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4-Methyl-1,3-dioxolan-2-one is an organic compound with the formula C4H6O3.
4-Methyl-1,3-dioxolan-2-one is a cyclic carbonate ester derived from propylene glycol.
4-Methyl-1,3-dioxolan-2-one colorless and odorless liquid is useful as a polar, aprotic solvent.
4-Methyl-1,3-dioxolan-2-one is chiral, but is used as the racemic mixture in most contexts.
CAS Number: 108-32-7
EC Number: 203-572-1
IUPAC Name: 4-Methyl-1,3-dioxolan-2-one
Chemical Formula: C4H6O3
Other names: (propán-1,2-diyl)-karbonát (sk), 4-metil-1,3-diossolan-2-one (it), 4-metylo-1,3-dioksolan-2-on (pl), carbonate de propylène (fr), carbonato de propileno (es), carbonato de propileno (pt), carbonato di propilene (it), propilen carbonat (ro), propilen karbonat (hr), propilen karbonat (sl), propilenkarbonatas (lt), propilén-karbonát (hu), propilēnkarbonāts (lv), propyleencarbonaat (nl), Propyleenikarbonaatti (fi), propylencarbonat (da), Propylencarbonat (de), propylenkarbonat (no), propylenkarbonat (sv), propylenkarbonát (cs), Propüleenkarbonaat (et), węglan glikolu propylenowego (pl), węglan propano-1,2-diylu (pl), ανθρακικό προπυλένιο (el), пропилен карбонат (bg), 1,3-Dioxolan-2-one, 4-methyl-, (4R)-4-methyl-1,3-dioxolan-2-one, 1,2-Propanediol cyclic carbonate, 1,2-Propylencarbonat, 1,3-Dioxolan-2-one, 4-methyl-, 1,3-dioxolan-2-one, 4-methyl-, 2-(carboxyoxy)-1-methylethyl carbonate, 4-methyl-1, 3-dioxolan-2-one, 4-Methyl-1,3-Dioxolan-2-One, 4-Methyl-1,3-dioxolan-2-one, 4-methyl-1,3-dioxolan-2-one, propylen carbonate, Propylencarbonat, Propylencarbonate, PROPYLENE CARBONATE, Propylene Carbonate, Propylene carbonate, propylene carbonate, Propylene Carbonate, Propylene carbonate, propylene carbonate, Propylene carbonate , 1,2-Propanediol carbonate, 1,2-Propanediol cyclic carbonate, 1,2-Propylene carbonate, 1,3-Dioxolan-2-one, 4-methyl- (9CI), 1-Methylethylene carbonate, 4-Methyl-1,3-dioxolan-2-one, 4-Methyl-2-oxo-1,3-dioxolane, Cyclic 1,2-propylene carbonate, Cyclic methylethylene carbonate, Cyclic propylene carbonate, Registration dossier, PC, Propylencarbonat, PROPYLENE CARBONATE, Propylene Carbonate, Propylene carbonate, Propylene glycol cyclic carbonate, 104083-03-6, 104083-03-6, 108-32-7, 127128-76-1, 127128-76-1, 30141-77-6, 30141-77-6, 607-194-00-1, PROPYLENE CARBONATE, 108-32-7, 4-Methyl-1,3-dioxolan-2-one, 1,2-Propylene carbonate, 1,2-Propanediol cyclic carbonate, Cyclic propylene carbonate, Texacar PC, 1,3-Dioxolan-2-one, 4-methyl-, Arconate 5000, 1,2-Propanediol carbonate, 1-Methylethylene carbonate, Cyclic 1,2-propylene carbonate, Dipropylene carbonate, 1,2-Propanediyl carbonate, 4-Methyldioxalone-2, Propylene glycol cyclic carbonate, Cyclic methylethylene carbonate, 4-Methyl-2-oxo-1,3-dioxolane, Carbonic acid, propylene ester, Propylenecarbonate, 99%, Carbonic acid, cyclic propylene ester, NSC 11784, Propylenester kyseliny uhlicite, Carbonic acid cyclic methylethylene ester, NSC-11784, Propylene carbonate [NF], 8D08K3S51E, Propylene carbonate (NF), WLN: T5OVOTJ D, 