PROPYLENE CARBONATE
Synonyms: 1,2-Propanediol cyclic carbonate, 4-Methyl-1,3-dioxolan-2-one; CAS Number:108-32-7; Empirical Formula:C4H6O3; Molecular Weight:102.09 ; Beilstein/REAXYS Number:107913
EC Number:203-572-1; MDL number MFCD00005385; PubChem Substance ID:57648504
Other names: 4-Methyl-1,3-dioxolan-2-one; Propylene glycol carbonate; Carbonic acid propylene glycol ester ;1,3-Dioxolan-2-one, 4-methyl-; Carbonic acid, cyclic propylene ester; Cyclic methylethylene carbonate; Cyclic propylene carbonate; Cyclic 1,2-propylene carbonate; Propylene glycol cyclic carbonate; 1-Methylethylene carbonate; 1,2-Propanediol carbonate; 1,2-Propanediol cyclic carbonate; 1,2-Propanediyl carbonate; 1,2-Propylene carbonate; 4-Methyl-1,3-dioxolan-2-one; 1,2-Propylene glycol carbonate; 4-Methyl-1,3-dioxol-2-one; Dipropylene carbonate; 4-Methyldioxalone-2; 4-Methyl-2-oxo-1,3-dioxolane; 1,2-PDC; Propylenester kyseliny uhlicite; Arconate propylene carbonate; PC-HP; Solvenon PC; Texacar PC; Arconate 5000; Carbonic acid cyclic methylethylene ester; Carbonic acid, propylene ester; NSC 11784
Propylene carbonate (PC) is a polar aprotic substance with very similar physicochemical characteristics to the organic solvents traditionally used for organic synthesis, such as acetonitrile and acetone.
Therefore, PC is beginning to be used as a “green” sustainable alternative solvent for chemical transformations. PC is a low toxicity, non-corrosive colourless liquid with a high boiling point and low vapour pressure.
It is biodegradable and economical, allowing its large-scale use. PC can be prepared by a reaction between propylene epoxide and carbon dioxide with 100% atomic economy. The easy preparation of propylene epoxide and the use of an available, abundant, economical, and renewable source of carbon, such as CO2, make this process one of the best routes for the synthesis of PC.
Therefore, we present in this review numerous catalytic systems that have been studied to improve the efficiency of this reaction. Certain interesting examples of reactions using PC are found in the literature, of which we discuss asymmetric hydrogenation, hydrosilylation, asymmetric aldol reactions, the asymmetric synthesis of cyanohydrins, the synthesis of heterocyclic compounds, such as bisindole and tetrahydroquinoline, the hydroacylation of alkynes, α-hydrazination reactions, oxidations, the Sonogashira reaction, allylic alkylation and asymmetric amination, the Heck reaction, enzymatic kinetic resolution, and isomerisation-hydroformylation reactions.
Keywords: Propylene carbonate, carbonic acid diesters, green chemistry, green solvent, organic synthesis, environment.
Use: Propylene Carbonate (PC) is a VOC-free clear polar solvent having high boiling and flash points. Propylene Carbonate (PC) is a carbonate ester derived from propylene glycol with the peculiarity to have a low order of toxicity and a mild ether-like odor. Propylene Carbonate (PC) is stable under most conditions and it is not hydroscopic or corrosive. It is particularly well suited for applications requiring a water white product or high purity. It can be used in cosmetics and personal care products; mainly in the formulation of make-up, primarily lipstick, eye shadow, and mascara, as well as in skin cleansing products.
Use: Propylene carbonate is used in a variety of syntheses and applications as a polar, aprotic solvent. It can also be found in some adhesives, paint strippers, cosmetics, and can be used as a plasticizer.
Description
General description
Propylene carbonate can be synthesized from propylene oxide and CO2. Optically active form of propylene carbonate can be prepared from the reaction between CO2 and racemic epoxides.
Decomposition of propylene carbonate on the graphite electrode in lithium batteries results in the formation of a lithium intercalated compound.
