Methanol, also known as methyl alcohol among others, is a chemical
with the formula CH3OH (often abbreviated MeOH).
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.
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). However, unlike ethanol, methanol is highly toxic and
unfit for consumption. At room temperature, it is a polar liquid. It
is used as an antifreeze, solvent, fuel, and as a denaturant for
ethanol. It is also used for producing biodiesel by
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. However, in only a few days, atmospheric methanol is
oxidized by sunlight to produce carbon dioxide and water.
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.
when drunk is metabolized first to formaldehyde and then to
formic acid or formate salts. 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.
1.1 Human metabolite
3.1 Chemical industry
Fuel for vehicles
3.2.1 Usage in the production of biodiesel
3.2.2 Safety in automotive fuels
3.2.3 Government policy
3.3 Production of synthesis gas
3.4 Energy carrier
3.5 Other applications
4.1 From synthesis gas
5 Quality specifications and analysis
5.1 Laboratory use
5.2 Commercial methanol
7 See also
9 Further reading
10 External links
Methanol is poisonous to the central nervous system and may cause
blindness, coma, and death. However, in small amounts, methanol is a
natural endogenous compound found in normal, healthy human
individuals, concluded by one study which found a mean of 4.5 ppm
in the exhaled breath of subjects. The mean endogenous methanol 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.
See also: List of methanol poisoning incidents
Methanol has a high toxicity in humans. As little as 10 mL of
pure methanol, ingested, is metabolized into formic acid, which can
cause permanent blindness by destruction of the optic nerve.
30 mL is potentially fatal, although the median lethal dose
is typically 100 mL (3.4 fl oz) (i.e. 1–2 mL/kg
body weight of pure methanol). The reference dose for methanol is
2 mg/kg in a day.
Toxic effects begin hours after
ingestion, and antidotes can often prevent permanent damage.
Because of its similarities in both appearance and odor to ethanol
(the alcohol in beverages), it is difficult to differentiate between
the two (such is also the case with denatured alcohol, adulterated
liquors or very low quality alcoholic beverages). However, there are
cases of methanol resistance, such as that of Mike Malloy who was the
victim of a failed murder attempt by methanol in the early 1930s.
Methanol is toxic by two mechanisms. First, methanol (whether it
enters the body by ingestion, inhalation, or absorption through the
skin) can be fatal due to its
CNS depressant properties in the same
manner as ethanol poisoning. Second, in a process of toxication, it is
metabolized to formic acid (which is present as the formate ion) via
formaldehyde in a process initiated by the enzyme alcohol
dehydrogenase in the liver.
Methanol is converted to formaldehyde
via alcohol dehydrogenase (ADH) and formaldehyde is converted to
formic acid (formate) via aldehyde dehydrogenase (ALDH). The
conversion to formate via ALDH proceeds completely, with no detectable
Formate is toxic because it inhibits
mitochondrial cytochrome c oxidase, causing hypoxia at the cellular
level, and metabolic acidosis, among a variety of other metabolic
Outbreaks of methanol poisoning have occurred due to contamination of
drinking alcohol. This is more common in the developing world. In
2013 more than 1700 cases occurred in the United States. Those
affected are often adult males. Outcomes may be good with early
treatment. Toxicity to methanol was described as early as
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 denaturing agent. As a common laboratory polar solvent,
methanol is especially useful for HPLC, UV/VIS spectroscopy, and LCMS
due to its low UV cutoff.
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
Condensation of methanol molecules to produce hydrocarbon chains and
even aromatic systems has been demonstrated with loss of water, carbon
monoxide, and/or carbon dioxide (loss of oxygen is prohibited on
thermodynamic grounds). As early as 1880, an aromatisation reaction
which generated hexamethylbenzene as a minor product with a mixture of
mostly aliphatic hydrocarbons directly from methanol, using zinc
chloride as catalyst, had been demonstrated. At 283 °C,
the melting point of ZnCl2, the idealised reaction for the production
of hexamethylbenzene has a ΔG of −261 kcal mol−1.
3OH → C
6 + 3 CH
4 + 15 H
In the early 1970s, a process was developed by
Mobil for producing
gasoline fuel for vehicles. One such industrial facility was built
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
Methanol (or less commonly, ethanol) is a component in the
transesterification of triglycerides for production of biodiesel.
Other chemical derivatives of methanol include acetic acid and
dimethyl ether (DME), the latter of which has replaced
chlorofluorocarbons as an aerosol spray propellant.
