Fatty alcohol

Short description: Class of chemical compounds

An example of a fatty alcohol, oleyl alcohol

Fatty alcohols (or long-chain alcohols) are usually high-molecular mass, straight-chain primary alcohols, but can also range from as few as 4–6 carbon atoms 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 alcohol. 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 carbon atoms, for example dodecanol.

## Contents

* 1 Production and occurrence
* 1.1 From natural sources
* 1.2 From petrochemical sources
* 2 Applications
* 3 Nutrition
* 4 Safety
* 4.1 Human health
* 4.2 Environment
* 4.3 Aquatic organisms
* 5 Table with common names
* 6 References
* 7 External links

## Production and occurrence

Fatty alcohols became commercially available in 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 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. As of 2005, about 50% of fatty alcohols used commercially are of natural origin, the remainder being synthetic (petrochemical).[1]

### From natural sources

Most fatty alcohols in nature are found as waxes, which are esters of fatty acids and fatty alcohols.[1] 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] The traditional sources of fatty alcohols have largely been various vegetable oils, which 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, while plant sources produce a wider range of alcohols (C6–C24), making them the preferred source. The alcohols are obtained from the triglycerides (fatty acid triesters), which form the bulk of the oil. The process involves the transesterification of the triglycerides to give methyl esters which are then hydrogenated to produce fatty alcohols.[4] Higher alcohols (C20–C22) can be obtained from rapeseed oil or mustard seed oil. Midcut alcohols are obtained from coconut oil (C12–C14) 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:

Al(C2H5)3 \+ 18 C2H4 → Al(C14H29)3
Al(C14H29)3 \+ ​3⁄2 O2 \+ ​3⁄2 H2O → 3 HOC14H29 \+ ​1⁄2 Al2O3

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 1-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.[5] 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. Being viscous and immiscible with water, they find use as co-emulsifiers, emollients, and thickeners in cosmetics and food industry.[1]

Fatty alcohol are converted to their ethoxylates by treatment with ethylene oxide:[6]

RCH
2OH + n C

4O → RCH
2(OCH
2CH

nOH

The resulting fatty alcohol ethoxylates are important surfactants.[7] They are named after the parent fatty alcohol (such as lauryl alcohol and stearyl alcohol) with an "eth" suffix, i.e., laureth and steareth.[8] These terms are followed by an index for the average number of ethoxylate groups; for example, laureth-20 denotes an ethoxylated lauryl alcohol with about 20 ethoxy units on average and has the formula CH
3(CH

10CH
2(OCH
2CH

20OH.[8]

Fatty alcohols are precursors to another large class of surfactants, the sodium alkyl sulfates such as sodium dodecyl sulfate (SDS). Five million tons of SDS and related materials are produced annually by sulfation of dodecyl alcohol and related fatty alcohols.[6]

## Nutrition

The metabolism of fatty alcohols is impaired in several inherited human peroxisomal disorders, including adrenoleukodystrophy and Sjögren–Larsson syndrome.[9]

## Safety

### Human health

Fatty alcohols are relatively benign materials, with LD50 (oral, rat) ranging from 3.1–4 g/kg for hexanol to 6–8 g/kg for octadecanol.[1] 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 (smaller than C12). Short-chain fatty alcohols are considered eye irritants, while long chain alcohols are not.[10] Fatty alcohols exhibit no skin sensitization.[11]

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). No effects on the central nervous system have been seen with inhalation and oral exposure. Tests of repeated bolus dosages of 1-hexanol and 1-octanol showed potential for CNS depression and induced respiratory distress. No potential for peripheral neuropathy has been found. In rats, the no observed 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 mutagenic or cause reproductive toxicity or infertility. Fatty alcohols are effectively eliminated from the body when exposed, limiting possibility of retention or bioaccumulation.[11]

Margins of exposure resulting from consumer uses of these chemicals are adequate for the protection of human health as determined by the Organisation for Economic Co-operation and Development (OECD) high production volume chemicals program.[10][12]

