METHYL PHENYL KETONE
Acetophenone
CAS: 98-86-2
Molecular Formula: C8H8O
METHYL PHENYL KETONE - Names and Identifiers
| Name | Acetophenone |
| Synonyms | Acetofenon Acetophenon Acetophenone acetyl-benzen usafek-496[qr] acetophenon[qr] 1-Phenylethanone alpha-Acetophenone 1-Phenyl-1-ethanone METHYL PHENYL KETONE Methyl phenyl ketone ACETOPHENONE extrapure AR |
| CAS | 98-86-2 |
| EINECS | 202-708-7 |
| InChI | InChI=1/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 |
| InChIKey | KWOLFJPFCHCOCG-UHFFFAOYSA-N |
METHYL PHENYL KETONE - Physico-chemical Properties
| Molecular Formula | C8H8O |
| Molar Mass | 120.15 |
| Density | 1.03 g/mL at 25 °C (lit.) |
| Melting Point | 19-20 °C (lit.) |
| Boling Point | 202 °C (lit.) |
| Flash Point | 180°F |
| JECFA Number | 806 |
| Water Solubility | 5.5 g/L (20 ºC) |
| Solubility | 6.1g/l |
| Vapor Presure | 0.45 mm Hg ( 25 °C) |
| Vapor Density | 4.1 (vs air) |
| Appearance | White crystal |
| Color | Clear colorless to light yellow |
| Odor | Pungent, floral odor |
| Exposure Limit | No exposure limits are set. The health hazardfrom exposure to this compound should below, due to its low vapor pressure and lowtoxicity. |
| Merck | 14,73 |
| BRN | 605842 |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Incompatible with strong oxidizing agents, strong bases, strong reducing agents. Combustible. |
| Sensitive | Easily absorbing moisture |
| Explosive Limit | 1.4-5.2%(V) |
| Refractive Index | n20/D 1.534(lit.) |
| MDL | MFCD00008724 |
| Physical and Chemical Properties | Colorless crystals or pale yellow oily liquid. There is an aroma like Hawthorn. Density of 1.0281, melting point of 19.7 deg C, boiling point of 202.3 deg C. Slightly soluble in water, soluble in many organic solvents. Can be volatilized with steam. Oxidation of benzoic acid and carbon dioxide. Reduction to ethylbenzene or ethylcyclohexane or 1-phenylethanol. |
| Use | Used as a raw material for the manufacture of spices and medicines, also used as plasticizers and solvents; Also used in the preparation of spices |
METHYL PHENYL KETONE - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36 - Irritating to the eyes R63 - Possible risk of harm to the unborn child R43 - May cause sensitization by skin contact 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 R39/23/24/25 - R11 - Highly Flammable R67 - Vapors may cause drowsiness and dizziness R40 - Limited evidence of a carcinogenic effect |
| Safety Description | 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. |
| UN IDs | UN 1593 6.1/PG 3 |
| WGK Germany | 1 |
| RTECS | AM5250000 |
| FLUKA BRAND F CODES | 8 |
| TSCA | Yes |
| HS Code | 29143900 |
| Packing Group | III |
| Toxicity | LD50 orally in rats: 0.90 g/kg (Smyth, Carpenter) |
METHYL PHENYL KETONE - Reference
| Reference Show more | 1. [IF=7.514] Lijuan Ma et al."Characterization of the key aroma-active compounds in high-grade Dianhong tea using GC-MS and GC-O combined with sensory-directed flavor analysis."Food Chem. 2022 Jun;378:132058 |
METHYL PHENYL KETONE - Nature
Open Data Verified Data
a colorless liquid with a high refractive index has a pleasant aromatic odor. Melting point 20.5 °c. Boiling point 202.6 ℃,79 ℃(1. 33kPa), relative density 1.028 (20 ℃). Refractive index 5372. Slightly soluble in water, soluble in alcohol, ether, chloroform, fatty oil and glycerol, soluble in concentrated sulfuric acid when Orange.
