HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethoxymethane
METHYLAL · FORMALDEHYDE DIMETHYL ACETAL · 1,1-DIMETHOXYMETHANE · FORMAL · Methyla · Methyl formal · DIMETHYLFORMAL · 2,4-Dioxapentane
Identifiers & Physical Properties
| CAS No. | 109-87-5 |
|---|---|
| Molecular formula | C3H8O2 |
| Average molar mass | 76.09 g/mol |
| Monoisotopic mass | 76.0524295 g/mol |
| SMILES | COCOC |
| InChIKey | NKDDWNXOKDWJAK-UHFFFAOYSA-N |
| PubChem CID | 8020 |
| ChEMBL | CHEMBL15537 |
| ChEBI | CHEBI:48341 |
| EC No. | 203-714-2 |
| DTXSID | DTXSID1025564 |
Chemical & Physical Properties
| XLogP | 0.2 |
|---|---|
| Topological polar surface area | 18.5 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 2 |
| Heavy atoms | 5 |
| Formal charge | 0 |
| Complexity | 12.4 |
| Chemical classes | Other Classes -> AcetalsFlammable agents - 3rd degreeVolatile Organic Compound (VOC) |
| Cosmetics | Solvent |
| SpringerMaterials Properties | Schoenflies notation |
| LogP (partition coefficient) | log Kow= 0.00.18 |
| Odor | CHLOROFORM ODORChloroform-like odor.Mild, etherealchloroform-like. |
| Taste | PUNGENT TASTE |
| Density | 0.861 at 68 °F (USCG, 1999) - Less dense than waterwill float0.8593 @ 20 °C/4 °C0.86 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.70.8593 @ 20°C0.860 g/mL at 20 °C(lit.) |
| Flavoring agents | EU Flavoring substances |
| Color/Form | COLORLESS, CLEAR LIQUIDColorless solid. |
| Solubility | 33 % (NIOSH, 2024)MISCIBLE WITH ALCOHOL, ETHER, OILSSOL IN 3 PARTS WATERSOL IN ALL ACETONE, AND BENZENEWater solubility: 330,000 mg/lSolubility in water, g/100ml at 20 °C: 28.5 (good)33%32.3 g/100 mL (16°C)32.3 g/100 mL (16 ºC) |
| Flash point | 0 °F (USCG, 1999)-32 °C-26 °F (-32 °C) (OPEN CUP)-31 °C c.c.-26 °F (open cup)(oc) -26 °F-18 °C |
| Boiling point | 108 °F at 760 mmHg (USCG, 1999)41.6 °C @ 760 MM HG42 °C111 °F42 °C @760 [mm Hg]41-43 °C |
| Melting point | -105 °C |
| Vapor density | 2.6 (vs air) |
| Vapor pressure | 6.38 psi ( 20 °C) |
| Refractive index | n20/D 1.354 |
| FLAVIS Number | 06.074 | Dimethoxymethane |
| Storage conditions | Store at <= 20°C. |
| Physical state | Liquid |
| pKa (acidity coefficient) | 3.1[at 20 ℃] |
| Color | Clear colorless |
| pH | pH (12.5vol % , 25℃) : 4.5～6.6 |
| Viscosity | 0.371mm2/s |
| Explosive limits | 1.6-17.6%(V) |
| Specific heat capacity | Cp(liquid): 2.13 J/(g·K), at 25℃ |
| Sensitivity | Moisture Sensitive |
| Merck | 14,6012 |
| BRN | 1697025 |
| Henry's law constant | (x 10-4 atmm3/mol): 1.73 at 25 °C (Hine and Mookerjee, 1975) |
| Exposure limits | ACGIH:TLV-TWA 1000 ppm (3110 mg/m3)OSHA:PEL-TWA 1000 ppm (3100 mg/m3)NIOSH:REL-TWA 1000 ppm |
| 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. |
| Cosmetics Ingredients Functions | SOLVENT |
| InChI | 1S/C3H8O2/c1-4-3-5-2/h3H2,1-2H3 |
| InChIKey | NKDDWNXOKDWJAK-UHFFFAOYSA-N |
| SMILES | COCOC |
| LogP (partition coefficient) | 0 |
| CAS DataBase Reference | 109-87-5(CAS DataBase Reference) |
| EWG's Food Scores | 2 |
| FDA UNII | 7H1M4G2NUE |
| NIST Chemistry Reference | Methane, dimethoxy-(109-87-5) |
| EPA Substance Registry System | Dimethoxymethane (109-87-5) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS02,GHS07 |
| Signal word | Danger |
| GHS hazard statements | H315-H319-H335-H336-H225 |
| GHS precautionary statements | P501-P240-P261-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P304+P340+P312-P403+P233-P403+P235-P405 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves |
| Hazard symbols | F,Xi |
| Risk statements (R) | 11-19-36-36/37/38 |
| Safety statements (S) | 16-26-33-7/9-37/39 |
| Occupational exposure band (OEB) | A |
| Occupational exposure limit (OEL) | TWA: 1000 ppm (3100 mg/m3) |
| UN transport number | UN 1234 |
| Water hazard class (WGK) | 1 |
| RTECS number | PA8750000 |
| F | 21 |
| Autoignition temperature | 459 °F |
| TSCA inventory status | TSCA listed |
| Customs code | 2911 00 00 |
| Hazard class | 3Flam. Liq. 2 |
| Packing group | II |
| Storage class | 3 - Flammable liquids |
