1-chloropropene
Structural formula | ||||||||||||||||
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Structural formulas of the trans isomer (left) and the cis isomer (right) | ||||||||||||||||
General | ||||||||||||||||
Surname | 1-chloropropene | |||||||||||||||
other names |
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Molecular formula | C 3 H 5 Cl | |||||||||||||||
Brief description |
colorless to yellowish liquid |
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properties | ||||||||||||||||
Molar mass | 76.52 g mol −1 | |||||||||||||||
Physical state |
liquid |
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density |
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Melting point |
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boiling point |
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Vapor pressure |
675.8 hPa (25 ° C) |
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solubility | ||||||||||||||||
Refractive index |
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safety instructions | ||||||||||||||||
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Toxicological data | ||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C |
1-chloropropene is a chemical compound from the group of chlorinated alkenes .
Isomerism
1-Chloropropene occurs in two isomeric forms of the cis form [synonym: ( Z ) form] and the trans form [synonym: ( E ) form]. If “1-chloropropene” is mentioned in the scientific literature or in this article without reference to the cis or trans form, an unspecified mixture of cis and trans forms is meant. Structural isomers of 1-chloropropene are 2-chloropropene and 3-chloropropene (= allyl chloride).
Extraction and presentation
1-chloropropene is formed when hydrogen chloride is added to propyne . With a yield of 33%, the compound can be prepared by hydrogenation of 1,3-dichloropropane in cyclohexane at 100 ° C and 30-40 atm with an aluminum - or rhodium catalyst are presented.
It is formed as the main product from 1,1-dichloropropane with ethanolic potassium hydroxide solution.
properties
1-chloropropene is a very volatile, easily flammable, colorless to yellowish liquid that is practically insoluble in water.
use
1-chloropropene can be used to make propyne .
safety instructions
1-chloropropene forms highly flammable vapor-air mixtures. The compound has a flash point of 0 ° C. The explosion range is between 4.5% by volume as the lower explosion limit (LEL) and 16% by volume as the upper explosion limit (UEL). The compound was characterized as carcinogenic in long-term animal experiments .
literature
- Beilstein Syst. No. 10: H, p. 198 .
Individual evidence
- ↑ a b c d e f g Entry on 1-chloropropene, cis, trans in the GESTIS substance database of the IFA , accessed on February 12, 2019(JavaScript required) .
- ↑ a b c d e f g h i j k David R. Lide: CRC Handbook of Chemistry and Physics, 84th Edition . CRC Press, 2003, pp. 122 ( limited preview in Google Book search).
- ↑ Entry on 1-Propenyl Chloride (cis- and trans- mixture) at TCI Europe, accessed on February 12, 2019.
- ^ Daniel Bellus, Manfred Braun, Tonia Freysoldt, Richard Göttlich, Jens Hartung, Monica Härtinger, Stefan Härtinger, Paul Margaretha, Wolf-Diethard Pfeiffer, Kathrin-Maria Roy, Karola Rück-Braun, Ernst Schaumann, Theodor Troll, Henri Ulrich: Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol ... - Daniel Bellus, Manfred Braun, Tonia Freysoldt, Richard Göttlich, Jens Hartung, Monica Härtinger, Stefan Härtinger, Paul Margaretha, Wolf-Diethard Pfeiffer, Kathrin-Maria Roy, Karola Rück-Braun, Ernst Schaumann, Theodor Troll, Henri Ulrich . Georg Thieme Verlag, 2014, p. 117 ( limited preview in Google Book search).
- ^ Calvin L. Stevens, Carl R. Johnson, Don C. de Jongh, Norman A. Lebel, Norman L. Allinger, Michael P. Cava: Gnichtel, Horst: Organische Chemie. [Main volume] Walter de Gruyter, 1980, p. 641 ( limited preview in Google Book search).
- ^ Dietrich Henschler: Toxicology of organochlorine compounds . John Wiley & Sons, 2008, ISBN 3-527-62421-X , pp. 34 ( limited preview in Google Book search).