Propyne (methylacetylene) is an
alkyne with the
chemical formula
In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbol ...
. It is a component of
MAPD gas—along with its
isomer propadiene (allene), which was commonly used in
gas welding
Principle of burn cutting
Oxy-fuel welding (commonly called oxyacetylene welding, oxy welding, or gas welding in the United States) and oxy-fuel cutting are processes that use fuel gases (or liquid fuels such as gasoline or petrol, diesel, ...
. Unlike
acetylene, propyne can be safely
condensed.
[Peter Pässler, Werner Hefner, Klaus Buckl, Helmut Meinass, Andreas Meiswinkel, Hans-Jürgen Wernicke, Günter Ebersberg, Richard Müller, Jürgen Bässler, Hartmut Behringer, Dieter Mayer, "Acetylene" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim 2007 ().]
Production and equilibrium with propadiene
Propyne exists in equilibrium with
propadiene, the mixture of propyne and propadiene being called MAPD:
:
H3CC#CH <=> H2C=C=CH2
The coefficient of equilibrium ''K''
eq is 0.22 at 270 °C or 0.1 at 5 °C.
MAPD is produced as a side product, often an undesirable one, by
cracking propane to produce
propene
Propylene, also known as propene, is an unsaturated organic compound with the chemical formula CH3CH=CH2. It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petro ...
, an important
feedstock in the
chemical industry.
[ MAPD interferes with the ]catalytic
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...
polymerization
In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many fo ...
of propene.
Laboratory methods
Propyne can also be synthesized on laboratory scale by reducing 1-propanol, allyl alcohol
Allyl alcohol ( IUPAC name: prop-2-en-1-ol) is an organic compound with the structural formula . Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a raw material ...
or acetone
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour.
Acetone is miscib ...
vapors over magnesium.
Use as a rocket fuel
European space companies have researched using light hydrocarbons
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or e ...
with liquid oxygen
Liquid oxygen—abbreviated LOx, LOX or Lox in the aerospace, submarine and gas industries—is the liquid form of molecular oxygen. It was used as the oxidizer in the first liquid-fueled rocket invented in 1926 by Robert H. Goddard, an app ...
, a relatively high performing liquid rocket propellant
The highest specific impulse chemical rockets use liquid propellants (liquid-propellant rockets). They can consist of a single chemical (a monopropellant) or a mix of two chemicals, called bipropellants. Bipropellants can further be divided into ...
combination that would also be less toxic than the commonly used MMH/NTO (monomethylhydrazine
Monomethylhydrazine (mono-methyl hydrazine, MMH) is a highly toxic, volatile hydrazine derivative with the chemical formula . It is used as a rocket propellant in bipropellant rocket engines because it is hypergolic with various oxidizers such as ...
/nitrogen tetroxide
Dinitrogen tetroxide, commonly referred to as nitrogen tetroxide (NTO), and occasionally (usually among ex-USSR/Russia rocket engineers) as amyl, is the chemical compound N2O4. It is a useful reagent in chemical synthesis. It forms an equilibrium ...
). Their research showed that propyne would be highly advantageous as a rocket fuel
Rocket propellant is the reaction mass of a rocket. This reaction mass is ejected at the highest achievable velocity from a rocket engine to produce thrust. The energy required can either come from the propellants themselves, as with a chemical ...
for craft intended for low Earth orbit
A low Earth orbit (LEO) is an orbit around Earth with a period of 128 minutes or less (making at least 11.25 orbits per day) and an eccentricity less than 0.25. Most of the artificial objects in outer space are in LEO, with an altitude never mor ...
al operations. They reached this conclusion based upon a specific impulse
Specific impulse (usually abbreviated ) is a measure of how efficiently a reaction mass engine (a rocket using propellant or a jet engine using fuel) creates thrust. For engines whose reaction mass is only the fuel they carry, specific impulse is ...
expected to reach 370 s with oxygen as the oxidizer, a high density
Density (volumetric mass density or specific mass) is the substance's mass per unit of volume. The symbol most often used for density is ''ρ'' (the lower case Greek letter rho), although the Latin letter ''D'' can also be used. Mathematical ...
and power density
Power density is the amount of power (time rate of energy transfer) per unit volume.
In energy transformers including batteries, fuel cells, motors, power supply units etc., power density refers to a volume, where it is often called volum ...
—and the moderate boiling point, which makes the chemical easier to store than fuels that must be kept at extremely low temperatures. (See ''cryogenics
In physics, cryogenics is the production and behaviour of materials at very low temperatures.
The 13th IIR International Congress of Refrigeration (held in Washington DC in 1971) endorsed a universal definition of “cryogenics” and “cr ...
''.)
Organic chemistry
Propyne is a convenient three-carbon building block for organic synthesis. Deprotonation with ''n''-butyllithium gives propynyllithium. This nucleophilic
In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are ...
reagent adds to carbonyl
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containi ...
groups, producing alcohols and ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...
s. Whereas purified propyne is expensive, MAPP gas could be used to cheaply generate large amounts of the reagent.
Propyne, along with 2-butyne
2-Butyne (dimethylacetylene, crotonylene or but-2-yne) is an alkyne with chemical formula CH3C≡CCH3. Produced artificially, it is a colorless, volatile, pungent liquid at standard temperature and pressure.
2-Butyne is of interest to physical c ...
, is also used to synthesize alkylated hydroquinone
Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''para' ...
s in the total synthesis
Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes i ...
of vitamin E
Vitamin E is a group of eight fat soluble compounds that include four tocopherols and four tocotrienols. Vitamin E deficiency, which is rare and usually due to an underlying problem with digesting dietary fat rather than from a diet low in vi ...
.
Notes
References
External links
NIST Chemistry WebBook page for propyne
German Aerospace Center
Nova Chemicals
{{Authority control
Alkynes
Fuel gas
Rocket fuels