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Methanol

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Name

Methanol

EINECS 200-659-6
CAS No. 67-56-1 Density 0.753 g/cm3
PSA 20.23000 LogP -0.39150
Solubility miscible with water Melting Point -98 °C(lit.)
Formula CH4O Boiling Point 48.093 °C at 760 mmHg
Molecular Weight 32.0422 Flash Point 11.111 °C
Transport Information UN 1170 3/PG 2 Appearance Clear, colorless liquid
Safety 36/37-7-45-16-24/25-23-24 Risk Codes 10-20/21/22-68/20/21/22-39/23/24/25-23/24/25-11-40-36-36/38-23/25
Molecular Structure Molecular Structure of 67-56-1 (Methanol) Hazard Symbols HarmfulXn, ToxicT, FlammableF
Synonyms

Alcohol, methyl;Carbinol;Methanol cluster;Bieleski's solution;Methyl alcohol;Wood alcohol;

Article Data 2114

Methanol Synthetic route

64-18-6

formic acid

67-56-1

methanol

Conditions
ConditionsYield
With water In aq. phosphate buffer at 20℃; for 1h; pH=7.4; Catalytic behavior; Reagent/catalyst; Electrolysis; Inert atmosphere; Enzymatic reaction;100%
With cobalt(III) acetylacetonate; hydrogen; bis(trifluoromethanesulfonyl)amide; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran; ethanol at 100℃; under 52505.3 Torr; for 24h; Autoclave; Inert atmosphere;59%
With C36H54IrN2P2(1+)*C24H20B(1-); hydrogen; sodium hydride In ethanol; toluene at 180℃; under 7500.75 - 45004.5 Torr; for 18h; Autoclave;31%
93-58-3

benzoic acid methyl ester

104-76-7

2-Ethylhexyl alcohol

A

67-56-1

methanol

B

5444-75-7

Velate 368

Conditions
ConditionsYield
With phosphorus pentoxide; potassium carbonate; Aliquat 336 In neat (no solvent) under 20 Torr; for 8h; Product distribution; Ambient temperature;A n/a
B 100%
With phosphorus pentoxide; potassium carbonate; Aliquat 336 In neat (no solvent) under 20 Torr; for 8h; Ambient temperature;A n/a
B 100%
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

104-76-7

2-Ethylhexyl alcohol

A

67-56-1

methanol

B

63468-13-3

2-ethylhexyl methyl terephthalate

Conditions
ConditionsYield
With phosphorus pentoxide; potassium carbonate; Aliquat 336 In neat (no solvent) under 20 Torr; for 24h; Product distribution; Ambient temperature;A n/a
B 100%
With phosphorus pentoxide; potassium carbonate; Aliquat 336 In neat (no solvent) under 20 Torr; for 24h; Ambient temperature;A n/a
B 100%
124-38-9

carbon dioxide

67-56-1

methanol

Conditions
ConditionsYield
With D-glucose; NADH In aq. buffer for 2h; pH=6.85; Catalytic behavior; Solvent; Concentration; pH-value; Ionic liquid; Enzymatic reaction;100%
With carbon monoxide; water; hydrogen at 35 - 250℃; under 825.083 - 75007.5 Torr; Temperature; Pressure; Large scale;99.99%
With dimethylsulfide borane complex; C24H18BO2P In benzene-d6 at 70℃; under 1520.1 Torr; for 1h; Reagent/catalyst; Inert atmosphere;95%
29843-53-6

dimethyl(p-nitrophenyl)sulfonium perchlorate

A

67-56-1

methanol

B

701-57-5

1-methylthio-4-nitro-benzene

Conditions
ConditionsYield
With water at 80℃; Rate constant; other temp.;A n/a
B 100%
78371-05-8

2-methoxy-2-methyl nonane

A

67-56-1

methanol

B

78371-08-1

2-Iodo-2-methyl-nonane

Conditions
ConditionsYield
With Methyltrichlorosilane; sodium iodide In acetonitrile at 25℃; for 6h;A n/a
B 100%
113849-79-9

1-(2-Adamantylidene)-1-methoxy-1-phenylmethane

A

67-56-1

methanol

B

68157-27-7

adamantan-2-yl(phenyl)methanone

Conditions
ConditionsYield
With tris-p-bromophenyl ammoniumyl hexachloroantimonate In dichloromethane for 3h;A n/a
B 100%

acetic acid 4-[2-(4-acetoxy-phenyl)-1,2-dimethoxy-acenaphthen-1-yl]-phenyl ester

A

67-56-1

methanol

B

2,2-bis-(4-acetoxy-phenyl)-acenaphthen-1-one

Conditions
ConditionsYield
With trifluoroacetic acid In benzene for 0.5h; pinacol rearrangement;A n/a
B 100%
polyester

