Ethylene carbonate
| Structural formula | ||||||||||||||||
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| General | ||||||||||||||||
| Surname | Ethylene carbonate | |||||||||||||||
| other names |
1,3-dioxolan-2-one |
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| Molecular formula | C 3 H 4 O 3 | |||||||||||||||
| Brief description |
colorless crystals |
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| properties | ||||||||||||||||
| Molar mass | 88.06 g mol −1 | |||||||||||||||
| Physical state |
firmly |
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| density |
1.32 g cm −3 (40 ° C) |
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| Melting point |
36 ° C |
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| boiling point |
248 ° C (decomposition) |
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| Vapor pressure |
21 Pa (20 ° C) |
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| solubility |
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| Refractive index |
1.4148 (50 ° C) |
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| safety instructions | ||||||||||||||||
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| Thermodynamic properties | ||||||||||||||||
| ΔH f 0 |
−508.4 kJ / mol (g) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C | ||||||||||||||||
Ethylene carbonate , also correctly referred to as 1,3-dioxolan-2-one , is a colorless and almost odorless compound that is solid at room temperature .
synthesis
Ethylene carbonate 2 is to be understood as a cyclic ester of carbonic acid and ethylene glycol , but is produced from ethylene oxide 1 and carbon dioxide (CO 2 ), quaternary ammonium salts are used as catalysts in industry, and aluminum-porphine complexes are used in the laboratory. The latter allow the addition of carbon dioxide to be carried out even under very mild conditions:
In 2007 Shell patented the particularly elegant OMEGA process , in which ethylene carbonate is produced from ethylene oxide in water and hydrolysed to ethylene glycol in the same plant. This route avoids the formation of oligomers, which is practically unavoidable in the direct ring opening of ethylene oxide.
The corresponding carbonate can be industrially produced from any epoxy or epoxy resin by pressing carbon dioxide at 2–6 bar at approx. 80 ° C onto the stirred surface of an epoxy solution in toluene or xylene.
properties
Cyclic carbonates form open-chain carbonates at approx. 120 ° C with glycols or other high-boiling alcohols.
Cyclic carbonates form open-chain urethanes with amines at approx. 80 ° C. Primary amines are much more reactive than secondary ones.
Ethylene carbonate has a flash point of 143 ° C.
use
Ethylene carbonate is used in the chemical industry as a starting material for syntheses and as a solvent at higher temperatures . So it serves as a
- High-temperature solvent used in the spinning of polynitrile fibers
- Starting material for the synthesis of oxazolidinones , imidazolidones , pyrimidines and purines
- Component in electrolyte solutions for lithium batteries
- inexpensive reagent for the introduction of 2-hydroxyethylation in amines, amides and phenols
Risk assessment
In 2015, ethylene carbonate was included in the EU's ongoing action plan ( CoRAP ) in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation . The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. Ethylene carbonate uptake was caused by concerns about consumer use , worker exposure , high (aggregated) tonnage, other hazard-related concerns and widespread use, as well as the potential risk from reproductive toxicity . The re-evaluation took place from 2018 and was carried out by Latvia . A final report was then published.
See also
Individual evidence
- ↑ a b Entry on 1,3-Dioxolan-2-one. In: Römpp Online . Georg Thieme Verlag, accessed on October 1, 2014.
- ↑ a b c d e f data sheet ethylene carbonate (PDF) from Merck , accessed on January 19, 2011.
- ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-244.
- ↑ a b Entry on ethylene carbonate in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
- ↑ CRC Handbook 9th edition (2009–2010), pp. 5–23 ( Memento of April 26, 2015 in the Internet Archive ). - Comparison with propylene carbonate : Ethylene carbonate value should be in the range -523 ... -525 kJ / mol, value -503 ± 4 kJ / mol for NIST also too low, see entry on ethylene carbonate . In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD, accessed on 22 March 2010 .
- ↑ Takuzo Aida, Shohei Inoue: Activation of carbon dioxide with aluminum porphyrin and reaction with epoxide. Studies on (tetraphenylporphinato) aluminum alkoxide having a long oxyalkylene chain as the alkoxide group. In: Journal of the American Chemical Society. 105, 1983, pp. 1304-1309, doi : 10.1021 / ja00343a038 .
- ↑ Carmen Martín, Giulia Fiorani, Arjan W. Kleij: Recent Advances in the Catalytic Preparation of Cyclic Organic Carbonates . In: ACS Catalysis 5, 2015, pp. 1353-1370, doi : 10.1021 / cs5018997 .
- ↑ Patent WO 2007088514 A1 . - WO 2011089385 A1
- ^ John H. Clements: Reactive Applications of Cyclic Alkylene Carbonates. In: Industrial & Engineering Chemistry Research. 42, 2003, pp. 663-674, doi : 10.1021 / ie020678i .
- ↑ European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report .
- ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): ethylene carbonate , accessed on May 1, 2020.