Heptanal
| Names | |
|---|---|
| Preferred IUPAC name
Heptanal | |
| Other names
Heptanaldehyde
Aldehyde C-7 Enanthaldehyde Heptyl aldehyde n-Heptanal | |
| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C7H14O | |
| Molar mass | 114.18 |
| Appearance | Clear liquid |
| Density | 0.80902 at 30 °C |
| Melting point | −43.3 °C (−45.9 °F; 229.8 K) |
| Boiling point | 152.8 °C (307.0 °F; 425.9 K) |
| Slightly soluble | |
| −81.02·10−6 cm3/mol | |
| Related compounds | |
Related aldehydes
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Hexanal |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Heptanal or heptanaldehyde is an alkyl aldehyde. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants.[2]
Production
[edit | edit source]The formation of heptanal in the fractional distillation of castor oil[3] was already described in 1878. The large-scale production is based on the pyrolytic cleavage of ricinoleic acid[4] (Arkema method) and on the hydroformylation of 1-hexene with rhodium 2-ethylhexanoate as a catalyst upon addition of some 2-ethylhexanoic acid (Oxea method):[2][5]
Heptanal naturally occurs in the essential oils of ylang-ylang (Cananga odorata), clary sage (Salvia sclarea), lemon (Citrus x limon), bitter orange (Citrus x aurantium), rose (Rosa) and hyacinth (Hyacinthus).[6]
Properties
[edit | edit source]Heptanal is a flammable, slightly volatile colorless liquid of pervasive fruity to oily-greasy odor,[7] which is miscible with alcohols[6] and practically insoluble in water.[8] Because of its sensitivity to oxidation, heptanal is filled under nitrogen and stabilized with 100 ppm hydroquinone.[9]
Heptanal forms flammable vapor-air mixtures. The compound has a flash point of 39.5 °C.[8] The explosion range is between 1.1% by volume as the lower explosion limit (LEL) and 5.2% by volume as the upper explosion limit.[8] Its ignition temperature is 205 °C.[8]
Uses
[edit | edit source]Heptanal can be used for the production of 1-heptanol via hydrogenation:
The oxidation of heptanal with oxygen in the presence of a rhodium catalysts leads at 50 °C to heptanoic acid in 95% yield.[10] Heptanal reacts with benzaldehyde in a Knoevenagel reaction under basic catalysis with high yield and selectivity (> 90%) to jasminaldehyde,[11][2] which is mostly used in fragrances for its jasmine-like aroma as a cis/trans isomer mixture.[12]
A by-product of the given reaction is the unpleasant rancid smelling (Z)-2-pentyl-2-nonenal.[13] Nevertheless, heptanal can be converted into (Z)-2-pentyl-2-nonenal virtually quantitatively in the presence of aqueous boric acid upon azeotropic removal of water.[14]
Full hydrogenation provides the branched primary alcohol 2-pentylnonan-1-ol, also accessible from the Guerbet reaction from heptanol.[15]
References
[edit | edit source]- ^ Merck Index, 11th Edition, 4578.
- ^ a b c Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ F. Krafft, Distillation of castor oil, under reduced pressure, Analyst, 3, 329a (1878).
- ^ A. Chauvel, G. Lefebvre, Petrochemical Processes: Technical and Economic Characteristics, vol. 2, p. 277, Editions Technip, Paris, 1989, Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)..
- ^ A. Fischbach et al on behalf of Oxea Deutschland GmbH (20 May 2009). Verfahren zur Herstellung von Aldehyden Archived 2016-03-04 at the Wayback Machine, German patent DE 102007053385.
- ^ a b G. A. Burdock, Fenaroli's Handbook of Flavor Ingredients, Fifth Edition, 2005, CRC Press, Boca Raton, Fl., Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)..
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b c d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ Acros Organics (rev. 19 Nov 2012). Heptaldehyde, stabilized (safety data sheet).
- ^ H. Springer and P. Lappe, on behalf of Celanese Chem Europe GmbH (3 May 2001). Verfahren zur Herstellung aliphatischer Carbonsäuren aus Aldehyden Archived 2016-03-04 at the Wayback Machine, German patent DE 10010771.
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ alpha-Amylzimtaldehyd (rev. 4 Aug 2000) at the Riechstofflexikon [Odorant Dictionary], vol. A.
- ^ J. M. Hornback, Organic Chemistry, 2nd edition, p. 886, Thomson Brooks/Cole, 2006, Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)..
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ G.H. Knothe: Lipid Chemistry, Guerbet Compounds Archived 2016-05-21 at the Wayback Machine, AOCS Lipid Library, 22 December 2011.