Propyne
Names | |
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Preferred IUPAC name | |
Other names
Methylacetylene
Methyl acetylene Allylene | |
Identifiers | |
3D model (
JSmol ) |
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878138 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.000.754 |
EC Number |
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MeSH | C022030 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C3H4 | |
Molar mass | 40.0639 g/mol |
Appearance | Colorless gas[2] |
Odor | Sweet[2] |
Density | 0.53 g/cm3 |
Melting point | −102.7 °C (−152.9 °F; 170.5 K) |
Boiling point | −23.2 °C (−9.8 °F; 250.0 K) |
Vapor pressure | 5.2 atm (20°C)[2] |
Hazards | |
Explosive limits
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1.7%-?[2] |
NIOSH (US health exposure limits): | |
PEL (Permissible)
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TWA 1000 ppm (1650 mg/m3)[2] |
REL (Recommended)
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TWA 1000 ppm (1650 mg/m3)[2] |
IDLH (Immediate danger) |
1700 ppm[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Propyne (methylacetylene) is an
Production and equilibrium with propadiene
Propyne exists in equilibrium with propadiene, the mixture of propyne and propadiene being called MAPD:
The coefficient of equilibrium Keq is 0.22 at 270 °C or 0.1 at 5 °C. MAPD is produced as a side product, often an undesirable one, by
of propene.Laboratory methods
Propyne can also be synthesized on laboratory scale by reducing
vapors over magnesium.Use as a rocket fuel
European space companies have researched using light
Organic chemistry
Propyne is a convenient three-carbon building block for
Propyne, along with
The chemical shift of an alkynyl proton and propargylic proton generally occur in the same region of the 1H NMR spectrum. In propyne, these two signals have almost exactly the same chemical shifts, leading to overlap of the signals, and the 1H NMR spectrum of propyne, when recorded in deuteriochloroform on a 300 MHz instrument, consists of a single signal, a sharp singlet resonating at 1.8 ppm.[9]
Notes
- ^ "Prop-1-yne" mistake fixed in the errata Archived 2019-08-01 at the Wayback Machine. The locant is omitted according to P-14.3.4.2 (d), p. 31.
References
- ISBN 978-0-85404-182-4.
- ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0392". National Institute for Occupational Safety and Health (NIOSH).
- ^ ).
- . Retrieved 20 February 2014.
- ^ Reiser, Edward II. (1896). "The preparation of Allylene, and the Action of Magnesium upon Organic Compounds". The Chemical News and Journal of Industrial Science. LXXIV: 78–80. Retrieved 20 February 2014.
- ^ Michael J. Taschner; Terry Rosen; Clayton H. Heathcock (1990). "Ethyl Isocrotonate". Organic Syntheses; Collected Volumes, vol. 7, p. 226.
- ^ US patent 5744071, Philip Franklin Sims, Anne Pautard-Cooper, "Processes for preparing alkynyl ketones and precursors thereof", issued 1996-11-19
- .
- OCLC 907161629.