462-95-3

Usage

Uses

Used in Chemical Synthesis:
DEM is used as a chemical intermediate for its ability to act as an ethoxymethylating reagent for alcohols and phenols. It also serves as a source for formaldehyde in organic synthesis, making it a valuable component in the production of various chemicals.
Used in Lithium Batteries:
Diethoxymethane is used as a solvent in lithium batteries with nonaqueous electrolytes, contributing to their performance and efficiency.
Used in Polymer Industry:
DEM is utilized as a solvent for polymeric materials, aiding in the processing and manufacturing of various polymer-based products.
Used as a Fuel Additive:
Diethoxymethane is employed as a fuel additive to improve the characteristics and performance of fuels in different applications.
Used in Solvent Replacement:
DEM may be used as a substitute solvent to dichloromethane and toluene in the O-alkylation of different phenols in the presence of phase transfer catalysts (PTCs), offering an environmentally friendly alternative for certain chemical processes.

Synthesis Reference(s)

Synthetic Communications, 25, p. 3939, 1995 DOI: 10.1080/00397919508011470

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

DIETHOXYMETHANE, an acetal, is incompatible with strong oxidizing agents and acids. Breaks down to formaldehyde and ethanol in acidic solutions.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Highlyflammable

Safety Profile

Moderately toxic by ingestion. Flammable when exposed to heat or flame; can react vigorously with oxidizers. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C5H12O2/c1-3-6-5-7-4-2/h3-5H2,1-2H3

Upstream product

• 50-00-0 formaldehyd 
• 64-17-5 ethanol 
• 925-90-6 ethylmagnesium bromide 
• 859074-50-3 ethoxy-(β-bromo-β'-chloro-isopropoxy)-methane 
• 75-09-2 dichloromethane 
• 141-52-6 sodium ethanolate 
• 54699-20-6 1-ethoxy-1-(ethylthio)methane 
• 89583-61-9 2-chloro-1-(chloromethyl)ethyl ethoxymethyl ether 
• 627-03-2 3-oxapentanoic acid 
• 100-97-0 hexamethylenetetramine 
• 3188-13-4 ethyl chloromethyl ether 
• 766-15-4 4,4-dimethyl-1,3-dioxane 
• 141-78-6 ethyl acetate 
• 75-11-6 diiodomethane 

Downstream Products

• 87175-99-3 1,3-diethoxy-1-phenylpropane 
• 5648-29-3 1-(ethoxymethoxymethoxy)ethane 
• 4431-82-7 POME₃ 
• 60-29-7 diethyl ether 
• 75-07-0 acetaldehyde 
• 67-56-1 methanol 
• 34557-54-5 methane 
• 74-85-1 ethene 
• 591-22-0 3,5-Lutidine 
• 583-58-4 3,4-Lutidin 
• 101-77-9 4,4'-diamino diphenyl methane 
• 6630-39-3 2-bromo-1,1,3-triethoxy-propane 
• 891-77-0 N-Aethoxymethyl-2-hydroxy-5-phenyl-valeriansaeure-amid 
• 785-82-0 N-Aethoxymethyl-2-hydroxy-4-phenyl-but-3-ensaeure-amid 

Relevant academic research and scientific papers

Utilization of Formic Acid as C1 Building Block for the Ruthenium-Catalyzed Synthesis of Formaldehyde Surrogates

Dialkoxymethanes are becoming increasingly important as fuel additives, formaldehyde surrogates, and chemical intermediates, but the effective synthesis remains challenging. Herein, the catalytic synthesis of dialkoxymethane products using a molecular catalyst is reported. The catalytic system, comprising the [Ru(triphos)(tmm)] in combination with the Lewis acid Al(OTf)3, enables the direct synthesis of dialkoxymethane products with formic acid as C1 building block in high to excellent turnover numbers.

