Stearyl alcohol[1]
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Names
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Preferred IUPAC name
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Other names
1-octadecanol
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Identifiers
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CAS Number
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ChEBI
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ChEMBL
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ChemSpider
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ECHA InfoCard
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100.003.652
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UNII
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InChI=1S/C18H38O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h19H,2-18H2,1H3 Y Key: GLDOVTGHNKAZLK-UHFFFAOYSA-N Y InChI=1/C18H38O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h19H,2-18H2,1H3 Key: GLDOVTGHNKAZLK-UHFFFAOYAZ
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Properties
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Chemical formula
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C18H38O
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Molar mass
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270.49 g/mol
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Appearance
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White solid
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Density
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0.812 g/cm3
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Melting point
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59.4 to 59.8 °C (138.9 to 139.6 °F; 332.5 to 332.9 K)
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Boiling point
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210 °C (410 °F; 483 K) at 15 mmHg (2.0 kPa)
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1.1×10−3 mg/L
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Hazards
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Flash point
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185 °C (365 °F; 458 K)
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Stearyl alcohol, or 1-octadecanol, is an organic compound classified as a saturated fatty alcohol with the formula CH3(CH2)16CH2OH. It takes the form of white granules or flakes, which are insoluble in water. It has a wide range of uses as an ingredient in lubricants, resins, perfumes, and cosmetics. It is used as an emollient, emulsifier, and thickener in ointments, and is widely used as a hair coating in shampoos and hair conditioners. Stearyl heptanoate, the ester of stearyl alcohol and heptanoic acid (enanthic acid), is found in most cosmetic eyeliners. Stearyl alcohol has also found application as an evaporation suppressing monolayer when applied to the surface of water.[2]
Stearyl alcohol is prepared from stearic acid or certain fats by the process of catalytic hydrogenation. It has low toxicity.[3]
References
- ^ Merck Index, 11th Edition, 8762.
- ^ Prime, E. L., Tran, D. N., Plazzer, M., Sunartio, D., Leung, A. H., Yiapanis, G., ... & Solomon, D. H. (2012). Rational design of monolayers for improved water evaporation mitigation. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 415, 47-58.
- ^ Noweck, Klaus; Grafahrend, Wolfgang (2006). "Fatty Alcohols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_277.pub2. ISBN 978-3-527-30673-2.
External links
Alcohols |
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By consumption | Alcohols found in alcoholic drinks | |
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Medical alcohol |
- Ethchlorvynol
- Methylpentynol
- Methanol poisoning
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Toxic alcohols | |
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Primary alcohols (1°) | Methanol |
- 4-Methylcyclohexanemethanol
- Aminomethanol
- Cyclohexylmethanol
- Methoxymethanol
- Methylazoxymethanol
- Trifluoromethanol
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Ethanol |
- 1-Aminoethanol
- 2,2,2-Trichloroethanol
- 2,2,2-Trifluoroethanol
- 2-(2-Ethoxyethoxy)ethanol
- 2-(2-Methoxyethoxy)ethanol
- 2-(2-Methoxyethoxy)ethanol
- 2-Butoxyethanol
- 2-Chloroethanol
- 2-Ethoxyethanol
- 2-Fluoroethanol
- 2-Mercaptoethanol
- 2-Methoxyethanol
- Aminoethylethanolamine
- Diethylethanolamine
- Dimethylethanolamine
- Ethanol
- Ethanolamine
- N,N-Diisopropylaminoethanol
- N-Methylethanolamine
- Phenoxyethanol
- Tribromoethanol
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Butanol | |
