Abstract:
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.
CAS No: 108-32-7
EC No.: 203-572-1
Synonyms:
PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; 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; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; 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; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; DSSTox_GSID_26789; Propylene carbonate, 99.5%; CAS-108-32-7; PC-HP; Propylene carbonate, 99.5%, anhydrous, AcroSeal(R); Propylene carbonate [USAN]; butylhexanoate; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; 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; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; 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; MFCD00798264; MFCD00798265; NSC-11784; STL373011; AKOS009158417; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; MCULE-9055336051; Propylene Carbonate (Industrial Grade); VC30366; Propylene carbonate, anhydrous, 99.7%; NCGC00165974-01; NCGC00165974-02; NCGC00256995-01; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; NCGC00259596-01; Propylene carbonate, for HPLC, 99.7%; AK109386; AK688454; BP-30108; LS-51953; O433; SC-65189; SY008770; SY066861; DB-018081; Propylene carbonate, ReagentPlus(R), 99%; CS-0076373; FT-0602265; FT-0639979; FT-0660009; FT-0674103; P0525; 4-Methyl-1,3-dioxolan-2-one 108-32-7; D05633; 2-Propenoic acid, 2-methyl-3-(2-nitrophenyl)-; 23262-EP2269986A1; 23262-EP2274983A1; 23262-EP2284165A1; 23262-EP2292593A2; 23262-EP2295399A2; 23262-EP2308858A1; 23262-EP2308862A1; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; 23262-EP2309584A1; 23262-EP2311816A1; 23262-EP2311817A1; 23262-EP2311821A1; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; 23262-EP2311842A2; 23262-EP2314558A1; 23262-EP2314584A1; 23262-EP2315303A1; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; 23262-EP2375479A1; 45160-EP2292593A2; 45160-EP2311821A1; 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; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; Propylene carbonate, United States Pharmacopeia (USP) Reference Standard; 1,2-PROPANEDIOL CYCLIC CARBONATE; 1,2-PROPYLENE CARBONATE; 1,2-PROPYLENE GLYCOL CARBONATE; 2-OXO-4-METHYL-1,3-DIOXOLANE; 4-METHYL-1,3-DIOXOL-2-ONE; 4-METHYL-1,3-DIOXOLAN-2-ONE; 4-METHYL-1,3-DIOXOLANE-2-ONE; ARCONATE; ARCONATE(R) PC; CARBONIC ACID CYCLIC PROPYLENE ESTER; CARBONIC ACID PROPYLENE GLYCOL ESTER; PC; PROPANEDIOL CYCLIC CARBONATE; PROPYLENE CARBONATE; PROPYLENE CARBONATE S; PROPYLENE GLYCOL CARBONATE; (±)-Methyl-1,3-dioxolan-2-one; (R,S)-4-Methyl-[1,3]dioxolan-2-one; 1,2-PDC; 1,2-Propanediol carbonate; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; 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; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; 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; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; DSSTox_GSID_26789; Propylene carbonate, 99.5%; CAS-108-32-7; PC-HP; Propylene carbonate, 99.5%, anhydrous, AcroSeal(R); Propylene carbonate [USAN]; butylhexanoate; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; 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; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; 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; MFCD00798264; MFCD00798265; NSC-11784; STL373011; AKOS009158417; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; MCULE-9055336051; Propylene Carbonate (Industrial Grade); VC30366; Propylene carbonate, anhydrous, 99.7%; NCGC00165974-01; NCGC00165974-02; NCGC00256995-01; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; NCGC00259596-01; Propylene carbonate, for HPLC, 99.7%; AK109386; AK688454; BP-30108; LS-51953; O433; SC-65189; SY008770; SY066861; DB-018081; Propylene carbonate, ReagentPlus(R), 99%; CS-0076373; FT-0602265; FT-0639979; FT-0660009; FT-0674103; P0525; 4-Methyl-1,3-dioxolan-2-one 108-32-7; D05633; 