Butyraldehyde
{{Chembox
| Watchedfields = changed
| verifiedrevid = 443970855
| Name =
| Reference = Merck Index, 11th Edition, 1591.
| ImageFileL1 = Butanal-skeletal.png
| ImageClassL1 = skin-invert-image
| ImageSizeL1 = 150px
| ImageNameL1 = Structural formula of butyraldehyde
| ImageFileR1 = Butyraldehyde_flat_structure.png
| ImageClassR1 = skin-invert-image
| ImageNameR1 = Flat structure
| ImageSizeR1 = 150px
| ImageFile2 = Butyraldehyde-3D-balls.png
| ImageClass2 = bg-transparent
| ImageName2 = Ball-and-stick model
| PIN = Butanal
| OtherNames = Butyraldehyde
| Section1 = {{Chembox Identifiers
| PubChem = 261
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = H21352682A
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01412
| EINECS = 204-646-6
| ChEMBL = 1478334
| 3DMet = B00287
| RTECS = ES2275000
| UNNumber = 1129
| InChI = 1/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3
| InChIKey = ZTQSAGDEMFDKMZ-UHFFFAOYAZ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZTQSAGDEMFDKMZ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 123-72-8
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 256
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 15743
| SMILES = O=CCCC
}}
| Section2 = {{Chembox Properties
| C=4 | H=8 | O=1
| Appearance = Colorless liquid
| Odor = Pungent, aldehyde odor
| Density = 0.8016 g/mL
| MeltingPtC = −96.86
| BoilingPtC = 74.8
| Solubility = 7.6 g/100 mL (20 °C)
| SolubleOther = Miscible with organic solvents
| CriticalTP = {{cvt|537|K|°C}},
{{cvt|4.32|MPa|atm}}
| RefractIndex = 1.3766
| MagSus = −46.08·10−6 cm3/mol
| Viscosity = 0.45 cP (20 °C)
| LogP = 0.88
| Dipole = 2.72 D
}}
| Section3 =
| Section4 = {{Chembox Thermochemistry
| HeatCapacity = 163.7 J·mol−1·K−1 (liquid)
103.4 J·mol−1·K−1 (gas)
| Entropy = 246.6 J·mol−1·K−1 (liquid)
343.7 J·mol−1·K−1 (gas)
| DeltaHform = −239.2 kJ·mol−1 (liquid)
−204.8 kJ·mol−1 (gas)
| DeltaHcombust = 2470.34 kJ·mol−1
}}
| Section5 =
| Section6 =
| Section7 = {{Chembox Hazards
| ExternalSDS = [https://www.sigmaaldrich.com/US/en/sds/aldrich/418102 Sigma-Aldrich]
| NFPA-H=3
| NFPA-F=3
| NFPA-R=0
| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}{{GESTIS|ZVG=28130 |CAS=123-72-8 |Name=Butyraldehyde |Date=13 March 2020 }}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|319}}
| PPhrases = {{P-phrases|280|304+340|302+352|210|305+351+338}}
| FlashPtC = -7
| AutoignitionPtC = 230
| ExploLimits = 1.9–12.5%
| LD50 = 2490 mg/kg (rat, oral)
}}
| Section8 = {{Chembox Related
| OtherFunction = Propionaldehyde
Pentanal
| OtherFunction_label = aldehyde
| OtherCompounds = Butan-1-ol
Butyric acid, isobutyraldehyde
}}
}}
Butyraldehyde, also known as butanal, is an organic compound with the formula CH3(CH2)2CHO. This compound is the aldehyde derivative of butane. It is a colorless flammable liquid with an unpleasant smell. It is miscible with most organic solvents.
Production
Butyraldehyde is produced almost exclusively by the hydroformylation of propylene:
: CH3CH=CH2 + H2 + CO → CH3CH2CH2CHO
Traditionally, hydroformylation was catalyzed by cobalt carbonyl but rhodium complexes are more common. The dominant technology involves the use of rhodium catalysts derived from the water-soluble ligand tppts. An aqueous solution of the rhodium catalyst converts the propylene to the aldehyde, which forms a lighter (less dense) immiscible phase. About 6 billion kilograms are produced annually in this manner. Butyraldehyde can be produced by the catalytic dehydrogenation of n-butanol. At one time, it was produced industrially by the catalytic hydrogenation of crotonaldehyde, which is derived from acetaldehyde.{{Ullmann |last=Raff |first=Donald K. |title=Butanals |year=2013|doi=10.1002/14356007.a04_447.pub2}}
Reactions and uses
Butyraldehyde undergoes reactions typical of alkyl aldehydes, and these define many of the uses of this compound. Important reactions include hydrogenation to the alcohol, oxidation to the acid, and base-catalyzed condensation. In the presence of a base, two equivalents of butyraldehyde undergoe aldol condensation to give 2-ethylhexenal. This unsaturated aldehyde is then partially hydrogenated to form 2-ethylhexanal, a precursor to plasticizers such as bis(2-ethylhexyl) phthalate.
Butyraldehyde is a component in the two-step synthesis of trimethylolpropane, which is used for the production of alkyd resins.{{Ullmann |last1=Werle |first1=Peter |title=Alcohols, Polyhydric |date=2008|doi=10.1002/14356007.a01_305.pub2 |isbn=978-3-527-30673-2 |last2=Morawietz |first2=Marcus |last3=Lundmark |first3=Stefan |last4=Sörensen |first4=Kent |last5=Karvinen |first5=Esko |last6=Lehtonen |first6=Juha}}
Image:Bis(2-ethylhexyl) phthalate.svg, a major plasticizer.]]
References
{{reflist}}
External links
- {{ICSC|0403|04}}
{{Authority control}}