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Benzyl alcohol structure

Benzyl alcohol
  • CAS：100-51-6
  • MW:108.13800
  • MF：C7H8O
Benzyl alcohol, with the chemical formula C7H8O and CAS registry number 100-51-6, is an aromatic alcohol commonly used as a solvent, preservative, and fragrance ingredient. This clear liquid has a mild, pleasant odor and is known for its ability to dissolve a wide range of substances. Benzyl alcohol is utilized in various industries, including pharmaceuticals, cosmetics, and personal care products. It serves as a precursor in the synthesis of numerous chemicals and pharmaceutical compounds. Benzyl alcohol also finds application as a flavoring agent and in the manufacturing of perfumes and flavorings. Additionally, it has antimicrobial properties, making it useful in medicinal and topical formulations. Despite its widespread use, benzyl alcohol should be handled with care due to its potential toxicity in high concentrations.
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1. Names and Identifiers
1.1 Name
Benzyl alcohol
1.2 Synonyms
BENZYL ALCOHOL (TECH); BENZYL ALCOHOL NF FCC KOSHER; benzylalcohol,benzylalcohol,benzenemethanol; BENZYLALCOHOL,NF; BENZYLALCOHOL,REAGENT,ACS(BULK; Benzylalkohol; EINECS 202-859-9; MFCD00004599; PHENYLMETHANOL/BENZYLALCOHOL;
1.3 CAS No.
100-51-6
1.4 CID
244
1.5 EINECS
202-859-9
1.6 Molecular Formula
C7H8O
1.7 Inchi
InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
1.8 InChkey
WVDDGKGOMKODPV-UHFFFAOYSA-N
1.9 Canonical Smiles
C1=CC=C(C=C1)CO
1.10 Isomers Smiles
C1=CC=C(C=C1)CO
2. Properties
2.1 Vapour pressure
3.7 (vs air)
2.2 Solubility
H2O: 33?mg/mL, clear, colorless
2.3 Viscosity
Viscosity is a measure of a fluid's resistance to flow. It describes the internal friction of a moving fluid.
2.4 VaporDensity
3.7 (vs air)
2.5 AnalyticLaboratory Methods
Method: EPA-EAD 1625; Procedure: gas chromatography/mass spectrometry; Analyte: benzyl alcohol;; Matrix: water;; Detection Limit: not provided.
2.6 Appearance
Colourless liquid
2.7 AutoIgnition
817° F (USCG, 1999)
2.8 Storage
Benzyl alcohol oxidizes slowly in air to benzaldehyde and benzoicacid; it does not react with water. Aqueous solutions may besterilized by filtration or autoclaving; some solutions may generatebenzaldehyde during autoclaving.Benzyl alcohol may be stored in metal or glass containers. Plasticcontainers should not be used; exceptions to this includepolypropylene containers or vessels coated with inert fluorinatedpolymers such as Teflon.Benzyl alcohol should be stored in an airtight container,protected from light, in a cool, dry place.
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2.9 Carcinogenicity
In an NTP study, F344 rats weredosed by oral gavage with 0, 200, and 400 mg/kg, 5 days/week for 2 years. Benzyl alcohol had no effect on the survivalof male rats; female rats had reduced survival, and many ofthe early deaths were considered related to the gavageprocedure. There were no treatment-related effects on nonneoplasticor neoplastic lesions in either sex treated withbenzyl alcohol. It was concluded that under the conditions ofthe study, there was no evidence of carcinogenic activity. In the same NTP study, B6C3F1 mice were dosed byoral gavage with 0, 100, and 200 mg/kg, 5 days/week for2 years. No effects on survival or body weight gain wereobserved. There were no treatment-related effects on nonneoplasticor neoplastic lesions in either sex. It was concludedthat under the conditions of the study, there was noevidence of carcinogenic activity.
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2.10 Physical Properties
Colorless, hygroscopic, air sensitive liquid with a faint, pleasant, aromatic odor. Odor thresholdconcentration in water is 10 ppm (Buttery et al., 1988).
2.11 Color/Form
Water-white liquid
2.12 Contact Allergens
Benzyl alcohol is mainly a preservative, mostly used intopical antimycotic or corticosteroid ointments. It isalso a component catalyst for epoxy resins and is containedin the color developer C-22. As a fragranceallergen, it has to be mentioned by name in cosmeticswithin the EU.
2.13 Corrosivity
Will attack some plastics
2.14 Decomposition
When heated to decomposition it emits acrid smoke and fumes.
2.15 Heat of Combustion
894.3 kg cal/g mol wt at 20 deg C
2.16 Heat of Vaporization
50.48 kJ/mol at 205.31 deg C
2.17 Odor
Faint aromatic odor
2.18 Odor Threshold
5.5 ppm
2.19 PH
A solution in water is neutral to litmus
2.20 Physical
BENZYL ALCOHOL; is a clear colorless liquid with a pleasant odor. Slightly denser than water;. Flash point 194°F. Boiling point 401°F. Contact may irritate skin, eyes, and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals.
