Acetophenone

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Acetophenone
Acetophenone-2D-skeletal.svg
Ball-and-stick model of the acetophenone molecule Acetophenone-from-xtal-Mercury-3D-bs.png
Ball-and-stick model of the acetophenone molecule
Space-filling model of the acetophenone molecule Acetophenone-from-xtal-Mercury-3D-sf.png
Space-filling model of the acetophenone molecule
Atsetofenon.jpg
Names
Preferred IUPAC name
1-Phenylethan-1-one [1]
Other names
Acetophenone
Phenylethanone
Methyl phenyl ketone
Identifiers
3D model (JSmol)
AbbreviationsACP
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.462 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-708-7
KEGG
PubChem CID
RTECS number
  • AM5250000
UNII
UN number 1993
  • InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 Yes check.svgY
    Key: KWOLFJPFCHCOCG-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3
    Key: KWOLFJPFCHCOCG-UHFFFAOYAT
  • O=C(c1ccccc1)C
  • CC(=O)c1ccccc1
Properties
C8H8O
Molar mass 120.151 g·mol−1
Density 1.028 g/cm3
Melting point 19–20 °C (66–68 °F; 292–293 K)
Boiling point 202 °C (396 °F; 475 K)
5.5 g/L at 25 °C
12.2 g/L at 80 °C
-72.05·10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H319
P264, P270, P280, P301+P312, P305+P351+P338, P330, P337+P313, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Flash point 77 °C (171 °F; 350 K)
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances. [2]

Contents

Production

Acetophenone is formed as a byproduct of the cumene process, the industrial route for the synthesis of phenol and acetone. In the Hock rearrangement of isopropylbenzene hydroperoxide, migration of a methyl group rather than the phenyl group gives acetophenone and methanol as a result of an alternate rearrangement of the intermediate:

C6H5C(CH3)2O2H → C6H5C(O)CH3 + CH3OH

The cumene process is conducted on such a large scale that even the small amount of acetophenone by-product can be recovered in commercially useful quantities. [2]

Acetophenone is also generated from ethylbenzene hydroperoxide. Ethylbenzene hydroperoxide is primarily converted to 1-phenylethanol (α-methylbenzyl alcohol) in the process with a small amount of by-product acetophenone. Acetophenone is recovered or hydrogenated to 1-phenylethanol which is then dehydrated to produce styrene. [2]

Uses

Precursor to resins

Commercially significant resins are produced from treatment of acetophenone with formaldehyde and a base. The resulting copolymers are conventionally described with the formula [(C6H5COCH)x(CH2)x]n, resulting from aldol condensation. These substances are components of coatings and inks. Modified acetophenone-formaldehyde resins are produced by the hydrogenation of the aforementioned ketone-containing resins. The resulting polyol can be further crosslinked with diisocyanates. [2] The modified resins are found in coatings, inks and adhesives.

Niche uses

Acetophenone is an ingredient in fragrances that resemble almond, cherry, honeysuckle, jasmine, and strawberry. It is used in chewing gum. [3] It is also listed as an approved excipient by the U.S. FDA. [4]

Laboratory reagent

In instructional laboratories, [5] acetophenone is converted to styrene in a two-step process that illustrates the reduction of carbonyls using sodium borohydride and the dehydration of alcohols:

4 C6H5C(O)CH3 + NaBH4 + 4 H2O → 4 C6H5CH(OH)CH3 + NaOH + B(OH)3
C6H5CH(OH)CH3 → C6H5CH=CH2 + H2O

A similar two-step process is used industrially, but reduction step is performed by hydrogenation over a copper chromite catalyst: [2]

C6H5C(O)CH3 + H2 → C6H5CH(OH)CH3

Being prochiral, acetophenone is also a popular test substrate for asymmetric hydrogenation experiments.

Drugs

Acetophenone is used for the synthesis of many pharmaceuticals. [6] [7]

Natural occurrence

Acetophenone occurs naturally in many foods including apple, cheese, apricot, banana, beef, and cauliflower. It is also a component of castoreum, the exudate from the castor sacs of the mature beaver. [8]

Pharmacology

In the late 19th and early 20th centuries, acetophenone was used in medicine. [9] It was marketed as a hypnotic and anticonvulsant under brand name Hypnone. The typical dosage was 0.12 to 0.3 milliliters. [10] It was considered to have superior sedative effects to both paraldehyde and chloral hydrate. [11] In humans, acetophenone is metabolized to benzoic acid, carbonic acid, and acetone. [12] Hippuric acid occurs as an indirect metabolite and its quantity in urine may be used to confirm acetophenone exposure, [13] although other substances, like toluene, also induce hippuric acid in urine. [14]

Toxicity

The LD50 is 815 mg/kg (oral, rats). [2] Acetophenone is currently listed as a Group D carcinogen indicating that there is no evidence at present that it causes cancer in humans.

