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{{chembox |
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{{chembox |
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| verifiedrevid = 265178458 |
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|verifiedrevid = 408853766 |
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| Name = Disodium oxalate |
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| ImageFile = Sodium-oxalate-2D.png |
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|Name = Sodium oxalate |
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|ImageFile = Sodium-oxalate-2D.png |
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|ImageName = Disodium oxalate |
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<!-- | ImageSize = 200px --> |
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| ImageName = Disodium oxalate |
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|PIN = Disodium oxalate |
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| OtherNames = Oxalic acid, disodium salt<br />Sodium ethanedioate |
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|OtherNames = Oxalic acid, disodium salt<br />Sodium ethanedioate |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 62-76-0 |
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|CASNo = 62-76-0 |
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|CASNo_Ref = {{cascite|correct|CAS}}<ref name="ChemIDplus">{{cite web |title=ChemIDplus - 62-76-0 - ZNCPFRVNHGOPAG-UHFFFAOYSA-L - Disodium oxalate - Similar structures search, synonyms, formulas, resource links, and other chemical information. |url=https://chem.nlm.nih.gov/chemidplus/rn/62-76-0 |website=chem.nlm.nih.gov |publisher=NIH |access-date=7 January 2019 |language=en}}</ref> |
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| CASNo_Ref = {{cascite}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 6125 |
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|UNII = 7U0V68LT9X |
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| RTECS = K11750000 |
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|PubChem = 6125 |
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}} |
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|ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| Section2 = {{Chembox Properties |
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|ChEMBL = 182928 |
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| Formula = Na<sub>2</sub>C<sub>2</sub>O<sub>4</sub> |
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|ChEBI_Ref = {{ebicite|changed|EBI}} |
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| MolarMass = 133.99914 g/mol |
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|ChEBI = 132764 |
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| Density = 2.34 g/cm<sup>3</sup> |
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|RTECS = K11750000 |
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| Solubility = 3.7 g/100 ml (20 °C) <br> 6.25 g/100 mL (100 °C) |
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|EINECS = 200-550-3 |
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| SolubleOther = insoluble in ] |
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|SMILES = C(=O)(C(=O)).. |
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| MeltingPoint = 260 °C (decomp) |
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|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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|ChemSpiderID = 5895 |
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|StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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|StdInChI = 1S/C2H2O4.2Na/c3-1(4)2(5)6;;/h(H,3,4)(H,5,6);;/q;2*+1/p-2 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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|StdInChIKey = ZNCPFRVNHGOPAG-UHFFFAOYSA-L |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section2={{Chembox Properties |
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|Formula = {{chem2|Na2C2O4}} |
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| ExternalMSDS = |
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|Na=2|C=2|O=4 |
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| EUClass = {{Hazchem Xn}} |
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|Appearance = White crystalline solid |
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| NFPA-H = 3 |
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|Odor = Odorless |
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| NFPA-F = 0 |
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|Density = 2.34 g/cm<sup>3</sup> |
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| NFPA-R = 0 |
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|Solubility = {{ubl|2.69 g/(100 mL) (0 °C)|3.7 g/(100 mL) (20 °C)|6.25 g/(100 mL) (100 °C)}} |
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| NFPA-O = |
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|SolubleOther = Soluble in ], insoluble in ], ] |
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|MeltingPtC = 260 |
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|MeltingPt_notes = decomposes above 290 °C<ref name=yoshi/> |
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|Section3={{Chembox Structure |
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'''Disodium oxalate''', often called simply '''sodium oxalate''', is a ] salt of ] with the molecular formula Na<sub>2</sub>C<sub>2</sub>O<sub>4</sub>. It is usually a white, crystalline, odorless powder, that decomposes at 250–270 ]. |
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|CrystalStruct = monoclinic |
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|Section4={{Chembox Thermochemistry |
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|DeltaHf = −1318 kJ/mol |
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|Section7={{Chembox Hazards |
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| ExternalSDS = {{Unreliable source|sure=y|reason=The webpage has been deprecated and is advising users to not use it as a reference.|date=May 2020}} |
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|GHSPictograms = {{GHS07}} |
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|GHSSignalWord = warning |
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|HPhrases = {{HPhrases|H302|H312}} |
