METHANOL

CAS Number: 67-56-1
EC Number: 200-659-6
Chemical Formula: CH3OH
Molar Mass: 32.04 g/mol

Methanol, also known as methyl alcohol, amongst other names, is an organic chemical and the simplest alcohol, with the formula CH3OH (a methyl group linked to a hydroxyl group, often abbreviated MeOH). 
Methanol is a light, volatile, colourless, flammable liquid with a distinctive alcoholic odour similar to that of ethanol (potable alcohol).

A polar solvent, methanol acquired the name wood alcohol because Methanol was once produced chiefly by the destructive distillation of wood. 
Today, methanol is mainly produced industrially by hydrogenation of carbon monoxide.

Methanol consists of a methyl group linked to a polar hydroxyl group. 
With more than 20 million tons produced annually, Methanol is used as a precursor to other commodity chemicals, including formaldehyde, acetic acid, methyl tert-butyl ether, methyl benzoate, anisole, peroxyacids, as well as a host of more specialised chemicals.

Methanol (CH3OH), also called methyl alcohol, wood alcohol, or wood spirit, the simplest of a long series of organic compounds called alcohols, consisting of a methyl group (CH3) linked with a hydroxy group (OH). 
Methanol was formerly produced by the destructive distillation of wood. 

The modern method of preparing methanol is based on the direct combination of carbon monoxide gas and hydrogen in the presence of a catalyst. 
Increasingly, syngas, a mixture of hydrogen and carbon monoxide derived from biomass, is used for methanol production.

Pure methanol is an important material in chemical synthesis. 
Methanol derivatives are used in great quantities for building up a vast number of compounds, among them many important synthetic dyestuffs, resins, pharmaceuticals, and perfumes. 

Large quantities are converted to dimethylaniline for dyestuffs and to formaldehyde for synthetic resins. 
Methanol is also used in automotive antifreezes, in rocket fuels, and as a general solvent. 

Methanol is also a high-octane, clean-burning fuel that is a potentially important substitute for gasoline in automotive vehicles. 
The methanol derived from wood is used chiefly for rendering industrial ethyl alcohol unfit to drink.

Methanol is a colourless liquid that boils at 64.96 °C (148.93 °F) and solidifies at −93.9 °C (−137 °F). 
Methanol forms explosive mixtures with air and burns with a nonluminous flame. 

Methanol is completely miscible in water. 
Methanol has an odour that is similar to ethyl alcohol, the intoxicant of alcoholic beverages, but is a dangerous poison; many cases of blindness or death have been caused by drinking mixtures containing Methanol.

Methanol is a toxic alcohol that is used industrially as a solvent, pesticide, and alternative fuel source. 
Methanol also occurs naturally in humans, animals, and plants.

Foods such as fresh fruits and vegetables, fruit juices, fermented beverages, and diet soft drinks containing aspartame are the primary sources of methanol in the human body. 
Most methanol poisonings occur as a result of drinking beverages contaminated with methanol or from drinking methanol-containing products. 

In the industrial setting, inhalation of high concentrations of methanol vapor and absorption of methanol through the skin are as effective as the oral route in producing toxic effects. 
The characteristic pungent (alcohol) odor of methanol does not provide sufficient warning of low levels of exposure.

Physical Description of Methanol:
Methanol appears as a colorless fairly volatile liquid with a faintly sweet pungent odor like that of ethyl alcohol. 
Completely mixes with water. 

The vapors are slightly heavier than air and may travel some distance to a source of ignition and flash back. 
Any accumulation of vapors in confined spaces, such as buildings or sewers, may explode if ignited. 
Used to make chemicals, to remove water from automotive and aviation fuels, as a solvent for paints and plastics, and as an ingredient in a wide variety of products.

Occurrence of Methanol:
Small amounts of methanol are present in normal, healthy human individuals. 
One study found a mean of 4.5 ppm in the exhaled breath of test 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 of pectin (0.6 g of methanol.)

Methanol is produced by anaerobic bacteria and phytoplankton.

Interstellar medium:
Methanol is also found in abundant quantities in star-forming regions of space and is used in astronomy as a marker for such regions. 
Methanol is detected through Methanol spectral emission lines.

In 2006, astronomers using the MERLIN array of radio telescopes at Jodrell Bank Observatory discovered a large cloud of methanol in space 463 terametres (288 billion miles) across.
In 2016, astronomers detected methanol in a planet-forming disc around the young star TW Hydrae using ALMA radio telescope.

Applications of Methanol:

Formaldehyde, acetic acid, methyl tert-butylether:
Methanol is primarily converted to formaldehyde, which is widely used in many areas, especially polymers. 

The conversion entails oxidation:
2CH3OH + O2 -> 2CH2O + 2H2O

Acetic acid can be produced from methanol.

Methanol and isobutene are combined to give methyl tert-butyl ether (MTBE). 
MTBE is a major octane booster in gasoline.

Methanol to hydrocarbons, olefins, gasoline:
Condensation of methanol to produce hydrocarbons and even aromatic systems is the basis of several technologies related to gas to liquids. 
These include methanol-to-hydrocarbons (MtH), methanol to gasoline (MtG), methanol to olefins (MtO), and methanol to propylene (MtP). 

These conversions are catalyzed by zeolites as heterogeneous catalysts. 
The MtG process was once commercialized at Motunui in New Zealand.

Gasoline additive:
The European Fuel Quality Directive allows fuel producers to blend up to 3% methanol, with an equal amount of cosolvent, with gasoline sold in Europe. 
China uses more than 4.5 billion liters 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 recent years, however, most modern gasoline-using vehicles can use a variety of alcohol fuels, resulting in similar or higher horsepower, but for a simple change in the vehicle's software settings and possibly a 50 cent seal or tube part.

Other chemicals:
Methanol is the precursor to most simple methylamines, methyl halides, and methyl ethers.
Methyl esters are produced from methanol, including the transesterification of fats and production of biodiesel via transesterification.

