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Sodium formate, HCOONa, is the sodium salt of
formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Es ...
, HCOOH. It usually appears as a white deliquescent powder.


Preparation

For commercial use, sodium formate is produced by absorbing carbon monoxide under pressure in solid
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...
at 130 °C and 6-8 bar pressure:Arnold Willmes, ''Taschenbuch Chemische Substanzen'', Harri Deutsch, Frankfurt (M.), 2007. :CO + NaOH → HCO2Na Because of the low-cost and large-scale availability of
formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Es ...
by carbonylation of methanol and hydrolysis of the resulting methyl formate, sodium formate is usually prepared by neutralizing formic acid with
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...
. Sodium formate is also unavoidably formed as a by-product in the final step of the pentaerythritol synthesis and in the crossed Cannizzaro reaction of formaldehyde with the aldol reaction product trimethylol acetaldehyde -hydroxy-2,2-bis(hydroxymethyl)propanal In the laboratory, sodium formate can be prepared by neutralizing
formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Es ...
with
sodium carbonate Sodium carbonate, , (also known as washing soda, soda ash and soda crystals) is the inorganic compound with the formula Na2CO3 and its various hydrates. All forms are white, odourless, water-soluble salts that yield moderately alkaline solutions ...
. It can also be obtained by reacting
chloroform Chloroform, or trichloromethane, is an organic compound with chemical formula, formula Carbon, CHydrogen, HChlorine, Cl3 and a common organic solvent. It is a colorless, strong-smelling, dense liquid produced on a large scale as a precursor to ...
with an alcoholic solution of
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...
. ::CHCl3 + 4 NaOH → HCOONa + 3 NaCl + 2 H2O or by reacting
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...
with chloral hydrate. ::C2HCl3(OH)2 + NaOH → CHCl3 + HCOONa + H2O The latter method is, in general, preferred to the former because the low aqueous solubility of CHCl3 makes it easier to separate out from the sodium formate solution, by
fractional crystallization Fractional crystallization may refer to: * Fractional crystallization (chemistry), a process to separate different solutes from a solution * Fractional crystallization (geology) Fractional crystallization, or crystal fractionation, is one of the ...
, than the soluble NaCl would be. Sodium formate may also be created via the haloform reaction between ethanol and sodium hypochlorite in the presence of a base. This procedure is well documented for the preparation of
chloroform Chloroform, or trichloromethane, is an organic compound with chemical formula, formula Carbon, CHydrogen, HChlorine, Cl3 and a common organic solvent. It is a colorless, strong-smelling, dense liquid produced on a large scale as a precursor to ...
.


Properties


Physical properties

Sodium formate crystallizes in a monoclinic crystal system with the lattice parameters a = 6,19 Å, b = 6,72 Å, c = 6,49 Å and β = 121,7°.W. H. Zachariasen: "The Crystal Structure of Sodium Formate, NaHCO2" in ''
J. Am. Chem. Soc. The ''Journal of the American Chemical Society'' is a weekly peer-reviewed scientific journal that was established in 1879 by the American Chemical Society. The journal has absorbed two other publications in its history, the ''Journal of Analytic ...
'', 1940, ''62''(5), S. 1011–1013.


