m [r2.6.5] robot Adding: es:Benzofenona |
Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: {{cascite}} StdInChI StdInChIKey. |
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| UNII = 701M4TTV9O |
| UNII = 701M4TTV9O |
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| InChIKey = RWCCWEUUXYIKHB-UHFFFAOYAX |
| InChIKey = RWCCWEUUXYIKHB-UHFFFAOYAX |
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| StdInChI = 1S/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H |
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| StdInChIKey = RWCCWEUUXYIKHB-UHFFFAOYSA-N |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID=2991 |
| ChemSpiderID=2991 |
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Revision as of 16:24, 29 November 2010
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| Names | |
|---|---|
| IUPAC name
diphenylmethanone
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| Other names
phenyl ketone; diphenyl ketone; benzoylbenzene
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.003.943 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C13H10O | |
| Molar mass | 182.217 g/mol |
| Appearance | White solid |
| Density | 1.11 g/cm3, solid |
| Melting point | 47.9 °C |
| Boiling point | 305.4 °C |
| Insoluble | |
| Solubility | Benzene, THF, ethanol, propylene glycol |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Harmful (XN) |
| NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Benzophenone is the organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone.
Uses
Benzophenone can be used as a photo initiator in UV-curing applications such as inks, imaging, and clear coatings in the printing industry. Benzophenone prevents ultraviolet (UV) light from damaging scents and colors in products such as perfumes and soaps. It can also be added to the plastic packaging as a UV blocker. Its use allows manufacturers to package the product in clear glass or plastic. Without it, opaque or dark packaging would be required.
Synthesis
Benzophenone can be prepared by the reaction of benzene with carbon tetrachloride followed by hydrolysis of the resulting diphenyldichloromethane,[1] or by Friedel-Crafts acylation of benzene with benzoyl chloride in the presence of a Lewis acid (e.g. aluminium chloride) catalyst. The industrial synthesis relies on the copper-catalyzed oxidation of diphenylmethane with air.[2]
Organic chemistry
Benzophenone is a common photosensitizer in photochemistry. It crosses from the S1 state into the triplet state with nearly 100% yield. The resulting diradical will abstract a hydrogen atom from a suitable hydrogen donor to form a ketyl radical.
Benzophenone radical anion
Sodium reduces benzophenone to the deeply colored radical anion, diphenylketyl:
- Na + Ph2CO → Na+ + Ph2CO−
This ketyl is used in the purification of hydrocarbon solvents, because it reacts with water and oxygen to give colorless non-volatile products:[3]
- Na + H2O → NaOH + 0.5H2
Commercially significant derivatives
Substituted benzophenones such as oxybenzone and dioxybenzone are used in some sunscreens. The use of benzophenone-derivatives which structurally resemble a strong photosensitizer has been strongly criticized (see sunscreen controversy).[4]
p,p'-bis(N,N-dimethylamino)benzophenone or Michler's ketone has dimethylamino substituents at each para position.
The high-strength polymers PEEK, polyetherether ketones, are prepared from derivatives of benzophenone.
See also
References
- ^ Marvel, C. S.; Sperry, W. M. (1941). "Benzophenone". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 1, p. 95. - ^ Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, 2002 by Wiley-VCH, Wienheim. DOI: 10.1002/14356007.a15_077
- ^ W. L. F. Armarego and C. Chai (2003). Purification of laboratory chemicals. Butterworth-Heinemann. ISBN 0750675713.
{{cite book}}: Unknown parameter|city=ignored (|location=suggested) (help) - ^ Knowland, John; McKenzie, Edward A.; McHugh, Peter J.; Cridland, Nigel A. (1993). "Sunlight-induced mutagenicity of a common sunscreen ingredient". FEBS Letters. 324 (3): 309–313. doi:10.1016/0014-5793(93)80141-G. PMID 8405372.
{{cite journal}}: CS1 maint: multiple names: authors list (link)
Notes
- Merck Index, 11th edition, 1108.
Gallery
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A bottle of benzophenone by Lancaster. -
Toluene is refluxed with sodium and benzophenone to produce dry, oxygen-free toluene. -
The mixture is still not blue yet indicating that the reaction is not complete. -
The intense blue coloration due to the benzophenone ketyl radical shows that the toluene is considered free of air and moisture. -
After the toluene has been thoroughly dried by the sodium and benzophenone, it is distilled at atmospheric pressure under a slight positive pressure of nitrogen to prevent contamination by air into the receiving Schlenk flask.