Niche and potential uses:

Energy carrier:
Methanol is a promising energy carrier because, as a liquid, Methanol is easier to store than hydrogen and natural gas. 
Methanol energy density is, however, lower than methane, per kg. 
Methanol combustion energy density is 15.6 MJ/L (LHV), whereas that of ethanol is 24 and gasoline is 33 MJ/L.

Further advantages for methanol is Methanol ready biodegradability and low environmental toxicity. 
Methanol does not persist in either aerobic (oxygen-present) or anaerobic (oxygen-absent) environments. 

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, Methanol is unlikely to accumulate in groundwater, surface water, air or soil.

Fuel:
Methanol is occasionally used to fuel internal combustion engines. 

Methanol burns forming carbon dioxide and water:
2CH3OH + 3O2 -> 2CO2 + 4H2O

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

Methanol energy density, however, is less than gasoline, meaning more frequent fill ups would be required. 
However, Methanol is equivalent to super high-octane gasoline in horsepower, and most modern computer-controlled fuel injection systems can already use Methanol.

Methanol is an alternative fuel for ships that helps the shipping industry meet increasingly strict emissions regulations. 
Methanol significantly reduces emissions of sulphur oxides (SOx), nitrogen oxides (NOx) and particulate matter. 
Methanol can be used with high efficiency in marine diesel engines after minor modifications using a small amount of pilot fuel (Dual fuel).

In China, methanol fuels industrial boilers, which are used extensively to generate heat and steam for various industrial applications and residential heating. 
Methanol use is displacing coal, which is under pressure from increasingly stringent environmental regulations.

Direct-methanol fuel cells are unique in their low temperature, atmospheric pressure operation, which lets them be greatly miniaturized.
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.

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.

Other applications of Methanol:
Methanol is used as a 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.
These types of practices are now illegal in the United States, being considered homicide.

Methanol is used as a solvent and as an antifreeze in pipelines and windshield washer fluid. 
Methanol was used as an automobile coolant antifreeze in the early 1900s.
As of May 2018, methanol was banned in the EU for use in windscreen washing or defrosting due to Methanol risk of human consumption as a result of 2012 Czech Republic methanol poisonings.

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.

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

Uses of Methanol:
Methanol is primarily used as an industrial solvent for inks, resins, adhesives, and dyes. 
Methanol is also used as a solvent in the manufacture of cholesterol, streptomycin, vitamins, hormones, and other pharmaceuticals. 

Methanol is also used as an antifreeze for automotive radiators, an ingredient of gasoline (as an antifreezing agent and octane booster), and as fuel for picnic stoves. 
Methanol is also an ingredient in paint and varnish removers. 
Methanol is also used as an alternative motor fuel.

Used as a solvent, alcohol denaturant, antifreeze, and chemical intermediate
Naturally present in blood and urine and in fruits and vegetables
Used in paint removers, windshield-washing solutions, and duplication fluids.

Industrial Processes with risk of exposure:
Semiconductor Manufacturing
Painting (Solvents)
Silk-Screen Printing

Activities with risk of exposure:
Sculpturing plastics
Smoking cigarettes

Both oil base and water base fracturing fluids are being used in the fracturing industry. 
Water base, which includes alcohol-water mixtures and low strength acids, make up the majority of treating fluids. 
The common chemicals added to these fluids are polymers for viscosity development, crosslinkers for viscosity enhancement, pH control chemicals, gel breakers for polymer degradation following the treatment, surfactants, clay stabilizers, alcohol, bactericides, fluid loss additives and friction reducer.

Hydraulic fracturing uses a specially blended liquid which is pumped into a well under extreme pressure causing cracks in rock formations underground. 
These cracks in the rock then allow oil and natural gas to flow, increasing resource production.

Chemical Name: Methanol

Chemical Purpose: Product stabilizer and/or winterizing agent

Product Function: Corrosion inhibitor.

In 2013, the breakdown of total methanol use was formaldehyde, 31% MTBE, 11% acetic acid, 10% and all other includes chloromethane, methyl methacrylate, methylamine, dimethyl terephthalate, solvents, glycol methyl ethers, antifreeze in windshield wipers, and drilling muds and fuels.

Dehydrator of natural gas; fuel for utility plants (methyl fuel); feedstock for manufacture of synthetic proteins by continuous fermentation; source of hydrogen for fuel cells, home-heating-oil extender.

Substance listed with specific concentration in tattoo ink and/or permanent make up according to EU Commission Regulation 2020/2081. 
The concentration limit (by weight) is 11%.

Methanol is a toxic alcohol that is used industrially as a solvent, pesticide, and alternative fuel source. 
Methanol also occurs naturally in humans, animals, and plants. 

Foods such as fresh fruits and vegetables, fruit juices, fermented beverages, and diet soft drinks containing aspartame are the primary sources of methanol in the human body. 
Most methanol poisonings occur as a result of drinking beverages contaminated with methanol or from drinking methanol-containing products. 

In the industrial setting, inhalation of high concentrations of methanol vapor and absorption of methanol through the skin are as effective as the oral route in producing toxic effects. 
The characteristic pungent (alcohol) odor of methanol does not provide sufficient warning of low levels of exposure.

Industry Uses of Methanol:
Adhesives and sealant chemicals
Antifreeze/pipeline dehydration
Corrosion inhibitors and anti-scaling agents
Fluid fill - windshield washer fluid
Fuels and fuel additives
Functional fluids (closed systems)
Functional fluids (open systems)
Industrial waste treatment agent
Intermediates
Laboratory chemicals
Odor agents
Oxidizing/reducing agents
Paint additives and coating additives not described by other categories
Plasticizers
Process regulators
Processing aids, not otherwise listed
Processing aids, specific to petroleum production
Solids separation agents
Solvents (for cleaning and degreasing)
Solvents (which become part of product formulation or mixture)
Surface active agents
Thermal paper coating
Viscosity adjustors

Consumer Uses of Methanol:
Adhesives and sealants
Agricultural products (non-pesticidal)
Air care products
Anti-freeze and de-icing products
Automotive Windshield Washer Fluid enclosed in assembled, imported vehicles
Automotive care products
Biodiesel production.
Building/construction materials - wood and engineered wood products
Electrical and electronic products
Fabric, textile, and leather products not covered elsewhere
Feedstock
Foam seating and bedding products
Fuels and related products
Internal Feedstock
Laundry and dishwashing products
Metal products not covered elsewhere
Paints and coatings
Paper products
Personal care products
Plastic and rubber products not covered elsewhere
Solvent
Water treatment products

Methods of Manufacturing of Methanol:
Methanol is currently produced on an industrial scale exclusively by catalytic conversion of synthesis gas according to the principles of the low-pressure (LP) methanol process (5-10 MPa). 
The main advantages of the low-pressure processes are lower investment and production costs, improved operational reliability, and greater flexibility in the choice of plant size.

