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Wikipedia

Ethylene carbonate

February 05, 2023

Ethylene carbonate (sometimes abbreviated EC) is the organic compound with the formula (CH2O)2CO. It is classified as the cyclic carbonate ester of ethylene glycol and carbonic acid. At room temperature (25 °C) ethylene carbonate is a transparent crystalline solid, practically odorless and colorless, and somewhat soluble in water. In the liquid state (m.p. 34-37 °C) it is a colorless odorless liquid.[3]

Ethylene carbonate
Names
Preferred IUPAC name
1,3-Dioxolan-2-one
Other names
ethylene glycol carbonate[1]
Identifiers
  • 96-49-1 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:178725
ChEMBL
  • ChEMBL3181803
ChemSpider
  • 7030 Y
ECHA InfoCard 100.002.283
EC Number
  • 202-510-0
KEGG
  • C20363
  • 7303
UNII
  • RGJ96TB7R7 Y
  • DTXSID2026600
  • InChI=1S/C3H4O3/c4-3-5-1-2-6-3/h1-2H2 Y
    Key: KMTRUDSVKNLOMY-UHFFFAOYSA-N Y
  • InChI=1/C3H4O3/c4-3-5-1-2-6-3/h1-2H2
    Key: KMTRUDSVKNLOMY-UHFFFAOYAD
  • C1COC(=O)O1
Properties
C3H4O3
Molar mass 88.062 g·mol−1
Appearance White to yellow solid
Density 1.3210 g/cm3
Melting point 34 to 37 °C (93 to 99 °F; 307 to 310 K)
Boiling point 243.0 °C (469.4 °F; 516.1 K)
Soluble
Hazards[2]
GHS labelling:
Warning
H302, H319, H373
P260, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P314, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 150 °C (302 °F; 423 K)
465 °C (869 °F; 738 K)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Production and reactions

Ethylene carbonate is produced by the reaction between ethylene oxide and carbon dioxide. The reaction is catalyzed by a variety of cations and complexes:[4][5]

(CH2)2O + CO2 → (CH2O)2CO

In the laboratory, ethylene carbonate can also be produced from the reaction of urea and ethylene glycol using zinc oxide as a catalyst at a temperature of 150 °C and a pressure of 3 kPa:[6]

(NH2)2CO + HO−CH2CH2−OH → (CH2O)2CO + 2 NH3

Ethylene carbonate (and propylene carbonate) may be converted to dimethyl carbonate (a useful solvent and a mild methylating agent) via transesterification by methanol:

C2H4CO3 + 2 CH3OH → CH3OCO2CH3 + HOC2H4OH

The transesterfication of ethylene carbonate by methanol can be catalyzed by a high surface area (thermally exfoliated) graphitic carbon nitride (g-C3N4) materials. This method reduces the chance of metal or halide contamination, and can offer yields of up to 60% at a temperature of 393 K.[7]

Dimethyl carbonate may itself be similarly transesterified to diphenyl carbonate, a phosgene-substitute:[4]

CH3OCO2CH3 + 2 PhOH → PhOCO2Ph + 2 MeOH

Applications

Ethylene carbonate is used as a polar solvent with a molecular dipole moment of 4.9 D,[8][9] only 0.1 D lower than that of propylene carbonate.

It can be used as a high permittivity component of electrolytes in lithium batteries and lithium-ion batteries. Other components like diethyl carbonate, ethyl methyl carbonate, dimethyl carbonate and methyl acetate can be added to those electrolytes in order to decrease the viscosity and melting point.[10]

A typical sodium intercalation type battery would use an electrolyte consisting of: fluoroethylene carbonate (FEC) (99%), metallic Na (99.9%), and 1.0 M sodium perchlorate (NaClO4) solutions in ethylene carbonate and diethyl carbonate (EC/DEC), 1:1 v/v% battery-grade, mixed with FEC (10% by weight).[11]

Ethylene carbonate is also used as plasticizer, and as a precursor to vinylene carbonate, which is used in polymers and in organic synthesis.

Oxalyl chloride is produced commercially from ethylene carbonate. Photochlorination gives the tetrachloroethylene carbonate:[12]

C2H4O2CO + 4 Cl2 → C2Cl4O2CO + 4 HCl

The tetrachloride is degraded to oxalyl chloride by amine catalysts.

