tert -butyl hydroperoxide

Structural formula
General
Surname	tert -butyl hydroperoxide
other names	1,1-dimethylethyl hydroperoxide; TBHP; 2-methylpropane-2-peroxol ( IUPAC ) ;
Molecular formula	C 4 H 10 O 2
Brief description	colorless, pungent smelling liquid
External identifiers / databases
EC number	200-915-7
ECHA InfoCard	100,000,833
PubChem	6410
Wikidata	Q286326
properties
Molar mass	90.12 g mol −1
Physical state	liquid
density	0.90 g cm −3
Melting point	−8 ° C
boiling point	> 75 ° C (decomposition); 35 ° C (27 hPa);
Vapor pressure	23 h Pa (36 ° C)
solubility	soluble in water (100–150 g · l −1 at 20 ° C)
Refractive index	1.4015 (20 ° C)
safety instructions
H and P phrases	H: 226-242-302-311-330-314-317-341-411
	P: 210-220-280-301 + 330 + 331-303 + 361 + 353-305 + 351 + 338-310
Toxicological data	370 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

tert -Butyl hydroperoxide (TBHP) is an organic chemical compound that belongs to the group of hydroperoxides and occurs in the form of a colorless, pungent smelling liquid. TBHP is the simplest tertiary hydroperoxide.

Extraction and presentation

Tert-butyl hydroperoxide can be obtained by reacting tert-butyl alcohol with hydrogen peroxide in an acidic solution ( sulfuric acid ).

properties

tert -Butyl hydroperoxide is a colorless, flammable, pungent smelling liquid. Furthermore, TBHP is a strong oxidizing agent .

use

As an organic peroxide, tert-butyl hydroperoxide has many uses. So it can be used as:

as starters (initiators) for radical polymerization - production of bulk plastics
for networking and modification of plastics
for curing unsaturated polyester resins
as a disinfectant - e.g. B. Peroxyacetic acid formulations in food technology
as an oxidizing agent (e.g. for phenols and peroxide complexes)
in wastewater treatment
in Sharpless epoxidation (epoxidation of primary or secondary allyl alcohols)
in the Halcon process for the production of organic compounds (e.g. propylene oxide , ethylene glycol ).

safety instructions

Vapors of tert-butyl hydroperoxide can form explosive mixtures with air at temperatures above the flash point (26 ° C). tert -Butyl hydroperoxide is the only substance that has a maximum value of 4 in all three categories in the NFPA-704 system .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on tert-butyl hydroperoxide in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ ^a ^b ^c ^d ^e Entry on tert-butyl hydroperoxide. In: Römpp Online . Georg Thieme Verlag, accessed on January 27, 2017.
↑ OECD: RISK ASSESSMENT TERTIARY BUTYL HYDROPEROXIDE (TBHP) (PDF; 372 kB), Final report, 11 October 2006.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-80.
↑ Entry on tert-butyl hydroperoxide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on June 17, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Entry on tert-butyl hydroperoxide in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 31, 2018 or earlier.
↑ Sharpless epoxidation. ( Memento from November 6, 2011 in the Internet Archive ) In: Organic Chemistry Compact, CDCH Verlag, Hamburg 2004.
↑ data sheet tert. -Butyl Hydroperoxide at Cameochemicals, accessed October 31, 2012.

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

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

[oecd-3] OECD: RISK ASSESSMENT TERTIARY BUTYL HYDROPEROXIDE (TBHP) (PDF; 372 kB), Final report, 11 October 2006.

[CRC90_3_80-4] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-80.

[CLP_100.000.833-5] Entry on tert-butyl hydroperoxide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on June 17, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .

[ChemIDplus-6] Entry on tert-butyl hydroperoxide in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 31, 2018 or earlier.

[7] Sharpless epoxidation. ( Memento from November 6, 2011 in the Internet Archive ) In: Organic Chemistry Compact, CDCH Verlag, Hamburg 2004.

[8] ta sheet tert. -Butyl Hydroperoxide at Cameochemicals, accessed October 31, 2012.