Chemistry:Lithium propionate
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| Names | |
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| Other names
Lithium propanoate
Propanyllithium EtCOOLi | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
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PubChem CID
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| Properties | |
| C3H5LiO2 | |
| Molar mass | 80.01 g·mol−1 |
| Appearance | Transparent crystals |
| Density | 1.254 g/cm3[1] |
| Melting point | 333.0 °C; 631.3 °F; 606.1 K[1] |
| 1 g/mL | |
| Solubility in ethanol | 41.7 g/L |
| Structure[1] | |
| Monoclinic | |
| P21/c (No. 14) | |
a = 9.823 Å, b = 4.9330 Å, c = 8.8120 Å α = 90°, β = 96.86°, γ = 90°
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Lattice volume (V)
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423.94 Å3 |
Formula units (Z)
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4 units per cell |
| Thermochemistry | |
Enthalpy of fusion (ΔfH⦵fus)
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197-198 kJ/kg[2] |
| Hazards | |
| GHS pictograms |  
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| GHS Signal word | Warning |
| HH315Script error: No such module "Preview warning".Category:GHS errors, HH411Script error: No such module "Preview warning".Category:GHS errors, HH412Script error: No such module "Preview warning".Category:GHS errors | |
| PP264Script error: No such module "Preview warning".Category:GHS errors, PP273Script error: No such module "Preview warning".Category:GHS errors, PP280Script error: No such module "Preview warning".Category:GHS errors, PP302+P352Script error: No such module "Preview warning".Category:GHS errors, PP321Script error: No such module "Preview warning".Category:GHS errors, PP332+P317Script error: No such module "Preview warning".Category:GHS errors, PP362+P364Script error: No such module "Preview warning".Category:GHS errors, PP391Script error: No such module "Preview warning".Category:GHS errors, PP501Script error: No such module "Preview warning".Category:GHS errors | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Lithium propionate, also known as lithium propanoate, is a lithium salt of propionic acid with the chemical formula EtCOOLi. It is the lightest of the metal propionates.
Structure
A solid−solid phase transition occurs, suggesting dimorphism despite the crystal system remaining monoclinic.[1][2]
Preparation
Lithium propionate can be prepared by treating a basic lithium salt such as lithium carbonate or lithium hydroxide with propionic acid.[1]
Uses
Lithium propionate is used in laboratory research. Like the closely related lithium acetate (LiOAc), lithium propionate is used as a buffer in certain cosmetic products.[4] Lithium propionate has also been investigated in the development of electrodes, where secondary lithium electrodes were introduced in propylene carbonate.[5] In organic synthesis, lithium propionate esters have been used to stereoselectively induce alternating methyl and methoxy moieties in α-β unsaturated esters through a Michael addition reaction.[6]
Reactions
Decomposition takes place via ketonization, yielding the symmetric ketone (3-pentanone) and lithium carbonate:[2]
- 2Li(O2CEt) → Li2CO3 + Et(CO)Et
References
- ↑ 1.0 1.1 1.2 1.3 1.4 Martínez Casado, F. J.; Riesco, M. Ramos; García Pérez, M. V.; Redondo, M. I.; López-Andrés, S.; Rodríguez Cheda, J. A. (2009-10-01). "Structural and Thermodynamic Study on Short Metal Alkanoates: Lithium Propanoate and Pentanoate". The Journal of Physical Chemistry B 113 (39): 12896–12902. doi:10.1021/jp9047715. ISSN 1520-6106. https://doi.org/10.1021/jp9047715.
- ↑ 2.0 2.1 2.2 Bui, Huong Ly; de Klerk, Arno (2013-04-11). "Lithium C1–C12n-Alkanoates: Thermal Behavior from −30 °C to 600 °C". Journal of Chemical & Engineering Data 58 (4): 1039–1049. doi:10.1021/je400054m. ISSN 0021-9568.
- ↑ PubChem. "Lithium propanoate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/23689528.
- ↑ "Lithium Propanoate; Propionic Acid". https://1source.com/ingredients/lithium-propanoate?lang=eng.
- ↑ Saltão, J. M. S.; Sequeira, C. A. C. (1983-01-01). "Study of a lithium-lithium propionate electrode in propylene carbonate". Journal of Power Sources 10 (2): 111–123. doi:10.1016/0378-7753(83)87001-3. ISSN 0378-7753. https://www.sciencedirect.com/science/article/pii/0378775383870013.
- ↑ Jo, Sunjin (2008) (in en). Asymmetric Michael Additions of Lithium Propionate Enolates to α,β-Unsaturated Esters: A Study Towards the Total Synthesis of Lonomycin A. https://repository.lib.fsu.edu/islandora/object/fsu%3A181799/.
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