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Friedel–Crafts Reaction
The Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877 to attach substituents to an aromatic ring. Friedel–Crafts reactions are of two main types: alkylation reactions and acylation reactions. Both proceed by electrophilic aromatic substitution. Alkylation With alkyl halides Friedel–Crafts alkylation involves the alkylation of an aromatic ring. Traditionally, the alkylating agents are alkyl halides. Many alkylating agents can be used instead of alkyl halides. For example, enones and epoxides can be used in presence of protons. Traditionally also, the reaction employs a strong Lewis acid, such as aluminium chloride as catalyst. This reaction suffers from the disadvantage that the product is more nucleophilic than the reactant because alkyl groups are activators for the Friedel–Crafts reaction. Consequently, overalkylation can occur. Steric hindrance can be exploited to limit the number of alkylations, as in the ''t ...
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Charles Friedel
Charles Friedel (; 12 March 1832 – 20 April 1899) was a French chemist and Mineralogy, mineralogist. Life A native of Strasbourg, France, he was a student of Louis Pasteur at the University of Paris, Sorbonne. In 1876, he became a professor of chemistry and mineralogy at the Sorbonne. Friedel developed the Friedel–Crafts reaction, Friedel-Crafts alkylation and acylation reactions with James Crafts in 1877, and attempted to make synthetic diamonds. His son Georges Friedel (1865–1933) also became a renowned mineralogist. Lineage * Friedel's wife's father was the engineer, Charles Combes.Charles Combes
, quercy.net, accessed April 2010 The Friedel family is a rich lineage of French scientists: ** Georges Friedel (1865–1933), French crystallographer and mineralogist; son of Charles ** Edmond Friedel (1895–1972), French Polytechnician and min ...
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Benzene Ethylation
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. Benzene is a colorless and highly flammable liquid with a sweet smell, and is partially responsible for the aroma of gasoline. It is used primarily as a precursor to the manufacture of chemicals with more complex structure, such as ethylbenzene and cumene, of which billions of kilograms are produced annually. Although benzene is a major industrial chemical, it finds limited use in consumer items because of its toxicity. History Discovery The word "''benzene''" derives from "''gum benzoin''" (benzoin res ...
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Cumene Process
The cumene process (cumene-phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene (isopropyl benzene), the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR)., and independently by Heinrich Hock in 1944 This process converts two relatively cheap starting materials, benzene and propylene, into two more valuable ones, phenol and acetone. Other reactants required are oxygen from air and small amounts of a radical initiator. Most of the worldwide production of phenol and acetone is now based on this method. In 2003, nearly 7 million tonnes of phenol was produced by the cumene process.Manfred Weber, Markus Weber, Michael Kleine-Boymann "Phenol" in Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH. . In order for this process to be economical, there must also be demand for the acetone by-product as well as the phenol. Steps of the p ...
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Ethylbenzene
Ethylbenzene is an organic compound with the formula . It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as an reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene. Occurrence and applications Ethylbenzene occurs naturally in coal tar and petroleum. The dominant application of ethylbenzene is its role as an intermediate in the production of polystyrene. Catalytic dehydrogenation of ethylbenzene gives hydrogen and styrene: : → C6H5CH=CH2 + As of May 2012, more than 99% of all the ethylbenzene produced is used for this purpose. Ethylbenzene hydroperoxide, a reagent and radical initiator, is produced by autoxidation of ethylbenzene: :C6H5CH2CH3 + O2 → C6H5CH(O2H)CH3 Niche uses Ethylbenzene is added to gasoline as ...
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Neophyl Chloride Synthesis
Neophyl can mean: * neophyl group, trivial name of 2-methyl-2-phenylpropyl functional group, PhC(CH3)2CH2- (e.g. in neophyl chloride) * one of trade names of diprophylline {{Disambiguation ...
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Methallyl Chloride
Methallyl chloride is the organic compound with the formula CH2=C(CH3)CH2Cl. It is a colorless liquid and a lacrymator. Its properties are similar to those of allyl chloride. It is a strong alkylating agent used to install isobutenyl groups. Reactivity It is also a precursor to meth allyl ligand. It is an isomer of crotyl chloride. Methylenecyclopropane can be synthesised via an intramolecular cyclisation reaction from methallyl chloride by treatment with a strong base such as sodium amide Sodium amide, commonly called sodamide (systematic name sodium azanide), is the inorganic compound with the formula . It is a salt composed of the sodium cation and the azanide anion. This solid, which is dangerously reactive toward water, is white .... : References {{Reflist Organochlorides IARC Group 3 carcinogens Allyl compounds ...
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Neophyl Chloride
Neophyl chloride, C6H5C(CH3)2CH2Cl, is a halogenated organic compound with unusual nucleophilic substitution properties. Neophyl chloride is used to form a versatile organolithium reagent, neophyl lithium, by reaction with lithium. Preparation Neophyl chloride was first synthesized by Haller and Ramart by reacting the chlorinating reagent thionyl chloride with neophyl alcohol: :C6H5C(CH3)2CH2OH + SOCl2 → C6H5C(CH3)2CH2Cl + HCl + SO2 It is easily prepared on a large scale by combining benzene and methallyl chloride in the presence of a catalytic quantity of sulfuric acid. The reaction is an example of an electrophilic aromatic substitution. :H2C=C(CH3)CH2Cl + C6H6 → C6H5C(CH3)2CH2Cl Alternatively ''tert''-butylbenzene can be chlorinated with sulfuryl chloride. Reactions and applications Neophyl chloride can be used to form an organolithium reagent, neophyl lithium, by reaction with lithium. Organolithium reagents are useful due to their nucleophilic properties and thei ...
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Alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, and Biological Chemistry'. 1232 pages. Two general types of monoalkenes are distinguished: terminal and internal. Also called α-olefins, terminal alkenes are more useful. However, the International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc. for cyclic ones; and "olefin" for the general class – cyclic or acyclic, with one or more double bonds. Acyclic alkenes, with only one double bond and no other functional groups (also known as mono-enes) form a homologous series of hydrocarbons with the general formula with '' ...
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Cumene Process
The cumene process (cumene-phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene (isopropyl benzene), the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR)., and independently by Heinrich Hock in 1944 This process converts two relatively cheap starting materials, benzene and propylene, into two more valuable ones, phenol and acetone. Other reactants required are oxygen from air and small amounts of a radical initiator. Most of the worldwide production of phenol and acetone is now based on this method. In 2003, nearly 7 million tonnes of phenol was produced by the cumene process.Manfred Weber, Markus Weber, Michael Kleine-Boymann "Phenol" in Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH. . In order for this process to be economical, there must also be demand for the acetone by-product as well as the phenol. Steps of the p ...
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