2.21 pKa
14.36±0.10(Predicted)
2.22 Water Solubility
H2O: 4.29 g/100 mL (20 oC);Solubility in water, g/100ml: 4
2.23 Spectral Properties
SADTLER REF NUMBER: 157 (IR, PRISM); 985 (IR, GRATING); MAX ABSORPTION (ALCOHOL): 243 NM (LOG E= 1.91); 258.5 NM (LOG E= 2.26); 268 NM (LOG E= 1.95)
Index of refraction: 1.5396 at 20 deg C/D
IR: 5219 (Coblentz Society Spectral Collection)
UV: 62 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 161 (Varian Associates NMR Spectra Catalogue)
MASS: 61913 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 204 (National Bureau of Standards)
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2.24 Stability
Hygroscopic. Stable under recommended storage conditions. Test for peroxide formation before distillation or evaporation. Test for peroxide formation or discard after 1 year.
2.25 StorageTemp
Store at +2°C to +25°C.
2.26 Surface Tension
39.0 dynes/cm at 20 deg C; 33 dyn/cm at 80 deg C
2.27 Toxicity Summary
IDENTIFICATION: Benzyl alcohol; is an aromatic organic alcohol, water;-white in color with a faint aromatic odor and a sharp burning taste; it is a preservative, a solvent, and a local anesthetic. It is used in a wide variety of products including photographic developer for color movie films; dyeing nylon; filament, textiles, and sheet plastics; solvent for dyestuffs, cellulose esters, casein, waxes; heat-sealing polyethylene; films; intermediate for benzyl esters and ethers; bacteriostatic; cosmetics, ointments, emulsions; ball point pen inks; stencil inks. HUMAN EXPOSURE AND TOXICITY: Benzyl alcohol; has been found to be irritating to the skin at levels 3% or greater. Patch test with 0.65% benzyl alcohol; did not produce irritation of the skin. Benzyl alcohol; poisoning can cause the gasping syndrome in neonates. The infants had a typical course of gradual neurologic deterioration, severe metabolic acidosis, the striking onset of gasping respirations, thrombocytopenia, hepatic and renal failure, hypotension, cardiovascular collapse and death. In every infant, unmetabolized benzyl alcohol; was identified in the urine. Hypersensitivity reactions may occur after parenteral or dermal exposure to benzyl alcohol;. Acute reactions include urticaria, erythema, palpable edema, fatigue, nausea, diffuse angioedema, maculopapular rash, and fever. A delayed hypersensitivity reaction characterized by erythema, edema, and vesiculation may appear in 2 to 3 days after an immediate reaction to a single benzyl alcohol; challenge in the same patient. Reports are available contraindicating the use of neuromuscular blocking agents containing benzyl alcohol;. Use of these agents was not advised in neonates or in the epidural space. Benzyl alcohol; 0.225 mg/mL, the clinically relevant concentration in triamcinolone acetonide; (TA) following intravitreal injection, caused ultrastructural damage and impaired human retinal; pigment epithelial cell function at 2 hr. Benzyl alcohol; 9.0 mg/mL, the concentration in commercial TA suspensions, was toxic within 5 minutes. ANIMAL STUDIES: In a primary irritation study 10% benzyl alcohol; applied in a 24-hour occlusive patch to the back of eight male albino rabbits did not cause irritation. Undiluted benzyl alcohol; was moderately irritating when applied to the depilated skin of guinea pigs for 24 hr. Acute intravenous toxicity of benzyl alcohol; was determined in mice. Clinical signs were convulsion, dyspnea and reduced motility in all strains for 24 hours. The slight decrease in body weight in the first week following treatment returned to normal in the second week. Microscopic examination revealed local nerve degeneration when 5% benzyl alcohol; was injected into the side of a cat's face; at 10% local anesthesia was produced. In another experiment, rats were given oral doses of 50, 100, 200, 400, and 800 mg/kg for 13 weeks. The high dose produced clinical signs indicative of neurotoxicity including staggering, respiratory difficulty, and lethargy. Reduction in weight gain was noted in males at 800 mg/kg and females at equal to or greater than 200 mg/kg. The high dose animals also showed hemorrhages around the mouth and nose, and histological lesions in the brain, thymus, skeletal muscle, and kidney. Fifty pregnant mice were given 750 mg/kg/day benzyl alcohol; in water; by gavage on days 6-13 of gestation and were allowed to deliver. A decrease in the birth weight and weight gain in the pups was observed, but the chemical was not toxic to the mothers and had no effect on pup viability. Benzyl alcohol; was tested for genotoxicity in 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of metabolic activation. The highest ineffective dose tested without toxicity in any S. typhimurium strains was 5.0 mg/plate. Slight inhibition of the background bacterial lawn occurred in cultures at 6.666 mg/plate but no significant change was seen in the results. In a mammalian cell genotoxicity assay using CHO cells, benzyl alcohol; was negative without metabolic activation and positive with metabolic activation.
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3. Use and Manufacturing
3.1 Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: Will attack some plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
3.2 Definition
ChEBI: An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.
3.3 Description
Benzyl alcohol (CAS 100-51-6) is a clear, colorless liquid with a mild, pleasant odor. It has a basic structure consisting of a benzene ring with a hydroxyl group (-OH) attached. This chemical is highly soluble in water, meaning it can easily dissolve in it. It also exhibits moderate solubility in organic solvents such as ethanol and ether. Benzyl alcohol has a boiling point of 205°C and a melting point of -15°C.

