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Benzenemethanol is also known as benzyl alcohol.
Benzenemethanol's chemical formula is C6H5CH2OH and its density is 1.045 g/mL at 25 ° C (lit).
Benzenemethanol is one of the simplest fatty alcohol containing phenyl.
CAS: 100-51-6
MF: C7H8O
MW: 108.14
EINECS: 202-859-9
Synonyms
Benzylalkohol;benzylalcohol,benzylalcohol,benzenemethanol;PHENYLMETHANOL/BENZYLALCOHOL;BENZYL ALCOHOL (TECH);BENZYL ALCOHOL NF FCC KOSHER;BENZYL ALCOHOL PERFUME GRADE 99.5% FCC NF;BENZYLALCOHOL,NF;BENZYLALCOHOL,REAGENT,ACS(BULK
Benzenemethanol can be seen as benzene substituted by hydroxymethyl, or methyl alcohol substituted by phenyl.
Benzenemethanol is a colorless transparent sticky liquid with faint aroma.
Sometimes Benzenemethanol is placed for a long time, it will smells like bitter almond flavor because of oxidation.
Polarity, low toxicity and low steam, so Benzenemethanol is used as alcohol solvent.
Benzenemethanol is combustible, and slightly soluble in water (about 25ml of water soluble 1 gram of benzyl alcohol).
Benzenemethanol is miscible with ethanol, ethyl ether, benzene, chloroform and other organic solvents.
Benzenemethanol mainly exists in the form of free or ester in essential oil, such as jasmine oil, ylang-ylang oil, jasmine oil, hyacinth oil, sesame oil, hyacinths balsam, peru balsam and tolu balsam, which all contain this ingredient.
Benzenemethanol should not be stored for a long time.
Benzenemethanol can be slowly oxidized to benzaldehyde and anisole in the air.
Therefore Benzenemethanol products often smell like almond aroma with characteristic of benzaldehyde.
In addition, Benzenemethanol is also easily oxidized to benzoic acid by many kinds of antioxidants such as nitric acid.
Benzenemethanol is a component catalyst for epoxy resins.
Benzenemethanol is also contained in the color developer C-22.
Benzenemethanol is an aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.
Benzenemethanol has a role as a solvent, a metabolite, an antioxidant and a fragrance.
An aromatic primary alcohol.
Benzenemethanol is synthesized by Cannizzaro’s reaction, which involves the simultaneous oxidation and reduction of benzenecarbaldehyde (benzaldehyde) by refluxing in an aqueous solution of sodium hydroxide:
2C6H5CHO → C6H5CH2OH + C6H5COOH
Benzenemethanol undergoes the reactions characteristic of alcohols, especially those in which the formation of a stable carbonium ion as an intermediate (C6H5CH2 +) enhances the reaction.
Substitution onto the benzene ring is also possible; the –CH2OH group directs into the 2- or 4-position by the donation of electrons to the ring.
Benzenemethanol has been used as an antimicrobial agent in pharmaceutical preparations for many years.
Parenteral administration of preparations containing 0.9% Benzenemethanol resulted in the death of 16 neonates in the USA in the early 1980s.
Many countries subsequently warned against using such preparations in neonates.
This decision is not applicable to the use of benzyl alcohol as a preservative in other circumstances or to its use in topical preparations and no country has placed a total ban on the compound.
Benzenemethanol 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.
Benzenemethanol is a colorless liquid with a mild pleasant aromatic odor.
Benzenemethanol is useful as a solvent for its polarity, low toxicity, and low vapor pressure.
Benzenemethanol 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.
Benzenemethanol in industrial applications is a colorless liquid with a mild pleasant aromatic odor.
Benzenemethanol is a useful solvent due to its polarity, low toxicity, and low volatility.
Benzenemethanol is used as a general solvent for inks, waxes, shellacs, paints, lacquers and epoxy resin coatings.
Like most alcohols, Benzenemethanol reacts with carboxylic acids to form esters.
Benzenemethanol Chemical Properties
Melting point: -15 °C
Boiling point: 205 °C
Density: 1.045 g/mL at 25 °C(lit.)
Vapor density: 3.7 (vs air)
Vapor pressure: 13.3 mm Hg ( 100 °C)
Refractive index: n20/D 1.539(lit.)
