Fatty aldehydes

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Structure of the fatty aldehyde dodecanal

Fatty aldehydes are aliphatic , long-chain aldehydes that can be monounsaturated or polyunsaturated . The fatty aldehydes include compounds such as octanal , nonanal , decanal or dodecanal . The nomenclature is derived from the nomenclature of the alkanes, supplemented by the ending -al for the aldehyde group. Sometimes their common names are also used.

Occurrence

Fatty aldehydes are a natural component of many natural substances such as the essential oils of various citrus fruits. Decanal, for example, is a component of orange peel oil . The pheromone cocktails of various insect pheromones contain fatty aldehydes. Fatty aldehydes have also been detected in the heart muscle of mammals .

Manufacturing

Fatty aldehydes can be produced by the dehydrogenation of fatty alcohols on copper-zinc catalysts . By hydroformylation of olefins , fatty aldehydes are produced on an industrial scale.

use

The majority of the fatty aldehydes produced by hydroformylation are processed directly into fatty alcohols. Many fatty aldehydes are used as a fragrance in perfume production . An example is 2-methylundecanal , which is the typical odor component of Chanel No. 5 represents. Decanal , whose sweet, floral scent is reminiscent of orange peel, is used, among other things, as a flavoring in the food industry and as a fragrance in the perfume industry.

Individual evidence

  1. Kehai Liu, Qiulin Chen, Yanjun Liu, Xiaoyan Zhou, Xichang Wang: Isolation and Biological Activities of Decanal, Linalool, Valencene, and Octanal from Sweet Orange Oil. In: Journal of Food Science. 77, 2012, pp. C1156-C1161, doi: 10.1111 / j.1750-3841.2012.02924.x .
  2. ^ Gerhard Kasang, Karl Ernst Kaißling, Otto Vostrowsky, Hans Jürgen Bestmann: Bombykal, a second pheromone component of the silk moth Bombyx mori L. In: Angewandte Chemie. 90, 1978, pp. 74-75, doi: 10.1002 / anie.19780900132 .
  3. ^ John R. Gilbertson et al .: Natural occurrence of free fatty aldehydes in bovine cardiac muscle. In: Journal of lipid research 13.4 (1972): pp. 491-499.
  4. Patent DE10044809A1 : Process for the production of aldehydes. Published on January 10, 2002 , inventors: Albrecht Schwerin, Lothar Friesenhagen, Gerrit Pelzer, Bernhard Gutsche.
  5. Ernst Wiebus, Boy Cornils: The large-scale oxo synthesis with immobilized catalyst. In: Chemical Engineer Technology. 66, 1994, pp. 916-923, doi: 10.1002 / cite.330660704 .
  6. Chemistry in its element - 2-methylundecanal. (No longer available online.) Archived from the original on May 28, 2014 ; Retrieved June 20, 2014 . Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. @1@ 2Template: Webachiv / IABot / www.rsc.org