ChemicalBook > Product Catalog > Organic Chemistry > Alcohols,Phenols,Phenol alcohols > cyclitols > Phenethyl alcohol
Phenethyl alcohol Chemical Properties
- Melting point:−27 °C(lit.)
- Boiling point:219-221 °C750 mm Hg(lit.)
- Density 1.020 g/mL at 20 °C(lit.)
- vapor density 4.21 (vs air)
- vapor pressure 1 mm Hg ( 58 °C)
- refractive index n
- FEMA 2858 | PHENETHYL ALCOHOL
- Flash point:216 °F
- storage temp. Store at RT.
- solubility Miscible with chloroform.
- form Liquid
- color Clear colorless
- Odorfloral odor of roses
- PH6-7 (20g/l, H2O, 20℃)
- explosive limit1.4-11.9%(V)
- Water Solubility 20 g/L (20 ºC)
- JECFA Number987
- Merck 14,7224
- BRN 1905732
- Stability:Stable. Substances to be avoided include strong acids and strong oxidizing agents. Combustible.
- CAS DataBase Reference60-12-8(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzeneethanol(60-12-8)
- EPA Substance Registry SystemBenzeneethanol (60-12-8)
- Hazard Codes Xn
- Risk Statements 21/22-36/38-36-22
- Safety Statements 26-28-36/37-36/37/39
- RIDADR 2810
- WGK Germany 1
- RTECS SG7175000
- Autoignition Temperature410 °C
- TSCA Yes
- HazardClass 6.1
- PackingGroup III
- HS Code 29062990
- Hazardous Substances Data60-12-8(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 1790 mg/kg (Jenner)
Phenethyl alcohol Usage And Synthesis
- Edible spicesPhenethyl alcohol is a kind of edible spices, and naturally exists in neroli, rose oil, geranium oil and other oils, because it has a soft, pleasant and persistent rose fragrance and is widely used in various kinds of flavors and cigarette flavor. It is dispensing rose scent, food additives, the main raw material for rose scent flavor, stable on alkali, which are widely used in soap fragrance, is essence blending all rose scent series of spices, because it does not dissolve in water, it is often used in the making up water, soap and orange flower, purple, etc. It is also used in the blending of flavor. Because the Phenethyl alcohol has a good antibacterial efficiency, it can be used in the ophthalmic solution. At present there are main three synthesis methods as following:
1, by styrene via halogenation, saponification, hydrogenation, distillation.
2, and microorganism fermentation in yeast by bioconversion.
3, calcium carbide, benzene as raw material preparation of benzyl ethanol, reaction equations are as follows:
- Chemical PropertiesPhenethyl alcohol is a clear, colorless liquid with an odor of rose oil. It has a burning taste that irritates and then anesthetizes mucous membranes.
Phenethyl Alcohol (PEA) is an aromatic alcohol that is used as a fragrance and an antimicrobial preservative in cosmetic formulations. It is active at pH 6 or less and is inactivated by nonionic detergents including polysorbate-80. PEA is also a widely used fragrance material that imparts a rose character to perfume compositions. Almost all rose fragrances and other floral-type perfumes contain PEA, and PEA is used extensively for many other fragrance applications because it blends ell.
PEA is metabolized to phenylacetic acid in mammals. In humans, it is excreted in urine as the conjugate phenylacetylglutamine.
- UsesPhenylethyl alcohol is qualitatively and quantitatively one of the most important fragrance substances that belongs to the class of araliphatic alcohols.
Phenylethyl alcohol is used frequently and in large amounts as a fragrance material. It is a popular component in rose-type compositions, but it is also used in other blossom notes. It is stable to alkali and, therefore, ideally suited for use in soap perfumes.
- ProductionMany syntheticmethods are known for preparing phenylethyl alcohol; the following are currently of industrial importance:
1) Friedel–Crafts reaction of benzene and ethylene oxide: In the presence of molar quantities of aluminum chloride, ethylene oxide reacts with benzene to give an addition product, which is hydrolyzed to phenylethyl alcohol:
Formation of by-products, such as 1,2-diphenylethane, is largely avoided by using an excess of benzene at low temperature. Special purification procedures are required to obtain a pure product that is free of chlorine and suitable for use in perfumery.
