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Merck
CN

247537

Oxalic acid dihydrate

ACS reagent grade, ≥99%, 99.5-102.5% (ACS specification), solid

Synonym(s):

Ethanedioic acid dihydrate

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About This Item

Linear Formula:
HO2CCO2H · 2H2O
CAS Number:
6153-56-6
Molecular Weight:
126.07
NACRES:
NA.21
PubChem Substance ID:
24854873
eCl@ss:
39021701
UNSPSC Code:
12352100
EC Number:
205-634-3
MDL number:
MFCD00149102
Beilstein/REAXYS Number:
3679436

Key Documents

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Product Name

Oxalic acid dihydrate, ACS reagent, ≥99%

InChI key

GEVPUGOOGXGPIO-UHFFFAOYSA-N

InChI

1S/C2H2O4.2H2O/c3-1(4)2(5)6;;/h(H,3,4)(H,5,6);2*1H2

SMILES string

[H]O[H].[H]O[H].OC(=O)C(O)=O

grade

ACS reagent

vapor density

4.4 (vs air)

vapor pressure

<0.01 mmHg ( 20 °C)

assay

≥99%
99.5-102.5% (ACS specification)

form

solid

impurities

H2SO4, passes test (darkened)
≤0.001% N compounds
≤0.005% insolubles

ign. residue

≤0.01%

Quality Level

200

pH

1.5 (10 g/L)

mp

104-106 °C (lit.)

solubility

water: 100 g/L at 25 °C

anion traces

chloride (Cl-): ≤0.002%
sulfate (SO42-): ≤0.005%

cation traces

Ca: ≤0.001%
Fe: ≤2 ppm
heavy metals: ≤5 ppm (by ICP-OES)

functional group

carboxylic acid

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Application

Oxalic acid dihydrate may be used:
  • As a catalyst in the preparation of tetrahydroquinoline derivatives via imino Diels-Alder reaction.
  • As a homogeneous catalyst in the preparation of highly functionalized piperidines via multi-component reaction.
  • As an oxidant for the formation of triazolinediones from corresponding urazoles and bisurazoles via oxidation.
  • In the transformation of thiols to nitrosothiols by reacting with sodium nitrite.

General description

Oxalic acid dihydrate is a promising candidate as a phase change material (PCM) for use in thermal energy storage (TES) technology due to its high heat of fusion and energy storage density/price ratio in comparison to other salt hydrates PCMs.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk

WGK 1

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ3129
BCCM6146
MKCV2338
MKCT6410
MKCV0055

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Effects of sodium chloride on the thermal behavior of oxalic acid dihydrate for thermal energy storage
Han L, et al
Applied Energy, 185, 762-767 (2017)
A Convenient Method for the Oxidation of Urazoles to Their Corresponding Triazolinediones Under Mild and Heterogeneous Conditions with Sodium Nitrite and Oxalic Dihydrate.
Zolfigolo MA and Mallakpour SE.
Synthetic Communications, 29(22), 4061-4069 (1999)
One-pot five-component synthesis of highly functionalized piperidines using oxalic acid dihydrate as a homogenous catalyst.
Sajadikhah SS, et al.
Chinese Chemical Letters = Zhongguo Hua Xue Kuai Bao, 23(5), 569-572 (2012)
An Efficient Method for Production and Storage of Unstable S-Nitrosothiols Under Mild and Heterogeneous Condition with Sodium Nitrite and Oxalic Acid Dihydrate.
Zolfigol MA, et al.
Synthetic Communications, 29(13), 2277-2280 (1999)
Imino Diels-Alder reactions catalyzed by oxalic acid dihydrate. Synthesis of Tetrahydroquinoline derivatives.
Nagarajan R and Perumal PT.
Synthetic Communications, 31(11), 1733-1736 (2001)
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