Lithium 12-hydroxystearate

Lithium 12-hydroxystearate
Names

IUPAC name Lithium 12-hydroxyoctadecanoate
Identifiers
CAS Number	7620-77-1^Y
3D model (JSmol)	Interactive image
ChemSpider	99662
ECHA InfoCard	100.028.669
PubChem CID	111018
UNII	AO71K6FGH8^Y
CompTox Dashboard (EPA)	DTXSID9027655
InChI 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
SMILES [Li+].[O-]C(=O)CCCCCCCCCCC(O)CCCCCC
Properties
Chemical formula	C₁₈H₃₅LiO₃
Molar mass	306.42 g·mol⁻¹
Appearance	White 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). Infobox references

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.

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.

References

^ Wietelmann, U.; Bauer, R.J. (2000). "Lithium and Lithium Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH.
^ 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
^ 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.

External links

Hughs, R (2011). "Understanding the Basics of Grease". ReliabilityWeb. Archived from the original on 2011-01-07.

v t e Lithium compounds (list)
Inorganic (list)	Li₂ LiAlCl₄ Li_1+xAl_xGe_2−x(PO₄)₃ LiAlH₄ LiAlO₂ LiAl_1+xTi_2−x(PO₄)₃ LiAs LiAsF₆ Li₃AsO₄ LiAt Li[AuCl₄] LiB(C₂O₄)₂ LiB(C₆F₅)₄ LiWF₆ LiBF₄ LiBH₄ LiBO₂ LiB₃O₅ Li₂B₄O₇ LiAsF₆ Li₂SnF₆ Li₂TiF₆ Li₂ZrF₆ Li₂B₄O₇·5H₂O LiBSi₂ LiBr LiBr·2H₂O LiBrO LiBrO₂ LiBrO₃ LiBrO₄ Li₂C₂ LiCF₃SO₃ CH₃CH(OH)COOLi LiC₂H₂ClO₂ LiC₂H₃IO₂ Li(CH₃)₂N LiCHO₂ LiCH₃O LiC₂H₅O LiCN Li₂CN₂ LiCNO Li₂CO₃ Li₂C₂O₄ LiCl LiCl·H₂O LiClO LiFO LiClO₂ LiClO₃ LiClO₄ LiCoO₂ Li₂CrO₄ Li₂CrO₄·2H₂O Li₂Cr₂O₇ CsLiB₆O₁₀ LiD LiF Li₂F LiF₄Al Li₃F₆Al FLiBe LiFePO₄ FLiNaK LiGaH₄ Li₂GeF₆ Li₂GeO₃ LiGe₂(PO₄)₃ LiH LiH₂AsO₄ Li₂HAsO₄ LiHCO₃ Li₃H(CO₃)₂ LiH₂PO₃ LiH₂PO₄ LiHSO₃ LiHSO₄ LiHe LiI LiIO LiIO₂ LiIO₃ LiIO₄ Li₂IrO₃ Li₇La₃Zr₂O₁₂ LiMn₂O₄ Li₂MoO₄ Li_0.9Mo₆O₁₇ LiN₃ Li₃N LiNH₂ Li₂NH LiNO₂ LiNO₃ LiNO₃·H₂O Li₂N₂O₂ LiNa Li₂NaPO₃ LiNaNO₂ LiNbO₃ Li₂NbO₃ LiO⁻ LiO₂ LiO₃ Li₂O Li₂O₂ LiOH Li₃P LiPF₆ Li₃PO₄ Li₂HPO₃ Li₂HPO₄ Li₃PO₃ Li₃PO₄ Li₂Po Li₂PtO₃ Li₂RuO₃ Li₂S LiSCN LiSH LiSO₃F Li₂SO₃ Li₂SO₄ Li[SbF₆] Li₂Se Li₂SeO₃ Li₂SeO₄ LiSi Li₂SiF₆ Li₄SiO₄ Li₂SiO₃ Li₂Si₂O₅ LiTaO₃ Li₂Te LiTe₃ Li₂TeO₃ Li₂TeO₄ Li₂TiO₃ Li₄Ti₅O₁₂ LiTi₂(PO₄)₃ LiVO₃·2H₂O Li₃V₂(PO₄)₃ Li₂WO₄ LiYF₄ Neodymium-doped LiZr₂(PO₄)₃ Li₂ZrO₃
Organic (soaps)	Hemolithin (extraterrestrial protein) Organolithium reagents Gilman reagent CH₃COOLi C₄H₆LiNO₄ LiC₂F₆NO₄S₂ LiN(SiMe₃)₂ Li₃C₆H₅O₇ C₅H₅Li LiN(C₃H₇)₂ (C₆H₅)₂PLi C₁₈H₃₅LiO₃ C₆H₁₃Li C₄H₉Li CH₃CHLiCH₂CH₃ (CH₃)₃CLi C₁₂H₂₈BLi CH₃Li Li⁺C₁₀H−8 C₅H₁₁Li C₅H₃LiN₂O₄ C₆H₅Li LiC₂CH₃ LiO₂C(CH₂)₁₆CH₃ C₄H₅LiO₄ LiEt₃BH LiOC(CH₃)₃ C₉H₁₈LiN LiC₂H₃ Vinyllithium LiC ₁₁H ₂₃COO
Minerals	Amblygonite Berezanskite Brannockite Cryolithionite Darapiosite Darrellhenryite Elbaite Fluorine Elbaite Fluor-liddicoatite Emeleusite Eucryptite LiAlSiO₄ Faizievite Hectorite Hsianghualite Jadarite LiNaSiB₃O₇OH Keatite Li(AlSi₂O₆) Kunzite Lavinskyite Lepidolite Lithiophilite LiMnPO₄ Lithiophosphate Li₃PO₄ Manandonite Manganoneptunite Nambulite Neptunite Olympite Petalite LiAlSi₄O₁₀ Pezzottaite Cs(Be₂Li)Al₂Si₆O₁₈ Rossmanite Saliotite Sogdianite Spodumene LiAl(SiO₃)₂ Sugilite Tiptopite Tourmaline Triphylite LiFePO₄ Zabuyelite Li₂CO₃ Zektzerite Zinnwaldite
Hypothetical	Li_xBe_y HLiHe⁺ LiFHeO LiHe₂ (HeO)(LiF)₂ La_2⁄3–xLi_3xTiO₃He
Other Li-related	Aluminium–lithium alloys Heteroatom-promoted lateral lithiation LB buffer Lithium atom Lithium medication LiNi_xCo_yAl_zO₂ LiNi_xMn_yCo_zO₂ Lithium soap Lithium Triangle Lucifer yellow Magnesium–lithium alloys NASICON Environmentally friendly red light flare

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