2) Hydrogenation of styrene oxide: Excellent yields of phenylethyl alcohol are obtainedwhen styrene oxide is hydrogenated at low temperature, using Raney nickel as a catalyst and a small amount of sodium hydroxide.
- Chemical PropertiesPhenethyl alcohol is the main component of rose oils obtained from rose blossoms. It occurs in smaller quantities in neroli oil, ylang-ylang oil, carnation oil, and geranium oils. Since the alcohol is rather soluble in water, losses occur when essential oils are produced by steam distillation.
Phenylethyl alcohol is a colorless liquid with a mild rose odor. It can be dehydrogenated catalytically to phenylacetaldehyde and oxidized to phenylacetic acid (e.g.,with chromic acid). Its fatty acid esterswith lowermolecularmass, as well as some alkyl ethers, are valuable fragrance and flavor substances.
- Chemical PropertiesPhenethyl alcohol has a characteristic rose-like odor and an initially slightly bitter taste, then sweet and reminiscent of peach.
- OccurrenceReported found (as is or esterified) in several natural products: rose concentrate, rose absolute (60% or more) and rose distillation waters; also found in the essential oils of neroli, ylang-ylang, narcissus, hyacinth, lily, tea leaves, Michelia champaca, Pandamus odoratissimus, Congo and Réunion geranium, tobacco and other oils. It has been identified in wines. It has also been reported found in over 200 foods and beverages including apple, apricot, orange juice, orange peel, many berries, bilberry, cherry, grapefruit, peach, raisin, blackberry, guava, grapes, melon, papaya, asparagus, cabbage, leek, potato, rutabaga, tomato, Mentha oils, cinnamon, ginger, breads, butter, saffron, mustard, mango, many cheeses, butter, milk, cooked chicken, cognac, hop oil, beer, rum, whiskies, cider, sherry, cocoa, coffee, tea, nuts, oats, honey, soybean, coconut meat, avocado, olive, passion fruit, plum, beans, mushroom, starfruit, mango, tamarind, fruit brandies, fig, gin, rice, quince, radish, litchi, sukiyaki, calamus, licorice, buckwheat, watercress, elderberry fruit, kiwifruit, loquat, Tahiti and Bourbon vanilla, mountain papaya, endive, lemon balm, clary sage, shrimps, crab, Chinese quince, lamb’s lettuce, truffle and maté.
- UsesPharmaceutic aid (antimicrobial). In flavors and perfumery (esp rose perfumes).
- Usesphenethyl alcohol is used to mask odor and also as a preservative.
- UsesIn fragrance; antimicrobial agent; in organic synthesis; preservative, food additive
- Production MethodsPhenylethyl alcohol is prepared by reduction of ethyl phenylacetate with sodium in absolute alcohol; by hydrogenation of phenylacetaldehyde in the presence of a nickel catalyst; or by addition of ethylene oxide or ethylene chlorohydrin to phenylmagnesium bromide, followed by hydrolysis. Phenylethyl alcohol also occurs naturally in a number of essential oils, especially rose oil.
- PreparationFrom toluene, benzene or styrene.
- Aroma threshold valuesDetection: 0.015 ppb to 3.5 ppm; recognition: 1.2 ppm. Aroma characteristics at 1.0%: floral honey, yeasty bready, musty fresh and sweet.
- Taste threshold valuesTaste characteristics at 20 ppm: mushroom-like, rose floral, sweet, rosy, bready with honey nuances.
- Synthesis Reference(s)Chemistry Letters, 18, p. 619, 1989
Journal of the American Chemical Society, 100, p. 4888, 1978 DOI: 10.1021/ja00483a042
Tetrahedron Letters, 18, p. 3263, 1977 DOI: 10.1016/S0040-4039(01)83213-5
- Health HazardPhenylethanol is an irritant of the eyes and a teratogen in rats.
- Pharmaceutical ApplicationsPhenylethyl alcohol is used as an antimicrobial preservative in nasal, ophthalmic, and otic formulations at 0.25–0.5% v/v concentration; it is generally used in combination with other preservatives.Phenylethyl alcohol has also been used on its own as an antimicrobial preservative at concentrations up to 1% v/v in topical preparations. At this concentration, mycoplasmas are inactivated within 20 minutes, although enveloped viruses are resistant.Phenylethyl alcohol is also used in flavors and as a perfumery component, especially in rose perfumes.
