553-90-2

Name	Dimethyl oxalate
CAS	553-90-2
EINECS(EC#)	209-053-6
Molecular Formula	C4H6O4
MDL Number	MFCD00008442
Molecular Weight	118.09
MOL File	553-90-2.mol

Chemical Properties

Appearance	colourless crystals
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.)
Fp	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℃)
Stability:	Stable. Combustible. Incompatible with strong oxidizing agents, acids, bases, reducing agents.
Water Solubility	60 G/L (25 ºC)
Merck	14,6106
BRN	1071744
Dielectric constant	3.0（20℃）
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	553-90-2(EPA Substance)

Safety Data

Hazard Codes	Xi,Xn
Risk Statements	R36/38:Irritating to eyes and skin . R36:Irritating to the eyes. R22:Harmful if swallowed. less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36/37:Wear suitable protective clothing and gloves . S24/25:Avoid contact with skin and eyes . S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . less more
RIDADR	1759
WGK Germany	3
RTECS	RO2850000
Autoignition Temperature	480 °C
TSCA	Yes
HazardClass	6.1(b)
PackingGroup	III
HS Code	29171190

Raw materials And Preparation Products

Hazard Information

Description

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

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/SiO₂to 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).

Material Safety Data Sheet(MSDS)

Spectrum Detail

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