Dimethyl ether can
also be blended with liquified petroleum gas (LPG) for home heating
and cooking, and can be used as a replacement for transportation
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
The market for propynyl became tight when the ethane prices fell in
the US 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
Fuel for vehicles
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
Methanol is required with a supercharged engine in a Top
Alcohol Dragster and, until the end of the 2006 season, all vehicles
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
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
aluminium 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
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
Usage in the production of biodiesel
Methanol (and some other alcohols) can be used with a catalyse (such
as Sodium hydroxide) to convert plant and animal oil or fat into
biodiesel and glycerol in a process called the transesterification
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. In 2007
IndyCars switched from methanol to ethanol.
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
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.
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.
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.
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
Methanol is used as a destaining agent in polyacrylamide gel
Direct-methanol fuel cells are unique in their low temperature,
atmospheric pressure operation, allowing them to be miniaturized to an
unprecedented degree. 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
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.
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
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:
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
The catalytic conversion of methane to methanol is effected by enzymes
including methane monooxygenases. These enzymes are mixed-function
oxygenases, i.e. oxygenation is coupled with production of water:
CH4 + O2 + NADPH + H+ → CH3OH + H2O + NAD+
Both Fe- and Cu-dependent enzymes have been characterized. Intense
efforts have been undertaken to emulate this reactivity.
Methanol is more easily oxidized than is the feedstock methane, so the
reactions tend not to be selective.
Quality specifications and analysis
Methanol is available commercially in various purity grades for fine
"Synthesis" quality (corresponding to normal commercial methanol)
Certified analytical quality
Extremely pure qualities for semiconductor manufacture
In addition to laboratory grades, commercial methanol is generally
classified according to ASTM purity grades A and AA.
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.
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). It later became known as "pyroxylic spirit". In 1834,
the French chemists
Jean-Baptiste Dumas and
Eugene Peligot determined
its elemental composition.
They also introduced the word "methylène" to organic chemistry,
forming it from Greek methy = "alcoholic liquid" + hȳlē = "woodland,
forest", with a
Greek language error: xylon = "wood as a material"
would have been more suitable. "Methylène" designated a "radical"
that was about 14% hydrogen by weight and contained one carbon atom.
This would be CH2, but at the time carbon was thought to have an
atomic weight only six times that of hydrogen, so they gave the
formula as CH. They then called wood alcohol (l'esprit de bois)
"bihydrate de méthylène" (bihydrate because they thought the formula
was C4H8O4 = (CH)4(H2O)2!). 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. 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)
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
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-
propylene) and DME.
Methanol can also be used to produce gasoline.
Artist’s impression of the disc around the young star TW Hydrae.
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.
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. In 2016, astronomers detected
methyl alcohol in a planet-forming disc around the young star TW
Hydrae using ALMA radio telescope.
Methanol (data page)
^ 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.
^ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th
ed.). Boca Raton (FL): CRC Press. ISBN 0-8493-0486-5.
^ Ballinger, P.; Long, F. A. (1960). "Acid Ionization Constants of
Alcohols. II. Acidities of Some Substituted Methanols and Related
J. Am. Chem. Soc. 82 (4): 795–798.
^ "RefractiveIndex.INFO -
Refractive index database".
^ 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.
^ a b c d "Methanol" (PDF). Lab Chem. Valtech. Retrieved 10 March
^ "METHANOL INSTITUTE". Archived from the original on 11 March
^ a b c d "NIOSH Pocket Guide to Chemical Hazards #0397". National
Institute for Occupational Safety and Health (NIOSH).
^ a b c "Methanol". Immediately Dangerous to Life and Health
Concentrations (IDLH). National Institute for Occupational Safety and
^ "The Emergency Response Safety and Health Database: Systematic
Agent: METHANOL". Centers for Disease Control and Prevention.
Retrieved 26 August 2009.
National Institute for Occupational Safety and Health
National Institute for Occupational Safety and Health (22 August
2008). "The Emergency Response Safety and Health Database: Methanol".
Retrieved 17 March 2009.
^ Brooks Hays (17 April 2015). "Why astronomers hate the lawn-mowing
Roomba". Space Daily.
^ Barceloux, D. G.; Bond, G. R.; Krenzelok, E. P.; Cooper, H.; Vale,
J. A.; 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.
^ Turner C. "A longitudinal study of methanol in the exhaled breath of
30 healthy volunteers using selected ion flow tube mass spectrometry,
SIFT-MS". PMID 16705261. Missing or empty url= (help)
^ Lindinger W. "Endogenous production of methanol after the
consumption of fruit". PMID 9267548. Missing or empty url=
^ a b Vale A (2007). "Methanol". Medicine. 35 (12): 633–4.
