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CAS: 109-87-5
MF: C3H8O2
MW: 76.09
EINECS: 203-714-2
General Description
Dimethoxymethane is a biodegradable dimethyl acetal.
Dimethoxymethane can be synthesized by acid catalyzed condensation of formaldehyde with methanol.
Dimethoxymethane is amphiphilic in nature with low viscosity, surface tension and boiling point.
Dimethoxymethane is a flammable, highly volatile solvent with good dissolving power.
Dimethoxymethane is considered as a potential alternative fuel and fuel additive due to its high oxygen content and its ability to enhance the combustion characteristics of diesel and petrol.
Dimethoxymethane's thermal diffusivity has been determined by photoacoustic method.
Analysis of the molecular structure of Dimethoxymethane by electron diffraction technique shows that it has C2 symmetry with a gauche-gauche conformation.
Dimethoxymethane is an acetal that is the dimethyl acetal derivative of formaldehyde.
Dimethoxymethane is an acetal and a diether.
Dimethoxymethane derives from a methanediol.
Dimethoxymethane, an acetal, is incompatible with strong oxidizing agents and acids .
Breaks down to formaldehyde and methanol in acidic solutions.
Dimethoxymethane is a very dangerous fire hazard when exposed to heat, flame or oxidizing agents.
May ignite or explode if heated with oxygen.
Moderately explosive when exposed to heat or flame.
May ignite or explode when heated with oxygen.
To fight fire, use foam, CO2, dry chemical.
When heated to decomposition Dimethoxymethane emits acrid smoke and irritating fumes.
Dimethoxymethane, also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power.
Dimethoxymethane has a chloroform-like odor and a pungent taste.
Dimethoxymethane is the dimethyl acetal of formaldehyde.
Dimethoxymethane is soluble in three parts water and miscible with most common organic solvents.
Dimethoxymethane, also called methylal, is a clear colorless flammable liquid with a low boiling point, low viscosity and an excellent dissolving power.
Moderately toxic by subcutaneous route.
Mildly toxic by ingestion and inhalation.
Can cause injury to lungs, liver, kidneys, and the heart.
A narcotic and anesthetic in high concentrations.
Dimethoxymethane is considered to be of low hazard potential to humans given that no adverse effects or organ-specific toxicity were observed at inhalation exposures as high as 10 068 ppm (31 334 mg/m3) in rats, and considering the available information indicating a lack of genotoxic, mutagenic or developmental effects.
As Dimethoxymethane is considered to be of low hazard potential, the risk to human health is considered to be low.
Dimethoxymethane Chemical Properties
Melting point: -105 °C
Boiling point: 41-43 °C
Density: 0.860 g/mL at 20 °C(lit.)
Vapor density: 2.6 (vs air)
Vapor pressure: 6.38 psi ( 20 °C)
Refractive index: n20/D 1.354
Fp: -18 °C
Storage temp.: Store at <= 20°C.
Solubility: 32.3 g/100 mL (16°C)
Form: Liquid
pka: 3.1[at 20 ℃]
Color: Clear colorless
Odor: Mild, ethereal; chloroform-like.
PH: pH (12.5vol % , 25℃) : 4.5～6.6
Explosive limit: 1.6-17.6%(V)
Water Solubility: 32.3 g/100 mL (16 ºC)
Sensitive: Moisture Sensitive
Merck: 14,6012
BRN: 1697025
Henry's Law Constant (x 10-4 atm?m3/mol): 1.73 at 25 °C (Hine and Mookerjee, 1975)
Exposure limits NIOSH REL: TWA 1,000 ppm (3,100 mg/m3), IDLH 2,200 ppm; OSHA PEL: TWA 1,000 ppm; ACGIH TLV: TWA 1,000 ppm (adopted).
Stability: Stable. Extremely flammable.
Readily forms explosive mixtures with air.
Note low flash point and wide explosive limits.
Incompatible with strong oxidizing agents, strong acids.
