Tetraiodoethylene

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Tetraiodoethylene
Tetraiodoethylene.png
C2I4 3D.png
Names
IUPAC name
tetraiodoethene
Other names
Periodoethylene, Periodoethene, Diiodoform, Ethylene tetraiodide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.434 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-176-2
PubChem CID
UNII
  • InChI=1S/C2I4/c3-1(4)2(5)6
    Key: ZGQURDGVBSSDNF-UHFFFAOYSA-N
  • C(=C(I)I)(I)I
Properties
C2I4
Molar mass 531.640 g·mol−1
Appearanceyellow crystalline solid
Odor Odourless [1]
Density 2.98
Melting point 187–192 °C (369–378 °F; 460–465 K) [2]
Boiling point Sublimates [2]
Insoluble
Solubility Soluble in chloroform, carbon disulphide, benzene and toluene [3]
Hazards
GHS labelling: [4]
GHS-pictogram-exclam.svg
Warning
H302, H312, H315, H319, H332, H335
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetraiodoethylene (TIE), or diiodoform, is the periodinated analogue of ethylene with the chemical formula C2I4. It is a decomposition product of carbon tetraiodide and diiodoacetylene. [5] It is an odourless yellow crystalline solid that is soluble in benzene and chloroform, and insoluble in water. [2] It has been used as an antiseptic and a component in pesticide and fungicide formulations. [6] [7]

Contents

Tetraiodoethylene reacts with ethylamine to give ethylamine di-tetraiodoethylene, EtNH2.(C2I4)2, and ethylaminetetraiodoethylene. [8] Tetraiodoethylene and iodine pentafluoride yield iodopentafluoroethane. [9]

Tetraiodoethylene turns brown and emits a "characteristic" odour due to decomposition when exposed to light. [10]

History

Tetraiodoethylene was discovered by Baeyer in 1885. [5] It was proposed as an antiseptic under the name Diiodoform, in 1893 by M. L. Maquenne and Taine. [10] It was an alternative to iodoform [10] which has a strong and persistent odour that caused difficulties for physicians in private practices. [11]

Synthesis

Tetraiodoethylene can be made by the iodination of calcium carbide: [1]

CaC2 + 3I2 → C2I4 + CaI2

Diiodoacetylene is a byproduct of the reaction which can later be iodinated to TIE. [1]

The action of aqueous solution of potassium hydroxide and iodine on barium carbide in chloroform or benzene can also give TIE. [10] Another synthesis involves mixing separate solutions of diiodoacetylene and iodine in carbon disulphide. Tetraiodoethylene would be left as a residue after carbon disulphide was evaporated. [10]

See also

Related Research Articles

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Acetylene is the chemical compound with the formula C2H2 and structure H−C≡C−H. It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure form and thus is usually handled as a solution. Pure acetylene is odorless, but commercial grades usually have a marked odor due to impurities such as divinyl sulfide and phosphine.

<span class="mw-page-title-main">Bromine</span> Chemical element, symbol Br and atomic number 35

Bromine is a chemical element; it has symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig and Antoine Jérôme Balard, its name was derived from the Ancient Greek βρῶμος (bromos) meaning "stench", referring to its sharp and pungent smell.

<span class="mw-page-title-main">Ethanol</span> Organic compound (CH₃CH₂OH)

Ethanol is an organic compound with the chemical formula CH3CH2OH. It is an alcohol, with its formula also written as C2H5OH, C2H6O or EtOH, where Et stands for ethyl. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive recreational drug, and the active ingredient in alcoholic drinks.

<span class="mw-page-title-main">Iodine</span> Chemical element, symbol I and atomic number 53

Iodine is a chemical element; it has symbol I and atomic number 53. The heaviest of the stable halogens, it exists at standard conditions as a semi-lustrous, non-metallic solid that melts to form a deep violet liquid at 114 °C (237 °F), and boils to a violet gas at 184 °C (363 °F). The element was discovered by the French chemist Bernard Courtois in 1811 and was named two years later by Joseph Louis Gay-Lussac, after the Ancient Greek Ιώδης 'violet-coloured'.

<span class="mw-page-title-main">Phenol</span> Organic compound (C6H5OH)

Phenol, or Benzenol, is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

<span class="mw-page-title-main">Creosote</span> Tar distillation byproduct used as wood preservative

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Chloroform, or trichloromethane, is an organic compound with the formula CHCl3 and a common solvent. It is a very volatile, colorless, strong-smelling, dense liquid produced on a large scale as a precursor to refrigerants and in turn PTFE. Chloroform is a trihalomethane that serves as a powerful anesthetic, euphoriant, anxiolytic, and sedative when inhaled or ingested. Chloroform was used as an anesthetic between the 19th century and the first half of the 20th century. It is miscible with many solvents but it is only very slightly soluble in water.