Methanol Poisoning Overview". Antizol. Archived from the original
on 5 October 2011.
^ "Integrated Risk Information System". US EPA, ORD, NCEA,
^ "Toxicological Review of
Methanol (Noncancer) (CAS No. 67-56-1) In
Support of Summary Information on the Integrated Risk Information
System (IRIS)" (PDF). EPA. September 2013. EPA/635/R-11/001Fa.
Retrieved 4 September 2017.
^ Blum, Deborah (January 2011). The Poisoner's Handbook: Murder and
the Birth of Forensic Medicine in Jazz Age New York. Penguin Books.
p. 231. ISBN 978-0-14-311882-4.
^ Schep LJ, Slaughter RJ, Vale JA, Beasley DM (2009). "A seaman with
blindness and confusion". BMJ. 339: b3929. doi:10.1136/bmj.b3929.
^ McMartin KE, Martin-Amat G, Noker PE, Tephly TR (1979). "Lack of a
role for formaldehyde in methanol poisoning in the monkey". Biochem.
Pharmacol. 28 (5): 645–9. doi:10.1016/0006-2952(79)90149-7.
^ Liesivuori J, Savolainen H (September 1991). "
Methanol and formic
acid toxicity: biochemical mechanisms". Pharmacol. Toxicol. 69 (3):
^ Beauchamp, GA; Valento, M (September 2016). "
Ingestion: Prompt Recognition And Management In The Emergency
Department". Emergency medicine practice. 18 (9): 1–20.
^ Ferri, Fred F. (2016). Ferri's Clinical Advisor 2017: 5 Books in 1.
Elsevier Health Sciences. p. 794. ISBN 9780323448383.
^ Kruse, JA (October 2012). "
Methanol and ethylene glycol
intoxication". Critical care clinics. 28 (4): 661–711.
doi:10.1016/j.ccc.2012.07.002. PMID 22998995.
^ Clary, John J. (2013). The Toxicology of Methanol. John Wiley &
Sons. p. 3.4.1. ISBN 9781118353103.
^ a b c Chang, Clarence D. (1983). "Hydrocarbons from Methanol".
Catal. Rev. - Sci. Eng. 25 (1): 1–118.
^ Olah, George A.; Doggweiler, Hans; Felberg, Jeff D.; Frohlich,
Stephan; Grdina, Mary Jo; Karpeles, Richard; Keumi, Takashi; Inaba,
Shin-ichi; Ip, Wai M.; Lammertsma, Koop; Salem, George; Tabor, Derrick
(1984). "Onium Ylide chemistry. 1. Bifunctional acid-base-catalyzed
conversion of heterosubstituted methanes into ethylene and derived
hydrocarbons. The onium ylide mechanism of the C1 → C2 conversion".
J. Am. Chem. Soc. 106 (7): 2143–2149. doi:10.1021/ja00319a039.
Propylene Production from Methanol". by Intratec,
Biodiesel - METHANOL INSTITUTE". METHANOL INSTITUTE. Retrieved
Biodiesel Production Principles and Processes - eXtension".
^ McDonald, Norris (21 April 2007). "Green no longer bad luck at
Indy". Toronto Star. Retrieved 12 May 2010.
^ "IndyCar Series Teams Begin Use of Ethanol-Blended Fuel".
Indycar.com. 1 December 2005. Archived from the original on 14 May
2010. Retrieved 7 November 2010.
^ Evaluation of the Fate and Transport of
Methanol in the Environment
Archived 16 May 2016 at the Portuguese Web Archive, Malcolm Pirnie,
Inc., January 1999.
^ 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.
^ Yant, W. P.; Schrenk, H. H.; Sayers, R. R. (1931). "Methanol
Methanol Poisoning". Industrial & Engineering
Chemistry. 23 (5): 551. doi:10.1021/ie50257a020.
^ 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. Bibcode:2008JMiMi..18l5019K.
^ 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.
^ Berger, Sandy (30 September 2006). "
Methanol Laptop Fuel".
Compu·Kiss. Retrieved 22 May 2007.
^ Olaf Deutschmann, Helmut Knözinger, Karl Kochloefl, Thomas Turek
Catalysis and Solid Catalysts, 3. Industrial
Applications" in Ullmann's Encyclopedia of Industrial Chemistry" 2012,
Wiley-VCH, Weinheim. doi:10.1002/14356007.o05_o03
^ Mu-Hyun Baik, Martin Newcomb, Richard A. Friesner, Stephen J.