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Straight-chain saturated C1 — C9 | |
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Straight-chain saturated C10 — C19 | |
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Straight-chain saturated C20 — C29 |
- 1-Icosanol (arachidyl)
- 1-Heneicosanol
- 1-Docosanol (behenyl)
- 1-Tricosanol
- 1-Tetracosanol (lignoceryl)
- 1-Pentacosanol
- 1-Hexacosanol (ceryl)
- 1-Heptacosanol
- 1-Octacosanol (cluytyl / montanyl)
- 1-Nonacosanol
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Straight-chain saturated C30 — C39 |
- 1-Triacontanol (melissyl / myricyl)
- 1-Hentriacontanol
- 1-Dotriacontanol (lacceryl)
- 1-Tritriacontanol
- 1-Tetratriacontanol (geddyl)
- 1-Pentatriacontanol
- 1-Hexatriacontanol
- 1-Heptatriacontanol
- 1-Octatriacontanol
- 1-Nonatriacontanol
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Straight-chain saturated C40 — C49 |
- 1-Tetracontanol
- 1-Hentetracontanol
- 1-Dotetracontanol
- 1-Tritetracontanol
- 1-Tetratetracontanol
- 1-Pentatetracontanol
- 1-Hexatetracontanol
- 1-Heptatetracontanol
- 1-Octatetracontanol
- 1-Nonatetracontanol
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- 2-Ethylhexanol
- Allyl alcohol
- Anisyl alcohol
- Benzyl alcohol
- Cinnamyl alcohol
- Crotyl alcohol
- Furfuryl alcohol
- Isoamyl alcohol
- Neopentyl alcohol
- Nicotinyl alcohol
- Perillyl alcohol
- Phenethyl alcohol
- Prenol
- Propargyl alcohol
- Salicyl alcohol
- Tryptophol
- Vanillyl alcohol
- Veratrole alcohol
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Secondary alcohols (2°) | |
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Tertiary alcohols (3°) | |
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Hydric alcohols | Monohydric alcohols | |
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Dihydric alcohols |
- Ethylene glycol
- Propylene glycol
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Trihydric alcohols | |
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Polyhydric alcohols (sugar alcohols) |
- Pentaerythritol
- Ethylene glycol (C2)
- Glycerol, Propylene glycol (C3)
- Erythritol, Threitol (C4)
- Xylitol (C5)
- Mannitol, Sorbitol (C6)
- Volemitol (C7)
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Amyl alcohols | |
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Aromatic alcohols |
- Benzyl alcohol
- 2,4-Dichlorobenzyl alcohol
- 3-Nitrobenzyl alcohol
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Saturated fatty alcohols | |
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Branched and unsaturated fatty alcohols | |
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Sugar alcohols | C1 — C7 |
- Methylene glycol (C1)
- Ethylene glycol (C2)
- Glycerol (C3)
- Erythritol (C4)
- Threitol (C4)
- Arabitol (C5)
- Ribitol (C5)
- Xylitol (C5)
- Mannitol (C6)
- Sorbitol (C6)
- Galactitol (C6)
- Iditol (C6)
- Volemitol (C7)
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Deoxy sugar alcohols | |
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Cyclic sugar alcohols | |
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Glycylglycitols |
- Maltitol
- Lactitol
- Isomalt
- Maltotriitol
- Maltotetraitol
- Polyglycitol
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Terpene alcohols | Monoterpene alcohols |
- Borneol
- Citronellol
- Geraniol
- Linalool
- Menthol
- Nerol
- Rhodinol
- Terpineol
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Sesquiterpene alcohols | |
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Diterpene alcohols | |
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Dialcohols |
- 1,4-Butanediol
- 1,5-Pentanediol
- 2-Methyl-2-propyl-1,3-propanediol
- Diethylpropanediol
- Ethylene glycol
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Trialcohols | |
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Sterols | |
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Fluoroalcohols |
- 1,3-Difluoro-2-propanol
- 2,2,2-Trifluoroethanol
- 2-Fluoroethanol
- Nonafluoro-tert-butyl alcohol
- Trifluoromethanol
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Preparations |
- Substitution of haloalkane
- Carbonyl reduction
- Ether cleavage
- Hydrolysis of epoxide
- Hydration of alkene
- Ziegler process
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Reactions |
- Deprotonation
- Protonation
- Alcohol oxidation
- Nucleophilic substitution
- Fischer–Speier esterification
- Williamson ether synthesis
- Elimination reaction
- Nucleophilic substitution of carbonyl group
- Friedel-Crafts alkylation
- Nucleophilic conjugate addition
- Transesterification
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