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Acetophenone structure

Acetophenone
  • CAS：98-86-2
  • MW:120.14852
  • MF：C8H8O
Acetophenone, with the chemical formula C8H8O and CAS registry number 98-86-2, is a compound known for its aromatic fragrance and use in various industries. This colorless liquid, also referred to as phenyl methyl ketone, is characterized by its carbonyl group attached to a phenyl ring. It is commonly used as a solvent, flavoring agent, and intermediate in the production of pharmaceuticals, dyes, and perfumes. Acetophenone has been studied for its potential antimicrobial and antioxidant properties. It is an important compound in the field of organic chemistry and chemical synthesis, contributing to the development of new materials and compounds.
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1. Names and Identifiers
1.1 Name
Acetophenone
1.2 Synonyms
1-Phenylethanone; 1VR; Acetofenon; Acetophenon; acetophenon[qr]; ACETOPHENONE extrapure AR; ACETOPHENONE, 1X1ML, CH2CL2, 2000UG/ML; acetyl-benzen; acetylbenzene; Benzene, acetyl-; EINECS 202-708-7; Ethanone, 1-phenyl-; Ethanone,1-phenyl; METHYL PHENYL KETONE; MFCD00008724; Oxophenylethane; Phenyl methyl ketone; usafek-496[qr];
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1.3 CAS No.
98-86-2
1.4 CID
7410
1.5 EINECS
202-708-7
1.6 Molecular Formula
C8H8O
1.7 Inchi
InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3
1.8 InChkey
KWOLFJPFCHCOCG-UHFFFAOYSA-N
1.9 Canonical Smiles
CC(=O)C1=CC=CC=C1
1.10 Isomers Smiles
CC(=O)C1=CC=CC=C1
2. Properties
2.1 Vapour pressure
4.1 (vs air)
2.2 Solubility
6.1g/l
2.3 Viscosity
1.681 mPa.s
2.4 VaporDensity
4.1 (vs air)
2.5 Appearance
clear to light yellow liquid
2.6 Atmospheric OH Rate Constant
2.74e-12 cm3/molecule*sec
2.7 Storage
Ambient temperatures.
2.8 Autoignition Temperature
1058 °F (USCG, 1999)
2.9 Carcinogenicity
No carcinogenicity studies wereidentified for acetophenone. The U.S. EPA has classifiedacetophenone as a Category D, not classifiable as to humancarcinogenicity.
2.10 Color/Form
Liquid. Forms laminer crystals at low temperature.
2.11 Decomposition
Hazardous decomposition products formed under fire conditions - Carbon oxides.
2.12 Heat of Combustion
-8,250 cal/g
2.13 Heat of Vaporization
83.6 cal/g
2.14 HenrysLawConstant
1.04e-05 atm-m3/mole
2.15 Odor
Sweet pungent odor
2.16 Odor Threshold
0.8347 mg/cu m (odor low) 2.9460 (odor high)
2.17 pKa
pKa1 -6.4 (25 °, H2SO4 aq.)
2.18 Water Solubility
5.5 g/L (20 oC)
2.19 Spectral Properties
Index of refraction: 1.5339 @ 20 deg C/D
MAX ABSORPTION (ALC): 243 NM (LOG E= 4.12); SADTLER REFERENCE NUMBER: 3226 (IR, PRISM); 8290 (IR, GRATING); 953 (UV)
IR: 5181 (Coblentz Society Spectral Collection)
UV: 08-7 (Documentation of Molecular Spectroscopy Collection)
NMR: 192 (Varian Associates NMR Spectra Catalogue)
MASS: 61522 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)
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2.20 Stability
Stable. Incompatible with strong oxidizing agents, strong bases, strong reducing agents. Combustible.
2.21 StorageTemp
Store below +30°C.
2.22 Surface Tension
39.04 mN/m at 25 °C
3. Use and Manufacturing
3.1 Definition
ChEBI: A methyl ketone that is acetone in which one of the hydrogens of the methyl group has been replaced by a phenyl group.
3.2 Description
Acetophenone (CAS 98-86-2) is a colorless liquid with a sweet, floral odor. It has a molecular structure consisting of a phenyl group attached to a carbonyl group. Acetophenone is soluble in organic solvents such as ethanol and ether, but only slightly soluble in water. It has a boiling point of 202-203°C and a melting point of -15°C. This chemical is highly flammable and can form explosive mixtures with air. It reacts with strong oxidizing agents and can undergo various chemical reactions, including oxidation, reduction, and condensation reactions.

