Stearic acid

Stearic acid (/ˈstɪərɪk/ STEER-ik, /stiˈærɪk/ stee-ARR-ik) is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid.[11] The triglyceride derived from three molecules of stearic acid is called stearin.

Stearic acid[1]
Names
Preferred IUPAC name
Octadecanoic acid
Other names
Stearic acid
C18:0 (Lipid numbers)
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.285
EC Number
  • 200-313-4
IUPHAR/BPS
KEGG
RTECS number
  • WI2800000
UNII
CompTox Dashboard (EPA)
SMILES
  • CCCCCCCCCCCCCCCCCC(=O)O
Properties
C18H36O2
Molar mass 284.484 g·mol−1
Appearance White solid
Odor Pungent, oily
Density 0.9408 g/cm3 (20 °C)[2]
0.847 g/cm3 (70 °C)
Melting point 69.3 °C (156.7 °F; 342.4 K)[2]
Boiling point 361 °C (682 °F; 634 K)
decomposes
232 °C (450 °F; 505 K)
at 15 mmHg[2]
Solubility in water
 0.00018 g/100 g (0 °C)
0.00029 g/100 g (20 °C)
0.00034 g/100 g (30 °C)
0.00042 g/100 g (45 °C)
0.00050 g/100 g (60 °C)[3]
Solubility Soluble in alkyl acetates, alcohols, HCOOCH3, phenyls, CS2, CCl4[4]
Solubility in dichloromethane 3.58 g/100 g (25 °C)
8.85 g/100 g (30 °C)
18.3 g/100 g (35 °C)[4]
Solubility in hexane 0.5 g/100 g (20 °C)
4.3 g/100 g (30 °C)
19 g/100 g (40 °C)
79.2 g/100 g (50 °C)
303 g/100 g (60 °C)[4]
Solubility in ethanol 1.09 g/100 mL (10 °C)
2.25 g/100 g (20 °C)
5.42 g/100 g (30 °C)
22.7 g/100 g (40 °C)
105 g/100 g (50 °C)
400 g/100 g (60 °C)[3]
Solubility in acetone 4.73 g/100 g[5]
Solubility in chloroform 15.54 g/100 g[5]
Solubility in toluene 13.61 g/100 g[5]
Vapor pressure 0.01 kPa (158 °C)[2]
0.46 kPa (200 °C)
16.9 kPa (300 °C)[6]
−220.8·10−6 cm3/mol
Thermal conductivity 0.173 W/m·K (70 °C)
0.166 W/m·K (100 °C)[7]
1.4299 (80 °C)[2]
Structure
B-form = Monoclinic[8]
Space group
 B-form = P21/a[8]
Point group
 B-form = Cs
2h[8]
Lattice constant
a = 5.591 Å, b = 7.404 Å, c = 49.38 Å (B-form)[8]
α = 90°, β = 117.37°, γ = 90°
Thermochemistry
501.5 J/mol·K[2][6]
Std molar
entropy (S⦵298)
 435.6 J/mol·K[2]
Std enthalpy of
formation (ΔfH⦵298)
 −947.7 kJ/mol[2]
Std enthalpy of
combustion (ΔcH⦵298)
 −11342.4 kJ/mol[9]
Hazards
NFPA 704 (fire diamond)
1
1
0
Flash point 113 °C (235 °F; 386 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 4640 mg/kg (rats, oral)[10]
21.5 mg/kg (rats, intravenous)[4]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Occurrence and production

Stearic acid is more abundant in animal fat (up to 30%) than in vegetable fat (typically <5%). The important exceptions are the foods cocoa butter (34%)[12] and shea butter, where the stearic acid content (as a triglyceride) is 28–45%.[13]

In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks.[14]

Stearic acid is obtained from fats and oils by the saponification of the triglycerides using hot water (about 100 °C). The resulting mixture is then distilled.[15] Commercial stearic acid is often a mixture of stearic and palmitic acids, although purified stearic acid is available. Commercially, fats high in oleic acid such as palm and soy may be hydrogenated to convert oleic into stearic acid.

