General Description
Colorless liquid.
Reactivity Profile
DIMETHYL GLUTARATE(1119-40-0) is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Air & Water Reactions
Flammable. Hydrolyzed by strong mineral acids and strong alkalis.
Health Hazard
May be harmful by inhalation, ingestion, or skin absorption. May cause irritation.
Chemical Properties
CLEAR COLOURLESS LIQUID
Flammability and Explosibility
Nonflammable
Safety
Dimethyl Glutarate belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group. DIMETHYL GLUTARATE is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Dimethyl glutarate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dimethyl glutarate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Synthesis
Phosphorus trichloride (PCl3, 8 mL) was added dropwise to a methanol (50 mL) solution of glutaric acid (13.2 g, 0.10 mol) under ice-bath cooling and continuous stirring. Upon completion of the reaction, the solvent was removed from the reaction mixture under reduced pressure. Subsequently, the resulting residue was distilled under reduced pressure. Fractions with boiling points of 110-112 °C were collected to give dimethyl glutarate in a yield of 14.7 g and 92% yield.
Structure and conformation
Dimethyl glutarate (DM) contains two carbonyl groups and exhibits a symmetrical structure. In terms of molecular electrostatics, the two carbonyl oxygen atoms have identical electronegativity. As a result, when coordinating with lithium ions, these oxygen atoms display equivalent reactivity, facilitating the formation of various coordination structures—including chelation, bridging, and monodentate coordination—that significantly enhance the high-voltage stability of the electrolyte.
Toxics Screening Level
The ITSL for Dimethyl Glutarate is 0.5 μg/m3 based on annual averaging time.
References
[1] Analytical Chemistry, 2004, vol. 76, # 16, p. 4765 - 4778
[2] Patent: US2016/31858, 2016, A1. Location in patent: Paragraph 0143
[3] Recueil des Travaux Chimiques des Pays-Bas, 1899, vol. 18, p. 373
[4] Chem. Zentralbl., 1918, vol. 89, # I, p. 1144
[5] Recueil des Travaux Chimiques des Pays-Bas, 1926, vol. 45, p. 586
