Chemistry:Diethyl succinate
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Names | |
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Preferred IUPAC name
Diethyl butanedioate | |
Other names
Diethyl succinate
Butanedioic acid diethyl ester Clorius | |
Identifiers | |
3D model (JSmol)
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907645 | |
ChemSpider | |
PubChem CID
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RTECS number |
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UNII | |
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Properties | |
C8H14O4 | |
Molar mass | 174.196 g·mol−1 |
Appearance | Colorless liquid |
Density | 1.047 g/mL |
Melting point | −20 °C (−4 °F; 253 K) |
Boiling point | 218 °C (424 °F; 491 K) |
Slightly soluble | |
Vapor pressure | 0.13 mmHg |
-105.07·10−6 cm3/mol | |
Thermochemistry | |
Std enthalpy of
combustion (ΔcH⦵298) |
24.22 kJ/g |
Hazards | |
Main hazards | Primary irritant |
NFPA 704 (fire diamond) | |
Flash point | 90.56 °C (195.01 °F; 363.71 K) |
Explosive limits | 1.1-6.5% |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Diethyl succinate is the diethyl ester of succinate.
It is a colorless liquid with the formula (CH2CO2Et)2 (Et = ethyl). The organic molecule contains two ester groups. This ester is a versatile chemical intermediate. A colorless liquid, diethyl succinate is formed by Fischer esterification of succinic acid and ethanol.
Reactions
Being a diester, diethyl succinate is a particularly versatile building block. It participates in acyloin condensation to give 2-hydroxycyclobutanone.[1] Via condensation with oxalate esters, it serves as a precursor to ketoglutaric acid.[2] It is a reagent in the Stobbe condensation. thumb|222px|left|[[Diethylsuccinoylsuccinate, a useful precursor to dyes and pigments, is produced by base-induced condensation of diethyl succinate.[3]]]
References
- ↑ Bloomfield, Jordan J.; Nelke, Janice M. (1977). "Acyloin Condensation in Which Chlorotrimethylsilane is Used as a Trapping Agent: 1,2-Bis(Trimethylsilyloxy)Cyclobutene and 2-Hydroxycyclobutanone". Organic Syntheses 57: 1. doi:10.15227/orgsyn.057.0001.
- ↑ Bottorff, E. M.; Moore, L. L. (1964). "α-Ketoglutaric Acid". Organic Syntheses 44: 67. doi:10.15227/orgsyn.044.0067.
- ↑ Hunger, K.; Herbst, W. (2012). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a20_371.(Subscription content?)
![]() | Original source: https://en.wikipedia.org/wiki/Diethyl succinate.
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