Applicable Fields
Acetophenone has several applications in different industries:

Pharmaceutical Industry: Acetophenone is used as an intermediate in the synthesis of various pharmaceutical compounds. It serves as a starting material for the production of analgesics, antiseptics, and other pharmaceutical products. The mechanism of action in these applications involves its role as a precursor in chemical reactions to form desired pharmaceutical compounds.

Perfume and Fragrance Industry: Acetophenone is widely used in the perfume and fragrance industry due to its pleasant odor. It is used as a fragrance ingredient in perfumes, soaps, lotions, and other personal care products. The mechanism of action in this field is its ability to contribute to the overall scent profile of the product.

Chemical Synthesis: Acetophenone is utilized as a reagent in various chemical reactions. It can undergo condensation reactions to form derivatives such as acetophenone oxime and acetophenone hydrazone. These derivatives are used in the synthesis of other organic compounds. The mechanism of action involves its participation in chemical reactions to form new compounds.

Storage Conditions
Store in a cool, dry place.
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3.3 Potential Exposure
Acetophenone is used as a solvent and in perfume manufacture to impact a pleasant jasmine or orange-blossom odor. It is used as a catalyst in olefin polymerization and as a flavorant in tobacco. It is also used in the synthesis of pharmaceuticals
3.4 Shipping
UN1993 Flammable liquids, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, Technical Name Required.
3.5 Usage

In perfumery to impart an orange-blossom-like odor, catalyst for polymerization of olefins, in organic synthesis, esp as photosensitizer.

4. Safety and Handling
4.1 Exposure Standards and Regulations
Synthetic flavoring substances and adjuvants may be safely used in food in accordance with the following conditions. a) They are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice. b) They consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part. Acetophenone is included on this list.
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4.2 Octanol/Water Partition Coefficient
log Kow= 1.58
4.3 Other Preventative Measures
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
Protect eyes & skin from direct contact.
Adequate ventilation... should be provided in those operations where acetophenone is heated to elevated temperatures.
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.
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4.4 Cleanup Methods
Absorb on paper. Evaporate on a glass or iron dish in hood. Burn the paper.
4.5 DisposalMethods
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U004, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 deg C and a residence time of 0.1 to 2 seconds. A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 deg C and residence times of seconds for liquids and gases, and longer for solids.
The following wastewater treatment technologies have been investigated for acetophenone: concentration process: activated carbon.
The following wastewater treatment technologies have been investigated for acetophone: concentration process: resin adsorption.
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4.6 Fire Fighting Procedures
Extinguish with water, foam, dry chemical, carbon dioxide.
4.7 FirePotential
... /It/ does not form flammable mixtures with air at room temperature.
Slight, when exposed to heat or flame; can react with oxidizing materials.
Combustible.
4.8 Safety Profile
Poison by intraperitoneal and subcutaneous routesModerately toxic by ingestion. A skin and severe eye irritant. Mutation data reported. Narcotic in high concentration. A hypnotic. Flammable liquid. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes. See also IGTONES
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4.9 Formulations/Preparations
Trade Name: Hypnone
Grades: technical, refined, perfumery.
99.0% minimum purity liquid grade. /Commercially available from ARCO/
4.10 Incompatibilities
May form explosive mixture with air. See flash point, above. Reacts violently with strong oxidizers, many acids, bases, amines, amides, and inorganic hydroxides; alkali metals; hydrides, and nitrides. Reacts with reducing agents; alkali metals; hydrides, nitrides. Contact with all preceding materials release heat and flammable gases, including hydrogen; the heat may be sufficient enough to result in fire. Incompatible with aldehydes, aliphatic amines, alkanolamines, cyanides, isocyanates, organic acids, peroxides; perchloric acid. May attack plastics, and some rubbers and coatings
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4.11 Protective Equipment and Clothing
Liquid or solid: Irritating to skin or eyes. Harmful if swallowed.
4.12 Skin, Eye, and Respiratory Irritations
Liquid or solid: Irritating to skin or eyes. Harmful if swallowed.
4.13 Safety

