Benzyl alcohol
{{Short description|Aromatic alcohol}}
{{Distinguish|benzoic acid|cresol|phenol}}
{{Use dmy dates|date=April 2020}}
{{Chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 443418046
|Name = Benzyl alcohol
|ImageFile = alkohol_benzylowy.svg
|ImageSize = 150px
|ImageName = Benzyl alcohol
|ImageFile1 = Benzyl-alcohol-3D-vdW.png
|ImageSize1 = 100px
|ImageName1 = Benzyl alcohol
|PIN = Phenylmethanol
(Hydroxymethyl)benzene
|OtherNames = Benzyl alcohol
α-Cresol
α-Toluenol
α-Hydroxytoluene
alpha-Hydroxyphenylmethane
Phenylcarbinol
Benzenemethanol
Benzyl hydroxide
|Section1={{Chembox Identifiers
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = LKG8494WBH
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = D00077
|InChI = 1/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
|InChIKey = WVDDGKGOMKODPV-UHFFFAOYAH
|SMILES1 = c1ccc(cc1)CO
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 720
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = WVDDGKGOMKODPV-UHFFFAOYSA-N
|CASNo = 100-51-6
|CASNo_Ref = {{cascite|correct|CAS}}
|EINECS = 202-859-9
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 13860335
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 17987
|SMILES = c1ccc(cc1)CO
|PubChem = 244
|RTECS = DN3150000
}}
|Section2={{Chembox Properties
|C=7 | H=8 | O=1
|Appearance = Colorless liquid
|Odor = Slightly aromatic
|Density = 1.044 g/cm3
|MeltingPtC = -15.2
|BoilingPtC = 205.3
|VaporPressure = 0.18 kPa (60 °C)
|Solubility = 3.50 g/100 mL (20 °C)
4.29 g/100 mL (25 °C)
|SolubleOther = Miscible with benzene, methanol, chloroform, ethanol, ether, acetone
|Solvent = other solvents
|RefractIndex = 1.5396
|LogP = 1.10
|pKa = 15.40
|Viscosity = 5.474 cP
|Dipole = 1.67 D
|MagSus = −71.83·10−6 cm3/mol
}}
|Section3={{Chembox Thermochemistry
|DeltaHf = −352 kJ/mol
|Entropy = 217.8 J/(K·mol)
}}
|Section4={{Chembox Hazards
|FlashPtC = 93
|AutoignitionPtC = 436
|ExploLimits = 1.3–13%
|ExternalSDS = [http://hazard.com/msds/mf/baker/baker/files/b1885.htm External MSDS]
|LD50 = 1250 mg/kg (rat, oral)
|NFPA-H = 1 | NFPA-F = 1 | NFPA-R = 0
}}
|Section5={{Chembox Pharmacology
|ATCCode_prefix = P03
|ATCCode_suffix = AX06
}}
}}
Benzyl alcohol (also known as α-cresol) is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is useful as a solvent for its polarity, low toxicity, and low vapor pressure. Benzyl alcohol has moderate solubility in water (4 g/100 mL) and is miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.
Natural occurrences
Benzyl alcohol is produced naturally by many plants and is commonly found in fruits and teas. It is also found in a variety of essential oils including jasmine, hyacinth and ylang-ylang.{{Merck11th|1138}} It is also found in castoreum from the castor sacs of beavers.{{Cite book | title = The Beaver: Its Life and Impact | author = Dietland Muller-Schwarze | year = 2003 | page = 43 | publisher = Cornell University Press | isbn = 978-0-8014-5010-5 | url = https://books.google.com/books?id=HZ5WjXB5Pr8C&q=Castoreum%20beekeeping&pg=PA43}} Benzyl esters also occur naturally.{{cite journal |doi=10.1104/pp.006460|title=Characterization of an Acyltransferase Capable of Synthesizing Benzylbenzoate and Other Volatile Esters in Flowers and Damaged Leaves of Clarkia breweri|year=2002|last1=d'Auria|first1=John C.|last2=Chen|first2=Feng|last3=Pichersky|first3=Eran|journal=Plant Physiology|volume=130|issue=1|pages=466–476|pmid=12226525|pmc=166578}}
Preparation
Benzyl alcohol is produced industrially from toluene via benzyl chloride, which is hydrolyzed:
: C6H5CH2Cl + H2O → C6H5CH2OH + HCl
Another route entails hydrogenation of benzaldehyde, a by-product of the oxidation of toluene to benzoic acid.{{Ullmann|author=Friedrich Brühne|author2=Elaine Wright|title=Benzyl Alcohol|year=2007|doi=10.1002/14356007.a04_001}}
For laboratory use, Grignard reaction of phenylmagnesium bromide (C6H5MgBr) with formaldehyde and the Cannizzaro reaction of benzaldehyde also give benzyl alcohol. The latter also gives benzoic acid, an example of an organic disproportionation reaction.
