Acetophenone

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Acetophenone
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Names
Preferred IUPAC name
1-Phenylethanone[1]
Other names
Acetophenone
Phenylethanone
Methyl phenyl ketone
Identifiers
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3D model (JSmol)
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Abbreviations ACP
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UN number 1993
  • InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 checkY
    Key: KWOLFJPFCHCOCG-UHFFFAOYSA-N checkY
  • 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
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NFPA 704 four-colored diamondHealth 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).
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Template:Chembox Footer/trackingTemplate:Short description

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]

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:

Page Module:Chem2/styles.css has no content.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 Page Module:Chem2/styles.css has no content.[(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] More common as a fragrance is the closely related 4-methylacetophenone.[5]

Laboratory reagent

In instructional laboratories,[6] acetophenone is converted to styrene in a two-step process that illustrates the reduction of carbonyls using sodium borohydride and the dehydration of alcohols:

Page Module:Chem2/styles.css has no content.4 C6H5C(O)CH3 + NaBH4 + 4 H2O → 4 C6H5CH(OH)CH3 + NaOH + B(OH)3
Page Module:Chem2/styles.css has no content.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]

Page Module:Chem2/styles.css has no content.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.[7][8]

Natural occurrence

Acetophenone occurs naturally in many foods including apple, cheese,[9] apricot, banana,[10] beef, and cauliflower.

Pharmacology

In the late 19th and early 20th centuries, acetophenone was used in medicine.[11] It was marketed as a hypnotic and anticonvulsant under brand name Hypnone. The typical dosage was 0.12 to 0.3 milliliters.[12] It was considered to have superior sedative effects to both paraldehyde and chloral hydrate.[13] In humans, acetophenone is metabolized to benzoic acid, carbonic acid, and acetone.[14] Hippuric acid occurs as an indirect metabolite and its quantity in urine may be used to confirm acetophenone exposure,[15] although other substances, like toluene, also induce hippuric acid in urine.[16]

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.

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ a b c d e f Script error: No such module "Template wrapper".
  3. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content."Inactive Ingredient Search for Approved Drug Products". Archived from the original on 2013-05-04.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Panten, Johannes; Surburg, Horst (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–45. doi:10.1002/14356007.t11_t02. ISBN 978-3-527-30673-2.
  6. ^ Page Module:Citation/CS1/styles.css has no content.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.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Sittig, Marshall (1988). Pharmaceutical Manufacturing Encyclopedia. pp. 39, 177. ISBN 978-0-8155-1144-1.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Gadamasetti, Kumar; Tamim Braish (2007). Process Chemistry in the Pharmaceutical Industry, Volume 2. Taylor & Francis. pp. 142–145. ISBN 978-0-8493-9051-7.
  9. ^ Page Module:Citation/CS1/styles.css has no content.Engels, W.J.M.; Dekker, R.; De Jong, C.; Neeter, R.; Visser, S. (1997). "A comparative study of volatile compounds in the water-soluble fraction of various types of ripened cheese". International Dairy Journal. 7 (4): 255–263. Bibcode:1997IntDJ...7..255E. doi:10.1016/S0958-6946(97)00003-4.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Pino, Jorge A.; Febles, Yanet (2013). "Odour-active compounds in banana fruit cv. Giant Cavendish". Food Chemistry. 141 (2): 795–801. doi:10.1016/j.foodchem.2013.03.064. PMID 23790849.
  11. ^ Page Module:Citation/CS1/styles.css has no content.Budavari, Susan, ed. (1996). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.). Merck. ISBN 0911910123.
  12. ^ Page Module:Citation/CS1/styles.css has no content.Bartholow, Roberts (1908). A Practical Treatise on Materia Medica and Therapeutics. Appleton & Co.
  13. ^ Page Module:Citation/CS1/styles.css has no content.Norman, Conolly (1887). "Cases illustrating the sedative effects of aceto-phenone". Journal of Mental Science. 32: 519. doi:10.1192/bjp.32.140.519.
  14. ^ Page Module:Citation/CS1/styles.css has no content."Hypnone – The new hypnotic". Journal of the American Medical Association. 5 (23): 632. 1885. doi:10.1001/jama.1885.02391220016006.
  15. ^ CID 7410 from PubChemTemplate:EditAtWikidataTemplate:WikidataCheck
  16. ^ Page Module:Citation/CS1/styles.css has no content."The Netherlands Center for Occupational Diseases (NCvB): toluene (Dutch)" (PDF). beroepsziekten.nl. Retrieved 19 April 2018.

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Wikisource has the text of the 1911 Encyclopædia Britannica article "Acetophenone".

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