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Home > Encyclopedia > Methanol

Methanol

Methanol structure

Methanol 

structure
  • CAS No:

    67-56-1

  • Formula:

    CH4O

  • Chemical Name:

    Methanol

  • Synonyms:

    METHYL RED MIXED SOLUTION;METHYL RED, WATER SOLUBLE;METHYL RED, SPIRIT SOLUBLE;METHYL RED SOLUTION R;CI NO 13020;Methanol, ECD tested for pesticide analysis, for residue analysis, 99.8%;Methanol, extra pure, 99+%;Methanol, for analysis ACS, 99.8+%

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Methanol is a clear, colorless liquid with a characteristic pungent odor (NTP NIEHS web accessed 2/16/2013). The air odor threshold has been reported as 1500 ppm (approximately 2000mg/m3), much higher than the occupational guidelines.Methanol (methyl alcohol; wood alcohol) is used extensively as a solvent for lacquers, paints, varnishes, cements, inks, dyes, plastics, and various industrial coatings. Large quantities are used in the production of formaldehyde and other chemical derivatives such as acetic acid, methyl halides and terephthalate, methyl methacrylate, and methylamines. Methanol is also used as a gasoline additive, as a component of lacquer thinners, in antifreeze preparations of the “nonpermanent” type, and in canned heating preparations of jellied alcohol. It is also used in duplicating fluid, in paint removers, and as a cleaning agent. The potential for methanol as a future alternative for gasoline indicates that the use of this chemical will most likely increase rather than decrease. At room temperature, methanol is a colorless liquid with a pungent odor. It is relatively volatile, with a vapor pressure of 96 mmHg and a vapor density of 1.11. It is miscible with water and soluble with other organic solvents. It is found in nature as a fermentation product of wood and as a constituent of some fruits and vegetables.


Methyl alcohol, also known as methanol or wood alcohol, is a clear, colorless, flammable liquid that is the simplest alcohol.World production of methanol is approximately 8.5 billion gallons annually. Methanol is produced industrially, starting with the production of synthesis gas or syngas. Syngas used in the production of methyl alcohol is a mixture of carbon monoxide and hydrogen formed when natural gas reacts with steam or oxygen. Methyl alcohol is then synthesized from carbon monoxide and hydrogen.Methyl alcohol is poisonous and is commonly used to denature ethyl alcohol. Methanol poisoning results from ingestion, inhalation of methanol vapors, or absorption through the skin. Methanol is transformed in the body to formaldehyde (H2CO) by the enzyme alcohol dehydrogenase.The formaldehyde is then metabolized to formic acid (HCOOH)by aldehyde dehydrogenase.


Methanol is a clear, water-white liquid with a mild odor at ambient temperatures.The air odor threshold for methanol has been reported as 100 ppm . Others have reported that 2000 or 5900 ppm methanol is barely detectable .


It was first isolated in 1661 by the Irish chemist Robert Boyle (1627–1691) who prepared it by the destructive distillation of boxwood, giving it the name spirit of box, and the name wood alcohol is still used for methyl alcohol. Methyl alcohol is also called pyroxylic spirit; pyroxylic is a general term meaning distilled from wood and indicates that methyl alcohol is formed during pyrolysis of wood. The common name was derived in the mid-1800s. The name methyl denotes the single carbon alkane methane in which a hydrogen atom has been removed to give the methyl radical. The word alcohol is derived from Arabic al kuhul.


ChEBI: Methanol is the primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group. It has a role as an amphiprotic solvent, a fuel, a human metabolite, an Escherichia coli metabolite, a mouse metabolite and a Mycoplasma genitalium metabolite. It is an alkyl alcohol, a one-carbon compound, a volatile organic compound and a primary alcohol. It is a conjugate acid of a methoxide.

Methanol Basic Attributes

32.04

1098229

200-659-6

TSCA listed

<10(APHA)

2905 11 00

Characteristics

λ: 210 nm Amax: 0.50λ: 220 nm Amax: 0.30λ: 230 nm Amax: 0.15λ: 235 nm Amax: 0.10λ: 240 nm Amax: 0.05λ: 260 nm Amax: 0.01λ: 400 nm Amax: 0.01

Clear, colorless liquid with a characteristic alcoholic odor. Odor threshold concentrations ranged from 8.5 ppbv(Nagata and Takeuchi, 1990) to 100.0 ppmv(Leonardos et al., 1969). Experimentally determined detection and recognition odor threshold concentrations were 5.5 mg/m3(4.2 ppmv) and 69 mg/m3(53 ppmv), respectively (Hellman and Small, 1974).

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization:Not pertinent; Inhibitor of Polymerization: Not pertinent.

