Sodium oxalate: Difference between revisions

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	==Preparation==		==Preparation==
	Sodium oxalate can be prepared through the ] of ] with ] (NaOH) in a 1:2 ]-to-] ] ratio. ] yields the ] oxalate<ref name=foote>{{cite journal \| doi = 10.2475/ajs.s5-26.151.16 }}</ref> that can be thoroughly dried by heating to between 200 and 250 °C.<ref name=yoshi/>		Sodium oxalate can be prepared through the ] of ] with ] (NaOH) in a 1:2 ]-to-] ] ratio. ] yields the ] oxalate<ref name=foote>{{cite journal \| doi = 10.2475/ajs.s5-26.151.16 \| title = The system; sodium iodate, sodium oxalate, water \| date = 1933 \| last1 = Foote \| first1 = H. W. \| last2 = Vance \| first2 = J. E. \| journal = American Journal of Science \| volume = 26 \| issue = 151 \| pages = 16–18 \| bibcode = 1933AmJS...26...16F }}</ref> that can be thoroughly dried by heating to between 200 and 250 °C.<ref name=yoshi/>

	Half-neutralization can be accomplished with NaOH in a 1:1 ratio which produces {{chem2\|NaHC2O4}}, ] sodium oxalate or ].		Half-neutralization can be accomplished with NaOH in a 1:1 ratio which produces {{chem2\|NaHC2O4}}, ] sodium oxalate or ].
Line 72:		Line 72:

	==Reactions==		==Reactions==
	Sodium oxalate starts to decompose above 290 °C into ] and ]:<ref name=yoshi>{{cite journal \| doi = 10.1016/0039-9140(78)80158-1 }}</ref>		Sodium oxalate starts to decompose above 290 °C into ] and ]:<ref name=yoshi>{{cite journal \| doi = 10.1016/0039-9140(78)80158-1 \| title = Investigation on the drying and decomposition of sodium oxalate \| date = 1978 \| last1 = Yoshimori \| first1 = T. \| journal = Talanta \| volume = 25 \| issue = 10 \| pages = 603–605 }}</ref>

	:{{chem2\|Na2C2O4 → Na2CO3 + CO}}		:{{chem2\|Na2C2O4 → Na2CO3 + CO}}

	When heated at between 200 and 525°C with ] in a 1:2 molar ratio, the above reaction is suppressed, yielding instead a ] with release of ]<ref name=balli>{{cite journal \| doi = 10.1016/0040-6031(94)80061-8 }}</ref>		When heated at between 200 and 525°C with ] in a 1:2 molar ratio, the above reaction is suppressed, yielding instead a ] with release of ]<ref name=balli>{{cite journal \| doi = 10.1016/0040-6031(94)80061-8 \| title = Thermal decomposition of sodium oxalate in the presence of V2O5 \| date = 1994 \| last1 = Ballivet-Tkatchenko \| first1 = D. \| last2 = Galy \| first2 = J. \| last3 = Parize \| first3 = J.-L. \| last4 = Savariault \| first4 = J.-M. \| journal = Thermochimica Acta \| volume = 232 \| issue = 2 \| pages = 215–223 }}</ref>

	:{{chem2\|''x'' Na2C2O4 + 2 V2O5 → 2 Na_{''x''}V2O5 + 2''x'' CO2}}		:{{chem2\|''x'' Na2C2O4 + 2 V2O5 → 2 Na_{''x''}V2O5 + 2''x'' CO2}}

Latest revision as of 15:33, 25 October 2024

Sodium oxalate
Names

Preferred IUPAC name Disodium oxalate
Other names Oxalic acid, disodium salt Sodium ethanedioate
Identifiers
CAS Number	62-76-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:132764
ChEMBL	ChEMBL182928
ChemSpider	5895
ECHA InfoCard	100.000.501
EC Number	200-550-3
PubChem CID	6125
RTECS number	K11750000
UNII	7U0V68LT9X
CompTox Dashboard (EPA)	DTXSID1037018
InChI InChI=1S/C2H2O4.2Na/c3-1(4)2(5)6;;/h(H,3,4)(H,5,6);;/q;2*+1/p-2Key: ZNCPFRVNHGOPAG-UHFFFAOYSA-L
SMILES C(=O)(C(=O))..
Properties
Chemical formula	Na₂C₂O₄
Molar mass	133.998 g·mol
Appearance	White crystalline solid
Odor	Odorless
Density	2.34 g/cm
Melting point	260 °C (500 °F; 533 K) decomposes above 290 °C
Solubility in water	2.69 g/(100 mL) (0 °C) 3.7 g/(100 mL) (20 °C) 6.25 g/(100 mL) (100 °C)
Solubility	Soluble in formic acid, insoluble in ethanol, diethyl ether
Structure
Crystal structure	monoclinic
Thermochemistry
Std enthalpy of formation (Δ_fH₂₉₈)	−1318 kJ/mol
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312
Precautionary statements	P280, P301+P312, P302+P352
NFPA 704 (fire diamond)	1 0 0
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	11160 mg/kg (oral, rat)
Safety data sheet (SDS)	Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Sodium oxalate, or disodium oxalate, is a chemical compound with the chemical formula Na₂C₂O₄. It is the sodium salt of oxalic acid. It contains sodium cations Na and oxalate anions C₂O2−4. It is a white, crystalline, odorless solid, that decomposes above 290 °C.