C2Cl4O2CO → C2O2Cl2 + COCl2

See also

External links

  • WebBook page for ethylene carbonate

References

  1. ^ "CID 7303 -- PubChem Compound Summary". pubchem.ncbi.nlm.nih.gov. Retrieved 2008-03-15.
  2. ^ "C&L Inventory". echa.europa.eu.
  3. ^ JEFFSOL ETHYLENE CARBONATE 2012-07-22 at the Wayback Machine catalog entry at www.huntsman.com. Accessed on 2010-02-18.
  4. ^ a b Buysch, Hans-Josef (2012). "Carbonic Esters". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_197.
  5. ^ Comerford, James W.; Ingram, Ian D. V.; North, Michael; Wu, Xiao (2015). "Sustainable metal-based catalysts for the synthesis of cyclic carbonates containing five-membered rings". Green Chemistry. 17 (4): 1966–1987. doi:10.1039/C4GC01719F. S2CID 96255105.
  6. ^ Bhalchandra M. Bhanage; Shin-ichiro Fujita (2003). "Transesterification of urea and ethylene glycol to ethylene carbonate as an important step for urea based dimethyl carbonate synthesis". Green Chemistry. 5 (4): 429–432. doi:10.1039/b304182d. S2CID 97286880.
  7. ^ Gan, Yu-Lin; Hu, Xiao-Qian; Wen, Lin-Zhi; Xu, Jie; Xue, Bing (2020-02-24). "Metal-free synthesis of dimethyl carbonate via transesterification of ethylene carbonate catalyzed by graphitic carbon nitride materials". New Journal of Chemistry. 44 (8): 3215–3223. doi:10.1039/C9NJ04530A. ISSN 1369-9261. S2CID 213404364.
  8. ^ Ralph P. Seward; Ernest C. Vieira (1958). "The Dielectric Constants of Ethylene Carbonate and of Solutions of Ethylene Carbonate in Water, Methanol, Benzene and Propylene Carbonate". J. Phys. Chem. 62 (1): 127–128. doi:10.1021/j150559a041.
  9. ^ Richard Payne; Ignatius E. Theodorou (1972). "Dielectric properties and relaxation in ethylene carbonate and propylene carbonate". J. Phys. Chem. 76 (20): 2892–2900. doi:10.1021/j100664a019.
  10. ^ E. R. Logan; J. R. Dahn (2018). "A Study of the Physical Properties of Li-Ion Battery Electrolytes Containing Esters". J. Electrochem. Soc. 165 (2): A21–A30. doi:10.1149/2.0271802jes. OSTI 1469344.
  11. ^ Youssef Sayed, Sayed; Kalisvaart, W. Peter; Olsen, Brian; Luber, Erik; Buriak, Jillian (2020-07-13). "Stabilizing Tin Anodes in Sodium-Ion Batteries by Alloying with Silicon". figshare. doi:10.26434/chemrxiv.12642956.v1. S2CID 243291502. Retrieved 2021-02-24.
  12. ^ Pfoertner, Karl-Heinz (2000). "Photochemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_573.