110320-40-6, CAS-108-32-7, HSDB 6806, PC-HP, EINECS 203-572-1, Carbonic acid, cyclic propylene ether, 4-methyl-1,3-dioxolane-2-one, Propylenester kyseliny uhlicite [Czech], BRN 0107913, butylhexanoate, UNII-8D08K3S51E, AI3-19724, MFCD00798264, MFCD00798265, Solvenon PC, propylen carbonate, MFCD00005385, Carbonic acid propylene, Arconate propylene carbonate, EC 203-572-1, SCHEMBL15309, 5-19-04-00021 (Beilstein Handbook Reference), 1-propanediol cyclic carbonate, (S)-1,2-Propanediol carbonate, CHEMBL1733973, DTXSID2026789, PROPYLENE CARBONATE [II], 2-Oxo-4-methyl-1,3-dioxolane, 1,2-PDC, 4-methyl-[1,3]dioxolan-2-one, NSC1913, PROPYLENE CARBONATE [HSDB], PROPYLENE CARBONATE [INCI], PROPYLENE CARBONATE [VANDF], NSC-1913, NSC11784, Propylene carbonate (Battery grade), PROPYLENE CARBONATE [MART.], Tox21_202047, Tox21_303214, BBL027518, PROPYLENE CARBONATE [USP-RS], STL373011, AKOS009158417, Propylene Carbonate (Industrial Grade), SB66353, Propylene carbonate, anhydrous, 99.7%, NCGC00165974-01, NCGC00165974-02, NCGC00256995-01, NCGC00259596-01, Propylene carbonate, for HPLC, 99.7%, BP-30108, BP-31155, SY008770, SY066861, DB-018081, Propylene carbonate, ReagentPlus(R), 99%, CS-0076373, FT-0602265, FT-0639979, FT-0660009, FT-0674103, P0525, D05633, EN300-296359, Propylene carbonate, anhydrous, Water 50ppm Max., Propylene carbonate, Selectophore(TM), >=99.0%, Q415979, J-002116, Propylene carbonate, Vetec(TM) reagent grade, 98%, F0001-0165, Propylene carbonate, >=99%, acid <10 ppm, H2O <10 ppm, 1,2-Propanediol cyclic carbonate, 4-Methyl-1,3-dioxolan-2-one, Propylene carbonate, United States Pharmacopeia (USP) Reference Standard, 1, 3-Dioxolan-2-one, 4-methyl- [ACD/Index Name], 1,2-Propanediol cyclic carbonate, 1,3-Dioxolan-2-one, 4-methyl- [ACD/Index Name], 108-32-7 [RN], 4-Methyl-1,3-dioxol-2-one [ACD/IUPAC Name], 4-Methyl-1,3-dioxolan-2-on [German] [ACD/IUPAC Name], 4-Methyl-1,3-dioxolan-2-one [ACD/IUPAC Name], 4-Méthyl-1,3-dioxolan-2-one [French] [ACD/IUPAC Name], 4-Methyl-2-oxo-1,3-dioxolane, Arconate 1000 [Trade name], Carbonic acid cyclic 1,2-propylene ester, Carbonic acid, cyclic propylene ether, Cyclic propylene carbonate, Jeffsol PC [Trade name], PC, PC-HP, Propylene carbonate [Wiki], Propylene glycol cyclic carbonate, T5OVOTJ D1 [WLN], [108-32-7] [RN], 1,2-PDC, 1,2-Propanediyl carbonate, 1,2-Propylene glycol carbonate, 1-Methylethylene carbonate, 2-Oxo-4-methyl-1,3-dioxolane, 8D08K3S51E, Arconate 5000 [Trade name], Arconate propylene carbonate, Carbonic acid cyclic methylethylene ester, Carbonic acid, cyclic propylene ester, Carbonic acid, propylene ester, Cyclic methylethylene carbonate, Dipropylene carbonate, FF9650000 [RTECS], MFCD00005385 [MDL number], MFCD00798264 [MDL number], MFCD00798265 [MDL number], Propylenester kyseliny uhlicite [Czech], Propylenester kyseliny uhlicite, Solvenon PC [Trade name], Texacar PC [Trade name], UNII-8D08K3S51E
Preparation of 4-Methyl-1,3-dioxolan-2-one
Although many organic carbonates are produced using phosgene, propylene and ethylene carbonates are exceptions.