Reactions
Like most alcohols, it reacts with carboxylic acids to form esters. In organic synthesis, benzyl esters are popular protecting groups because they can be removed by mild hydrogenolysis.{{OrgSynth | last1 = Furuta | first1 = Kyoji | last2 = Gao | first2 = Qing-Zhi | last3 = Yamamoto | first3 = Hisashi | title = Chiral (Acyloxy)borane Complex-Catalyzed Asymmetric Diels-Alder Reaction: (1R)-1,3,4-Trimethyl-3-Cyclohexene-1-Carboxaldehyde | prep = cv9p0722 | volume = 72 | page = 86 | year = 1995 | collvol = 9 | collvolpages = 722}}
Benzyl alcohol reacts with acrylonitrile to give N-benzylacrylamide. This is an example of a Ritter reaction:{{OrgSynth | last = Parris | first = Chester L. | title = N-benzylacrylamide | prep = cv5p0073 | volume = 42 | page = 16 | year = 1962 | collvol = 5 | collvolpages = 73}}
:C6H5CH2OH + NCCHCH2 → C6H5CH2N(H)C(O)CHCH2
Applications
Benzyl alcohol is used as a general solvent for inks, waxes, shellacs, paints, lacquers, and epoxy resin coatings. Thus it can be used in paint strippers, especially when combined with compatible viscosity enhancers to encourage the mixture to cling to painted surfaces.{{citation | url = http://www.chemicalland21.com/industrialchem/solalc/BENZYL%20ALCOHOL.htm | title = Benzyl alcohol | publisher = chemicalland21.com | access-date = 2006-05-14 | archive-url = https://web.archive.org/web/20090421060841/http://chemicalland21.com/industrialchem/solalc/BENZYL%20ALCOHOL.htm | archive-date = 2009-04-21 }}
It is a precursor to a variety of esters and ethers, used in the soap, perfume, and flavor industries. E.g. benzyl benzoate, benzyl salicylate, benzyl cinnamate, dibenzyl ether, benzyl butyl phthalate.
It can be used as a local anesthetic, especially with epinephrine.{{Cite journal |last1=Wilson |first1=L. |last2=Martin |first2=S. |date=May 1999 |title=Benzyl alcohol as an alternative local anesthetic |journal=Annals of Emergency Medicine |volume=33 |issue=5 |pages=495–499 |doi=10.1016/s0196-0644(99)70335-5 |pmid=10216324}}
As a dye solvent, it enhances the process of dying wool, nylon, and leather.{{cite book |author1=Michael Ash |author2=Irene Ash |title=Handbook of Preservatives |url=https://books.google.com/books?id=XZ2QB7bu5LwC&pg=PA487 |year=2004 |publisher=Synapse Info Resources |isbn=978-1-890595-66-1 |page=292}}
= Use in health care =
Benzyl alcohol is used as a bacteriostatic preservative at low concentration in intravenous medications, cosmetics, and topical drugs.{{cite journal |author=H. A. Mashayekhi |author2=M. Rezaee |author3=Sh. S. Garmaroudi |author4=N. Montazeri |author5=S. J. Ahmadi |title=Rapid and sensitive determination of benzaldehyde arising from benzyl alcohol used as preservative in an injectable formulation solution using dispersive liquid–liquid microextraction followed by gas chromatography |journal=Anal. Sci.
|volume=27 |issue=8 |pages=865–868 |year=2011 |doi=10.2116/analsci.27.865|pmid=21828928 |doi-access=free }}
Benzyl alcohol, sold under the brand name Ulesfia, was approved by the U.S. Food and Drug Administration (FDA) in 2009, as a 5% solution for the treatment of head lice in people 6 months of age and older.{{cite web | title=Ulesfia- benzyl alcohol lotion | website=DailyMed | date=8 April 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5754f979-32b7-4406-a3a9-ed36aac6a37a | access-date=27 April 2020}} It affects the louse's spiracles, preventing them from closing. These then become clogged with water or mineral oil or other matter and cause the insect to die from asphyxiation.
Benzyl alcohol is used effectively for treating lice infestations as the active ingredient in lotion shampoo with 5% benzyl alcohol.
Benzyl alcohol is an ingredient used in the manufacture of soaps, topical creams, skin lotions, shampoos, and facial cleansers and is popular due to its anti-bacterial and anti-fungal properties. It is a common ingredient in a variety of household products.
Safety
Sensitization to benzyl alcohol occurs very rarely, mainly in patients with stasis dermatitis.{{Cite web |title=Registration Dossier - ECHA |url=https://echa.europa.eu/registration-dossier/-/registered-dossier/14748/7/5/1 |access-date=2023-04-20 |website=echa.europa.eu |language=en-GB}}
Benzyl alcohol is not considered to be a carcinogen, and no data are available regarding teratogenic or reproductive effects.
Benzyl alcohol has low acute toxicity with an {{LD50}} of 1.2 g/kg in rats. It oxidizes rapidly in healthy individuals to benzoic acid, conjugated with glycine in the liver, and excreted as hippuric acid. Very high concentrations can result in toxic effects including respiratory failure, vasodilation, hypotension, convulsions, and paralysis.
Benzyl alcohol is toxic to neonates and is associated with the gasping syndrome.{{citation | editor=Jerrold B. Leikin | editor2=Frank P. Paloucek | author=Carl R. Baum | contribution=Examples of mass exposures involving the pediatric population | title=Poisoning and Toxicology Handbook | edition=4th | publisher=Informa | year=2008 | page=726}}.{{citation | author=Juan Gershanik | title=The gasping syndrome and benzyl alcohol poisoning | journal=N Engl J Med | year=1982 | volume=307 | issue=22 | pages=1384–8 | doi=10.1056/nejm198211253072206|display-authors=etal | pmid=7133084}}.{{cite journal |last1=Clouser |first1=Amanda |last2=Diseroad |first2=Emily |title=Harmful excipients for pediatric patients |journal=Contemporary Pediatrics |date=2022-02-11 |volume=39 |issue=1 |url=https://www.contemporarypediatrics.com/view/harmful-excipients-for-pediatric-patients |access-date=1 October 2024}}
References
{{reflist}}
External links
- {{ICSC|0833|08}}
{{Alcohols }}
{{Portal bar | Medicine}}
{{Authority control}}