Propylene carbonate is a cyclic carbonate that is commonly used as a solvent and as a reactive intermediate in organic synthesis.
It is being considered as a potential electrochemical solvent due to its low vapor pressure, high dielectric constant and high chemical stability.
Application
Propylene carbonate may be used as a solvent for the asymmetric hydrogenation of nonfunctionalized olefins.
Propylene carbonate (often abbreviated PC) is an organic compound with the formula C4H6O3. It is a cyclic carbonate ester derived from propylene glycol.
This colorless and odorless liquid is useful as a polar, aprotic solvent.
Propylene carbonate is chiral, but is used exclusively as the racemic mixture in most contexts.
Preparation
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 propylene carbonate but also oligomeric products.
Propylene carbonate can also be synthesized from urea and propylene glycol over zinc acetate.
Applications
As a solvent
Propylene carbonate is used as a polar, aprotic solvent. It has a high molecular dipole moment (4.9 D), considerably higher than those of acetone (2.91 D) and ethyl acetate (1.78 D).
It is possible, for example, to obtain potassium, sodium, and other alkali metals by electrolysis of their chlorides and other salts dissolved in propylene carbonate.
Due to its high 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, it is not used in lithium-ion batteries due to its destructive effect on graphite.
Propylene carbonate can also be found in some adhesives, paint strippers, and in cosmetics. It is also used as plasticizer.
Propylene carbonate 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
Propylene carbonate product may be converted to other carbonate esters by transesterification as well (see Carbonate ester#Carbonate transesterification).
In electrospray ionization mass spectrometry, propylene carbonate is doped into low surface tension solutions to increase analyte charging.
In Grignard reaction propylene carbonate (or most other carbonate esters) might be used to create tertiary alcohols.
IUPAC name: 4-Methyl-1,3-dioxolan-2-one
Other names: (R,S)-4-Methyl-1,3-dioxolan-2-one; Cyclic propylene carbonate; Carbonic acid propylene ester; Cyclic 1,2-propylene carbonate; Propylene glycol cyclic carbonate;1,2-Propanediol carbonate
;4-Methyl-2-oxo-1,3-dioxolane; Arconate 5000; Texacar PC
CAS Number: 108-32-7
Properties
Chemical formula: C4H6O3
Molar mass: 102.089 g·mol−1
Appearance: Colorless liquid
Density: 1.205 g/cm3
Melting point: −48.8 °C
Boiling point: 242 °C
Solubility in water: Very soluble (240 g/L at 20°C)
Refractive index (nD):1.4189
CAS number: 108-32-7
EC index number: 607-194-00-1
EC number: 203-572-1
Hill Formula: C₄H₆O₃
Molar Mass: 102.09 g/mol
HS Code: 2920 90 10
Physicochemical Information
Boiling point: 243 °C (1013 hPa)
Density: 1.20 g/cm3 (20 °C)
Explosion limit: 1.8 – 14.3 %(V)
Flash point: 123 °C
Ignition temperature: 435 °C
Melting Point: -49 °C
pH value: 7.0 (200 g/l, H₂O, 20 °C)
Vapor pressure: 0.04 hPa (20 °C)
Viscosity kinematic: 1.4 mm2/s (43 °C)
Solubility: 240 g/l
Toxicological Information
LD 50 oral: LD50 Rat > 5000 mg/kg
LD 50 dermal: LD50 Rabbit > 20000 mg/kg
INDUSTRIAL USES:
Adhesives and sealant chemicals
Component in Li-ion electrolyte
Intermediates
Ion exchange agents
Lubricants and lubricant additives
Paint
Paint additives and coating additives not described by other categories
Photosensitive chemicals
Plasticizers
Solvents (which become part of product formulation or mixture)
Methods of Manufacturing
The most important and versatile method for producing carbonates is the phosgenation of hydroxy compounds.
Over the past 20 years, the trend is to manufacture carbonates without the use of phosgene.
This method has the advantage of avoiding the use of highly toxic phosgene as well as considerably lower cost.
The catalytic insertion of CO2 with oxiranes directly provides the five-membered cyclic carbonate.
