|Preferred IUPAC name
|Systematic IUPAC name
3D model (JSmol)
|Molar mass||106.12 g·mol−1|
|Appearance||colorless or yellowish liquid
|Density||1.044 g/mL, liquid|
|Melting point||−57.12 °C (−70.82 °F; 216.03 K)|
|Boiling point||178.1 °C (352.6 °F; 451.2 K)|
|0.3 g/100 mL (20 °C)|
|Solubility||soluble in liquid ammonia|
|Solubility||.695 g/100 mL|
Refractive index (nD)
|Viscosity||1.321 cP (25 °C)|
Std enthalpy of
Std enthalpy of
|Safety data sheet||J. T. Baker|
|S-phrases (outdated)||(S2), S24|
|Flash point||64 °C (147 °F; 337 K)|
|192 °C (378 °F; 465 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|1300 mg/kg (rat, oral)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
It is a colorless liquid with a characteristic almond-like odor. Benzaldehyde is the primary component of bitter almond oil and can be extracted from a number of other natural sources. Synthetic benzaldehyde is the flavoring agent in imitation almond extract, which is used to flavor cakes and other baked goods.
As of 1999, 7000 tonnes of synthetic and 100 tonnes of natural benzaldehyde were produced annually. Liquid phase chlorination and oxidation of toluene are the main routes. Numerous other methods have been developed, such as the partial oxidation of benzyl alcohol, alkali hydrolysis of benzal chloride, and the carbonylation of benzene.
A significant quantity of natural benzaldehyde is produced from cinnamaldehyde obtained from cassia oil by the retro-aldol reaction: the cinnamaldehyde is refluxed in an aqueous/alcoholic solution between 90 °C and 150 °C with a base (most commonly sodium carbonate or bicarbonate) for 5 to 80 hours, followed by distillation of the formed benzaldehyde. This reaction also yields acetaldehyde. The natural status of benzaldehyde obtained in this way is controversial.
Almonds, apricots, apples and cherry kernels contain significant amounts of amygdalin. This glycoside breaks up under enzyme catalysis into benzaldehyde, hydrogen cyanide and two molecules of glucose.
Benzaldehyde can be oxidized to the odorless benzoic acid, which is a common impurity in laboratory samples. Benzyl alcohol can be formed from benzaldehyde by means of hydrogenation. Reaction of benzaldehyde with anhydrous sodium acetate and acetic anhydride yields cinnamic acid, while alcoholic potassium cyanide can be used to catalyze the condensation of benzaldehyde to benzoin. Benzaldehyde undergoes disproportionation upon treatment with concentrated alkali (Cannizzaro reaction): one molecule of the aldehyde is reduced to the corresponding alcohol and another molecule is simultaneously oxidized to benzoic acid.
In industrial settings, benzaldehyde is used chiefly as a precursor to other organic compounds, ranging from pharmaceuticals to plastic additives. The aniline dye malachite green is prepared from benzaldehyde and dimethylaniline. Benzaldehyde is also a precursor to certain acridine dyes. Via aldol condensations, benzaldehyde is converted into derivatives of cinnamaldehyde and styrene. The synthesis of mandelic acid starts from benzaldehyde:
Benzaldehyde is used as a bee repellant. A small amount of benzaldehyde solution is placed on a fume board near the honeycombs. The bees then move away from the honey combs to avoid the fumes. The beekeeper can then remove the honey frames from the bee hive with less risk to both bees and beekeeper.
As used in food, cosmetics, pharmaceuticals, and soap, benzaldehyde is "generally regarded as safe" (GRAS) by the US FDA and FEMA. This status was reaffirmed after a review in 2005. It is accepted in the European Union as a flavoring agent. Toxicology studies indicate that it is safe and non-carcinogenic in the concentrations used for foods and cosmetics, and may even have carcinostatic (anti-cancer) properties.
In high concentrations as seen in industrial settings, however, it can be dangerous. For a 70 kg human, the lethal dose is estimated at 50 mL. An acceptable daily intake of 15 mg/day has been identified for benzaldehyde by the United States Environmental Protection Agency. Benzaldehyde does not accumulate in human tissues. It is metabolized and then excreted in urine.
- Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 908. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
- William M. Haynes (2014), CRC Handbook of Chemistry and Physics (95th ed.), CRC press, pp. 3–34, ISBN 9781482208689
- "GESTIS Substance database". Institute for Occupational Safety and Health of the German Social Accident Insurance. Retrieved 21 August 2012.
- http://www.freepatentsonline.com/1416128.pdf, United States Patent 1416128 - Process of treating nut kernels to produce food ingredients.
- Illustrated, Cook's (2013-10-01). The Cook's Illustrated Baking Book. America's Test Kitchen. ISBN 9781936493784.
- In 1803 C. Martrès published a manuscript on the oil of bitter almonds: "Recherches sur la nature et le siège de l'amertume et de l'odeur des amandes amères" (Research on the nature and location of the bitterness and the smell of bitter almonds). However, the memoir was largely ignored until an extract was published in 1819: Martrès fils (1819) "Sur les amandes amères," Journal de Pharmacie, vol. 5, pages 289-296.
- Wöhler and Liebig (1832) "Untersuchungen über das Radikal der Benzoesäure" (Investigations of the radical of benzoic acid), Annalen der Pharmacie, vol. 3, pages 249-282.
- Innovation in food engineering : new techniques and products. Passos, Maria Laura., Ribeiro, Claudio P. Boca Raton, FL: CRC Press. 2010. p. 87. ISBN 9781420086072. OCLC 500683261.
- Friedrich Brühne and Elaine Wright “Benzaldehyde” in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_463
- http://www.patentstorm.us/patents/pdfs/patent_id/4617419.html, Process for preparing natural benzaldehyde and acetaldehyde, natural benzaldehyde and acetaldehyde compositions, products produced thereby and organoleptic utilities therefor, Charles Wienes, Middletown; Alan O. Pittet, Atlantic Highlands, both of N.J.
- Ashurst, Philip R.; Dennis, M. J. (2013-11-11). Food Authentication. Springer Science & Business Media. p. 274. ISBN 9781461311195.
- Adams, T. B.; Cohen, S. M.; Doull, J.; Feron, V. J.; Goodman, J. I.; Marnett, L. J.; Munro, I. C.; Portoghese, P. S.; Smith, R. L. (2005-08-01). "The FEMA GRAS assessment of benzyl derivatives used as flavor ingredients". Food and Chemical Toxicology. 43 (8): 1207–1240. doi:10.1016/j.fct.2004.11.014. ISSN 0278-6915. PMID 15950815.
- Beltran-Garcia, Miguel J.; Estarron-Espinosa, Mirna; Ogura, Tetsuya (1997). "Volatile Compounds Secreted by the Oyster Mushroom (Pleurotus ostreatus)and Their Antibacterial Activities". Journal of Agricultural and Food Chemistry. 45 (10): 4049. doi:10.1021/jf960876i.
- Andersen, Alan (2006-01-01). "Final report on the safety assessment of benzaldehyde". International Journal of Toxicology. 25 Suppl 1: 11–27. doi:10.1080/10915810600716612. ISSN 1091-5818. PMID 16835129.
- Evans, Elizabeth; Butler, Carol (2010-02-09). Why Do Bees Buzz?: Why Do Bees Buzz? Fascinating Answers to Questions about Bees. Rutgers University Press. pp. 177–178. ISBN 9780813549200.
- Sanford, Malcolm T.; Bonney, Richard E. (2010-01-01). Storey's Guide to Keeping Honey Bees: Honey Production, Pollination, Bee Health. Storey Publishing. p. 167. ISBN 9781603425506.
- Friedrich Brühne; Elaine Wright (2007), "Benzaldehyde", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 11
- Assessment, US EPA National Center for Environmental. "HEALTH AND ENVIRONMENTAL EFFECTS PROFILE FOR BENZALDEHYDE". cfpub.epa.gov. Retrieved 2017-09-16.