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Octadecanoic Acid is one of several major long-chain fatty acids comprising oils and fats.
Octadecanoic Acid is presented in animal fats, oil and some kinds of vegetable oils as wellin the form of glycerides.
These oils, after hydrolysis, produce the Octadecanoic Acid.
CAS: 57-11-4
MF: C18H36O2
MW: 284.48
EINECS: 266-928-5
Synonyms
ACIDUM STEARICUM 50;CETYLACETIC ACID;FEMA 3035;CARBOXYLIC ACID C18;C18:0 FATTY ACID;hystrene5016;hystrene7018;hystrene80
Octadecanoic Acid is a molecule that is found in small quantities in animal and vegetable fats.
Octadecanoic Acid is used to create soaps, candles, and cosmetics.
Octadecanoic Acid can be synthesized from stearate by heating it with anhydrous sodium carbonate.
The reaction mechanism involves the formation of water vapor, which reacts with the sodium carbonate to produce sodium hydroxide, carbon dioxide, and hydrogen gas.
The hydrogen gas then combines with the stearic acid to form stearyl alcohol.
This process creates a particle that can be used as a catalyst for chemical reactions such as those found in bone cancer or fetal bovine growth.
Octadecanoic Acid binds calcium ions and has been shown to have potential use as a drug treatment for osteoporosis.
Octadecanoic Acid is a fatty acid widely existing in nature and has the general chemical properties of carboxylic acids.
Almost all kinds of fat and oil contain certain amount of stearic acid with the content in the animal fats being relative high.
For example, the content in the butter can reach up to 24% while the content in vegetable oil is relative low with the value in tea oil being 0.8% and the oil in palm being 6%.
However, the content in cocoa can reach as high as 34%.
There are two major approaches for industrial production of stearic acid, namely fractionation and compression method.
Add decomposition agent to the hydrogenated oil, and then hydrolyze to give the crude fatty acid, further go through washing with water, distillation, bleaching to obtain the finished products with glycerol as the byproduct.
Most domestic manufacturers use animal fat for production.
Some kinds of production technology will result in the incompletion of the distillation of fatty acid which produce stimulating odor at the time of the plastic processing and high temperatures.
Although these odor is of no toxic but they will have certain effect on the working conditions and the natural environment.
Most imported form of Octadecanoic Acid takes vegetable oil as the raw materials, the production processes are more advanced; the produced Octadecanoic Acid is of stable performance, good lubrication property and less odor in the application.
Octadecanoic Acid is mainly used for the production of stearates such as sodium stearate, magnesium stearate, calcium stearate, lead stearate, aluminum stearate, cadmium stearate, iron stearate, and potassium stearate.
The sodium or potassium salt of Octadecanoic Acid is the component of soap.
Although sodium stearate has a less decontamination ability than sodium palmitate, but its presence may increase the hardness of soap.
Take butter as raw material, go through sulfuric acid or pressurized method for decomposition.
The free fatty acids was first subject to water pressure method for removing the palmitic acid and oleic acid at 30~40 ℃, and then dissolved in ethanol, followed by addition of barium acetate or magnesium acetate which precipitates stearate.
Then further add dilute sulfuric acid to get the free stearate acid, filter and take it, and re-crystallize in ethanol to obtain the pure Hexanoic Acid.
Octadecanoic Acid is a long-chain saturated fatty acid.
Octadecanoic Acid is a major component of cocoa butter and has also been found in beef fat and vegetable oils.
Unlike many long-chain saturated fatty acids, dietary Octadecanoic Acid does not induce hypercholesterolemia or raise LDL-cholesterol.
Stearic acid (STAIR-ik or STEER-ik) is the saturated fatty acid with an 18 carbon chain and has the IUPAC name octadecanoic acid.
Octadecanoic Acid is a waxy solid, and its chemical formula is CH3(CH2)16CO2H.
Octadecanoic Acid's name comes from the Greek word στ?αρ "stéar", which means tallow.
The salts and esters of stearic acid are called stearates.
Octadecanoic Acid is one of the most common saturated fatty acids found in nature following palmitic acid.
A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids.
As well as in the diet, Octadecanoic Acid is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.
Octadecanoic Acid is a saturated fatty acid with an 18-carbon chain.
The IUPAC name is octadecanoic acid.
Octadecanoic Acid is a soft waxy solid with the formula CH3(CH2)16CO2H.
The triglyceride derived from three molecules of Octadecanoic Acid is called stearin.
Octadecanoic Acid is a prevalent fatty-acid in nature, found in many animal and vegetable fats, but is usually higher in animal fat than vegetable fat.