<span class="mw-page-title-main">Sodium hypochlorite</span> Chemical compound (known in solution as bleach)

Sodium hypochlorite, commonly known in a dilute solution as (chlorine) bleach, is an inorganic chemical compound with the formula NaOCl, consisting of a sodium cation and a hypochlorite anion. It may also be viewed as the sodium salt of hypochlorous acid. The anhydrous compound is unstable and may decompose explosively. It can be crystallized as a pentahydrate NaOCl·5H
2
O
, a pale greenish-yellow solid which is not explosive and is stable if kept refrigerated.

<span class="mw-page-title-main">Carbon tetrachloride</span> Chemical compound

Carbon tetrachloride, also known by many other names (such as carbon tet for short and tetrachloromethane, also recognised by the IUPAC) is a chemical compound with the chemical formula CCl4. It is a non-flammable, dense, colourless liquid with a "sweet" chloroform-like odour that can be detected at low levels. It was formerly widely used in fire extinguishers, as a precursor to refrigerants and as a cleaning agent, but has since been phased out because of environmental and safety concerns. Exposure to high concentrations of carbon tetrachloride can affect the central nervous system and degenerate the liver and kidneys. Prolonged exposure can be fatal.

<span class="mw-page-title-main">Calcium carbide</span> Chemical compound

Calcium carbide, also known as calcium acetylide, is a chemical compound with the chemical formula of CaC2. Its main use industrially is in the production of acetylene and calcium cyanamide.

<span class="mw-page-title-main">Ethylene oxide</span> Cyclic compound (C2H4O)

Ethylene oxide is an organic compound with the formula C2H4O. It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of a silver catalyst.

<span class="mw-page-title-main">Iodoform</span> Chemical compound

Iodoform is the organoiodine compound with the chemical formula CHI3. It is a pale yellow, crystalline, volatile substance, with a penetrating and distinctive odor and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant.

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2
C
2
.H
2
O
is a reddish-brown explosive powder.

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<span class="mw-page-title-main">Haloform reaction</span> Chemical reaction involving repeated halogenation of an acetyl group (–COCH3)

In chemistry, the haloform reaction is a chemical reaction in which a haloform is produced by the exhaustive halogenation of an acetyl group, in the presence of a base. The reaction can be used to transform acetyl groups into carboxyl groups or to produce chloroform, bromoform, or iodoform. Note that fluoroform can't be prepared in this way.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.

Unlike its lighter congeners, the halogen iodine forms a number of stable organic compounds, in which iodine exhibits higher formal oxidation states than -1 or coordination number exceeding 1. These are the hypervalent organoiodines, often called iodanes after the IUPAC rule used to name them.

References

  1. 1 2 3 TETRA-IODO-ETHYLENE, The Pharmaceutical Era. (1897). USA, D. O. Haynes & Company.
  2. 1 2 3 Lide, D. R. (1995). CRC Handbook of Chemistry and Physics. (Special Student Edition): A Ready-Reference Book of Chemical and Physical Data. CRC-Press. Page 522
  3. 1 2 Diiodoform in Notes on New Remedies. (1893). USA: Lehn & Fink.
  4. "Tetraiodoethylene". pubchem.ncbi.nlm.nih.gov.
  5. 1 2 Peculiar Decomposition of Diiodoacetylene, Victor Meyel and Wilhelm Pemsel (1896)
  6. The Code of Federal Regulations of the United States of America (1984). U.S. Government Printing Office.
  7. Iodine and Plant Life: Annotated Bibliography, 1813-1949. With Review of the Literature. (1950). UK: Chilean Iodine Educational Bureau. page 22
  8. Action of Tetraiodoethylene on Organic Bases, Chemical Abstracts. (1912). American Chemical Society.
  9. Journal of the Chemical Society. (1948). page 2188
  10. 1 2 3 4 5 New Remedies – Diiodoform in Merck's Market Report and Pharmaceutical Journal: An Independent Monthly Magazine Devoted to the Professional and Commercial Interests of the Druggist. (1894).
  11. Selections – DIIODOFORM in The International Dental Journal. (1895). USA: International Dental Publication Company.