Last Update：2024-01-02 23:10:35
METHYL PHENYL KETONE - Preparation Method
Open Data Verified Data
It is prepared by the reaction of benzene with acetyl chloride, acetic anhydride or acetic acid under the catalysis of aluminum trichloride.
- acylation of benzene with acetic anhydride the yield of this method can reach 85%.
- reaction method of benzene and acetyl chloride
- benzoic acid method
- multi-phase oxidation of ethylbenzene
Last Update：2022-01-01 10:42:31
METHYL PHENYL KETONE - Introduction
It has a high refractive index and a pleasant aromatic smell. It is flaky crystal at low temperature. Sensitive to light. Soluble in alcohol, ether, chloroform, fatty oil and glycerin, slightly soluble in water. It is orange when dissolved in concentrated sulfuric acid. Low toxicity, median lethal dose (rat, oral) 0.90 g/kg. There's a pungent smell. Solubility in water: 5.5g/L (20°C).
Last Update：2022-10-16 17:30:28
METHYL PHENYL KETONE - Use
Open Data Verified Data
for the synthesis of phenylglycolic acid, a phenyl indole, isobutylphenylpropionic acid, also used as a plasticizer for plastics.
Last Update：2022-01-01 10:42:30
METHYL PHENYL KETONE - Safety
Open Data Verified Data
- This product vapor has anesthetic effect, can cause dermatitis. The oral LD50 of rats was 3000mg/kg. Galvanized iron drum, net weight: 200kg soil lkg.
- the product should be placed in a cool and dry place during transportation and storage, and should not be close to the fire source or heat source.
Last Update：2022-01-01 10:42:31
METHYL PHENYL KETONE - Reference Information
| FEMA | 2009 | ACETOPHENONE |
| relative polarity | 4.4 |
| LogP | 1.65 at 20℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | acetophenone, also known as acetophenone, boiling point (℃):202.3, relative density (water = 1):1.03(20 °c), relative vapor density (Air = 1):4.14, is the simplest aromatic ketone in which the aromatic nucleus (benzene ring) is directly linked to the carbonyl group. It is present in the essential oils of some plants in a free state. The pure product is a colorless crystal. Commercial goods are mostly light yellow oily liquid. There is an aroma like Hawthorn. Slightly soluble in water, soluble in a variety of organic solvents, can be volatilized with steam. Acetophenone molecular structure: the methyl C atom is bonded to the sp3 hybrid orbital, and the benzene ring and the carbonyl C atom are bonded to the sp2 hybrid orbital. Acetophenone can occur carbonyl addition reaction, alpha active hydrogen reaction, but also on the benzene ring electrophilic substitution reaction, mainly to produce meta-product. Acetophenone can be prepared by the reaction of benzene with acetyl chloride, acetic anhydride or acetic acid under the catalysis of aluminum trichloride. In addition, when ethylbenzene is catalytically oxidized to styrene, acetophenone is a by-product. Acetophenone is mainly used as a raw material for pharmaceutical and other organic synthesis, and is also used for the preparation of spices. For the preparation of soap and cigarettes, can also be used as cellulose ether, cellulose ester and resin solvent and plastic plasticizer, hypnotic. Acetophenone is now mostly obtained as a by-product of the oxidation of cumene to phenol and acetone, and it can also be prepared by acetylation of benzene with acetyl chloride. |
| preparation of acetophenone | [instrument and medicine] medicine: Acetic anhydride benzhydric magnesium sulfate hydrochloric acid aluminum chloride sodium hydroxide instrument: round-bottom flask condenser dropping funnel distillation device drying tube stirring device [Operation Procedure] a 10ml constant pressure dropping funnel, a mechanical stirring device and a reflux condenser (the upper end is connected to the hydrogen chloride gas absorption device through a calcium chloride drying tube) A 0.18 ml three-necked flask was quickly charged with 13g(0.097mol) of powdered anhydrous aluminum trichloride and 16ml (about 14g, mol) of anhydrous benzene. Add 4ml (about 4.3g,0.04mol) of acetic anhydride slowly and Dropwise from the dropping funnel to the three-necked flask with stirring (add a few drops first and continue the dropwise addition after the reaction has taken place), it is advisable to control the dropping acceleration of acetic anhydride so that the three-necked flask is slightly heated. After the addition was