| Hazardous substances data | 109-87-5(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 6653 mg/kg |
| Immediately dangerous to life or health concentration | 2,200 ppm [10% LEL] |
| REACH registrations | Active |
| Limited quantities | 1.0 L (0.3 gallon) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 1.2% (5 of 433) of reports.DangerH225 (98.8%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 433 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: Methane, dimethoxy-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Methane, dimethoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methane, dimethoxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 27-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/5159Methane, dimethoxy-: HSNO Approval: HSR001047 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT label | Flammable Liquid |
| Fire hazards | FLAMMABLE. Irritating gases may be produced when heated. Containers may explode in fire. Flashback along vapor trail may occur. Vapor may explode if ignited in an enclosed area. Irritating formaldehyde gas may be present in smoke. (USCG, 1999)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Highly flammable. Heating will cause rise in pressure with risk of bursting. Vapour/air mixtures are explosive. Risk of fire and explosion on contact with strong oxidizing agents or strong bases. |
| Fire potential | DANGEROUS, WHEN EXPOSED TO HEAT, FLAME, OXIDIZERS |
| Health hazards | VAPOR: Irritating to eyes, nose and throat. Harmful if inhaled. LIQUID: Irritating to skin and eyes. Harmful if swallowed. (USCG, 1999)· Inhalation or contact with material may irritate or burn skin and eyes. |
| Hazards summary | Animal inhalation studies: anesthesia and damage to the liver and other organs[ACGIH] A skin, eye, and respiratory tract irritantInhalation of high concentrations can cause CNS depression[ICSC] |
| DOT ID and guide | 1234 127 |
| Reactive group | Acetals, Ketals, Hemiacetals, and Hemiketals |
| UN classification | UN Hazard Class: 3UN Pack Group: II |
| TSCA requirements | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Methane, dimethoxy- is included on this list. |
| Reactivity Alerts | Highly Flammable |
| OSHA Standards | 8 hr Time-Weighted avg: 1,000 ppm (3,100 mg/cu m) |
| Fire fighting | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:Use water spray, dry powder, carbon dioxide, alcohol-resistant foam. In case of fire: keep drums, etc., cool by spraying with water. |
| First aid measures | Fresh air, rest. Refer for medical attention.First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Do NOT induce vomiting. Refer for medical attention . |
| Accidental release measures | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| First aid | Excerpt from NIOSH Pocket Guide for Methylal:General First Aid:(General first aid procedures) |
| Safe 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. |
| Exposure control and personal protection | · Wear positive pressure self-contained breathing apparatus (SCBA).500.0 [ppm] |
| Fire fighting procedures | TO FIGHT FIRE: FOAM, CARBON DIOXIDE, DRY CHEMICAL ...Water may be ineffective. Alcohol foam. |
| Cleanup methods | 1. REMOVE ALL IGNITION SOURCES. 2. VENTILATE AREA OF SPILL OR LEAK. 3. FOR SMALL QUANTITIES, ABSORB ON PAPER TOWELS. EVAPORATE IN SAFE PLACE (SUCH AS FUME HOOD). ALLOW SUFFICIENT TIME TO COMPLETELY CLEAR HOOD DUCTWORK. BURN PAPER IN SUITABLE LOCATION AWAY FROM COMBUSTIBLE MATERIALS. 3. LARGE QUANTITIES CAN BE COLLECTED, DISSOLVED IN ALC OF GREATER MOLECULAR WT THAN BUTYL ALC, & ATOMIZED IN SUITABLE COMBUSTION CHAMBER. METHYLAL SHOULD NOT BE ALLOWED TO ENTER CONFINED SPACE, SUCH AS SEWER, BECAUSE OF THE POSSIBILITY OF AN EXPLOSION. |
| Nonfire spill response | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: |
| Disposal methods | ... MAY BE DISPOSED OF BY DISSOLVING IN ALCOHOL OF GREATER MOLECULAR WEIGHT THAN BUTYL ALCOHOL & ATOMIZING IN SUITABLE COMBUSTION CHAMBER. |
