{{chembox | verifiedrevid = 443708329 | Reference = <ref>''Merck Index'', 12th Edition, '''3464'''.</ref> | ImageFile = Dodecan-1-ol.svg | ImageClass = skin-invert | ImageSize = 250px | ImageName = Skeletal formula | ImageFile1 = Lauryl-alcohol-3D-vdW.png | ImageClass1 = bg-transparent | ImageSize1 = 210px | ImageName1 = Space-filling model | PIN = Dodecan-1-ol | OtherNames = Dodecanol<br>1-Dodecanol<br>Dodecyl alcohol<br>Lauryl alcohol | Section1 = {{Chembox Identifiers | Abbreviations = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 7901 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 178A96NLP2 | InChIKey = LQZZUXJYWNFBMV-UHFFFAOYAU | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 24722 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C12H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = LQZZUXJYWNFBMV-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 112-53-8 | EINECS = | PubChem = 8193 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB06894 | SMILES = OCCCCCCCCCCCC | InChI = 1/C12H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3 | RTECS = | MeSHName = | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 28878 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C02277 }} | Section2 = {{Chembox Properties | C=12 | H=26 | O=1 | Appearance = Colorless solid | Density = 0.8309 g/cm<sup>3</sup> | MeltingPtC = 24 | MeltingPt_notes = | BoilingPtC = 259 | BoilingPt_notes = | Solubility = 0.004 g/L<ref>{{GESTIS|ZVG=35500}}</ref> | SolubleOther = Soluble | Solvent = ethanol and diethyl ether | pKa = | pKb = | MagSus = {{val|-147.70e−6|u=cm<sup>3</sup>/mol}} }} | Section7 = {{Chembox Hazards | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | GHSPictograms = {{GHS07}}{{GHS09}} | GHSSignalWord = warning | HPhrases = {{HPhrases|319|410|411}} | PPhrases = {{PPhrases|264+265|273|280|305+351+338|337+317|391|501}} | GHS_ref = <ref>GHS: [https://gestis.dguv.de/data?name=035500 GESTIS 035500]</ref> | FlashPtC = 127 | AutoignitionPtC = | ExploLimits = | PEL = }} | Section9 = {{Chembox Related | OtherFunction = {{Unbulleted list|Dodecanal|Dodecanoic acid|1-Bromododecane}} }} }}

'''Dodecanol''' {{IPAc-en|ˈ|d|oʊ|ˈ|d|ɛ|k|ɑː|n|ɒ|l}}, or '''lauryl alcohol''', is an organic compound produced industrially from palm kernel oil or coconut oil. It is a fatty alcohol. Sulfate esters of lauryl alcohol, especially sodium lauryl sulfate, are very widely used as surfactants. Sodium lauryl sulfate and the related dodecanol derivatives ammonium lauryl sulfate and sodium laureth sulfate are all used in shampoos. Dodecanol is tasteless, colorless, and has a floral odor.<ref name=Marvel/>

==Production and use== In 1993, the European demand of dodecanol was around 60,000 tonnes per year. It can be obtained from palm kernel oil or coconut oil fatty acids and methyl esters by hydrogenation.<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a10_277.pub2|title=Fatty Alcohols|year=2006|last1=Noweck|first1=Klaus|last2=Grafahrend|first2=Wolfgang|isbn=3527306730}}</ref> It may also be produced synthetically via the Ziegler process. A classic laboratory method involves Bouveault-Blanc reduction of ethyl laurate.<ref name=Marvel>{{cite journal|doi=10.15227/orgsyn.010.0062|journal=Organic Syntheses|volume=10|pages=62|year=1930|title=Lauryl Alcohol|first1=S. G. |last1=Ford|first2=C. S. |last2=Marvel}}</ref>

Dodecanol is used to make surfactants, which are used in lubricating oils, and pharmaceuticals. Millions of tons of sodium dodecylsulfate (SDS) are produced annually by sulfation of dodecyl alcohol:<ref name=UllmannSurf>{{cite book|doi=10.1002/14356007.a25_747.pub2 |chapter=Surfactants |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2019 |last1=Holmberg |first1=Krister |pages=1–56 |isbn=978-3-527-30673-2 }}</ref> :{{chem2|SO3 + CH3(CH2)10CH2OH → CH3(CH2)10CH2OSO3H}} :{{chem2|CH3(CH2)10CH2OSO3H + NaOH→CH3(CH2)10CH2OSO3Na + H2O}}

Dodecanol is used as an emollient. It is also the precursor to dodecanal, an important fragrance, and 1-bromododecane, an alkylating agent for improving the lipophilicity of organic molecules.

== Toxicity ==

Dodecanol can irritate the skin. It has about half the toxicity of ethanol, but it is very harmful to marine organisms.<ref>{{Cite web |url=http://msds.chem.ox.ac.uk/DO/1-dodecanol.html |title=MSDS Safety Sheet |access-date=2009-06-14 |archive-date=2011-07-16 |archive-url=https://web.archive.org/web/20110716143955/http://msds.chem.ox.ac.uk/DO/1-dodecanol.html |url-status=dead }}</ref>

== Mutual solubility with water==

The mutual solubility of 1-dodecanol and water has been quantified as follows.<ref>Richard Stephenson and James Stuart, "Mutual Binary Solubilities: Water-Alcohols and Water-Esters", J. Chem. Eng. Data, 1986, 31, 56-70.</ref>

:{| class="wikitable sortable" |+'''Mutual solubility of water and 1-dodecanol (98%, melting point 24&nbsp;°C), Weight %''' |- !Temperature (°C) !! Solubility of dodecanol in water !! Solubility of water in dodecanol |- | 29.5 || 0.04 || 2.87 |- | 40.0 || 0.05 || 2.85 |- | 50.2 || 0.09 || 2.69 |- | 60.5 || 0.15 || 2.96 |- | 70.5 || 0.09 || 2.70 |- | 80.3 || 0.14 || 2.89 |- | 90.8 || 0.18 || 2.96 |- | standard deviation || 0.02 || 0.01 |- |}

== References == {{Reflist}}

== External links == * [https://web.archive.org/web/20060516001103/http://physchem.ox.ac.uk/MSDS/DO/1-dodecanol.html MSDS at Oxford] * [http://hazard.com/msds/mf/baker/baker/files/d8784.htm MSDS at J.T. Baker]

{{Alcohols}}

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Category:Fatty alcohols Category:Primary alcohols Category:Alkanols Category:Dodecyl compounds