Hazard Codes:?HarmfulXn,?ToxicT,?FlammableF
Risk Statements: 22-36-63-43-36/37/38-23/24/25-45-39/23/24/25-11?
R22:Harmful if swallowed.?
R36:Irritating to eyes.?
R63:Possible risk of harm to the unborn child.?
R36/37/38:Irritating to eyes, respiratory system and skin.?
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.?
R45:May cause cancer.?
R39:Danger of very serious irreversible effects.?
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.?
R11:Highly flammable.
Safety Statements: 26-36/37-24/25-23-53-45-16-7?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37:Wear suitable protective clothing and gloves.?
S24/25:Avoid contact with skin and eyes.?
S23:Do not breathe vapour.?
S53:Avoid exposure - obtain special instructions before use.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S16:Keep away from sources of ignition.?
S7:Keep container tightly closed.
RIDADR: UN 1593 6.1/PG 3
WGK Germany: 1
RTECS: AM5250000
F: 8
HS Code: 29143900
Hazardous Substances Data: 98-86-2(Hazardous Substances Data)

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4.14 Specification

?Acetophenone (CAS NO.98-86-2) is also named as 1-Phenyl-1-ethanone ; 1-Phenylethanone ; AI3-00575 ; Acetofenon ; Acetofenon [Czech] ; Acetophenon ; Acetylbenzene ; Acetylbenzol ; Benzene, acetyl- ; Benzoyl methide ; Benzoylmethide ; CCRIS 1341 ; Ethanone, 1-phenyl- ; FEMA No. 2009 ; FEMA Number 2009 ; HSDB 969 ; Hypnone ; Ketone, methyl phenyl ; Methyl phenyl ketone ; NSC 7635 ; Phenyl methyl ketone ; RCRA waste number U004 ; UNII-RK493WHV10 ; USAF EK-496 .?Acetophenone (CAS NO.98-86-2) is yellow liquid with a sweet pungent taste. It is slightly soluble in water. Vapor heavier than air. A mild irritant to skin and eyes. Vapors can be narcotic in high concentrations. Acetophenone reacts with many acids and bases liberating heat and flammable gases (e.g., H2). Reacts with many oxidizing agents. Reacts with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. The amount of heat in these reactions may be sufficient to start a fire in the unreacted portion. It ia incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. No toxicity expected from inhalation or ingestion except slight narcotic effect. Liquid can cause eye and skin irritation on contact.

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4.15 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 skin > 20mL/kg (20mL/kg) ? Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 269, 1944.
mammal (species unspecified) LC50 inhalation 1200mg/m3 (1200mg/m3) ? Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.
mammal (species unspecified) LD50 oral 2700mg/kg (2700mg/kg) ? Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.
mouse LD50 intraperitoneal 200mg/kg (200mg/kg) ? National Technical Information Service. Vol. AD277-689,
mouse LD50 oral 740mg/kg (740mg/kg) ? Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(8), Pg. 53, 1982.
mouse LDLo subcutaneous 330mg/kg (330mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) "Pharmakologische Prufung von Analgetika, Dissertation," Herrlen, G., Pharmakologischen Institut der Universitat Tubingen, Fed. Rep. Ger., 1933Vol. -, Pg. -, 1933.
rabbit LD50 skin 15900uL/kg (15.9mL/kg) ? Union Carbide Data Sheet. Vol. 12/27/1971,
rat LC inhalation > 210ppm/8H (210ppm) ? Union Carbide Data Sheet. Vol. 12/27/1971,
rat LD50 oral 815mg/kg (815mg/kg) ? Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(8), Pg. 53, 1982