Lippard (2003). "Mechanistic Studies on the Hydroxylation of Methane
Methane Monooxygenase". Chem. Rev. 103: 2385–2420.
doi:10.1021/cr950244f. CS1 maint: Uses authors parameter (link)
^ Lawton, T. J.; Rosenzweig, A. C. (2016). "Biocatalysts for methane
conversion: big progress on breaking a small substrate". Curr. Opin.
Chem. Biol. 35: 142–149. doi:10.1016/j.cbpa.2016.10.001. CS1
maint: Uses authors parameter (link)
^ Alayon, E. M. C.; Nachtegaal, M.; Ranocchiari, M.; Van Bokhoven, J.
A. (2012). "Catalytic Conversion of
Cu-Zeolites". CHIMIA International Journal for Chemistry. 66 (9):
668–674. doi:10.2533/chimia.2012.668. PMID 23211724.
^ 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.
^ Boyle discusses the distillation of liquids from the wood of the box
shrub in: Robert Boyle,
The Sceptical Chymist
The Sceptical Chymist (London, England: J.
Cadwell, 1661), pp. 192–195.
^ a b 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.)
^ For a report on the International Conference on Chemical
Nomenclature that was held in April 1892 in Geneva, Switzerland, see:
Armstrong, Henry E (1892). "The International Conference on Chemical
Nomenclature". Nature. 46 (1177): 56–9. Bibcode:1892Natur..46...56A.
Armstrong's report is reprinted with the resolutions in English in:
Armstrong, Henry (1892). "The International Conference on Chemical
Nomenclature". The Journal of Analytical and Applied Chemistry. 6:
390–400. p. 398: 15. The alcohols and the phenols will be called
after the name of the hydrocarbon from which they are derived,
terminated with the suffix ol (ex. pentanol, pentenol, etc.).
^ "Artist's impression of the disc around the young star TW Hydrae".
Retrieved 22 June 2016.
^ Halderman, James D.; Martin, Tony (2009). Hybrid and alternative
fuel vehicles. Pearson/Prentice Hall.
MERLIN spies cloud of alcohol spanning 288 billion miles"
Jodrell Bank Centre for Astrophysics. 19 April 2006.
Archived from the original on 20 July 2011.
^ Amos, Jonathan (5 April 2006). "Merlin sees vast alcohol stream".
^ "First Detection of Methyl
Alcohol in a Planet-forming Disc".
Retrieved 22 June 2016.
The Sceptical Chymist
The Sceptical Chymist (1661) – contains account of
distillation of wood alcohol.
International Chemical Safety Card 0057
Alcohol (Methanol) CDC/NIOSH, links to safety information
CDC – NIOSH Pocket Guide to Chemical Hazards – Methyl Alcohol
Methanol Fact Sheet – National Pollutant Inventory
Cetyl alcohol (C
Stearyl alcohol (C
Arachidyl alcohol (C
Isoamyl alcohol (C
Phenethyl alcohol (C
tert-Butyl alcohol (C
tert-Amyl alcohol (C
Ethylene glycol
Deoxy sugar alcohols
Cyclic sugar alcohols
Spooky toxin (SsTx)
Glued laminated timber
Oriented strand board
Oriented structural straw board
Structural insulated panel
Ramial chipped wood
List of woods
Non-timber forest products
Molecules detected in outer space
Magnesium monohydride cation
Hydrogen cyanide (HCN)
Hydrogen isocyanide (HNC)
Protonated molecular hydrogen
Protonated carbon dioxide
Protonated hydrogen cyanide
Buckminsterfullerene (C60 fullerene, buckyball)
Ethyl methyl ether
Atomic and molecular astrophysics
Diffuse interstellar band
Earliest known life forms
Extraterrestrial liquid water
Helium hydride ion
Iron–sulfur world theory
Molecules in stars
Nexus for Exoplanet System Science
PAH world hypothesis
Polycyclic aromatic hydrocarbon
Polycyclic aromatic hydrocarbon (PAH)
RNA world hypothesis
GABAA receptor positive modulators
Ethanol (alcohol) (alcoholic drink)
Skullcap constituents (e.g., baicalin)
Certain anabolic-androgenic steroids
Acetylglycinamide chloral hydrate
Trichloroethane (methyl chloroform)
Avermectins (e.g., ivermectin)
Bromide compounds (e.g., lithium bromide, potassium bromide, sodium
Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine,
dihydroergotamine, ergoloid (dihydroergotoxine))
Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid,
Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol)
Menthyl isovalerate (validolum)
Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional)
Terpenoids (e.g., borneol)
Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic
Unsorted benzodiazepine site positive modulators: α-Pinene
See also: Receptor/signaling modulators • GABA receptor modulators
• GABA metabolism/transport modulators