Triacetone triperoxide

Acetone peroxide

Cyclic dimer and trimer examples
Names
IUPAC names 3,3-Dimethyl-1,2-dioxacyclopropane (monomer) 3,3,6,6-Tetramethyl-1,2,4,5-tetraoxane (dimer) 3,3,6,6,9,9-Hexamethyl-1,2,4,5,7,8-hexaoxacyclononane (trimer) 3,3,6,6,9,9,12,12-Octamethyl-1,2,4,5,7,8,10,11-octaoxacyclododecane (tetramer)
Other names Triacetone triperoxide Peroxyacetone Mother of Satan
Identifiers
CAS Number	17088-37-8 N
3D model (JSmol)	dimer: Interactive image trimer: Interactive image
ChemSpider	3582942 Y
E number	E929 (glazing agents, ...)
PubChem CID	4380970
InChI InChI=1S/C9H18O6/c1-7(2)10-12-8(3,4)14-15-9(5,6)13-11-7/h1-6H3 Y Key: ZTLXICJMNFREPA-UHFFFAOYSA-N Y InChI=1/C9H18O6/c1-7(2)10-12-8(3,4)14-15-9(5,6)13-11-7/h1-6H3 Key: ZTLXICJMNFREPA-UHFFFAOYAS
SMILES dimer: CC1(C)OOC(C)(C)OO1 trimer: CC1(C)OOC(C)(C)OOC(C)(C)OO1
Properties
Chemical formula	C6H12O4 (dimer) C9H18O6 (trimer) C12H24O8 (tetramer)
Molar mass	148.157 g/mol (dimer) 222.24 g/mol (trimer)
Appearance	White crystalline solid
Melting point	131.5 to 133 °C (dimer) 91 °C (trimer)
Boiling point	97 to 160 °C (207 to 320 °F; 370 to 433 K)
Solubility in water	Insoluble
Hazards
Main hazards	Explosive
NFPA 704	4
Explosive data
Shock sensitivity	High / moderate when wet
Friction sensitivity	High / moderate when wet
Detonation velocity	5300 m/s at maximum density (1.18 g/cm3), about 2500 - 3000 m/s near 0.5 g/cm3 17,384 ft/s 3.29 miles per second
RE factor	0.83
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Acetone peroxide is an organic peroxide and a primary high explosive. It is produced by the oxidation of acetone to yield a mixture of linear monomer and cyclic dimer, trimer, and tetramer forms. The trimer is known as triacetone triperoxide (TATP) or tri-cyclic acetone peroxide (TCAP). Acetone peroxide takes the form of a white crystalline powder with a distinctive bleach-like odor (when impure) and can explode if subjected to heat, friction, static electricity, strong UV radiation or shock. As a non-nitrogenous explosive, TATP has historically been more difficult to detect, and it has been used as an explosive in several terrorist attacks since 2001.

Acetone peroxide (specifically, triacetone triperoxide) was discovered in 1895 by Richard Wolffenstein. Wolffenstein combined acetone and hydrogen peroxide, and then he allowed the mixture to stand for a week at room temperature, during which time a small quantity of crystals precipitated, which had a melting point of 97 °C.

In 1899 Adolf von Baeyer and Victor Villiger described the first synthesis of the dimer and described use of acids for the synthesis of both peroxides. Baeyer and Villiger prepared the dimer by combining potassium persulfate in diethyl ether with acetone, under cooling. After separating the ether layer, the product was purified and found to melt at 132–133 °C. They found that the trimer could be prepared by adding hydrochloric acid to a chilled mixture of acetone and hydrogen peroxide. By using the depression of freezing points to determine the molecular weights of the compounds, they also determined that the form of acetone peroxide that they had prepared via potassium persulfate was a dimer, whereas the acetone peroxide that had been prepared via hydrochloric acid was a trimer, like Wolffenstein's compound.