Octachloropropane or perchloropropane is the

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

with

elemental formula Amino acid-based formula is a type of infant milk formula made from individual amino acids. It is hypoallergenic and intended for infants suffering from severe allergy to milk and various gastrointestinal conditions, such as food protein-induce ...

and

structural formula The structural formula of a chemical compound is a graphic representation of the molecular structure (determined by structural chemistry methods), showing how the atoms are connected to one another. The chemical bonding within the molecule is al ...

. Its molecule has a simple chain of three

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

atoms connected by

single bond In chemistry, a single bond is a chemical bond between two atoms involving two valence electrons. That is, the atoms share one pair of electrons where the bond forms. Therefore, a single bond is a type of covalent bond. When shared, each of th ...

s, with

chlorine Chlorine is a chemical element; it has Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between ...

atoms filling their remaining bonds. It is a

chlorocarbon Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds that contain one or more carbon–chlorine bonds. The chloroalkane class (alkanes with one or more hydrogens substituted ...

, specifically the third simplest perchloroalkane (after

carbon tetrachloride Carbon tetrachloride, also known by many other names (such as carbon tet for short and tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC), is a chemical compound with the chemical formula CCl4. It is a n ...

and

hexachloroethane Hexachloroethane (perchloroethane) is an organochlorine compound with the chemical formula . Its structure is . It is a white or colorless solid at room temperature with a camphor-like odor. It has been used by the military in smoke compositions, ...

). It can be described as a derivative of

propane Propane () is a three-carbon chain alkane with the molecular formula . It is a gas at standard temperature and pressure, but becomes liquid when compressed for transportation and storage. A by-product of natural gas processing and petroleum ref ...

, with all

hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...

atoms replaced by chlorine. Octachloropropane is a clear white crystalline solid at room temperature, with

hexagonal In geometry, a hexagon (from Greek , , meaning "six", and , , meaning "corner, angle") is a six-sided polygon. The total of the internal angles of any simple (non-self-intersecting) hexagon is 720°. Regular hexagon A regular hexagon is d ...

crystal structure. It is easily deformed by mechanical stress, without losing its crystal structure, like a

metal A metal () is a material that, when polished or fractured, shows a lustrous appearance, and conducts electrical resistivity and conductivity, electricity and thermal conductivity, heat relatively well. These properties are all associated wit ...

History

Synthesis and characterization of octachloropropane was reported in 1875 by Krafft and Merz. Its remarkable crystal growth and deformation properties were noted by McCrone in 1949. Its use as a model for crystal deformation of minerals was pioneered by Win D. Means, Marc W. Jessel and others in the 1980s.

Production

Octachloropropane can be obtained by reacting partially chlorinated propane with

iodine trichloride Iodine trichloride is an interhalogen compound of iodine and chlorine. It is bright yellow but upon time and exposure to light it turns red due to the presence of elemental iodine. In the solid state is present as a planar dimer I2Cl6, with two ...

(as in the original synthesis by Krafft and Merz), or with chlorine at high pressure or with activation by light. The temperature must be close to but below 200 °C, since at higher temperatures further reaction with chlorine gives

and

instead.

Chemistry

Octachloropropane treated with

aluminium Aluminium (or aluminum in North American English) is a chemical element; it has chemical symbol, symbol Al and atomic number 13. It has a density lower than that of other common metals, about one-third that of steel. Aluminium has ...

diethyl ether Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...

affords several unsaturated perchlorocarbons, by way of hexachloropropene (, ). For instance, : + 2/3 2/3 + : 2 + 4/3 4/3 + (three

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...

s) : 2 + 2 2 + (two

s) The products were identified as : α-: colorless, m. p. 148 °C. : β-: red, m. p. 155 °C with conjectured structures or , and : α-: b. p. 105-110 °C at 0.1

torr The torr (symbol: Torr) is a Pressure#Units, unit of pressure based on an absolute scale, defined as exactly of a standard atmosphere (unit), atmosphere (101325 Pa). Thus one torr is exactly (≈ ). Historically, one torr was intended to be ...