Benzyl alcohol possesses various physical and chemical properties. It is flammable and can form explosive mixtures with air. It is also a volatile compound, meaning it can evaporate easily. Benzyl alcohol is stable under normal conditions but may react with strong oxidizing agents. It can undergo oxidation to form benzaldehyde or benzoic acid. Additionally, it can react with acids to form esters.

Applicable fields
Benzyl alcohol finds application in several industries due to its properties. It is commonly used in the pharmaceutical industry as a solvent and preservative. It can help dissolve and stabilize various active ingredients in medications. In the personal care industry, benzyl alcohol is used as a fragrance ingredient and a solvent in cosmetic formulations. It can also act as a preservative, preventing the growth of microorganisms in products.

Mechanism of action
In pharmaceutical applications, benzyl alcohol acts as a solvent, allowing the dissolution of hydrophobic drugs. It can also function as a preservative by inhibiting the growth of bacteria and fungi. In the personal care industry, benzyl alcohol provides a pleasant scent to products and helps dissolve other fragrance ingredients. Its preservative properties help extend the shelf life of cosmetic formulations.

Storage Conditions
Store in a cool, dry place.
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3.4 Environmental Fate
Biological. Heukelekian and Rand (1955) reported a 5-d BOD value of 1.55 g/g which is 61.5%of the ThOD value of 2.52 g/g.Chemical/Physical. Slowly oxidizes in air to benzaldehyde (Huntress and Mulliken, 1941).Benzyl alcohol will not hydrolyze because it has no hydrolyzable functional group (Kollig, 1993).
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3.5 GHS Classification
Signal: Warning
GHS Hazard Statements
H302: Harmful if swallowed [Warning Acute toxicity, oral]
H332: Harmful if inhaled [Warning Acute toxicity, inhalation]

Precautionary Statement Codes
P261, P264, P270, P271, P301+P312, P304+P312, P304+P340, P312, P330, and P501
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3.6 Methods of Manufacturing
1. Benzyl alcohol is naturally occurring in orange blossom, ylang ylang, jasmine, gardenia, acacia, lilac, hyacinth, industrial benzyl chloride or benzaldehyde as raw materials. In 12% of the soda solution by adding benzyl chloride, heated to 93 ° C stirring reaction 5h, and then heated to 101 ~ 103 ° C to continue the reaction 10h. After the reaction, cooling to room temperature, adding salt to saturation, standing stratification, take the upper layer of crude oil distillation pressure, and refined products. The yield was 70% ~ 72%. In the presence of sodium hydroxide formaldehyde and benzaldehyde, the disproportionation reaction of benzyl alcohol. 2 to benzyl chloride as raw material, in the base of the catalytic hydrolysis derived hydrolysis. 3. Mix benzyl chloride, sodium carbonate and water in a certain proportion, stir quickly, emulsify the oil layer, raise the temperature to 90 ° C while stirring. When the generated carbon dioxide gas no longer escapes, continue heating to 101 ~ 103 ° C to complete the hydrolysis reaction: cooling after the end of the reaction, standing layered. Take the oil layer washed several times, into the water layer, and then atmospheric distillation, the first steamed water, benzyl chloride and other low boiling, as the initial fraction, and then collected 203 ~ 206 ℃ as the main distillate, is finished. BU, OR, 18; FC, BU, OR, 40; 5. Method: In a reaction flask equipped with a stirrer, a reflux condenser and a thermometer, 250 mL of water, 56 g of sodium carbonate, (2) (63.3 g, 0.5 mol) was added thereto, followed by vigorous stirring to emulsify benzyl chloride. Was added to the micro boil (about 95 & lt; 0 & gt; C). Carbon dioxide is produced in the reaction. Stop the escape of carbon dioxide bubbles that the reaction is completed, and then stirring reaction 0.5h. Cooling, separation of the organic layer, washed with water, crude benzyl alcohol. Fractionation, collecting 204 ~ 205 ° C distillate, in benzyl alcohol ① (1) in a yield of 74%.
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3.7 Produe Method
Benzyl alcohol is prepared commercially by the distillation of benzylchloride with potassium or sodium carbonate. It may also beprepared by the Cannizzaro reaction of benzaldehyde andpotassium hydroxide.
3.8 Purification Methods
It is usually purified by careful fractional distillation under reduced pressure in the absence of air. Benzaldehyde, if present, can be detected by UV absorption at 283nm. It has also been purified by shaking with aqueous KOH and extracting with peroxide-free diethyl ether. After washing with water, the extract is treated with saturated NaHS solution, filtered, washed, dried with CaO and distilled under reduced pressure [Mathews J Am Chem Soc 48 562 1926]. Peroxy compounds can be removed by shaking with a solution of Fe2+ followed by washing the alcohol layer with distilled water and fractionally distilling it. [Beilstein 6 IV 2222.]
