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Hexafluorobutadiene
Hexafluorobutadiene is an organofluorine compound with the formula (CF2=CF)2. A colorless gas, it has attracted attention as an etchant in microelectronics. It is the perfluoroanalogue of butadiene. It can be prepared by coupling of C2 compounds such as from chlorotrifluoroethylene or bromotrifluoroethylene. Routes from C4 species have also been demonstrated. For example, an early synthesis involved Zn-induced dechlorinaion of 1,2,3,4-tetrachloro-1,1,2,3,4,4-hexafluorobutane. Hexafluorobutadiene dimerizes via a +2process at 150 °C to give perfluorinated divinylcyclobutanes.{{cite book , doi=10.1002/0470864028.ch21 , title=The Chemistry of Cyclobutanes , chapter=Fluorinated Cyclobutanes and Their Derivatives, first1=David M., last1=Lemal, first2=Xudong, last2=Chen , editor=Zvi Rappoport , editor2=Joel F. Liebman, year=2005, series=PATAI'S Chemistry of Functional Groups, pages=955–1029 , isbn=0470864001 See also * Hexafluoro-2-butyne, an isomer of C4F6 * Hexafluorocyclo ...
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Organofluorine Compound
Organofluorine chemistry describes the chemistry of the organofluorines, organic compounds that contain the carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, refrigerants, and reagents in catalysis. In addition to these applications, some organofluorine compounds are pollutants because of their contributions to ozone depletion, global warming, bioaccumulation, and toxicity. The area of organofluorine chemistry often requires special techniques associated with the handling of fluorinating agents. The carbon–fluorine bond Fluorine has several distinctive differences from all other substituents encountered in organic molecules. As a result, the physical and chemical properties of organofluorines can be distinctive in comparison to other organohalogens. # The carbon–fluorine bond is one of the strongest in organic chemistry (an average bond energy around 480 kJ/molKirsch, Peer ''Modern fluoroorga ...
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Butadiene
1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two vinyl groups. It is the simplest conjugated diene. Although butadiene breaks down quickly in the atmosphere, it is nevertheless found in ambient air in urban and suburban areas as a consequence of its constant emission from motor vehicles. The name butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene with structure H2C=C=CH−CH3. This allene has no industrial significance. History In 1863, the French chemist E. Caventou isolated butadiene from the pyrolysis of amyl alcohol. This hydrocarbon was identified as butadiene in 1886, after Henry Edward Armstrong isolated it from among the pyrolysis products of petroleum. In 1910, the Russian chemist Sergei Lebedev polymerized butadiene and obtained a material wit ...
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Chlorotrifluoroethylene
Chlorotrifluoroethylene (CTFE) is a chlorofluorocarbon with chemical formula CFCl=CF2. It is commonly used as a refrigerant in cryogenic applications. CTFE has a carbon-carbon double bond and so can be polymerized to form polychlorotrifluoroethylene or copolymerized to produce the plastic ECTFE. PCTFE has the trade name Neoflon PCTFE from Daikin Industries in Japan, and it used to be produced under the trade name Kel-F from 3M Corporation in Minnesota. Production and reactions Chlorotrifluoroethylene is produced commercially by the dechlorination of 1,1,2-trichloro-1,2,2-trifluoroethane with zinc: :CFCl2-CF2Cl + Zn → CClF=CF2 + ZnCl2 In 2012, an estimated 1–10 million pounds were produced commercially in the United States. The thermal dimerization of chlorotrifluoroethylene gives 1,2-dichloro-1,2,3,3,4,4-hexafluorocyclobutane. Dichlorination of the latter gives hexafluorocyclobutene Hexafluorocyclobutene is the organofluorine compound with the formula (CF2)2(CF)2. ...
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Hexafluoro-2-butyne
Hexafluoro-2-butyne (HFB) is a fluorocarbon with the chemical structure CF3C≡CCF3. HFB is a particularly electrophilic acetylene derivative, and hence a potent dienophile for Diels–Alder reactions. HFB is prepared by the action of sulfur tetrafluoride on acetylenedicarboxylic acid or by the reaction of potassium fluoride (KF) with hexachlorobutadiene Hexachlorobutadiene, Cl2C=C(Cl)C(Cl)=CCl2, is a colorless liquid at room temperature that has an odor similar to that of turpentine. It is a chlorinated aliphatic diene with niche applications but is most commonly used as a solvent for other chlo .... References {{Reflist Alkyne derivatives Trifluoromethyl compounds Fluorocarbons ...
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Hexafluorocyclobutene
Hexafluorocyclobutene is the organofluorine compound with the formula (CF2)2(CF)2. A colorless gas, it is a precursor to a variety of compounds, including squaric acid. Hexafluorocyclobutene is prepared in two steps from chlorotrifluoroethylene. The thermal dimerization gives 1,2-dichloro-1,2,3,3,4,4-hexafluorocyclobutane. Dechlorination of the latter gives hexafluorocyclobutene: :C4F6Cl2 + Zn -> C4F6 + ZnCl2 Safety Reminiscent of perfluoroisobutene, hexafluorocyclobutene is quite toxic with an LD = 6000 mg/min/m−3 (mice).{{cite book , doi=10.1016/B978-008043405-6/50040-2, chapter=Highly-toxic fluorine compounds, title=Fluorine Chemistry at the Millennium, year=2000, last1=Timperley, first1=Christopher M., pages=499–538, isbn=9780080434056 See also *Hexafluoro-2-butyne *Hexafluorobutadiene Hexafluorobutadiene is an organofluorine compound with the formula (CF2=CF)2. A colorless gas, it has attracted attention as an etchant in microelectronics. It is the perfluor ...
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Hexachlorobutadiene
Hexachlorobutadiene, Cl2C=C(Cl)C(Cl)=CCl2, is a colorless liquid at room temperature that has an odor similar to that of turpentine. It is a chlorinated aliphatic diene with niche applications but is most commonly used as a solvent for other chlorine-containing compounds.Manfred Rossberg et al. "Chlorinated Hydrocarbons," Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag GmbH & Co, 2006, Kenric A. Marshall, "Chlorocarbons and Chlorohydrocarbons, Survey," Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons Inc, 2003, Synthesis Hexachlorobutadiene, or HCBD, is primarily produced in chlorinolysis plants as a by-product in the production of carbon tetrachloride and tetrachloroethene. Chlorinolysis is a radical chain reaction that occurs when hydrocarbons are exposed to chlorine gas under pyrolytic conditions. The hydrocarbon is chlorinated and the resulting chlorocarbons are broken down. This process is analogous to combustion, but with chlorine inste ...
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Organofluorides
Organofluorine chemistry describes the chemistry of the organofluorines, organic compounds that contain the carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from Lipophobicity, oil and hydrophobe, water repellents to pharmaceuticals, refrigerants, and reagents in catalysis. In addition to these applications, some organofluorine compounds are pollutants because of their contributions to ozone depletion, global warming, bioaccumulation, and toxicity. The area of organofluorine chemistry often requires special techniques associated with the handling of fluorinating agents. The carbon–fluorine bond Fluorine has several distinctive differences from all other substituents encountered in organic molecules. As a result, the physical and chemical properties of organofluorines can be distinctive in comparison to other organohalogens. # The carbon–fluorine bond is one of the strongest in organic chemistry (an average bond energy around 480 kJ/molKirsch ...
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