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Diethylaluminium Chloride
Diethylaluminium chloride, abbreviated DEAC, is an organoaluminium compound. Although usually given the chemical formula (C2H5)2AlCl, it exists as a dimer, C2H5)2AlClsub>2 It is a precursor to Ziegler-Natta catalysts employed for the production of polyolefins. The compound is also a Lewis acid, useful in organic synthesis. The compound is a colorless waxy solid, but is usually handled as a solution in hydrocarbon solvents. It is highly reactive, even pyrophoric. Structure Compounds of the empirical formula AlR2Cl (R = alkyl, aryl) exist as dimers with the formula (R2Al)2(μ-Cl)2. The aluminium adopts a tetrahedral geometry. Production Diethylaluminium chloride can be produced from ethylaluminium sesquichloride, (C2H5)3Al2Cl3, by reduction with sodium: :2 (C2H5)3Al2Cl3 + 3 Na → 3 (C2H5)2AlCl + Al + 3 NaCl It is also obtained from the reaction of triethylaluminium Triethylaluminium is one of the simplest examples of an organoaluminium compound. Despite its name it has the ...
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Organoaluminium Compound
Organoaluminium chemistry is the study of compounds containing bonds between carbon and aluminium. It is one of the major themes within organometallic chemistry. Illustrative organoaluminium compounds are the dimer trimethylaluminium, the monomer triisobutylaluminium, and the titanium-aluminium compound called Tebbe's reagent. The behavior of organoaluminium compounds can be understood in terms of the polarity of the C−Al bond and the high Lewis acidity of the three-coordinated species. Industrially, these compounds are mainly used for the production of polyolefins. History The first organoaluminium compound (C2H5)3Al2I3 was discovered in 1859. Organoaluminium compounds were, however, little known until the 1950s when Karl Ziegler and colleagues discovered the direct synthesis of trialkylaluminium compounds and applied these compounds to catalytic olefin polymerization. This line of research ultimately resulted in the Nobel Prize to Ziegler. Structure and bonding Aluminiu ...
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Chemical Formula
In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as parentheses, dashes, brackets, commas and ''plus'' (+) and ''minus'' (−) signs. These are limited to a single typographic line of symbols, which may include subscripts and superscripts. A chemical formula is not a chemical name, and it contains no words. Although a chemical formula may imply certain simple chemical structures, it is not the same as a full chemical structural formula. Chemical formulae can fully specify the structure of only the simplest of molecules and chemical substances, and are generally more limited in power than chemical names and structural formulae. The simplest types of chemical formulae are called ''empirical formulae'', which use letters and numbers indicating the numerical ''proportions'' of ato ...
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Polyolefin
A polyolefin is a type of polymer with the general formula (CH2CHR)n where R is an alkyl group. They are usually derived from a small set of simple olefins (alkenes). Dominant in a commercial sense are polyethylene and polypropylene. More specialized polyolefins include polyisobutylene and polymethylpentene. They are all colorless or white oils or solids. Many copolymers are known, such as polybutene, which derives from a mixture of different butene isomers. The name of each polyolefin indicates the olefin from which it is prepared; for example, polyethylene is derived from ethylene, and polymethylpentene is derived from 4-methyl-1-pentene. Polyolefins are not olefins themselves because the double bond of each olefin monomer is opened in order to form the polymer. Monomers having more than one double bond such as butadiene and isoprene yield polymers that contain double bonds ( polybutadiene and polyisoprene) and are usually not considered polyolefins. Polyolefins are the foun ...
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Lewis Acid
A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any species that has a filled orbital containing an electron pair which is not involved in bonding but may form a dative bond with a Lewis acid to form a Lewis adduct. For example, NH3 is a Lewis base, because it can donate its lone pair of electrons. Trimethylborane (Me3B) is a Lewis acid as it is capable of accepting a lone pair. In a Lewis adduct, the Lewis acid and base share an electron pair furnished by the Lewis base, forming a dative bond. In the context of a specific chemical reaction between NH3 and Me3B, a lone pair from NH3 will form a dative bond with the empty orbital of Me3B to form an adduct NH3•BMe3. The terminology refers to the contributions of Gilbert N. Lewis. From p. 142: "We are inclined to think of substances as poss ...
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Organic Synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one of the most important branches of organic chemistry. There are several main areas of research within the general area of organic synthesis: '' total synthesis'', ''semisynthesis'', and ''methodology''. Total synthesis A total synthesis is the complete chemical synthesis of complex organic molecules from simple, commercially available petrochemical or natural precursors. Total synthesis may be accomplished either via a linear or convergent approach. In a ''linear'' synthesis—often adequate for simple structures—several steps are performed one after another until the molecule is complete; the chemical compounds made in each step are called synthetic intermediates. Most often, each step in a synthesis refers to a separate rea ...