All commercial methanol processes employ a synthesis loop.
This configuration overcomes equilibrium conversion limitations at typical catalyst operating conditions.

A recycle system that gives high overall conversions is feasible because product methanol and water can be removed from the loop by condensation. 
The makeup synthesis gas is compressed, mixed with recycled gas, and preheated against the converter effluent gas before entering the converter. 

The converter effluent is first used to heat the saturator water or boiler feedwater before being returned to the loop interchanger and then on to a cooler, which condenses the crude methanol-water mixture. 
Noncondensable gases are disengaged in a catchpot for recycle. 

A purge is taken from this recycle to remove excess hydrogen, methane, and other inerts. 
The crude methanol mixture is sent forward to the distillation section for the final purification.

By high-pressure catalytic synthesis from carbon monoxide and hydrogen; partial oxidation of natural gas hydrocarbons; several processes for making methanol by gasification of wood, peat, and lignite have been developed but have not yet proved out commercially; from methane with molybdenum catalyst (experimental).

General Manufacturing Information of Methanol:

Industry Processing Sectors:
Adhesive manufacturing
All other basic organic chemical manufacturing
All other chemical product and preparation manufacturing
All other petroleum and coal products manufacturing
Chemical used in medical diagnostic/pathology profession
Electrical equipment, appliance, and component manufacturing
Mining (except oil and gas) and support activities
Miscellaneous manufacturing
Nonmetallic mineral product manufacturing (includes clay, glass, cement, concrete, lime, gypsum, and other nonmetallic mineral product manufacturing.
Oil and gas drilling, extraction, and support activities
Paint and coating manufacturing
Paper manufacturing
Pesticide, fertilizer, and other agricultural chemical manufacturing
Petrochemical manufacturing
Petroleum refineries
Pharmaceutical and medicine manufacturing
Photographic film paper, plate, and chemical manufacturing
Plastic material and resin manufacturing
Services
Soap, cleaning compound, and toilet preparation manufacturing
Synthetic rubber manufacturing
Transportation equipment manufacturing
Utilities
Wholesale and retail trade
Wood product manufacturing

Originally called wood alcohol, since Methanol was obtained from the destructive distillation of wood, today commercial methanol is sometimes referred to as synthetic methanol because Methanol is produced from synthesis gas, a mixture of hydrogen and carbon oxides, generated by a variety of sources

Production of Methanol:

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
CO + 2H2 -> CH3OH
is characterized by high selectivity (>99.8%). 

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 Methanol, too, reacts to form methanol according to the equation
CO2 + 3H2 -> CH3OH + H2O

In terms of mechanism, the process occurs via initial conversion of CO into CO2, which is then hydrogenated:
CO2 + 3H2 -> CH3OH + H2O
where the H2O byproduct is recycled via the water-gas shift reaction
CO + H2O -> CO2 + H2
This gives an overall reaction
CO + 2 H2 -> CH3OH
which is the same as listed above. 

In a process closely related to methanol production from synthesis gas, a feed of hydrogen and CO2 can be used directly.
The main advantage of this process is that captured CO2 and hydrogen sourced from electrolysis could be used, removing the dependence on fossil fuels.

Biosynthesis of Methanol:
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 and NAD+:
CH4 + O2 + NADPH + H^+ -> CH3OH + H2O + NAD^+

Both Fe- and Cu-dependent enzymes have been characterized.
Intense but largely fruitless 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. 
Some strategies exist to circumvent this problem. 

Examples include Shilov systems and Fe- and Cu containing zeolites.
These systems do not necessarily mimic the mechanisms employed by metalloenzymes, but draw some inspiration from them. 

Active sites can vary substantially from those known in the enzymes. 
For example, a dinuclear active site is proposed in the sMMO enzyme, whereas a mononuclear iron (alpha-oxygen) is proposed in the Fe-zeolite.

Sampling Procedures of Methanol:
Two sampling methods for reliable determination of methanol concentration were studied. 
Methanol vapor stored in glass container was found to be decomposed on the glass surface. 

The decomposition increased as the surface area of the glass container was extended. 
The proportion of the decomposition in the glass container was relatively high, especially when the concentration of methanol vapor was low. 

Therefore, a reliable determination by the above sampling method was impossible. 
In the solid sorbent sampling by silica gel, the collected methanol was also decomposed, but the decomposed amount was negligibly small compared to the collected methanol when the amount of methanol was more than 0.1 microliter of the liquid methanol. 
Methanol could be concluded from the foregoing findings that the determination of methanol concentration by this method is reliable.

Quality specifications and analysis:
Methanol is available commercially in various purity grades. 
Commercial methanol is generally classified according to ASTM purity grades A and AA. 

Both grade A and grade AA purity are 99.85% methanol by weight. 
Grade "AA" methanol contains trace amounts of ethanol as well.

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). 

UV-vis spectroscopy is a convenient method for detecting aromatic impurities. 
Water content can be determined by the Karl-Fischer titration.

Absorption, Distribution and Excretion:
Methanol is absorbed following inhalation or ingestion, and inhalation is the major route of absorption in the occupational environment. 
There is no agreement on the potential risk of dermal exposure to methanol. 
Methanol is uniformly distributed according to the relative water content of the tissue.

Methyl alcohol is readily absorbed from GI and respiratory tracts.

The rate of absorption of methanol from the gastrointestinal tract is approximately 8.4 mg/sq cm/hr. 
Time to peak serum concentration after ingestion is 30-60 minutes for methanol.

