Bis (2-ethylhexyl) sebacate

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Structural formula
Structural formula of bis (2-ethylhexyl) sebacate
Mixture of three isomers
Structural formula without specifying the stereochemistry
General
Surname Bis (2-ethylhexyl) sebacate
other names
  • Sebacic acid bis (2-ethylhexyl ester)
  • Decanedioic acid bis (2-ethylhexyl ester)
  • Dioctyl sebacate
  • Di-ethyl hexyl sebacate
  • Di-2-ethylhexyl sebacate
Molecular formula C 26 H 50 O 4
Brief description

colorless and odorless liquid

External identifiers / databases
CAS number 122-62-3
EC number 204-558-8
ECHA InfoCard 100.004.145
PubChem 31218
Wikidata Q4387284
properties
Molar mass 426.68 g mol −1
Physical state

liquid

density

0.91 g cm −3

Melting point

−55 ° C

boiling point

256 ° C (6.66 hPa)

Vapor pressure

<0.01 hPa (20 ° C)

solubility
Refractive index

1,450 (20 ° C)

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
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

The three stereoisomers of bis (2-ethylhexyl) sebacate.

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

  1. ↑ 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) .
  2. ^ 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).
  3. ↑ Data sheet bis (2-ethylhexyl) sebacate, Selectophore from Sigma-Aldrich , accessed on December 31, 2016 ( PDF ).
  4. ↑ Entry on bis (2-ethylhexyl) sebacate in the Hazardous Substances Data Bank , accessed on December 31, 2016.
  5. ↑ 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 .
  6. ^ 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 .
  7. ↑ 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).
  8. ↑ Data sheet bis (2-ethylhexyl) sebacate, 95% from AlfaAesar, accessed on December 31, 2016 ( PDF )(JavaScript required) .
  9. ^ Topas GmbH: Di-Ethyl-Hexyl-Sebacat DEHS