Sodium oxalate can act as a reducing agent, and it may be used as a primary standard for standardizing potassium permanganate (KMnO₄) solutions.

The mineral form of sodium oxalate is natroxalate. It is only very rarely found and restricted to extremely sodic conditions of ultra-alkaline pegmatites.

Preparation

Sodium oxalate can be prepared through the neutralization of oxalic acid with sodium hydroxide (NaOH) in a 1:2 acid-to-base molar ratio. Evaporation yields the anhydrous oxalate that can be thoroughly dried by heating to between 200 and 250 °C.

Half-neutralization can be accomplished with NaOH in a 1:1 ratio which produces NaHC₂O₄, monobasic sodium oxalate or sodium hydrogenoxalate.

Alternatively, it can be produced by decomposing sodium formate by heating it at a temperature exceeding 360 °C.

Reactions

Sodium oxalate starts to decompose above 290 °C into sodium carbonate and carbon monoxide:

Na₂C₂O₄ → Na₂CO₃ + CO

When heated at between 200 and 525°C with vanadium pentoxide in a 1:2 molar ratio, the above reaction is suppressed, yielding instead a sodium vanadium oxibronze with release of carbon dioxide

x Na₂C₂O₄ + 2 V₂O₅ → 2 Na_xV₂O₅ + 2x CO₂

with x increasing up to 1 as the temperature increases.

Sodium oxalate is used to standardize potassium permanganate solutions. It is desirable that the temperature of the titration mixture be greater than 60 °C to ensure that all the permanganate added reacts quickly. The kinetics of the reaction are complex, and the manganese(II) ions (Mn) formed catalyze the further reaction between permanganate and oxalic acid (formed in situ by the addition of excess sulfuric acid). The final equation is as follows:

5 Na₂C₂O₄ + 2 KMnO₄ + 8 H₂SO₄ → K₂SO₄ + 5 Na₂SO₄ + 2 MnSO₄ + 10 CO₂ + 8 H₂O

Biological activity

Like several other oxalates, sodium oxalate is toxic to humans. It can cause burning pain in the mouth, throat and stomach, bloody vomiting, headache, muscle cramps, cramps and convulsions, drop in blood pressure, heart failure, shock, coma, and possible death. Mean lethal dose by ingestion of oxalates is 10-15 grams/kilogram of body weight (per MSDS).

Sodium oxalate, like citrates, can also be used to remove calcium ions (Ca) from blood plasma. It also prevents blood from clotting. Note that by removing calcium ions from the blood, sodium oxalate can impair brain function, and deposit calcium oxalate in the kidneys.

References

^ "ChemIDplus - 62-76-0 - ZNCPFRVNHGOPAG-UHFFFAOYSA-L - Disodium oxalate - Similar structures search, synonyms, formulas, resource links, and other chemical information". chem.nlm.nih.gov. NIH. Retrieved 7 January 2019.
^ Yoshimori, T. (1978). "Investigation on the drying and decomposition of sodium oxalate". Talanta. 25 (10): 603–605. doi:10.1016/0039-9140(78)80158-1.
GHS: GESTIS 570199
"Natroxolate" (PDF). RRUFF. Mineral Data Publishing. Retrieved 7 January 2019.
Foote, H. W.; Vance, J. E. (1933). "The system; sodium iodate, sodium oxalate, water". American Journal of Science. 26 (151): 16–18. Bibcode:1933AmJS...26...16F. doi:10.2475/ajs.s5-26.151.16.
Ballivet-Tkatchenko, D.; Galy, J.; Parize, J.-L.; Savariault, J.-M. (1994). "Thermal decomposition of sodium oxalate in the presence of V2O5". Thermochimica Acta. 232 (2): 215–223. doi:10.1016/0040-6031(94)80061-8.
Mcbride, R. S. (1912). "The standardization of potassium permanganate solution by sodium oxalate". J. Am. Chem. Soc. 34 (4): 393–416. doi:10.1021/ja02205a009.

