Syntin

Syntin
Names
IUPAC name
1′-Methyl-1,1′:2′,1′′-tercyclopropane
Other names
1-Methyl-1,2-dicyclopropylcyclopropane; Sintin; Synthin; Tsycklin
Identifiers
3D model (JSmol)
ChemSpider
Properties
C10H16
Molar mass 136.24 g·mol−1
Density 0.851 g/mL
Boiling point 158 °C (316 °F; 431 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Syntin is a hydrocarbon with the molecular formula C10H16 used as a rocket fuel. It is a mixture of cis and trans isomers. It has a density of 0.851 g/mL, and a boiling point of 158 °C. Due to the presence of three strained cyclopropane rings, the molecule has high positive enthalpy of formation: ΔfH°(l)= 133 kJ/mol (980 kJ/kg, the average value for the isomeric mixture), bringing additional energy during the combustion process. Thus, it has advantages over the traditional hydrocarbon fuels, such as RP-1, due to higher density, lower viscosity and higher specific heat of oxidation.

Syntin was used in the Soviet Union and later Russia in 1980s-1990s as fuel for the Soyuz-U2 rocket. It was first synthesized in USSR in the 1960s and brought to mass production in the 1970s. It was prepared in a multi-step synthetic process from common hydrocarbon sources:

After dissolution of the USSR, the production of this fuel became too expensive and was halted.

Stereoisomers

Syntin is a molecule with two stereocenters at the central cyclopropane ring. Thus, the following four stereoisomers may exist:

In practice, the fuel has been used as mixture of all four stereoisomers.

See also

References

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