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3.9 Usage
1.Benzyl alcohol can be used as raw materials and fixatives of spice, pharmaceutical raw materials and anesthetics, preservatives, coloring additives, coatings and solvent of inks. It also can be used to make ballpoint oil. 2.It can be used as chromatographic analysis reagent. And it also can be used in organic synthesis.3.It can be used for the preparation of sesame oil, drugs and the like. It also can be used as the solvent and fixatives of spice.4.Benzyl alcoholexists in many fragrant essential oils. Then it can be used as condensing agent with benzyl acetate in jasmine, gardenia, lilac, ylang-ylang, tuberose, hyacinth, acacia and other floral type. It has the fixative effect too. It is often used as the solvent to dissolve artificial musk and other spices. In addition, it can be used as food spices inedible flavor, like cherries, grapes, honey, orange, raspberry, walnut, vanilla.5.Benzyl alcohol is the edible spice that is temporarily allowed to use. It is mainly used in almonds, oranges, cherries, grapes, strawberries and other fruit-based flavor. The dosage of benzyl alcohol is as the normal production needs. It is usually 1200mg/kg in the chewing gum, 220mg/kg in baked foods, 160mg/kg in cold drinks, 47mg/kg in the candy, and 15mg/kg in soft drinks.6.Benzyl alcohol is a very useful fixative. It is the indispensable spices to allocate jasmine, polianthes tuberosa, ylang-ylang and other flavorings. It can be used to prepare soaps and daily cosmetics flavorings. But benzyl alcohol can be naturally and slowly oxidized. Part of benzyl alcohol will be oxidized to benzaldehyde and benzyl ether, which makes commercial products with almond scent. It should not be stored for a long time. Benzyl alcohol is widely used in the production of industrial chemicals. It can be used as coating solvent, photographic developer, PVC stabilizer, medicine, solvent of synthetic resin, solvent of vitamin B injection, preservative of unguent or liquid. It also can be used as desiccant of nylon, fiber and plastic film, solvent of dye, cellulose ester and casein, intermediate to prepare benzyl esters or ethers. Meanwhile, it is widely used as pen oil, paint solvent, etc.7.GB 2760--1996 stipulates that benzyl alcohol can be used as food spices temporarily. It also can be used as fixative agent and grease solvent. As spices, it is mainly used for the preparation of berries, nuts and other flavors.8.It can be used in organic synthesis. It can be used as solvent of gelatin, casein (heat), cellulose acetate and shellac and the like, microscope embedding material. It also can be used to determinate the contents of vitamin B12.
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4. Safety and Handling
4.1 Exposure Standards and Regulations
Local anesthetic active ingredients. The active ingredient of the product consists of any of the following when used in the concentration or within the concentration range established for each ingredient: Benzyl alcohol 1 to 4 percent is included on this list.
4.2 Octanol/Water Partition Coefficient
log Kow = 1.10
4.3 Fire Hazard
Benzyl alcohol is combustible.
4.4 Other Preventative Measures
Ventilation control: The basic ventilation methods are local exhaust ventilation & dilution or general ventilation.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
Substitution of less irritating substances.Redesign of operations. Prevent contact, provision of a physical barrier against contact, proper washing facilities, work clothing & storage facilities, protective clothing, & barrier creams. medical control.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. /Benzyl alcohol (Combustible liquid, NOS)/
Personnel protection: Keep upwind. Avoid breathing vapors. Do not handle broken packages unless wearing appropriate personal protective equipment. Avoid bodily contact with the material. /Benzyl alcohol (Combustible liquid, NOS)/
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4.5 Cleanup Methods
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner. /Benzyl alcohol (Combustible liquid, NOS)/
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Benzyl alcohol (Combustible liquid, NOS)/
Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Benzyl alcohol (Combustible liquid, NOS)/
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4.6 DisposalMethods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

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4.7 Fire Fighting Procedures
Foam, carbon dioxide, dry chem.
Alcohol foam. Water or foam may cause frothing.
If material on fire or involved in fire: Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources. /Benzyl alcohol (Combustible liquid, NOS)/
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4.8 FirePotential
Slight, when exposed to heat or flame.
The LIQ is flammable & a moderate fire hazard.
4.9 Safety Profile
Poison by ingestion,intraperitoneal, intravenous, and parenteral routes.Moderately toxic by inhalation, skin contact, andsubcutaneous routes. A moderate skin and severe eyeirritant. Mutation data reported. Combustible liquid.Mixtures with sulfuric ac
4.10 Formulations/Preparations
Grades: free from chlorine (FFC); technical; NF (National Formulary); textile; photographic reagent; FCC
Euxyl K 100
Pure, photo, pharmaceutical, and perfume grades, 99% min purity, liquid form
Bacteriostatic Water for Injection, USP is a sterile, nonpyrogenic preparation of water for injection containing 0.9% (9 mg/mL) of benzyl alcohol added as a bacteriostatic preservative. /Bacteriostatic Water for Injection/
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4.11 Protective Equipment and Clothing
RUBBER GLOVES; CHEMICAL SAFETY GOGGLES
Personnel protection: Wear appropriate chemical protective gloves, boots and goggles. /Benzyl alcohol (Combustible liquid, NOS)/
4.12 Reactivities and Incompatibilities
A mixture of benzyl alcohol with 58% sulfuric acid decomp expliosively at about 180 deg C.
Incompatible with oxidizing agents.
Possible problems may occur when polystyrene syringes are used with certain types of drug products that contain paraaldehyde, benzaldehyde & benzyl alcohol since these agents can extract & dissolve the plastic. At times the rubber tip of the plunger may release a constituent to the drug product.
Benzyl alcohol containing acidic constituents and dissolved iron was found to polymerize with a rapid temperature increase when heated in excess of 100 deg C. Amines, pyridene, and alkali hydroxides act as inhibitors and prevent polymerization.
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4.13 Skin, Eye, and Respiratory Irritations
It is slightly irritating to the skin.
