Sodium acetate

Sodium acetate
Names
	IUPAC name Sodium acetate
	Systematic IUPAC name Sodium ethanoate
	Other names Hot ice (sodium acetate trihydrate)
Identifiers
CAS Number	anhydrous: 127-09-3 ; trihydrate: 6131-90-4 ;
3D model (JSmol)	anhydrous: Interactive image;
Beilstein Reference	3595639
ChEBI	anhydrous: CHEBI:32954 ; trihydrate: CHEBI:32138;
ChEMBL	anhydrous: ChEMBL1354 ;
ChemSpider	anhydrous: 29105 ;
ECHA InfoCard	100.004.386
EC Number	anhydrous: 204-823-8;
E number	E262 (preservatives)
Gmelin Reference	20502
KEGG	trihydrate: D01779;
PubChem CID	anhydrous: 517045; trihydrate: 23665404;
RTECS number	anhydrous: AJ4300010 (anhydrous); AJ4580000;
UNII	anhydrous: NVG71ZZ7P0 ; trihydrate: 4550K0SC9B;
CompTox Dashboard (EPA)	anhydrous: DTXSID2027044 ;
	InChI InChI=1S/C2H4O2.Na/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1 Key: VMHLLURERBWHNL-UHFFFAOYSA-M ; anhydrous: InChI=1/C2H4O2.Na/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1 Key: VMHLLURERBWHNL-REWHXWOFAT;
	SMILES anhydrous: [Na+].[O-]C(=O)C;
Properties
Chemical formula	C2H3NaO2
Molar mass	82.034 g·mol−1
Appearance	White deliquescent powder
Odor	Vinegar (acetic acid) odor when heated to decomposition[1]
Density	1.528 g/cm3 (20 °C, anhydrous); 1.45 g/cm3 (20 °C, trihydrate)[2]
Melting point	324 °C (615 °F; 597 K) ; (anhydrous); 58 °C (136 °F; 331 K); (trihydrate)
Boiling point	881.4 °C (1,618.5 °F; 1,154.5 K) ; (anhydrous); 122 °C (252 °F; 395 K); (trihydrate) decomposes
Solubility in water	Anhydrous:; 119 g/100 mL (0 °C); 123.3 g/100 mL (20 °C); 125.5 g/100 mL (30 °C); 137.2 g/100 mL (60 °C); 162.9 g/100 mL (100 °C); Trihydrate:; 32.9 g/100 mL (-10 °C); 36.2 g/100 mL (0 °C); 46.4 g/100 mL (20 °C); 82 g/100 mL (50 °C)[3]
Solubility	Soluble in alcohol, hydrazine, SO2[4]
Solubility in methanol	16 g/100 g (15 °C); 16.55 g/100 g (67.7 °C)[4]
Solubility in ethanol	Trihydrate:; 5.3 g/100 mL
Solubility in acetone	0.5 g/kg (15 °C)[4]
Acidity (pKa)	24 (20 °C)[4]; 4.75 CH3COOH[5]
Basicity (pKb)	9.25
Magnetic susceptibility (χ)	−37.6·10−6 cm3/mol
Refractive index (nD)	1.464
Structure
Crystal structure	Monoclinic
Thermochemistry
Heat capacity (C)	100.83 J/mol·K (anhydrous)[6]; 229 J/mol·K (trihydrate)[7]
Std molar; entropy (So298)	138.1 J/mol·K (anhydrous)[6]; 262 J/mol·K (trihydrate)[2]
Std enthalpy of; formation (ΔfH⦵298)	−709.32 kJ/mol (anhydrous)[4]; −1604 kJ/mol (trihydrate)[2]
Gibbs free energy (ΔfG˚)	−607.7 kJ/mol (anhydrous)[4]
Pharmacology
ATC code	B05XA08 (WHO)
Hazards
Main hazards	Irritant
Safety data sheet	External MSDS
NFPA 704 (fire diamond)	1 1 0
Flash point	>250 °C (482 °F; 523 K) [5]
Autoignition; temperature	600 °C (1,112 °F; 873 K)[5]
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	3530 mg/kg (oral, rat)
Related compounds
Other anions	Sodium formate; Sodium propionate
Other cations	Potassium acetate; Calcium acetate
Related compounds	Sodium diacetate
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Sodium acetate, CH₃COONa, also abbreviated Na O Ac,[8] is the sodium salt of acetic acid. This colorless deliquescent salt has a wide range of uses.

Applications

Biotechnological

Sodium acetate is used as the carbon source for culturing bacteria. Sodium acetate is also useful for increasing yields of DNA isolation by ethanol precipitation.