0.791 g/mL at 25 °C

-98 °C(lit.)

64,7°C

n20/D1.329(lit.)

miscible

410 mm Hg ( 50 °C)

1.11 (vs air)

LD50 oral (rat)5628 mg/kgLD50 skin (rabbit)15,840 mg/kgLC50 inhal (rat)>145,000 ppm (1 h)PEL (OSHA)200 ppm (260 mg/m3)TLV-TWA (ACGIH)200 ppm (260 mg/m3)—skinSTEL (ACGIH)250 ppm (328 mg/m3)

Methanol is a flammable liquid (NFPA rating = 3) that burns with an invisible flame in daylight; its vapor can travel a considerable distance to an ignition source and "flash back." Methanol-water mixtures will burn unless very dilute. Carbon dioxide or dry chemical extinguishers should be used for methanol fires.

Faint alcohol odor detectable at 4 to 6000 ppm (mean = 160 ppm)

6.8 (20°C in H2O)

15.2(at 25℃)

4.99 at 25 °C (headspace-GC, Gupta et al., 2000)

Methanol reacts violently with acetyl bromide [Merck 11th ed. 1989]. Mixtures with concentrated sulfuric acid and concentrated hydrogen peroxide can cause explosions. Reacts with hypochlorous acid either in water solution or mixed water/carbon tetrachloride solution to give methyl hypochlorite, which decomposes in the cold and may explode on exposure to sunlight or heat. Gives the same product with chlorine. Can react explosively with isocyanates under basic conditions. The presence of an inert solvent mitigates this reaction [Wischmeyer 1969]. A violent exothermic reaction occurred between methyl alcohol and bromine in a mixing cylinder [MCA Case History 1863. 1972]. A flask of anhydrous lead perchlorate dissolved in Methanol exploded when Methanol was disturbed [J. Am. Chem. Soc. 52:2391. 1930]. P4O6 reacts violently with Methanol. (Thorpe, T. E. et al., J. Chem. Soc., 1890, 57, 569-573). Ethanol or Methanol can ignite on contact with a platinum-black catalyst. (Urben 1794).

385 °C

2-8°C

Safety Information

II

3

1

Xn,T,F

36/37-7-45-16-24/25-23-24-26

PC1400000

Methanol should be used only in areas free of ignition sources, and quantities greater than 1 liter should be stored in tightly sealed metal containers in areas separate from oxidizers.

10-20/21/22-68/20/21/22-39/23/24/25-23/24/25-11-40-36-36/38-23/25

Methanol reacts violently with strong oxidizers, causing a fire and explosion hazard.

UN 1230

Behavior in Fire: Containers may explode.

Toxicity

ACGIH TLV-TWA:(200 ppm)OSHA PEL-TWA:200 ppm (260 mg/m³)NIOSH REL-TWA:200 ppm;REL-STEL:250 ppm;REL-IDLH:25,000 ppm

Drug Information

Ingestion of adulterated alcoholic beveragescontaining methanol has resulted in innumerable loss of human lives throughout theworld. It is highly toxic, causing acidosis andblindness. The symptoms of poisoning arenausea, abdominal pain, headache, blurredvision, shortness of breath, and dizziness.In the body, methanol oxidizes to formaldehyde and formic acid — the latter could bedetected in the urine, the pH of which is lowered (when poisoning is severe).The toxicity of methanol is attributed tothe metabolic products above. Ingestion inlarge amounts affects the brain, lungs, gastrointestinal tract, eyes, and respiratory system and can cause coma, blindness, anddeath. The lethal dose is reported to be60–250 mL. The poisoning effect is prolonged and the recovery is slow, often causing permanent loss of sight.Other exposure routes are inhalation andskin absorption. Exposure to methanol vaporto at 2000 ppm at regular intervals over aperiod of 4 weeks caused upper respiratorytract irritation and mucoid nasal discharge inrats. Such discharge was found to be a doserelated effect.Inhalation in humans may produce headache, drowsiness, and eye irritation. Prolonged skin contact may cause dermatitis andscaling. Eye contact can cause burns anddamage vision..

