Lithium 12-hydroxystearate

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Lithium 12-hydroxystearate
Lithium 12-hydroxystearate.svg
Names
IUPAC name
Lithium 12-hydroxyoctadecanoate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.028.669 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C18H36O3.Li/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21;/h17,19H,2-16H2,1H3,(H,20,21);/q;+1/p-1
  • [Li+].[O-]C(=O)CCCCCCCCCCC(O)CCCCCC
Properties
C18H35LiO3
Molar mass 306.42 g·mol−1
AppearanceWhite powder
Melting point >200 °C (392 °F; 473 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lithium 12-hydroxystearate (C18H35LiO3) is a chemical compound classified as a lithium soap. In chemistry, "soap" refers to salts of fatty acids. Lithium 12-hydroxystearate is a white solid. Lithium soaps are key component of many lubricating greases.

Contents

Use

Lithium 12-hydroxystearate exhibits high oxidation stability and a dropping point up to around 200 °C. Most greases used today in motor vehicles, aircraft, and heavy machinery contain lithium stearates, mainly lithium 12-hydroxystearate. [1] Greases can be made with the addition of several different metallic soaps. Some greases are prepared from sodium, barium, lithium, and calcium soaps. Lithium soap greases are preferred for their water resistance, and their oxidative and mechanical stability. Depending on the grease, they also have good performance at high or low temperatures, but not both.

Production

To produce lithium 12-hydroxystearate, lithium hydroxide and 12-hydroxystearic acid are combined in an aqueous medium. With vigorous stirring, dilute monohydrate lithium hydroxide is gradually added to a dispersion of the fatty acid in water heated to slightly below boiling. [2] Since these lithium soaps are difficult to filter, they are collected by spray drying. For applications, lithium 12-hydroxystearate is usually dispersed in synthetic oils such as silicone oil and ester oil. The synthetic oils are preferred for their greater stability and ability to perform at extreme temperatures.

12-hydroxystearic acid is prepared by the hydrogenation of castor oil, followed by saponification with sodium hydroxide and acidification with hydrochloric acid. [3] This process converts ricinoleate moieties in castor oil triglycerides to 12-hydroxystearate, with stearate as a byproduct from dehydration of the hydroxy acid followed by hydrogenation. Lithium soaps manufactured from hydrogenated castor oil typically contain a mixture of lithium 12-hydroxystearate and lithium stearate.

Related Research Articles

<span class="mw-page-title-main">Soap</span> Substance used for cleaning

Soap is a salt of a fatty acid used for cleaning and lubricating products as well as other applications. In a domestic setting, soaps, specifically "toilet soaps", are surfactants usually used for washing, bathing, and other types of housekeeping. In industrial settings, soaps are used as thickeners, components of some lubricants, emulsifiers, and catalysts.

<span class="mw-page-title-main">Castor oil</span> Vegetable oil pressed from castor beans

Castor oil is a vegetable oil pressed from castor beans, the seeds of the plant Ricinus communis. The seeds are 40 to 60 percent oil. It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is 313 °C (595 °F) and its density is 0.961 g/cm3. It includes a mixture of triglycerides in which about 90 percent of fatty acids are ricinoleates. Oleic acid and linoleic acid are the other significant components.

Rancidification is the process of complete or incomplete autoxidation or hydrolysis of fats and oils when exposed to air, light, moisture, or bacterial action, producing short-chain aldehydes, ketones and free fatty acids.

<span class="mw-page-title-main">Potassium hydroxide</span> Inorganic compound (KOH)

Potassium hydroxide is an inorganic compound with the formula KOH, and is commonly called caustic potash.

Saponification is a process of cleaving esters into carboxylate salts and alcohols by the action of aqueous alkali. Typically aqueous sodium hydroxide solutions are used. It is an important type of alkaline hydrolysis. When the carboxylate is long chain, its salt is called a soap. The saponification of ethyl acetate gives sodium acetate and ethanol:

<span class="mw-page-title-main">Stearin</span> Chemical compound

Stearin, or tristearin, or glyceryl tristearate is an odourless, white powder. It is a triglyceride derived from three units of stearic acid. Most triglycerides are derived from at least two and more commonly three different fatty acids. Like other triglycerides, stearin can crystallise in three polymorphs. For stearin, these melt at 54 (α-form), 65, and 72.5 °C (β-form).

<span class="mw-page-title-main">Stearic acid</span> Eighteen-carbon straight-chain fatty acid

Stearic acid is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a soft waxy solid with the formula CH3(CH2)16CO2H. The triglyceride derived from three molecules of stearic acid is called stearin. Stearic 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. It has a melting point of 69.4 °C (156.9 °F) °C and a pKa of 4.50.

