Vinyl chloride, also known as chloroethene in IUPAC nomenclature, is an important industrial chemical chiefly used to produce its polymer, polyvinyl chloride (PVC). At room temperature, it is a toxic, colourless gas with a sweet odour. Polymer is a generic term used to describe a very long molecule consisting of structural units and repeating units connected by covalent chemical bonds. ... Polyvinyl chloride (PVC) is a widely-used plastic. ...

History

Vinyl chloride was first produced in 1835 by Justus von Liebig and his student Henri Victor Regnault. They obtained it by treating ethylene dichloride with a solution of potassium hydroxide in ethanol. Freiherr Justus von Liebig (May 12, 1803 in Darmstadt, Germany - April 18, 1873 in Munich, Germany) was a German chemist. ... Henri Victor Regnault (July 21, 1810 - January 19, 1878) was a French chemist and physicist best known for his careful measurements of the thermal properties of gases. ... Flash point  ? °C R/S statement R: ? S: ? RTECS number  ? Supplementary data page Structure and properties n, εr, etc. ... The chemical compound potassium hydroxide, (KOH) sometimes known as caustic potash, potassa, potash lye, and potassium hydrate, is a metallic base. ... Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless chemical compound, one of the alcohols that is most often found in alcoholic beverages. ...

In 1912, Fritz Klatte, a German chemist working for Griesheim-Elektron, patented a means to produce vinyl chloride from acetylene and hydrogen chloride using mercuric chloride as a catalyst. While this method was widely used during the 1930's and 1940's, it has since been superseded by more economical processes. The chemical compound and unsaturated hydrocarbon acetylene, also known under IUPAC nomenclature (see IUPAC nomenclature of organic chemistry) as ethyne, was discovered in 1836 by Edmund Davy, in England. ... The chemical substance hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride (HCl) gas. ... Mercury chloride is a white poisonous soluble crystalline sublimate of mercury, used as a pesticide or antiseptic or wood preservative. ... A catalyst (Greek: καταλύτης, catalytēs) is a substance that accelerates the rate (speed) of a chemical reaction (see also catalysis). ...

Production

Vinyl chloride is manufactured on the industrial scale from ethylene and chlorine. In the presence of iron(III) chloride as a catalyst, these compounds react to produce ethylene dichloride according to the chemical equation R-phrases R12, R67 S-phrases S2, S9, S16, S33, S46 Flash point Flammable gas Explosive limits 2. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... Iron(III) chloride, generically called ferric chloride, is an iron-based salt of chemical formula FeCl3. ... A chemical reaction is a process that results in the interconversion of chemical substances [1]. The substance or substances initially involved in a chemical reaction are called reactants. ... Flash point  ? °C R/S statement R: ? S: ? RTECS number  ? Supplementary data page Structure and properties n, εr, etc. ... A chemical equation is a symbolic representation of a chemical reaction. ...

CH₂=CH₂ + Cl₂ → ClCH₂CH₂Cl

Typically, this reaction is conducted in a bath of boiling ethylene dichloride. When then heated to 500 °C at 15–30 atm (1.5 to 3 MPa) pressure, the ethylene dichloride decomposes to produce vinyl chloride and hydrogen chloride. R-phrases R12, R67 S-phrases S2, S9, S16, S33, S46 Flash point Flammable gas Explosive limits 2. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... Flash point  ? °C R/S statement R: ? S: ? RTECS number  ? Supplementary data page Structure and properties n, εr, etc. ... The megapascal, symbol MPa is an SI unit of pressure. ...

ClCH₂CH₂Cl → CH₂=CHCl + HCl

In industrial practice, the hydrogen chloride produced in this step is mixed with oxygen and then reacted with additional ethylene on a copper(II) chloride catalyst to produce even more ethylene dichloride via the reaction Flash point  ? °C R/S statement R: ? S: ? RTECS number  ? Supplementary data page Structure and properties n, εr, etc. ... The chemical substance hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride (HCl) gas. ... Copper(II) chloride is the higher chloride of copper, with the formula CuCl2. ...

CH₂=CH₂ + 2 HCl + ½ O₂ → ClCH₂CH₂Cl + H₂O

The hydrogen chloride consumed in this step exactly balances that produced in the second step, and the resulting balanced process neither requires hydrogen chloride as an input nor produces it as a waste. Due to the economical advantages of this process, most vinyl chloride has been produced via this technique since the late 1950s. R-phrases R12, R67 S-phrases S2, S9, S16, S33, S46 Flash point Flammable gas Explosive limits 2. ... Flash point  ? °C R/S statement R: ? S: ? RTECS number  ? Supplementary data page Structure and properties n, εr, etc. ... Water (from the Old English word wæter; c. ...