polyester

A

67-56-1

methanol

B

polyester

polyester

Conditions
ConditionsYield
With trifluoroacetic acid In benzene at 25℃; for 0.5h; pinacol rearrangement;A n/a
B 100%
93-58-3

benzoic acid methyl ester

104-54-1

3-Phenylpropenol

A

67-56-1

methanol

B

5320-75-2

cinnamyl benzoate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 100%

Methanol History

Pure methanol, however, was first isolated in 1661 by Robert Boyle, when he produced it via the distillation of boxwood. It later became known as pyroxylic spirit. In 1834, the French chemists Jean-Baptiste Dumas and Eugene Peligot determined its elemental composition. 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. In 1923, the German chemists Alwin Mittasch and Mathias Pier, working for BASF developed a means to convert synthesis gas (a mixture of carbon monoxide, carbon dioxide, and hydrogen) into methanol. 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 with the technology now owned by Johnson Matthey who is a leading licensor of methanol technology.
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 vehices" capable of operating on methanol or gasoline were introduced in the U.S. In 2006 astronomers using the MERLIN array of radio telescopes at Jodrell Bank Observatory discovered a large cloud of methanol in space, 300 billion miles across.

Methanol Consensus Reports

Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Methanol Standards and Recommendations

OSHA PEL: TWA 200 ppm; STEL 250 ppm (skin)
ACGIH TLV: TWA 200 ppm; STEL 250 ppm (skin); BEI: 15 mg/L of methanol in urine at end of shift
DFG MAK: 200 ppm (270 mg/m3); BAT: 30 mg/L in urine at end of shift
NIOSH REL: TWA 200 ppm; CL 800 ppm/15M
DOT Classification:  3; Label: Flammable Liquid, Poison

Methanol Analytical Methods

For occupational chemical analysis use NIOSH: Methanol, 2000.

Methanol Specification

Methanol, also known as methyl alcohol, is a colorless, flammable, toxic liquid with a faintly sweet pungent odor like that of ethyl alcohol. It is miscible with water, ethanol, ether, benzene, ketones, and most other organic solvents, and can dissolve many inorganic salts. Methanol is the simplest alcohol used in the manufacture of formaldehyde and acetic acid, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness. 

Physical properties about Methanol are: (1)ACD/LogP: -0.69; (2)ACD/LogD (pH 5.5): -0.69; (3)ACD/LogD (pH 7.4): -0.69; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 10.04; (7)ACD/KOC (pH 7.4): 10.04; (8)#H bond acceptors: 1; (9)Index of Refraction: 1.311 ; (10)Molar Refractivity: 8.217 cm3; (11)Molar Volume: 42.548 cm3; (12)Polarizability: 3.257 10-24cm3; (13)Surface Tension: 18.8619995117188 dyne/cm; (14)Density: 0.753 g/cm3; (15)Flash Point: 11.111 °C; (16)Enthalpy of Vaporization: 35.21 kJ/mol; (17)Boiling Point: 48.093 °C at 760 mmHg; (18)vapour Pressure: 265.414001464844 mmHg at 25°C

Preparation of Methanol: Before 1926, all methanol was made by distillation of wood. But now, almost all the industrial synthesis of methanol is using catalytic hydrogenation of carbon monoxide under pressure. This process includs gas making, synthetic purification, methanol synthesis and crude methanol rectification. The synthesis gas is most commonly produced from the methane component in natural gas rather than from coal. The purification process of crude methanol includes rectification and chemical treatment. Chemical treatment is using alkali to undermine the impurities which is difficult to be separated in the rectification process, and adjust the pH value. Rectification is removal of the main easily volatile components such as dimethyl ether, and difficultly volatile components such as ethanol, high-carbon alcohol and water. After the crude distillation, purity can achieve more than 98% .

Uses of Methanol:

1. Methanol is especially useful for HPLC, UV/VIS spectroscopy, and LCMS due to its low UV cutoff. It is also a basic organic raw material, which is mainly used to produce formaldehyde, acetic acid, methyl chloride, methylamine, dimethyl sulfate, pesticides (insecticides, acaricides), medicine (sulfonamides, syntomycin, etc.) and other organic products.

2. Methanol can also be mixed with gasoline for use of alternative fuels. The physical and chemical characteristics of methanol offer several advantages as an alternative fuel, including relatively low production cost and a lower risk of flammability compared to gasoline. But it is used on a limited basis to fuel internal combustion engines.

3. Methanol is an important solvent used for paint, varnish, shellac, ink, adhesives, dyes, alkaloids, cellulose acetate, cellulose nitrate, ethyl cellulose, polyvinyl butyral, etc. Methanol is a usually better solvent than ethanol. And it can dissolve many inorganic salts.

