Syntin

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title: "Syntin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["hydrocarbons", "rocket-fuels", "cyclopropanes", "substances-discovered-in-the-1960s", "soviet-inventions"] topic_path: "general/hydrocarbons" source: "https://en.wikipedia.org/wiki/Syntin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424850837 | ImageFile = Syntin.svg | ImageSize = 200px | ImageAlt = | PIN = 21-Methyl-11,21:22,31-tercyclopropane | OtherNames = 1-Methyl-1,2-dicyclopropylcyclopropane; Sintin; Synthin; Tsycklin; Tsiklin |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo = 93223-46-2 | PubChem = 519050 | ChemSpiderID_Ref = | ChemSpiderID = 452765 | InChI = 1/C10H16/c1-10(8-4-5-8)6-9(10)7-2-3-7/h7-9H,2-6H2,1H3 | InChIKey = GTKAAVZEFUFXDD-UHFFFAOYAR | StdInChI_Ref = | StdInChI = 1S/C10H16/c1-10(8-4-5-8)6-9(10)7-2-3-7/h7-9H,2-6H2,1H3 | StdInChIKey_Ref = | StdInChIKey = GTKAAVZEFUFXDD-UHFFFAOYSA-N | SMILES = CC1(C2CC2)C(C3CC3)C1}} |Section2={{Chembox Properties | C=10 | H=16 | Appearance = | Density = 0.851 g/mL | MeltingPt = | BoilingPtC = 158 | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }}

Syntin is a hydrocarbon with the molecular formula C10H16 used as a rocket fuel. It is a mixture of four stereoisomers (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 rings, the molecule has a highly positive enthalpy of formation: ΔfH°(l)= 133 kJ/mol (980 kJ/kg, the average value for the isomeric mixture),{{cite web |url=http://www.mathnet.ru/links/aad75c8a915bf9d604a2a3200dd4cb2c/dan39595.pdf |last1=A.P. |first1=Mesheheryakov |last2=V.G. |first2=Glukhovtsev |last3=A.D. |first3=Petrov |publisher=Institute of Organic Chemistry, UdSSR Academy of Sciences. |script-title=ru:СИНТЕЗ 1-МЕТИЛ-1,2-ДИЦИКЛОПРОПИЛЦИКЛОПРОПАНА |trans-title="Synthesis of 1-Methyl-1,2-Dicyclopropylcyclopropane" |language=ru |date=26 September 1959 |pages=779–781 |access-date=22 July 2022}} bringing additional energy into the combustion process. 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 as fuel for the Soyuz-U2 rocket from 1982 until 1995.{{cite web |url=http://www.lpre.de/energomash/RD-107/index.htm |script-title=ru:ЖРД РД-107 и РД-108 и их модификации |trans-title=Liquid Rocket Engines RD-107/108 and their modifications |website=www.lpre.de |language=ru |access-date=22 July 2022}}{{cite web |url=http://www.novosti-kosmonavtiki.ru/nk/forum-pic/Omar_NK2008-02.pdf |script-title=ru:Последний бой углеводородов? |trans-title=The last battle of hydrocarbons? |website=novosti-kosmonavtiki.ru |publisher=Novosti Kosmonavtiki |language=ru |date=2008 |series=Volume 18, No 2. |pages=44–46 |url-status=dead |archive-url=https://web.archive.org/web/20090920132913/http://www.novosti-kosmonavtiki.ru/nk/forum-pic/Omar_NK2008-02.pdf |archive-date=20 September 2009}}

It was first synthesized in the USSR in 1959 and brought to mass production in the 1970s. It was prepared in a multi-step synthetic process from easily obtained acetylcyclopropane (the 3rd molecule): :[[File:Syntin synthesis 01.svg|600px|left|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, the seventy-first and last Soyuz-U2 rocket launched, being the last rocket fueled with Syntin.

Stereoisomers

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

:[[File:Syntin Stereoisomers Formulae V.1.svg|500px|left|Four Syntin Stereoisomers]]

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

References

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

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hydrocarbonsrocket-fuelscyclopropanessubstances-discovered-in-the-1960ssoviet-inventions