Uses

In general, the applications of stearic acid exploit its bifunctional character, with a polar head group that can be attached to metal cations and a nonpolar chain that confers solubility in organic solvents. The combination leads to uses as a surfactant and softening agent. Stearic acid undergoes the typical reactions of saturated carboxylic acids, a notable one being reduction to stearyl alcohol, and esterification with a range of alcohols. This is used in a large range of manufactures, from simple to complex electronic devices.

As food additive

Stearic acid (E number E570) is found in some foods.[16]

Soaps, cosmetics, detergents

Stearic acid is mainly used in the production of detergents, soaps, and cosmetics such as shampoos and shaving cream products. Soaps are not made directly from stearic acid, but indirectly by saponification of triglycerides consisting of stearic acid esters. Esters of stearic acid with ethylene glycol (glycol stearate and glycol distearate) are used to produce a pearly effect in shampoos, soaps, and other cosmetic products. They are added to the product in molten form and allowed to crystallize under controlled conditions. Detergents are obtained from amides and quaternary alkylammonium derivatives of stearic acid.

Lubricants, softening and release agents

In view of the soft texture of the sodium salt, which is the main component of soap, other salts are also useful for their lubricating properties. Lithium stearate is an important component of grease. The stearate salts of zinc, calcium, cadmium, and lead are used as heat stabilisers PVC. Stearic acid is used along with castor oil for preparing softeners in textile sizing. They are heated and mixed with caustic potash or caustic soda. Related salts are also commonly used as release agents, e.g. in the production of automobile tires. As an example, it can be used to make castings from a plaster piece mold or waste mold, and to make a mold from a shellacked clay original. In this use, powdered stearic acid is mixed in water and the suspension is brushed onto the surface to be parted after casting. This reacts with the calcium in the plaster to form a thin layer of calcium stearate, which functions as a release agent.[17]

When reacted with zinc it forms zinc stearate, which is used as a lubricant for playing cards (fanning powder) to ensure a smooth motion when fanning. Stearic acid is a common lubricant during injection molding and pressing of ceramic powders.[18] It is also used as a mold release for foam latex that is baked in stone molds.

Niche uses

Being inexpensive, nontoxic, and fairly inert, stearic acid finds many niche applications.[15] Stearic acid is used as a negative plate additive in the manufacture of lead-acid batteries. It is added at the rate of 0.6 g per kg of the oxide while preparing the paste. It is believed to enhance the hydrophobicity of the negative plate, particularly during dry-charging process. It also reduces the extension of oxidation of the freshly formed lead (negative active material) when the plates are kept for drying in the open atmosphere after the process of tank formation. As a consequence, the charging time of a dry uncharged battery during initial filling and charging (IFC) is comparatively lower, as compared to a battery assembled with plates which do not contain stearic acid additive. Fatty acids are classic components of candle-making. Stearic acid is used along with simple sugar or corn syrup as a hardener in candies. In fireworks, stearic acid is often used to coat metal powders such as aluminium and iron. This prevents oxidation, allowing compositions to be stored for a longer period of time.

Metabolism

An isotope labeling study in humans[19] concluded that the fraction of dietary stearic acid that oxidatively desaturates to oleic acid is 2.4 times higher than the fraction of palmitic acid analogously converted to palmitoleic acid. Also, stearic acid is less likely to be incorporated into cholesterol esters. In epidemiologic and clinical studies, stearic acid was found to be associated with lowered LDL cholesterol in comparison with other saturated fatty acids.[20]

Salts and esters

Stearates are the salts or esters of stearic acid. The conjugate base of stearic acid, C17H35COO−, is also known as the stearate anion.

