Di- tert-butyl peroxide

Structural formula
General
Surname	Di- tert-butyl peroxide
other names	DTBP; Bis (1,1-dimethylethyl) peroxide; Ditertiary butyl peroxide;
Molecular formula	C 8 H 18 O 2
Brief description	Highly flammable, volatile, colorless to yellowish liquid with an ethereal odor
External identifiers / databases
EC number	203-733-6
ECHA InfoCard	100.003.395
PubChem	8033
Wikidata	Q413043
properties
Molar mass	146.23 g mol −1
Physical state	liquid
density	0.79 g cm −3
Melting point	−40 ° C
boiling point	80 ° C (decomposition); 111 ° C;
Vapor pressure	35 mbar (20 ° C)
solubility	very heavy in water (43–63 mg l −1 at 20 ° C)
Refractive index	1.3891 (20 ° C)
safety instructions
H and P phrases	H: 225-242-341-412
	P: 210-220-273-280-410-411 + 235
Toxicological data	> 25000 mg kg −1 ( LD 50 , rat , oral )
	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

Di- tert -butyl peroxide is a chemical compound from the group of organic peroxides .

Extraction and presentation

Di- tert -butyl peroxide can be obtained by reacting tert-butyl hydroperoxide with tert-butyl alcohol .

properties

Di- tert -butyl peroxide is a highly flammable, volatile, colorless to yellowish liquid with an ethereal odor. The vapors of di- tert-butyl peroxide can form an explosive mixture with air ( flash point 4 ° C).

The compound decomposes when heated above 80 ° C. Here are initially formed tert -butoxy radical , which to acetone can react further and methyl radicals. If this decomposition takes place in a solution, the resulting methyl and tert- butoxy radicals react with the solvent , mostly removing a hydrogen atom from it (so-called radical hydrogen abstraction). The resulting solvent radicals can recombine, as a result of which corresponding, substituted compounds can be produced (e.g. ethylenediamines substituted from tertiary amines , 1,2- glycols from primary and secondary alcohols ).

use

Di- tert -butyl peroxide is used as an initiator for the polymerization of olefins and as a crosslinking agent for silicone rubber . Furthermore, di- tert-butyl peroxide is used as an initiator for the production of so-called (meth) acrylate resins . This is a solution polymerization process . Typical applications of such binders would be high quality clearcoats in the automotive sector.

Risk assessment

Di-tert-butyl peroxide was included in the EU's ongoing action plan ( CoRAP ) in 2013 in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation . The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. Ingestion of di-tert-butyl peroxide was caused by concerns about its classification as a CMR substance, consumer use , high (aggregated) tonnage and widespread use. The re-evaluation has been running since 2016 and is carried out by the Netherlands .

literature

Eduardo Lissi: Photolysis of Di-tert-butyl Peroxide in Solution . In: Canadian Journal of Chemistry . 52 (13), 1974, pp. 2491-2492, doi : 10.1139 / v74-363 .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on di-tert-butyl peroxide in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ ^a ^b ^c ^d Entry on di-tert-butyl peroxide. In: Römpp Online . Georg Thieme Verlag, accessed on January 27, 2017.
↑ Data sheet tert-butyl peroxide from Sigma-Aldrich , accessed on March 24, 2011 ( PDF ).
↑ Entry on di-tert-butyl peroxide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ K. Schwetlick, J. Jentzsch, R. Karl, D. Wolter: Reactions with tert. -Butoxy radicals. III. Dehydrodimerizations with di- tert. -butyl peroxide . In: Journal für Praktische Chemie , 1964 , 25 (1-2), pp. 95-100; doi : 10.1002 / prac.19640250112 .
↑ Ulrich Poth: Synthetic binders for coating systems . Vincentz Network, Hannover 2016, ISBN 978-3-86630-611-0 .
↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Di-tert-butyl peroxide , accessed on March 26, 2019.Template: CoRAP status / 2016

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on di-tert-butyl peroxide in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[Roempp-2] Entry on di-tert-butyl peroxide. In: Römpp Online . Georg Thieme Verlag, accessed on January 27, 2017.

[Sigma-3] Data sheet tert-butyl peroxide from Sigma-Aldrich , accessed on March 24, 2011 ( PDF ).

[CLP_100.003.395-4] Entry on di-tert-butyl peroxide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[5] K. Schwetlick, J. Jentzsch, R. Karl, D. Wolter: Reactions with tert. -Butoxy radicals. III. Dehydrodimerizations with di- tert. -butyl peroxide . In: Journal für Praktische Chemie , 1964 , 25 (1-2), pp. 95-100; doi : 10.1002 / prac.19640250112 .

[6] Ulrich Poth: Synthetic binders for coating systems . Vincentz Network, Hannover 2016, ISBN 978-3-86630-611-0 .

[7] Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Di-tert-butyl peroxide , accessed on March 26, 2019.Template: CoRAP status / 2016