Swarts Reaction
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Swarts Reaction
Swarts fluorination is a process whereby the chlorine atoms in a compound – generally an organic compound, but experiments have been performed using silanes – are replaced with fluorine, by treatment with antimony trifluoride in the presence of chlorine or of antimony pentachloride. Some metal fluorides are particularly more useful than others, including silver(I) fluoride, mercurous fluoride, cobalt(II) fluoride and aforementioned antimony. Heating the mixture of the metal fluoride and the haloalkane (chlorine and bromine are replaced readily) yields the desired fluoro-alkane. In some particularly reactive cases, heating is unnecessary; shaking or stirring the reaction mixture is sufficient. This reaction has a good yield. The active species is antimony trifluorodichloride, which is produced in situ ''In situ'' (; often not italicized in English) is a Latin phrase that translates literally to "on site" or "in position." It can mean "locally", "on site", "on the premise ...
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Frédéric Swarts
Frédéric Swarts (2 September 1866 – 6 September 1940) was a Belgian chemist who prepared the first chlorofluorocarbon, CF2Cl2 (Freon-12) as well as several other related compounds. He was a professor in the civil engineering at the University of Ghent. In addition to his work on organofluorine chemistry, he authored the textbook "Cours de Chimie Organique."Frédéric Swarts "Cours de Chimie Organique" Librairie Scientifique, A. Hermann (Paris), 1908. He was a son of Theodore Swarts (chemist, *1839 Antwerpen; †1911 Kortenberg, Belgium) and a colleague of Leo Baekeland Leo Hendrik Baekeland (November 14, 1863 – February 23, 1944) was a Belgian chemist. He is best known for the inventions of Velox photographic paper in 1893, and Bakelite in 1907. He has been called "The Father of the Plastics Industry" .... References * {{DEFAULTSORT:Swarts, Frederic 20th-century Belgian inventors Belgian chemists 1866 births 1940 deaths Academic staff of Ghent Universit ...
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Chlorine
Chlorine is a chemical element with the 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 them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Electronegativity#Pauling electronegativity, Pauling scale, behind only oxygen and fluorine. Chlorine played an important role in the experiments conducted by medieval Alchemy, alchemists, which commonly involved the heating of chloride Salt (chemistry), salts like ammonium chloride (sal ammoniac) and sodium chloride (common salt), producing various chemical substances containing chlorine such as hydrogen chloride, mercury(II) chloride (corrosive sublimate), and hydrochloric acid (in the form of ). However ...
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Atom
Every atom is composed of a nucleus and one or more electrons bound to the nucleus. The nucleus is made of one or more protons and a number of neutrons. Only the most common variety of hydrogen has no neutrons. Every solid, liquid, gas, and plasma is composed of neutral or ionized atoms. Atoms are extremely small, typically around 100 picometers across. They are so small that accurately predicting their behavior using classical physics, as if they were tennis balls for example, is not possible due to quantum effects. More than 99.94% of an atom's mass is in the nucleus. The protons have a positive electric charge, the electrons have a negative electric charge, and the neutrons have no electric charge. If the number of protons and electrons are equal, then the atom is electrically neutral. If an atom has more or fewer electrons than protons, then it has an overall negative or positive charge, respectively – such atoms are called ions. The electrons of an atom are a ...
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Silane
Silane is an inorganic compound with chemical formula, . It is a colourless, pyrophoric, toxic gas with a sharp, repulsive smell, somewhat similar to that of acetic acid. Silane is of practical interest as a precursor to elemental silicon. Silane with alkyl groups are effective water repellents for mineral surfaces such as concrete and masonry. Silanes with both organic and inorganic attachments are used as coupling agents. Production Commercial-scale routes Silane can be produced by several routes. Typically, it arises from the reaction of hydrogen chloride with magnesium silicide: : Mg2Si + 4 HCl -> 2 MgCl2 + SiH4 It is also prepared from metallurgical-grade silicon in a two-step process. First, silicon is treated with hydrogen chloride at about 300 °C to produce trichlorosilane, HSiCl3, along with hydrogen gas, according to the chemical equation : Si + 3 HCl -> HSiCl3 + H2 The trichlorosilane is then converted to a mixture of silane and silicon tetrachloride: : 4 HS ...
