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`Fatty alcohol - Wikipedia. the free encyclopedia
`
`Fatty alcohol
`
`From Wikipedia, the free encyclopedia
`
`Fatty alcohols (or long-chain alcohols) are usually high-molecular-
`weight, straight-chain primary alcohols, but can also range from as
`few as 4-6 carbons to as many as 22-26, derived from natural fats
`and oils. The precise chain length varies with the source.[1][2] Some
`commercially important fatty alcohols are lauryl, stearyl, and oleyl
`alcohols. They are colourless oily liquids (for smaller carbon numbers) or waxy solids, although impure
`samples may appear yellow. Fatty alcohols usually have an even number of carbon atoms and a single
`alcohol group (-OH) attached to the terminal carbon. Some are unsaturated and some are branched. They
`are widely used in industry. As with fatty acids, they are often referred to generically by the number of
`carbon atoms in the molecule, such as "a C12 alcohol”, that is an alcohol having 12 carbons, for example
`dodecanol.
`
`H30-(C H2)n—C H2‘O H
`
`Fatty alcohol
`
`Contents
`
`I
`
`1 Production and occurrence
`
`I 1.1 From natural sources
`
`I 1.2 From petrochemical sources
`
`I 2 Applications
`
`I 2.1 Nutrition
`
`I 3 Safety
`
`I 3.1 Human Health
`
`I 3.2 Environment
`
`I 3.3 Aquatic Organisms
`
`I 4 Common names and related compounds
`
`I 5 References
`
`I 6 External links
`
`Production and occurrence
`
`Most fatty alcohols in nature are found as waxes which are esters with fatty acids and fatty alcoholsm They
`are produced by bacteria, plants and animals for purposes of buoyancy, as source of metabolic water and
`energy, biosonar lenses (marine mammals) and for thermal insulation in the form of waxes (in plants and
`insects).[3] Fatty alcohols were unavailable until the early 1900s They were originally obtained by
`reduction of wax esters with sodium by the Bouveault—Blanc reduction process. In the 1930s catalytic
`hydrogenation was commercialized, which allowed the conversion of fatty acid esters, typically tallow, to
`
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`the alcohols. In the 1940s and 1950s, petrochemicals became an important source of chemicals, and Karl
`Ziegler had discovered the polymerization of ethylene. These two developments opened the way to
`synthetic fatty alcohols.
`
`From natural sources
`
`The traditional sources of fatty alcohols have largely been various vegetable oils and these remain a large-
`scale feedstock. Animal fats (tallow) were of historic importance, particularly whale oil, however they are
`no longer used on a large scale. Tallows produce a fairly narrow range of alcohols, predominantly C16-
`C18, the chain lengths from plant sources are more variable (C6-C24) making them the preferred source.
`The alcohols are isolated from the triglycerides (fatty acid triesters), which form the bulk of the oil, by
`transesterification to give methyl esters which in turn are hydrogenated to the alcohols. Higher alcohols
`(C20-C22) can be obtained from rapeseed oil or mustard seed oil. Midcut alcohols are obtained from
`coconut oil (C 12-C 14) or palm kernel oil (C16-C18).
`
`From petrochemical sources
`
`Fatty alcohols are also prepared from petrochemical sources. In the Ziegler process, ethylene is
`oligomerized using triethylaluminium followed by air oxidation. This process affords even-numbered
`alcohols:
`
`A1(C2H5)3 + 18 C2H4 —’ A1(C14H29)3
`
`A1(C14H29)3 + 1.5 02 + 1.5 H20 —> 3 HOC14H29 + 0.5 A1203
`
`Alternatively ethylene can be oligomerized to give mixtures of alkenes, which are subjected to
`hydroformylation, this process affording odd-numbered aldehyde, which is subsequently hydrogenated. For
`example, from l-decene, hydroformylation gives the C11 alcohol:
`
`C8H17CH=CH2 + H2 + CO —> C8H17CH2CH2CHO
`
`C8H17CH2CH2CHO + H2 —> C8H17CH2CH2CH2OH
`
`In the Shell higher olefin process, the chain-length distribution in the initial mixture of alkene oligomers is
`adjusted so as to more closely match market demand. Shell does this by means of an intermediate
`metathesis reaction.[4] The resultant mixture is fractionated and hydroformylated/hydrogenated in a
`subsequent step.