### 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 in rates ranging from 62% to 76% in 10 days. Chains greater than C18 were found to degrade by 37% in 10 days. Field studies at wastewater treatment plants have shown that 99% of fatty alcohols of lengths C12–C18 are removed.[11]

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 release.[11]

### 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 organisms.[11]

Chain size | Acute toxicity for fish | Chronic toxicity for fish

|
|

<C11 | 1–100 mg/L | 0.1–1.0 mg/L
C11–C13 | 0.1–1.0 mg/L | 0.1–<1.0 mg/L
C14–C15 | — | 0.01 mg/L
>C16 | – | –

This category of chemicals was evaluated under the Organisation for Economic Co-operation and Development (OECD) high production volume chemicals program. No unacceptable environmental risks were identified.[12]

## Table with common names

This table lists some alkyl alcohols. Note that in general the alcohols with even numbers of carbon atoms have common names, since they are found in nature, whereas those with odd numbers of carbon atoms generally do not have a common name.

Name | Carbon atoms | Branches/saturation | Formula

|
|
|

tert-Butyl alcohol | 4 carbon atoms | branched | C4H10O
tert-Amyl alcohol | 5 carbon atoms | branched | C5H12O
3-Methyl-3-pentanol | 6 carbon atoms | branched | C6H14O
1-Heptanol (enanthic alcohol) | 7 carbon atoms |  | C7H16O
1-Octanol (capryl alcohol) | 8 carbon atoms |  | C8H18O
Pelargonic alcohol (1-nonanol) | 9 carbon atoms |  | C9H20O
1-Decanol (decyl alcohol, capric alcohol) | 10 carbon atoms |  | C10H22O
Undecyl alcohol (1-undecanol, undecanol, Hendecanol) | 11 carbon atoms |  | C11H24O
Lauryl alcohol (dodecanol, 1-dodecanol) | 12 carbon atoms |  | C12H26O
Tridecyl alcohol (1-tridecanol, tridecanol, isotridecanol) | 13 carbon atoms |  | C13H28O
Myristyl alcohol (1-tetradecanol) | 14 carbon atoms |  | C14H30O
Pentadecyl alcohol (1-pentadecanol, pentadecanol) | 15 carbon atoms |  | C15H32O
Cetyl alcohol (1-hexadecanol) | 16 carbon atoms |  | C16H34O
Palmitoleyl alcohol (cis-9-hexadecen-1-ol) | 16 carbon atoms | unsaturated | C16H32O
Heptadecyl alcohol (1-n-heptadecanol, heptadecanol) | 17 carbon atoms |  | C17H36O
Stearyl alcohol (1-octadecanol) | 18 carbon atoms |  | C18H38O
Oleyl alcohol (1-octadecenol) | 18 carbon atoms | unsaturated | C18H36O
Nonadecyl alcohol (1-nonadecanol) | 19 carbon atoms |  | C19H40O
Arachidyl alcohol (1-eicosanol) | 20 carbon atoms |  | C20H42O
Heneicosyl alcohol (1-heneicosanol) | 21 carbon atoms |  | C21H44O
Behenyl alcohol (1-docosanol) | 22 carbon atoms |  | C22H46O
Erucyl alcohol (cis-13-docosen-1-ol) | 22 carbon atoms | unsaturated | C22H44O
Lignoceryl alcohol (1-tetracosanol) | 24 carbon atoms |  | C24H50O
Ceryl alcohol (1-hexacosanol) | 26 carbon atoms |  | C26H54O
1-Heptacosanol | 27 carbon atoms |  | C27H56O
Montanyl alcohol, cluytyl alcohol, or 1-octacosanol | 28 carbon atoms |  | C28H58O
1-Nonacosanol | 29 carbon atoms |  | C29H60O
Myricyl alcohol, melissyl alcohol, or 1-triacontanol | 30 carbon atoms |  | C30H62O
1-Dotriacontanol (Lacceryl alcohol) | 32 carbon atoms |  | C32H66O
Geddyl alcohol (1-tetratriacontanol) | 34 carbon atoms |  | C34H70O