Octadecanoic Acid has a melting point of 69.4 °C (156.9 °F) °C and a pKa of 4.50.
Octadecanoic Acid's name comes from the Greek word στέαρ "stéar", which means tallow.
The salts and esters of stearic acid are called stearates.
As its ester, Octadecanoic Acid is one of the most common saturated fatty acids found in nature and in the food supply, following palmitic acid.
Dietary sources of stearic acid include meat, poultry, fish, eggs, dairy products, and foods prepared with fats; beef tallow, lard, butterfat, cocoa butter, and shea butter are rich fat sources of stearic acid.
Octadecanoic Acid Chemical Properties
Melting point: 67-72 °C (lit.)
Boiling point: 361 °C (lit.)
Density: 0.845 g/cm3
Bulk density: 400-500kg/m3
Vapor pressure: 1 mm Hg ( 173.7 °C)
Refractive index: 1.4299
FEMA: 3035 | STEARIC ACID
Fp: >230 °F
Storage temp.: Store below +30°C.
Solubility: Practically insoluble in water, soluble in ethanol (96 per cent) and in light petroleum (bp: 50-70 °C).
Form: powder
pka: pKa 5.75±0.00(H2O t = 35) (Uncertain)
Specific Gravity: 0.84 (80℃)
Color: White
Odor: odorless mild fatty
Odor Type: odorless
Biological source: palm oil
Water Solubility: 0.1-1 g/100 mL at 23 ºC
Merck: 14,8804
JECFA Number: 116
BRN: 608585
Exposure limits: ACGIH: TWA 10 mg/m3; TWA 3 mg/m3
Dielectric constant: 2.3（22℃）
InChIKey: QIQXTHQIDYTFRH-UHFFFAOYSA-N
LogP: 8.22
CAS DataBase Reference: 57-11-4(CAS DataBase Reference)
NIST Chemistry Reference: Octadecanoic Acid (57-11-4)
EPA Substance Registry System: Octadecanoic Acid (57-11-4)
Pure product appears as white shiny soft small pieces.
Octadecanoic Acid is slightly soluble in water, soluble in alcohol, acetone, easily soluble in benzene, chloroform, ether, carbon tetrachloride, carbon disulfide, amyl acetate and toluene.
Octadecanoic Acid has a characteristic odor and taste resembling tallow.
Octadecanoic Acid is a mixture of solid organic acids obtained from fats consisting chiefly of stearic acid (C18H36O2) and palmitic acid (C16H32O2).
Octadecanoic Acid is a hard, white or faintly yellow-colored, somewhat glossy, crystalline solid or a white or yellowish white powder.
Octadecanoic Acid has a slight odor (with an odor threshold of 20 ppm) and taste suggesting tallow.
Octadecanoic Acid, CH3(CH2)16COOH, is a white or colorless, waxlike solid with a melting point of 70°C (158 OF), and a boiling point of 232°C (450 OF) at 2 kPa.
Octadecanoic Acid is soluble in alcohol, ether, and chloroform,and is insolublein water.
Octadecanoic Acid, nature's most common fatty acid, is derived from natural animal and vegetable fats.
Also known as n-octadecanoic acid, Octadecanoic Acid is used in the preparation of metallic stearates, as a lubricant, and in pharmaceuticals, cosmetics, candles, and food packaging.
Uses
Octadecanoic Acid is widely used in cosmetics, plastics plasticizers, mold release agents, stabilizers, surfactants, rubber vulcanization accelerator, waterproof agent, polishing agent, metal soap, metal mineral flotation agents, softeners and pharmaceuticals as well as other organic chemicals.
Octadecanoic Acid can also be used as the solvents of oil-soluble paint, crayons lubrication agent, stencil lighting agent and the emulsifier of stearic acid glyceride.
Octadecanoic Acid can also be widely used in the manufacturing of PVC pipe, sheet material, profiles and film and is the PVC heat stabilizers with good lubricity and excellent stability against light and heat.
In the application of polyvinyl chloride pipe, Octadecanoic Acid helps prevent the "coke" during the processing and is effective heat stabilizer during PVC film processing while also preventing the discoloration of the finished film discoloration caused by exposure.
Octadecanoic Acid has become the additive for lubrication, plasticization and stabilization of the filled masterbatch.
Octadecanoic Acid can effectively improve the coating activating effect of inorganic powder and increase the flow rate of materials.
When there is demand for a large flow rate of the melt for material with inorganic powder accounting for the most part, an appropriate increase in the content of Octadecanoic Acid can significantly increase the melt flow rate of material.