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Fluorine
Fluorine is a chemical element with the symbol F and atomic number 9. It is the lightest halogen and exists at standard conditions as a highly toxic, pale yellow diatomic gas. As the most electronegative reactive element, it is extremely reactive, as it reacts with all other elements except for the light inert gases. Among the elements, fluorine ranks 24th in universal abundance and 13th in terrestrial abundance. Fluorite, the primary mineral source of fluorine which gave the element its name, was first described in 1529; as it was added to metal ores to lower their melting points for smelting, the Latin verb meaning 'flow' gave the mineral its name. Proposed as an element in 1810, fluorine proved difficult and dangerous to separate from its compounds, and several early experimenters died or sustained injuries from their attempts. Only in 1886 did French chemist Henri Moissan isolate elemental fluorine using low-temperature electrolysis, a process still employed for modern pr ...
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Antimony Trifluoride
Antimony trifluoride is the inorganic compound with the formula SbF3. Sometimes called Swarts' reagent, is one of two principal fluorides of antimony, the other being SbF5. It appears as a white solid. As well as some industrial applications, it is used as a reagent in inorganic and organofluorine chemistry. Preparation and structure In solid SbF3, the Sb centres have octahedral molecular geometry and are linked by bridging fluoride ligands. Three Sb–F bonds are short (192 pm) and three are long (261 pm). Because it is a polymer, SbF3 is far less volatile than related compounds AsF3 and SbCl3. SbF3 is prepared by treating antimony trioxide with hydrogen fluoride: :Sb2O3 + 6 HF → 2 SbF3 + 3 H2O The compound is a mild Lewis acid, hydrolyzing slowly in water. With fluorine, it is oxidized to give antimony pentafluoride. :SbF3 + F2 → SbF5 Applications It is used as a fluorination reagent in organic chemistry. This application was reported by the B ...
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Antimony Pentachloride
Antimony pentachloride is a chemical compound with the formula SbCl5. It is a colourless oil, but typical samples are yellowish due to dissolved chlorine. Owing to its tendency to hydrolyse to hydrochloric acid, SbCl5 is a highly corrosive substance and must be stored in glass or PTFE containers. Preparation and structure Antimony pentachloride is prepared by passing chlorine gas into molten antimony trichloride: :SbCl3 + Cl2 → SbCl5 Gaseous SbCl5 has a trigonal bipyramidal structure. Reactions This compounds reacts with water to form antimony pentoxide and hydrochloric acid: :2 SbCl5 + 5 H2O → Sb2O5 + 10 HCl The mono- and tetrahydrates are known, SbCl5·H2O and SbCl5·4H2O. This compound forms adducts with many Lewis bases. SbCl5 is a soft Lewis acid and its ECW model parameters are EA = 3.64 and CA = 10.42. It is used as the standard Lewis acid in the Gutmann scale of Lewis basicity. It is also a strong oxidizing agent. For example aromatic ethers are oxidized to th ...
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In Situ
''In situ'' (; often not italicized in English) is a Latin phrase that translates literally to "on site" or "in position." It can mean "locally", "on site", "on the premises", or "in place" to describe where an event takes place and is used in many different contexts. For example, in fields such as physics, geology, chemistry, or biology, ''in situ'' may describe the way a measurement is taken, that is, in the same place the phenomenon is occurring without isolating it from other systems or altering the original conditions of the test. The opposite of ''in situ'' is ''ex situ''. Aerospace In the aerospace industry, equipment on-board aircraft must be tested ''in situ'', or in place, to confirm everything functions properly as a system. Individually, each piece may work but interference from nearby equipment may create unanticipated problems. Special test equipment is available for this ''in situ'' testing. It can also refer to repairs made to the aircraft structure or flight con ...
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Halogenation Reactions
In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens (F2, Cl2, Br2, I2). Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized reagents exist for and introducing halogens into diverse substrates, e.g. thionyl chloride. Organic chemistry Several pathways exist for the halogenation of organic compounds, including free radical halogenation, ketone halogenation, electrophilic halogenation, and halogen addition reaction. The nature of the substrate determines the pathway. The facility of halogenation is influenced by the halogen. Fluorine and chlorine are more electrophilic and are m ...
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Substitution Reactions
A substitution reaction (also known as single displacement reaction or single substitution reaction) is a chemical reaction during which one functional group in a chemical compound is replaced by another functional group. Substitution reactions are of prime importance in organic chemistry. Substitution reactions in organic chemistry are classified either as electrophilic or nucleophile, nucleophilic depending upon the reagent involved, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a radical (chemistry), free radical, and whether the substrate (chemistry), substrate is aliphatic or aromatic. Detailed understanding of a reaction type helps to predict the product outcome in a reaction. It also is helpful for optimizing a reaction with regard to variables such as temperature and choice of solvent. A good example of a substitution reaction is halogenation. When chlorine gas (Cl2) is irradiated, some of the molecules are split into two chlorine ...
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