complete (about 10min), the reaction was stirred at reflux in a boiling water bath until no more hydrogen chloride gas had evolved. The reaction mixture was cooled to room temperature and poured into a beaker of 18ml of concentrated hydrochloric acid and 30g of crushed ice (in a fume hood) with stirring. If solid insolubles remained, an appropriate amount of concentrated hydrochloric acid was added to completely dissolve. Transfer the mixture to a separatory funnel and separate the organic layer (which layer? The aqueous layer was extracted twice with benzene (8ml each). The organic layers were combined, washed with 15ml of 10% sodium hydroxide, 15ml of water, and dried over anhydrous magnesium sulfate. First in the water bath distillation recovery of benzene, and then in the asbestos net heating to remove residual benzene, slightly cold after the air condenser tube (why?) The 195-202 ° C. Fraction was collected by distillation, and the yield was about 4.1g (85% yield). Pure acetophenone is a colorless transparent oily liquid. [Note] 1, add acetophenone and acetic anhydride mixture of time to 10min is appropriate, drop too fast temperature is not easy to control. 2, the quality of anhydrous aluminum chloride is the key to the success or failure of this experiment, with white powder to open the cover a lot of smoke, no caking phenomenon is good. If most of it turns yellow, it indicates that it has been hydrolyzed and is not useful. 3,AlCl3 to be ground, the speed should be fast. 4. When dilute HCl was added, it started to drop slowly, then gradually; The amount of dilute HCl(1:1, prepared) was about 140ml. 5, absorption device: about 20% sodium hydroxide solution, self-made, 200mL, with special attention to prevent back suction. 6, benzene to analytical purity is better, it is best to use the wire drying for more than 24 hours. 7, a small amount of water in the crude product, distilled off with benzene in the form of azeotrope during distillation, the azeotropic point of 69.4 deg C, this is one of the methods of drying liquid compounds. |
| Friedel-Craffs characteristics of acetophenone prepared by acylation reaction | 1, the amount of catalyst used in the acylation reaction is much larger than that of the catalyst used in the alkylation reaction, and the generated acetophenone forms a complex with an equivalent amount of aluminum chloride, at the same time, the by-product acetic acid formed in the reaction can also form a salt with the equivalent of aluminum chloride, so in the acylation reaction, one molecule of anhydride consumes more than two molecules of aluminum chloride 2, the acetophenone/aluminum chloride complex formed in the reaction is stable in anhydrous medium. Only when the reaction mixture is hydrolyzed, the complex is destroyed and acetophenone is precipitated, no longer participate in the reaction, therefore, the amount of aluminum chloride is in the formation of complex, there are remaining as a catalyst for acylation reaction 3, because aluminum chloride can form complexes with substances containing carboxyl groups, therefore, the raw material acetic anhydride can also form a molecular complex with aluminum chloride, and no longer participate in the reaction, that is, acetic anhydride cannot be quantitatively converted into acetophenone; In addition, in the reaction, when the amount of aluminum chloride is large, can make the acetate into acetyl chloride, as acylation reagent, participate in reaction 4, reaction system, benzene dosage is also large In large excess, acetyl is the benchmark reagent for yield since benzene serves not only as a reaction reagent but also as a solvent in the reaction. 5, the characteristics of the acylation reaction: the product is pure, high yield (due to the acyl group does not occur isomerization, also does not occur multiple substitution) |
