Dimethyl oxalate Chemical Properties

Melting point:

50-54 °C (lit.)

Boiling point:

163.5 °C (lit.)

Density 

1.148 g/mL at 25 °C (lit.)

vapor pressure 

3 hPa (20 °C)

refractive index 

n20/D 1.39(lit.)

Flash point:

167 °F

storage temp. 

Store below +30°C.

solubility 

ethanol: soluble50mg/mL, clear to very slightly hazy, colorless

form 

Crystalline Solid

Specific Gravity

1.148

color 

Colorless to white

PH

1 (60g/l, H2O, 20℃)

Water Solubility 

60 G/L (25 ºC)

Merck 

14,6106

BRN 

1071744

Dielectric constant

3.0（20℃）

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents, acids, bases, reducing agents.

InChIKey

LOMVENUNSWAXEN-UHFFFAOYSA-N

LogP

-0.170

CAS DataBase Reference

553-90-2(CAS DataBase Reference)

NIST Chemistry Reference

Ethanedioic acid, dimethyl ester(553-90-2)

EPA Substance Registry System

Ethanedioic acid, dimethyl ester (553-90-2)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/38-36-22

Safety Statements 

26-36/37-24/25-23

RIDADR 

1759

WGK Germany 

3

RTECS 

RO2850000

Autoignition Temperature

480 °C

TSCA 

Yes

HS Code 

2917 11 00

HazardClass 

6.1(b)

PackingGroup 

III

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Dimethyl oxalate Usage And Synthesis

Description

Dimethyl oxalate is a chemical compound with formula (CH₃)₂(COO)₂. It is the dimethyl ester of oxalic acid.

General Description

Dimethyl oxalate (DMO), (CH3OCO)2 is an industrial chemical intermediate with versatile properties. DMO is used as a solvent and extraction agent to produce ethylene glycol, ethanol, oxalic acid, oxamide, dyes, and medicines. Besides, dimethyl carbonate (DMC), (CH3O)2CO is attracting lots of interest because of its excellent solubility, biodegradability and low toxicity. DMC could be used as a green solvent, as electrolytes in lithium batteries, as a potential fuel additive and for polycarbonate synthesis[1].

Chemical Properties

colourless crystals

Chemical Properties

The empirical formula of dimethyl oxalate is C4H6O4. It exists as a liquid between its pour point (52°C) and boiling point (163.4°C). It is soluble in ethanol and ether and slightly soluble in water.

Uses

Dimethyl oxalate is used as an alternate fuel in the direct oxidation fuel cell. It is involved in the catalytic hydrogenation using Cu/SiO22ub> to prepare ethylene glycol. It is also used in the selective gas-phase hydrogenation catalyzed by Ag/SiO2 to get the corresponding alcohol.

Definition

ChEBI: Methyl oxalate is a diester, a methyl ester and a member of dicarboxylic acids and O-substituted derivatives. It is functionally related to an oxalic acid.

Synthesis Reference(s)

The Journal of Organic Chemistry, 24, p. 261, 1959 DOI: 10.1021/jo01084a633

General Description

Dimethyl oxalate undergoes Cu/SiO₂ catalyzed hydrogenation to yield ethylene glycol. It undergoes selective gas-phase hydrogenation catalyzed by Ag/SiO₂ to yield corresponding alcohol.

Purification Methods

Crystallise the ester repeatedly from EtOH. De-gas it under nitrogen at high vacuum and distil it. [Beilstein 2 IV 1847.]

References

[1] Chunzheng Wang. “Emerging Co-Synthesis of Dimethyl Oxalate and Dimethyl Carbonate Using Pd/Silicalite-1 Catalyst with Synergistic Interactions of Pd and Silanols.” SSRN Electronic Journal 71 1 (2023).

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