`
`Applications
`
`Fatty alcohols are mainly used in the production of detergents and surfactants. They are components also of
`cosmetics, foods, and as industrial solvents. Due to their amphipathic nature, fatty alcohols behave as
`nonionic surfactants. They find use as emulsifiers, emollients and thickeners in cosmetics and food
`industry. About 50% of fatty alcohols used commercially are of natural origin, the remainder being
`synthetic. [1]
`
`Nutrition
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`Very long chain fatty alcohols (VLCFA), obtained from plant waxes and beeswax have been reported to
`lower plasma cholesterol in humans. They can be found in unrefined cereal grains, beeswax, and many
`plant-derived foods. Reports suggest that 5—20 mg per day of mixed C24—C34 alcohols, including
`octacosanol and triacontanol, lower low-density lipoprotein (LDL) cholesterol by 21%—29% and raise high-
`density lipoprotein cholesterol by 8%—15%. Wax esters are hydrolyzed by a bile salt—dependent pancreatic
`carboxyl esterase, releasing long chain alcohols and fatty acids that are absorbed in the gastrointestinal
`tract. Studies of fatty alcohol metabolism in fibroblasts suggest that very long chain fatty alcohols, fatty
`aldehydes, and fatty acids are reversibly inter-converted in a fatty alcohol cycle. The metabolism of these
`compounds is impaired in several inherited human peroxisomal disorders, including adrenoleukodystrophy
`and SjOgren-Larsson syndrome.[5]
`
`Safety
`
`Human Health
`
`Fatty alcohols are relatively benign materials, with LDSOs (oral, rat) ranging from 3.1-r g/kg for hexanol to
`6 -8 g/kg for octadecanollll For a 50 kg person, these values translate to more than 100 g. Tests of acute
`and repeated exposures have revealed a low level of toxicity from inhalation, oral or dermal exposure of
`fatty alcohols. Fatty alcohols are not very volatile and the acute lethal concentration is greater than the
`saturated vapor pressure. Longer chain (C12-C16) fatty alcohols produce fewer health effects than short
`chain (< C12). Short chain fatty alcohols are considered eye irritants, while long chain alcohols are not.[6]
`Fatty alcohols exhibit no skin sensitizationm
`
`Repeated exposure to fatty alcohols produce low level toxicity and certain compounds in this category can
`cause local irritation on contact or low-grade liver effects (essentially linear alcohols have a slightly higher
`rate of occurrence of these effects). N0 effects on the central nervous system have been seen with inhalation
`and oral exposure. Tests of repeated bolus dosages of l-hexanol and l-octanol showed potential for CNS
`depression and induced respiratory distress. No potential for peripheral neuropathy has been found. In rats,
`the no observable adverse effect level (NOAEL) ranges from 200 mg/kg/day to 1000 mg/kg/day by
`ingestion. There has been no evidence that fatty alcohols are carcinogenic, mutagenic, or cause reproductive
`toxicity or infertility. Fatty alcohols are effectively eliminated from the body when exposed, limiting
`possibility of retention or bioaccumulation.[7]
`
`Margins of exposure resulting from consumer uses of these chemicals are adequate for the protection of
`human health as determined by the Organization for Economic Co-operation and Development (OECD)
`high production volume chemicals program.[6][8]
`
`Environment
`
`Fatty alcohols up to chain length C18 are biodegradable, with length up to C16 biodegrading within 10 days
`completely. Chains C16 to C18 were found to biodegrade from 62% to 76% in 10 days. Chains greater than
`C18 were found to degrade by 37% in 10 days. Field studies at waste-water treatment plants have shown
`that 99% of fatty alcohols lengths C12-C18 are removedm
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`Fate prediction using fugacity modeling has shown that fatty alcohols with chain lengths of C10 and greater
`in water partition into sediment. Lengths C14 and above are predicted to stay in the air upon release.
