Benzophenone is the organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. It is a white solid that is soluble in organic solvents. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone.
|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||g·mol−1 182.222|
|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. Alkanes + tetrachloromethane: better with increasing tetrachloromethane content
|Main hazards||Harmful (XN)|
|Safety data sheet||External MSDS by JT Baker|
|Flash point||110 °C (230 °F; 383 K)|
Except where otherwise noted, data are 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.
Benzophenone is used as an additive in flavorings or perfumes for "sweet-woody-geranium-like notes."
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.
Another route of synthesis is through a palladium(II)/oxometalate catalyst. This converts an alcohol to a ketone with two groups on each side.
Another, less well-known reaction to produce benzophenone is the pyrolysis of anhydrous calcium benzoate.
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 anionEdit
- 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 and analoguesEdit
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). Its use in sunscreen has been known to cause coral bleaching via algae blooms, as it washes into the ocean from human use.
The high-strength polymer PEEK is prepared from derivatives of benzophenone.
It is considered as "essentially nontoxic." Benzophenone is however banned as a food additive by the US Food and Drug Administration, despite the FDA's continuing stance that this chemical does not pose a risk to public health under the conditions of its intended use. 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.
- "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 723–724, 726. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
- Merck Index (11th ed.). p. 1108.
- Azizian, Saeid; Haydarpour, Afshin (November 2003). "Solubility of Benzophenone in Binary Alkane + Carbon Tetrachloride Solvent Mixtures". Journal of Chemical & Engineering Data. 48 (6): 1476–1478. doi:10.1021/je0340497.
- 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. Bibcode:2010JCIS..351..556C. doi:10.1016/j.jcis.2010.07.070. PMID 20728089.
- Dornath, Paul John (2010). "Analysis of Chemical Leaching from Common Consumer Plastic Bottles Under High Stress Conditions" (PDF). p. 32. Archived from the original (PDF) on 26 February 2015. 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.
- Arctander, Steffen. Perfume And Flavor Chemicals: (Aroma Chemicals).
- Siegel, Hardo; Eggersdorfer, Manfred, "Ketones", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a15_077
- Marvel, C. S.; Sperry, W. M. (1941). "Benzophenone". Organic Syntheses.; Collective Volume, 1, p. 95
- Dornan, L.; Muldoon, M. (2015). "A highly efficient palladium(II)/polyoxometalate catalyst system for aerobic oxidation of alcohols". Catalysis Science & Technology. 5 (3): 1428–1432. doi:10.1039/c4cy01632g.
- Lee, C. C. (1953). "The Mechanism of the Ketonic Pyrolysis of Calcium Carboxylates". The Journal of Organic Chemistry. 18 (9): 1079–1086. doi:10.1021/jo50015a003.
- 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.
- Williams, D. B. G.; Lawton, M. (2010). "Drying of Organic Solvents: Quantitative Evaluation of the Efficiency of Several Desiccants". The Journal of Organic Chemistry. 75 (24): 8351–4. doi:10.1021/jo101589h. PMID 20945830.
- Armarego, W. L. F.; Chai, C. (2003). Purification of laboratory chemicals. Oxford: Butterworth-Heinemann. ISBN 978-0-7506-7571-0.
- Harwood, L. M.; Moody, C. J.; Percy, J. M. (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.
- Downs, C. A.; Kramarsky-Winter, E.; Segal, R.; Fauth, J.; Knutson, S.; Bronstein, O.; Ciner, F. R.; Jeger, R.; Lichtenfeld, Y.; Woodley, C. M.; Pennington, P.; Cadenas, K.; Kushmaro, A.; Loya, Y. (2015). "Toxicopathological Effects of the Sunscreen UV Filter, Oxybenzone (Benzophenone-3), on Coral Planulae and Cultured Primary Cells and Its Environmental Contamination in Hawaii and the U.S. Virgin Islands". Arch. Environ. Contam. Toxicol.
- "FDA Bans Use of 7 Synthetic Food Additives After Environmental Groups Sue". NPR.org. Retrieved 2018-10-09.
- 83 FR 50490
- Consuelo Cuquerella, M.; Lhiaubet-Vallet, V.; Cadet, J.; Miranda, M. A. (2012). "Benzophenone Photosensitized DNA Damage". Acc. Chem. Res. 45 (9): 1558–1570. doi:10.1021/ar300054e. PMID 22698517.
- Doug Brunk (2014-03-14). "Benzophenones named 2014 Contact Allergen of the Year : Dermatology News". Skinandallergynews.com. Retrieved 2016-06-16.[permanent dead link]
- Mikamo, Eriko; Harada, Shingo; Nishikawa, Jun-Ichi; Nishihara, Tsutomu (2003). "Endocrine disruptors induce cytochrome P450 by affecting transcriptional regulation via pregnane X receptor". Toxicology and Applied Pharmacology. 193 (1): 66–72. doi:10.1016/j.taap.2003.08.001. PMID 14613717.