Enhanced Hydrogenation of Carbon Dioxide to Methanol by a Ruthenium Complex with a Charged Outer-Coordination Sphere

We report the hydrogenation of CO2 to MeOH by a Ru(triphos) catalyst containing a cationic tetraalkylammonium moiety in the outer coordination sphere. This catalyst affords higher TON and TOF values for MeOH than isostructural catalysts with neutral phosphine ligands. Kinetic data from operando NMR spectroscopy studies indicate the improvement in MeOH production arises from a 12-fold enhancement in the rate of hydrogenation of the transient formaldehyde intermediate. These results provide insight into the catalyst characteristics that promote MeOH formation.

Novel synthesis method of alkoxymethylamine compound

The invention relates to a novel synthesis method of an alkoxymethylamine compound. The novel synthesis method comprises the steps: (1) dehydrating formaldehyde HCHO and alcohol R1OH by carrying out an aldolization under the action of an acid catalyst to obtain dialkoxymethane; and (2) carrying out a hydrocarbylation reaction on dialkoxymethane obtained in step (1) and substituted amine R2-NH2 toremove alcohol to obtain an alkoxymethyl substituent amine compound N-R1 oxymethyl-N-R2 amine. The synthesis method disclosed by the invention is simple in operation and high in yield reaching 92% orabove; and compared with the prior art, the novel synthesis method has the advantages that no acid wastewater, waste salts and chloromethyl alkyl ether serving as a cancerogen are greatly generated, the environment protection cost is favorably reduced, and the industrial prospect is higher.

Effect of the Nature of the Catalyst on Catalytic Activity and Selectivity in the Formaldehyde Hydrogenation

The effect the nature of the carrier and supported metal on the activity and selectivity of the catalyst in the reaction of formaldehyde hydrogenation to methanol is studied. The formation of such oxygenates as ethanol, formic acid, and diethyl formal is observed. It is found that ethanol forms on Fe-containing alloyed catalyst, while formic acid forms on the catalysts containing Au. Thermodynamic calculations are performed for a series of side reactions that confirm the formation of the resulting oxygenates.

Three Binary Azeotropic Systems for 1-(Methoxymethoxy)-propane, 1-(Ethoxymethoxy)-propane, and Methoxy(methoxymethoxy)methane with Three Alcohols at 101.33 kPa: Experimental Data, Correlation, and Purification

The isobaric vapor-liquid equilibrium (VLE) data for three binary systems of 1-(methoxymethoxy)-propane and ethanol, 1-(ethoxymethoxy)-propane and 1-butanol, methoxy(methoxymethoxy)methane and 1-propanol at 101.33 kPa were measured using an improved Rose still. Three minimum boiling azeotropes were found for three binary systems containing ethanol, 1-butanol, and 1-propanol for which the azeotropic temperature and composition are 349.35 K and 70.95 mol % (ethanol), 384.02 K and 36.02 mol % (1-butanol), 368.68 K and 69.26 mol % (1-propanol), at 101.33 kPa, respectively. The VLE measurements were correlated by the Van Laar, Wilson, and nonrandom two-liquid models, and the results showed that the measurements had a good correlation by using thethree models for the three binary systems, respectively. The measurements of these three binary systems were thermodynamic as checked by the Herington semiempirical method.

Method for catalytically synthesizing diethoxymethane by ionic liquid

The invention discloses a method for catalytically synthesizing diethoxymethane by ionic liquid. The method takes the ionic liquid as a catalyst and takes formaldehyde and ethanol as reactants to react for 0.5h to 6h in a nitrogen atmosphere under conditions that the reaction temperature is 80 DEG C to 160 DEG C and the reaction pressure is 0.5Mpa to 5.0MPa; a positive ion part of the ionic liquid is selected from imidazole positive ions, pyridine positive ions, quaternary ammonium positive ions, quaternary phosphonate positive ions and heterocyclic positive ions. According to the method disclosed by the invention, raw materials are obtained from coal chemical industry and biomass and are cheap and easy to obtain; the catalyst has high activity, can be repeatedly used, has low corrosion and has no special requirements on equipment; reaction conditions are moderate, and reaction and separation processes are simple.