Methanol Use and Manufacturing

Uses

Methanol is an important chemical raw material for fine chemicals. Its carbonylation at 3.5 MPa and 180-200° C in the presence of catalyst can produce acetic acid and further produce acetic anhydride. It reacts with syngas to prepare vinyl acetate in the presence of catalyst; reacts with isobutylene to produce tert-butyl methyl ether; prepare dimethyl oxalate through oxidization and carbonylation, and a further hydrogenation to produce ethylene glycol; reacts with toluene under catalyst and simultaneous oxidization to produce phenylethyl alcohol. It can be used as a good solvent, as a pesticide raw material, as an antifreeze agent, as a fuel and fuel additive (this is receiving increasing attention in environmental protection field). It is the main raw material in the preparation of formaldehyde, the raw material in medicine and spices production, a solvent in dyes and paint industries, the raw material in preparation of methanol single cell protein and synthesis of methyl ester.IndustryApplicationsRole/BenefitLaboratoryHPLC, UV/VIS spectroscopy, and LCMSLow UV cutoffChemical manufactureProduction of formaldehyde and its derivatesMain feedstockProduction of hydrocarbon chains and even aromatic systemsMain feedstockProduction of methyl tert-butyl etherMethylation reagentProduction of dimethyl terephthalic acid, methyl methacrylate and acrylic acid methyl esterMain feedstockPlasticsProduction of polymersMain feedstockFarm chemicalProduction of insecticide and acaricideMain feedstockPharmaceuticalsProduction of sulfonamides, amycin, etcMain feedstockFuel for vehiclesPure methanol fuelPure methanol does not produce an opaque cloud of smoke in the event of an accidentMethanol gasolineBlended directly into gasoline to produce a high-octane, efficient fuel with lower emissions than conventional gasolineChemical analysisDetermination of boronAnalysis agentDetermination of trace moisture in alcohols, saturated hydrocarbons, benzene, chloroform, pyridineAnalysis agentOthersSeparation of calcium sulfate and magnesium sulfateSeparation reagentSeparation of strontium bromide and barium bromideSeparation reagentAnti-freezing agentEffective component


Methanol has numerous uses. Its main use is in the production of formaldehyde, whichconsumes approximately 40% of methanol supplies. Methanolis a common organic solvent found in many products including deicers (windshield wiperfl uid), antifreezes, correction fl uid, fuel additives, paints, and other coatings. A number ofindustrial chemicals use methanol in their production. Among these are methyl methacrylateand dimethyl terephthalate. Methanol is used to convert methylacrylamide sulfate to methylmethacrylate and ammonium hydrogen sulfate (NH4HSO4):Methanol is used in making the ester dimethyl terephthalate from mixtures ofxylene of toluene. Dimethyl terephthalate is used in the manufacture of polyesters and plastics.Methanol is used as a fuel additive. The common gasoline additive HEET is pure methanoland is used as a gas-line antifreeze and water remover. Methanol is used as a fuel in camp stoves and small heating devices. It is used to fuel the small engines used in models (airplanes,boats). In the early history of automobiles,methanol was a common fuel. The availability of cheap gasoline replaced methanol in the1920s, but it is receiving renewed interest as an alternative fuel as the demand and cost of oilincrease and oil supplies become uncertain. Methanol can be produced from coal and biomass.Methanol has a higher octane rating and generally lower pollutant emissions compared togasoline. The relatively low flame temperature means that fewer nitrogen oxides are producedby methanol than by ethanol. One large disadvantage of methanol is that it has a lower energydensity than gasoline. Using equivalent volumes of gasoline and methanol, methanol givesabout half the mileage of gasoline. Another problem with methanol is its low vapor pressure,resulting in starting problems on cold days. This problem can be mitigated by using a blendof 85% methanol and 15% gasoline. This mixture is called M85 and is similar to E85 ethanol(see Ethyl Alcohol).


Methanol is used in the production offormaldehyde, acetic acid, methyl tert-butylether, and many chemical intermediates; asan octane improver (in oxinol); and as apossible alternative to diesel fuel; being anexcellent polar solvent, it is widely used as acommon laboratory chemical and as a methylating reagent.


high purity grade for ICP-MS detection


Methylalcohol, CH30H, also known as methanol or wood alcohol, is a colorless, toxic, flammable liquid with a boiling point of 64.6 °C(147 °F). The principal toxic effect is on the nervous system,particularly the retinae. Methyl alcoholis miscible in all proportions with water,ethyl alcohol, and ether. It burns with a light blue flame producing water and carbon dioxide. This vapor forms an explosive mixture(6.0 to 36.5% by volume) with air. Methyl alcohol is an important inexpensive raw material that is synthetically produced for the organic chemical industry. Nearly half of the methyl alcohol manufactured is used in the production of formaldehyde. Other uses of methyl alcohol are as an antifreeze and fuel for automobiles and as an intermediate in the production of synthetic protein.

Production

Modern industrial-scale methanol production is exclusively based on synthesis from pressurized mixtures of hydrogen, carbon monoxide, and carbon dioxide gases in the presence of catalysts. Based on production volume, methanol has become one of the largest commodity chemicals produced in the world.

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