{{Short description|Organic compound (C4H9CHO)}} {{confuse|Pantanal}} {{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 444044555 | Reference = <ref name="Merck">''Merck Index'', 11th Edition, '''9813'''.</ref><ref>[http://chemicalland21.com/specialtychem/perchem/n-VALERALDEHYDE.htm n-Valeraldehyde] at chemicalland21.com</ref> | ImageFile = Valeraldehyde-Structural Formula V.1.svg | ImageClass = skin-invert-image | ImageAlt = Structural formula of pentanal | ImageFile1 = Pentanaldehyde 3D ball.png | ImageClass1 = bg-transparent | ImageAlt1 = Ball-and-stick model of the pentanal molecule | PIN = Pentanal | OtherNames = Pentanaldehyde<br>Valeraldehyde<br>Valeric aldehyde |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 110-62-3 | PubChem = 8063 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01919 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = B975S3014W | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 7772 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 84069 | SMILES = O=CCCCC | InChI = 1/C5H10O/c1-2-3-4-5-6/h5H,2-4H2,1H3 | InChIKey = HGBOYTHUEUWSSQ-UHFFFAOYAJ | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C5H10O/c1-2-3-4-5-6/h5H,2-4H2,1H3 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = HGBOYTHUEUWSSQ-UHFFFAOYSA-N |UNNumber = 2058 }} |Section2={{Chembox Properties | C=5 | H=10 | O=1 | Appearance = Clear liquid | Odor = Strong, acrid, pungent | Density = 0.8095 at 20 °C | MeltingPtC = −60 | BoilingPtC = 102 to 103 | Solubility = 14 g/L (20 °C) | Viscosity = 0.6 mPa·s (20 °C) | VaporPressure = 0.35 kPa (20 °C)<ref name=PGCH/> }} |Section3={{Chembox Hazards | PEL = none<ref name=PGCH>{{PGCH|0652}}</ref> | FlashPtC = 12 | AutoignitionPtC = 220 | FlashPt_ref = <ref name=PGCH/> | IDLH = N.D.<ref name=PGCH/> | REL = TWA 50 ppm (175 mg/m<sup>3</sup>)<ref name=PGCH/> | GHSPictograms = {{GHS02}}{{GHS07}} | NFPA-H = 3 | NFPA-F = 3 | NFPA-I = 0 | ExternalSDS = [https://www.fishersci.com/store/msds?partNumber=AC149565000&productDescription=VALERALDEHYDE+98%25+500ML&vendorId=VN00032119&countryCode=US&language=en Fisher Scientific] | LD50 = 3200 mg/kg (oral, rat)<br>4860 mg/kg (dermal, rabbit) | LC50 = 14.3 ppm (rat, 4h) }} |Section4={{Chembox Related | OtherFunction_label = aldehydes | OtherFunction = Butyraldehyde<br /> Hexanal }} }}
'''Pentanal''' (also called '''valeraldehyde''') is the organic compound with molecular formula {{chem2|C4H9CHO}}. Classified as an alkyl aldehyde, it is a colorless volatile liquid. Its odor is described as fermented, bready, fruity, nutty, berry.<ref>{{Cite web|url=http://www.thegoodscentscompany.com/data/rw1009331.html|title = Valeraldehyde, 110-62-3}}</ref>
==Production== Pentanal is obtained by hydroformylation of butene. Also C4 mixtures can be used as starting material like the so-called raffinate II, which is produced by steam cracking and contains (''Z'')- and (''E'')-2-butene, 1-butene, butane and isobutane. The conversion to the product is accomplished with synthesis gas in the presence of a catalyst consisting of a rhodium-bisphosphite complex and a sterically hindered secondary amine with a selectivity toward pentanal of at least 90%.<ref>[http://www.freepatentsonline.com/WO2009146985.html Patent WO 2009/146985 der Evonik Oxeno GmbH].</ref>
==Use== Pentanal undergoes the reactions characteristic of any alkyl aldehyde, i.e., oxidations, condensations, and reductions. 2-Octanone, produced for use in the fragrance industry, is obtained by the condensation of acetone and pentanal, followed by hydrogenation of the alkene.<ref>{{cite book |doi=10.1002/14356007.a15_077|chapter=Ketones |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2000 |last1=Siegel |first1=Hardo |last2=Eggersdorfer |first2=Manfred |isbn=9783527306732 }}</ref>
2-Propyl-2-heptenal is obtained from pentanal by aldol condensation, which is hydrogenated to the saturated branched 2-propylheptanol. This alcohol serves as a starting material for the PVC plasticizer di-2-propylheptyl phthalate (DPHP).
Pentanal (valeraldehyde) is oxidized to give valeric acid.<ref name=Ullmann>{{Ullmann|first1=Wilhelm|last1=Riemenschneider|title=Carboxylic Acids, Aliphatic|year=2002|doi=10.1002/14356007.a05_235}}</ref>
==References== <references/>
Category:Alkanals