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METHYLAL
CAS: 109-87-5
European Community (EC) Number: 203-714-2
FORMULA: CH₃OCH₂OCH₃
CONVERSION: 1 ppm = 3.11 mg/m3
Dimethoxymethane, also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power.
Methylal has a chloroform-like odor and a pungent taste.
Methylal is the dimethyl acetal of formaldehyde.
Methylal is soluble in three parts water and miscible with most common organic solvents.
Methylal is an acetal that is the dimethyl acetal derivative of formaldehyde.
Methylal is an acetal and a diether.
Methylal is functionally related to a methanediol.
Methylal is a colorless liquid with a chloroform-like odor.
Methylal is an ether.
Methylal is a colorless, flammable, volatile liquid, C3H8O2, having a chloroformlike odor, used chiefly as a solvent, in perfumery, and in organic synthesis.
Methylal, also known as Dimethoxymethane or Formaldehyde dimethyl ether, is the dimethyl acetal of formaldehyde used as a solvent as well as in manufacturing resins, perfumes, adhesives, and protective coatings.
Ungraded products are indicative of a grade suitable for general industrial use or research purposes and typically are not suitable for human consumption or therapeutic use.
Methylal, also known, as dimethoxymethane is widely used as a solvent and in the manufacture of perfumes, resins, adhesives.
Besides methylal is applied to increase the octane number of gasoline.
Methylal is a volatile flammable liquid C3H8O2 of pleasant ethereal odor used as a hypnotic and anesthetic and in organic synthesis
General description of Dimethoxymethane:
Methylal (DMM, methylal) is a biodegradable dimethyl acetal.
Methylal can be synthesized by acid catalyzed condensation of formaldehyde with methanol.
Methylal is amphiphilic in nature with low viscosity, surface tension and boiling point.
Methylal is the dimethyl acetal of formaldehyde.
Methylal is soluble in three parts water and miscible with most common organic solvents.
Methylal can be manufactured by oxidation of methanol or by the reaction of formaldehyde with methanol.
In aqueous acid, Methylal is hydrolyzed back to formaldehyde and methanol.
Methylal is primarily used as a solvent and in the manufacture of perfumes, resins, adhesives, paint strippers and protective coatings.
Due to the anomeric effect, Methylal has a preference toward the gauche conformation around the C–O bonds, instead of the anti conformation.
Since Methylal is one of the smallest molecules exhibiting this effect, which has great interest in carbohydrate chemistry, dimethoxymethane is often used for theoretical studies of the anomeric effect.
Product Benefits
• Easy handling
• Boiling point: 42°C
• Miscible with all polyols
• Stable in water-based polyurethane systems
• Blowing ability similar to pentanes
• Used alone or as co-blowing agent
• Lowest flammability among the flammable options
• Attractive cost
Sources/Uses
Methylal is used as a solvent for adhesives and coatings, a fuel, and an intermediate for other organic compounds.
Methylal has been used as an anesthetic.
Methylal appears as a clear colorless liquid with a chloroform-like odor.
Flash point 0 °F.
Boiling point 42.3 °C.
Density 0.864 g / cm3 at 68 °F (20 °C).
Vapors heavier than air.
Applications:
Industrially, Methylal is primarily used as a solvent and in the manufacture of perfumes, resins, adhesives, paint strippers and protective coatings.
Another application of Methylal is as a gasoline-additive for increasing octane number.
Methylal can also be used for blending with diesel.
Reagent in organic synthesis:
Another useful application of Methylal is to protect alcohols with a methoxymethyl (MOM) ether in organic synthesis.
This can be done using phosphorus pentoxide in dry dichloromethane or chloroform.
This is a preferred method to using chloromethyl methyl ether (MOMCl).
Alternatively, MOMCl can be prepared as a solution in a methyl ester solvent by reacting dimethoxymethane and an acyl chloride in the presence of a Lewis acid catalyst like zinc bromide:
MeOCH2OMe + RC(=O)Cl → MeOCH2Cl + RC(=O)(OMe)).
The solution of the reagent can be used directly without purification, minimizing contact with the carcinogenic chloromethyl methyl ether.
Unlike the classical procedure, which uses formaldehyde and hydrogen chloride as starting materials, the highly carcinogenic side product bis(chloromethyl) ether is not generated.
PHYSICAL & CHEMICAL INFORMATION:
Formula: C3H8O2 / CH2-(OCH3)2
Molecular mass: 76.1
Boiling point: 42°C
Melting point: -105°C
Density: 0.86 g/cm³
Solubility in water, g/100ml at 20°C: 28.5 (good)
Vapour pressure, kPa at 20°C: 42.6
Relative vapour density (air = 1): 2.6
Relative density of the vapour/air-mixture at 20°C (air = 1): 1.7
Flash point: -31°C c.c.