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed

H319 Causes serious eye irritation
Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

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

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

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

P330 Rinse mouth.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

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 : ANION RADICAL, ELECTROLYTIC REDUCTION IN DME  
ESR : ANION RADICAL, ELECTROLYTIC REDUCTION IN DMF  
13C NMR : in CDCl3  
13C NMR : Predict  
1H NMR : 90 MHz in CDCl3  
1H NMR : in CDCl3  
1H NMR : Predict  
IR : CCl4 solution  
IR : liquid film  
Mass  
7. Synthesis Route
98-86-2Total: 1023 Synthesis Route
 
98-85-1
98-85-1 57 Suppliers
 
98-86-2
98-86-2 326 Suppliers
 
65-85-0
65-85-0 917 Suppliers
 
99-91-2
99-91-2 192 Suppliers
 
98-85-1
98-85-1 57 Suppliers
 
98-86-2
98-86-2 326 Suppliers
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8. Precursor and Product
precursor:
80-15-9
80-15-9
98-82-8
98-82-8
99-91-2
99-91-2
70-11-1
70-11-1
93-89-0
93-89-0
98-85-1
98-85-1
product:
92-71-7
92-71-7
55-21-0
55-21-0
83-33-0
83-33-0
92-06-8
92-06-8
60-12-8
60-12-8
98-81-7
98-81-7
70-11-1
70-11-1
94-02-0
94-02-0
65-85-0
65-85-0
93-92-5
93-92-5
9. Computed Properties
10.Other Information
Usage
Acetophenone is used as a raw material in the synthesis of active pharmaceutical ingredients such as dextropropoxyphene and phenylpropanolamine. It is employed in organic synthesis and as a polymerization catalyst for olefins. It is involved in the preparation of styrene, 1-phenylethanol. It is also used as a active component of coatings and inks. It reacts with formaldehyde to prepare resins. Further, it is used in textile coatings, in perfumes for orange blossom odor. In addition to this, it is used as a solvent in plastics, adhesives and a flavoring agent in foods.
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Merck
14,73
BRN
605842
General description
Acetophenone is also known as acetyl benzene with the boiling point (℃) being 202.3, relative density (water = 1) being 1.03 (20 ℃) and the relative vapor density (air = 1) being 4.14. It is the simplest aromatic ketones with its aromatic core (benzene ring) being directly connected with a carbonyl group. It is presented in some kinds of essential oils of some plants in its free-state form. It is pure colorless crystals. Most commercially available product appears as pale yellow oily liquid with hawthorn like aroma. It is only slightly soluble in water and is easily soluble in many organic solvents and can be evaporated together with the steam. The molecular structure of acetophenone: methyl C atom is bonded through sp3 hybrid orbital while the benzene ring and the carbonyl C atom are bonded through sp2 hybrid orbital. Addition reaction and [alpha] active hydrogen reaction can occur for the carbonyl group of acetophenone. It can also have electrophilic substitution reaction in its benzene ring with the major product generated being in the meta-position. Acetophenone can be produced from the reaction between benzene with acetyl chloride, acetic anhydride or acetate under the catalysis of aluminum trichloride. Furthermore, when ethylbenzene is catalyzed and oxidized into styrene, it can also generate acetophenone as by-product. Acetophenone is mainly used as the raw materials for pharmaceuticals and other kind of organic synthesis. It can also used for the preparation of spices, soap and cigarettes as well as being used as the solvents of cellulose ether, cellulose ester and resin and plasticizer. It has hypnotic effect. Currently, acetophenone is mostly obtained via the by-product of reaction between phenol and acetone via cumene oxidation. It may be obtained through the acetylation on benzene through acetyl chloride.
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Preparation of acetophenone
Instruments and medicines
Drugs: acetic anhydride, benzene, magnesium sulfate, sodium hydroxide, aluminum chloride, hydrochloride;
Instrument: dropping funnel, round bottom flask, condenser pipe, distillation device, drying pipe, and stirring apparatus.
[Processing Steps]