## References

1. ↑ 1.0 1.1 1.2 1.3 1.4 Noweck, Klaus; Grafahrend, Wolfgang. "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_277.pub2.
2. ↑ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006-) ""Fatty alcohol"". doi:10.1351/goldbook.F02330
3. ↑ Mudge, Stephen; Meier-Augenstein, Wolfram; Eadsforth, Charles; DeLeo, Paul (2010). "What contribution do detergent fatty alcohols make to sewage discharges and the marine environment?". Journal of Environmental Monitoring 12 (10): 1846–1856. doi:10.1039/C0EM00079E. PMID 20820625.
4. ↑ Kreutzer, Udo R. (February 1984). "Manufacture of fatty alcohols based on natural fats and oils". Journal of the American Oil Chemists' Society 61 (2): 343–348. doi:10.1007/BF02678792.
5. ↑ Ashford's Dictionary of Industrial Chemicals (3rd ed.). 2011. pp. 6706–6711. [ISBN missing]
6. ↑ 6.0 6.1 Holmberg, Krister (2019). "Surfactants". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–56. doi:10.1002/14356007.a25_747.pub2. ISBN 978-3-527-30673-2.
7. ↑ "Chapter 5: Non-ionic Surfactants". Chemistry and Technology of Surfactants. Oxford; Ames, Iowa: Blackwell Publishing Ltd. 2006. pp. 134-152 (236). ISBN 978-0-470-98859-6.
8. ↑ 8.0 8.1 "﻿INCI Nomenclature Conventions and Reference Information﻿". Personal Care Products Council.: 6. September 2023. https://www.personalcarecouncil.org/wp-content/uploads/2023/03/INCI-Nomenclature-Conventions-and-Reference-Information-2023.pdf. "Ethoxylated alcohols are named by adding the suffix “eth” to the conventional stem name followed by the average number of moles of ethylene oxide, e.g., Steareth-10."
9. ↑ Hargrove, James L.; Greenspan, Phillip; Hartle, Diane K. (2004). "Nutritional Significance and Metabolism of Very Long Chain Fatty Alcohols and Acids from Dietary Waxes". Exp. Biol. Med. (Maywood) 229 (3): 215–226. doi:10.1177/153537020422900301. PMID 14988513.
10. ↑ 10.0 10.1 Veenstra, Gauke; Webb, Catherine; Sanderson, Hans; Belanger, Scott E.; Fisk, Peter; Nielson, Allen; Kasai, Yutaka; Willing, Andreas et al. (2009). "Human health risk assessment of long chain alcohols". Ecotoxicology and Environmental Safety 72 (4): 1016–1030. doi:10.1016/j.ecoenv.2008.07.012. ISSN 0147-6513. PMID 19237197. Bibcode: 2009EcoES..72.1016V. https://pure.au.dk/portal/en/publications/human-health-risk-assessment-of-long-chain-alcohols-lcoh(0656c100-20d3-11dd-be51-000ea68e967b).html.
11. ↑ 11.0 11.1 11.2 11.3 11.4 UK/ICCA (2006). "SIDS Initial Assessment Profile". OECD Existing Chemicals Database. http://webnet.oecd.org/hpv/UI/handler.axd?id=03441f78-d135-4cab-b832-edfb1d0d677e.
12. ↑ 12.0 12.1 Sanderson, Hans; Belanger, Scott E.; Fisk, Peter R.; Schäfers, Christoph; Veenstra, Gauke; Nielsen, Allen M.; Kasai, Yutaka; Willing, Andreas et al. (May 2009). "An overview of hazard and risk assessment of the OECD high production volume chemical category—Long chain alcohols [C6–C22] (LCOH)". Ecotoxicology and Environmental Safety 72 (4): 973–979. doi:10.1016/j.ecoenv.2008.10.006. PMID 19038453. Bibcode: 2009EcoES..72..973S.