`Modeling shows that each type of fatty alcohol will respond independently upon environmental releasem
`
`Aquatic Organisms
`
`Fish, invertebrates and algae experience similar levels of toxicity with fatty alcohols although it is
`dependent on chain length with the shorter chain having greater toxicity potential. Longer chain lengths
`show no toxicity to aquatic organismsm
`
`Chain Size Acute Toxicity for fish Chronic Toxicity for fish
`
`<011
`
`1—100mg/l
`
`0.1-1.0mg/l
`
`C11-C13
`
`0.1-1.0mg/l
`
`0.1 -<1.0 mg/l
`
`C14-C15 NA
`
`>C16
`
`NA
`
`0.01 mg/l
`
`NA
`
`This category of chemicals was evaluated under the Organization for Economic Co-operation and
`Development (OECD) high production volume chemicals program. No unacceptable environmental risks
`were identified. [8]
`
`Common names and related compounds
`
`Name
`
`tert-Butyl alcohol
`
`tert—Amyl alcohol
`
`3-Methyl-3-pentanol
`
`Ethchlorvynol
`
`l-Octanol (capryl alcohol)
`
`2-ethy1 hexanol
`
`pelargonic alcohol (l-nonanol)
`l-Decanol (decyl alcohol, capric alcohol)
`
`Undecyl alcohol (1-undecanol, undecanol,
`Hendecanol)
`
`Lauryl alcohol (Dodecanol, l-dodecanol)
`
`Tridecyl alcohol (l-tridecanol, tridecanol,
`isotridecanol)
`
`Myristyl alcohol (1-tetradecanol)
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`Carbon atoms Branches/saturated? Formula
`
`C4H100
`
`C5H120
`
`C6H14O
`
`C7H9C10
`
`CnggO
`
`4 carbon atoms
`
`5 carbon atoms
`
`6 carbon atoms
`
`7 carbon atoms
`
`8 carbon atoms
`
`8 carbon atoms branched
`
`9 carbon atoms
`ifofigbon
`
`11 carbon
`atoms
`
`ifofisrbon
`
`13 carbon
`atoms
`
`igfiasrbon
`
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`unsaturated
`
`unsaturated
`
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`Fatty alcohol - Wikipedia. the free encyclopedia
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`Pentadecyl alcohol (l-pentadecanol, pentadecanol)
`
`cetyl alcohol (l-hexadecanol)
`
`palmitoleyl alcohol (cis-9-hexadecen- 1 -ol)
`
`Heptadecyl alcohol (l-n—heptadecanol, heptadecanol)
`
`stearyl alcohol (l-octadecanol)
`
`Nonadecyl alcohol (l-nonadecanol)
`
`arachidyl alcohol (l-eicosanol)
`
`Heneicosyl alcohol (l-heneicosanol)
`
`behenyl alcohol (l-docosanol)
`
`erucyl alcohol (cis- 1 3-docosen- 1 -ol)
`
`lignoceryl alcohol (1-tetracosanol)
`
`ceryl alcohol (l-hexacosanol)
`
`l-heptacosanol
`
`montanyl alcohol, cluytyl alcohol, or l-octacosanol
`
`l-nonacosanol
`
`myricyl alcohol, melissyl alcohol, or l-triacontanol
`
`l-dotriacontanol
`
`geddyl alcohol (l-tetratriacontanol)
`
`Cetearyl alcohol
`
`References
`
`15 carbon
`
`atoms
`
`16 carbon
`
`atoms
`
`16 carbon
`
`atoms
`
`17 carbon
`
`atoms
`
`18 carbon
`
`atoms
`
`19 carbon
`
`atoms
`
`20 carbon
`
`atoms
`
`21 carbon
`
`atoms
`
`22 carbon
`
`atoms
`
`22 carbon
`
`atoms
`
`24 carbon
`
`atoms
`
`26 carbon
`
`atoms
`
`27 carbon
`atoms
`
`28 carbon
`
`atoms
`
`29 carbon
`
`atoms
`
`30 carbon
`
`atoms
`
`32 carbon
`
`atoms
`
`34 carbon
`
`atoms
`
`C32H66O
`
`l. Klaus Noweck, Wolfgang Grafahrend, "Fatty Alcohols" in Ullmann's Encyclopedia of Industrial Chemistry 2006,
`
`Wiley-VCH, Weinheim. doi: 10. 1002/ 14356007.a10_277.pub2
`
`httptflenwi kipediaorg’wi kilFatty_alcohol
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`1,4 GROUP, INC.