Vapor: Irritating to eyes, nose and throat. Liquid: Irritating to skin & eyes.
4.14 Safety
Hazard Codes:Xn,T
Risk Statements:20/22-63-43-36/37/38-23/24/25-45-40
20/22:Harmful by inhalation and if swallowed
63:Possible risk of harm to the unborn child
43:May cause sensitization by skin contact
36/37/38:Irritating to eyes, respiratory system and skin
23/24/25:Toxic by inhalation, in contact with skin and if swallowed
45:May cause cancer
40:Limited evidence of a carcinogenic effect
Safety Statements:26-36/37-24/25-23-53
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37:Wear suitable protective clothing and gloves
24/25:Avoid contact with skin and eyes
23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
53:Avoid exposure - obtain special instruction before use
RIDADR:UN 1593 6.1/PG 3
WGK Germany:1
Hazardous Substances Data:100-51-6(Hazardous Substances Data)
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4.15 Toxicity
Inhalation of vapor may cause irritation of upper respiratory tract. Prolonged or excessive inhalation may result in headache, nausea, vomiting, and diarrhea. In severe cases, respiratory stimulation followed by respiratory and muscular paralysis, convulsions, narcosis and death may result. Ingestion may produce severe irritation of the gastrointestinal tract, followed by nausea, vomiting, cramps and diarrhea; tissue ulceration may result. Contact with eyes causes local irritation. Material can be absorbed through skin with anesthetic or irritant effect.
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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Inhalation, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed

H332 Harmful if inhaled
Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
ESR : REACTION WITH OH IN H2SO4  
ESR : REACTION WITH OH IN H2SO4(0.5 MOL)  
13C NMR : in CDCl3  
13C NMR : Predict  
1H NMR : 400 MHz in CDCl3  
1H NMR : 90 MHz in CDCl3  
1H NMR : Predict  
Predict 1H proton NMR  
IR : CCl4 solution  
IR : liquid film  
Raman : 4880 A,100M,liquid  
Mass  
Mass spectrum (electron ionization)  
7. Synthesis Route
100-51-6Total: 1051 Synthesis Route
 
98-88-4
98-88-4 251 Suppliers
 
100-51-6
100-51-6 830 Suppliers
 
65-85-0
65-85-0 917 Suppliers
 
100-51-6
100-51-6 830 Suppliers
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8. Precursor and Product
precursor:
93-58-3
93-58-3
98-88-4
98-88-4
55-21-0
55-21-0
71-41-0
71-41-0
93-99-2
93-99-2
88-67-5
88-67-5
93-89-0
93-89-0
93-98-1
93-98-1
65-85-0
65-85-0
93-97-0
93-97-0
product:
84-54-8
84-54-8
98-88-4
98-88-4
55-21-0
55-21-0
60-12-8
60-12-8
85-52-9
85-52-9
91-21-4
91-21-4
87-41-2
87-41-2
65-85-0
65-85-0
89-95-2
89-95-2
90-01-7
90-01-7
9. Computed Properties
10.Other Information
Usage
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. It is employed as a local anesthetic which reduces the pain associated with lidocaine injection. It 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.
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Merck
14,1124
BRN
878307
Overviews
Phenylcarbinol is also known as benzyl alcohol. Its chemical formula is C6H5CH2OH and its density is 1.045 g/mL at 25 ° C (lit). Benzylalcohol is one of the simplest fatty alcohol containing phenyl. It can be seen as benzene substituted by hydroxymethyl, or methyl alcohol substituted by phenyl. It is a colorless transparent sticky liquid with faint aroma. Sometimes benzyl alcohol is placed for a long time, it will smells like bitter almond flavor because of oxidation. Polarity, low toxicity and low steam, so it is used as alcohol solvent. It is combustible, and slightly soluble in water (about 25ml of water soluble 1 gram of benzyl alcohol). It is miscible with ethanol, ethyl ether, benzene, chloroform and other organic solvents.
Benzyl alcohol 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.
Benzyl alcohol should not be stored for a long time. It can be slowly oxidized to benzaldehyde and anisole in the air.Therefore benzyl alcohol products often smell like almond aroma with characteristic of benzaldehyde. In addition, benzyl alcohol is also easily oxidized to benzoic acid by many kinds of antioxidants such as nitric acid.
Benzyl alcohol has a narcotic effect. It has a strong stimulating effect on the eye, skin and respiratory system. Ingestion, inhalation or skin contact is harmful to the body. One will feel headache, nausea, vomiting, gastrointestinal irritation, convulsion, coma after ingestion of benzyl alcohol. It can lead to death under serious condition. Median lethal dose in rats is 1230mg/kg. When benzyl alcohol enters the body, it is firstly oxidized to benzoic acid and then condenses with glycine in the liver to form hippuric acid and excrets. Intramuscular injection using benzyl alcohol as solvent may result in gluteal muscle contracture.
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Chemical Properties
Benzyl alcohol 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.
Uses
Benzyl alcohol is a colorless clear oily liquid; its odor type is floral and its odor at 100% is described as 'floral rose phenolic balsamic'.Benzyl alcohol is used in cosmetics as afragrance component, preservative, solvent and diluting agent for perfumes and flavors, and viscosity-decreasing agent. It 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. It is added in small amounts to surface-coating materials to improve their flow and gloss. In the textile industry, benzyl alcohol is used as anauxiliary in the dyeing of wool, polyamides, and polyesters. In pharmacy it 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).