FEMA: 2137 | BENZYL ALCOHOL
Fp: 201 °F
Storage temp.: Store at +2°C to +25°C.
Solubility H2O: 33 mg/mL, clear, colorless
Form: Liquid
pka: 14.36±0.10(Predicted)
Color: APHA: ≤20
Relative polarity: 0.608
Odor: Mild, pleasant.
Odor Type: floral
Biological source: synthetic
Explosive limit: 1.3-13%(V)
Water Solubility: 4.29 g/100 mL (20 ºC)
Merck: 14,1124
JECFA Number: 25
BRN: 878307
Henry's Law Constant: <2.70 x 10-7 at 25 °C (thermodynamic method-GC/UV, Altschuh et al., 1999)
Exposure limits: No exposure limit is set. Because of its low vapor pressure and low toxicity, the health hazard to humans from occupational exposure should be very low.
Dielectric constant: 13.1（20℃）
InChIKey: WVDDGKGOMKODPV-UHFFFAOYSA-N
LogP: 1.05 at 20℃
Surface tension: 39.2mN/m at 293.15K
CAS DataBase Reference: 100-51-6(CAS DataBase Reference)
NIST Chemistry Reference: Benzenemethanol(100-51-6)
EPA Substance Registry System: Benzenemethanol (100-51-6)
Benzenemethanol has a characteristic pleasant, fruity odor and a slightly pungent, sweet taste; the note tends to become similar to that of benzyl aldehyde on aging.
Slightly soluble in water, and miscible with alcohol, ether, chloroform and so on.
Benzenemethanol occurs in many essential oils and foods.
Benzenemethanol is a colorless liquid with a weak, slightly sweet odor.
Benzenemethanol can be oxidized to benzaldehyde, for example, with nitric acid.
Dehydrogenation over a copper–magnesium oxide–pumice catalyst also leads to the aldehyde.
Esterification of Benzenemethanol results in a number of important fragrance and flavor materials.
Diphenylmethane is prepared by a Friedel–Crafts reaction of benzyl alcohol and benzene with aluminum chloride or concentrated sulfuric acid.
By heating Benzenemethanol in the presence of strong acids or strong bases, dibenzyl ether is formed.
Uses
Benzenemethanol is a colorless clear oily liquid; its odor type is floral and its odor at 100% is described as 'floral rose phenolic balsamic'.
Benzenemethanol is used in cosmetics as afragrance component, preservative, solvent and diluting agent for perfumes and flavors, and viscosity-decreasing agent.
Benzenemethanol is used as a solvent for surface-coating materials, cellulose esters and ethers, alkyd resins,acrylic resins, fats, dyestuffs,casein (when hot), gelatin, shellac and waxes.
Benzenemethanol is added in small amounts to surface-coating materials to improve their flow and gloss.
In the textile industry, Benzenemethanol is used as anauxiliary in the dyeing of wool, polyamides, and polyesters.
In pharmacy Benzenemethanol is used as a local anesthetic ingredient in over-the-counter anorectal, oral healthcare and topical analgesic drug products and, because of its antimicrobial effect, as an ingredient of ointments and other preparations (U.S. National Library of Medicine).
Benzenemethanol is also a starting material for the preparation of numerous benzyl esters that are used as odorants, flavors, stabilizers for volatile perfumes, and plasticizers and is also employed in the extractive distillation of m- and p-xylenes and m- and p-cresols.
Other uses include or have included heat-sealing of polyethylene films,in color photography as a development accelerator and in microscopy as embedding material (U.S.National Library of Medicine).
Esters of Benzenemethanoll are used in makingperfume, soap, flavoring, lotion, and ointment.
Benzenemethanol finds application in color photography;the pharmaceuticals industry, cosmetics,and leather dyeing; and as an insect repellent.
Benzenemethanol occurs in natural products such as oils ofjasmine and castoreum.
Benzyl alcohol is widely used as a solvent for the dielectrophoretic reconfiguration of nanowires, inks, paints, lacquers and epoxy resin coatings and as a precursor to a variety of esters used in soaps, perfumes and flavoring.
Benzenemethanol is employed as a local anesthetic which reduces the pain associated with lidocaine injection.
Benzenemethanol has a various applications in baby products, bath products, soaps and detergents, eye makeup, blushers, cleansing products, make up products as well as hair, nail and skin care products.