4. Methanol is also used as reagent for analysis and chromatography, as reagent of determination of boron, in separation of calcium sulfate and magnesium sulfate, and in separation of strontium bromide and barium bromide. What's more, it can used as antifreeze in pipelines and windshield washer fluid.

When you are using this chemical, please be cautious about it as the following: Methanol is harmful by inhalation, in contact with skin and if swallowed. If ingested, for example, as little as 10 mL of pure methanol can cause permanent blindness by destruction of the optic nerve, and 30 ml is potentially fatal. It has danger of very serious irreversible effects. Methanol is often a component in "bootleg" liquor (illegally brewed and distilled alcohol) and there have been numerous cases in the past in which the consumption of such a drink has been fatal. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) Methanol is highly flammable, so people should keep it away from sources of ignition. A hot air gun, a hot plate or even a radiator may be sufficiently hot to ignite the vapour of methanol. So people should be very careful.

You can still convert the following datas into molecular structure:
(1)SMILES:CO;
(2)Std. InChI:InChI=1S/CH4O/c1-2/h2H,1H3;
(3)Std. InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LCLo inhalation 44gm/m3/6H (44000mg/m3) BEHAVIORAL: FOOD INTAKE (ANIMAL)

BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 5, Pg. 1, 1933.
cat LDLo intravenous 4641mg/kg (4641mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 16, Pg. 1, 1920.
dog LDLo oral 7500mg/kg (7500mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1365, 1935.
frog LDLo parenteral 59gm/kg (59000mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 50, Pg. 296, 1935.
guinea pig LD50 intraperitoneal 3556mg/kg (3556mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
hamster LD50 intraperitoneal 8555mg/kg (8555mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
human LDLo oral 143mg/kg (143mg/kg) SENSE ORGANS AND SPECIAL SENSES: OPTIC NERVE NEUROPATHY: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: NAUSEA OR VOMITING
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 382, 1969.
human LDLo oral 428mg/kg (428mg/kg) BEHAVIORAL: HEADACHE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 74, 1974.
human TCLo inhalation 300ppm (300ppm) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

BEHAVIORAL: HEADACHE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 74, 1974.
human TCLo inhalation 86000mg/m3 (86000mg/m3) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: COUGH
Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 5, Pg. 1, 1933.
man LDLo oral 6422mg/kg (6422mg/kg) BRAIN AND COVERINGS: "CHANGES IN CIRCULATION (HEMORRHAGE, THROMBOSIS, ETC.)"

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: NAUSEA OR VOMITING
Canadian Medical Association Journal. Vol. 128, Pg. 14, 1983.
man LDLo unreported 868mg/kg (868mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TDLo oral 3571uL/kg (3.571mL/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BLOOD: OTHER CHANGES
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 2095, 1993.
man TDLo oral 9450uL/kg (9.45mL/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: GENERAL ANESTHETIC
American Journal of Emergency Medicine. Vol. 16, Pg. 538, 1998.
man TDLo oral 3429mg/kg (3429mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE Acta Medica Scandinavica. Vol. 212, Pg. 5, 1982.
monkey LCLo inhalation 1000ppm (1000ppm)   Industrial and Engineering Chemistry. Vol. 23, Pg. 931, 1931.
monkey LD50 oral 7gm/kg (7000mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA

BEHAVIORAL: COMA
Toxicology and Applied Pharmacology. Vol. 3, Pg. 202, 1961.
monkey LDLo skin 393mg/kg (393mg/kg)   Industrial and Engineering Chemistry. Vol. 23, Pg. 931, 1931.
mouse LCLo inhalation 50gm/m3/2H (50000mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 80, 1982.
mouse LD50 intraperitoneal 10765mg/kg (10765mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
mouse LD50 intravenous 4710mg/kg (4710mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
mouse LD50 oral 7300mg/kg (7300mg/kg)   Toxicology. Vol. 25, Pg. 271, 1982.
mouse LD50 subcutaneous 9800mg/kg (9800mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rabbit LD50 intraperitoneal 1826mg/kg (1826mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
rabbit LD50 intravenous 8907mg/kg (8907mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
rabbit LD50 oral 14200mg/kg (14200mg/kg)   FAO Nutrition Meetings Report Series. Vol. 48A, Pg. 105, 1970.
rabbit LD50 skin 15800mg/kg (15800mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 74, 1974.
rat LC50 inhalation 64000ppm/4H (64000ppm)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 74, 1974.
rat LD50 intraperitoneal 7529mg/kg (7529mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
rat LD50 intravenous 2131mg/kg (2131mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
rat LD50 oral 5628mg/kg (5628mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 19(11), Pg. 27, 1975.
women TDLo oral 4gm/kg (4000mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: NAUSEA OR VOMITING
Acta Medica Scandinavica. Vol. 212, Pg. 5, 1982.
 

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