Di- tert-butyl peroxide

Di- tert-butyl peroxide
Are common
Systematic name	Di- tert- β- butyl peroxide
Chem. formula	C₈H₁₈O₂
Rat formula	C 8 H 18 O 2
Physical properties
condition	colorless liquid
Molar mass	146.23 g / mol
Density	0.796 g / cm³
Thermal properties
T. melt.	-40 ℃
T. bale.	109 ℃
Like heat resistant.	1.965 J / (mol · K)
Classification
CAS Number
PubChem
ChemSpider
EINECS Number	203-733-6
Smiles
	CC (C) (C) OOC (C) (C) C
Inchi
	1S / C8H18O2 / c1-7 (2,3) 9-10-8 (4,5) 6 / h1-6H3
	Data is provided for standard conditions (25 ℃, 100 kPa) , unless otherwise indicated.

Di- tert-butyl peroxide ( tert-butyl peroxide) is an organic compound belonging to symmetric organic peroxides .

Content

Physical and chemical properties

Di- tert-butyl peroxide is a colorless liquid capable of distillation at atmospheric pressure. Slightly soluble in water (0.9%). From strong friction and shock it can explode. Relatively stable during storage.

During thermolysis, it breaks down according to the OO bond by the homolytic mechanism:

{\mathsf {(CH_{3})_{3}COOC(CH_{3})_{3}\rightarrow 2(CH_{3})_{3}CO\cdot }}

{\ displaystyle {\ mathsf {(CH_ {3}) _ {3} COOC (CH_ {3}) _ {3} \ rightarrow 2 (CH_ {3}) _ {3} CO \ cdot}}}

The resulting radicals tear off the hydrogen atom from other peroxide and solvent molecules, recombine with other radicals, etc., leading to a complex mixture of products, among which tert- butanol , acetone and ethane predominate.

It exhibits oxidizing properties, in particular, it oxidizes potassium iodide in acetic acid to iodine .

Receiving and applying

Industrial synthesis of di- tert-butyl peroxide consists in the reaction of tert- butanol with 50% hydrogen peroxide in the presence of sulfuric acid , separation from other reaction products by washing and drying. Reaction Scheme:

{\mathsf {2(CH_{3})_{3}COH+H_{2}O_{2}{\xrightarrow[{20-21^{o}C}]{H_{2}SO_{4}}}(CH_{3})_{3}COOC(CH_{3})_{3}+2H_{2}O}}

{\ displaystyle {\ mathsf {2 (CH_ {3}) _ {3} COH + H_ {2} O_ {2} {\ xrightarrow [{20-21 ^ {o} C}] {H_ {2} SO_ { 4}}} (CH_ {3}) _ {3} COOC (CH_ {3}) _ {3} + 2H_ {2} O}}}

Under laboratory conditions, the di- tert-butyl peroxide is purified by distillation under reduced pressure.

Di- tert-butyl peroxide (trademarks Trigonox B, Luperox DI) is used in industry as an initiator of radical polymerization and telomerization , as well as as a curing agent.

Security Measures

When exposed to the skin, di- tert-butyl peroxide causes dermatitis that is difficult to treat. When ingested, it acts on the central nervous system .

Di- tert-butyl peroxide is a fire and explosive compound. When working, its contact with transition metals and their salts catalyzing the decomposition of peroxides should be avoided. During bottling, di- tert-butyl peroxide is collected in sand, taken out and burned. When ignited, it is not extinguished with water, since di- tert-butyl peroxide floats and continues to burn, but with sand, carbon dioxide and powder fire extinguishers.

Literature

A.I. Rakhimov. Chemistry and technology of organic peroxide compounds. - M .: "Chemistry", 1979. - 392 p. - 2,900 copies.
E.J.E. Hawkins. Organic peroxides, their preparation and reactions. - M., Leningrad: “Chemistry”, 1961. - 536 p. - 4,000 copies.