Octadecanoic acid

• CAS: 57-11-4
• Catalog Number: ACM57114
• Category: Material of Cosmetics; Fatty Acids and Ester Homologs
• Molecular Weight: 284.48
• Molecular Formula: C18H36O2
• Description: Stearic acid is a white solid with a mild odor. Floats on water. (USCG, 1999);DryPowder; DryPowder, OtherSolid, Liquid; Liquid; OtherSolid; OtherSolid, Liquid; PelletsLargeCrystals; PelletsLargeCrystals, Liquid; PelletsLargeCrystals, WetSolid, OtherSolid; WetSolid, Liquid;Solid;Solid;WHITE CRYSTALS OR POWDER WITH CHARACTERISTIC ODOUR.;hard, white or faintly yellowish crystalline solid/tallow odour;White solid with a mild odor.
• Synonyms: Stearic acid
• IUPAC Name: octadecanoic acid
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)O
• InChI: InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)
• InChI Key: QIQXTHQIDYTFRH-UHFFFAOYSA-N
• Boiling Point: 361 °C (lit.)
• Melting Point: 67-72 °C (lit.)
• Flash Point: 385 °F (NTP, 1992);113 °C (235 °F) - closed cup;385 °F (196 dec C) (closed cup);196 °C;385°F
• Density: 0.86 at 68 °F (USCG, 1999);0.9408 g/cu cm at 20 °C;Relative density (water = 1): 0.94-0.83;0.86
• Solubility: 1 to 10 mg/mL at 73° F (NTP, 1992);2.10e-06 M;0.000597 mg/mL at 25 °C;In water, 0.568 mg/L at 25 °C;In water, 0.597 mg/L at 25 °C;Insoluble in water;Slightly soluble in ethanol, benzene; soluble in acetone, chloroform, carbon disulfide;1 gram dissolves in 21 mL alcohol, 5 mL benzene, 2 mL chloroform, 26 mL acetone, 6 mL carbon tetrachloride, 3.4 mL carbon disulfide; also soluble in amyl acetate, toluene;Soluble in alcohol, ether, chloroform, carbon disulfide, carbon tetrachloride;0.000597 mg/mL;Solubility in water: none;practically insoluble in water; soluble in alcohol, ether, chloroform;1 g in 20 ml alcohol (in ethanol)
• Appearance: Solid
• Application: Octadecanoic acid, also known as stearic acid, is a versatile fatty acid with an 18-carbon chain, commonly found in both animal and vegetable fats. It appears as a white, wax-like solid with a melting point of 70°C. This compound serves multiple purposes due to its ability to connect with other substances, acting as an emulsifier and thickening agent in various formulations. In the pharmaceutical industry, octadecanoic acid is primarily used as a lubricant in tablet and capsule production, contributing to their stability and release properties. It also enhances the consistency and texture of creams when partially neutralized with alkalis. In cosmetics, it functions as a stabilizing agent, while its use extends to the production of metallic stearates, soaps, lubricants, and additives in the manufacturing of PVC products. Through fractionation and other industrial processes, octadecanoic acid is refined for different applications, embodying nature's abundant and functional resource.
• Storage: Room temperature
• Autoignition Temperature: 743 °F (USCG, 1999);743 °F;395 °C
• CNo Chain: C18:0
• Color/Form: Monoclinic leaflets from alcohol;White or slightly yellow crystal masses, or white to slightly yellow powder;Colorless, wax-like solid;White amorphous solid or leaflets
• Complexity: 202
• Compound Derivative: Acid
• Covalently-Bonded Unit Count: 1
• Decomposition: Decomposes at boiling point of 360 °C at 1 mm Hg.;When heated to decomposition it emits acrid smoke and irritating fumes.;376 °C
• EC Number: 200-313-4;273-087-8
• Exact Mass: 284.27153g/mol
• Fatty Acid: Octadecanoic; (Stearic)
• Formal Charge: 0
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Heavy Atom Count: 20
• ICSC Number: 0568
• LogP: 8.23 (LogP);8.23;log Kow = 8.23;8.23
• Monoisotopic Mass: 284.27153g/mol
• NSC Number: 25956
• Odor: Slight odor suggesting tallow
• Other Experimental: Does not congeal below 54 °C. Slowly volatilizes at 90 to 100 °C;Index of refraction: 1.4299 at 80 °C;Vapor pressure = 1 mm Hg at 173.1 °C;White, crystalline solid; odorless or practically so; MP 33-35 °C; BP 224 °C. Ethyl stearate of commerce solidifies at 20-24 °C; BP 180 deg at 4 mm Hg. Insoluble in water; soluble in alcohol or ether /Stearic acid ethyl ester/;White crystals. MP 38-389 °C; BP 215 °C at 15 mm Hg. Insoluble in water, soluble in alcohol, ether /Stearic acid , methyl ester/;Hydroxyl radical reaction rate constant = 2.25X10-11 cu cm/molec-sec at 25 °C (est)
• Physical State: Solid
• Refractive Index: Index of refraction: 1.6130 at 20 °C
• Rotatable Bond Count: 16
• RTECS Number: WI2800000
• Stability: Stable under recommended storage conditions.
• UNII: 4ELV7Z65AP
• Vapor Density: 9.8 (NTP, 1992) (Relative to Air);9.80 (Air = 1);9.8
• Vapor Pressure: 1 mm Hg at 344.7 °F ; 5 mm Hg at 408.2° F (NTP, 1992);7.22e-07 mmHg;7.22X10-7 mm Hg at 25 °C (ext);Vapor pressure, Pa at 174 °C: 133;1 mmHg at 344.7°F; 5 mmHg at 408.2°F
• Viscosity: 9.87 mPa.sec (cP) at 70 °C
• XLogP3: 7.4

Synthetic Use

Upstream Synthesis Route 1

• 111-61-5

• 57-11-4

Reference: [1]Journal of the Society of Chemical Industry,1927,vol. 46,p. 471 T
Chemisches Zentralblatt,1928,vol. 99,p. 674
[2]Journal of the American Oil Chemists' Society,1956,vol. 33,p. 317
[3]Journal of the American Oil Chemists' Society,2002,vol. 79,p. 23 - 27

Upstream Synthesis Route 2

• 111-61-5

• 74-85-1
• 57-11-4

Reference: [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1908,vol. 147,p. 1056

Upstream Synthesis Route 3

• 72849-35-5

• 57-11-4

Reference: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1956,vol. 76,p. 960
Chem.Abstr.,1957,p. 891

Downstream Synthesis Route 1

• 107-15-3
• 57-11-4

• 110-30-5

Reference: [1] Patent: CN105777568, 2016, A, . Location in patent: Paragraph 0024; 0025

Downstream Synthesis Route 2

• 6780-13-8
• 57-11-4

• 871-79-4
• 110-30-5

Reference: [1] Nippon Kagaku Zasshi, 1948, vol. 69, p. 154,156[2] Chem.Abstr., 1952, p. 3951

Downstream Synthesis Route 3

• 57-11-4

• 110-30-5

Reference: [1] Langmuir, 2010, vol. 26, # 23, p. 17890 - 17895

* For details of the synthesis route, please refer to the original source to ensure accuracy.