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Dimethoxymethane (Methylal) is an acetal that is the dimethyl acetal derivative of formaldehyde.
Dimethoxymethane (Methylal) is an acetal and a diether.
Dimethoxymethane (Methylal) derives from a methanediol.
CAS: 109-87-5
MF: C3H8O2
MW: 76.09
EINECS: 203-714-2
Synonyms
DIMETHOXYMETHANE;DIMETHYLFORMAL;(CH3O)2CH2;2,4-Dioxapentane;Anesthenyl;bis(methoxy)methane;dimethoxy-methan;Dimethylacetal formaldehyde
Dimethoxymethane (Methylal) is a colorless liquid with a pungent odor.
Molecular weight= 76.11; Specific gravity (H2O:1)= 0.86;Boiling point=43.9℃; Freezing/Melting point=105℃; Vapor pressure 330 mmHg at 20℃; Flash point=32℃; Autoignition temperature=237℃.
Explosive limits: LEL= 2.2%; UEL= 13.8%.
Hazard Identification (based on NFPA-704 M Rating System): Health 2, Flammability 3, Reactivity 2. Soluble in water; solubility= 33%.
Dimethoxymethane (Methylal) is a biodegradable dimethyl acetal.
Dimethoxymethane (Methylal) can be synthesized by acid catalyzed condensation of formaldehyde with methanol.
Dimethoxymethane (Methylal) is amphiphilic in nature with low viscosity, surface tension and boiling point.
Dimethoxymethane (Methylal) is a flammable, highly volatile solvent with good dissolving power.
Dimethoxymethane (Methylal) 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 (Methylal)'s thermal diffusivity has been determined by photoacoustic method.
Analysis of the molecular structure of Dimethoxymethane (Methylal) by electron diffraction technique shows that it has C2 symmetry with a gauche-gauche conformation.
Dimethoxymethane (Methylal), also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power.
Dimethoxymethane (Methylal) has a chloroform-like odor and a pungent taste.
Dimethoxymethane (Methylal) is the dimethyl acetal of formaldehyde.
Dimethoxymethane (Methylal) is soluble in three parts water and miscible with most common organic solvents.
Dimethoxymethane (Methylal) is a colorless yet highly volatile acetal solvent that is manufactured from Methanol.
Dimethoxymethane (Methylal) is often used as a fuel, as a viscosity modifier, to manufacture other organic chemicals, and as a compatibilizer of actives in solvent and water based recipes.
Dimethoxymethane (Methylal) improves spray performance and reduces solvent amount in aerosol cans and pump sprays, and is a useful solvent in paint strippers, PU rigid foam, and as part of blowing systems.
Dimethoxymethane (Methylal) has an extremely low toxicity profile.
Dimethoxymethane (Methylal) is a biodegradable dimethyl acetal.
Dimethoxymethane (Methylal) can be synthesized by acid catalyzed condensation of formaldehyde with methanol.
Dimethoxymethane (Methylal) is amphiphilic in nature with low viscosity, surface tension and boiling point.
Dimethoxymethane (Methylal) is a flammable, highly volatile solvent with good dissolving power.
Dimethoxymethane (Methylal) 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 (Methylal)'s thermal diffusivity has been determined by photoacoustic method.
Analysis of the molecular structure of Dimethoxymethane (Methylal) by electron diffraction technique shows that it has C2 symmetry with a gauche-gauche conformation.
Dimethoxymethane (Methylal) is a colorless liquid.
Dimethoxymethane (Methylal) is the triester of ethanol and phosphoric acid and can be called "phosphoric acid, triethyl ester".is a clear colorless flammable liquid with a low boiling point, low viscosity and an excellent dissolving power.
Dimethoxymethane (Methylal) has a chloroform-like odor and a pungent taste.
Dimethoxymethane (Methylal) is the dimethyl acetal of formaldehyde.
Dimethoxymethane (Methylal) is soluble in three parts water and miscible with most common organic solvents.