To a 100 mL three-necked flask equipped with 10 ml pressure-equalizing dropping funnel, a mechanical stirrer and a reflux condenser (the upper termini is connected with a hydrogen chloride gas absorption device via a calcium chloride drying tube), add rapidly of 13 g (0.097mol) of anhydrous powdered aluminum trichloride and 16 ml (about 14g, 0.18mol) of anhydrous benzene. Under stirring, add 4 mL (about 4.3g, 0.04mol) of acetic anhydride from a dropping funnel drop wise to a three-necked flask (first add few drops and continue the dropping after the occurrence of the reaction). It is recommended to make the three-necked flask a bit heat through controlling the dropping rate of the acetic anhydride. After the completion of the addition process (about 10 min), stir and reflux in the boiling water bath until the reaction becomes a bit moderate until no more hydrogen chloride gas is released.
The reaction mixture was cooled to room temperature. Upon stirring, pour the reaction mixture to a beaker containing 18 mL of hydrochloric acid and 30 g of broken ices (in a fume hood), and if there is still solid insolubles, you can supplement an appropriate amount of concentrated hydrochloric acid to make it be completely dissolved. The mixture was transferred to a separatory funnel with the organic layer being separated (which one?) and the aqueous layer was extracted twice with benzene (per 8ml). Combine the organic layers and successively wash with 15 mL of 10% sodium hydroxide, 15 ml of water and dry with anhydrous magnesium sulfate.
First distill for recycle of benzene in a water bath and then heat in the asbestos-free wire gauze residual to remove the benzene. After the cooling, change to the air condenser (Why?) Distill to collect the fraction of 195~202 ℃ with the yield being about 4.1 g (yield: 85%) . The pure product of acetophenone appears as colorless transparent oily liquid.
[Precautions]
1, the time for adding drop wise of the mixture of acetophenone and acetic anhydride should be 10 min; the temperature is difficult to be controlled if the drops rate is too fast.
2, the quality of the anhydrous aluminum chloride is the key for the success of this experiment opening the lid with the white powder can release a lot of smoke with no agglomeration being good. If most of the fraction turns yellow, this means that it has been already degraded and can’t not been used any more.
3, AlCl3 needs to be crushed with rapid speed.
4, upon the addition of dilute HCl, slowly drop at the beginning and then drop faster gradually; the amount of the dilute HCl (1: 1, pre-prepared) should be about 140ml.
5, the absorption apparatus: about 20% sodium hydroxide solution, self-made, 200mL, pay special attention to the prevention of suck-buck.
6, it is better to use analytically pure benzene and should be preferably dried by sodium silk for 24 hours or more.
7, the small amount of water in the crude product is distilled out together with benzene as an azeotrope during the process of distillation with the azeotropic point being 69.4 °C. This is also one of the methods for drying a liquid compound.
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Characterization of acetophenone production via acylation reaction of Friedel-Craffs
1, the catalyst (aluminum trichloride) used in the acylation greatly exceeds the amount of the catalyst used in the alkylation reaction, the resulting acetophenone can form complex with an equivalent amount of aluminum chloride while by-product acetic acid formed in the reaction can also form salt with an equivalent of aluminum chloride. Therefore, during the acylation reaction, one molecule of acid anhydride can consume two or more molecules of aluminum chloride.
2, acetophenone/aluminum chloride complex formed during the reaction is stable in anhydrous medium, only when the reaction mixture undergoes hydrolysis, the complex is destroyed with precipitating acetophenone. After the aluminum chloride forms complex with acetophenone, it no longer participates in the reaction, therefore, the amount of aluminum chloride should meet the requirement that: after the formation of complex, there still remains certain part as the catalyst of the acylation reaction.
3, since the aluminum chloride can form a complex with substance containing a carboxyl group, the raw material, acetic anhydride can also form molecular complex with aluminum chloride and no longer participate in the reaction, meaning that acetic anhydride can’t been quantitatively converted to acetophenone; Furthermore, in the reaction, when the amount of aluminum chloride is in excess, it can act as the acylating agent for making the acetate into acetyl chloride to participate into the reaction.
4, in the reaction system, the amount of benzene is also in large excess because the benzene is not only the reactant but also the solvent in the reaction, therefore, only the yield of acetyl can be used as the reference reagent.
