Syntin

{{#if:0.851 g/mL1610|! style="background: #F8EABA; text-align: center;" colspan="2" | Properties

Syntin
File:Syntin.png
IUPAC name 1′-Methyl-1,1′:2′,1′′-tercyclopropane
Other names 1-Methyl-1,2-dicyclopropylcyclopropane; Sintin; Synthin; Tsycklin
Identifiers
CAS number	93223-46-2
Jmol-3D images	Image 1
SMILES CC1(C2CC2)C(C3CC3)C1 <p><p style="word-wrap: break-word;">
Molecular formula	C10H16
Molar mass	136.23 g mol−1
14pxY (verify) (what is: 10pxY/10pxN?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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: Δ_fH°(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 1960 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.

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.de:Syntin