2-Propenoic acid, 2-methyl-3-(2-nitrophenyl)-; 23262-EP2269986A1; 23262-EP2274983A1; 23262-EP2284165A1; 23262-EP2292593A2; 23262-EP2295399A2; 23262-EP2308858A1; 23262-EP2308862A1; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; 23262-EP2309584A1; 23262-EP2311816A1; 23262-EP2311817A1; 23262-EP2311821A1; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; 23262-EP2311842A2; 23262-EP2314558A1; 23262-EP2314584A1; 23262-EP2315303A1; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; 23262-EP2375479A1; 45160-EP2292593A2; 45160-EP2311821A1; 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; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat; Propylene carbonate, United States Pharmacopeia (USP) Reference Standard; 1,2-PROPANEDIOL CYCLIC CARBONATE; 1,2-PROPYLENE CARBONATE; 1,2-PROPYLENE GLYCOL CARBONATE; 2-OXO-4-METHYL-1,3-DIOXOLANE; 4-METHYL-1,3-DIOXOL-2-ONE; 4-METHYL-1,3-DIOXOLAN-2-ONE; 4-METHYL-1,3-DIOXOLANE-2-ONE; ARCONATE; ARCONATE(R) PC; CARBONIC ACID CYCLIC PROPYLENE ESTER; CARBONIC ACID PROPYLENE GLYCOL ESTER; PC; PROPANEDIOL CYCLIC CARBONATE; PROPYLENE CARBONATE; PROPYLENE CARBONATE S; PROPYLENE GLYCOL CARBONATE; (±)-Methyl-1,3-dioxolan-2-one; (R,S)-4-Methyl-[1,3]dioxolan-2-one; 1,2-PDC; 1,2-Propanediol carbonate; PROPYLENE CARBONATE; Propylene carbonate; PROPİLEN KARBONAT; propilen karbonat
PROPYLENE CARBONATE
Abstract:
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.
Propylene carbonate
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Propylene carbonate[1][2]
Propylene Carbonate V.1.svg
Propylene-carbonate-3D-vdW.png
Sample of propylene carbonate.jpg
Names
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
Identifiers
CAS Number
108-32-7 check
3D model (JSmol)
Interactive image
ChemSpider
7636 ☒
ECHA InfoCard 100.003.248 Edit this at Wikidata
PubChem CID
7924
UNII
8D08K3S51E check
CompTox Dashboard (EPA)
DTXSID2026789 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
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
Structure
Dipole moment 4.9 D
Hazards
Main hazards Xi
Safety data sheet MSDS by Mallinckrodt Baker
R-phrases (outdated) R36
S-phrases (outdated) S26 S36
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
111
Flash point 132 °C (270 °F; 405 K)
Autoignition
temperature 455 °C (851 °F; 728 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒ verify (what is check☒ ?)
Infobox references
Propylene carbonate (often abbreviated PC) is an organic compound with the formula C4H6O3. It is a cyclic carbonate ester derived from propylene glycol.[3] This colorless and odorless liquid is useful as a polar, aprotic solvent.[4] Propylene carbonate is chiral, but is used exclusively as the racemic mixture in most contexts.
Contents
1 Preparation
2 Applications
2.1 As a solvent
2.2 Other
3 Safety
4 See also
5 References
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[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.[5]
Applications
As a solvent
Propylene carbonate is used as a polar, aprotic solvent.[6] 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).[1] 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.[7]
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.[8]
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.[10]
Other
Propylene carbonate product may be converted to other carbonate esters by transesterification as well (see Carbonate ester#Carbonate transesterification).[4]
In electrospray ionization mass spectrometry, propylene carbonate is doped into low surface tension solutions to increase analyte charging.[11]
In Grignard reaction propylene carbonate (or most other carbonate esters) 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.[12] 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.[13]
Uses propylene carbonate as a physical solvent to remove CO2 and H2S
Propylene carbonate also removes C3+ hydrocarbons, COS, SO2, CS2, and H2O from the natural gas stream.