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|PPhrases = {{PPhrases|P280|P302+P352|P301+P312}} |
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|GHS_ref = <ref>GHS: </ref> |
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|NFPA-H = 1 |
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|NFPA-F = 0 |
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|NFPA-R = 0 |
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|LD50 = 11160 mg/kg (oral, rat)<ref name="ChemIDplus" /> |
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'''Sodium oxalate''', or '''disodium oxalate''', is a ] with the ] {{chem2|Na2C2O4|auto=1}}. It is the ] ] of ]. It contains sodium ] {{chem2|Na+}} and ] ] {{chem2|C2O4(2−)}}. It is a white, crystalline, odorless solid, that decomposes above 290 ].<ref name=yoshi/> |
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Disodium oxalate can act as a ], and it may be used as a ] for standardizing ] (KMnO<sub>4</sub>) solutions. |
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Sodium oxalate can act as a ], and it may be used as a ] for standardizing ] ({{chem2|KMnO4}}) solutions. |
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The ] form of sodium oxalate is ]. It is only very rarely found and restricted to extremely sodic conditions of ultra-alkaline ]s.<ref>http://rruff.geo.arizona.edu/doclib/hom/natroxalate.pdf Handbook of Mineralogy</ref> |
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The ] form of sodium oxalate is ]. It is only very rarely found and restricted to extremely ] of ultra-] ]s.<ref name="RRUFF">{{cite web |title=Natroxolate |url=http://rruff.geo.arizona.edu/doclib/hom/natroxalate.pdf |website=RRUFF |publisher=Mineral Data Publishing |access-date=7 January 2019}}</ref> |
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==Preparation== |
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==Preparation== |
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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/> |
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Sodium oxalate can be prepared through the neutralization of oxalic acid with NaOH in a 1:2 acid-to-base molar ratio. Half-neutralization can be accomplished with NaOH in a 1:1 ratio which produces NaHC<sub>2</sub>O<sub>4</sub>, monobasic sodium oxalate or sodium ]. |
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Half-neutralization can be accomplished with NaOH in a 1:1 ratio which produces {{chem2|NaHC2O4}}, ] sodium oxalate or ]. |
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Alternatively, it can be produced by decomposing ] by heating it at a temperature exceeding 360 °C.{{citation needed|date=April 2017}} |
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==Reactions== |
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==Reactions== |
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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> |
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Sodium oxalate is used to standardize ] solutions. It is desirable that the temperature of the titration mixture is greater than 60 °C to ensure that all the permanganate added reacts quickly. The kinetics of the reaction is complex, and the manganate(II) ions 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:<ref>{{cite journal | doi = 10.1021/ja02205a009 | year = 1912 | author = Mcbride, R. S. | journal = ] | title = The standardization of potassium permanganate solution by sodium oxalate | volume = 34 | pages = 393}}</ref> |
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:{{chem2|Na2C2O4 → Na2CO3 + CO}} |
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: 5H<sub>2</sub>C<sub>2</sub>O<sub>4</sub> + 2KMnO<sub>4</sub> + 3H<sub>2</sub>SO<sub>4</sub> → K<sub>2</sub>SO<sub>4</sub> + 2MnSO<sub>4</sub> + 10CO<sub>2</sub> + 8H<sub>2</sub>O |
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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> |
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:{{chem2|''x'' Na2C2O4 + 2 V2O5 → 2 Na_{''x''}V2O5 + 2''x'' CO2}} |
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with ''x'' increasing up to 1 as the temperature increases. |
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Sodium oxalate is used to standardize ] solutions. It is desirable that the temperature of the ] mixture be greater than 60 °C to ensure that all the permanganate added reacts quickly. The ] are complex, and the ](II) ] ({{chem2|Mn(2+)}}) formed ] the further reaction between permanganate and oxalic acid (formed ''in situ'' by the addition of excess ]). The final equation is as follows:<ref>{{cite journal | doi = 10.1021/ja02205a009 | year = 1912 | author = Mcbride, R. S. | journal = ] | title = The standardization of potassium permanganate solution by sodium oxalate | volume = 34 | issue = 4 | pages = 393–416| url = https://zenodo.org/record/1429003}}</ref> |
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:{{chem2|5 Na2C2O4 + 2 KMnO4 + 8 H2SO4 → ] + 5 ] + 2 ] + 10 CO2 + 8 H2O}} |
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==Biological activity== |
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==Biological activity== |
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Like several other ]s, 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 (per ]). |
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Like several other ]s, 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 ]). |
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Sodium oxalate, like ]s, can also be used to remove calcium ions (Ca<sup>2+</sup>) 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. |
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Sodium oxalate, like ]s, can also be used to remove ] ] ({{chem2|Ca(2+)}}) from ]. It also prevents blood from ]. Note that by removing calcium ions from the ], sodium oxalate can impair ] function, and deposit ] in the ]. |
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==References== |
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==References== |
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{{Sodium compounds}} |
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{{Sodium compounds}} |
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{{Oxalates}} |
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