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{{short description|Chemical compound}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 402671953
| Watchedfields = changed
| Name = Sodium formate
| verifiedrevid = 422111969
| Name = Sodium formate
| ImageFile = Sodium-formate-2D.png | ImageFile = Sodium-formate-2D.png
| ImageSize = 200px
| ImageName = Structural formula of sodium formate | ImageName = Structural formula of sodium formate
| ImageSize = 125px
| ImageFileL1 = Formate-3D-balls.png | ImageFileL1 = Formate-3D-balls.png
| ImageSizeL1 = 110px
| ImageNameL1 = Ball-and-stick model of the formate anion | ImageNameL1 = Ball-and-stick model of the formate anion
| ImageFileR1 = Sodium-3D.png | ImageFileR1 = Sodium-3D.png
| SystematicName = Sodium methanoate
| ImageNameR1 = The sodium cation
| OtherNames = formic acid, sodium salt | OtherNames = {{Unbulleted list|formic acid, sodium salt}}
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 141-53-7
| ChEBI = 62965
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 183491
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8517 | ChemSpiderID = 8517
| EINECS = 205-488-0
| PubChem = 2723810
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 387AD98770 | UNII = 387AD98770
| InChI = 1/CH2O2.Na/c2-1-3;/h1H,(H,2,3);/q;+1/p-1 | InChI = 1/CH2O2.Na/c2-1-3;/h1H,(H,2,3);/q;+1/p-1
| InChIKey = HLBBKKJFGFRGMU-REWHXWOFAN | InChIKey = HLBBKKJFGFRGMU-REWHXWOFAN
| SMILES = .C=O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/CH2O2.Na/c2-1-3;/h1H,(H,2,3);/q;+1/p-1 | StdInChI = 1S/CH2O2.Na/c2-1-3;/h1H,(H,2,3);/q;+1/p-1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HLBBKKJFGFRGMU-UHFFFAOYSA-M | StdInChIKey = HLBBKKJFGFRGMU-UHFFFAOYSA-M
| SMILES = .C=O
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 141-53-7
| EINECS = 205-488-0
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = HCOONa | Formula = HCOONa
| MolarMass = 68.01 g/mol | MolarMass = 68.007 g/mol
| Appearance = white granules <br> ] | Appearance = white granules <br> ]
| Density = 1.92 g/cm<sup>3</sup> (20°C) | Density = 1.92 g/cm<sup>3</sup> (20 °C)
| Solubility = 97 g/100 mL (20°C) | Solubility = 43.82 g/100 mL (0 °C) <br> 97.2 g/100 mL (20 °C) <br> 160 g/100 mL (100 °C)
| SolubleOther = insoluble in ] <br> soluble in ], ] | SolubleOther = insoluble in ] <br> soluble in ], ], ]
| MeltingPt = 253 °C | MeltingPtC = 253
| BoilingPt = decomposes | BoilingPt = decomposes
}}
| pKa = 7.0-8.5 (0.1M)
| Section5 = {{Chembox Thermochemistry
| DeltaHf = -666.5 kJ/mol
| DeltaGf = -599.9 kJ/mol
| Entropy = 103.8 J/mol K
| HeatCapacity = 82.7 J/mol K
}} }}
| Section7 = {{Chembox Hazards | Section7 = {{Chembox Hazards

| EUClass = not listed
| NFPA-H = 1 | NFPA-H = 1
| NFPA-F = | NFPA-F = 0
| NFPA-R = | NFPA-R = 0
}} }}
}} }}


'''Sodium formate''', HCOONa, is the sodium salt of ], HCOOH. It usually appears as a white ] powder. '''Sodium formate''', HCOONa, is the sodium salt of ], HCOOH. It usually appears as a white ] powder.

==Uses==
Sodium formate is used in several fabric dyeing and printing processes. It is also used as a ] for strong mineral acids to increase their ], and as a food additive (E237).