Oxiranes such as ethylene oxide and propylene oxide undergo insertion at ~150-175 °C under pressure with the aid of a quaternary ammonium salt catalyst to yield ethylene carbonate and propylene carbonate, respectively.
Propylene carbonate dipolar aprotic solvent is a next-generation, high performing solvent.
Propylene carbonate works well in a variety of different applications thanks to its excellent solvency power and water miscibility. It is a safer alternative to commonly used dipolar aprotic solvents like NMP (N-methylpyrrolidone), DMAc (dimethylacetamide), DMSO (dimethylsulfoxide), DMF (dimethylformamide), and acetonitrile, some of which face increasing regulatory pressure.
Key Benefits
Excellent performance in various applications
Excellent NMP and NEP replacement
Favorable safety, health, and environmental profile
Polyurethane dispersion (PUD) coating
Propylene carbonate is a high performance, safer cosolvent for water-based polyurethanes. Effective as both a solvent and coalescent for the PUD market,
Propylene carbonate can also be an effective NMP replacement. It can provide not only formulation flexibility but also a favorable safety, health, and environmental profile.
Propylene Carbonte is a high performance, safer cosolvent for water-based polyurethanes. Effective as both a solvent and coalescent for the PUD market
Cleaners and paint strippers
When employed in cleaners and paint strippers, Propylene Carbonate has demonstrated to be an effective NMP replacement.
The high solvency power can enhance performance of industrial cleaning formulations. Propylene Carbonate can be used for cleaning molds or tools related to polyurethane foam, polymer, polyester, or epoxy resins.
The lower volatility of Propylene Carbonate is beneficial for reduced worker and environmental exposure.
Pharmaceutical synthesis
Propylene carbonate can be considered for use as a medium to carry out various chemical reactions, such as the production of pharmaceuticals. In such applications, it can be a replacement for solvents like NMP, NEP, DMF, and DMAc.
Safety
Clinical studies indicate that propylene carbonate does not cause skin irritation or sensitization when used in cosmetic preparations, whereas moderate skin irritation is observed when used undiluted.
No significant toxic effects were observed in rats fed propylene carbonate, exposed to the vapor, or exposed to the undiluted liquid.
In the US, propylene carbonate is not regulated as a volatile organic compound (VOC) because it does not contribute significantly to the formation of smog and because its vapor is not known or suspected to cause cancer or other toxic effects.
PROPYLENE CARBONATE
108-32-7
4-Methyl-1,3-dioxolan-2-one
1,2-Propylene carbonate
1,2-Propanediol cyclic carbonate
1,3-Dioxolan-2-one, 4-methyl-
Cyclic propylene carbonate
Texacar PC
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
Carbonic acid, cyclic propylene ester
NSC 11784
Propylenester kyseliny uhlicite
Carbonic acid cyclic methylethylene ester
HSDB 6806
EINECS 203-572-1
Propylene carbonate [NF]
Carbonic acid, cyclic propylene ether
Propylenester kyseliny uhlicite [Czech]
BRN 0107913
AI3-19724
4-methyl-1,3-dioxolane-2-one
Propylene carbonate (NF)