Thus, in one step the natural gas can be sweetened and dehydrated to pipeline quality.
Process is used for bulk removal of CO2 and is not used to treat to less than 3% CO2.
System requires special design features such as larger absorbers and higher circulation rates to obtain pipeline quality and usually is not economically applicable for these outlet requirements.
Propylene carbonate has the following characteristics, which make it suitable as a solvent for acid gas treating:
The Fluor process (licensed by Fluor Daniel, Inc.) uses propylene carbonate to remove CO2, H2S, hydrocarbons, COS, CS2, and H2O from natural gas. Thus, in one step, the natural gas can be sweetened and dehydrated.
The Fluor process is used to remove the bulk CO2 down to 3%. It can be also used for treating feed gases containing low levels of H2S, typically less than 20 ppmv. However, improved stripping allows treatment to meet H2S sales gas requirement for gases containing up to 200 ppmv H2S. This new improvement in stripping uses medium pressure (125 psia) flash gas as the stripping medium in a vacuum stripper (Mak et al., 2007). It should be noted that hydrocarbon losses increase as the amount of stripping gas increases.
The Fluor solvent can operate at lower temperatures without becoming too viscous for good mass transfer. The operating temperature for propylene carbonate is limited to greater than 0°F and a maximum operating temperature of 149°F.
Propylene carbonate has low solubility for light hydrocarbons, which results in lower hydrocarbon losses in the vent gas stream. A new Fluor process improvement involves feed chilling to 0°F in order to reduce absorption of hydrocarbons. Chilling also increases the solvent's acid gas holding capacity, resulting in a lower overall solvent circulation rate and lower plant cost.
What Is Propylene Carbonate?
Propylene carbonate is an ingredient that is used in cosmetics and skincare products. Propylene carbonate is mainly used to dissolve or suspend other ingredients in a formulation and also to decrease the thickness of formulations.
Propylene glycol is a small, water-soluble alcohol that is a very common ingredient in cosmetics and personal care products. It is a synthetic product obtained from the hydration of propylene oxide, which is derived from petroleum products. Therefore, propylene carbonate can also be considered a petroleum-derived product. Propylene carbonate is a colorless and odorless liquid.
In addition, to use in the cosmetic industry, propylene carbonate can be found in some adhesives and paint strippers. It is also used as a plasticizer, which means that it increases the plasticity or decreases the viscosity of a material.
THE BREAKDOWN
Propylene Carbonate
THE GOOD:Propylene carbonate is mainly used to dissolve or suspend other ingredients in a formulation and also to decrease the thickness of formulations.
THE NOT SO GOOD:Propylene carbonate can also be considered a petroleum-derived product, which isn’t necessarily a bad thing as it is highly purified.
WHO IS IT FOR?All skin types except those that have an identified allergy to it.
SYNERGETIC INGREDIENTS:Works well with most ingredients
KEEP AN EYE ON:Can cause some irritation, particularly in sensitive or irritated skin.
Why Is Propylene Carbonate Used?
In cosmetics and skincare products, propylene carbonate primarily functions as a solvent, meaning that it dissolves other ingredients. It is typically used at concentrations ranging from less than 0.1% to 5%. Propylene carbonate is used in the formulation of makeup, primarily lipstick, eye shadow, and mascara, as well as in skin cleansing products.
Texture
As a solvent, propylene carbonate helps to dissolve or suspend other ingredients in a formulation without changing the other ingredients. Propylene carbonate allows for an even distribution of all ingredients in a cosmetic formulation and creates an appropriate consistency for the product.
Thickness
Furthermore, solvents like propylene carbonate are used to thin out formulations and decrease viscosity. The term viscosity corresponds to the concept of ‘thickness’. Decreasing the viscosity of a formulation makes the product more spreadable when applied to the skin or hair. Solvents can also increase the efficacy of active ingredients in a product formulation by enhancing their absorption through the skin.