. : β-: m. p. 71 °C. : γ-: m. p. 183 °C. which were claimed to be ''cis''/''trans'' isomers and

atropisomers Atropisomers are stereoisomers arising because of hindered rotation about a single bond, where energy differences due to steric strain or other contributors create a barrier to rotation that is high enough to allow for isolation of individual ro ...

of ( octachloro(1,3,5)hexatriene).

Applications

Crystalline plasticity model

Octacholopropane is used by

geologist A geologist is a scientist who studies the structure, composition, and History of Earth, history of Earth. Geologists incorporate techniques from physics, chemistry, biology, mathematics, and geography to perform research in the Field research, ...

s and

metallurgists Metallurgy is a domain of materials science and engineering that studies the physical and chemical behavior of metallic elements, their inter-metallic compounds, and their mixtures, which are known as alloys. Metallurgy encompasses both the ...

as a model to study the plastic deformation of crystalline minerals and rocks under stress. The large individual crystalline grains (0.1-1.0 mm diameter) are distinguishable with a polarized light microscope at moderate magnification, and generally retain their size and approximate aspect ratio as the material undergoes

shear strain In mechanics, strain is defined as relative deformation, compared to a position configuration. Different equivalent choices may be made for the expression of a strain field depending on whether it is defined with respect to the initial or the ...

. The grains will spontaneously arise from the quenched solid, in minutes or hours, even at room temperature. The material's flow driven by stress can be followed by embedding in it small amounts of fine inert particles, such as

grit Grit, Grits, or Gritty may refer to: Food * Grit (grain), bran, chaff, mill-dust or coarse oatmeal * Grits, a corn-based food common in the Southern United States Minerals * Grit, winter pavement-treatment minerals deployed in grit bins * G ...

1000 abrasives; the particles apparently do not affect the grain evolution and deformation.

Camphor Camphor () is a waxy, colorless solid with a strong aroma. It is classified as a terpenoid and a cyclic ketone. It is found in the wood of the camphor laurel (''Cinnamomum camphora''), a large evergreen tree found in East Asia; and in the kapu ...

(with

rhombohedral In geometry, a rhombohedron (also called a rhombic hexahedron or, inaccurately, a rhomboid) is a special case of a parallelepiped in which all six faces are congruent rhombus, rhombi. It can be used to define the rhombohedral lattice system, a Ho ...

crystal structure) was previously proposed for this use.

Metal separation

Octachlorpropane reacts with

niobium pentoxide Niobium pentoxide is the inorganic compound with the formula Nb2 O5. A colorless, insoluble, and fairly unreactive solid, it is the most widespread precursor for other compounds and materials containing niobium. It is predominantly used in alloyi ...

and tantalum pentoxide at atmospheric pressure yielding the corresponding chlorides. It also reacts with

titanium dioxide Titanium dioxide, also known as titanium(IV) oxide or titania , is the inorganic compound derived from titanium with the chemical formula . When used as a pigment, it is called titanium white, Pigment White 6 (PW6), or Colour Index Internationa ...

, if the other two oxides are present. This reaction, followed with distillation of the

titanium tetrachloride Titanium tetrachloride is the inorganic compound with the formula . It is an important intermediate in the production of titanium metal and the pigment titanium dioxide. is a volatile liquid. Upon contact with humid air, it forms thick clouds o ...

at about 225 °C, could be an effective way to remove from mixtures of those oxides.

Pesticide

Octachloropropane has been commercialized as a snail killer with the brand name HRS-1622, although it was not found to be very effective. Octachloropropane was found to be highly toxic to larvae of the

housefly The housefly (''Musca domestica'') is a fly of the suborder Cyclorrhapha. It possibly originated in the Middle East, and Cosmopolitan distribution, spread around the world as a commensal of humans. Adults are gray to black, with four dark, lo ...

, with an efficiency comparable to decachlorobutane and

hexachlorobenzene Hexachlorobenzene, or perchlorobenzene, is an aryl chloride and a six-substituted chlorobenzene with the molecular formula C6Cl6. It is a fungicide formerly used as a seed treatment, especially on wheat to control the fungal disease bunt. Its u ...

(BHC). Unlike the latter, it is somewhat volatile and thus effective even without physical contact with the solid.