==Preparation== ==Preparation==
For commercial use, sodium formate is produced by absorbing ] under pressure in solid ] at 130&nbsp;°C and 6-8 bar pressure:<ref name="TCS">Arnold Willmes, ''Taschenbuch Chemische Substanzen'', Harri Deutsch, Frankfurt (M.), 2007.</ref>
Sodium formate can be prepared in the laboratory by neutralizing ] with ]. It can also be obtained by reacting ] with an alcoholic solution of ].


::] + 4] → HCOONa + 3] + 2] :CO + NaOH → HCO<sub>2</sub>Na

Because of the low-cost and large-scale availability of ] by carbonylation of methanol and hydrolysis of the resulting methyl formate, sodium formate is usually prepared by ] formic acid with ]. Sodium formate is also unavoidably formed as a by-product in the final step of the ] synthesis and in the crossed ] of ] with the aldol reaction product trimethylol acetaldehyde .<ref>H.-J. Arpe, ''Industrielle Organische Chemie'', 6., vollst. überarb. Aufl., Wiley-VCH Verlag, 2007, {{ISBN|978-3-527-31540-6}}</ref>

In the laboratory, sodium formate can be prepared by neutralizing ] with ]. It can also be obtained by reacting ] with an alcoholic solution of ].

::CHCl<sub>3</sub> + 4 NaOH → HCOONa + 3 NaCl + 2 H<sub>2</sub>O


or by reacting ] with ]. or by reacting ] with ].


::] + ] → ] + HCOONa + ] ::C<sub>2</sub>HCl<sub>3</sub>(OH)<sub>2</sub> + NaOH → CHCl<sub>3</sub> + HCOONa + H<sub>2</sub>O


The latter method is, in general, preferred to the former because the low aqueous solubility of ] makes it easier to separate out from the sodium formate solution, by ], than the soluble ] would be. The latter method is, in general, preferred to the former because the low aqueous solubility of ] makes it easier to separate out from the sodium formate solution, by ], than the soluble ] would be.


== Properties ==
For commercial use, sodium formate is produced by absorbing ] under pressure in solid ] at 160 °C.
=== Physical properties ===
]
Sodium formate crystallizes in a ] with the ]s a&nbsp;=&nbsp;6,19&nbsp;Å, b&nbsp;=&nbsp;6,72&nbsp;Å, c&nbsp;=&nbsp;6,49&nbsp;Å and β&nbsp;=&nbsp;121,7°.<ref name="Zachariasen">W. H. Zachariasen: "The Crystal Structure of Sodium Formate, NaHCO<sub>2</sub>" in '']'', '''1940''', ''62''(5), S. 1011–1013. {{doi|10.1021/ja01862a007}}</ref>


=== Chemical properties ===
::] + ] → HCOONa
On heating, sodium formate decomposes to form ] and hydrogen.<ref name="Meisel" /> The resulting sodium oxalate can be converted by further heating to ] upon release of carbon monoxide:<ref name="Yoshimori">T. Yoshimori, Y. Asano, Y. Toriumi, T. Shiota: "Investigation on the drying and decomposition of sodium oxalate" in '']'' '''1978''', ''25''(10) S. 603-605. {{doi|10.1016/0039-9140(78)80158-1}}</ref><ref name="Meisel">T. Meisel, Z. Halmos, K. Seybold, E. Pungor: "The thermal decomposition of alkali metal formates" in '']'' '''1975''', ''7''(1). S. 73-80. {{doi|10.1007/BF01911627}}</ref>
:<chem>2HCOONa -> {(COO)2Na2} + H2\!\uparrow</chem>


:<chem>(COO)2Na2 -> {Na2CO3} + CO\!\uparrow</chem>
Sodium formate may also be created via the ] between ] and ] in the presence of a ]. This procedure is well documented for the preparation of ].