Under experimental conditions in man following ingestion and inhalation, dosages of 71-84 mg/kg orally resulted in blood levels of 4.7-7.6 mg/100 mL 2-3 hr afterward. 
Urine/blood concentration ratio was constant at about 1.3.
Inhalation of 500-1000 ppm for 3-4 hr gave urine concentration of about 1-3 mg/100 mL.

Clinical Laboratory Methods of Methanol:
A new method for rapid, direct determination of formate in blood serum samples by capillary electrophoresis with contactless conductometric detection is presented. 
A selective separation of formate was achieved in approximately 1 min using an electrolyte system comprising 10 mM L-histidine, 15 mM glutamic acid and 30 uM cetyltrimethylammonium bromide at pH 4.56. 

The only sample preparation was dilution (1:100) with deionized water. 
The limit of detection and limit of quantitation was 2.2 uM and 7.3 uM, respectively, which corresponds to 0.22 mM and 0.73 mM in undiluted blood serum. 

The method provides a simple and rapid diagnostic test in suspected methanol intoxication cases. 
The method has been successfully tested on determination of formate in blood of a patient admitted to the hospital under acute methanol intoxication. 

The peak concentration of formate detected in the patient blood serum was 12.4 mM, which is 10- to 100-fold higher than the normal values in healthy population. 
The developed method presents the fastest test currently available to detect formate in blood samples.

Ultramicro chromatographic method, incl methanol, in blood and urine.

Determination in blood serum of methanol was accomplished by gas chromatography using a Varian Model 2100 gas chromatograph equipped with dual columns, dual flame ionization detectors, and a linear temp programmer. 
Standard curves were linear over the concn range 1-100 nmol/mL and the limits of detection were 0.1 nmol/mL ethylene glycol. 
No interference from 30 solvents studied was detected.

A sampling strategy was developed to detect personal exposure to methanol and formic acid vapors. 
Formic acid is the metabolic end product of methanol, and part of inhaled formic acid is excreted directly in urine, so that urinary formic acid would reveal exposure to both agents. 

A linear relationship to inhaled vapors, however, could be shown only if urinary sampling were delayed until 16 hr (next morning) after exposure. 
Exposure to methanol vapor at the current Finnish hygienic limit level (200 ppm) produced 80 mg formic acid/g creatinine; exposure to formic acid at the hygienic limit (5 ppm) caused 90 mg/g creatinine. 
The similarity of these figures may indicate a common toxicological foundation of these empirically set values.

Headspace gas chromatography was used to determine the concentration of ethanol and methanol in blood samples from 519 individuals suspected of drinking and driving in Sweden where the legal alcohol limit is 0.50 mg/g in whole blood (11 mmol/L). 
The concentration of ethanol in blood ranged from 0.01 to 3.52 mg/g with a mean of 1.83 + or - 0.82 mg/g (+ or - standard deviation). 

The frequency distribution was symmetrical about the mean but deviated from normality. 
A plot of the same data on normal probability paper indicated that Methanol might be composed of two subpopulations (bimodal). 

The concentration of methanol in the same blood specimens ranged from 1 to 23 mg/L with a mean of 7.3 + or - 3.6 mg/L (+ or - standard deviation) and this distribution was markedly skew (+). 
The concentration of ethanol (x) and methanol (y) were positively correlated (r= 0.47, P<0.001) and implies that 22% (r2) of the variance in blood-methanol can be attributed to Methanol linear regression on blood-ethanol. 

The regression equation was y= 3.6 + 2.1 x and the standard error estimate was 0.32 mg/L. 
This large scatter precludes making reliable estimates of blood-methanol concentration from measurements of blood-ethanol concentration and the regression equation. 

But higher blood-methanol concentrations are definitely associated with higher blood-ethanol in this sample of Swedish drinking drivers. 
Frequent exposure to methanol and Methanol toxic products of metabolism, formaldehyde and formic acid, might constitute an additional health risk associated with heavy drinking in predisposed individuals. 
The determination of methanol in blood of drinking drivers in addition to ethanol could indicate long-standing ethanol intoxication and therfore potential problem drinkers or alcoholics.

Metabolism/Metabolites of Methanol:
We recently showed that methanol emitted by wounded plants might function as a signaling molecule for plant-to-plant and plant-to-animal communications. 
In mammals, methanol is considered a poison because the enzyme alcohol dehydrogenase (ADH) converts methanol into formaldehyde and other products. 

However, the detection of methanol in the blood and exhaled air of healthy volunteers suggests that methanol may be a chemical with specific functions rather than a metabolic waste product. 
Using a genome-wide analysis of the mouse brain, we demonstrated that an increase in blood methanol concentration led to a change in the accumulation of mRNAs from genes primarily involved in detoxification processes and regulation of the alcohol/aldehyde dehydrogenases gene cluster. 

To test the role of ADH in the maintenance of low methanol concentration in the plasma, we used the specific ADH inhibitor 4-methylpyrazole (4-MP) and showed that intraperitoneal administration of 4-MP resulted in a significant increase in the plasma methanol, ethanol and formaldehyde concentrations. 
Removal of the intestine significantly decreased the rate of methanol addition to the plasma and suggested that the gut flora may be involved in the endogenous production of methanol. 

ADH in the liver was identified as the main enzyme for metabolizing methanol because an increase in the methanol and ethanol contents in the liver homogenate was observed after 4-MP administration into the portal vein. 
Liver mRNA quantification showed changes in the accumulation of mRNAs from genes involved in cell signaling and detoxification processes. 
We hypothesized that endogenous methanol acts as a regulator of homeostasis by controlling the mRNA synthesis.

Many studies have reported that methanol toxicity to primates is mainly associated with Methanol metabolites, formaldehyde (FA) and formic acid. 
While methanol metabolism and toxicology have been best studied in peripheral organs, little study has focused on the brain and no study has reported experimental evidence that demonstrates transformation of methanol into FA in the primate brain. 

In this study, three rhesus macaques were given a single intracerebroventricular injection of methanol to investigate whether a metabolic process of methanol to FA occurs in nonhuman primate brain. 
Levels of FA in cerebrospinal fluid (CSF) were then assessed at different time points. 

