2-vinyl pyridine
Structural formula | |||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
![]() |
|||||||||||||||||||
General | |||||||||||||||||||
Surname | 2-vinyl pyridine | ||||||||||||||||||
Molecular formula | C 7 H 7 N | ||||||||||||||||||
Brief description |
light red-brown liquid with a pungent odor |
||||||||||||||||||
External identifiers / databases | |||||||||||||||||||
|
|||||||||||||||||||
properties | |||||||||||||||||||
Molar mass | 105.14 g mol −1 | ||||||||||||||||||
Physical state |
liquid |
||||||||||||||||||
density |
0.97 g cm −3 |
||||||||||||||||||
Melting point |
−50 ° C |
||||||||||||||||||
boiling point |
159 ° C |
||||||||||||||||||
Vapor pressure |
2.5 hPa (20 ° C) |
||||||||||||||||||
solubility |
|
||||||||||||||||||
Refractive index |
1.549 (20 ° C) |
||||||||||||||||||
safety instructions | |||||||||||||||||||
|
|||||||||||||||||||
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 |
2-vinylpyridine is a chemical compound from the pyridines group .
Extraction and presentation
2-Vinylpyridine 3 can be obtained by reaction of 2-methylpyridine 1 with formaldehyde 2 and subsequent dehydration .
The compound can also be obtained from acrylonitrile by reacting with ethyne in the presence of an organocobalt catalyst:
In 1887 Albert Ladenburg synthesized 2-vinylpyridine for the first time, but did not describe a precise reaction route.
properties
2-vinylpyridine is a light red-brown liquid with a pungent odor that is sparingly soluble in water.
use
2-vinylpyridine is used in the manufacture of poly (2-vinylpyridine) by free radical polymerization as well as other polymers . It is also used to improve the effectiveness of protective polymer layers on metals and is also used as the starting material for a plastic that is used in the manufacture of pharmaceuticals and bio-compounds.
safety instructions
The vapors of 2-vinylpyridine can form an explosive mixture with air ( flash point 47 ° C, ignition temperature 440 ° C).
Individual evidence
- ↑ a b c d e f g h i j k l Entry on 2-vinylpyridine in the GESTIS substance database of the IFA , accessed on November 22, 2018(JavaScript required) .
- ↑ a b data sheet 2-vinylpyridines, 97%, stab. with 0.1% 4-tert-butylcatechol from AlfaAesar, accessed on November 22, 2018 ( PDF )(JavaScript required) .
- ↑ David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 568 ( limited preview in Google Book search).
- ↑ Data sheet 2-vinylpyridine, 97% from Sigma-Aldrich , accessed on November 22, 2018 ( PDF ).
- ^ Heinrich Dittmar, Manfred Drach, Ralf Vosskamp, Martin E. Trenkel, Reinhold Gutser, Günter Steffens: Fertilizers, 2. Types. In: Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, 2009, ISBN 978-3-527-30673-2 .
- ↑ W. Schulz, H. Pracejus, G. Oehme: New three-step synthesis of 2-vinylpyridine starting from acrylonitrile. In: Journal of Molecular Catalysis. 66, 1991, p. 29, doi : 10.1016 / 0304-5102 (91) 85018-W .
- ↑ A. Ladenburg: About the styrene of the pyridine series. In: Reports of the German Chemical Society. 20, 1887, p. 1643, doi : 10.1002 / cber.188702001371 .
- ↑ Google Patents: US2716118A - Process of producing vinylpyridines - Google Patents , accessed November 22, 2018.
- ↑ Christoph Juerg Klein: On the polymerization of 2-vinylpyridine . Aku-Fotodruck, 1971, p. 12 ( limited preview in Google Book search).
- ↑ Entry on 2-vinylpyridine in the Hazardous Substances Data Bank , accessed November 22, 2018.