Synthesis of butadiynes

Chemistry of hydrocarbon compounds – Unsaturated compound synthesis – Triple-bond product

Reexamination Certificate

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C585S505000

Reexamination Certificate

active

10817411

ABSTRACT:
Provided is a method for the synthesis of 1,4-dicyclopropyl-1,3-butadiyne from CPA. Such butadiyne is prepared by oxidative coupling of cyclopropyl acetylene (CPA) using catalytic amounts each of copper (I)chloride and tetrametylethylenediamine (TMEDA) in isopropanol under aerobic conditions. The resulting butadiyne can serve as a fuel or a fuel additive for combustion in engines propelling motor vehicles, marine vessels, aircraft, rockets and other vehicles.

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patent: 7083690 (2006-08-01), Dobbins et al.
Armin de Meijere, Frank Jaekel, Arndt Simon, Horst Borrmann, Jurgen Kohler, Dan Johnels, and Lawrence T. Scott Regioselective Coupling of Ethynylcyclopropane Units: Hexaspiro[2.0.2.4.2.0.2.4.2.0.2.4]triaconta-7,9,17,19,27,29-hexayne J. Am. Chem. Soc. 1991,113.3935-3941.
Sergei Kozhushkov, Thomas Haumann, Roland Boese, Burkhardt Knieriem, Stefan Scheib, Peter Bauerle, and Armin de Maeijere The Reactivity of 1,3-Butadiyne Moieties in the ‘Exploding’ [n] Rotanes- A Crown of Thiophenes Angew. Chem. Int. Ed. Engl. 1995.34.No. 7 p. 781.
Peter Timmerman, Harry L Anderson, Rudiger Faust, Jean-Francois Nierengarten, Tilo Habicher, Paul Seiler, Francois Diederich Fullerence-Acetylene Hybrids: Towards a Novel Class of Molecular Carbon Allotropes Tetrahedron, vol. 52, No. 14, pp. 4925-4947,1996.

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