A significant increase of FA levels was found at the 18th hour following a methanol injection. 
Moreover, the FA level returned to a normal physiological level at the 30th hour after the injection. 

These findings provide direct evidence that methanol is oxidized to FA in nonhuman primate brain and that a portion of the FA generated is released out of the brain cells. 
This study suggests that FA is produced from methanol metabolic processes in the nonhuman primate brain and that FA may play a significant role in methanol neurotoxicology.

Methanol is among the most common short-chain alcohols in fermenting fruits, the natural food and oviposition sites of the fruit fly Drosophila melanogaster. 
Our previous results showed that cytochrome P450 monooxygenases (CYPs) were associated with methanol detoxification in the larvae. 

Catalases, alcohol dehydrogenases (ADHs), esterases (ESTs) and glutathione S-transferases (GSTs) were specifically inhibited by 3-amino-1,2,4-triazole (3-AT), 4-methylpyrazole (4-MP), triphenyl phosphate (TPP) and diethylmeleate (DEM), respectively. 
CYPs were inhibited by piperonyl butoxide (PBO) and 1-aminobenzotriazole (1-ABT). 

In the present paper, the involvements of these enzymes in methanol metabolism were investigated in female and male adults by determining the combination indices of methanol and their corresponding inhibitors. 
When PBO, 1-ABT, 3-AT, 4-MP and TPP were individually mixed with methanol, they exhibited significant synergism to the mortality of the adults after 72 hr of dietary exposure. 

In contrast, the DEM and methanol mixture showed additive effects. 
Moreover, methanol exposure dramatically increased CYP activity and up-regulated mRNA expression levels of several Cyp genes. 

Bioassays using different strains revealed that the variation in ADH activity and RNAi-mediated knockdown of alpha-Est7 significantly changed LC50 values for methanol. 
These results suggest that CYPs, catalases, ADHs and ESTs are partially responsible for methanol elimination in adults. 
Methanol seems that there are some differences in methanol metabolism between larvae and adults, but not between female and male adults.

Metabolism of methanol occurs in a three-step process initially involving oxidation to formaldehyde by hepatic alcohol dehydrogenase, which is a saturable rate-limiting process. 
In the second step, formaldehyde is oxidized by aldehyde dehydrogenase to formic acid or formate depending on the pH. 

In the third step, formic acid is detoxified by a folate-dependent pathway to carbon dioxide. 
Elimination of methanol from the blood appears to be slow in all species, especially when compared to ethanol. 
In humans, urinary methanol concentrations have been found to be proportional to the concentration of methanol in blood.

Biological Half-Life of Methanol:
The mean plasma half-life of methanol during fomepizole treatment was 52 hr (range 22-87); the higher the serum methanol, the longer the half-life.

Biological half-life of methanol elimination in expired air is 1.5 hr after either oral or dermal application.

Experiments were made during the morning after human volunteers had consumed 1000-1500 mL red wine (9.5% weight/volume ethanol, 100 mg/L methanol) the previous evening. 
The washout of methanol from the body coincided with the onset of hangover. 

The concentrations of ethanol and methanol in blood were determined indirectly by analysis of end-expired alveolar air. 
In the morning when blood-ethanol dropped below the Km of liver alcohol dehydrogenase of about 100 mg/L (2.2 mM), the disappearance half-life of ethanol was 21, 22, 18 and 15 min in 4 test subjects, respectively. 
The corresponding elimination half-lives of methanol were 213, 110, 133 and 142 min in these same individuals.

Urinary methanol levels decreased exponentially with a half-life of about 2.5 to 3 hr in four volunteers exposed by inhalation to 102, 205, or 300 mg/cu m for 8 hr.

History of Methanol:
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 Methanol via the distillation of buxus (boxwood).

Methanol later became known as "pyroxylic spirit". 
In 1834, the French chemists Jean-Baptiste Dumas and Eugene Peligot determined Methanol elemental composition.

They also introduced the word "methylène" to organic chemistry, forming Methanol from Greek methy = "alcoholic liquid" + hȳlē = "forest, wood, timber, material". 
"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, which, in organic chemistry, forms names of carbon groups, is from the word methyl.

French chemist Paul Sabatier presented the first process that could be used to produce methanol synthetically in 1905. 
This process suggested that carbon dioxide and hydrogen could be reacted to produce methanol.

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 and received a patent. 
According to Bozzano and Manenti, BASF's process was first utilized in Leuna, Germany in 1923. 
Operating conditions consisted of "high" temperatures (between 300 and 400 °C) and pressures (between 250 and 350 atm) with a zinc/chromium oxide catalyst.

US patent 1,569,775 (US 1569775) was applied for on 4 Sep 1924 and issued on 12 January 1926 to BASF; 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) process was developed by ICI in the late 1960s US 3326956 with the technology patent since long expired.

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.

The use of methanol as a motor fuel received attention during the oil crises of the 1970s. 
By the mid-1990s, over 20,000 methanol "flexible fuel vehicles" (FFV) 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 interest in methanol fuels.

In the early 1970s, a process was developed by Mobil for producing gasoline fuel from methanol.

Between the 1960s and 1980s methanol emerged as a precursor to the feedstock chemicals acetic acid and acetic anhydride. 
These processes include the Monsanto acetic acid synthesis, Cativa process, and Tennessee Eastman acetic anhydride process.

Handling and Storage of Methanol:

Nonfire Spill Response:
Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. 
ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). 

All equipment used when handling the product must be grounded. 
Do not touch or walk through spilled material. 

Stop leak if you can do Methanol without risk. 
Prevent entry into waterways, sewers, basements or confined areas. 
A vapor-suppressing foam may be used to reduce vapors. 

SMALL SPILL: Absorb with earth, sand or other non-combustible material and transfer to containers for later disposal. 
Use clean, non-sparking tools to collect absorbed material. 

LARGE SPILL: Dike far ahead of liquid spill for later disposal. 
Water spray may reduce vapor, but may not prevent ignition in closed spaces.

Safe Storage of Methanol:
Separated from incompatible materials. 
Cool. 

Fireproof. 
Keep in a well-ventilated room.