Is Propylene Carbonate Safe?
The safety of propylene carbonate has been assessed by the Cosmetic Ingredient Review Expert Panel, a group that evaluates the safety of skincare and cosmetic products. In clinical studies, undiluted propylene carbonate was found to be moderately irritating to the eye and skin, but it was non-toxic by inhalation exposure.
Products containing up to 20% propylene carbonate were determined to be moderately irritating to human skin, however, they were non-sensitizing, non-phototoxic, and non-photosensitizing. It should be noted that this concentration is much higher than the concentrations typically used in cosmetic formulations, which range from less than 0.1% to 5%. After evaluating the scientific data, the Expert Panel concluded that propylene carbonate was safe as a cosmetic ingredient in the present practices of use and concentration.
The United States Food and Drug Administration has reviewed the safety of propylene carbonate and approved its use as an indirect food additive as a component of adhesives.
Abstract:
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.
Propylene carbonate
Jump to navigationJump to search
Propylene carbonate[1][2]
Propylene Carbonate V.1.svg
Propylene-carbonate-3D-vdW.png
Sample of propylene carbonate.jpg
Names
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
Identifiers
CAS Number
108-32-7 check
3D model (JSmol)
Interactive image
ChemSpider
7636 ☒
ECHA InfoCard 100.003.248 Edit this at Wikidata
PubChem CID
7924
UNII
8D08K3S51E check
CompTox Dashboard (EPA)
DTXSID2026789 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
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
Structure
Dipole moment 4.9 D
Hazards
Main hazards Xi
Safety data sheet MSDS by Mallinckrodt Baker
R-phrases (outdated) R36
S-phrases (outdated) S26 S36
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
111
Flash point 132 °C (270 °F; 405 K)
Autoignition
temperature 455 °C (851 °F; 728 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒ verify (what is check☒ ?)
Infobox references
Propylene carbonate (often abbreviated PC) is an organic compound with the formula C4H6O3. It is a cyclic carbonate ester derived from propylene glycol.[3] This colorless and odorless liquid is useful as a polar, aprotic solvent.[4] Propylene carbonate is chiral, but is used exclusively as the racemic mixture in most contexts.
Contents
1 Preparation
2 Applications
2.1 As a solvent
2.2 Other
3 Safety
4 See also
5 References
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[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.[5]
Applications
As a solvent
Propylene carbonate is used as a polar, aprotic solvent.[6] 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).[1] 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.[7]
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.[8]
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.[10]
Other
Propylene carbonate product may be converted to other carbonate esters by transesterification as well (see Carbonate ester#Carbonate transesterification).[4]
In electrospray ionization mass spectrometry, propylene carbonate is doped into low surface tension solutions to increase analyte charging.[11]
In Grignard reaction propylene carbonate (or most other carbonate esters) 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.[12] 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.[13]
Uses propylene carbonate as a physical solvent to remove CO2 and H2S
Propylene carbonate also removes C3+ hydrocarbons, COS, SO2, CS2, and H2O from the natural gas stream.
Thus, in one step the natural gas can be sweetened and dehydrated to pipeline quality.
Process is used for bulk removal of CO2 and is not used to treat to less than 3% CO2.
System requires special design features such as larger absorbers and higher circulation rates to obtain pipeline quality and usually is not economically applicable for these outlet requirements.
Propylene carbonate has the following characteristics, which make it suitable as a solvent for acid gas treating:
The Fluor process (licensed by Fluor Daniel, Inc.) uses propylene carbonate to remove CO2, H2S, hydrocarbons, COS, CS2, and H2O from natural gas. Thus, in one step, the natural gas can be sweetened and dehydrated.
