (5): 551. doi:10.1021/ie50257a020.
  24. ↑ Kamitani, A.; Morishita, S.; Kotaki, H.; Arscott, S. (2008). "Miniaturized microDMFC using silicon microsystems techniques: Performances at low fuel flow rates". Journal of Micromechanics and Microengineering. 18 (12): 125019. doi:10.1088/0960-1317/18/12/125019.
  25. ↑ Kamitani, A.; Morishita, S.; Kotaki, H.; Arscott, S. (2011). "Microfabricated microfluidic fuel cells". Sensors and Actuators B: Chemical. 154 (2): 174. doi:10.1016/j.snb.2009.11.014.
  26. ↑ Berger, Sandy (30 September 2006). "Methanol Laptop Fuel". Compu·Kiss. Retrieved 22 May 2007.
  27. ↑ Turner, C; Spanel, P; Smith, D (2006). "A longitudinal study of methanol in the exhaled breath of 30 healthy volunteers using selected ion flow tube mass spectrometry, SIFT-MS". Physiological Measurement. 27 (7): 637–48. doi:10.1088/0967-3334/27/7/007. PMID 16705261.
  28. ↑ Lindinger, W; Taucher, J; Jordan, A; Hansel, A; Vogel, W (1997). "Endogenous production of methanol after the consumption of fruit". Alcoholism: Clinical and Experimental Research. 21 (5): 939–43. doi:10.1111/j.1530-0277.1997.tb03862.x. PMID 9267548.
  29. ↑ Olaf Deutschmann, Helmut Knözinger, Karl Kochloefl, Thomas Turek "Heterogeneous Catalysis and Solid Catalysts, 3. Industrial Applications" in Ullmann's Encyclopedia of Industrial Chemistry" 2012, Wiley-VCH, Weinheim. doi:10.1002/14356007.o05_o03
  30. ↑ Alayon, E. M. C.; Nachtegaal, M.; Ranocchiari, M.; Van Bokhoven, J. A. (2012). "Catalytic Conversion of Methane to Methanol Using Cu-Zeolites". CHIMIA International Journal for Chemistry. 66 (9): 668–674. doi:10.2533/chimia.2012.668. PMID 23211724.
  31. ↑ Hammond, C.; Jenkins, R. L.; Dimitratos, N.; Lopez-Sanchez, J. A.; Ab Rahim, M. H.; Forde, M. M.; Thetford, A.; Murphy, D. M.; Hagen, H.; Stangland, E. E.; Moulijn, J. M.; Taylor, S. H.; Willock, D. J.; Hutchings, G. J. (2012). "Catalytic and Mechanistic Insights of the Low-Temperature Selective Oxidation of Methane over Cu-Promoted Fe-ZSM-5". Chemistry: A European Journal. 18 (49): 15735. doi:10.1002/chem.201202802. PMID 23150452.
  32. ↑ Boyle discusses the distillation of liquids from the wood of the box shrub in: Robert Boyle, The Sceptical Chymist (London, England: J. Cadwell, 1661), pp. 192–195.
  33. ↑ A report on methanol to the French Academy of Sciences by J. Dumas and E. Péligot began during the Academy's meeting of October 27, 1834 and finished during the meeting of November 3, 1834. See: Procès-verbaux des séances de l'Académie, 10 : 600–601. Available on: Gallica. The complete report appears in: J. Dumas and E. Péligot (1835) "Mémoire sur l'espirit de bois et sur les divers composés ethérés qui en proviennent" (Memoir on spirit of wood and on the various ethereal compounds that derive therefrom), Annales de chimie et de physique, 58 : 5–74; from page 9: Nous donnerons le nom de méthylène (1) à un radical … (1) Μεθυ, vin, et υλη, bois; c'est-à-dire vin ou liqueur spiritueuse du bois. (We will give the name "methylene" (1) to a radical … (1) methy, wine, and hulē, wood; that is, wine or spirit of wood.)
  34. ↑ For a report on the International Conference on Chemical Nomenclature that was held in April 1892 in Geneva, Switzerland, see:
  35. ↑ "Artist's impression of the disc around the young star TW Hydrae". Retrieved 22 June 2016.
  36. ↑ Halderman, James D.; Martin, Tony (2009). Hybrid and alternative fuel vehicles. Pearson/Prentice Hall. ISBN 978-0-13-504414-8.
  37. ↑ "Upgraded MERLIN spies cloud of alcohol spanning 288 billion miles" (Press release). Jodrell Bank Centre for Astrophysics. 19 April 2006.
  38. ↑ Amos, Jonathan (5 April 2006). "Merlin sees vast alcohol stream". BBC News.
  39. ↑ "First Detection of Methyl Alcohol in a Planet-forming Disc". Retrieved 22 June 2016.

Further reading

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