Storage Conditions of Methanol:
Keep container tightly closed in a dry and well-ventilated place. 
Containers which are opened must be carefully resealed and kept upright to prevent leakage.

When large amounts of methanol are stored in enclosed 14 Methanol spaces, monitoring by means of lower explosion limit monitors is desirable.

Permanently installed fire-extinguishing equipment should be provided in large storage facilities. 
Water cannons are generally installed in storage tank farms to cool steel constructions and neighboring tanks in the event of fire. 
Large tanks should have permanently installed piping systems for alcohol-resistant fire-extinguishing foams.

Small-Scale Storage. 
Small amounts (</= 10 L) of methanol for laboratory and industrial use are stored in glass bottles or sheet-metal cans; amounts up to 200 L are stored and transported in steel drums. 

Some plastic bottles and containers cannot be used because of their permeability and the danger of dissolution of plasticizers. 
High-density polyethylene and polypropylene are suitable, whereas poly(vinyl chloride) and polyamides are unsuitable.

Safety of Methanol:
Methanol is highly flammable. 
Methanol vapours are slightly heavier than air, can travel and ignite. 
Methanol fires should be extinguished with dry chemical, carbon dioxide, water spray or alcohol-resistant foam.

First Aid of Methanol:
EYES: First check the victim for contact lenses and remove if present. 
Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. 

Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. 
IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. 

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. 
Gently wash all affected skin areas thoroughly with soap and water. 
If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. 

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. 
If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 

Provide proper respiratory protection to rescuers entering an unknown atmosphere. 
Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. 

INGESTION: DO NOT INDUCE VOMITING. 
Volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. 
If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. 

IMMEDIATELY transport the victim to a hospital. 
If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. 

DO NOT INDUCE VOMITING. 
IMMEDIATELY transport the victim to a hospital.

Fire Fighting of Methanol:
CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. 

SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam. 

LARGE FIRE: Water spray, fog or alcohol-resistant foam. 
Move containers from fire area if you can do Methanol without risk. 
Dike fire-control water for later disposal; do not scatter the material. 

Use water spray or fog; do not use straight streams. 
FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. 

Cool containers with flooding quantities of water until well after fire is out. 
Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. 

ALWAYS stay away from tanks engulfed in fire. 
For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn.

Fire Fighting Procedures of Methanol:

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. 
Use water in flooding quantities as fog. 
Solid streams of water may be ineffective. 

Cool all containers with flooding quantities or water. 
Apply water from as far a distance as possible. 
Use "alcohol" foam, dry chemical or carbon dioxide.

Isolation and Evacuation of Methanol:
As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions.

SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. 

FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.

Spillage Disposal of Methanol:
Evacuate danger area! Consult an expert! Remove all ignition sources.      
Ventilation. 

Personal protection: complete protective clothing including self-contained breathing apparatus. 
Do NOT wash away into sewer. 
Collect leaking and spilled liquid in covered containers as far as possible. 

Absorb remaining liquid in sand or inert absorbent. 
Wash away remainder with plenty of water. 
Store and dispose of according to local regulations.

Cleanup Methods of Methanol:
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. 
Avoid breathing vapors, mist or gas. 

Ensure adequate ventilation. 
Remove all sources of ignition. 

Evacuate personnel to safe areas. 
Beware of vapors accumulating to form explosive concentrations. 
Vapors can accumulate in low areas. 

Environmental precautions: Prevent further leakage or spillage if safe to do so. 
Do not let product enter drains. 
Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations.

General Spill Actions: Stop or reduce discharge of material if this can be done without risk. 
Eliminate all sources of ignition.

Avoid skin contact and inhalation. 
A fluorocarbon water foam can be applied to the spill to diminish vapor and fire hazard. 

Hycar and carbopol, which are absorbent materials, have shown possible applicability for vapor suppression and/or containment of methanol in spill situations. 
Leaking containers should be removed to the outdoors or to an isolated, well-ventilated area and the contents transferred to other suitable containers. 

The following materials are recommended for plugging leaks of methanol: polyester (eg Glad bag), imid polyester (eg brown-in-bag), stafoam urethane foam, sea-going epoxy putty, and MSA urethane.

Spills on Land: Contain if possible by forming mechanical or chemical barriers to prevent spreading. 
Absorb on sand, vermiculite or other absorbent and shovel into metal containers for disposal. 

Application of universal gelling agent to immobilize the spill, or the use of fly ash or cement powder to absorb the liquid bulk should also be considered. 
Other recommended sorbent materials are activated carbon and a universal sorbent material.

Spills in Water: After containment, a universal gelling agent can be injected to solidify trapped mass to increase the effectiveness of berms. 
Activated carbon can be applied at 10% the spilled amount over region occupied by 10 mg/L or greater concentrations. 
Then use mechanical dredges or lifts to remove immobilized masses of pollutants.

Disposal Methods of Methanol:
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U154 and F003, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. 
Concentrations shall be lower than applicable environmental discharge or disposal criteria. 

Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. 
Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. 
If Methanol is not practicable to manage the chemical in this fashion, Methanol must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. 
Offer surplus and non-recyclable solutions to a licensed disposal company. 

Contact a licensed professional waste disposal service to dispose of this material. 
Contaminated packaging: Dispose of as unused product.

Disposal: Waste methanol must never be discharged directly into sewers or surface waters. 
Large quantities of waste methanol can either be disposed of at licensed waste solvent disposal company or reclaimed by filtration and distillation. 
Methanol can also be incinerated.

Preventive Measures of Methanol:
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. 
Avoid breathing vapors, mist or gas. 

Ensure adequate ventilation. 
Remove all sources of ignition. 

Evacuate personnel to safe areas. 
Beware of vapors accumulating to form explosive concentrations. 
Vapors can accumulate in low areas. 

Environmental precautions: Prevent further leakage or spillage if safe to do so. 
Do not let product enter drains.

Precautions for safe handling: Avoid contact with skin and eyes. 
Avoid inhalation of vapor or mist. 
Use explosion-proof equipment. 

Keep away from sources of ignition - No smoking. 
Take measures to prevent the build up of electrostatic charge.