Industrial

Sodium acetate is used in the textile industry to neutralize sulfuric acid waste streams and also as a photoresist while using aniline dyes. It is also a pickling agent in chrome tanning and helps to impede vulcanization of chloroprene in synthetic rubber production. In processing cotton for disposable cotton pads, sodium acetate is used to eliminate the buildup of static electricity.

Concrete longevity

Sodium acetate is used to mitigate water damage to concrete by acting as a concrete sealant, while also being environmentally benign and cheaper than the commonly used epoxy alternative for sealing concrete against water permeation.[9]

Food

Sodium acetate may be added to food as a seasoning, sometimes in the form of sodium diacetate, a one-to-one complex of sodium acetate and acetic acid,[10] given the E-number E262. It is often used to give potato chips a salt and vinegar flavor.

Buffer solution

A solution of sodium acetate (a basic salt of acetic acid) and acetic acid can act as a buffer to keep a relatively constant pH level. This is useful especially in biochemical applications where reactions are pH-dependent in a mildly acidic range (pH 4–6).

Heating pad

A hand warmer containing a supersaturated solution of sodium acetate which releases heat upon crystallization

Sodium acetate is also used in heating pads, hand warmers, and hot ice. Sodium acetate trihydrate crystals melt at 136.4 °F/58 °C[11] (to 137.12 °F/58.4 °C),[12] dissolving in their water of crystallization. When they are heated past the melting point and subsequently allowed to cool, the aqueous solution becomes supersaturated. This solution is capable of cooling to room temperature without forming crystals. By pressing on a metal disc within the heating pad, a nucleation center is formed, causing the solution to crystallize back into solid sodium acetate trihydrate. The bond-forming process of crystallization is exothermic.[13] The latent heat of fusion is about 264–289 kJ/kg.[11] Unlike some types of heat packs, such as those dependent upon irreversible chemical reactions, a sodium acetate heat pack can be easily reused by immersing the pack in boiling water for a few minutes, until the crystals are completely dissolved, and allowing the pack to slowly cool to room temperature.[14]

Preparation

A crystal of sodium acetate trihydrate (length 1.7 centimetres)

For laboratory use, sodium acetate is inexpensive and usually purchased instead of being synthesized. It is sometimes produced in a laboratory experiment by the reaction of acetic acid, commonly in the 5–8% solution known as vinegar, with sodium carbonate ("washing soda"), sodium bicarbonate ("baking soda"), or sodium hydroxide ("lye", or "caustic soda"). Any of these reactions produce sodium acetate and water. When a sodium and carbonate ion-containing compound is used as the reactant, the carbonate anion from sodium bicarbonate or carbonate, reacts with hydrogen from the carboxyl group (-COOH) in acetic acid, forming carbonic acid. Carbonic acid readily decomposes under normal conditions into gaseous carbon dioxide and water. This is the reaction taking place in the well-known "volcano" that occurs when the household products, baking soda and vinegar, are combined.

CH₃COOH + NaHCO₃ → CH₃COONa + H₂CO
₃

H₂CO
₃ → CO
₂ + H
₂O

Industrially, sodium acetate trihydrate is prepared by reacting acetic acid with sodium hydroxide using water as the solvent.

CH₃COOH + NaOH → CH₃COONa + H₂O

Reactions

Sodium acetate can be used to form an ester with an alkyl halide such as bromoethane:

CH₃COONa + BrCH₂CH₃ → CH₃COOCH₂CH₃ + NaBr

Sodium acetate undergoes decarboxylation to form methane (CH₄) under forcing conditions (pyrolysis in the presence of sodium hydroxide):

CH₃COONa + NaOH → CH₄ + Na₂CO₃

Calcium oxide is the typical catalyst used for this reaction. Caesium salts also catalyze this reaction.

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References

"Sodium Acetate". International Chemical Safety Cards. National Institute of Occupational Safety and Health. 2018-09-18.
"sodium acetate trihydrate". chemister.ru.
Seidell, Atherton; Linke, William F. (1952). Solubilities of Inorganic and Organic Compounds. Van Nostrand.
"sodium acetate". chemister.ru.
Sigma-Aldrich Co., Sodium acetate. Retrieved on 2014-06-07.
Acetic acid, sodium salt in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD), http://webbook.nist.gov (retrieved 2014-05-25)
Acetic acid, sodium salt, hydrate (1:1:3) in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD), http://webbook.nist.gov (retrieved 2014-05-25)
Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. ISBN 978-0-19-850346-0.
"Potato Chip Flavoring Boosts Longevity Of Concrete". Science Daily. 8 August 2007.
AG, Jungbunzlauer Suisse. "Sodium Diacetate – Jungbunzlauer". www.jungbunzlauer.com.
Ibrahim Dincer and Marc A. Rosen. Thermal Energy Storage: Systems and Applications, page 155
Courty JM, Kierlik E, Les chaufferettes chimiques, Pour la Science, décembre 2008, pp. 108–110
"Crystallization of Supersaturated Sodium Acetate". Journal of Chemical Education. 2015-07-19.
"How do sodium acetate heat pads work?". HowStuffWorks. April 2000. Retrieved 2007-09-03.

