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 the fatty 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.

The 12-hydroxystearic acid is prepared by the hydrogenation of castor oil. [3] After primary reaction of the saturation of most of the double bonds, dehydration and reduction of the hydroxyl group leads to the stearic acid. Hydrogenated castor oil results in a mixture of 12-hydroxystearic acid and stearic acid.

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

Soap is a salt of a fatty acid used in a variety of cleansing and lubricating products. In a domestic setting, 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, and precursors to catalysts.

<span class="mw-page-title-main">Castor oil</span> Vegetable oil obtained by pressing the seeds of the Castor plant

Castor oil is a vegetable oil pressed from castor beans. 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% 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">Tallow</span> Rendered form of beef or mutton fat

Tallow is a rendered form of beef or mutton fat, primarily made up of triglycerides.

<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 that involves the conversion of fat, oil, or lipid, into soap and alcohol by the action of aqueous alkali. Soaps are salts of fatty acids, which in turn are carboxylic acids with long carbon chains. A typical soap is sodium oleate.

<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 ( STEER-ik, 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. The triglyceride derived from three molecules of stearic acid is called stearin.

In chemistry, a saturated compound is a chemical compound that resists the addition reactions, such as hydrogenation, oxidative addition, and binding of a Lewis base. The term is used in many contexts and for many classes of chemical compounds. Overall, saturated compounds are less reactive than unsaturated compounds. Saturation is derived from the Latin word saturare, meaning 'to fill'.

In organic chemistry a halohydrin is a functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms, which otherwise bear only hydrogen or hydrocarbyl groups. The term only applies to saturated motifs, as such compounds like 2-chlorophenol would not normally be considered halohydrins. Megatons of some chlorohydrins, e.g. propylene chlorohydrin, are produced annually as precursors to polymers.

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 in 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">Extreme pressure additive</span>

Extreme pressure additives, or EP additives, are additives for lubricants with a role to decrease wear of the parts of the gears exposed to very high pressures. They are also added to cutting fluids for machining of metals.

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.

<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, bad smells, and clutter on surfaces. Purposes of cleaning agents include health, beauty, removing offensive odor, 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.

An oil drying agent, also known as siccative, is a coordination compound that accelerates (catalyzes) the hardening of drying oils, often as they are used in oil-based paints. This so-called "drying" occurs through free-radical chemical crosslinking of the oils. The catalysts promote this free-radical autoxidation of the oils with air.

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. It is produced by the reaction of cadmium chloride with sodium stearate or heating stearic acid and cadmium oxide or hydroxide. 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.

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.