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syntin : ウィキペディア英語版
syntin

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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: Δf''H''°(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.
== References ==

* A. P. Mesheheryakov, V. G. Glukhovtsev, A. D. Petrov, “Synthesis of 1-methyl-1,2-dicyclopropylcyclopropane”, ''Doklady Akademii Nauk SSSR'', 1960, ''130'', 779-81.
* Yu. P. Semenov, B. A. Sokolov, S. P. Chernykh, A. A. Grigor'ev, O. M. Nefedov, N. N. Istomin, G. M. Shirshov, “Multiple strained-ring alkane as high-performance liquid rocket fuel”, RU 2233385, C2 20040727.
* T. Edwards, “Liquid Fuels and Propellants for Aerospace Propulsion: 1903-2003”, ''Journal of Propulsion and Power'', 2003, ''19(6)'', 1089-1107.
* V. Azov, D. Vorontsov, "The last battle of hydrocarbons?", ''Novosti Kosmonavtiki'', 2008, ''18'', No. 2 (301), 44-46.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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