May form explosive peroxides upon exposure to air.
LogP: 0
CAS DataBase Reference: 109-87-5(CAS DataBase Reference)
NIST Chemistry Reference: Methane, dimethoxy-(109-87-5)
EPA Substance Registry System: Dimethoxymethane (109-87-5)
Dimethoxymethane, also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power.
Dimethoxymethane is stable in the presence of alkalis and mild acids, and to high temperatures and pressures.
Dimethoxymethane differs from other ethers in that it forms only minute omounts of peroxides.
Dimethoxymethane will dissolve such synthetic resins as nitrocellulose, cellulose acetate and propionate, ethyl cellulose, vinyl, "Epons" and polystyrene, and also many of the natural gums and waxes.
Dimethoxymethane as a latent solvent is activated by the addition of esters, ketones or alcohols.
Dimethoxymethane's evaporation rate, twice that of acetone, places this ether in a class with such solvents as acetone, methyl acetate and ethyl acetate in resin formulations.
Dimethoxymethane appears as a clear colorless liquid with a pungent, 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.
Uses
Dimethoxymethane is a valuable extraction solvent for pharmaceutical products and a stable, inexpensive solvent for Grignard reactions.
Dimethoxymethane is stable under alkaline and mild acidic conditions.
Dimethoxymethane's dissolving ability is stronger than ether, acetone, and methanol and azeotrope can dissolve nitrocellulose with high nitrogen content.
Dimethoxymethane is mainly used in the production of anion-exchange resins, and also as solvents and special fuels.
Dimethoxymethane is a versatile chemical with applications in many industries such as paints, perfume, resins, pharmacy, paint strippers, protective coatings, and fuel additives.
Dimethoxymethane may be used in the synthesis of methoxymethyl (MOM) ethers.
Dimethoxymethane may also be used as an external cross-linker to form microporous polymers.
Reaction solvent or an extraction solvent manufacturing pharmaceuticals, aerosols, paints, varnishes and cleanings.
Production of ion exchange resins, polyacetal as a chain length regulator.
Glue Formulations fragrances and pesticides.
Fuel Additive for smoke reduction.
Blowing agent for PU Foams.
Industrially, Dimethoxymethane is primarily used as a solvent and in the manufacture of perfumes, resins, adhesives, paint strippers and protective coatings.
Another application is as a gasoline-additive for increasing octane number.
Dimethoxymethane can also be used for blending with diesel.
Preparation
Dimethoxymethane can be manufactured by oxidation of methanol or by the reaction of formaldehyde with methanol.
In aqueous acid, Dimethoxymethane is hydrolyzed back to formaldehyde and methanol.
Due to the anomeric effect, dimethoxymethane 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 Dimethoxymethane 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.
Another useful application of dimethoxymethane 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.
Purification Methods
Dimethoxymethane is a volatile flammable liquid which is soluble in three parts of H2O, and is readily hydrolysed by acids.
Purify it by shaking with an equal volume of 20% aqueous NaOH, stand for 20minutes, dry over fused CaCl2, filter and fractionally distil Dimethoxymethane through an efficient column.
Store Dimethoxymethane over molecular sieves.
Fire Hazard
A very dangerous fire hazard when exposed to heat, flame, or oxidzers.
Moderately explosive when exposed to heat or flame.
May ignite or explode when heated with oxygen.
To fight fire, use foam, CO2, dry chemical.
When heated to decomposition it emits acrid smoke and irritating fumes.
Reactivity Profile
Dimethoxymethane, an acetal, is incompatible with strong oxidizing agents and acids .
Breaks down to formaldehyde and methanol in acidic solutions.
A very dangerous fire hazard when exposed to heat, flame or oxidizing agents.
May ignite or explode if heated with oxygen.
Irritating to eyes, nose and throat.
Harmful if inhaled.
LIQUID: Irritating to skin and eyes.
Harmful if swallowed.
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
DTXSID1025564
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)