Environmental concerns

Octachloropropane was detected as a relatively minor item among dozens of highly chlorinated and perchlorinated hydrocarbons present as contaminants in the carbon tetrachloride produced from

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

by a plant in

China China, officially the People's Republic of China (PRC), is a country in East Asia. With population of China, a population exceeding 1.4 billion, it is the list of countries by population (United Nations), second-most populous country after ...

, and also in the condensed waste from etching aluminium films in an

integrated circuit An integrated circuit (IC), also known as a microchip or simply chip, is a set of electronic circuits, consisting of various electronic components (such as transistors, resistors, and capacitors) and their interconnections. These components a ...

factory.

References

F. Asinger (196662): ''Paraffins: Chemistry and Technology''. Revised English edition of German original published in 1956. 920 pages. Mark W. Jessell and G. S. Lister (1991): "Strain localization behaviour in experimental shear zones". ''Pure and Applied Geophysics'', volume 137, page 421–438. A. Roedig (1948): "Über die Synthese einiger Polychlorpolyene und die Atropisomerie der Oktachlorhexatriene". ''Experientia'', volume 4, pages 305–307 Win D. Means and Jin-Han Ree (1988): "Seven types of subgrain boundaries in octachloropropane". ''Journal of Structural Geology'', volume 10, issue 7, pages 765-770. Mark Jessel (1996):
Analogue Modelling at the University at Albany, State University of New York
(1996): Online collection of videos created by Youngdo Park, Jin-Han Ree, and Win D. Means. Accessed on 2020-07-03. Paul D. Bons, Mark W. Jessel, Lynn Evans, Terence Barr, and Karl Stüwe (2001) "Modeling of anisotropic grain growth in minerals" ''Tectonic Modeling: A Volume in Honor of Hans Ramberg''; ''Geological Society of America Memoir'', volume 193. 276 pages. Win D. Means (1983): "Microstructure and micromotion in recrystallization flow of octachloropropane: A first look". ''Geologische Rundschau'', volume 71, pages 511-528. W. C. McCrone (1949): "Boundary migration and grain growth". ''Discussions of the Faraday Society'', volume 5, pages 158-166. W. C. McCrone and P. T. Cheng (1949): "Grain growth in octachloropropane". ''Journal of Applied Physics'', volume 20, pages 230–231 P. A. Beck (1949): "Comments on grain growth in octachloropropane". ''Journal of Applied Physics'', volume 20, page 231. J. L. Urai, F. J. Humphreys, and S. E. Burrows (1980): "In-situ studies of the deformation and dynamic recrystallization of rhombohedral camphor". ''Journal of Materials Science'', volume 15, pages 1231–1240. K. R. S. Ascher and Z. H. Levinsox (1954): "Chemicals affecting the preimaginal stages of the housefly. III. Contact toxicity for third stage larvae of some chlorinated hydrocarbons deposited on adsorbent surfaces.". ''Rivista di Parassitologia'', Volume 15, issue 1, pages 57-61. E. A. Seiffer and H. F. Schoof (197): "Tests of 15 experimental molluscicides against ''Australorbis glabratus''". ''Public Health Reports'', volume 82, issue 9, pages 833–839. Lifei Zhang, Wenlong Yang, Linli Zhang, Xiaoxiu Li (2015): "Highly chlorinated unintentionally produced persistent organic pollutants generated during the methanol-based production of chlorinated methanes: A case study in China". ''Chemosphere'', volume 133, pages 1-5. Peggy Müller, Thomas Stock, Siegfried Bauer, and Ilona Wolff (2002): "Genotoxicological characterisation of complex mixtures: Genotoxic effects of a complex mixture of perhalogenated hydrocarbons". ''Mutation Research/Genetic Toxicology and Environmental Mutagenesis'', volume 515, issues 1–2, pages 99-109 Stephen W. Tobey and Robert. West (1964): "Hexachlorocyclopropane". ''Journal of the American Chemical Society'', volume 86, issue 1, pages 56–61. R. H. Atkinson, Joseph Steigman, and C. F. Hiskey (1952): "Analytical chemistry of niobium and tantalum. Chlorination of titania and distillation separation from niobium and tantalum". ''Analytical Chemistry'', volume 24, issue 3, pages 484–488. {{Authority control Chloroalkanes Perchlorocarbons