However, the amount of Octadecanoic Acid used in filled masterbatch also have threshold with its amount being controlled in about 1% of the total mass.
If the added amount is over-excessive, Octadecanoic Acid will not only cause the decrease of the quality and the performance of plastic products but also generate sticky substance in the die lip location of the manufacturing equipment of the plastic products, affecting the production efficiency and product quality.
The mono-or multi-alcohol ester of Octadecanoic Acid can be used as cosmetics, nonionic surfactants and plasticizers.
Octadecanoic Acid's alkali metal salt can be dissolved in water and is a major component of soap.
Other kinds of salts can be used as waterproofing agents, lubricants, bactericides, coating additives and PVC stabilizers.
Octadecanoic Acid can be used as natural rubber, synthetic rubber (except butyl rubber) and latex curing active agent.
Octadecanoic Acid can also be used as raw material of plastic plasticizer and stabilizer.
Medicine: Octadecanoic Acid can be used for the preparation of ointments, suppositories, etc., as well as being used in the manufacture of cosmetics, candles, waterproof agent and polishing agent.
Octadecanoic Acid can be used as a lubricant, defoamers and food additives in the food industry as well as the raw materials of glycerol stearate, stearic acid sorbitol anhydride esters and sucrose esters.
Octadecanoic Acid can also be used as standard reference product for gas analysis as well as the preparation of soap, cosmetics, pharmaceuticals and other organic chemicals.
Octadecanoic Acid is a fatty acid that is a mixture of solid organic acids obtained principally from stearic acid and palmitic acid.
Octadecanoic Acid is practi- cally insoluble in water.
Octadecanoic Acid functions as a lubricant, binder, and defoamer.
Octadecanoic Acid is used as a softener in chewing gum base.
Pharmaceutic aid (emulsion adjunct); pharmaceutic aid (tablet and/or capsule lubricant).
Octadecanoic Acid is an emulsifier and thickening agent found in many vegetable fats.
Octadecanoic Acid is the main ingredient used in making bar soaps and lubricants.
Octadecanoic Acid occurs naturally in butter acids, tallow, cascarilla bark, and in other animal fats and oils.
Octadecanoic Acid may cause allergic reactions in people with sensitive skin and is considered somewhat comedogenic.
Generally applications of Octadecanoic 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.
Octadecanoic Acid undergoes the typical reactions of saturated carboxylic acids, notably reduction to stearyl alcohol, and esterification with a range of alcohols.
Soaps , cosmetics , detergents
Octadecanoic 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 Octadecanoic Acid, but indirectly by saponification of triglycerides consisting of stearic acid esters.
Esters of Octadecanoic 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 Octadecanoic 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 to soften PVC.
Octadecanoic 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.
Niche uses
Being inexpensively available and chemically benign, Octadecanoic Acid finds many niche applications.
When making plaster castings from a plaster piece mold or waste mold and when making the mold from a shellacked clay original.
In this use, powdered Octadecanoic 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.
When reacted with zinc it forms zinc stearate which is used a lubricant for playing cards (fanning powder) to ensure a smooth motion when fanning.
In compressed confections, Octadecanoic Acid is used as a lubricant to keep the tablet from sticking to the die.
Fatty acids are classic components of candle - making.
Octadecanoic Acid is used along with simple sugar or corn syrup as a hardener in candies.
Octadecanoic Acid is used to produce dietary supplements.
In fire works, Octadecanoic 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.
Octadecanoic Acid is a common lubricant during injection molding and pressing of ceramic powders.
Octadecanoic Acid is also used as a mold release for foam latex that is baked in stone molds.
Food
Of the saturated fatty acids consumed in the United States, Octadecanoic Acid consumption is second (26% of total saturated fatty acid intake) to palmitic acid (56% of total saturated fatty acid intake).
Octadecanoic Acid is more abundant in animal fat (up to 33% in beef liver: 739 ) than in vegetable fat (typically less than 5%).
The important exceptions are the foods cocoa butter (34%) and shea butter, where the Octadecanoic Acid content (as a triglyceride) is 28–45%.
Examples of the use of Octadecanoic Acid in food manufacturing include baked goods, frozen dairy products, gelatins, puddings, hard candy, and nonalcoholic beverages.
Octadecanoic Acid (E number E570) is found in some foods.
Soaps and cosmetics
Octadecanoic Acid is mainly used in the production of detergents, soaps, and cosmetics such as shampoos and shaving cream products.