Propylene carbonate, 99.5%
CAS-108-32-7
PC-HP
Propylene carbonate, 99.5%, anhydrous, AcroSeal(R)
Propylene carbonate [USAN]
Solvenon PC
propylen carbonate
MFCD00005385
Carbonic acid propylene
1, 3-Dioxolan-2-one, 4-methyl-
1,2-Propanediol cyclic carbonate
1,3-Dioxolan-2-one, 4-methyl- [ACD/Index Name]
107913
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
8D08K3S51E
Arconate 1000
Carbonic acid cyclic 1,2-propylene ester
Carbonic acid, cyclic propylene ether
Cyclic propylene carbonate
FF9650000
Jeffsol PC
MFCD00005385 [MDL number]
PC
PC-HP
Propylene carbonate [Wiki]
Propylene glycol cyclic carbonate
UNII:8D08K3S51E
(4S)-4-Methyl-1,3-dioxolan-2-one [ACD/IUPAC Name]
(R)-4-Methyl-1,3-dioxolan-2-one
(S)-4-Methyl-1,3-dioxolan-2-one
[108-32-7]
1,2-PDC
1,2-PROPANEDIOL CARBONATE
1,2-Propanediyl carbonate
1,2-PROPYLENE CARBONATE
1,2-Propylene glycol carbonate
1,2-Propylene-d6 Carbonate
1-Methylethylene carbonate
2-(Piperidin-4-yl)acetonitrile
202480-74-8 [RN]
2-Oxo-4-methyl-1,3-dioxolane
4-METHYL-1,3-DIOXOLANE-2-ONE
Arconate 5000
Arconate propylene carbonate
Carbonic acid cyclic methylethylene ester
Carbonic acid, cyclic propylene ester
Carbonic acid, propylene ester
CYCLIC 1,2-PROPYLENE CARBONATE
Cyclic methylethylene carbonate
Dipropylene carbonate
propylenecarbonate
Propylenester kyseliny uhlicite [Czech]
Propylenester kyseliny uhlicite
Solvenon PC
Texacar PC
WLN: T5OVOTJ D
OTHER LANGUAGES
(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)
CAS names
1,3-Dioxolan-2-one, 4-methyl-
Other
IUPAC names
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
Trade names
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
PC
Propylencarbonat
PROPYLENE CARBONATE
Propylene Carbonate
Propylene carbonate
Propylene glycol cyclic carbonate
Other identifiers: 104083-03-6
CAS number:104083-03-6
Deleted CAS number:108-32-7
CAS number: 127128-76-1
CAS number: 127128-76-1
Deleted CAS number:30141-77-6
CAS number:30141-77-6
Deleted CAS number:607-194-00-1
PROPYLENE CARBONATE CAS NO: 108-32-7
EINECS NO: 203-572-1
Propylene carbonate synonyms: 108-32-7; 4-Methyl-1,3-dioxolan-2-one; 1,2-Propylene carbonate; 1,2-Propanediol cyclic carbonate; 1,3-Dioxolan-2-one, 4-methyl-; Cyclic propylene carbonate; Texacar PC; 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; Carbonic acid, cyclic propylene ester; NSC 11784; Propylenester kyseliny uhlicite; Carbonic acid cyclic methylethylene ester; HSDB 6806; EINECS 203-572-1; Propylene carbonate [NF]; Carbonic acid, cyclic propylene ether; propylenester kyseliny uhlicite [Czech]; BRN 0107913; AI3-19724; 4-methyl-1,3-dioxolane-2-one; Propylene carbonate (NF); WLN: T5OVOTJ D; DSSTox_CID_6789; DSSTox_RID_78214; DSSTox_GSID_26789; Propylene carbonate, 99.5%; CAS-108-32-7; PC-HP; Propylene carbonate, 99.5%, anhydrous, AcroSeal(R); Propylene carbonate [USAN]; Solvenon PC; propylen carbonate; MFCD00005385; Carbonic acid propylene; ACMC-209dtm; ACMC-20aj2f; Arconate propylene carbonate; EC 203-572-1; ACMC-1C29L; SCHEMBL15309; 5-19-04-00021 (Beilstein Handbook Reference); KSC492E8H; CHEMBL1733973; DTXSID2026789; 2-Oxo-4-methyl-1,3-dioxolane; CTK3J2283; 1,2-PDC; 4-methyl-[1,3]dioxolan-2-one; NSC1913; NSC-1913; NSC11784; Tox21_202047; Tox21_303214; ANW-15928; BBL027518; MFCD00798265; NSC-11784; STL373011; AKOS009158417; MCULE-9055336051; Propylene