Br?nsted-acidic ionic liquids as efficient catalysts for the synthesis of polyoxymethylene dialkyl ethers

Acetalation of formaldehyde (HCHO) with dialkyl formal or aliphatic alcohol to prepare polyoxymethylene dialkyl ethers (RO(CH2O)nR, n ≥ 1) catalyzed by Br?nsted-acidic ionic liquids has been developed. The correlation between the structure and acidity activity of various ionic liquids was studied. Among the ionic liquids investigated, 1-(4-sulfonic acid)butyl-3-methylimidazolium hydrogen sulfate ([MIMBs]HSO4) exhibited the best catalytic performance in the reaction of diethoxymethane (DEM1) with trioxane. The influences of ionic liquid loading, molar ratio of DEM1 to HCHO, reaction temperature, pressure, time, and reactant source on the catalytic reaction were explored using [MIMBs]HSO4 as the catalyst. Under the optimal conditions of n([MIMBs]HSO4):n(DEM1):n(HCHO) = 1:80:80, 140 °C, and 4 h, the conversion of HCHO and selectivity for DEM2–8 were 92.6% and 95.1%, respectively. The [MIMBs]HSO4 catalyst could be easily separated and reused. A feasible mechanism for the catalytic performance of [MIMBs]HSO4 was proposed.

Tailor-made Molecular Cobalt Catalyst System for the Selective Transformation of Carbon Dioxide to Dialkoxymethane Ethers

Herein a non-precious transition-metal catalyst system for the selective synthesis of dialkoxymethane ethers from carbon dioxide and molecular hydrogen is presented. The development of a tailored catalyst system based on cobalt salts in combination with selected Triphos ligands and acidic co-catalysts enabled a synthetic pathway, avoiding the oxidation of methanol to attain the formaldehyde level of the central CH2 unit. This unprecedented productivity based on the molecular cobalt catalyst is the first example of a non-precious transition-metal system for this transformation utilizing renewable carbon dioxide sources.

Method for preparing diethoxymethane by supported heteropolyacid catalyst

The invention relates to a method for preparing diethoxymethane, in particular to a method for for preparing diethoxymethane by a supported heteropolyacid catalyst. According to the method, dimethoxymethane and ethanol are taken as raw materials, liquid acid and supported liquid acid are taken as catalysts, the preparation method of the supported heteropolyacid catalyst, for example 33% of H3PW12O40/SiO2, comprises the following steps that a phosphotungstic acid aqueous solution with the concentration of 33% by mass is used, SiO2 is taken as a carrier, the impregnation liquid volume is the approximate to the pore volume, a catalyst sample is obtained after the phosphotungstic acid aqueous solution and the SiO2 are mixed uniformly and stood at the normal temperature by 10h, the sample is dried at the temperature of 120 DEG C, and calcination is performed at the temperature of 350 DEG C to obtain the 33% of H3PW12O40/SiO2 catalyst by the mass is prepared. According to the method, the product is relatively simple, the selectivity is high, and the method has an excellent application prospect. The raw materials required by the method are easy to obtain, the whole process operation is simple, at the same time, the method doesn't produce any chemical substances polluting the environment, and the method belongs to the environment-friendly technology route.

Ruthenium-Catalyzed Synthesis of Dialkoxymethane Ethers Utilizing Carbon Dioxide and Molecular Hydrogen

The synthesis of dimethoxymethane (DMM) by a multistep reaction of methanol with carbon dioxide and molecular hydrogen is reported. Using the molecular catalyst [Ru(triphos)(tmm)] in combination with the Lewis acid Al(OTf)3resulted in a versatile catalytic system for the synthesis of various dialkoxymethane ethers. This new catalytic reaction provides the first synthetic example for the selective conversion of carbon dioxide and hydrogen into a formaldehyde oxidation level, thus opening access to new molecular structures using this important C1source.