February 05, 2023
ethylene, carbonate, sometimes, abbreviated, organic, compound, with, formula, ch2o, classified, cyclic, carbonate, ester, ethylene, glycol, carbonic, acid, room, temperature, ethylene, carbonate, transparent, crystalline, solid, practically, odorless, colorle. Ethylene carbonate sometimes abbreviated EC is the organic compound with the formula CH2O 2CO It is classified as the cyclic carbonate ester of ethylene glycol and carbonic acid At room temperature 25 C ethylene carbonate is a transparent crystalline solid practically odorless and colorless and somewhat soluble in water In the liquid state m p 34 37 C it is a colorless odorless liquid 3 Ethylene carbonate NamesPreferred IUPAC name 1 3 Dioxolan 2 oneOther names ethylene glycol carbonate 1 IdentifiersCAS Number 96 49 1 Y3D model JSmol Interactive imageChEBI CHEBI 178725ChEMBL ChEMBL3181803ChemSpider 7030 YECHA InfoCard 100 002 283EC Number 202 510 0KEGG C20363PubChem CID 7303UNII RGJ96TB7R7 YCompTox Dashboard EPA DTXSID2026600InChI InChI 1S C3H4O3 c4 3 5 1 2 6 3 h1 2H2 YKey KMTRUDSVKNLOMY UHFFFAOYSA N YInChI 1 C3H4O3 c4 3 5 1 2 6 3 h1 2H2Key KMTRUDSVKNLOMY UHFFFAOYADSMILES C1COC O O1PropertiesChemical formula C 3H 4O 3Molar mass 88 062 g mol 1Appearance White to yellow solidDensity 1 3210 g cm3Melting point 34 to 37 C 93 to 99 F 307 to 310 K Boiling point 243 0 C 469 4 F 516 1 K Solubility in water SolubleHazards 2 GHS labelling PictogramsSignal word WarningHazard statements H302 H319 H373Precautionary statements P260 P261 P264 P270 P271 P280 P301 P312 P302 P352 P304 P340 P305 P351 P338 P310 P312 P314 P321 P330 P332 P313 P337 P313 P362 P403 P233 P405 P501Flash point 150 C 302 F 423 K Autoignitiontemperature 465 C 869 F 738 K Safety data sheet SDS External MSDSExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Production and reactions 2 Applications 3 See also 4 External links 5 ReferencesProduction and reactions EditEthylene carbonate is produced by the reaction between ethylene oxide and carbon dioxide The reaction is catalyzed by a variety of cations and complexes 4 5 CH2 2O CO2 CH2O 2COIn the laboratory ethylene carbonate can also be produced from the reaction of urea and ethylene glycol using zinc oxide as a catalyst at a temperature of 150 C and a pressure of 3 kPa 6 NH2 2CO HO CH2CH2 OH CH2O 2CO 2 NH3Ethylene carbonate and propylene carbonate may be converted to dimethyl carbonate a useful solvent and a mild methylating agent via transesterification by methanol C2H4CO3 2 CH3OH CH3OCO2CH3 HOC2H4OHThe transesterfication of ethylene carbonate by methanol can be catalyzed by a high surface area thermally exfoliated graphitic carbon nitride g C3N4 materials This method reduces the chance of metal or halide contamination and can offer yields of up to 60 at a temperature of 393 K 7 Dimethyl carbonate may itself be similarly transesterified to diphenyl carbonate a phosgene substitute 4 CH3OCO2CH3 2 PhOH PhOCO2Ph 2 MeOHApplications EditEthylene carbonate is used as a polar solvent with a molecular dipole moment of 4 9 D 8 9 only 0 1 D lower than that of propylene carbonate It can be used as a high permittivity component of electrolytes in lithium batteries and lithium ion batteries Other components like diethyl carbonate ethyl methyl carbonate dimethyl carbonate and methyl acetate can be added to those electrolytes in order to decrease the viscosity and melting point 10 A typical sodium intercalation type battery would use an electrolyte consisting of fluoroethylene carbonate FEC 99 metallic Na 99 9 and 1 0 M sodium perchlorate NaClO4 solutions in ethylene carbonate and diethyl carbonate EC DEC 1 1 v v battery grade mixed with FEC 10 by weight 11 Ethylene carbonate is also used as plasticizer and as a precursor to vinylene carbonate which is used in polymers and in organic synthesis Oxalyl chloride is produced commercially from ethylene carbonate Photochlorination gives the tetrachloroethylene carbonate 12 C2H4O2CO 4 Cl2 C2Cl4O2CO 4 HClThe tetrachloride is degraded to oxalyl chloride by amine catalysts C2Cl4O2CO C2O2Cl2 COCl2See also EditPropylene carbonate Vinylene carbonate Diethyl carbonate Trimethylene carbonate Carbonate ester EthyleneExternal links EditWebBook page for ethylene carbonateReferences Edit CID 7303 PubChem Compound Summary pubchem ncbi nlm nih gov Retrieved 2008 03 15 C amp L Inventory echa europa eu JEFFSOL ETHYLENE CARBONATE Archived 2012 07 22 at the Wayback Machine catalog entry at www huntsman com Accessed on 2010 02 18 a b Buysch Hans Josef 2012 Carbonic Esters Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a05 197 Comerford James W Ingram Ian D V North Michael Wu Xiao 2015 Sustainable metal based catalysts for the synthesis of cyclic carbonates containing five membered rings Green Chemistry 17 4 1966 1987 doi 10 1039 C4GC01719F S2CID 96255105 Bhalchandra M Bhanage Shin ichiro Fujita 2003 Transesterification of urea and ethylene glycol to ethylene carbonate as an important step for urea based dimethyl carbonate synthesis Green Chemistry 5 4 429 432 doi 10 1039 b304182d S2CID 97286880 Gan Yu Lin Hu Xiao Qian Wen Lin Zhi Xu Jie Xue Bing 2020 02 24 Metal free synthesis of dimethyl carbonate via transesterification of ethylene carbonate catalyzed by graphitic carbon nitride materials New Journal of Chemistry 44 8 3215 3223 doi 10 1039 C9NJ04530A ISSN 1369 9261 S2CID 213404364 Ralph P Seward Ernest C Vieira 1958 The Dielectric Constants of Ethylene Carbonate and of Solutions of Ethylene Carbonate in Water Methanol Benzene and Propylene Carbonate J Phys Chem 62 1 127 128 doi 10 1021 j150559a041 Richard Payne Ignatius E Theodorou 1972 Dielectric properties and relaxation in ethylene carbonate and propylene carbonate J Phys Chem 76 20 2892 2900 doi 10 1021 j100664a019 E R Logan J R Dahn 2018 A Study of the Physical Properties of Li Ion Battery Electrolytes Containing Esters J Electrochem Soc 165 2 A21 A30 doi 10 1149 2 0271802jes OSTI 1469344 Youssef Sayed Sayed Kalisvaart W Peter Olsen Brian Luber Erik Buriak Jillian 2020 07 13 Stabilizing Tin Anodes in Sodium Ion Batteries by Alloying with Silicon figshare doi 10 26434 chemrxiv 12642956 v1 S2CID 243291502 Retrieved 2021 02 24 Pfoertner Karl Heinz 2000 Photochemistry Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a19 573 Retrieved from https en wikipedia org w index php title Ethylene carbonate amp oldid 1121774406, wikipedia, wiki, book, books, library,

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