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Revision as of 17:02, 8 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEBI').← Previous edit		Latest revision as of 19:33, 5 May 2024 edit undoSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,983 editsm →Production and use: CH3(CH2)10CH2
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	{{chembox		{{chembox
	| verifiedrevid = 414434433		| verifiedrevid = 443708329
	| Reference = <ref>'']'', 12th Edition, '''3464'''.</ref>		| Reference = <ref>'']'', 12th Edition, '''3464'''.</ref>
	| ImageFile = Dodecanol.svg		| ImageFile = Dodecanol.svg
	| ImageSize = 250px		| ImageSize = 250px
	| ImageName = Skeletal formula		| ImageName = Skeletal formula
	| ImageFile1 = Lauryl-alcohol-3D-vdW.png		| ImageFile1 = Lauryl-alcohol-3D-vdW.png
	| ImageSize1 = 210px		| ImageSize1 = 210px
	| ImageName1 = Space-filling model		| ImageName1 = Space-filling model
	| IUPACName = Dodecan-1-ol		| PIN = Dodecan-1-ol
	| OtherNames = Dodecanol<br>1-Dodecanol<br>Dodecyl alcohol<br>Lauryl alcohol		| OtherNames = Dodecanol<br>1-Dodecanol<br>Dodecyl alcohol<br>Lauryl alcohol
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
	| Abbreviations =		| Abbreviations =
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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	| EINECS =		| EINECS =
	| PubChem = 8193		| PubChem = 8193
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB06894		| DrugBank = DB06894
	| SMILES = OCCCCCCCCCCCC		| SMILES = OCCCCCCCCCCCC
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	| RTECS =		| RTECS =
	| MeSHName =		| MeSHName =
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 28878		| ChEBI = 28878
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C02277		| KEGG = C02277
			}}
	| ATCCode_prefix =
		⚫	| Section2 = {{Chembox Properties
	| ATCCode_suffix =
			| C=12 | H=26 | O=1
	| ATC_Supplemental =}}
⚫	| Section2 = {{Chembox Properties
	| Formula = C<sub>12</sub>H<sub>26</sub>O
	| MolarMass = 186.34
	| Appearance = Colorless solid		| Appearance = Colorless solid
	| Density = 0.8309		| Density = 0.8309
	| MeltingPtC = 24		| MeltingPtC = 24
	| Melting_notes =		| MeltingPt_notes =
	| BoilingPtC = 259		| BoilingPtC = 259
	| Boiling_notes =		| BoilingPt_notes =
	| Solubility = Insol		| Solubility = 0.004 g/L<ref>{{GESTIS|ZVG=35500}}</ref>
	| SolubleOther = Soluble		| SolubleOther = Soluble
	| Solvent = ] and ]		| Solvent = ] and ]
	| pKa =		| pKa =
	| pKb = }}		| pKb =
			| MagSus = {{val|-147.70e−6|u=cm<sup>3</sup>/mol}} }}
⚫	| Section7 = {{Chembox Hazards
			| Section5 = {{Chembox Related
	| EUClass =
			| OtherFunction = {{Unbulleted list|]|]|]}}
	| EUIndex =
			}}
		⚫	| Section7 = {{Chembox Hazards
	| MainHazards =		| MainHazards =
	| NFPA-H =		| NFPA-H =
	| NFPA-F =		| NFPA-F =
	| NFPA-R =		| NFPA-R =
	| NFPA-O =		| NFPA-S =
			| GHSPictograms = {{GHS07}}{{GHS09}}
	| RPhrases =
			| GHSSignalWord = warning
	| SPhrases =
	| RSPhrases = {{R36}}		| HPhrases = {{HPhrases|H319|H410}}
			| PPhrases = {{PPhrases|P273|P305+P351+P338}}
	| FlashPt = 127 °C
			| GHS_ref = <ref>GHS: </ref>
	| Autoignition =
			| FlashPtC = 127
			| AutoignitionPtC =
	| ExploLimits =		| ExploLimits =
	| PEL = }}		| PEL = }}
	}}		}}
			'''Dodecanol''' {{IPAc-en|ˈ|d|oʊ|ˈ|d|ɛ|k|ɑː|n|ɒ|l}}, or '''lauryl alcohol''', is an ] produced industrially from ] or ]. It is a ]. ] of lauryl alcohol, especially ], are very widely used as ]. Sodium lauryl sulfate and the related dodecanol derivatives ] and ] are all used in ]s. Dodecanol is tasteless, colorless, and has a floral odor.<ref name=Marvel/>
	'''Dodecanol''', also known by its ] name '''1-dodecanol''' or '''dodecan-1-ol''', and by its trivial name '''dodecyl alcohol''' and '''lauryl alcohol''', is a ]. Dodecanol is a colourless, water insoluble solid of melting point 24&nbsp;°C and boiling point 259&nbsp;°C. It has a floral odor. It can be obtained from ] or ] ]s and methyl esters by ].
			==Production and use==
	Dodecanol is used to make ]s, ] ]s, and ]s.
			In 1993, the European demand of dodecanol was around 60,000 ]s per year. It can be obtained from ] or ] ]s and methyl esters by ].<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 ]. A classic laboratory method involves ] 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 ]s, which are used in ] ]s, and ]s. Millions of tons of ] (SDS) are produced annually by ] 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>
	In cosmetics, dodecanol is used as an ].
			:{{chem2|SO3 + CH3(CH2)10CH2OH → CH3(CH2)10CH2OSO3H}}
			:{{chem2|CH3(CH2)10CH2OSO3H + NaOH→CH3(CH2)10CH2OSO3Na + H2O}}
			Dodecanol is used as an ]. It is also the precursor to ], an important fragrance, and ], an ] for improving the ] of organic molecules.
⚫	==Toxicity==
⚫	Dodecanol is a mild skin irritant. It has about half the toxicity of ], but it is very harmful to marine organisms.<ref></ref>
		⚫	== Toxicity ==
		⚫	Dodecanol can irritate the skin. It has about half the toxicity of ], 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==		== Mutual solubility with water==
	The mutual ] 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>		The mutual ] 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"		:{| class="wikitable sortable"
	|+'''Mutual Solubility of Water and 1-Dodecanol (98%, Melting Point 24&nbsp;°C), Weight %'''		|+'''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		!Temperature (°C) !! Solubility of dodecanol in water !! Solubility of water in dodecanol
	|-		|-
	| 29.5 || 0.04 || 2.87		| 29.5 || 0.04 || 2.87
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	|}		|}
	==References==		== References ==
	{{Reflist}}		{{Reflist}}
	==External links==		== External links ==
	*		*
	*		*
	{{Alcohols}}		{{Alcohols}}
			{{Authority control}}
⚫	]
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	]