They are mainly prepared by the carbonation of the epoxides (epoxypropane, or propylene oxide here):
CH3CHCH2O + CO2 → CH3C2H3O2CO
The process is particularly attractive since the production of these epoxides consumes carbon dioxide.
Thus this reaction is a good example of a green process.
The corresponding reaction of 1,2-propanediol with phosgene is complex, yielding not only 4-Methyl-1,3-dioxolan-2-one but also oligomeric products.
4-Methyl-1,3-dioxolan-2-one can also be synthesized from urea and propylene glycol over zinc acetate.
Applications of 4-Methyl-1,3-dioxolan-2-one
As a solvent
4-Methyl-1,3-dioxolan-2-one is used as a polar, aprotic solvent.
4-Methyl-1,3-dioxolan-2-one has a high molecular dipole moment (4.9 D), considerably higher than those of acetone (2.91 D) and ethyl acetate (1.78 D).
4-Methyl-1,3-dioxolan-2-one is possible, for example, to obtain potassium, sodium, and other alkali metals by electrolysis of their chlorides and other salts dissolved in 4-Methyl-1,3-dioxolan-2-one.
Electrolyte
Due to its high relative permittivity (dielectric constant) of 64, it is frequently used as a high-permittivity component of electrolytes in lithium batteries, usually together with a low-viscosity solvent (e.g. dimethoxyethane).
Its high polarity allows it to create an effective solvation shell around lithium ions, thereby creating a conductive electrolyte.
However, 4-Methyl-1,3-dioxolan-2-one is not used in lithium-ion batteries due to its destructive effect on graphite.
4-Methyl-1,3-dioxolan-2-one can also be found in some adhesives, paint strippers, and in cosmetics.
4-Methyl-1,3-dioxolan-2-one is also used as plasticizer.
4-Methyl-1,3-dioxolan-2-one is also used as a solvent for removal of CO2 from natural gas and synthesis gas where H2S is not also present.
This use was developed by El Paso Natural Gas Company and Fluor Corporation in the 1950s for use at the Terrell County Gas Plant in West Texas, now owned by Occidental Petroleum.
Other
4-Methyl-1,3-dioxolan-2-one product may be converted to other carbonate esters by transesterification as well.
In electrospray ionization mass spectrometry, 4-Methyl-1,3-dioxolan-2-one is doped into low surface tension solutions to increase analyte charging.
In Grignard reaction 4-Methyl-1,3-dioxolan-2-one (or most other carbonate esters) might be used to create tertiary alcohols.