| Spillage disposal | Consult an expert! Personal protection: filter respirator for organic vapours of low boiling point adapted to the airborne concentration of the substance. Remove all ignition sources. Cover the spilled material with sand or other non-combustible material. Collect leaking liquid in covered containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Preventive Measures | SRP: The scientific literature supports the wearing of contact lenses in industrial environments, as part of a program to protect the eye against chemical compounds and minerals causing eye irritation. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases contact lenses should not be worn.SAFE-HANDLING PRECAUTIONS SHOULD INCL USE OF ADEQUATE VENTILATION TO BE CERTAIN THAT AVG CONCN ARE WELL BELOW 1000 PPM, & AVOIDANCE OF EXCESSIVE OR PROLONGED SKIN CONTACT. METHYLAL SHOULD BE HANDLED WITH DUE REGARD FOR ITS FLAMMABLE PROPERTIES.To prevent injury from occurring as a result of contact with an aldehyde in the form of liquid or vapor, the process in which the substance is present should, if possible be conducted in enclosed plant. If openings are necessary for the purposes of manipulation, vapor should be prevented from escaping into the workroom by the application of exhaust ventilation to the plant or enclosure. When the process cannot be enclosed, exhaust ventilation hoods should be fitted to trap and extract escaping vapor before it can diffuse into the workroom atmosphere. /Aldehydes and ketals/The worker should immediately wash the skin when it becomes contaminated.Work clothing that becomes wet should be immediately removed due to its flammability hazard. |
| Body burden | In the EPA National Human Adipose Survey for fiscal year 1982, 46 composite samples categorized broadly by region and age group were analyzed for pollutants(1). Methylal was identified in one sample from the northeast US in the >45 age group. |
| Target organs | Eyes, skin, respiratory system, central nervous system |
| Environmental fate | TERRESTRIAL FATE: If released on land, methylal would volatilize rapidly due to its high vapor pressure and Henry's Law constant and low adsorptivity to soil. It would also exhibit high mobility in soil. The importance of biodegradation in soil is unknown. (SRC)AQUATIC FATE: If released to water, methylal will be primarily lost through volatilization. Its half-life in a model river is estimated from a calculated Henry's Law constant to be 7.2 hr(1-3). Adsorption to sediment and particulate matter in the water column, and bioconcentration should not be important. The importance of biodegradation in water is unknown. Hydrolysis is fairly slow(SRC).ATMOSPHERIC FATE: The atmosphere is the sink for methylal. In the atmosphere, methylal will degrade by reaction with photochemically-produced hydroxyl radicals. The half-life for this reaction is estimated to be 2.3 days(1). Methylal is highly soluble in water, 2.44X10+5 ppm(2), and would be washed out by rain. However, methylal thus remove would be recycled back into the atmosphere. (SRC) |
| Adverse effects | Neurotoxin - Acute solvent syndrome |
| Exposure routes | The substance can be absorbed into the body by inhalation of its vapour.inhalation, ingestion, skin and/or eye contact |
| Signs and Symptoms | Cough. Dizziness. Drowsiness. Headache. Sore throat. Unconsciousness.Dry skin.Redness. Pain.Abdominal pain. Nausea. Vomiting. Further see Inhalation.irritation eyes, skin, upper respiratory systemanesthesia |
| Effluent Concentrations | In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, methylal was identified in discharges of the following industrial category (positive occurrencesmedian concn in ppb): leather tanning (11637.5), plastics and synthetics (330.8), organic chemicals (645.6), publicly owned treatment works (35.0)(1). The highest effluent concn was 1637 ppb in the leather tanning industry(1). Detected in effluent concentrates from the advanced treatment plant in Orange County, CA, but not in that of five other communities(2). |
| ICSC Environmental Data | Environmental effects of the substance have been adequately investigated, but no significant effects have been found. |