Sodium compounds

Inorganic

Halides	NaF NaHF₂ NaCl NaBr NaI NaAt
Chalcogenides	NaO₃ NaO₂ Na₂O Na₂O₂ NaOH NaOD Na₂S NaSH Na₂Se NaSeH Na₂Te NaHTe Na₂Po
Pnictogenides	Na₃N NaN₃ NaNH₂ Na₃P Na₃As
Oxyhalides	NaClO NaClO₂ NaClO₃ NaClO₄ NaBrO NaBrO₂ NaBrO₃ NaBrO₄ NaIO NaIO₃ NaIO₄
Oxychalcogenides	Na₂SO₃ Na₂SO₄ NaHSO₃ NaHSO₄ Na₂S₂O₃ Na₂S₂O₄ Na₂S₂O₅ Na₂S₂O₆ Na₂S₂O₇ Na₂S₂O₈ Na₂SeO₃ Na₂SeO₄ NaHSeO₃ Na₂TeO₃
Oxypnictogenides	NaNO₂ NaNO₃ Na₂N₂O₂ NaH₂PO₄ NaPO₂H₂ Na₂HPO₃ Na₂PO₃F Na₃PS₂O₂ Na₃PO₄ Na₅P₃O₁₀ Na₄P₂O₇ Na₂H₂P₂O₇ Na₃AsO₃ Na₃AsO₄ Na₂HAsO₄ NaH₂AsO₄ NaSbO₃
Others	NaAlH₄ NaAlO₂ Na₃AlF₆ NaAl(SO₄)₂ NaAuCl₄ NaSbF₆ NaAsF₆ Na₂TiF₆ NaBH₄ NaBH₃(CN) NaBO₂ Na₂B₄O₇ Na₂B₂O₉ Na₂B₈O₁₃ NaBiO₃ NaCN NaCNO NaCoO₂ NaH NaHCO₃ Na₄XeO₆ NaHXeO₄ NaMnO₄ NaOCN NaReO₄ NaSCN NaTcO₃ NaTcO₄ NaVO₃ Na₂CO₃ Na₂C₂O₄ Na₂C₃S₅ Na₂CrO₄ Na₂Cr₂O₇ Na₂Cr₃O₁₀ Na₂GeO₃ Na₂He Na₂ Na₂MnO₄ Na₂MoO₄ Na₃IrCl₆ Na₂PtCl₆ Na₂O(UO₃)₂ Na₂S₄O₆ Na₂SiO₃ Na₂TiO₃ Na₂U₂O₇ Na₂WO₄ Na₂Zn(OH)₄ Na₃VO₄ Na₆V₁₀O₂₈ Na₄Fe(CN)₆ Na₃Fe(CN)₆ Na₃Fe(C₂O₄)₃ Na₄SiO₄ Na₂SiF₆ Na₃[Co(NO₂)₆] NaNSi₂(CH₃)₆ Na₂PdCl₄

Organic

Compounds of the oxalate ion

(H₂C₂O₄)

Li₂C₂O₄

BeC₂O₄

+BO₃

+CO₃

(NH₄)₂C₂O₄
+NO₃

Na₂C₂O₄
NaHC₂O₄

MgC₂O₄

+PO₄
+PO₃

+SO₄

+Cl

K₂C₂O₄
KHC₂O₄

CaC₂O₄

CrC₂O₄

MnC₂O₄

FeC₂O₄
Fe₂(C₂O₄)₃
+Fe
humboldtine
+NH₄ +Na +K +K

CoC₂O₄

-Ni

CuC₂O₄

Katsarosite

Ga₂(C₂O₄)₃

Rb₂C₂O₄

SrC₂O₄

Y₂(C₂O₄)₃

Nb(HC₂O₄)₅

Ag₂C₂O₄

CdC₂O₄

In₂(C₂O₄)₃

SnC₂O₄

Cs₂C₂O₄

BaC₂O₄

Lu₂(C₂O₄)₃

-Pt

PbC₂O₄

La₂(C₂O₄)₃

Ce₂(C₂O₄)₃

Pr₂(C₂O₄)₃

Nd₂(C₂O₄)₃

Pm₂(C₂O₄)₃

Sm₂(C₂O₄)₃

Eu₂(C₂O₄)₃

Gd₂(C₂O₄)₃

Tb₂(C₂O₄)₃

Dy₂(C₂O₄)₃

Ho₂(C₂O₄)₃

Er₂(C₂O₄)₃

Tm₂(C₂O₄)₃

Yb₂(C₂O₄)₃

Ac₂(C₂O₄)₃

Th(C₂O₄)₂

UO₂C₂O₄

Np(C₂O₄)₂

Pu(C₂O₄)₂

Cm₂(C₂O₄)₃

Bk₂(C₂O₄)₃

Cf₂(C₂O₄)₃

Es₂(C₂O₄)₃

Categories:

Revision as of 15:33, 25 October 2024 editMarbletan (talk \| contribs)Extended confirmed users5,416 edits prep for cite bot← Previous edit		Latest revision as of 15:33, 25 October 2024 edit undoCitation bot (talk \| contribs)Bots5,428,609 edits Add: bibcode, pages, issue, volume, journal, date, title, authors 1-4. Upgrade ISBN10 to 13. \| Use this bot. Report bugs. \| Suggested by Marbletan \| #UCB_toolbar
Line 65:		Line 65:

	==Preparation==		==Preparation==
	Sodium oxalate can be prepared through the ] of ] with ] (NaOH) in a 1:2 ]-to-] ] ratio. ] yields the ] oxalate<ref name=foote>{{cite journal \| doi = 10.2475/ajs.s5-26.151.16 }}</ref> that can be thoroughly dried by heating to between 200 and 250 °C.<ref name=yoshi/>		Sodium oxalate can be prepared through the ] of ] with ] (NaOH) in a 1:2 ]-to-] ] ratio. ] yields the ] oxalate<ref name=foote>{{cite journal \| doi = 10.2475/ajs.s5-26.151.16 \| title = The system; sodium iodate, sodium oxalate, water \| date = 1933 \| last1 = Foote \| first1 = H. W. \| last2 = Vance \| first2 = J. E. \| journal = American Journal of Science \| volume = 26 \| issue = 151 \| pages = 16–18 \| bibcode = 1933AmJS...26...16F }}</ref> that can be thoroughly dried by heating to between 200 and 250 °C.<ref name=yoshi/>

	Half-neutralization can be accomplished with NaOH in a 1:1 ratio which produces {{chem2\|NaHC2O4}}, ] sodium oxalate or ].		Half-neutralization can be accomplished with NaOH in a 1:1 ratio which produces {{chem2\|NaHC2O4}}, ] sodium oxalate or ].
Line 72:		Line 72:

	==Reactions==		==Reactions==
	Sodium oxalate starts to decompose above 290 °C into ] and ]:<ref name=yoshi>{{cite journal \| doi = 10.1016/0039-9140(78)80158-1 }}</ref>		Sodium oxalate starts to decompose above 290 °C into ] and ]:<ref name=yoshi>{{cite journal \| doi = 10.1016/0039-9140(78)80158-1 \| title = Investigation on the drying and decomposition of sodium oxalate \| date = 1978 \| last1 = Yoshimori \| first1 = T. \| journal = Talanta \| volume = 25 \| issue = 10 \| pages = 603–605 }}</ref>

	:{{chem2\|Na2C2O4 → Na2CO3 + CO}}		:{{chem2\|Na2C2O4 → Na2CO3 + CO}}

	When heated at between 200 and 525°C with ] in a 1:2 molar ratio, the above reaction is suppressed, yielding instead a ] with release of ]<ref name=balli>{{cite journal \| doi = 10.1016/0040-6031(94)80061-8 }}</ref>		When heated at between 200 and 525°C with ] in a 1:2 molar ratio, the above reaction is suppressed, yielding instead a ] with release of ]<ref name=balli>{{cite journal \| doi = 10.1016/0040-6031(94)80061-8 \| title = Thermal decomposition of sodium oxalate in the presence of V2O5 \| date = 1994 \| last1 = Ballivet-Tkatchenko \| first1 = D. \| last2 = Galy \| first2 = J. \| last3 = Parize \| first3 = J.-L. \| last4 = Savariault \| first4 = J.-M. \| journal = Thermochimica Acta \| volume = 232 \| issue = 2 \| pages = 215–223 }}</ref>

	:{{chem2\|''x'' Na2C2O4 + 2 V2O5 → 2 Na_{''x''}V2O5 + 2''x'' CO2}}		:{{chem2\|''x'' Na2C2O4 + 2 V2O5 → 2 Na_{''x''}V2O5 + 2''x'' CO2}}