Benzyl alcohol 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).
Benzyl alcohol may be found, in among other things, adhesives, binders, castings, cleaning agents,construction material, fillings,flooring materials, hardeners, metal coatings, paints/lacquers, photo developers,printings inks, skin care products and injectable solutions.
It should be realized that, by far, most adverse reactions to benzyl alcohol reported were from its use as a preservative rather than from its application as a fragrance ingredient. The literature on allergy to benzyl alcohol has been reviewed in 1999 and in 2005.
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Production Method
1.Benzyl chloride 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 benzyl alcohol at 65~75 ℃. The product has high purity.
3.Using benzyl chloride as raw materials, it 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 benzyl alcohol 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 it 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
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Description
Benzyl alcohol is a component catalyst for epoxy resins. It is also contained in the color developer C-22.
Chemical Properties
Benzyl alcohol occurs in many essential oils and foods. It is a colorless liquid with a weak, slightly sweet odor. Benzyl alcohol 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 benzyl alcohol 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 benzyl alcohol in the presence of strong acids or strong bases, dibenzyl ether is formed.
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Physical properties
Colorless, hygroscopic, air sensitive liquid with a faint, pleasant, aromatic odor. Odor threshold concentration in water is 10 ppm (Buttery et al., 1988).
Occurrence
The free alcohol is often present in several essential oils and extracts of jasmine, tobacco, tea, neroli, copaiba, Acacia farnesiana Willd., Acacia cavenia Hook. and Arn., Robinia pseudacacia, ylang-ylang, Pandanus odoratissimus, Michelia champaca, Prunus laurocerasus, tuberose, orris, castoreum, violet leaves, clove buds and others. Also found in fresh apple, apricot, mandarin peel oil, high bush blueberry, raspberry, strawberry fruit, American cranberry and cooked asparagus.
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Uses
Esters of benzyl alcohol are used in makingperfume, soap, flavoring, lotion, and ointment.It finds application in color photography;the pharmaceuticals industry, cosmetics,and leather dyeing; and as an insect repellent.It occurs in natural products such as oils ofjasmine and castoreum.
Uses
benzyl alcohol is a preservative against bacteria, used in concentrations of 1 to 3 percent. It can cause skin irritation.
Definition
ChEBI: An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.
Production Methods
Benzyl alcohol is prepared commercially by the distillation of benzyl chloride with potassium or sodium carbonate. It may also be prepared by the Cannizzaro reaction of benzaldehyde and potassium hydroxide.
Definition
An aromatic primary alcohol. Phenylmethanol 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
Phenylmethanol 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.
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Preparation
By the action of alkalis on benzyl chloride
World Health Organization (WHO)
Benzyl alcohol has been used as an antimicrobial agent in pharmaceutical preparations for many years. Parenteral administration of preparations containing 0.9% benzyl alcohol 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.
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Aroma threshold values
Detection: 1.2 to 1000 ppb; also 10 to 1000 ppm.
Taste threshold values
Taste characteristics at 50 ppm: chemical, fruity with balsamic nuances.
Synthesis Reference(s)
Chemical and Pharmaceutical Bulletin, 36, p. 3628, 1988 DOI: 10.1248/cpb.36.3628
Journal of the American Chemical Society, 107, p. 2428, 1985 DOI: 10.1021/ja00294a038
Tetrahedron Letters, 35, p. 1515, 1994 DOI: 10.1016/S0040-4039(00)76746-3
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General Description
A clear colorless liquid with a pleasant odor. Slightly denser than water. Flash point 194°F. Boiling point 401°F. Contact may irritate skin, eyes, and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
Attacks plastics. [Handling Chemicals Safely 1980. p. 236]. Acetyl bromide reacts violently with alcohols or water [Merck 11th ed. 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: an explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73 1967; J, Org. Chem. 28:1893 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].
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Hazard
Highly toxic.
Health Hazard
Benzyl alcohol is a low acute toxicant witha mild irritation effect on the skin. Theirritation in 24 hours from the pure compoundwas mild on rabbit skin and moderateon pig skin. A dose of 750 μg producedsevere eye irritation in rabbits. The toxicityof benzyl alcohol is of low order,the effects varying with the species. Oralintake of high concentrations of this compoundproduced behavioral effects in rats.The symptoms progressed from somnolenceand excitement to coma. Intravenous administrationin dogs produced ataxia, dyspnea,diarrhea, and hypermotility in the animals.
Adult and neonatal mice treated withbenzyl alcohol exhibited behavioral change,including sedation, dyspnea, and loss ofmotor function. Pretreatment with pyrazoleincreased the toxicity of benzyl alcohol. Withdisulfiram the toxicity remained unchanged.The study indicated that the acute toxicitywas due to the alcohol itself andnot to bezaldehyde, its primary metabolite(McCloskey et al. 1986).
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Fire Hazard
Benzyl alcohol is combustible.
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: Will attack some plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Pharmaceutical Applications
Benzyl alcohol 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 it 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.
Benzyl alcohol 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, benzyl alcohol has been associated with some fatal adverse reactions when administered to neonates. It 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.