Benzenemethanol is a preservative against bacteria, used in concentrations of 1 to 3 percent. Benzenemethanol can cause skin irritation.
Benzenemethanol is used as a general solvent for inks, waxes, shellacs, paints, lacquers, and epoxy resin coatings.
Thus Benzenemethanol can be used in paint strippers, especially when combined with compatible viscosity enhancers to encourage the mixture to cling to painted surfaces.
Benzenemethanol 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.
Benzenemethanol can be used as a local anesthetic, especially with epinephrine.
As a dye solvent, Benzenemethanol enhances the process of dying wool, nylon, and leather.
Use in health care
Benzenemethanol is used as a bacteriostatic preservative at low concentration in intravenous medications, cosmetics, and topical drugs.
Benzenemethanol, 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.
Benzenemethanol 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.
Benzenemethanol is used effectively for treating lice infestations as the active ingredient in lotion shampoo with 5% benzyl alcohol.
Benzenemethanol 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.
Benzenemethanol is a common ingredient in a variety of household products.
Pharmaceutical Applications
Benzenemethanoll is an antimicrobial preservative used in cosmetics, foods, and a wide range of pharmaceutical formulations, including oral and parenteral preparations, at concentrations up to 2.0% v/v.
The typical concentration used is 1% v/v, and Benzenemethanol has been reported to be used in protein, peptide and small molecule products, although its frequency of use has fallen from 48 products in 1996, 30 products in 2001, to 15 products in 2006.
In cosmetics, concentrations up to 3.0% v/v may be used as a preservative.
Concentrations of 5% v/v or more are employed as a solubilizer, while a 10% v/v solution is used as a disinfectant.
Benzenemethanol 10% v/v solutions also have some local anesthetic properties, which are exploited in some parenterals, cough products, ophthalmic solutions, ointments, and dermatological aerosol sprays.
Although widely used as an antimicrobial preservative, Benzenemethanol has been associated with some fatal adverse reactions when administered to neonates.
Benzenemethanol is now recommended that parenteral products preserved with benzyl alcohol, or other antimicrobial preservatives, should not be used in newborn infants if at all possible.
Production Method
1.Benzenemethanol with potassium or sodium is heated for a long timg, and hydrolyzes to yield benzyl alcohol.
2.Benzaldehyde in methanol and sodium hydroxide solution react to Benzenemethanol at 65~75 ℃.
The product has high purity.
3.Using benzyl chloride as raw materials, Benzenemethanol is heated and hydrolyzes to yield benzyl alcohol in the presence of the sodium catalyst.
Specification of spices benzyl alcohol(QB792-81): the relative density of 1.041-1.046; refractive index of 1.538-1.541; boiling range 203-206℃ and distillate volume more than 95%; dissolving completely in 30 volumes of distilled water; containing more than 98 percent of alcohol; chlorine test (NF) as the side reaction.
Raw material consumption quota: benzyl chloride 1600kg/t; soda ash 1000kg/t.
4.Benzyl alcohol exists naturally in orange flower, ylang-ylang, jasmine, gardenia, acacia, lilac and hyacinth.
Benzyl chloride or benzaldehyde is used as raw materials to prepare Benzenemethanol in the industry.
5.Add chlorobenzyl to 12% sodium carbonate solution, heat to 93 ℃ and stir for 5h.
Then warm the mixture to 101~103℃ and react for 10h.
After the reaction, cool Benzenemethanol to the room temperature, and add salt to saturation.
After still standing for stratification, take the upper liquid and get crude products through pressure distillation. Then refine to gain the target products.
The yield is 70%～72%.
C6H5CH2Cl+H2O[Na2CO3]→C6H5CH2OH+NaCl+CO2↑
In the presence of sodium hydroxide, formaldehyde and benzaldehyde react to produce benzyl alcohol by disproportionation reaction.
C6H5CHO+HCHO[NaOH]→C6h5CH2OH+HCOONa
Preparation
Benzenemethanol is prepared commercially by the distillation of benzyl chloride with potassium or sodium carbonate.
Benzenemethanol may also be prepared by the Cannizzaro reaction of benzaldehyde and potassium hydroxide.
Preparation
Benzenemethanol 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.
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 Benzenemethanol, an example of an organic disproportionation reaction.