<span class="mw-page-title-main">Raney nickel</span> Chemical compound

Raney nickel, also known as the primary catalyst for the Cormas-Grisius Electrophilic Benzene Addition, is a fine-grained solid composed mostly of nickel derived from a nickel–aluminium alloy. Several grades are known, of which most are gray solids. Some are pyrophoric, but most are used as air-stable slurries. Raney nickel is used as a reagent and as a catalyst in organic chemistry. It was developed in 1926 by American engineer Murray Raney for the hydrogenation of vegetable oils. Raney Nickel is a registered trademark of W. R. Grace and Company. Other major producers are Evonik and Johnson Matthey.

The smoke point, also referred to as the burning point, is the temperature at which an oil or fat begins to produce a continuous bluish smoke that becomes clearly visible, dependent upon specific and defined conditions. Smoke point values can vary greatly, depending on factors such as the volume of oil utilized, the size of the container, the presence of air currents, the type and source of light as well as the quality of the oil and its acidity content, otherwise known as free fatty acid (FFA) content. The more FFA an oil contains, the quicker it will break down and start smoking. The lower the value of FFA, the higher the smoke point. However, the FFA content typically represents less than 1% of the total oil and consequently renders smoke point a poor indicator of the capacity of a fat or oil to withstand heat.

Grease is a solid or semisolid lubricant formed as a dispersion of thickening agents in a liquid lubricant. Grease generally consists of a soap emulsified with mineral or vegetable oil.

<span class="mw-page-title-main">Hydroperoxide</span> Class of chemical compounds

Hydroperoxides or peroxols are compounds of the form ROOH, where R stands for any group, typically organic, which contain the hydroperoxy functional group. Hydroperoxide also refers to the hydroperoxide anion and its salts, and the neutral hydroperoxyl radical (•OOH) consist of an unbond hydroperoxy group. When R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds.

<span class="mw-page-title-main">Sodium stearate</span> Chemical compound

Sodium stearate is the sodium salt of stearic acid. This white solid is the most common soap. It is found in many types of solid deodorants, rubbers, latex paints, and inks. It is also a component of some food additives and food flavorings.

<span class="mw-page-title-main">Lithium soap</span>

Lithium soap is a soap consisting of a lithium salt of a fatty acid. Sodium-based and potassium-based soaps are used as cleaning agents in domestic and industrial applications, whereas lithium soaps are used as components of lithium grease.

Sodium atoms have 11 electrons, one more than the stable configuration of the noble gas neon. As a result, sodium usually forms ionic compounds involving the Na+ cation. Sodium is a reactive alkali metal and is much more stable in ionic compounds. It can also form intermetallic compounds and organosodium compounds. Sodium compounds are often soluble in water.

<span class="mw-page-title-main">Cleaning agent</span> Substance used to remove dirt or other contaminants

Cleaning agents or hard-surface cleaners are substances used to remove dirt, including dust, stains, foul odors, and clutter on surfaces. Purposes of cleaning agents include health, beauty, removing offensive odors, and avoiding the spread of dirt and contaminants to oneself and others. Some cleaning agents can kill bacteria and clean at the same time. Others, called degreasers, contain organic solvents to help dissolve oils and fats.

Soap scum or lime soap is the white solid composed of calcium stearate, magnesium stearate, and similar alkaline earth metal derivatives of fatty acids. These materials result from the addition of soap and other anionic surfactants to hard water. Hard water contains calcium and magnesium ions, which react with the surfactant anion to give these metallic or lime soaps.

Lithium stearate is a chemical compound with the formula LiO2C(CH2)16CH3. It is formally classified as a soap (a salt of a fatty acid). Lithium stearate is a white soft solid, prepared by the reaction of lithium hydroxide and stearic acid.

Cadmium stearate is a salt with the formula Cd(O2CC17H35)2. Classified as a metallic soap, this a white solid is used as a lubricant and as a heat- and light-stabilizer in polyvinyl chloride. The use of cadmium stearate is being phased out because of its toxicity.

A metallic soap is a metallic salt of a fatty acid. Theoretically, soaps can be made of any metal, although not all enjoy practical uses. Varying the metal can strongly affect the properties of the compound, particularly its solubility.

Strontium stearate is a metal-organic compound, a salt of strontium and stearic acid with the chemical formula C
36
H
70
SrO
4
. The compound is classified as a metallic soap, i.e. a metal derivative of a fatty acid.

References

  1. Wietelmann, U.; Bauer, R.J. (2000). "Lithium and Lithium Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH.
  2. Angelo Nora, Alfred Szczepanek, Gunther Koenen, "Metallic Soaps" in Ullmann’s Encyclopedia of Industrial Chemistry 2005 Wiley-VCH, Weinheim. doi : 10.1002/14356007.a16_361
  3. Maskaev, A.; Mankovskaya, N.; Lendel, I.; Fedorovskii, T.; Simurova, E.; Terenteva, V (1971). "Preparation of 12-hydroxystearic acid, the raw material for plastic greases". Chemistry and Technology of Fuels and Oils. New York: Springer.