Bis (2-ethylhexyl) sebacate
Structural formula | ||||||||||||||||
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Mixture of three isomers Structural formula without specifying the stereochemistry |
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General | ||||||||||||||||
Surname | Bis (2-ethylhexyl) sebacate | |||||||||||||||
other names |
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Molecular formula | C 26 H 50 O 4 | |||||||||||||||
Brief description |
colorless and odorless liquid |
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External identifiers / databases | ||||||||||||||||
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properties | ||||||||||||||||
Molar mass | 426.68 g mol −1 | |||||||||||||||
Physical state |
liquid |
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density |
0.91 g cm −3 |
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Melting point |
−55 ° C |
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boiling point |
256 ° C (6.66 hPa) |
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Vapor pressure |
<0.01 hPa (20 ° C) |
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solubility | ||||||||||||||||
Refractive index |
1,450 (20 ° C) |
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safety instructions | ||||||||||||||||
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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 |
Bis (2-ethylhexyl) sebacate is a mixture of three isomeric chemical compounds from the group of carboxylic acid esters , all of which have the empirical formula C 26 H 50 O 4 .
Extraction and presentation
Bis (2-ethylhexyl) sebacate, by esterification of sebacic acid with 2-ethylhexyl alcohol of a in the presence of acid catalyst , or alternatively, be recovered at high pressure.
Isomerism
Bis (2-ethylhexyl) sebacate has a stereocenter at each branch point of the two 2-ethylhexyl radicals, so there are three stereoisomers :
- ( R , R ) -Bis (2-ethylhexyl) sebacate,
- ( S , S ) -Bis (2-ethylhexyl) sebacate and
- meso -bis (2-ethylhexyl) sebacate.
In industry, bis (2-ethylhexyl) sebacate is produced practically exclusively as a mixture of these three stereoisomers. As a rule, such stereoisomers have different physiological and thus also toxicological properties.
properties
Bis (2-ethylhexyl) sebacate is a flammable, hardly inflammable, colorless and odorless liquid that is practically insoluble in water.
use
Bis (2-ethylhexyl) sebacate is used as a plasticizer ( e.g. for explosives) and a lubricant. It is an important intermediate in the organic synthesis of pharmaceuticals, agrochemicals and dyes. It can also be used to generate stable aerosols , which are particularly suitable for the acceptance and monitoring of clean room systems.
Individual evidence
- ↑ a b c d e f g h i j Entry on bis (2-ethylhexyl) sebacate in the GESTIS substance database of the IFA , accessed on December 31, 2016(JavaScript required) .
- ^ William M. Haynes: CRC Handbook of Chemistry and Physics, 94th Edition . CRC Press, 2016, ISBN 978-1-4665-7115-0 , pp. 54 ( limited preview in Google Book search).
- ↑ Data sheet bis (2-ethylhexyl) sebacate, Selectophore from Sigma-Aldrich , accessed on December 31, 2016 ( PDF ).
- ↑ Entry on bis (2-ethylhexyl) sebacate in the Hazardous Substances Data Bank , accessed on December 31, 2016.
- ↑ Ram C. Narayan, Giridhar Madras: Kinetics of non-catalytic synthesis of bis (2-ethylhexyl) sebacate at high pressures. In: React. Chem. Eng. 2017, doi : 10.1039 / C6RE00162A .
- ^ EJ Ariëns, Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology , European Journal of Clinical Pharmacology 26 (1984) 663-668, doi : 10.1007 / BF00541922 .
- ↑ Peter Kurzweil: Chemistry basics, structural knowledge, applications and experiments . Springer-Verlag, 2015, ISBN 978-3-658-08660-2 , pp. 273 ( limited preview in Google Book search).
- ↑ Data sheet bis (2-ethylhexyl) sebacate, 95% from AlfaAesar, accessed on December 31, 2016 ( PDF )(JavaScript required) .
- ^ Topas GmbH: Di-Ethyl-Hexyl-Sebacat DEHS