As a ] of a weak acid (]) and a ] (]) sodium formate reacts in aqueous solutions basic:

:<chem>HCOO^- + H2O <<=> HCOOH + OH^-</chem>

A solution of formic acid and sodium formate can thus be used as a ] solution.

Sodium formate is slightly water-hazardous and inhibits some species of bacteria but is degraded by others.

==Uses==
Sodium formate is used in several fabric dyeing and printing processes. It is also used as a ] for strong mineral acids to increase their ], as a food additive (E237), and as a ] agent.

In ], sodium formate can be used as a ] for X-ray diffraction experiments on protein crystals,<ref>{{citation | doi=10.1107/S0907444910015416 | first1=G. | last1=Bujacz | first2=B. | last2=Wrzesniewska | first3=A. | last3=Bujacz | title=Cryoprotection properties of salts of organic acids: a case study for a tetragonal crystal of HEW lysozyme | year=2010 | periodical=Acta Crystallographica Section D: Biological Crystallography | volume=66 | issue=7 | pages=789–796| pmid=20606259 }}</ref> which are typically conducted at a temperature of 100 K to reduce the effects of ].

Sodium formate plays a role in the ] of ], it is converted by sulfuric acid via the following reaction equation:

:<math>\mathrm{2\ HCOONa + H_2SO_4 \longrightarrow 2\ HCOOH + Na_2SO_4}</math>
:<small>Sodium formate is converted with sulfuric acid to formic acid and ].</small>

The ] of ] contain sodium formate as well as formic acid.

Solid sodium formate is used as a non-corrosive agent at ]s for de-icing of runways in mix with corrosion inhibitors and other additives, which rapidly penetrate solid snow and ice layers, detach them from the asphalt or concrete and melt the ice rapidly. Sodium formate was also used as a road deicer in the city of ] from 1987 to 1988.<ref>{{cite book|author=Frank M. D'Itri|url=https://books.google.com/books?id=NkGCKevsmpkC&q=Sodium+formate&pg=PA167|title=Chemical Deicers and the Environment|via=]|year=1992|isbn=9780873717052|page=167| publisher=CRC Press }}</ref>

The high freezing point depression e.g. in comparison to the still frequently used ] (which is effective but problematic due to ]) effectively prevents the re-icing, even at temperatures below −15&nbsp;°C. The thawing effect of the solid sodium formate can even be increased by moistening with aqueous ] or ] solutions. The degradability of sodium formate is particularly advantageous with a chemical oxygen demand (COD) of 211&nbsp;mg ]/g compared with the de-icing agents ] (740&nbsp;mg O<sub>2</sub>/g) and urea with (> 2,000&nbsp;mg O<sub>2</sub>/g).<ref>{{cite web |url=http://www.deicersnowmeltingthawing.com/ |title=Deicer Anti-icing Snow melting Thawing Chemicals Manufacturers |access-date=2022-03-02 |archive-date=2018-08-05 |archive-url=https://web.archive.org/web/20180805095557/http://deicersnowmeltingthawing.com/ |url-status=dead }}</ref>

Saturated sodium formate solutions (as well as mixtures of other alkali metal formates such as potassium and cesium formate) are used as important drilling and stabilizing aids in gas and ] because of their relatively high density. By mixing the corresponding saturated alkali metal formate solutions any densities between 1,0 and 2,3 g/cm<sup>3</sup> can be set. The saturated solutions are ] and ] against microbial degradation. Diluted, on the other hand, they are fast and completely biodegradable. As alkali metal formates as drilling aids make it unnecessary to add solid fillers to increase the density (such as ]s) and the formate solutions can be recovered and ] at the drilling site, formates represent an important advance in exploration technology.<ref>William Benton and Jim Turner, Cabot Specialty Fluids: (PDF; 88&nbsp;kB); In: Drilling Contractor, Mai/Juni 2000.</ref>


==See also== ==See also==
* ] * ]


==References== ==References==
{{Unreferenced|date=September 2007}}
<references/> <references/>

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