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Trithioacetone (2,2,4,4,6,6-hexamethyl-1,3,5-trithiane) is an
organic chemical In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The st ...
with
formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...
. Its
covalent A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atoms ...
structure is , that is, a six-membered ring of alternating
carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...
and
sulfur Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula ...
atoms, with two
methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...
s attached to each carbon. It can be viewed as a derivative of 1,3,5-trithiane, with methyl-group
substituent A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and ''functional group'', as well as ''side ...
s for all of the hydrogen atoms in that parent structure. The compound Trithioacetone is a stable
cyclic Cycle, cycles, or cyclic may refer to: Anthropology and social sciences * Cyclic history, a theory of history * Cyclical theory, a theory of American political history associated with Arthur Schlesinger, Sr. * Social cycle, various cycles in soc ...
trimer of
thioacetone Thioacetone is an organosulfur compound belonging to the -thione group called thioketones, with a chemical formula (CH3)2CS. It is an unstable orange or brown substance that can be isolated only at low temperatures. Above , thioacetone readily co ...
(propane-2-thione), which by itself is an unstable compound. In contrast, the analogous
trioxane Trioxane refers to any of three isomeric organic compounds composed of a six-membered ring with three carbon atoms and three oxygen atoms, having the molecular formula C3H6O3. The three isomers are: * 1,2,3-trioxane, a hypothetical compound rela ...
compound, 2,2,4,4,6,6-hexamethyl-1,3,5-trioxane ( Triacetone), with
oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...
atoms in place of the sulfur atoms, seems to be unstable, while its corresponding monomer
acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...
(2-propanone) is stable.


Synthesis

Trithioacetone was first made in 1889 by Baumann and Fromm, by reaction of
hydrogen sulfide Hydrogen sulfide is a chemical compound with the formula . It is a colorless chalcogen-hydride gas, and is poisonous, corrosive, and flammable, with trace amounts in ambient atmosphere having a characteristic foul odor of rotten eggs. The unde ...
with acetone. In the presence of an acidified catalyst at 25 °C, one obtains a product that is 60–70% trithioacetone, 30–40% of 2,2-propanedithiol, and small amounts of two isomeric impurities, 3,3,5,5,6,6-hexamethyl 1,2,4-trithiane and 4-mercapto-2,2,4,6,6-pentamethyl-1,3-dithiane. The product can also be obtained by
pyrolysis The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''py ...
of allyl isopropyl sulfide.


Reactions

Pyrolysis of trithioacetone at 500–650 °C and 5–20 mm of Hg gives thioacetone, that can be collected by a cold trap at −78 °C.


Uses

Trithioacetone is found in some
flavoring agent A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of the gustat ...
s. Its
FEMA The Federal Emergency Management Agency (FEMA) is an agency of the United States Department of Homeland Security (DHS), initially created under President Jimmy Carter by Presidential Reorganization Plan No. 3 of 1978 and implemented by two Exec ...
number is 3475.


Toxicity

The LD50 (oral) in mice is 2.4 g/kg.


See also

* 2,4,6-trimethyl-1,3,5-trithiane *
Hexamethylcyclotrisiloxane Hexamethylcyclotrisiloxane, also known as D3 and D3, is the organosilicon compound with the formula . It is a colorless or white volatile solid. It finds limited use in organic chemistry. The larger tetrameric and pentameric siloxanes, respective ...
, an analog with a
silicon Silicon is a chemical element with the symbol Si and atomic number 14. It is a hard, brittle crystalline solid with a blue-grey metallic luster, and is a tetravalent metalloid and semiconductor. It is a member of group 14 in the periodic tab ...
-oxygen ring instead of a carbon-sulfur one. * Hexamethylcyclotrisilazane, with a silicon-
nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...
ring. * 2,2,4,4,6,6-hexamethyl-1,3,5-triselena-2,4,6-tristannacyclohexane, with a
tin Tin is a chemical element with the symbol Sn (from la, stannum) and atomic number 50. Tin is a silvery-coloured metal. Tin is soft enough to be cut with little force and a bar of tin can be bent by hand with little effort. When bent, t ...
-
selenium Selenium is a chemical element with the symbol Se and atomic number 34. It is a nonmetal (more rarely considered a metalloid) with properties that are intermediate between the elements above and below in the periodic table, sulfur and tellurium, ...
ring.


References

Stuart D. Brewer and Charles P. Haber (1948): "Alkylsilazanes and Some Related Compounds". ''Journal of the American Chemical Society'', volume 70, issue 11, pages 3888–3891. B. M. Mikhova (2008), "NMR Data for Carbon-13 – C6H18Se3Sn3" in ''Landolt-Börnstein – Group III Condensed Matter'', volume 35 ''Nuclear Magnetic Resonance Data'', subvolume D5, ''Organometallic Compounds''. Martin Dräger, Axel Blecher, Hans-Jürgen Jacobsen, Bernt Krebs (1978): "Molekül- und kristallstruktur von hexamethylcyclo-tristannaselenan ". ''Journal of Organometallic Chemistry'', volume 161, issue 3, pages 319–325. EUR-Lex (2012):
Table entry 15.009: Trithioacetone
. In ''EU Regulation No. 872/2012'', Document 32012R0872, ''Official Journal of the EU – Series L'', volume 267, pages 1–161. Horst Bohme, Hans Pfeifer, and Erich Schneider (1942): "Dimeric thioketones". ''Berichte der Deutschen Chemischen Gesellschaft'', volume 75B, issue 7, pages 900–909. Note: This early report mistakes the trimer for the monomer. TCI America (2020):
Product H1278: 2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane
. Online catalog page, accessed on 2020-01-01. R. D. Lipscomb and W. H. Sharkey (1970): "Characterization and polymerization of thioacetone". ''Journal of Polymer Science – Part A: Polymer Chemistry'', volume 8, issue 8, pages 2187–2196. William J. Bailey and Hilda Chu (1965): "Synthesis of polythioacetone". ''ACS Polymer Preprints'', volume 6, pages=145–155 William H. Sharkey (1979): "Polymerization through the carbon-sulfur double bond". ''Polymerization'', series ''Advances in Polymer Science'', volume 17, pages 73–103. G. Ohloff and I. Flament (1979): "The Role of Heteroatomic Substances in the Aroma Compounds of Foodstuffs". In ''Fortschritte der Chemie Organischer Naturstoffe'' (''Progress in the Chemistry of Organic Natural Products''), volume 36, pages 231–283. World Health Organization (1999):
Trithioacetone
. Online data sheet in the ''Evaluation of the Joint FAO/WHO Expert Committee on Food Additives (JECFA)''. Accessedd on 2020-01-02.
David S. Breslow David S. Breslow (August 13, 1916May 26, 1995) was an American industrial chemist best known for his work on polymers. Early life and education Breslow was born on August 13, 1916, and raised in Queens, New York. He developed an early interest ...
, Herman Skolnik (2009): ''Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles'', Part 2; page 712. Volume 68 of ''Chemistry of Heterocyclic Compounds''. Trithioacetone
. Online chemical data sheet, accessed on 2020-01-01. NCBI PubChem (2010):
2,2,4,4,6,6-Hexamethyl-1,3,5-trithiane
. Online chemical data sheet, accessed on 2020-01-01. E. J. Moran, O. D. Easterday, and B. L. Oser (1980): "Acute oral toxicity of selected flavor chemicals". ''Drug and Chemical Toxicology'', volume 3, issue 3, pages 249–258. {{doi, 10.3109/01480548009002221 Sulfur heterocycles