Chemical properties

On heating, sodium formate decomposes to form sodium oxalate and hydrogen. The resulting sodium oxalate can be converted by further heating to
sodium carbonate Sodium carbonate, , (also known as washing soda, soda ash and soda crystals) is the inorganic compound with the formula Na2CO3 and its various hydrates. All forms are white, odourless, water-soluble salts that yield moderately alkaline solutions ...
upon release of carbon monoxide:T. Yoshimori, Y. Asano, Y. Toriumi, T. Shiota: "Investigation on the drying and decomposition of sodium oxalate" in ''
Talanta ''Talanta'' is a peer-reviewed scientific journal in pure and applied analytical chemistry. It was established in 1958 and is published by Elsevier, with 15 issues per year. In addition to original research articles, ''Talanta'' also publishes revi ...
'' 1978, ''25''(10) S. 603-605.
T. Meisel, Z. Halmos, K. Seybold, E. Pungor: "The thermal decomposition of alkali metal formates" in ''
Journal of Thermal Analysis and Calorimetry The ''Journal of Thermal Analysis and Calorimetry'' is a peer-reviewed scientific journal published by Springer Science+Business Media in cooperation with Akadémiai Kiadó. Formerly this journal was known as ''Journal of Thermal Analysis''. It ...
'' 1975, ''7''(1). S. 73-80.
:2HCOONa ->
Delta Delta commonly refers to: * Delta (letter) (Δ or δ), a letter of the Greek alphabet * River delta, at a river mouth * D (NATO phonetic alphabet: "Delta") * Delta Air Lines, US * Delta variant of SARS-CoV-2 that causes COVID-19 Delta may also re ...
+ H2\!\uparrow
:(COO)2Na2 -> \atop >\ \ce + CO\!\uparrow As a salt of a weak acid (
formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Es ...
) and a
strong base In chemistry, there are three definitions in common use of the word base, known as Arrhenius bases, Brønsted bases, and Lewis bases. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. Rou ...
(
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...
) sodium formate reacts in aqueous solutions basic: :HCOO^- + H2O <<=> HCOOH + OH^- A solution of formic acid and sodium formate can thus be used as a buffer 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 buffering agent for strong mineral acids to increase their pH, as a food additive (E237), and as a de-icing agent. In structural biology, sodium formate can be used as a cryoprotectant for X-ray diffraction experiments on protein crystals, which are typically conducted at a temperature of 100 K to reduce the effects of radiation damage. Sodium formate plays a role in the
synthesis Synthesis or synthesize may refer to: Science Chemistry and biochemistry *Chemical synthesis, the execution of chemical reactions to form a more complex molecule from chemical precursors ** Organic synthesis, the chemical synthesis of organ ...
of
formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Es ...
, it is converted by sulfuric acid via the following reaction equation: :\mathrm :Sodium formate is converted with sulfuric acid to formic acid and
sodium sulfate Sodium sulfate (also known as sodium sulphate or sulfate of soda) is the inorganic compound with formula Na2SO4 as well as several related hydrates. All forms are white solids that are highly soluble in water. With an annual production of 6 milli ...
.
The urticating hair of
stinging nettles ''Urtica dioica'', often known as common nettle, burn nettle, stinging nettle (although not all plants of this species sting) or nettle leaf, or just a nettle or stinger, is a herbaceous perennial flowering plant in the family Urticaceae. Ori ...
contain sodium formate as well as formic acid. Solid sodium formate is used as a non-corrosive agent at airports 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
Ottawa Ottawa (, ; Canadian French: ) is the capital city of Canada. It is located at the confluence of the Ottawa River and the Rideau River in the southern portion of the province of Ontario. Ottawa borders Gatineau, Quebec, and forms the core ...
from 1987 to 1988. The high freezing point depression e.g. in comparison to the still frequently used urea (which is effective but problematic due to eutrophication) effectively prevents the re-icing, even at temperatures below −15 °C. The thawing effect of the solid sodium formate can even be increased by moistening with aqueous potassium formate or potassium acetate solutions. The degradability of sodium formate is particularly advantageous with a chemical oxygen demand (COD) of 211 mg O2/g compared with the de-icing agents sodium acetate (740 mg O2/g) and urea with (> 2,000 mg O2/g). 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 oil exploration because of their relatively high density. By mixing the corresponding saturated alkali metal formate solutions any densities between 1,0 and 2,3 g/cm3 can be set. The saturated solutions are biocidal and long-term stable 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
baryte Baryte, barite or barytes ( or ) is a mineral consisting of barium sulfate ( Ba S O4). Baryte is generally white or colorless, and is the main source of the element barium. The ''baryte group'' consists of baryte, celestine (strontium sulfate), ...
s) and the formate solutions can be recovered and
recycled Recycling is the process of converting waste materials into new materials and objects. The recovery of energy from waste materials is often included in this concept. The recyclability of a material depends on its ability to reacquire the p ...
at the drilling site, formates represent an important advance in exploration technology.William Benton and Jim Turner, Cabot Specialty Fluids
Cesium formate fluid succeeds in North Sea HPHT field trials
(PDF; 88 kB); In: Drilling Contractor, Mai/Juni 2000.


See also

* Sodium acetate


References

{{Authority control Formates Organic sodium salts Deliquescent substances