Propadiene

{{Short description|1=Organic compound (H2C=C=CH2)}}

{{Chembox

| Verifiedimages = changed

| Watchedfields = changed

| verifiedrevid = 464215747

| ImageFileL1 = Propadiene structure.svg

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| ImageNameL1 = Stereo structural formula of propadiene with explicit hydrogens

| ImageFileR1 = Allene3D.png

| ImageFileR1_Ref = {{Chemboximage|correct|??}}

| ImageNameR1 = Spacefill model of propadiene

| ImageFile2 = Allene-CRC-IR-3D-balls.png

| ImageFile2_Ref = {{Chemboximage|correct|??}}

| ImageSize2 = 160

| ImageName2 = Ball and stick model of propadiene

| PIN = Propadiene{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 375 | doi = 10.1039/9781849733069 | isbn = 978-0-85404-182-4 | quote = The name allene, for {{chem2|CH2\dC\dCH2}}, is retained for general nomenclature only; substitution is allowed, but not by alkyl or any other group that extends the carbon chain, nor characteristic groups expressed by suffixes. The systematic name, propadiene, is the preferred IUPAC name. | last1 = Favre | first1 = Henri A. | last2 = Powell | first2 = Warren H. }}

| OtherNames = Allene
Propadiene

|Section1={{Chembox Identifiers

| CASNo = 463-49-0

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4AV0LZ8QKB

| PubChem = 10037

| ChemSpiderID = 9642

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 207-335-3

| UNNumber = 2200

| MeSHName = Propadiene

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 37601

| ChEMBL = 116960

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| Beilstein = 1730774

| Gmelin = 860

| SMILES = C=C=C

| StdInChI = 1S/C3H4/c1-3-2/h1-2H2

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = IYABWNGZIDDRAK-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}

|Section2={{Chembox Properties

| C=3 | H=4

| Appearance = Colorless gas

| MeltingPtC = -136

| BoilingPtC = -34

| LogP = 1.45}}

|Section3={{Chembox Hazards

| ExternalSDS = [http://encyclopedia.airliquide.com/Encyclopedia.asp?GasID=52 External MSDS]

| GHSPictograms = {{GHS flame}}{{GESTIS|ZVG=13750 |CAS=463-49-0 |Name=Allene |Date=17 November 2020}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|220}}

| PPhrases = {{P-phrases|210|377|381|410+403}}

| NFPA-H = 0

| NFPA-F = 4

| NFPA-R = 3

| ExploLimits = 13%}}

}}

Propadiene ({{IPAc-en|p|r|oʊ|p|ə|ˈ|d|aɪ|iː|n}}) or allene ({{IPAc-en|ˈ|æ|l|iː|n}}) is the organic compound with the formula {{chem2|H2C\dC\dCH2}}. It is the simplest allene, i.e. a compound with two adjacent carbon double bonds.{{GoldBookRef | title = allenes | file = A00238}} As a constituent of MAPP gas, it has been used as a fuel for specialized welding.

Production and equilibrium with methylacetylene

Propadiene exists in equilibrium with methylacetylene (propyne) and the mixture is sometimes called MAPD for methylacetylene-propadiene:

:{{chem2|H3C\sC\tCH ⇌ H2C\dC\dCH2}}

for which {{nowrap|1=K{{sub|eq}} = 0.22}} at 270 °C or 0.1 at 5 °C.

MAPD is produced as a side product, often an undesirable one, of dehydrogenation of propane to produce propene, an important feedstock in the chemical industry. MAPD interferes with the catalytic polymerization of propene.Klaus Buckl, Andreas Meiswinkel "Propyne" in Ullmann's Encyclopedia of Industrial Chemistry, 2008, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.m22_m01}}

Occurrence in Space

In 2019 it was announced that propadiene had been detected in the atmosphere of Saturn's moon Titan using the NASA Infrared Telescope Facility.{{Cite journal |last1=Lombardo |first1=Nicholas A |last2=Nixon |first2=Conor A |last3=Greathouse |first3=Thomas K |last4=Bézard |first4=Bruno |last5=Jolly |first5=Antoine |last6=Vinatier |first6=Sandrine |last7=Teanby |first7=Nicholas A |last8=Richter |first8=Matthew J |last9=G Irwin |first9=Patrick J |last10=Coustenis |first10=Athena |last11=Flasar |first11=F Michael |date=2019-08-20 |title=Detection of Propadiene on Titan |journal=The Astrophysical Journal Letters |volume=881 |issue=2 |pages=L33 |doi=10.3847/2041-8213/ab3860 |doi-access=free |issn=2041-8205|arxiv=1908.07424 }} This was the first time that propadiene had been detected in space, and the second structural isomeric pair (paired with propyne) detected in Titan's atmosphere, after HCN-HNC.{{Cite journal |last1=Moreno |first1=R. |last2=Lellouch |first2=E. |last3=Lara |first3=L. M. |last4=Courtin |first4=R. |last5=Bockelée-Morvan |first5=D. |last6=Hartogh |first6=P. |last7=Rengel |first7=M. |last8=Biver |first8=N. |last9=Banaszkiewicz |first9=M. |last10=González |first10=A. |date=December 2011 |title=First detection of hydrogen isocyanide (HNC) in Titan's atmosphere |url=http://www.aanda.org/10.1051/0004-6361/201118189 |journal=Astronomy & Astrophysics |volume=536 |pages=L12 |doi=10.1051/0004-6361/201118189 |issn=0004-6361}}{{Cite journal |last1=Hébrard |first1=E. |last2=Dobrijevic |first2=M. |last3=Loison |first3=J. C. |last4=Bergeat |first4=A. |last5=Hickson |first5=K. M. |date=May 2012 |title=Neutral production of hydrogen isocyanide (HNC) and hydrogen cyanide (HCN) in Titan's upper atmosphere |url=http://www.aanda.org/10.1051/0004-6361/201218837 |journal=Astronomy & Astrophysics |volume=541 |pages=A21 |doi=10.1051/0004-6361/201218837 |issn=0004-6361}}

References

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{{Hydrocarbons}}

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Category:Fuel gas

Category:Alkadienes

Category:Cumulated dienes