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Propylenecarbonate is a cyclic carbonate that is commonly used as a solvent and as a reactive intermediate in organic synthesis.
Propylenecarbonate is being considered as a potential electrochemical solvent due to its low vapor pressure, high dielectric constant and high chemical stability.
Propylenecarbonate can be synthesized from propylene oxide and CO2.
CAS: 108-32-7
MF: C4H6O3
MW: 102.09
EINECS: 203-572-1
Optically active form of propylenecarbonate can be prepared from the reaction between CO2 and racemic epoxides.
Decomposition of propylenecarbonate on the graphite electrode in lithium batteries results in the formation of a lithium intercalated compound.
Propylenecarbonate (often abbreviated PC) is an organic compound with the formula C4H6O3.
Propylenecarbonate is a cyclic carbonate ester derived from propylene glycol.
This colorless and odorless liquid is useful as a polar, aprotic solvent.
Propylenecarbonate is chiral, but is used as the racemic mixture in most contexts.
Propylenecarbonate is an ingredient that is used in cosmetics and skincare products.
Propylenecarbonate is mainly used to dissolve or suspend other ingredients in a formulation and also to decrease the thickness of formulations.
Propylenecarbonate is a small, water-soluble alcohol that is a very common ingredient in cosmetics and personal care products.
Propylenecarbonate is a synthetic product obtained from the hydration of propylene oxide, which is derived from petroleum products.
Therefore, Propylenecarbonate can also be considered a petroleum-derived product.
Propylenecarbonate is a colorless and odorless liquid.
In addition, to use in the cosmetic industry, Propylenecarbonate can be found in some adhesives and paint strippers.
Propylenecarbonate is also used as a plasticizer, which means that it increases the plasticity or decreases the viscosity of a material.
Propylenecarbonate is a PU-plasticizer and it is VOC-free clear polar solvent having high boiling and flashpoints.
Propylenecarbonate is a carbonate ester derived from propylene glycol with the peculiarity to have a low order of toxicity and a mild ether-like odor.
Propylenecarbonate is stable under most conditions and it is not hydroscopic or corrosive.
Propylenecarbonate can be synthesized from propylene oxide and CO2.
Optically active form of propylenecarbonate can be prepared from the reaction between CO2 and racemic epoxides.
Decomposition of propylenecarbonate on the graphite electrode in lithium batteries results in the formation of a lithium intercalated compound.
Propylenecarbonate is a cyclic carbonate that is commonly used as a solvent and as a reactive intermediate in organic synthesis.
Propylenecarbonate is being considered as a potential electrochemical solvent due to its low vapor pressure, high dielectric constant and high chemical stability.
Propylenecarbonate Chemical Properties
Melting point: -55 °C (lit.)
Boiling point: 240 °C (lit.)
Density: 1.204 g/mL at 25 °C (lit.)
Vapor pressure: 0.13 mm Hg ( 20 °C)
Refractive index: n20/D 1.421(lit.)
Fp: 270 °F
Storage temp.: Store below +30°C.
Solubility: 240g/l
Form: Liquid
pka: 3.92[at 20 ℃]
Specific Gravity: 1.209 (20/4℃)
Color: Clear
PH: 7.0 (200g/l, H2O, 20℃)
Relative polarity: 6
Explosive limit: 1.8-14.3%(V)
Water Solubility: 240 g/L (20 ºC)
λmax: λ: 235 nm Amax: 1.00
λ: 280 nm Amax: 0.50
λ: 300 nm Amax: 0.30
λ: 350 nm Amax: 0.05
λ: 375-400 nm Amax: 0.01
BRN: 107913
Stability: Stable. Incompatible with strong oxidizing agents, acids, bases, reducing agents. Protect from contact with moist air or water.
InChIKey: RUOJZAUFBMNUDX-UHFFFAOYSA-N
LogP: -0.41 at 20℃
CAS DataBase Reference: 108-32-7(CAS DataBase Reference)
NIST Chemistry Reference: Propylenecarbonate(108-32-7)
EPA Substance Registry System: Propylenecarbonate (108-32-7)
Uses
Propylenecarbonate is used in chemical reactions as a solvent, plasticizer, solubilizer, or dilutent.