Use and Manufacturing of 4-Methyl-1,3-dioxolan-2-one
Used for carbon dioxide recovery and solvent extraction; Also used in lithium batteries, as a plasticizer, in natural gas purification, and as a synthetic fiber spinning solvent; Used as a solvent in surface coatings, paint removers, cosmetics, personal care products, cleaners, degreasers, dyes, fibers, plastics, wood-binder resins, and photochromic solutions; Also used as a solvent to bake enamels, a reactive diluent for urethanes and epoxy resins, a dispersant for lubricants and greases, a binder for foundry sand and moulds, a cleaner in electronics, and as a water scavenger
Industry Uses of 4-Methyl-1,3-dioxolan-2-one
Cleaning agent
Conductive agent
Functional fluids (closed systems)
Intermediates
Lubricants and lubricant additives
Monomers
Not Known or Reasonably Ascertainable
Other
Paint additives and coating additives not described by other categories
Polymerization promoter
Process regulators
Solvent
Solvents (which become part of product formulation or mixture)
Viscosity adjustors
Consumer Uses of 4-Methyl-1,3-dioxolan-2-one
Conductive agent
Lubricants and lubricant additives
Monomers
Not Known or Reasonably Ascertainable
Other
Paint additives and coating additives not described by other categories
Process regulators
Solvent
Solvents (which become part of product formulation or mixture)
Viscosity adjustors
Household Products of 4-Methyl-1,3-dioxolan-2-one
Household & Commercial/Institutional Products
Information on 120 consumer products that contain 4-Methyl-1,3-dioxolan-2-one in the following categories is provided:
Commercial / Institutional
Home Maintenance
Inside the Home
Personal Care
Pet Care
General Manufacturing Information
Industry Processing Sectors
Adhesive Manufacturing
All Other Basic Inorganic Chemical Manufacturing
All Other Basic Organic Chemical Manufacturing
All Other Chemical Product and Preparation Manufacturing
Asphalt Paving, Roofing, and Coating Materials Manufacturing
Computer and Electronic Product Manufacturing
Electrical Equipment, Appliance, and Component Manufacturing
Fabricated Metal Product Manufacturing
Machinery Manufacturing
Miscellaneous Manufacturing
Not Known or Reasonably Ascertainable
Paint and Coating Manufacturing
Plastics Material and Resin Manufacturing
Transportation Equipment Manufacturing
Wholesale and Retail Trade
4-Methyl-1,3-dioxolan-2-one can be synthesized from propylene oxide and CO2.
Optically active form of 4-Methyl-1,3-dioxolan-2-one can be prepared from the reaction between CO2 and racemic epoxides.
Decomposition of 4-Methyl-1,3-dioxolan-2-one on the graphite electrode in lithium batteries results in the formation of a lithium intercalated compound.
4-Methyl-1,3-dioxolan-2-one is a cyclic carbonate that is commonly used as a solvent and as a reactive intermediate in organic synthesis.
4-Methyl-1,3-dioxolan-2-one is being considered as a potential electrochemical solvent due to its low vapor pressure, high dielectric constant and high chemical stability.
4-Methyl-1,3-dioxolan-2-one is a polar aprotic solvent used as a “green” sustainable alternative solvent for chemical transformations.
4-Methyl-1,3-dioxolan-2-one is a low toxicity, biodegradable, non-corrosive colorless liquid with a high boiling point, low vapor pressure, and EPA VOC exemption.
Due to its low vapor pressure and findings of negligible photochemical reactivity, 4-Methyl-1,3-dioxolan-2-one is an effective substitute for more hazardous solvents such a MEK, methylene chloride, toluene, acetone, NMP, and perchloroethylene.
4-Methyl-1,3-dioxolan-2-one is also compatible with other solvents providing an efficient ingredient in co-solvent formulations.
4-Methyl-1,3-dioxolan-2-one is widely used in the manufacture of paints, adhesives, coatings, surface cleaners, degreasers, strippers, and inks formulations as well as in lithium-ion batteries, as electrolytic solvent, and in the removal of carbon dioxide from natural gas.
4-Methyl-1,3-dioxolan-2-one is a polymer that belongs to the class of polycarbonates.
4-Methyl-1,3-dioxolan-2-one is synthesized by the reaction of 4-Methyl-1,3-dioxolan-2-one with chlorine atoms.
The morphology, or shape, of this polymer can be changed by changing the amount of chlorine atoms used in the synthesis.
4-Methyl-1,3-dioxolan-2-one has a high degree of crystallinity and these crystals are composed mainly of hydrogen bonds.
This polymer also has a high degree of viscosity and melting point, which decreases with increasing chlorine atom content.
4-Methyl-1,3-dioxolan-2-one has a low solubility in water and does not dissolve in common organic solvents.
Chemical Properties of 4-Methyl-1,3-dioxolan-2-one
4-Methyl-1,3-dioxolan-2-one is soluble in water and miscible with most organic solvents.
4-Methyl-1,3-dioxolan-2-one is found to be an excellent low-boiling solvent for cellulose acetate, nitrocellulose, adhesive compositions and vinyl chloride-acetate resins.