5, the characteristics of the acylation reaction: pure product, high yield (since acyl does not have isomerization, nor has multiple substitution)
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Content Analysis
Accurately weigh sample of about 1g, determine it according to the method 1 in the "determination of aldehydes and ketones" (OT-7), wherein the heating time was 1h and the equivalency factors (e) in the calculation was 60.08.
Chemical Properties
The pure product is white plate-like crystal. The general merchandises always contain impurities. At temperature above 20 °C, it is colorless or slightly yellow transparent liquid above with strong acacia-like sweet aroma. It has the melting point of 19.7 ℃, boiling point of 202 ℃ and the flash point of 76 ℃. It can be subject to spontaneous burning. It is extremely easily to be dissolved in propylene glycol and non-volatile oil, soluble in chloroform, ether and ethanol (1ml dissolved in 5mL 50% ethanol), slightly soluble in water and propylene glycol and insoluble in glycerol.
The natural product is presented in labdanum oil and orris oil.
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Uses
When being used as a solvent, it is characterized with high boiling point, high stability and pleasant odor. It has a similar solubility as cyclohexanone and can dissolved nitrocellulose; cellulose acetate; vinyl resin; coumarone resins; alkyd resins; glycerol alkyd resins. It is often used in mixture with ethanol; ketones; esters and other solvents. When being used as a spice, it is the blending raw material of spices of hawthorn; Mimosa and lilac and is widely applied to soap flavor and tobacco flavor. It is used for the synthesis of mandelic acid; α-phenyl indole and ibuprofen as well as being used as the plastic plasticizer.
Naturally-existing: it is presented in milk, cheese, cocoa, raspberries, peas and Sri Lanka cinnamon oil.
Odor: it has almond flavor similar as benzaldehyde with dilution generating a sweet nut and fruit-like flavor.
Application suggestions: it can be applied to the formulation of editable spices of cherries, nuts, tomatoes, strawberries, apricots and s on. It can also be used in tobacco spice.
Recommendation: the final concentration in the flavoring foods should be about 0.6~20mg/kg.
Regulatory information: The FEMA number of acetophenone is 2009, FDA number is 172.515, CoE number is 138. China GB 2760-1996 has approved it for being applied to food spices.
GB 2760--1996 provides it for the use of food flavors. It is mainly used for preparation of the spices of grapes, cherries and other fruits and tobacco.
It can be used as solvent, extraction agent as well as being applied to pharmaceutical industry.
It can be used as a solvent, olefin polymerization catalyst as well as being used for the manufacture of spices.
It can be used in combination with anise aldehyde and coumarin to spices of hawthorn flowers, sunflower, new mow, lavender, fern, lilac, shy flowers and acacia. Because of its cheap price, it is often applied to the perfuming of soap, detergents, and industrial product in a small amount (<1%). It can also be applied to food flavor such as almond, cherry, walnut, vanilla and tonka bean in trace amount. It can also be applied to the perfuming of tobacco.
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Production method
Under the catalysis of aluminum trichloride, we can use benzene for reaction with acetyl chloride, acetic anhydride or acetic acid to obtain acetophenone. In addition, in the catalytic oxidation of ethylbenzene to styrene, acetophenone is generated as the byproduct. Industrial grade acetophenone contains main impurities such as α-methylbenzyl alcohol, phenols, acids, and water. The industrial grade product and be refined through drying with calcium chloride and sulfuric acid and further vacuum distillation after the drying. Alternatively, it can also be subject to fractional crystallization refinement from the molten state in the condition of avoiding light and moisture. We can also use pentane for crystallization and refinement in low temperature. Fixed material consumption: benzoic acid: 1130kg/t, acetic acid 555kg/t.
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Description