Auto-ignition temperature: 235°C
Explosive limits, vol% in air: 2.2 - 19.9
Octanol/water partition coefficient as log Pow: 0.18
Synthesis and structure:
Methylal can be manufactured by oxidation of methanol or by the reaction of formaldehyde with methanol.
In aqueous acid, Methylal is hydrolyzed back to formaldehyde and methanol.
Due to the anomeric effect, Methylal has a preference toward the gauche conformation with respect to each of the C–O bonds, instead of the anti conformation.
Since there are two C–O bonds, the most stable conformation is gauche-gauche, which is around 7 kcal/mol more stable than the anti-anti conformation, while the gauche-anti and anti-gauche are intermediate in energy.
Since it is one of the smallest molecules exhibiting this effect, which has great interest in carbohydrate chemistry, Methylal is often used for theoretical studies of the anomeric effect.
“Gas-to-liquids” catalytic conversion technologies show promise for liberating stranded natural gas reserves and for achieving energy diversity worldwide.
Some gas-to-liquids products are used as transportation fuels and as blendstocks for upgrading crude-derived fuels.
Methylal (CH3-O-CH2-O-CH3), also known as dimethoxymethane or DMM, is a gas-to-liquid chemical that has been evaluated for use as a diesel fuel component.
Methylal contains 42% oxygen by weight and is soluble in diesel fuel.
The physical and chemical properties of neat methylal and for blends of methylal in conventional diesel fuel are presented.
Methylal was found to be more volatile than diesel fuel, and special precautions for distribution and fuel tank storage are discussed.
Steady state engine tests were also performed using an unmodified Cummins B5.9 turbocharged diesel engine to examine the effect of methylal blend concentration on performance and emissions.
Substantial reductions of particulate matter emissions have been demonstrated for 10 to 30% blends of methylal in diesel fuel.
This research indicates that methylal may be an effective blendstock for diesel fuel provided design changes are made to vehicle fuel handling systems.
PHYSICAL DESCRIPTION: Colorless liquid with a chloroform-like odor.
MOLECULAR WEIGHT: 76.1
BOILING POINT: 111°F
FREEZING POINT: -157°F
SOLUBILITY: 33%
VAPOR PRESSURE: 330 mmHg
IONIZATION POTENTIAL: 10.00 eV
SPECIFIC GRAVITY: 0.86
FLASH POINT: (oc) -26°F
UPPER EXPLOSIVE LIMIT: 13.8%
LOWER EXPLOSIVE LIMIT: 2.2%
INCOMPATIBILITIES & REACTIVITIES: Strong oxidizers, acids
STORAGE
Fireproof.
Separated from strong oxidants and strong bases.
Cool.
Keep in the dark.
Well closed.
Store only if stabilized.
Store in an area without drain or sewer access.
Keep away from heat, sparks, and flame. Keep away from sources of ignition.
Do not store in direct sunlight.
Store in a tightly closed container.
Store in a cool, dry, well-ventilated area away from incompatible substances.
Flammables-area.
SYNONYMS:
Dimethoxymethane
METHYLAL
109-87-5
Formal
Methane, dimethoxy-
Formaldehyde dimethyl acetal
Dimethyl formal
Anesthenyl
2,4-Dioxapentane
Methylene dimethyl ether
Bis(methoxy)methane
Methoxymethyl methyl ether
Metylal
Formaldehyde methyl ketal
Formaldehyde dimethylacetal
bis(methyloxy)methane
Methylene glycol dimethylether
7H1M4G2NUE
CHEBI:48341
Dimethoxy methane
Metylal [Polish]
HSDB 1820
EINECS 203-714-2
UN1234
UNII-7H1M4G2NUE
Dimethylformal
AI3-16096
CCRIS 9397
Methylene Glycol Dimethyl Ether
Dimethoxy-Methane
Methylenedioxydimethane
METHYLAL [HSDB]
METHYLAL [INCI]
METHYLAL [MI]
Dimethylacetal formaldehyde
METHYLAL [WHO-DD]
EC 203-714-2
CHEMBL15537
(CH3O)2CH2
Polyoxymethylene dimethyl ethers
DTXSID1025564
DTXSID101337651
ZINC2005853
MFCD00008495
AKOS000120977
ZINC112926527
UN 1234
Dimethoxymethane, ReagentPlus(R), 99%
Methylal [UN1234] [Flammable liquid]
D0637
FT-0625028
Formaldehyde dimethyl acetal, analytical standard
Q411496
J-520340
F0001-0207
Formaldehyde dimethyl acetal, for Grignard reactions, >=99.0% (GC)
Formaldehyde dimethyl acetal, absolute, over molecular sieve (H2O <=0.01%), >=99.0% (GC)