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Contact allergens
Benzyl alcohol is mainly a preservative, mostly used in topical antimycotic or corticosteroid ointments. It is also a component catalyst for epoxy resins and is contained in the color developer C-22. As a fragrance allergen, it has to be mentioned by name in cosmetics within the EU.
Safety
Benzyl alcohol is used in a wide variety of pharmaceutical formulations. It is metabolized to benzoic acid, which is further metabolized in the liver by conjugation with glycine to form hippuric acid, which is excreted in the urine.
Ingestion or inhalation of benzyl alcohol may cause headache, vertigo, nausea, vomiting, and diarrhea. Overexposure may result in CNS depression and respiratory failure. However, the concentrations of benzyl alcohol normally employed as a preservative are not associated with such adverse effects.
Reports of adverse reactions to benzyl alcohol used as an excipient include toxicity following intravenous administration; neurotoxicity in patients administered benzyl alcohol in intrathecal preparations; hypersensitivity, although relatively rare; and a fatal toxic syndrome in premature infants.
The fatal toxic syndrome in low-birth-weight neonates, which includes symptoms of metabolic acidosis and respiratory depression, was attributed to the use of benzyl alcohol as a preservative in solutions used to flush umbilical catheters. As a result of this, the FDA has recommended that benzyl alcohol should not be used in such flushing solutions and has advised against the use of medicines containing preservatives in the newborn.
The WHO has set the estimated acceptable daily intake of the benzyl/benzoic moiety at up to 5 mg/kg body-weight daily.
LD50 (mouse, IV): 0.32 g/kg
LD50 (mouse, oral): 1.36 g/kg
LD50 (rat, IP): 0.4 g/kg
LD50 (rat, IV): 0.05 g/kg
LD50 (rat, oral): 1.23 g/kg
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Chemical Synthesis
By saponification of the ester present in Tolu and Pery balsams; synthetically, it is obtained from benzyl chloride by the action of sodium or potassium carbonate.
Carcinogenicity
In an NTP study, F344 rats were dosed by oral gavage with 0, 200, and 400 mg/kg, 5 days/ week for 2 years. Benzyl alcohol had no effect on the survival of male rats; female rats had reduced survival, and many of the early deaths were considered related to the gavage procedure. There were no treatment-related effects on nonneoplastic or neoplastic lesions in either sex treated with benzyl alcohol. It was concluded that under the conditions of the study, there was no evidence of carcinogenic activity . In the same NTP study, B6C3F1 mice were dosed by oral gavage with 0, 100, and 200 mg/kg, 5 days/week for 2 years. No effects on survival or body weight gain were observed. There were no treatment-related effects on nonneoplastic or neoplastic lesions in either sex. It was concluded that under the conditions of the study, there was no evidence of carcinogenic activity.
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Source
Benzyl alcohol naturally occurs in tea (900 ppm), daffodils (165–330 ppm), hyacinths (64–920 ppm), jasmine (120–228 ppm) rosemary (7–32 ppm), hyssop (0.1–30 ppm), tangerines (1–2 ppm), blueberries (0.01–0.08 ppm in fruit juice), ylang-ylang, colocynth, licorice, roselle, tomatoes, spearmint, sweet basil, apricots, tuberose (Duke, 1992), and small-flowered oregano shoots (2 ppm) (Baser et al., 1991). Also identified among 139 volatile compounds identified in cantaloupe (Cucumis melo var. reticulates cv. Sol Real) using an automated rapid headspace solid phase microextraction method (Beaulieu and Grimm, 2001).
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Environmental fate
Biological. Heukelekian and Rand (1955) reported a 5-d BOD value of 1.55 g/g which is 61.5% of the ThOD value of 2.52 g/g.
Chemical/Physical. Slowly oxidizes in air to benzaldehyde (Huntress and Mulliken, 1941). Benzyl alcohol will not hydrolyze because it has no hydrolyzable functional group (Kollig, 1993).
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Metabolism
Esters of benzyl alcohol are rapidly hydrolysed in vivo to benzyl alcohol, which is then oxidized . The animal organism readily oxidizes benzyl alcohol to benzoic acid, which after conjugation with glycine is rapidly eliminated as hippuric acid in the urine.
Metabolism of benzyl alcohol
Benzyl alcohol is oxidised by alcohol dehydrogenase (AlcDH), a cytoplasmic enzyme present mainly in the liver, but also in the intestine and kidney. This reaction is saturable. The benzaldehyde formed is oxidised by aldehyde dehydrogenases (AldDH), cytoplasmic and mitochondrial enzymes mainly present in the liver, but also in the intestine and numerous organs.
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storage
Benzyl alcohol oxidizes slowly in air to benzaldehyde and benzoic acid; it does not react with water. Aqueous solutions may be sterilized by filtration or autoclaving; some solutions may generate benzaldehyde during autoclaving.
Benzyl alcohol may be stored in metal or glass containers. Plastic containers should not be used; exceptions to this include polypropylene containers or vessels coated with inert fluorinated polymers such as Teflon.
Benzyl alcohol should be stored in an airtight container, protected from light, in a cool, dry place.