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Pyrophoricity
A substance is pyrophoric (from grc-gre, πυροφόρος, , 'fire-bearing') if it ignites spontaneously in air at or below (for gases) or within 5 minutes after coming into contact with air (for liquids and solids). Examples are organolithium compounds and triethylborane. Pyrophoric materials are often water-reactive as well and will ignite when they contact water or humid air. They can be handled safely in atmospheres of argon or (with a few exceptions) nitrogen. Class D fire extinguishers are designated for use in fires involving pyrophoric materials. A related concept is hypergolicity, in which two compounds spontaneously ignite when mixed. Uses The creation of sparks from metals is based on the pyrophoricity of small metal particles, and pyrophoric alloys are made for this purpose. The sparking mechanisms in lighters and various toys, using ferrocerium; starting fires without matches, using a firesteel; the flintlock mechanism in firearms; and spark testing fe ...
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Alkyl
In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula . Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula . Related concepts Alkylation is an important operation in refineries, for example in the production of high-octane gasoline. Alkylating antineoplastic agents are a class of compounds that are used to treat cancer. In such case, the term alkyl is used loosely. For example, nitrogen mustards are well-known alkylating agents, but they are not simple hydrocarbons. In chemistry, alkyl is a group, a substituent, that is attached to other molecular fragments. Fo ...
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Aryl
In organic chemistry, an aryl is any functional group or substituent derived from an aromaticity, aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used as a placeholder for the aryl group in chemical structure diagrams, analogous to “R” used for any organic substituent. “Ar” is not to be confused with the elemental symbol for argon. A simple aryl group is phenyl (), a group derived from benzene. Examples of other aryl groups consist of: * The Tolyl groups, tolyl group () which is derived from toluene (methylbenzene) * The xylyl group (), which is derived from xylene (dimethylbenzene) * The naphthyl group (), which is derived from naphthalene Arylation is the process in which an aryl group is attached to a substituent. It is typically achieved by cross-coupling reactions. Nomenclature The most basic aryl group is phenyl, which is made up of a benzene ring with one ...
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Ethylaluminium Sesquichloride
Ethylaluminium sesquichloride, also called EASC, is an industrially important organoaluminium compound used primarily as a precursor to triethylaluminium and as a catalyst component in Ziegler–Natta type systems for olefin and diene polymerizations. Other applications include use in alkylation reactions and as a catalyst component in linear oligomerization In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relat ... and cyclization of unsaturated hydrocarbons. EASC is a colourless liquid, spontaneously combustible in air and reacts violently when in contact with water and many other compounds. ...
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Triethylaluminium
Triethylaluminium is one of the simplest examples of an organoaluminium compound. Despite its name it has the formula Al2( C2H5)6 (abbreviated as Al2Et6 or TEA), as it exists as a dimer. This colorless liquid is pyrophoric. It is an industrially important compound, closely related to trimethylaluminium. Structure and bonding The structure and bonding in Al2R6 and diborane are analogous (R = alkyl). Referring to Al2Me6, the Al-C(terminal) and Al-C(bridging) distances are 1.97 and 2.14 Å, respectively. The Al center is tetrahedral. The carbon atoms of the bridging ethyl groups are each surrounded by five neighbors: carbon, two hydrogen atoms and two aluminium atoms. The ethyl groups interchange readily intramolecularly. At higher temperatures, the dimer cracks into monomeric AlEt3. Synthesis and reactions Triethylaluminium can be formed via several routes. The discovery of an efficient route was a significant technological achievement. The multistep process uses aluminium ...
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Ziegler–Natta Catalyst
A Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, is a catalyst used in the synthesis of polymers of 1-alkenes ( alpha-olefins). Two broad classes of Ziegler–Natta catalysts are employed, distinguished by their solubility: * Heterogeneous supported catalysts based on titanium compounds are used in polymerization reactions in combination with cocatalysts, organoaluminum compounds such as triethylaluminium, Al(C2H5)3. This class of catalyst dominates the industry. * Homogeneous catalysts usually based on complexes of the group 4 metals titanium, zirconium or hafnium. They are usually used in combination with a different organoaluminum cocatalyst, methylaluminoxane (or methylalumoxane, MAO). These catalysts traditionally contain metallocenes but also feature multidentate oxygen- and nitrogen-based ligands. Ziegler–Natta catalysts are used to polymerize terminal alkenes (ethylene and alkenes with the vinyl double bond): :''n'' CH2=CHR → − H2−CHR ...
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