Dimethoxymethane (Methylal) is primarily used as a solvent and in the manufacture of perfumes, resins, adhesives, paint strippers and protective coatings.
Another useful application of Dimethoxymethane (Methylal) is to protect alcohols with a MOM ether in organic synthesis.
Dimethoxymethane (Methylal), also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power.
Dimethoxymethane (Methylal) has a chloroform-like odor and a pungent taste.
Dimethoxymethane (Methylal) is the dimethyl acetal of formaldehyde. Dimethoxymethane is soluble in three parts water and miscible with most common organic solvents.
Synthesis and structure
Dimethoxymethane (Methylal) can be manufactured by oxidation of methanol or by the reaction of formaldehyde with methanol.
In aqueous acid, Dimethoxymethane (Methylal) is hydrolyzed back to formaldehyde and methanol.
Due to the anomeric effect, Dimethoxymethane (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 Dimethoxymethane (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.
Dimethoxymethane (Methylal) 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).
Dielectric constant: 2.7（20℃）
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: Dimethoxymethane (Methylal)(109-87-5)
EPA Substance Registry System: Dimethoxymethane (Methylal) (109-87-5)
Dimethoxymethane (Methylal), also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power.
Dimethoxymethane (Methylal) is stable in the presence of alkalis and mild acids, and to high temperatures and pressures.
Dimethoxymethane (Methylal) differs from other ethers in that it forms only minute omounts of peroxides.
Dimethoxymethane (Methylal) 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 (Methylal) as a latent solvent is activated by the addition of esters, ketones or alcohols.
Dimethoxymethane (Methylal)'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.
Physical properties
Dimethoxymethane (Methylal) 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 (Methylal) is a valuable extraction solvent for pharmaceutical products and a stable, inexpensive solvent for Grignard reactions.
Dimethoxymethane (Methylal) is stable under alkaline and mild acidic conditions.
Dimethoxymethane (Methylal)'s dissolving ability is stronger than ether, acetone, and methanol and azeotrope can dissolve nitrocellulose with high nitrogen content.
Dimethoxymethane (Methylal) is mainly used in the production of anion-exchange resins, and also as solvents and special fuels.
Dimethoxymethane (Methylal) may be used in the synthesis of methoxymethyl (MOM) ethers.
Dimethoxymethane (Methylal) may also be used as an external cross-linker to form microporous polymers.
Dimethoxymethane (Methylal) is a versatile chemical with applications in many industries such as paints, perfume, resins, pharmacy, paint strippers, protective coatings, and fuel additives.
Dimethoxymethane (Methylal) may be used in the synthesis of methoxymethyl (MOM) ethers.
Dimethoxymethane (Methylal) 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 (Methylal) 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 (Methylal) can also be used for blending with diesel.
Reagent in organic synthesis
Another useful application of Dimethoxymethane (Methylal) is to protect alcohols with a methoxymethyl (MOM) ether in organic synthesis.
Dimethoxymethane (Methylal) can be activated with phosphorus pentoxide in dichloromethane or chloroform.
This method is preferred to the use of chloromethyl methyl ether (MOMCl).
Phenols can also be MOM-protected using dimethoxymethane, p-toluenesulfonic acid.
Alternatively, MOMCl can be generated as a solution by treating dimethoxymethane with an acyl chloride in the presence of a Lewis acid catalyst like zinc bromide:
MeOCH2OMe + RC(=O)Cl → MeOCH2Cl + RC(=O)(OMe)).
Unlike the classical procedure, which uses formaldehyde and hydrogen chloride as starting materials, the highly carcinogenic side product bis(chloromethyl) ether is not generated.
Preparation
Dimethoxymethane (Methylal) synthesis is based on the liquid-phase acetalization reaction of methanol and formaldehyde.
Dimethoxymethane (Methylal) can be manufactured by oxidation of methanol or by the reaction of formaldehyde with methanol.
In aqueous acid, Dimethoxymethane (Methylal) is hydrolyzed back to formaldehyde and methanol.
Reactivity Profile
Dimethoxymethane (Methylal), 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.
