Lithium 12-hydroxystearate (C₁₈H₃₅LiO₃) is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

classified as a

lithium soap 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 (white ...

. In chemistry, "soap" refers to salts of

fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, fr ...

s. Lithium 12-hydroxystearate is a white solid. Lithium soaps are key component of many lubricating greases.

Use

Lithium 12-hydroxystearate exhibits high

oxidation Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...

stability and a

dropping point The dropping point of a lubricating grease is an indication of the heat resistance of the grease and is the temperature at which it passes from a semi-solid to a liquid state under specific test conditions. It is dependent on the type of thickener ...

up to around 200 °C. Most greases used today in motor vehicles, aircraft, and heavy machinery contain

lithium stearate 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. Lithiu ...

s, mainly lithium 12-hydroxystearate. Greases can be made with the addition of several different metallic soaps. Some greases are prepared from

sodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable iso ...

barium Barium is a chemical element with the symbol Ba and atomic number 56. It is the fifth element in group 2 and is a soft, silvery alkaline earth metal. Because of its high chemical reactivity, barium is never found in nature as a free element. Th ...

lithium Lithium (from el, λίθος, lithos, lit=stone) is a chemical element with the symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard conditions, it is the least dense metal and the least dense solid el ...

, and

calcium Calcium is a chemical element with the symbol Ca and atomic number 20. As an alkaline earth metal, calcium is a reactive metal that forms a dark oxide-nitride layer when exposed to air. Its physical and chemical properties are most similar to ...

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 Lithium hydroxide is an inorganic compound with the formula LiOH. It can exist as anhydrous or hydrated, and both forms are white hygroscopic solids. They are soluble in water and slightly soluble in ethanol. Both are available commercially. While ...

and the

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.Angelo Nora, Alfred Szczepanek, Gunther Koenen, "Metallic Soaps" in Ullmann’s Encyclopedia of Industrial Chemistry 2005 Wiley-VCH, Weinheim. Since these lithium soaps are difficult to filter, they are collected by

spray drying Spray drying is a method of changing a dry powder from a liquid or slurry by rapidly drying with a hot gas. This is the preferred method of drying of many thermally-sensitive materials such as foods and pharmaceuticals, or materials which may requ ...

. For applications, lithium 12-hydroxystearate is usually dispersed in synthetic oils such as

silicone oil A silicone oil is any liquid polymerized siloxane with organic side chains. The most important member is polydimethylsiloxane. These polymers are of commercial interest because of their relatively high thermal stability, lubricating, and Liquid di ...

and

ester oil In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fa ...

. 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 Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a Catalysis, catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or S ...

castor oil 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 and its density is 0.961 g/cm3. It includes a mixture of triglycerides in which about ...

. After primary reaction of the

saturation Saturation, saturated, unsaturation or unsaturated may refer to: Chemistry * Saturation, a property of organic compounds referring to carbon-carbon bonds **Saturated and unsaturated compounds ** Degree of unsaturation **Saturated fat or fatty aci ...

of most of the

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

dehydration In physiology, dehydration is a lack of total body water, with an accompanying disruption of metabolic processes. It occurs when free water loss exceeds free water intake, usually due to exercise, disease, or high environmental temperature. Mil ...

and reduction of the

hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy g ...

leads to the

stearic acid Stearic acid ( , ) 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. ...

. Hydrogenated castor oil results in a mixture of 12-hydroxystearic acid and stearic acid.

References

External links

* {{Lithium compounds Greases Lithium salts Organolithium compounds Stearates