Related Research Articles

<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Phenol</span> Organic compound (C6H5OH)

Phenol is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

<span class="mw-page-title-main">Petrochemical</span> Chemical product derived from petroleum

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<span class="mw-page-title-main">Styrene</span> Chemical compound

Styrene is an organic compound with the chemical formula C6H5CH=CH2. Its structure consists of a vinyl group as substituent on benzene. Styrene is a colorless, oily liquid, although aged samples can appear yellowish. The compound evaporates easily and has a sweet smell, although high concentrations have a less pleasant odor. Styrene is the precursor to polystyrene and several copolymers, and is typically made from benzene for this purpose. Approximately 25 million tonnes of styrene were produced in 2010, increasing to around 35 million tonnes by 2018.

<span class="mw-page-title-main">Cumene process</span> Industrial process

The cumene process is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene, the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR), and independently by Heinrich Hock in 1944.

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<span class="mw-page-title-main">Propylene oxide</span> Chemical compound

Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula C3H6O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture.

<span class="mw-page-title-main">Ethylbenzene</span> Hydrocarbon compound; precursor to styrene and polystyrene

Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as a reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.

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Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has a sweet odor reminiscent of benzaldehyde. Over time, samples of cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Millions of tonnes are produced annually, mainly as a precursor to nylon.

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Acetone is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colorless, highly volatile, and flammable liquid with a characteristic pungent odour, very reminiscent of the smell of pear drops.

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Cumene hydroperoxide is the organic compound with the formula C6H5C(CH3)2OOH. An oily liquid, it is classified as an organic hydroperoxide. Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-phenyl-2-propanol.

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References

  1. ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 723. doi:10.1039/9781849733069-00648. ISBN   978-0-85404-182-4. The names acetophenone and benzophenone are retained only for general nomenclature, but no substitution is allowed.
  2. 1 2 3 4 5 6 Siegel, Hardo; Eggersdorfer, Manfred. "Ketones". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077. ISBN   978-3527306732.
  3. ↑ Burdock, George A. (2005), Fenaroli's Handbook of Flavor Ingredients (5th ed.), CRC Press, p. 15, ISBN   0-8493-3034-3, archived from the original on 2014-09-25
  4. ↑ "Inactive Ingredient Search for Approved Drug Products". Archived from the original on 2013-05-04.
  5. ↑ Wilen, Samuel H.; Kremer, Chester B.; Waltcher, Irving (1961). "Polystyrene—A multistep synthesis: For the undergraduate organic chemistry laboratory". J. Chem. Educ. 38 (6): 304–305. Bibcode:1961JChEd..38..304W. doi:10.1021/ed038p304.
  6. ↑ Sittig, Marshall (1988). Pharmaceutical Manufacturing Encyclopedia . pp.  39, 177. ISBN   978-0-8155-1144-1.
  7. ↑ Gadamasetti, Kumar; Tamim Braish (2007). Process Chemistry in the Pharmaceutical Industry, Volume 2. Taylor & Francis. pp. 142–145. ISBN   978-0-8493-9051-7.
  8. ↑ Müller-Schwarze, D.; Houlihan, P. W. (April 1991). "Pheromonal activity of single castoreum constituents in beaver, Castor canadensis". Journal of Chemical Ecology. 17 (4): 715–34. Bibcode:1991JCEco..17..715M. doi:10.1007/BF00994195. PMID   24258917. S2CID   29937875.
  9. ↑ Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN   0911910123
  10. ↑ Bartholow, Roberts (1908). A Practical Treatise on Materia Medica and Therapeutics. Appleton & Co.
  11. ↑ Norman, Conolly (1887). "Cases illustrating the sedative effects of aceto-phenone". Journal of Mental Science. 32: 519. doi:10.1192/bjp.32.140.519.
  12. ↑ "Hypnone – The new hypnotic". Journal of the American Medical Association. 5 (23): 632. 1885. doi:10.1001/jama.1885.02391220016006.
  13. ↑ CID 7410 from PubChem
  14. ↑ "The Netherlands Center for Occupational Diseases (NCvB): toluene (Dutch)" (PDF). beroepsziekten.nl. Retrieved 19 April 2018.
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