Benzyl alcohol

Benzyl alcohol
Names
IUPAC name
Phenylmethanol
Other names
Phenylcarbinol
Identifiers
100-51-6 YesY
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:17987 YesY
ChEMBL ChEMBL720 YesY
ChemSpider 13860335 YesY
ECHA InfoCard 100.002.600
EC Number 202-859-9
E number E1519 (additional chemicals)
KEGG D00077 YesY
PubChem 244
RTECS number DN3150000
UNII LKG8494WBH YesY
Properties[1]
C7H8O
Molar mass 108.14 g·mol−1
Appearance Colorless liquid
Odor Slightly aromatic
Density 1.044 g cm−3
Melting point −15.2 °C (4.6 °F; 257.9 K)
Boiling point 205.3 °C (401.5 °F; 478.4 K)
3.50 g/100 mL (20 °C)
4.29 g/100 mL (25 °C)
Solubility in other solvents Soluble in benzene, methanol, chloroform, ethanol, ether, acetone
log P 1.10
Vapor pressure 0.18 kPa (60 °C)
Acidity (pKa) 15.40
1.5396
Viscosity 5.474 cP
1.67 D
Thermochemistry
217.8 J/K mol
-352 kJ/mol
Pharmacology
P03AX06 (WHO)
Hazards
Safety data sheet External MSDS
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
1
0
Flash point 93 °C (199 °F; 366 K)
436 °C (817 °F; 709 K)
Explosive limits 1.3–13%
Lethal dose or concentration (LD, LC):
1250 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Benzyl alcohol 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 a useful solvent due to its polarity, low toxicity, and low vapor pressure. Benzyl alcohol has moderate solubility in water (4 g/100 mL) and 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.[2]

It is also one of the chemical compounds found in castoreum from the castor sacs of beavers.[3]

Preparation

Benzyl alcohol is prepared by the hydrolysis of benzyl chloride using sodium hydroxide:

C6H5CH2Cl + NaOH → C6H5CH2OH + NaCl

It can also be prepared via a Grignard reaction by reacting phenylmagnesium bromide (C6H5MgBr) with formaldehyde, followed by acidification.

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.[4]

Benzyl alcohol reacts with acrylonitrile to give N-benzylacrylamide. This is an example of a Ritter reaction:[5]

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.[6] It is a precursor to a variety of esters, used in the soap, perfume, and flavor industries. It is also used in e-liquid for e-cigarettes to enhance the flavors used. When applied to damaged skin or mucous membranes at a 10% concentration it acts as a local anesthetic and antimicrobial agent, and is sometimes included as a degreaser in rug cleaning products. As a dye solvent, it enhances the process of dying wool, nylon, and leather.[7] It also has use as a photographic developer, and as an insect repellent.

Nanotechnological uses

Benzyl alcohol has been used as a dielectric solvent for the dielectrophoretic reconfiguration of nanowires.[8][9]

Use in health care

Benzyl alcohol is used as a bacteriostatic preservative at low concentration in intravenous medications, cosmetics and topical drugs.

The use of benzyl alcohol as a 5% solution has been approved by the U.S. FDA for the treatment of head lice in children older than 6 months and in adults.[10] 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.

Other uses

Benzyl alcohol has nearly the same refraction index of quartz and wool fiber. If a clear quartz object is immersed in benzyl alcohol, it becomes almost invisible. This test has been used to determine non-destructively whether an object is truly made of quartz (see crystal skull). Similarly, white wool immersed in benzyl alcohol also becomes almost invisible clearly revealing contaminants such as dark and medullated fibers and vegetable matter.

Safety

Benzyl alcohol has low acute toxicity with an LD50 of 1.2 g/kg in rats.[11] 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, it is associated with the gasping syndrome.[12][13]

Benzyl alcohol has been reported to cause skin allergy.[14]

Benzyl alcohol is severely toxic and highly irritating to the eye.[11] Pure benzyl alcohol produces corneal necrosis.[15]

Benzyl alcohol is not considered to be a carcinogen and no data are available regarding teratogenic or reproductive effects.[11]

References

  1. ↑ "Benzyl alcohol". Archived from the original on 2009-07-26.
  2. ↑ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X, 1138
  3. ↑ Dietland Muller-Schwarze (2003). The Beaver: Its Life and Impact. p. 43.
  4. ↑ Furuta, Kyoji; Gao, Qing-Zhi; Yamamoto, Hisashi (1995). "Chiral (Acyloxy)borane Complex-Catalyzed Asymmetric Diels-Alder Reaction: (1R)-1,3,4-Trimethyl-3-Cyclohexene-1-Carboxaldehyde". Org. Synth. 72: 86.; Coll. Vol., 9, p. 722
  5. ↑ Parris, Chester L. (1962). "N-benzylacrylamide". Org. Synth. 42: 16.; Coll. Vol., 5, p. 73
  6. ↑ Benzyl alcohol, chemicalland21.com
  7. ↑ Michael Ash; Irene Ash (2004). Handbook of Preservatives. Synapse Info Resources. p. 292. ISBN 978-1-890595-66-1.
  8. ↑ Alex Wissner-Gross (2006). "Dielectrophoretic reconfiguration of nanowire interconnects" (PDF). Nanotechnology. 17: 4986–4990. doi:10.1088/0957-4484/17/19/035.
  9. ↑ Nanowires get reconfigured, Nanotechweb.org, 19 October 2006
  10. ↑ Prescribing Information for Ulesfia Lotion (PDF), Sciele Pharmaceuticals, Inc., April 2009, retrieved 2009-08-29.
  11. 1 2 3 Friedrich Brühne; Elaine Wright (2007), "Benzyl Alcohol", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 7–8
  12. ↑ Carl R. Baum (2008), "Examples of mass exposures involving the pediatric population", in Jerrold B. Leikin; Frank P. Paloucek, Poisoning and Toxicology Handbook (4th ed.), Informa, p. 726
  13. ↑ Juan Gershanik; et al. (1982), "The gasping syndrome and benzyl alcohol poisoning.", N Engl J Med, 307: 1384–8, doi:10.1056/nejm198211253072206
  14. ↑ EJ Curry; EM Warshaw (2005), "Benzyl alcohol allergy: importance of patch testing with personal products.", Dermatitis (16): 203–8
  15. ↑ Swarupa G Kulkarni; Harihara M Mehendale (2005), "Benzyl Alcohol", Encyclopedia of Toxicology, 1 (2nd ed.), Elsevier, pp. 262–264

External links

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