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Dodecanol

April 21, 2024

Dodecanol /ˈdoʊˈdɛkɑːnɒl/, 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.[4]

Dodecanol[1]
Names
Preferred IUPAC name
Dodecan-1-ol
Other names
Dodecanol
1-Dodecanol
Dodecyl alcohol
Lauryl alcohol
Identifiers
  • 112-53-8 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28878 Y
ChEMBL
  • ChEMBL24722 Y
ChemSpider
  • 7901 Y
DrugBank
  • DB06894 Y
ECHA InfoCard 100.003.620
KEGG
  • C02277 Y
  • 8193
UNII
  • 178A96NLP2 Y
  • DTXSID5026918
  • InChI=1S/C12H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3 Y
    Key: LQZZUXJYWNFBMV-UHFFFAOYSA-N Y
  • InChI=1/C12H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3
    Key: LQZZUXJYWNFBMV-UHFFFAOYAU
  • OCCCCCCCCCCCC
Properties
C12H26O
Molar mass 186.339 g·mol−1
Appearance Colorless solid
Density 0.8309
Melting point 24 °C (75 °F; 297 K)
Boiling point 259 °C (498 °F; 532 K)
0.004 g/L[2]
Solubility in ethanol and diethyl ether Soluble
−147.70×10−6 cm3/mol
Related compounds
Related
Hazards
GHS labelling:[3]
Warning
H319, H410
P273, P305+P351+P338
Flash point 127 °C (261 °F; 400 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Production and use edit

In 1993, the European demand of dodecanol was around 60,000 tonnes per year. It can be obtained from palm oil or coconut oil fatty acids and methyl esters by hydrogenation.[5] It may also be produced synthetically via the Ziegler process. A classic laboratory method involves Bouveault-Blanc reduction of ethyl laurate.[4]

Dodecanol is used to make surfactants, lubricating oils, pharmaceuticals, in the formation of monolithic polymers and as a flavor enhancing food additive. In cosmetics, 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 edit

Dodecanol can irritate the skin. It has about half the toxicity of ethanol, but it is very harmful to marine organisms.[6]

Mutual solubility with water edit

The mutual solubility of 1-dodecanol and water has been quantified as follows.[7]

Mutual solubility of water and 1-dodecanol (98%, melting point 24 °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 edit

  1. ^ Merck Index, 12th Edition, 3464.
  2. ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ^ GHS: GESTIS 035500
  4. ^ a b Ford, S. G.; Marvel, C. S. (1930). "Lauryl Alcohol". Organic Syntheses. 10: 62. doi:10.15227/orgsyn.010.0062.
  5. ^ Noweck, Klaus; Grafahrend, Wolfgang (2006). "Fatty Alcohols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_277.pub2. ISBN 978-3527306732.
  6. ^ . Archived from the original on 2011-07-16. Retrieved 2009-06-14.
  7. ^ Richard Stephenson and James Stuart, "Mutual Binary Solubilities: Water-Alcohols and Water-Esters", J. Chem. Eng. Data, 1986, 31, 56-70.

External links edit

  • MSDS at J.T. Baker

April 21, 2024
dodecanol, ɑː, lauryl, alcohol, organic, compound, produced, industrially, from, palm, kernel, coconut, fatty, alcohol, sulfate, esters, lauryl, alcohol, especially, sodium, lauryl, sulfate, very, widely, used, surfactants, sodium, lauryl, sulfate, related, do. Dodecanol 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 4 Dodecanol 1 Names Preferred IUPAC name Dodecan 1 ol Other names Dodecanol1 DodecanolDodecyl alcoholLauryl alcohol Identifiers CAS Number 112 53 8 Y 3D model JSmol Interactive image ChEBI CHEBI 28878 Y ChEMBL ChEMBL24722 Y ChemSpider 7901 Y DrugBank DB06894 Y ECHA InfoCard 100 003 620 KEGG C02277 Y PubChem CID 8193 UNII 178A96NLP2 Y CompTox Dashboard EPA DTXSID5026918 InChI InChI 1S C12H26O c1 2 3 4 5 6 7 8 9 10 11 12 13 h13H 2 12H2 1H3 YKey LQZZUXJYWNFBMV UHFFFAOYSA N YInChI 1 C12H26O c1 2 3 4 5 6 7 8 9 10 11 12 13 h13H 2 12H2 1H3Key LQZZUXJYWNFBMV UHFFFAOYAU SMILES OCCCCCCCCCCCC Properties Chemical formula C 12H 26O Molar mass 186 339 g mol 1 Appearance Colorless solid Density 0 8309 Melting point 24 C 75 F 297 K Boiling point 259 C 498 F 532 K Solubility in water 0 004 g L 2 Solubility in ethanol and diethyl ether Soluble Magnetic susceptibility x 147 70 10 6 cm3 mol Related compounds Related DodecanalDodecanoic acid1 Bromododecane Hazards GHS labelling 3 Pictograms Signal word Warning Hazard statements H319 H410 Precautionary statements P273 P305 P351 P338 Flash point 127 C 261 F 400 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Production and use 2 Toxicity 3 Mutual solubility with water 4 References 5 External linksProduction and use editIn 1993 the European demand of dodecanol was around 60 000 tonnes per year It can be obtained from palm oil or coconut oil fatty acids and methyl esters by hydrogenation 5 It may also be produced synthetically via the Ziegler process A classic laboratory method involves Bouveault Blanc reduction of ethyl laurate 4 Dodecanol is used to make surfactants lubricating oils pharmaceuticals in the formation of monolithic polymers and as a flavor enhancing food additive In cosmetics 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 editDodecanol can irritate the skin It has about half the toxicity of ethanol but it is very harmful to marine organisms 6 Mutual solubility with water editThe mutual solubility of 1 dodecanol and water has been quantified as follows 7 Mutual solubility of water and 1 dodecanol 98 melting point 24 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 01References edit Merck Index 12th Edition 3464 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health GHS GESTIS 035500 a b Ford S G Marvel C S 1930 Lauryl Alcohol Organic Syntheses 10 62 doi 10 15227 orgsyn 010 0062 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 3527306732 MSDS Safety Sheet Archived from the original on 2011 07 16 Retrieved 2009 06 14 Richard Stephenson and James Stuart Mutual Binary Solubilities Water Alcohols and Water Esters J Chem Eng Data 1986 31 56 70 External links editMSDS at Oxford MSDS at J T Baker Retrieved from https en wikipedia org w index php title Dodecanol amp oldid 1216558083, wikipedia, wiki, book, books, library,

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