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Dimethyl oxalate

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Dimethyl oxalate Basic information

Product Name:
Dimethyl oxalate
Synonyms:
  • OXALIC ACID METHYL ESTER
  • OXALIC ACID BIS-METHYL ESTER
  • OXALIC ACID DIMETHYL ESTER
  • CH3OCOCOOCH3
  • Dimethyl ester of oxalic acid
  • Ethanedioc acid dimethyl ester
  • Ethanedioicacid,dimethylester
  • Ethanedioicaciddimethylester
CAS:
553-90-2
MF:
C4H6O4
MW:
118.09
EINECS:
209-053-6
Product Categories:
  • Organics
  • Pyridines
  • Pharmaceutical Intermediates
  • C2 to C5
  • Carbonyl Compounds
  • Esters
  • K00001
Mol File:
553-90-2.mol
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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
color 
Colorless to white
Specific Gravity
1.148
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)
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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

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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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