| Use | when used as a solvent, it has the characteristics of high boiling point, stability and pleasant smell. The dissolving ability is similar to that of cyclohexanone, and can dissolve nitrocellulose; Cellulose acetate; Vinyl resin; Coumarone resin; Alkyd resin; Glycerol alkyd resin, etc. Often used in combination with ethanol; Ketones; Esters and other solvents. When used as spices, is the Hawthorn; Mimosa; Clove flavor blending raw materials, and widely used in soap flavor and tobacco flavor. For the synthesis of phenylglycolic acid; Α-phenylindole; Isobutylphenylpropionic acid, etc., also used as plasticizers for plastics. Naturally occurring: found in milk, cheese, cocoa, raspberry, pea, Sri Lanka cinnamon oil. Sensory characteristics: with a flavor of almond similar to benzaldehyde, diluted with sweet nuts, fruit taste. Application recommendations: for the preparation of cherry, nuts, tomatoes, strawberries, apricot and other food flavors, can also be used in tobacco flavor. Suggested dosage: the concentration in the final perfumed food is about 0.6~20mg/kg. Safety Management: acetophenone FEMA number 2009,FDA number 172.515,CoE number 138. China GB 2760-1996 is approved for the permitted use of food flavors. GB 2760-1996 provides for the permitted use of flavorants. Mainly used for the preparation of grapes, cherries and other fruits and tobacco flavor. used as solvent, extraction agent, also used in pharmaceutical industry used as solvent, olefin polymerization catalyst, used in the manufacture of spices, etc. can be used together with anisaldehyde and coumarin for Hawthorn flower, sunflower, new Humulus, lavender, vanilla, clove, shamed flower, acacia and other type of essence. Because of its low cost, it is often used in small amounts (<1%) for perfuming soap, detergents and industrial products. Can also be used in trace amounts of food flavor, such as almond, cherry, walnut, vanilla bean, black bean flavor. Tobacco flavoring is also available. when used as a solvent, it has the characteristics of high boiling point, stability and pleasant smell. The dissolving ability is similar to that of cyclohexanone, and can dissolve nitrocellulose, cellulose acetate, vinyl resin, coumarone resin, alkyd resin, glycerol alkyd resin, etc. It is often used in combination with ethanol, Ketones, Esters, and other solvents. When used as spices, it is the blending raw material of Hawthorn, Mimosa, clove and other essences, and is widely used in soap essence and tobacco essence. For the synthesis of phenylglycolic acid, α-phenylindole, isobutylphenylpropionic acid, also used as plasticizers for plastics. It is used as a raw material for producing perfume and medicine, and is also used as a plasticizer and a solvent solvent. Extractant. Catalysts for the polymerization of olefins. Plasticizers. Photosensitizer. Organic Synthesis. |
| content analysis | accurately weigh about 1g of the sample and follow "determination of aldehydes and ketones" (OT-7) method 1 determination. The heating time was 1H. The equivalence factor (e) in the calculation is taken as 60.08. |
| toxicity | LD50 3g/kg (rat, oral);ADI 1 mg/kg(CE). |
| usage limit | FEMA(mg/kg): Soft drink 0.98; Cold drink 2.8; Baked food 5.6; Candy 3.6; pudding 7.0; Gum 0.6~20. Moderate limits (FDA § 172.515,2000). |
| production method | acetophenone can be obtained by reacting benzene with acetyl chloride, acetic anhydride or acetic acid under the catalysis of aluminum trichloride. In addition, the catalytic oxidation of ethylbenzene to styrene, the production of acetophenone. The main impurities of industrial grade acetophenone are α-methyl benzyl alcohol, phenol, acidic substances, water and the like. After being refined, it is dried with calcium chloride or sulfuric acid and fractionated under reduced pressure. Or in the case of avoiding light and moisture, from the molten state step crystallization purification, can also be used in the low temperature crystallization of pentane. Raw material consumption quota: benzoic acid 1130kg/t, acetic acid 555kg/t. obtained by co-distillation of calcium benzoate and calcium acetate. Benzene and acetyl chloride in the presence of aluminum chloride reaction. Derived from the oxidation of ethylbenzene. |
| category | flammable liquid |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 815 mg/kg; Oral-mouse LD50: 740 mg/kg |
| stimulation data | Skin-rabbit 515 mg mild; Eye-rabbit 0.75 mg severe |
| flammability hazard characteristics | flammable in open flame, high temperature, strong oxidant; heat decomposition releases stimulus smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | foam, carbon dioxide, dry powder, 1211 |
| Occupational Standard | TWA 15 mg/m3; Tel 30 mg/m3 |
| spontaneous combustion temperature | 570°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:53
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