Phenyl ketone; Diphenyl ketone; Benzoylbenzene; Benzoylphenyl
|Molar mass||182.22 g·mol−1|
|Melting point||48.5 °C (119.3 °F; 321.6 K)|
|Boiling point||305.4 °C (581.7 °F; 578.5 K)|
|Solubility in organic solvents||1 g/ 7.5 mL in ethanol
1 g/ 6 mL in diethyl ether
|SDS||External MSDS by JT Baker|
|Main hazards||Harmful (XN)|
|Flash point||110 °C (230 °F; 383 K)|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
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.
Benzophenone can also be added to plastic packaging as a UV blocker to prevent photo-degradation of the packaging polymers or its contents. Its use allows manufacturers to package the product in clear glass or plastic (such as a PETE water bottle). Without it, opaque or dark packaging would be required.
In biological applications, benzophenones have been used extensively as photophysical probes to identify and map peptide–protein interactions.
A laboratory route involves the reaction of benzene with carbon tetrachloride followed by hydrolysis of the resulting diphenyldichloromethane. It can also be prepared by Friedel-Crafts acylation of benzene with benzoyl chloride in the presence of a Lewis acid (e.g. aluminium chloride) catalyst.
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
Alkali metals reduce benzophenone to the deeply blue colored radical anion, diphenylketyl:
- M + Ph2CO → M+Ph2CO·−
Generally sodium is used as the alkali metal. Although inferior in terms of safety and effectiveness relative to molecular sieves, this ketyl is used in the purification of organic solvents, particularly ethers, because it reacts with water and oxygen to give non-volatile products. The ketyl is soluble in the organic solvent being dried, so it accelerates the reaction of the sodium with water and oxygen. In comparison, sodium is insoluble, and its heterogeneous reaction is much slower. When excess alkali metal is present a second reduction may occur, resulting in a color transformation from deep blue to purple:
- M + M+Ph2CO·− → (M+)2(Ph2CO)2−
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).
The high-strength polymer PEEK is prepared from derivatives of benzophenone.
Benzophenone derivatives are known to be pharmacologically active. From a molecular chemistry point of view interaction of benzophenone with B-DNA has been demonstrated experimentally. The interaction with DNA and the successive photo-induced energy transfer is at the base of the benzophenone activity as a DNA photosensitizers and may explain part of its therapeutic potentialities.
Benzophenone used in practical synthesis list of following drugs:
- Merck Index, 11th edition, 1108
- Carroll, G.T.; Turro, N.J.; Koberstein, J.T. (2010). "Patterning dewetting in thin polymer films by spatially directed photocrosslinking". Journal of Colloid and Interface Science 351 (2): 556–560. doi:10.1016/j.jcis.2010.07.070.
- Dornath, Paul John (2010). "Analysis of Chemical Leaching from Common Consumer Plastic Bottles Under High Stress Conditions" (PDF). p. 32. Retrieved 26 February 2015.
- Dorman, Gyorgy; Prestwich, Glenn D. (1 May 1994). "Benzophenone Photophores in Biochemistry". Biochemistry 33 (19): 5661–5673. doi:10.1021/bi00185a001.
- 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
- Marvel, C. S.; Sperry, W. M. (1941). "Benzophenone". Org. Synth.; Coll. Vol. 1, p. 95
- Connelly, Neil; Geiger, William (March 28, 1996). "Chemical Redox Agents for Organometallic Chemistry". Chemical Reviews 96 (2): 877–910. doi:10.1021/cr940053x. PMID 11848774. Retrieved May 14, 2014.
- Williams, D. B. G., Lawton, M., "Drying of Organic Solvents: Quantitative Evaluation of the Efficiency of Several Desiccants", The Journal of Organic Chemistry 2010, vol. 75, 8351. doi: 10.1021/jo101589h
- W. L. F. Armarego and C. Chai (2003). Purification of laboratory chemicals. Oxford: Butterworth-Heinemann. ISBN 0-7506-7571-3.
- L. M. Harwood, C. J. Moody and J. M. Percy (1999). Experimental Organic Chemistry: Standard and Microscale. Oxford: Blackwell Science. ISBN 978-0-632-04819-9.
- 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.
- Consuelo Cuquerella, M.; Lhiaubet-Vallet, V.; Cadet, J.; Miranda, M. A. (2012). "Benzophenone Photosensitized DNA Damage". Acc. Chem. Res. 45: 1558–1570. doi:10.1021/ar300054e.
Toluene is refluxed with sodium and benzophenone to produce dry, oxygen-free toluene.