External links

Acetyl halides and salts of the acetate ion
AcOH																	He
LiOAc	Be(OAc)₂ BeAcOH											B(OAc)₃	AcOAc ROAc	NH₄OAc	AcOOH	FAc	Ne
NaOAc	Mg(OAc)₂											Al(OAc)₃ ALSOL Al(OAc)₂OH Al₂SO₄(OAc)₄	Si	P	S	ClAc	Ar
KOAc	Ca(OAc)₂	Sc(OAc)₃	Ti(OAc)₄	VO(OAc)₃	Cr(OAc)₂ Cr(OAc)₃	Mn(OAc)₂ Mn(OAc)₃	Fe(OAc)₂ Fe(OAc)₃	Co(OAc)₂, Co(OAc)₃	Ni(OAc)₂	Cu(OAc)₂	Zn(OAc)₂	Ga(OAc)₃	Ge	As(OAc)₃	Se	BrAc	Kr
RbOAc	Sr(OAc)₂	Y(OAc)₃	Zr(OAc)₄	Nb	Mo(OAc)₂	Tc	Ru(OAc)₂ Ru(OAc)₃ Ru(OAc)₄	Rh₂(OAc)₄	Pd(OAc)₂	AgOAc	Cd(OAc)₂	In	Sn(OAc)₂ Sn(OAc)₄	Sb(OAc)₃	Te	IAc	Xe
CsOAc	Ba(OAc)₂		Hf	Ta	W	Re	Os	Ir	Pt(OAc)₂	Au	Hg₂(OAc)₂, Hg(OAc)₂	TlOAc Tl(OAc)₃	Pb(OAc)₂ Pb(OAc)₄	Bi(OAc)₃	Po	At	Rn
Fr	Ra		Rf	Db	Sg	Bh	Hs	Mt	Ds	Rg	Cn	Nh	Fl	Mc	Lv	Ts	Og
		↓
		La(OAc)₃	Ce(OAc)_x	Pr	Nd	Pm	Sm(OAc)₃	Eu(OAc)₃	Gd(OAc)₃	Tb	Dy(OAc)₃	Ho(OAc)₃	Er	Tm	Yb(OAc)₃	Lu(OAc)₃
		Ac	Th	Pa	UO₂(OAc)₂	Np	Pu	Am	Cm	Bk	Cf	Es	Fm	Md	No	Lr

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[1] "Sodium Acetate". International Chemical Safety Cards. National Institute of Occupational Safety and Health. 2018-09-18.

[chemister2-2] "sodium acetate trihydrate". chemister.ru.

[sioc-3] Seidell, Atherton; Linke, William F. (1952). Solubilities of Inorganic and Organic Compounds. Van Nostrand.

[chemister-4] "sodium acetate". chemister.ru.

[sigma-5] Sigma-Aldrich Co., Sodium acetate. Retrieved on 2014-06-07.

[nist-6] Acetic acid, sodium salt in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD), http://webbook.nist.gov (retrieved 2014-05-25)

[nist2-7] Acetic acid, sodium salt, hydrate (1:1:3) in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD), http://webbook.nist.gov (retrieved 2014-05-25)

[8] Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. ISBN 978-0-19-850346-0.

[9] "Potato Chip Flavoring Boosts Longevity Of Concrete". Science Daily. 8 August 2007.

[10] AG, Jungbunzlauer Suisse. "Sodium Diacetate – Jungbunzlauer". www.jungbunzlauer.com.

[IDMA-11] Ibrahim Dincer and Marc A. Rosen. Thermal Energy Storage: Systems and Applications, page 155

[Température-12] Courty JM, Kierlik E, Les chaufferettes chimiques, Pour la Science, décembre 2008, pp. 108–110

[13] "Crystallization of Supersaturated Sodium Acetate". Journal of Chemical Education. 2015-07-19.

[14] "How do sodium acetate heat pads work?". HowStuffWorks. April 2000. Retrieved 2007-09-03.