Carbonate (Industrial Grade); VC30366; Propylene carbonate, anhydrous, 99.7%; NCGC00165974-01; NCGC00165974-02; NCGC00256995-01; NCGC00259596-01; Propylene carbonate, for HPLC, 99.7%; AK109386; AK688454; BP-30108; LS-51953; O433; SC-65189; SY008770; DB-018081; Propylene carbonate, ReagentPlus(R), 99%; CS-0076373; FT-0602265; FT-0639979; FT-0660009; FT-0674103; NS00004305; P0525; D05633; 23262-EP2269986A1; 23262-EP2274983A1; 23262-EP2284165A1; 23262-EP2292593A2; 23262-EP2295399A2; 23262-EP2308858A1; PROPYLENE CARBONATE;Cyclic propylene carbonate; Propylene carbonate, Selectophore(TM), >=99.0%; Propylene carbonate, Vetec(TM) reagent grade, 98%; F0001-0165; Propylene carbonate, >=99%, acid <10 ppm, H2O <10 ppm; Propylene carbonate, United States Pharmacopeia (USP) Reference Standard; carbonate de propylène; 1, 3-Dioxolan-2-one, 4-methyl-; 1,2-Propanediol cyclic carbonate; 1,3-Dioxolan-2-one, 4-methyl- [ACD/Index Name]; 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; 8D08K3S51; Arconate 1000; Carbonic acid cyclic 1,2-propylene ester; Carbonic acid, cyclic propylene ether; Cyclic propylene carbonate; FF9650000; Jeffsol PC; MFCD00005385 [MDL number]; PC; PC-HP; Propylene glycol cyclic carbonate; UNII:8D08K3S51E; (4S)-4-Methyl-1,3-dioxolan-2-one [ACD/IUPAC Name]; (R)-4-Methyl-1,3-dioxolan-2-one; (S)-4-Methyl-1,3-dioxolan-2-one; 1,2-PDC; 1,2-PROPANEDIOL CARBONATE; 1,2-Propanediyl carbonate; 1,2-PROPYLENE CARBONATE; 1,2-Propylene glycol carbonate; 1,2-Propylene-d6 Carbonate; 1-Methylethylene carbonate; 2-Oxo-4-methyl-1,3-dioxolane; 4-METHYL-1,3-DIOXOLANE-2-ONE; Arconate 5000; Arconate propylene carbonate; Carbonic acid cyclic methylethylene ester; Carbonic acid, cyclic propylene ester; Carbonic acid, propylene ester; CYCLIC 1,2-PROPYLENE CARBONATE; Cyclic methylethylene carbonate; Dipropylene carbonate; MFCD00798264 [MDL number]; MFCD00798265 [MDL number]; Propylene Carbonate (Industrial Grade); propylene carbonate [pc]; propylene carbonate 99%; propylene carbonate 99.5%; propylene carbonate, 99%; propylene carbonate, 99%,; propylene carbonate, 99.5%; propylene carbonate, 99.5%, anhydrous, acroseal??; propylene carbonate, reagent; propylene carbonate 99%, hydry, water 50 ppm (by k.f.); propylenecarbonate; Propylenester kyseliny uhlicite [Czech]; Propylenester kyseliny uhlicite; Solvenon PC; Texacar PC; WLN: T5OVOTJ D, propilen karbonat, propilen ester, propilenester, propandil karbonat, propilen glikol, 4-metil-1,4-dioksolan, diogzolan, diokzolan, arkonat 5000)
ChemSpider: 7636
ECHA InfoCard: 100.003.248
PubChem CID: 7924
UNII: 8D08K3S51E
CompTox Dashboard (EPA): DTXSID2026789
Chemical formula C4H6O3
Molar mass 102.089 g·mol-1
Appearance Colorless liquid
Density 1.205 g/cm3
Melting point -48.8 °C (-55.8 °F; 224.3 K)
Boiling point 242 °C (468 °F; 515 K)
Solubility in water Very soluble (240 g/L at 20°C)
Refractive index (nD) 1.4189
Although many organic carbonates are produced using phosgene, propylene and ethylene carbonates are exceptions. They are mainly prepared by the carbonation of the epoxides[4] (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 propylene carbonate but also oligomeric products.