Acetophenone is the simplest aromatic ketone and is a clear liquid/crystal and very slightly soluble in water with a sweet pungent taste and odour resembling oranges. It is used as a polymerisation catalyst for the manufacture of olefins. Acetophenone is used in perfumery as a fragrance ingredient in soaps, detergents, creams, lotions, and perfumes; as a flavouring agent in foods, non-alcoholic beverages, and tobacco; as a specialty solvent for plastics and resins; as a catalyst for the polymerisation of olefins; and as a photosensitiser in organic syntheses. Acetophenone is a raw material for the synthesis of some pharmaceuticals and is also listed as an approved excipient by the U.S. FDA. Acetophenone occurs naturally in many foods such as apple, apricot, banana, and beef. Acetophenone has been detected in ambient air and drinking water; exposure of the general public may occur through the inhalation of contaminated air or the consumption of contaminated water. It is highly flammable and will get easily ignited by heat, sparks, or flames, and the vapours may form explosive mixtures with air.
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Chemical Properties
Acetophenone is a colorless, oily liquid with a sweet, floral odor.It is a naturally occurring component of a large number of foods and essential oils.
Acetophenone can be hydrogenated catalytically to 1-phenylethanol. It is obtained as a by-product in the Hock phenol synthesis and is purified from the high-boiling residue by distillation. The quantities obtained from this source satisfy the present demand.
Acetophenone is used for perfuming detergents and industrial products and is an intermediate in the synthesis of other fragrance materials.
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Chemical Properties
Acetophenone has a characteristic sweet, pungent and strong medicinal odor with a bitter, aromatic cherry branch taste. It is useful in flavors of grape, cherry and tobacco
Occurrence
Reported found in cocoa, beef, raspberry, peas, and concord grape
Uses
Solvent for Resins, Plastics, Cellulose Ethers and Esters, Intermediate for the F&F market.
Uses
Acetophenone is used in perfumery, as aphotosensitizer in organic synthesis, and asa catalyst in olefin polymerization.In perfumery to impart an orange-blossom-like odor; in organic syntheses, especially. as photosensitizer.
Uses
Acetophenone is a reagent used in the production of fragrances and resin polymers.
Definition
ChEBI: A methyl ketone that is acetone in which one of the hydrogens of the methyl group has been replaced by a phenyl group.
Preparation
From benzene and acetylchloride in the presence of aluminum chloride or by catalytic oxidation of ethyl benzene; also prepared by fractional distillation and crystallization from the essential oil of Stirlingia latifolia.
Aroma threshold values
Detection: 170 ppb; Recognition: 2.9 ppm
Taste threshold values
Taste characteristics at 10 ppm: sweet, nutty, benzaldehyde with musty, fruity notes
Synthesis Reference(s)
Canadian Journal of Chemistry, 56, p. 2269, 1978 DOI: 10.1139/v78-373
Chemical and Pharmaceutical Bulletin, 31, p. 4209, 1983 DOI: 10.1248/cpb.31.4209
General Description
A colorless liquid with a sweet pungent taste and odor resembling the odor of oranges. Melting point 20.5°C (68.9°F); freezes under cool conditions. Slightly soluble in water and denser than water. Hence sinks in water. Vapor heavier than air. Flash point 180°F. A mild irritant to skin and eyes. Vapors can be narcotic in high concentrations. Used as a flavoring, solvent, and polymerization catalyst.
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Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
Acetophenone reacts with many acids and bases liberating heat and flammable gases (e.g., H2). Reacts with many oxidizing agents. Reacts with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. The amount of heat in these reactions may be sufficient to start a fire in the unreacted portion. Incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides.
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Health Hazard
Acetophenone is an irritant, mutagen, and amildly toxic compound. In rabbits 0.77 mgproduced severe eye irritation, but the actionon skin was mild. In mice, subcutaneousadministration of this compound producedsleep; a dose of 330 mg/kg was lethal.
LD50 value, intraperitoneal (mice): 200mg/kg
No symptoms of severe toxicity, nor its carcinogenicityin humans, has been reported..
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Fire Hazard
Combustible liquid; flash point (closed cup) 82°C (180°F); vapor pressure 1 torr at 37°C (98.6°F); vapor density 4.1 (air = 1); autoignition temperature 570°C (1058°F); fire-extinguishing agent: dry chemical, foam, or CO2; water may cause frothing, but it can be used to flush and dilute the spill. Its reaction with strong oxidizers may be violent.