Appropriate engineering controls: Avoid contact with skin, eyes and clothing. 
Wash hands before breaks and immediately after handling the product.

Gloves must be inspected prior to use. 
Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. 
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. 
Wash and dry hands.

Information of Methanol:
CAS number: 67-56-1
EC index number: 603-001-00-X
EC number: 200-659-6
Hill Formula: CH₄O
Chemical formula: CH₃OH
Molar Mass: 32.04 g/mol
HS Code: 2905 11 00
Quality Level: MQ300

Identifiers of Methanol:
CAS Number: 67-56-1
3DMet: B01170
Beilstein Reference: 1098229
ChEBI: CHEBI:17790
ChEMBL: ChEMBL14688
ChemSpider: 864
ECHA InfoCard: 100.000.599
EC Number: 200-659-6
Gmelin Reference: 449
KEGG: D02309
MeSH: Methanol
PubChem CID: 887
RTECS number: PC1400000
UNII: Y4S76JWI15
UN number: 1230
CompTox Dashboard (EPA): DTXSID2021731
InChI: InChI=1S/CH4O/c1-2/h2H,1H3
Key: OKKJLVBELUTLKV-UHFFFAOYSA-N
InChI=1/CH4O/c1-2/h2H,1H3
Key: OKKJLVBELUTLKV-UHFFFAOYAX
SMILES: CO

Properties of Methanol:
Chemical formula: CH3OH or CH4O
Molar mass: 32.04 g mol−1
Appearance: Colourless liquid
Odor: Sweet and pungent
Density: 0.792 g/cm3
Melting point: −97.6 °C (−143.7 °F; 175.6 K)
Boiling point: 64.7 °C (148.5 °F; 337.8 K)
Solubility in water: miscible
log P: −0.69
Vapor pressure: 13.02 kPa (at 20 °C)
Acidity (pKa): 15.5
Conjugate acid: Methyloxonium
Conjugate base: Methanolate
Magnetic susceptibility (χ): −21.40·10−6 cm3/mol
Refractive index (nD): 1.33141
Viscosity: 0.545 mPa·s (at 25 °C)
Dipole moment: 1.69 D

Molecular Weight: 32.042
XLogP3-AA: -0.5
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 32.026214747
Monoisotopic Mass: 32.026214747
Topological Polar Surface Area: 20.2 Ų
Heavy Atom Count: 2
Complexity: 2
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Methanol:
Purity (GC): ≥ 99.9 %
Identity (IR): conforms
Color: ≤ 10 Hazen
Acidity: ≤ 0.0005 meq/g
Alkalinity: ≤ 0.0002 meq/g
Acetone (GC): ≤ 0.05 %
Ethanol (GC): ≤ 0.1 %
Evaporation residue: ≤ 10 mg/l
Water: ≤ 0.003 %

Thermochemistry of Methanol:
Heat of combustion, higher value (HHV): 725.7 kJ/mol, 173.4 kcal/mol, 5.77 kcal/g

Related compounds of Methanol:
Methanethiol
Silanol
Ethanol

Names of Methanol:

Preferred IUPAC name of Methanol:
Methanol

Other names of Methanol:
Carbinol
Columbian spirits
Hydroxymethane
MeOH
Methyl alcohol
Methyl hydroxide
Methylic alcohol
Methylol
Methylene hydrate, primary alcohol
Pyroligneous spirit
Wood alcohol
Wood naphtha
Wood spirit