Stearate soap, such as sodium stearate, could be made from Octadecanoic Acid but instead are usually produced by saponification of stearic acid-containing triglycerides.
Esters of Octadecanoic Acid with ethylene glycol (glycol stearate and glycol distearate) are used to produce a pearly effect in shampoos, soaps, and other cosmetic products.
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 stabilizers for PVC. Octadecanoic 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, Octadecanoic Acid 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 Octadecanoic 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.
Octadecanoic Acid can be converted to zinc stearate, which is used as a lubricant for playing cards (fanning powder) to ensure a smooth motion when fanning.
Octadecanoic Acid is a common lubricant during injection molding and pressing of ceramic powders.
Pharmaceutical Applications
Octadecanoic Acid is widely used in oral and topical pharmaceutical formulations.
Octadecanoic Acid is mainly used in oral formulations as a tablet and capsule lubricant, although it may also be used as a binder or in combination with shellac as a tablet coating.
Octadecanoic Acid has also been suggested that stearic acid may be used in enteric tablet coatings and as a sustained-release drug carrier.
In topical formulations, Octadecanoic Acid is used as an emulsifying and solubilizing agent.
When partially neutralized with alkalis or triethanolamine, Octadecanoic Acid is used in the preparation of creams.
The partially neutralized Octadecanoic Acid forms a creamy base when mixed with 5–15 times its own weight of aqueous liquid, the appearance and plasticity of the cream being determined by the proportion of alkali used.
Octadecanoic Acid is used as the hardening agent in glycerin suppositories.
Octadecanoic Acid is also widely used in cosmetics and food products.
Production method
There are two major approaches for industrial production of Octadecanoic Acid, namely fractionation and compression method.
Add decomposition agent to the hydrogenated oil, and then hydrolyze to give the crude fatty acid, further go through washing with water, distillation, bleaching to obtain the finished products with glycerol as the byproduct.
Compression method takes animal oil as raw material.
Have animal oil subject to hydrolysis in the catalysis of zinc oxide at pressure of 1.17~1.47 MPa, further go through pickling, washing, distillation, cooling, freezing, press for removal of oleic acid to get the finished products.
Heat the cotton seed oil, rice bran oil, or soybean oil in the presence of a hydrolyzing agent under normal pressure to boiling with hydrolysis of 1.5 h and harden to saturated fatty acid.
Oleic acid hydrogenation;
Use the C10~C20 and C18~C20 fraction of the synthetic fatty acid as raw materials, go through melting, pickling (with 1% sulfuric acid) mold, pressing, melting, pickling, dehydrating and crystallization to obtain Octadecanoic Acid.
Octadecanoic Acid can be obtained through the low-temperature segment separation of the mixed fatty acid.
Octadecanoic Acid can also be made through the hydrogenation of oleic acid.
Production Methods
Octadecanoic Acid is manufactured by hydrolysis of fat by continuous exposure to a countercurrent stream of high-temperature water and fat in a high-pressure chamber.
The resultant mixture is purified by vacuum steam distillation and the distillates are then separated using selective solvents.
Octadecanoic Acid may also be manufactured by the hydrogenation of cottonseed and other vegetable oils; by the hydrogenation and subsequent saponification of olein followed by recrystallization from alcohol; and from edible fats and oils by boiling with sodium hydroxide, separating any glycerin, and decomposing the resulting soap with sulfuric or hydrochloric acid.
The Octadecanoic Acid is then subsequently separated from any oleic acid by cold expression.
Octadecanoic Acid is derived from edible fat sources unless it is intended for external use, in which case nonedible fat sources may be used.
The USP32–NF27 states that Octadecanoic Acid labeled solely for external use is exempt from the requirement that it be prepared from edible sources.
Octadecanoic Acid may contain a suitable antioxidant such as 0.005% w/w butylated hydroxytoluene.
Production Methods
Octadecanoic Acid occurs in many animal and vegetable fats and oils, but it is more abundant in animal fat (up to 30 %) than vegetable fat (typically < 5 % ).
The important exceptions are cocoa butter and shea butter where the Octadecanoic Acid content (as a triglyceride) is 28 – 45 %.
Octadecanoic Acid is prepared by treating these fats and oils with water at a high pressure and temperature (above 200 °C), leading to the hydrolysis of triglycerides.
The resulting mixture is then distilled.
Commercial Octadecanoic Acid is often a mixture of stearic and palmitic acids, although purified stearic acid is available.
In terms of its biosynthesis, Octadecanoic Acid is produced from carbohydrates via the fatty acid synthesis machinery via acetyl-CoA.