## External links

* IUPAC-IUB Commission on Biochemical Nomenclature (CBN), World Wide Web version Prepared by G. P. Moss. "Nomenclature of Lipids". https://iupac.qmul.ac.uk/lipid/.
* Cyberlipid. "Fatty Alcohols and Aldehydes". http://www.cyberlipid.org/simple/simp0003.htm. General overview of fatty alcohols, with references.
* CONDEA. "Dr. Z Presents All about fatty alcohols". http://www.zenitech.com/documents/new pdfs/articles/All about fatty alcohols Condea.pdf.

* v
* t
* e

Alcohols

Straight-chain
primary
alcohols (1°)|

* Methanol (C1)
* Ethanol (C2)
* 1-Propanol (C3)
* n-Butanol (C4)
* 1-Pentanol (C5)
* 1-Hexanol (C6)
* 1-Heptanol (C7)
* 1-Octanol (C8)
* 1-Nonanol (C9)
* 1-Decanol (C10)
* Undecanol (C11)
* Dodecanol (C12)
* Tridecan-1-ol (C13)
* 1-Tetradecanol (C14)
* 1-Pentadecanol (C15)
* Cetyl alcohol (C16)
* Heptadecan-1-ol (C17)
* Stearyl alcohol (C18)
* Nonadecan-1-ol (C19)
* Arachidyl alcohol (C20)
* Heneicosan-1-ol (C21)
* Docosanol (C22)
* Tricosan-1-ol (C23)
* 1-Tetracosanol (C24)
* Pentacosan-1-ol (C25)
* 1-Hexacosanol (C26)
* 1-Heptacosanol (C27)
* 1-Octacosanol (C28)
* 1-Nonacosanol (C29)
* Triacontanol (C30)
* Hentriacontanol (C31)
* Dotriacontanol (C32)
* Tritriacontanol (C33)
* Tetratriacontanol (C34)
* Pentatriacontanol (C35)
* Hexatriacontanol (C36)
* 1-Heptatriacontanol (C37)
* 1-Octatriacontanol (C38)
* Nonatriacontan-1-ol (C39)
* Tetracontanol (C40)

Other primary
alcohols|

* Isobutanol (C4)
* Isoamyl alcohol (C5)
* 2-Methyl-1-butanol (C5)
* Phenethyl alcohol (C8)
* Tryptophol (C10)

Secondary
alcohols (2°)|

* Isopropanol (C3)
* Cyclopropanol (C3)
* 2-Butanol (C4)
* 2-Pentanol (C5)
* 3-Pentanol (C5)
* Cyclopentanol (C5)
* 2-Hexanol (C6)
* 3-Hexanol (C6)
* Pinacolyl alcohol (C6)
* Cyclohexanol (C6)
* 2-Heptanol (C7)
* 3-Heptanol (C7)
* 2-Octanol (C8)

Tertiary
alcohols (3°)|

* tert-Butyl alcohol (C4)
* tert-Amyl alcohol (C5)
* 2-Methyl-2-pentanol (C6)
* 2-Methylhexan-2-ol (C7)
* 2-Methylheptan-2-ol (C8)
* 3-Methyl-3-pentanol (C6)
* 3-Methyloctan-3-ol (C9)

Preparations|

* Substitution of haloalkane
* Carbonyl reduction
* Ether cleavage
* Hydrolysis of epoxide
* Hydration of alkene
* Ziegler process

Reactions|

* Deprotonation
* Protonation
* Alcohol oxidation
* Glycol cleavage
* Nucleophilic substitution
* Fischer–Speier esterification
* Williamson ether synthesis
* Elimination reaction
* Nucleophilic substitution of carbonyl group
* Friedel-Crafts alkylation
* Nucleophilic conjugate addition
* Transesterification

* Category

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