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Purification Methods
It is usually purified by careful fractional distillation under reduced pressure in the absence of air. Benzaldehyde, if present, can be detected by UV absorption at 283nm. It has also been purified by shaking with aqueous KOH and extracting with peroxide-free diethyl ether. After washing with water, the extract is treated with saturated NaHS solution, filtered, washed, dried with CaO and distilled under reduced pressure [Mathews J Am Chem Soc 48 562 1926]. Peroxy compounds can be removed by shaking with a solution of Fe2+ followed by washing the alcohol layer with distilled water and fractionally distilling it. [Beilstein 6 IV 2222.]
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Toxicity evaluation
Due to an abundance of useful applications across society, from industrial production to consumer products, benzyl alcohol is present in the environment and is steadily released through commercial and household waste streams. Benzyl alcohol was an early object of chemists striving for greener synthetic approaches involving mixed catalysts for oxidation. It is released into the atmosphere entirely as a vapor due to its high vapor pressure, where it is lost by degradation involving reaction with hydroxyl radicals at a half-life of about 2 days. Benzyl alcohol is expected to have quite high mobility based upon its soil to water partition coefficient, and a projected soil half-life of about 13 days.
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Incompatibilities
Benzyl alcohol is incompatible with oxidizing agents and strong acids. It can also accelerate the autoxidation of fats. Although antimicrobial activity is reduced in the presence of nonionic surfactants, such as polysorbate 80, the reduction is less than is the case with hydroxybenzoate esters or quaternary ammonium compounds.
Benzyl alcohol is incompatible with methylcellulose and is only slowly sorbed by closures composed of natural rubber, neoprene, and butyl rubber closures, the resistance of which can be enhanced by coating with fluorinated polymers. However, a 2% v/v aqueous solution in a polyethylene container, stored at 208℃, may lose up to 15% of its benzyl alcohol content in 13 weeks. Losses to polyvinyl chloride and polypropylene containers under similar conditions are usually negligible. Benzyl alcohol can damage polystyrene syringes by extracting some soluble components
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Regulatory Status
Included in the FDA Inactive Ingredients Database (dental injections, oral capsules, solutions and tablets, topical, and vaginal preparations). Included in parenteral and nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
Overviews
Phenylcarbinol is also known as benzyl alcohol. Its chemical formula is C6H5CH2OH and its density is 1.045 g/mL at 25 ° C (lit). Benzylalcohol is one of the simplest fatty alcohol containing phenyl. It can be seen as benzene substituted by hydroxymethyl, or methyl alcohol substituted by phenyl. It is a colorless transparent sticky liquid with faint aroma. Sometimes benzyl alcohol is placed for a long time, it will smells like bitter almond flavor because of oxidation. Polarity, low toxicity and low steam, so it is used as alcohol solvent. It is combustible, and slightly soluble in water (about 25ml of water soluble 1 gram of benzyl alcohol). It is miscible with ethanol, ethyl ether, benzene, chloroform and other organic solvents.
Benzyl alcohol 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.
Benzyl alcohol should not be stored for a long time. It can be slowly oxidized to benzaldehyde and anisole in the air.Therefore benzyl alcohol products often smell like almond aroma with characteristic of benzaldehyde. In addition, benzyl alcohol is also easily oxidized to benzoic acid by many kinds of antioxidants such as nitric acid.
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Definition
ChEBI: Benzyl alcohol is an aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent. It has a role as a solvent, a metabolite, an antioxidant and a fragrance.
Flammability and Explosibility
Nonflammable
Storage Conditions
1. Benzyl alcohol is naturally occurring in orange blossom, ylang ylang, jasmine, gardenia, acacia, lilac, hyacinth, industrial benzyl chloride or benzaldehyde as raw materials. In 12% of the soda solution by adding benzyl chloride, heated to 93 ° C stirring reaction 5h, and then heated to 101 ~ 103 ° C to continue the reaction 10h. After the reaction, cooling to room temperature, adding salt to saturation, standing stratification, take the upper layer of crude oil distillation pressure, and refined products. The yield was 70% ~ 72%. In the presence of sodium hydroxide formaldehyde and benzaldehyde, the disproportionation reaction of benzyl alcohol. 2 to benzyl chloride as raw material, in the base of the catalytic hydrolysis derived hydrolysis. 3. Mix benzyl chloride, sodium carbonate and water in a certain proportion, stir quickly, emulsify the oil layer, raise the temperature to 90 ° C while stirring. When the generated carbon dioxide gas no longer escapes, continue heating to 101 ~ 103 ° C to complete the hydrolysis reaction: cooling after the end of the reaction, standing layered. Take the oil layer washed several times, into the water layer, and then atmospheric distillation, the first steamed water, benzyl chloride and other low boiling, as the initial fraction, and then collected 203 ~ 206 ℃ as the main distillate, is finished. BU, OR, 18; FC, BU, OR, 40; 5. Method: In a reaction flask equipped with a stirrer, a reflux condenser and a thermometer, 250 mL of water, 56 g of sodium carbonate, (2) (63.3 g, 0.5 mol) was added thereto, followed by vigorous stirring to emulsify benzyl chloride. Was added to the micro boil (about 95 & lt; 0 & gt; C). Carbon dioxide is produced in the reaction. Stop the escape of carbon dioxide bubbles that the reaction is completed, and then stirring reaction 0.5h. Cooling, separation of the organic layer, washed with water, crude benzyl alcohol. Fractionation, collecting 204 ~ 205 ° C distillate, in benzyl alcohol ① (1) in a yield of 74%.
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Storage features
Separated from strong oxidants.
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