Propylene carbonate can also be synthesized from urea and propylene glycol over zinc acetate.
Applications
As a solvent
Propylene carbonate is used as a polar, aprotic solvent. It has a high molecular dipole moment (4.9 D), considerably higher than those of acetone (2.91 D) and ethyl acetate (1.78 D). It is possible, for example, to obtain potassium, sodium, and other alkali metals by electrolysis of their chlorides and other salts dissolved in propylene carbonate.
Due to its high 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, it is not used in lithium-ion batteries due to its destructive effect on graphite
Propylene carbonate can also be found in some adhesives, paint strippers, and in cosmetics.[9] It is also used as plasticizer. Propylene carbonate 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
Propylene carbonate product may be converted to other carbonate esters by transesterification as well (see Carbonate ester#Carbonate transesterification).
In electrospray ionization mass spectrometry, propylene carbonate is doped into low surface tension solutions to increase analyte charging.
In Grignard reaction propylene carbonate (or most other carbonate ester) might be used to create tertiary alcohols.
Safety
Clinical studies indicate that propylene carbonate does not cause skin irritation or sensitization when used in cosmetic preparations, whereas moderate skin irritation is observed when used undiluted. No significant toxic effects were observed in rats fed propylene carbonate, exposed to the vapor, or exposed to the undiluted liquid. In the US, propylene carbonate is not regulated as a volatile organic compound (VOC) because it does not contribute significantly to the formation of smog and because its vapor is not known or suspected to cause cancer or other toxic effects.
Properties
Related Categories Alternative Energy, Anhydrous Solvents, Electrolytes, Lithium-Ion Batteries, Materials Science,
Organic Solvents, Solvent Bottles, Solvent Packaging Options, Solvent by Application, Solvents, Solvents & Additives, Sure/Seal Bottles
Less…
Quality Level 100
grade anhydrous
vapor pressure 0.13 mmHg ( 20 °C)
0.98 mmHg ( 50 °C)
assay 99.7%
autoignition temp. 851 °F
expl. lim. 14.3 %
impurities <0.002% water
<0.005% water (100 mL pkg)
refractive index n20/D 1.421 (lit.)
bp 240 °C (lit.)
mp -55 °C (lit.)
density 1.204 g/mL at 25 °C (lit.)
SMILES string CC1COC(=O)O1
InChI 1S/C4H6O3/c1-3-2-6-4(5)7-3/h3H,2H2,1H3
InChI key RUOJZAUFBMNUDX-UHFFFAOYSA-N
Propylene carbonate can be synthesized from propylene oxide and CO2. Optically active form of propylene carbonate can be prepared from the reaction between CO2 and racemic epoxides. Decomposition of propylene carbonate on the graphite electrode in lithium batteries results in the formation of a lithium intercalated compound.
Propylene carbonate is a cyclic carbonate that is commonly used as a solvent and as a reactive intermediate in organic synthesis. It is being considered as a potential electrochemical solvent due to its low vapor pressure, high dielectric constant and high chemical stability.
Application
Propylene carbonate may be used as a solvent for the asymmetric hydrogenation of nonfunctionalized olefins.
Propylene carbonate (PC) is a VOC-exempt* clear polar solvent having high boiling and
flash points, a low order of toxicity and a mild ether-like odor. It is stable under most
conditions and is not hydroscopic or corrosive. is particularly well suited for applications
requiring a water white product or high purity. Examples would be cosmetics, electronics
or where recycling of spent material will occur.
Product
Identification
Chemical Name Dioxolanone
Chemical Family Organic Carbonate
Other Names 3-dioxolan-2-one 4-methyl-1
Chemical Formula C4H6O3
Propylene carbonate is a cyclic carbonate that reacts with amines to form carbamates,
undergoes hydroxy alkylation and transesterification. It can be used as an isocyanate and
unsaturated polyester resin cleanup solvent, viscosity reducer in coatings, CO2 extraction
solvent, electrolyte in lithium batteries, polar additive for clay gellants, foundry binder
catalyst, and textile dye carrier and cleaner.