Synonyms of Methanol:    
MeOH
Hydroxymethane
Methyl alcohol
Carbino
methanol
methyl alcohol
67-56-1
wood alcohol
carbinol
Wood spirit
Wood naphtha
Methylol
Methyl hydroxide
Pyroxylic spirit
Colonial Spirit
Columbian Spirit
Monohydroxymethane
Methylalkohol
Columbian spirits
Alcool methylique
MeOH
Methyl hydrate
Alcohol, methyl
CH3OH
Metanolo
Alcool metilico
Bieleski's solution
Colonial spirits
Metylowy alkohol
Pyroxylic spirits
Hydroxymethane
Freers Elm Arrester
Surflo-B17
Rcra waste number U154
Wilbur-Ellis Smut-Guard
Metanol
Metanolo
Coat-B1400
Eureka Products, Criosine
Metanol
Caswell No. 552
Methylalkohol
Spirit of wood
Alcool metilico
Metylowy alkohol
Alcool methylique
X-Cide 402 Industrial Bactericide
HSDB 93
Ideal Concentrated Wood Preservative
Methyl alcohol
Eureka Products Criosine Disinfectant
NSC 85232
UN1230
CCRIS 2301
Pyro alcohol
CH4O
AI3-00409
MetOH
RCRA waste no. U154
UNII-Y4S76JWI15
EPA Pesticide Chemical Code 053801
Methanol-water mixture
CHEBI:17790
Y4S76JWI15
Methanol, anhydrous
MFCD00004595
NSC-85232
Methyl alcohol (NF)
NCGC00091172-01
Aqualine&trade; Solvent
Methanol-[17O]
DSSTox_CID_1731
Aqualine&trade; Titrant 5
DSSTox_RID_76297
DSSTox_GSID_21731
Methanol, for HPLC, >=99.9%
Methanol, ACS reagent, >=99.8%
Methanol, or methyl alcohol
CAS-67-56-1
170082-17-4
MOH
EINECS 200-659-6
Methylalcohol
methly alcohol
Primary alcohol
Alcohol,methyl
methanol-
Wood
primary alcohols
Methanol cluster
Methanol NF
Nat. Methanol
a primary alcohol
Methanol LC-MS
Methanol, for HPLC
Methanol (Recovered)
Methanol, ACS Grade
Solutions, Bieleski's
Methanol, HPLC grade
Methanol, LCMS grade
Columbian spirits
Hydroxymethylidyne radical
3'-Hydroxystanozolol-D3
Methanol (Peptide Grade)
Methanol, Histology Grade
bmse000294
Epitope ID:116865
EC 200-659-6
Aqualine&trade; Solvent CM
Methanol Reagent Grade ACS
Methanol, or methyl alcohol
Methanol, LR, >=99%
Methanol, SAJ special grade
Methanol, analytical standard
WLN: Q1
Methanol HPLC Gradient Grade
Methanol, Environmental Grade
Aqualine&trade; Electrolyte A
CHEMBL14688
Methanol, anhydrous, 99.8%
Methanol, p.a., 99.8%
Methanol, p.a., 99.9%
Aqualine&trade; Electrolyte AG
Aqualine&trade; Electrolyte CG
DTXSID2021731
Methanol, AR, >=99.5%
CHEBI:15734
Methanol, NMR reference standard
Methanol, ultrapure, HPLC Grade
Methanol, 99.8%, ACS reagent
Methanol, anhydrous, >=99.5%
Methanol, low water for titration
Methanol GC, for residue analysis
Eriochrome&trade; Black T Solution
Methanol, Absolute - Acetone free
Methanol, HPLC gradient, 99.9%
Methanol, or methyl alcohol
NSC85232
Methanol, for HPLC, >=99.8%
Methanol, PRA grade, >=99.9%
Tox21_111094
Tox21_202523
8292AF
Methanol, HPLC Plus, >=99.9%
AKOS000269045
Methanol, purification grade, 99.8%
MCULE-1370061678
UN 1230
Methanol, UHPLC, for mass spectrometry
Methanol solution, technical grade, 95%
Methanol, >=99.8%, for chromatography
Methanol, SAJ first grade, >=99.5%
NCGC00260072-01
Methanol, JIS special grade, >=99.8%
Methanol, Laboratory Reagent, >=99.6%
Methanol, UV HPLC spectroscopic, 99.9%
Methanol, anhydrous, ZerO2(TM), 99.8%
Methanol, spectrophotometric grade, >=99%
FT-0623465
FT-0628297
FT-0628299
FT-0700908
FT-0700959
M0097
M0628
Methanol, ultrapure, Spectrophotometric Grade
C00132
D02309
Methanol, for HPLC, gradient grade, 99.93%
Methanol, suitable for determination of dioxins
Q14982
Methanol, for HPLC, gradient grade, >=99.9%
Methanol, glass distilled HRGC/HPLC trace grade
Methanol, low benzene, ACS reagent, >=99.8%
Methanol, ACS spectrophotometric grade, >=99.9%
Methanol HPLC, UV-IR min. 99.9% isocratic grade
Methanol, BioReagent, suitable for protein sequencing
Methanol, for HPLC, gradient grade, >=99.8% (GC)
Methanol, HPLC Plus, >=99.9%, poly-coated bottles
Q27115113
Methanol solution, (Methanol:Acetonitrile 1:1 (v/v))
Methanol solution, contains 0.50 % (v/v) triethylamine
Methanol, Vetec(TM) reagent grade, anhydrous, >=99.8%
Methanol solution, (Methanol:Dichloromethane 1:1 (v/v))
Methanol, for residue analysis, suitable for 5000 per JIS
Moisture in methanol, 325 mg/kg, NIST(R) SRM(R) 8510
Moisture in methanol, 93 mg/kg, NIST(R) SRM(R) 8509
UNII-N4G9GAT76C component OKKJLVBELUTLKV-UHFFFAOYSA-N
Methanol solution, (Methanol:Dimethyl sulfoxide 1:1 (v/v))
Methanol solution, contains 0.1 % (v/v) trifluoroacetic acid
Methanol solution, for protein sequence analysis, ~50% in H2O
Methanol with 0.1% trifluoroacetic acid, tested for UHPLC-MS
Methanol, >=99.8%, suitable for absorption spectrum analysis
Methanol, semiconductor grade PURANAL(TM) (Honeywell 17824)
Methanol, p.a., ACS reagent, reag. ISO, reag. Ph. Eur., 99.9%
Methanol, puriss. p.a., absolute, ACS reagent, >=99.8% (GC)
Methanol, semiconductor grade VLSI PURANAL(TM) (Honeywell 17744)
Methanol, suitable for protein sequencing, BioReagent, >=99.93%
Methyl alcohol, United States Pharmacopeia (USP) Reference Standard
Methanol, Pharmaceutical Secondary Standard; Certified Reference Material
Methanol, puriss., meets analytical specification of Ph Eur, >=99.7% (GC)
Methanol, suitable for 1000 per JIS, >=99.8%, for residue analysis
Methanol, suitable for 300 per JIS, >=99.8%, for residue analysis
(5beta,17beta)-17-Hydroxy-17-(methyl-d3)-2'H-androst-2-eno[3,2-c]pyrazol-5'(1'H)-one
Methanol solution, contains 0.1 % (v/v) trifluoroacetic acid, 5 % (v/v) water, for HPLC
Methanol solution, contains 0.10 % (v/v) trifluoroacetic acid, 10 % (v/v) water
Methanol solution, for HPLC, contains 10 % (v/v) water, 0.1 % (v/v) trifluoroacetic acid
Methanol, for HPLC, gradient grade, suitable as ACS-grade LC reagent, >=99.9%
Methanol, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., >=99.8% (GC)
Residual Solvent Class 2 - Methanol, United States Pharmacopeia (USP) Reference Standard
JandaJel(TM)-OH, 100-200 mesh, extent of labeling: 1.0 mmol/g OH loading, 2 % cross-linked
JandaJel(TM)-OH, 200-400 mesh, extent of labeling: 1.0 mmol/g OH loading, 2 % cross-linked
JandaJel(TM)-OH, 50-100 mesh, extent of labeling: 1.0 mmol/g OH loading, 2 % cross-linked
Methanol solution, contains 0.10 % (v/v) formic acid, UHPLC, for mass spectrometry, >=99.5%
Methanol solution, NMR reference standard, 4% in methanol-d4 (99.8 atom % D), NMR tube size 3 mm x 8 in.
Methanol solution, NMR reference standard, 4% in methanol-d4 (99.8 atom % D), NMR tube size 5 mm x 8 in.

MeSH of Methanol:
Alcohol, Methyl
Alcohol, Wood
Carbinol
Methanol
Methoxide, Sodium
Methyl Alcohol
Sodium Methoxide
Wood Alcohol