4-Methyl-1,3-dioxolan-2-one is also a solvent for hydrocarbons, gums and shellac.
Some of its uses are as a solvent and stabilizer in DDT aerosol-type insecticides, and as a fumigant and food preservative.
Since it is an acid acceptor, 4-Methyl-1,3-dioxolan-2-one is also used as a stabilizer for vinyl chloride resins and other chlorinated systems.
Hazard classification & labelling of 4-Methyl-1,3-dioxolan-2-one
Warning! According to the harmonised classification and labelling (CLP00) approved by the European Union, this substance causes serious eye irritation.
About 4-Methyl-1,3-dioxolan-2-one
4-Methyl-1,3-dioxolan-2-one is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to < 100 000 tonnes per annum.
4-Methyl-1,3-dioxolan-2-one is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses of 4-Methyl-1,3-dioxolan-2-one
4-Methyl-1,3-dioxolan-2-one is used in the following products: coating products, plant protection products, cosmetics and personal care products and perfumes and fragrances.
Other release to the environment of 4-Methyl-1,3-dioxolan-2-one is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
Article service life of 4-Methyl-1,3-dioxolan-2-one
Release to the environment of 4-Methyl-1,3-dioxolan-2-one can occur from industrial use: industrial abrasion processing with low release rate (e.g. cutting of textile, cutting, machining or grinding of metal) and of articles where the substances are not intended to be released and where the conditions of use do not promote release.
Other release to the environment of 4-Methyl-1,3-dioxolan-2-one is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials), indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment) and outdoor use in long-life materials with high release rate (e.g. tyres, treated wooden products, treated textile and fabric, brake pads in trucks or cars, sanding of buildings (bridges, facades) or vehicles (ships)).
4-Methyl-1,3-dioxolan-2-one can be found in complex articles, with no release intended: electrical batteries and accumulators.
4-Methyl-1,3-dioxolan-2-one can be found in products with material based on: plastic (e.g. food packaging and storage, toys, mobile phones), plastic used for packaging (excluding food packaging) and plastic used for articles intended for food contact (e.g. plastic dinner ware, food storage).
Widespread uses by professional workers of 4-Methyl-1,3-dioxolan-2-one
4-Methyl-1,3-dioxolan-2-one is used in the following products: lubricants and greases, washing & cleaning products, plant protection products, polymers and coating products.
4-Methyl-1,3-dioxolan-2-one is used in the following areas: health services and scientific research and development.
Other release to the environment of 4-Methyl-1,3-dioxolan-2-one is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use, outdoor use in close systems with minimal release (e.g. hydraulic liquids in automotive suspension, lubricants in motor oil and break fluids) and indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters).
Formulation or re-packing of 4-Methyl-1,3-dioxolan-2-one
4-Methyl-1,3-dioxolan-2-one is used in the following products: coating products, inks and toners, fillers, putties, plasters, modelling clay and metal surface treatment products.
Release to the environment of 4-Methyl-1,3-dioxolan-2-one can occur from industrial use: formulation of mixtures and formulation in materials.
Uses at industrial sites of 4-Methyl-1,3-dioxolan-2-one
4-Methyl-1,3-dioxolan-2-one is used in the following products: coating products, lubricants and greases, washing & cleaning products, polymers and cosmetics and personal care products.
4-Methyl-1,3-dioxolan-2-one is used in the following areas: health services and scientific research and development.
4-Methyl-1,3-dioxolan-2-one is used for the manufacture of: electrical, electronic and optical equipment, chemicals, plastic products and.
Release to the environment of 4-Methyl-1,3-dioxolan-2-one can occur from industrial use: in processing aids at industrial sites, in the production of articles, of substances in closed systems with minimal release, as processing aid, for thermoplastic manufacture and as an intermediate step in further manufacturing of another substance (use of intermediates).
Release to the environment of 4-Methyl-1,3-dioxolan-2-one can occur from industrial use: manufacturing of the substance.
