Methylacetylene
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| Methylacetylene | |
|---|---|
| Image:Propyne.png | |
| Image:Propyne3D.png | |
| IUPAC name | Prop-1-yne |
| Other names | Methylacetylene Methyl acetylene Propyne |
| Identifiers | |
| CAS number | |
| SMILES | CC#C |
| Properties | |
| Molecular formula | C3H4 |
| Molar mass | 40.0639 g/mol |
| Density | 0.53 g/cm³ |
| Melting point |
-102 7°C |
| Boiling point |
-23.2 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Methylacetylene (propyne) is an alkyne with the chemical formula CH3C≡CH. It is a component of MAPP gas along with its isomer 1,2-propadiene (allene), which is commonly used in gas welding.
Use as a rocket fuel
Research by European space concerns into using light hydrocarbons with liquid oxygen as a relatively high performing propellant combination which would also be less toxic than the commonly used MMH/NTO (monomethylhydrazine/nitrogen tetroxide) systems, showed that propyne would be highly advantageous as a rocket fuel for craft intended for low Earth orbital operations. This conclusion was reached based upon a specific impulse expected to reach 370s if oxygen is used as oxidiser, a high density, and energy/volume ratio, and the moderate boiling point, which causes the chemical to present fewer problems in storage than for example a fuel that needs to be kept at extremely low temperatures. (See cryogenics.)
Use in organic chemistry
Propyne is a convenient three-carbon building block for synthesis. When propyne is condensed and treated with n-Butyllithium, solid propynyllithium is formed. This nucleophilic reagent can then be added to a carbonyl, producing a secondary alcohol. While purified propyne is expensive, in this reaction it can be replaced with MAPP gas to cheaply generate large amounts of the reagent.
References
ca:Metilacetilè de:Propin el:Προπίνιοla:Propinumsv:Propyn
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