The Fluor process is used to remove the bulk CO2 down to 3%. It can be also used for treating feed gases containing low levels of H2S, typically less than 20 ppmv. However, improved stripping allows treatment to meet H2S sales gas requirement for gases containing up to 200 ppmv H2S. This new improvement in stripping uses medium pressure (125 psia) flash gas as the stripping medium in a vacuum stripper (Mak et al., 2007). It should be noted that hydrocarbon losses increase as the amount of stripping gas increases.
The Fluor solvent can operate at lower temperatures without becoming too viscous for good mass transfer. The operating temperature for propylene carbonate is limited to greater than 0°F and a maximum operating temperature of 149°F.
Propylene carbonate has low solubility for light hydrocarbons, which results in lower hydrocarbon losses in the vent gas stream. A new Fluor process improvement involves feed chilling to 0°F in order to reduce absorption of hydrocarbons. Chilling also increases the solvent's acid gas holding capacity, resulting in a lower overall solvent circulation rate and lower plant cost.
What Is Propylene Carbonate?
Propylene carbonate is an ingredient that is used in cosmetics and skincare products. Propylene carbonate is mainly used to dissolve or suspend other ingredients in a formulation and also to decrease the thickness of formulations.
Propylene glycol is a small, water-soluble alcohol that is a very common ingredient in cosmetics and personal care products. It is a synthetic product obtained from the hydration of propylene oxide, which is derived from petroleum products. Therefore, propylene carbonate can also be considered a petroleum-derived product. Propylene carbonate is a colorless and odorless liquid.
In addition, to use in the cosmetic industry, propylene carbonate can be found in some adhesives and paint strippers. It is also used as a plasticizer, which means that it increases the plasticity or decreases the viscosity of a material.
THE BREAKDOWN
Propylene Carbonate
THE GOOD:Propylene carbonate is mainly used to dissolve or suspend other ingredients in a formulation and also to decrease the thickness of formulations.
THE NOT SO GOOD:Propylene carbonate can also be considered a petroleum-derived product, which isn’t necessarily a bad thing as it is highly purified.
WHO IS IT FOR?All skin types except those that have an identified allergy to it.
SYNERGETIC INGREDIENTS:Works well with most ingredients
KEEP AN EYE ON:Can cause some irritation, particularly in sensitive or irritated skin.
Why Is Propylene Carbonate Used?
In cosmetics and skincare products, propylene carbonate primarily functions as a solvent, meaning that it dissolves other ingredients. It is typically used at concentrations ranging from less than 0.1% to 5%. Propylene carbonate is used in the formulation of makeup, primarily lipstick, eye shadow, and mascara, as well as in skin cleansing products.
Texture
As a solvent, propylene carbonate helps to dissolve or suspend other ingredients in a formulation without changing the other ingredients. Propylene carbonate allows for an even distribution of all ingredients in a cosmetic formulation and creates an appropriate consistency for the product.
Thickness
Furthermore, solvents like propylene carbonate are used to thin out formulations and decrease viscosity. The term viscosity corresponds to the concept of ‘thickness’. Decreasing the viscosity of a formulation makes the product more spreadable when applied to the skin or hair. Solvents can also increase the efficacy of active ingredients in a product formulation by enhancing their absorption through the skin.
Is Propylene Carbonate Safe?
The safety of propylene carbonate has been assessed by the Cosmetic Ingredient Review Expert Panel, a group that evaluates the safety of skincare and cosmetic products. In clinical studies, undiluted propylene carbonate was found to be moderately irritating to the eye and skin, but it was non-toxic by inhalation exposure.
Products containing up to 20% propylene carbonate were determined to be moderately irritating to human skin, however, they were non-sensitizing, non-phototoxic, and non-photosensitizing. It should be noted that this concentration is much higher than the concentrations typically used in cosmetic formulations, which range from less than 0.1% to 5%. After evaluating the scientific data, the Expert Panel concluded that propylene carbonate was safe as a cosmetic ingredient in the present practices of use and concentration.
The United States Food and Drug Administration has reviewed the safety of propylene carbonate and approved its use as an indirect food additive as a component of adhesives.