| Soil Adsorption/Mobility | The Koc for methylal estimated from its water solubility, 2.44X10+5 ppm(1), by a recommended regression equation is 5(2). Therefore methylal would be very mobile in soil(3). |
| Human Toxicity Excerpts | ... PROPERTIES OF SIMPLE UNSUBSTITUTED ACETALS ARE CHARACTERIZED BY ETHER-LIKE ANESTHETIC ACTION, & BY RELATIVELY LOW DEGREE OF PRIMARY IRRITATION COMPARED TO PARENT ALDEHYDE. /ACETALS/INHALATION CAUSES IRRITATION OF RESP SYSTEM & DEPRESSION OF CNS. LIQ CAUSES IRRITATION OF EYES & WILL IRRITATE SKIN IF ALLOWED TO REMAIN. |
| Artificial Pollution Sources | Methylal used as a solvent and reagent in organic synthesis(2) may be released to the environment in waste water and as fugitive emissions relating to its manufacture and use. Mean vapor emission rates of methylal measured at two locations at an industrial waste water treatment facility in December were 28.6 and 14.7 mg/min sq-m, at which time the ambient and liquid surface temperatures were 6 and 15 °C, respectively(1).METHYLAL WAS ONE OF THE COMPONENTS IN WASTE WATER FROM A UREA-FORMALDEHYDE GLUE PLANT. |
| Environmental Biodegradation | A reduction in BOD in 8 hr was obtained in one study in which well acclimated sewage seed was incubated with 333 ppm of methylal(1). However this reduction was small compared with the theoretical oxygen demand and toxicity resulted in an initial increase in BOD. |
| F | 21 |
| Occupational exposure band (OEB) | A |
| Occupational exposure limit (OEL) | TWA: 1000 ppm (3100 mg/m3) |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves |
| Water hazard class (WGK) | 1 |
| Immediately dangerous to life or health concentration | 2,200 ppm [10% LEL] |
| TSCA inventory status | TSCA listed |
| RTECS number | PA8750000 |
| UN transport number | UN 1234 |
| Customs code | 2911 00 00 |
| Toxicity | LD50 orally in Rabbit: 6653 mg/kg |
| Risk statements (R) | 11-19-36-36/37/38 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS07 |
| Hazard symbols | F,Xi |
| Safety statements (S) | 16-26-33-7/9-37/39 |
| Hazard class | 3Flam. Liq. 2 |
| Storage class | 3 - Flammable liquids |
| Packing group | II |
| GHS hazard statements | H315-H319-H335-H336-H225 |
| Limited quantities | 1.0 L (0.3 gallon) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| Autoignition temperature | 459 °F |
| GHS precautionary statements | P501-P240-P261-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P304+P340+P312-P403+P233-P403+P235-P405 |
| Hazardous substances data | 109-87-5(Hazardous Substances Data) |
Applications & Uses
Description
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%.
Uses
Dimethoxymethane (Methylal) is a valuable extraction solvent for pharmaceutical products and a stable, inexpensive solvent for Grignard reactions. Methylal is stable under alkaline and mild acidic conditions. Its 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.
General Description
Dimethoxymethane (DMM, methylal) is a biodegradable dimethyl acetal. It can be synthesized by acid catalyzed condensation of formaldehyde with methanol. It is amphiphilic in nature with low viscosity, surface tension and boiling point. It is a flammable, highly volatile solvent with good dissolving power. DMM 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. Its thermal diffusivity has been determined by photoacoustic method. Analysis of the molecular structure of DMM by electron diffraction technique shows that it has C2 symmetry with a gauche-gauche conformation.
Preparation & Synthesis
Preparation
Dimethoxymethane synthesis is based on the liquid-phase acetalization reaction of methanol and formaldehyde. It can be manufactured by oxidation of methanol or by the reaction of formaldehyde with methanol. In aqueous acid, it is hydrolyzed back to formaldehyde and methanol. Reaction mechanisms and catalysis in the one-step synthesis of methylal via methanol oxidationNovel Porous Iron Molybdate Catalysts for Synthesis of Dimethoxymethane from Methanol: Metal Organic Frameworks as Precursors