Propylenecarbonate is also used in the synthesis of solar cells as well as lithium ion batteries.
Propylenecarbonate is particularly well suited for applications requiring a water-white product or high purity.
Propylenecarbonate 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.
Being a cyclic carbonate reacts with amines to form carbamates, undergoes hydroxy alkylation and transesterification Propylenecarbonate 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.
As a Solvent
Propylenecarbonate is used as a polar, aprotic solvent.
Propylenecarbonate has a high molecular dipole moment (4.9 D), considerably higher than those of acetone (2.91 D) and ethyl acetate (1.78 D).
Propylenecarbonate is possible, for example, to obtain potassium, sodium, and other alkali metals by electrolysis of their chlorides and other salts dissolved in propylene carbonate.
Electrolyte
Due to its high relative permittivity (dielectric constant) of 64, Propylenecarbonate 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 Propylenecarbonate to create an effective solvation shell around lithium ions, thereby creating a conductive electrolyte.
However, Propylenecarbonate is not used in lithium-ion batteries due to its destructive effect on graphite.
Propylenecarbonate can also be found in some adhesives, paint strippers, and in cosmetics.
Propylenecarbonate is also used as plasticizer.
Propylenecarbonate is also used as a solvent for removal of CO2 from natural gas and synthesis gas where H2S is not also present.
Propylenecarbonate 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
Propylenecarbonate product may be converted to other carbonate esters by transesterification as well.
In electrospray ionization mass spectrometry, propylenecarbonate is doped into low surface tension solutions to increase analyte charging.
In Grignard reaction propylenecarbonate (or most other carbonate esters) might be used to create tertiary alcohols.
Pharmaceutical Uses
Propylenecarbonate is used mainly as a solvent in oral and topical pharmaceutical formulations.
In topical applications, propylenecarbonate has been used in combination with propylene glycol as a solvent for corticosteroids.
The corticosteroid is dissolved in the solvent mixture to yield microdroplets that can then be dispersed in petrolatum.
Propylenecarbonate has been used as a dispensing solvent in topical preparations.
Propylenecarbonate has also been used in hard gelatin capsules as a nonvolatile, stabilizing, liquid carrier.
For formulations with a low dosage of active drug, a uniform drug content may be obtained by dissolving the drug in propylenecarbonate and then spraying this solution on to a solid carrier such as compressible sugar; the sugar may then be filled into hard gelatin capsules
Propylenecarbonate may additionally be used as a solvent, at room and elevated temperatures, for many cellulose-based polymers and plasticizers.
Propylenecarbonate is also used in cosmetics.
Production Methods
Propylenecarbonate may be prepared by the reaction of sodium bicarbonate with propylene chlorohydrin.
Purification Methods
Propylenecarbonate is manufactured by reaction of 1,2-propylene oxide with CO2 in the presence of a catalyst (quaternary ammonium halide).
Contaminants include propylene oxide, carbon dioxide, 1,2-and 1,3-propanediols, allyl alcohol and ethylene carbonate.
Propylenecarbonate can be purified by percolation through molecular sieves (Linde 5A, dried at 350o for 14hours under a stream of argon), followed by distillation under a vacuum.
Propylenecarbonate can be stored over molecular sieves under an inert gas atmosphere.
When purified in this way it contains less than 2ppm of water.
Activated alumina and dried CaO have also been used as drying agents prior to fractional distillation under reduced pressure.
Propylenecarbonate has been dried with 3A molecular sieves and distilled under nitrogen in the presence of p-toluenesulfonic acid, then redistilled and the middle fraction collected.
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 propylenecarbonate but also oligomeric products.
Propylenecarbonate can also be synthesized from urea and propylene glycol over zinc acetate.
Synonyms
PROPYLENE CARBONATE
108-32-7
4-Methyl-1,3-dioxolan-2-one
1,2-Propylene carbonate
1,2-Propanediol cyclic carbonate
Texacar PC
1,3-Dioxolan-2-one, 4-methyl-
Cyclic propylene carbonate
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]
DTXSID2026789
8D08K3S51E
Propylene carbonate (NF)
WLN: T5OVOTJ D
DTXCID006789
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
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
110320-40-6