- Safety ProfileModerately toxic by ingestion and skin contact. A skin and eye irritant. Experimental teratogenic effects. Other experimental reproductive effects. Causes severe central nervous system injury to experimental animals. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidzing materials. To fight fEe, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes
- SafetyPhenylethyl alcohol is generally regarded as a nontoxic and
nonirritant material. However, at the concentration used to preserve
eye-drops (about 0.5% v/v) or above, eye irritation may occur.
LD50 (rabbit, skin): 0.79 g/kg
LD50 (rat, oral): 1.79 g/kg
- CarcinogenicityPhenylethanol was not mutagenic in bacterial assays, nor did it increase the number of sister chromatid exchanges in human lymphocytes.
- MetabolismPhenylethyl alcohol is oxidized almost entirely to the corresponding acid (Williams. 1959).
- storagePhenylethyl alcohol is stable in bulk, but is volatile and sensitive to
light and oxidizing agents. It is reasonably stable in both acidic and
alkaline solutions. Aqueous solutions may be sterilized by
autoclaving. If stored in low-density polyethylene containers,
phenylethyl alcohol may be absorbed by the containers. Losses to
polypropylene containers have been reported to be insignificant
over 12 weeks at 30°C. Sorption to rubber closures is generally
The bulk material should be stored in a well-closed container, protected from light, in a cool, dry place.
- Purification MethodsPurify the ethanol by shaking it with a solution of ferrous sulfate, and the alcohol layer is washed with distilled water and fractionally distilled. [Beilstein 6 IV 3067.]
- IncompatibilitiesIncompatible with oxidizing agents and protein, e.g. serum. Phenylethyl alcohol is partially inactivated by polysorbates, although this is not as great as the reduction in antimicrobial activity that occurs with parabens and polysorbates.
- Regulatory StatusIncluded in the FDA Inactive Ingredients Database (nasal, ophthalmic, and otic preparations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
Phenethyl alcohol Preparation Products And Raw materials
- Preparation ProductsPropylene oxideAcetophenoneMalathionPhenylacetaldehyde2,5-DichloroanilineDiethyl maleateRose Oil4-(2-Methoxyethyl)Phenol(2-Bromoethyl)benzeneBenzyl salicylate[[p-(2-methoxyethyl)phenoxy]methyl]oxirane Phenethyl cinnamatePhenethyl butyrate(2-Methoxyethyl)benzenePhenethyl isobutyrateFEMA 3222Phenethyl acetatep-(2-Methoxyethyl) phenolPHENETHYL SALICYLATEFEMA 3632Phenethyl phenylacetateMetoprololFEMA 2859Styralyl acetateCONVALLATOXINPHENETHYL FORMATE2-PHENYLETHYL PROPIONATEFEMA 2871
- Raw materialsSodium hydroxideSulfuric acid SodiumNitrogenSULFURIC ACIDHydrogenETHYLENE OXIDENickelBenzyl chlorideBromobenzeneBenzeneacetonitrileStyrene2-ChloroethanolAluminium chloride hexahydrateSodium chlorateSodium bromideMotor benzolPhenylacetic acid ethyl esterStyrene oxideFEMA 2771Geranium oilRose OilAir blower
- 9-Fluorenylmethyl chloroformate 1-Phenyl-1-cyclopropanecarboxylic acid 1-Phenylcyclopentanecarboxylic acid 9-HYDROXYFLUORENE-9-CARBOXYLIC ACID CYCLOHEXYLPHENYLACETIC ACID 1-phenylcyclopropanemethanol 2-Hydroxy-1,4-naphoquinone 9-Fluorenemethanol 1-(4-CHLOROPHENYL)-1-CYCLOPROPANECARBOXYLIC ACID 1-(4-CHLOROPHENYL)-1-CYCLOPENTANECARBOXYLIC ACID 9-Carboxyfluorene 1-(4-CHLOROPHENYL)-1-CYCLOBUTANECARBOXYLIC ACID 1-(4-METHOXYPHENYL)-1-CYCLOPENTANECARBOXYLIC ACID Benzilic acid Phenethyl alcohol 4-Nitrobenzeneethanol Phenethyl phenylacetate 2-(4-Aminophenyl)ethanol
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