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`Exhibit 1017
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`Fatty alcohol - Wikipedia, the free encyclopedia
`
`(https://dx.doi.org/ 10. 1002%2F14356007.a10_277.pub2)
`
`http://goldbook.iupac.org/FO2330.html
`
`Stephen Mudge; Wolfram Meier-Augenstein, Charles Eadsforth and Paul DeLeo (2010). "What contribution do
`
`detergent fatty alcohols make to sewage discharges and the maine environment?". Journal of Environmental
`
`Monitoring: 1846—1856. doi:10.1039/COEM00079E (https://dx.doi.org/10.1039%2FCOEM00079E).
`
`Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 6706—6711
`
`. Nutritional Significance and Metabolism of Very Long Chain Fatty Alcohols and Acids from Dietary Waxes —
`
`Hargrove et al. 229 (3): 215 - Experimental Biology and Medicine
`
`(http://www.ebmonline.org/cgi/content/abstract/229/3/215)
`
`Veenstra, Gauke; Catherine Webb, Hans Sanderson, Scott E. Belanger, Peter Fisk, Allen Nielson, Yutaka Kasai,
`
`Andreas Willing, Scott Dyer, David Penney, Hans Certa, Kathleen Stanton, Richard Sedlak (2009). "Human
`
`health risk assessment of long chain alcohols". Ecotoxicology and Environmental Safety: 1016—1030.
`
`doi:10.1016/j.ecoenv.2008.07.012 (https://dx.doi.org/10.1016%2Fj.ecoenv.2008.07.0l2).
`
`UK/ICCA (2006). "SIDS Initial Assessment Profile" (http://webnet.oecd.org/hpv/UI/handler.axd?id=03441f78-
`
`d135-4cab-b832-edfb1d0d677e). 0ECD Existing Chemicals Database.
`
`Sanderson, Hans; Scott E. Belanger, Peter R. Fisk, Christoph Schafers, Gauke Veenstra, Allen M. Nielsen,
`
`Yutaka Kasai, Andreas Willing, Scott D. Dyer, Kathleen Stanton, Richard Sedlak, (May 2009). "An overview of
`
`hazard and risk assessment of the OECD high production volume chemical category—Long chain alcohols [C6—
`
`C22] (LCOH)". Ecotoxz'cology and Environmental Safety 72 (4): 973—979. doi: 10. 1016/j.ecoenv.2008. 10.006
`
`(https://dx.doi.org/10.1016%2Fj.ecoenv.2008.10.006).
`
`External links
`
`Cyberlipid. "Fatty Alcohols and Aldehydes" (http://www.cyberlipid.org/simple/simp0003.htm).
`
`Retrieved 2007-02-06. General overview of fatty alcohols, with references.
`
`CONDEA. "Dr. Z Presents All about fatty alcohols"
`
`(http://www.zenitech.com/documents/new%20pdfs/articles/All%20about%20fatty%20alcohols%20C
`
`ondea.pdf) (PDF). Retrieved 2007-02-06.
`
`Retrieved from "http://en.wikipedia.org/w/index.php?title=Fatty_a1cohol&oldid=655 1 14159"
`
`Categories: Fatty alcohols Lipids Commodity chemicals
`
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