Uses

By far the most important use of vinyl chloride is its polymerization to make PVC. Much smaller amounts are used to produce other chlorinated hydrocarbons including ethylidene dichloride, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene, and vinylidene chloride. Polyvinyl chloride (PVC) is a widely-used plastic. ... Chlorinated hydrocarbons are a broad class of organic chemicals used mainly as solvents but also with many other uses. ... 1,1-Dichloroethane, commonly known by its older name ethylidene dichloride, or ethylidene chloride is a chlorinated hydrocarbon, a colorless aromatic oily liquid. ... The chemical compound 1,1,1-trichloroethane is a chlorinated hydrocarbon that was until recently widely used as an industrial solvent. ... The chemical compound trichloroethylene is a chlorinated hydrocarbon commonly used as an industrial solvent. ... Tetrachloroethylene Cl2C=CCl2 is a manufactured chemical that is widely used for the dry cleaning of fabrics and for metal-degreasing. ... Disclaimer and references 1,1-Dichloroethene, commonly called 1,1-dichloroethylene or 1,1-DCE, is an organochloride with the molecular formula C2H2Cl2. ...

Vinyl chloride's toxicity limits its use in consumer goods, though it has been historically (until 1974) utilized as an aerosol spray propellant; carcinogenic potential has long been established and the prospective legal liability is comparable to that of asbestos (implicated in the causality of mesothelioma). Accumulation of vinyl chloride vapor in hair salons readily exceeded the NOAEL (NO Adverse Effect Level) exposure guidelines, its high index of mutagenicity possibly responsible for an increase of an order of magnitude of the occurrence of cancer in the most severely affected occupations. Aerosol spray can Aerosol spray is the name given to a type of canister containing liquid under pressure from pressurized vapor in equilibrium with another liquid, which often also dissolves the payload (see propellant below). ... In pathology, a carcinogen is any substance or agent that promotes cancer. ... Fibrous asbestos on muscovite Asbestos Asbestos Asbestos (a misapplication of Latin: asbestos quicklime from Greek ἄσβεστος: a-, not; sbestos, extinguishable) describes any of a group of fibrous metamorphic minerals of the hydrous magnesium silicate variety. ... A hair salon is a place where one goes to get their hair cut, as well as styled, highlighted or coloured. ... In biology, a mutagen (Latin, literally origin of change) is an agent that changes the genetic information (usually DNA) of an organism and thus increases the number of mutations above the natural background level. ...

It was briefly used as an inhalational anaesthetic, in a similar vein to ethyl chloride, though its toxicity forced this practice to be abandoned. Inhalational anaesthetics are gases or vapours possessing anaesthetic qualities. ... Ethyl chloride is a chemical compound once widely used in producing tetraethyl lead, a gasoline additive. ...

Health effects

Vinyl chloride depresses the central nervous system, and inhaling its vapors produces symptoms similar to alcohol intoxication. These include headache, dizziness, and loss of coordination, and in severe cases may progress to hallucination, unconsciousness, and death by respiratory failure. A diagram showing the CNS: 1. ... ... A hallucination is a sensory perception experienced in the absence of an external stimulus, as distinct from an illusion, which is a misperception of an external stimulus. ... Respiratory failure is a medical term for inadequate gas exchange by the respiratory system. ...

In laboratory animals, exposure to vinyl chloride during pregnancy has produced miscarriages and birth defects. Its effect on human reproduction is unknown. Pregnancy Pregnancy is the carrying of one or more embryos or fetuses by female mammals, including humans, inside their bodies. ... Miscarriage or spontaneous abortion is the natural or accidental termination of a pregnancy at a stage where the embryo or the fetus is incapable of surviving, generally defined at a gestation of prior to 20 weeks. ... A congenital disorder is a medical condition or defect that is present at or before birth (for example, congenital heart disease). ...

Long-term exposure to vinyl chloride can cause chronic skin irritations and has also been linked to a painful inflammation of the extremities called Raynaud's syndrome. Vinyl chloride is considered to be a carcinogen and has in particular been linked to certain cancers of the liver—chiefly, hepatocellular carcinoma. In medicine, Raynauds phenomenon is discoloration of the fingers or toes due to emotion or cold in a characteristic pattern in time: white, blue and red. ... In pathology, a carcinogen is any substance or agent that promotes cancer. ... When normal cells are damaged beyond repair, they are eliminated by apoptosis. ... The liver is one of the largest internal organs of the human body. ... Hepatocellular carcinoma (HCC, also called hepatoma or liver cancer) is a primary malignancy (cancer) of the liver. ...

External links

• Information on the aerosol propellant controversy