# Syntin

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Syntin Names Preferred IUPAC name 21-Methyl-11,21:22,31-tercyclopropane Other names 1-Methyl-1,2-dicyclopropylcyclopropane; Sintin; Synthin; Tsycklin; Tsiklin Identifiers CAS Number 93223-46-2 Y 3D model (JSmol) Interactive image ChemSpider 452765 Y PubChem CID 519050 CompTox Dashboard (EPA) DTXSID90333879 InChI InChI=1S/C10H16/c1-10(8-4-5-8)6-9(10)7-2-3-7/h7-9H,2-6H2,1H3 N Key: GTKAAVZEFUFXDD-UHFFFAOYSA-N N InChI=1/C10H16/c1-10(8-4-5-8)6-9(10)7-2-3-7/h7-9H,2-6H2,1H3 Key: GTKAAVZEFUFXDD-UHFFFAOYAR SMILES CC1(C2CC2)C(C3CC3)C1 Properties Chemical formula C10H16 Molar mass 136.238 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). N verify (what is YN ?) Infobox references

Chemical compound

**Syntin** is a [hydrocarbon](/source/Hydrocarbon) with the [molecular formula](/source/Molecular_formula) C10H16 used as a rocket fuel. It is a mixture of four [stereoisomers](/source/Stereoisomerism) (see below). It has a density of 0.851 g/mL, and a boiling point of 158 °C. Due to the presence of three strained [cyclopropane](/source/Cyclopropane) rings, the molecule has a highly positive [enthalpy of formation](/source/Enthalpy_of_formation): Δf*H*°(l)= 133 kJ/mol (980 kJ/kg, the average value for the isomeric mixture),[1] bringing additional energy into the combustion process. It has advantages over the traditional hydrocarbon fuels, such as [RP-1](/source/RP-1), due to higher density, lower [viscosity](/source/Viscosity) and higher [specific heat of oxidation](/source/Specific_heat_of_oxidation).

Syntin was used in the [Soviet Union](/source/Soviet_Union) and later [Russia](/source/Russia) as fuel for the [Soyuz-U2](/source/Soyuz-U2) rocket from 1982 until 1995.[2][3]

It was first synthesized in the USSR in 1959[1] and brought to mass production in the 1970s. It was prepared in a multi-step synthetic process from easily obtained acetylcyclopropane (the 3rd molecule):

- Syntin synthesis 01

After dissolution of the USSR, the production of this fuel was halted due to the expense of the synthesis. On September 3, 1995, [Soyuz TM-22](/source/Soyuz_TM-22), the seventy-first and last [Soyuz-U2](/source/Soyuz-U2) rocket launched, being the last rocket fueled with Syntin.[3]

## Stereoisomers

Syntin has two stereocenters at the central cyclopropane ring. Thus, four stereoisomers exist:

- Four Syntin Stereoisomers

In practice, syntin is used as a [racemic](/source/Racemic) mixture (a mixture where all stereoisomers are present in equal amounts).

## See also

- [Dicyclopentadiene](/source/Dicyclopentadiene)

## References

1. ^ [***a***](#cite_ref-Mesheheryakov_1-0) [***b***](#cite_ref-Mesheheryakov_1-1) A.P., Mesheheryakov; V.G., Glukhovtsev; A.D., Petrov (26 September 1959). [СИНТЕЗ 1-МЕТИЛ-1,2-ДИЦИКЛОПРОПИЛЦИКЛОПРОПАНА](https://www.mathnet.ru/links/aad75c8a915bf9d604a2a3200dd4cb2c/dan39595.pdf) ["Synthesis of 1-Methyl-1,2-Dicyclopropylcyclopropane"] (PDF) (in Russian). Institute of Organic Chemistry, UdSSR Academy of Sciences. pp. 779–781. Retrieved 22 July 2022.

1. **[^](#cite_ref-2)** [ЖРД РД-107 и РД-108 и их модификации](http://www.lpre.de/energomash/RD-107/index.htm) [Liquid Rocket Engines RD-107/108 and their modifications]. *www.lpre.de* (in Russian). Retrieved 22 July 2022.

1. ^ [***a***](#cite_ref-hydrocarbons_3-0) [***b***](#cite_ref-hydrocarbons_3-1) [Последний бой углеводородов?](https://web.archive.org/web/20090920132913/http://www.novosti-kosmonavtiki.ru/nk/forum-pic/Omar_NK2008-02.pdf) [The last battle of hydrocarbons?] (PDF). *novosti-kosmonavtiki.ru*. Volume 18, No 2. (in Russian). Novosti Kosmonavtiki. 2008. pp. 44–46. Archived from [the original](http://www.novosti-kosmonavtiki.ru/nk/forum-pic/Omar_NK2008-02.pdf) (PDF) on 20 September 2009.

## Literature

- 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. [doi](/source/Doi_(identifier)):[10.2514/2.6946](https://doi.org/10.2514%2F2.6946)

- V. Azov, D. Vorontsov, "The last battle of hydrocarbons?", *Novosti Kosmonavtiki*, **2008**, *18*, No. 2 (301), 44–46.

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