Examples
Salts
  • Calcium stearate
  • Lithium stearate
  • Magnesium stearate
  • Sodium stearate
  • Zinc stearate
Esters
  • Estradiol stearate
  • Glycol stearate
  • Stearin
  • Testosterone stearate

References
  1. Susan Budavari, ed. (1989). Merck Index (11th ed.). Rahway, New Jersey: Merck & Co., Inc. p. 8761. ISBN 978-0-911910-28-5.
  2. Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
  3. Ralston, A.W.; Hoerr, C.W. (1942). "The Solubilities of the Normal Saturated Fatty Acids". The Journal of Organic Chemistry. 7 (6): 546–555. doi:10.1021/jo01200a013. PMID 20280727.
  4. "stearic acid". Chemister.ru. 2007-03-19. Retrieved 2017-06-30.
  5. Seidell, Atherton; Linke, William F. (1919). Solubilities of Inorganic and Organic Compounds (2nd ed.). D. Van Nostrand Company. p. 677.
  6. Octadecanoic acid 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) (retrieved 2014-06-15)
  7. Vargaftik, Natan B.; et al. (1993). Handbook of Thermal Conductivity of Liquids and Gases (illustrated ed.). CRC Press. p. 318. ISBN 978-0-8493-9345-7.
  8. von Sydow, E. (1955). "On the structure of the crystal form B of stearic acid". Acta Crystallographica. 8 (9): 557–560. doi:10.1107/S0365110X55001746.
  9. National Center for Biotechnology Information (2021). PubChem Compound Summary for CID 5281, Stearic acid. Retrieved January 7, 2021 from https://pubchem.ncbi.nlm.nih.gov/compound/Stearic-acid.
  10. Science Lab.com. "Stearic acid MSDS" (PDF). Retrieved 2020-09-30.
  11. Gunstone, F. D., John L. Harwood, and Albert J. Dijkstra "The Lipid Handbook with Cd-Rom. 3rd ed. Boca Raton: CRC Press, 2007. ISBN 0849396883 | ISBN 978-0849396885
  12. "硬脂酸;十八烷酸;十八酸;十八碳烷酸;Stearic acid;Octadecanoic acid;物理性质,化学性质,英文名,分子量,结构式,分子式,CAS号,制备方法,用途,溶点,沸点,毒性,MSDS,供应商,公司". www.chemyq.com. Retrieved 2020-06-17.
  13. Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi:10.1351/pac200173040685. S2CID 84492006.
  14. "Fatty Acids: Straight-chain Saturated, Structure, Occurrence and Biosynthesis". lipidlibrary.aocs.org. Lipid Library, The American Oil Chemists' Society. 30 April 2011. Archived from the original on 21 July 2011.
  15. Anneken, David J.; Both, Sabine; Christoph, Ralf; Fieg, Georg; Steinberner, Udo; Westfechtel, Alfred (2006). "Fatty Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_245.pub2.
  16. Fernando Aguilar, Riccardo Crebelli, Alessandro Di Domenico, Birgit Dusemund, Maria Jose Frutos, Pierre Galtier, David Gott, Ursula Gundert-Remy, Claude Lambré, Jean-Charles Leblanc, Oliver Lindtner, Peter Moldeus, Alicja Mortensen, Pasquale Mosesso, Dominique Parent-Massin, Agneta Oskarsson, Ivan Stankovic, Ine Waalkens-Berendsen, Rudolf Antonius Woutersen, Matthew Wright and Maged Younes. (2017). "Re-evaluation of fatty acids (E 570) as a food additive". EFSA Journal. 15 (5): 4785. doi:10.2903/j.efsa.2017.4785. PMC 7009963. PMID 32625490.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  17. Angelo Nora, Alfred Szczepanek, Gunther Koenen (2005). "Metallic Soaps". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_361.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
  18. Tsenga, Wenjea J.; Mo Liua, Dean; Hsub, Chung-King (1999). "Influence of stearic acid on suspension structure and green microstructure of injection-molded zirconia ceramics". Ceramics International. 25 (2): 191–195. doi:10.1016/S0272-8842(98)00024-8.
  19. Emken, Edward A. (1994). "Metabolism of dietary stearic acid relative to other fatty acids in human subjects". American Journal of Clinical Nutrition. 60 (6): 1023S–1028S. doi:10.1093/ajcn/60.6.1023S. PMID 7977144.
  20. Hunter, J. E.; Zhang, J.; Kris-Etherton, P. M. (2009). "Cardiovascular disease risk of dietary stearic acid compared with trans, other saturated, and unsaturated fatty acids: A systematic review". American Journal of Clinical Nutrition. 91 (1): 46–63. doi:10.3945/ajcn.2009.27661. PMID 19939984.
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