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Safety Profile
Poison by intraperitoneal and subcutaneous routesModerately toxic by ingestion. A skin and severe eye irritant. Mutation data reported. Narcotic in high concentration. A hypnotic. Flammable liquid. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes. See also IGTONES
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Potential Exposure
Acetophenone is used as a solvent and in perfume manufacture to impact a pleasant jasmine or orange-blossom odor. It is used as a catalyst in olefin polymerization and as a flavorant in tobacco. It is also used in the synthesis of pharmaceuticals
Carcinogenicity
No carcinogenicity studies were identified for acetophenone. The U.S. EPA has classified acetophenone as a Category D, not classifiable as to human carcinogenicity.
Environmental Fate
It is unclear what mechanism is responsible for the central nervous system depression observed following high doses of acetophenone. In vitro evaluations have demonstrated that acetophenone suppresses voltage-gated ion channels in olfactory receptor cells and retinal neurons; however, it is unclear if this is related to any of the observed toxicity in animal studies.
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Metabolism
At one time, acetophenone was used as a hypnotic. Its conversion to benzoic acid and methylphenylcarbinol in dogs and rabbits was observed by a number of early workers. Small amounts are also excreted as mandelic acid. In the rabbit about half the dose is excreted as methylphenylcarbinyl glucuronide and about 20 % as hippuric acid. It is probable that the ketone is first asymmetrically reduced to the carbinol, which is the precursor of benzoic and mandelic acids.
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Shipping
UN1993 Flammable liquids, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, Technical Name Required.
Purification Methods
Dry it by fractional distillation or by standing with anhydrous CaSO4 or CaCl2 for several days, followed by fractional distillation under reduced pressure (from P2O5, optional), and careful, slow and repeated partial crystallisations from the liquid at 0o excluding light and moisture. It can also be crystallised at low temperatures from isopentane. Distillation can be followed by purification using gas-liquid chromatography [Earls & Jones J Chem Soc, Faraday Trans 1 71 2186 1975.] [Beilstein 7 H 271, 7 IV 619.] § A commercial polystyrene supported version is available — scavenger resin (for diol substrates).
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Toxicity evaluation
The production and use of acetophenone as a specialty solvent and fragrance and flavor additive may result in environmental releases to the air, water, and soil. Acetophenone is slightly soluble in water and freely soluble in alcohol, chloroform, fatty oils, and glycerol. The vapor pressure at 25 °C is 0.4 mmHg, the Henry’s law constant is estimated to be 1.04×105 atmm3 mol-1, and the octanol/water partition coefficient (log Kow) is 1.58.
If released to the soil, acetophenone is expected to have high mobility, with volatilization from moist soils. If released to the water, volatilization is anticipated from the surface and acetophenone is not anticipated to adsorb to sediment. The potential for bioconcentration in aquatic organisms is predicted to be low. If released to the atmosphere, the half-life is anticipated to be 6 days, with degradation occurring by reaction with photochemically produced hydroxyl radicals.
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Incompatibilities
May form explosive mixture with air. See flash point, above. Reacts violently with strong oxidizers, many acids, bases, amines, amides, and inorganic hydroxides; alkali metals; hydrides, and nitrides. Reacts with reducing agents; alkali metals; hydrides, nitrides. Contact with all preceding materials release heat and flammable gases, including hydrogen; the heat may be sufficient enough to result in fire. Incompatible with aldehydes, aliphatic amines, alkanolamines, cyanides, isocyanates, organic acids, peroxides; perchloric acid. May attack plastics, and some rubbers and coatings
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Waste Disposal
Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Incineration, preferably with a flammable solvent
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