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Olefin Conversion Technology
Olefin Conversion Technology, also called the Phillips Triolefin Process, is the industrial process that interconverts propylene with ethylene and 2-butenes. The process is also called the ethylene to propylene (ETP) process. In ETP, ethylene is dimerized to 1-butene, which is isomerized to 2-butenes. The 2-butenes are then subjected to metathesis with ethylene. Rhenium- and molybdenum-containing heterogeneous catalysis are used. Nowadays, only the reverse reaction is practiced, i.e., the conversion of ethylene and 2-butene to propylene: :CH2=CH2 + CH3CH=CHCH3 → 2 CH2=CHCH3 The technology is founded on an olefin metathesis reaction discovered at Phillips Petroleum Company. The originally described process employed catalysts molybdenum hexacarbonyl, tungsten hexacarbonyl, and molybdenum oxide Molybdenum oxide may refer to: * Molybdenum(IV) oxide (molybdenum dioxide, ) * Molybdenum(VI) oxide Molybdenum trioxide describes a family of inorganic compounds with the formula Mo ...
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Propylene
Propylene, also known as propene, is an unsaturated organic compound with the chemical formula CH3CH=CH2. It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petroleum-like odor. Production Steam cracking The dominant technology for producing propylene is steam cracking. The same technology is applied to ethane to ethylene. These two conversions are the #2 and #1 processes in the chemical industry, as judged by their scale. In this process, propane undergoes dehydrogenation. The by-product is hydrogen: :CH3CH2CH3 → CH3CH=CH2 + H2 The yield of propene is about 85 m%. By-products are usually used as fuel for the propane dehydrogenation reaction. Steam cracking is one of the most energy-intensive industrial processes. The feedstock is naphtha or propane, especially in the Middle East, where there is an abundance of propane from oil/gas operations. Propene can be separated by fractional distilla ...
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Ethylene
Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene is widely used in the chemical industry, and its worldwide production (over 150 million tonnes in 2016) exceeds that of any other organic compound. Much of this production goes toward polyethylene, a widely used plastic containing polymer chains of ethylene units in various chain lengths. Ethylene is also an important natural plant hormone and is used in agriculture to force the ripening of fruits. The hydrate of ethylene is ethanol. Structure and properties This hydrocarbon has four hydrogen atoms bound to a pair of carbon atoms that are connected by a double bond. All six atoms that comprise ethylene are coplanar. The H-C-H angle is 117.4°, close to the 120° for ideal sp² hybridized carbon. The molecule is also relatively weak: rota ...
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2-butene
But-2-ene is an acyclic alkene with four carbon atoms. It is the simplest alkene exhibiting ''cis''/''trans''-isomerism (also known as (''E''/''Z'')-isomerism); that is, it exists as two geometric isomers ''cis''-but-2-ene ((''Z'')-but-2-ene) and ''trans-''but-2-ene ((''E'')-but-2-ene). It is a petrochemical, produced by the catalytic cracking of crude oil or the dimerization of ethylene. Its main uses are in the production of gasoline (petrol) and butadiene,. although some but-2-ene is also used to produce the solvent butanone via hydration to 2-butanol followed by oxidation. The two isomers are extremely difficult to separate by distillation because of the proximity of their boiling points (~4 °C for ''cis'' and ~1 °C for ''trans''Chemical Safety Information from Intergovernmental Organizations
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1-Butene
1-Butene (or 1-Butylene) is the organic compound with the formula CH3CH2CH=CH2. It is a colorless gas that is easily condensed to give a colorless liquid. It is classified as a linear alpha-olefin. It is one of the isomers of butene (butylene). It is a precursor to diverse products. Reactions Polymerization of 1-butene give polybutene, which is used to make piping for domestic plumbing. Its main application is as a comonomer in the production of certain kinds of polyethylene, such as linear low-density polyethylene (LLDPE). It has also been used as a precursor to polypropylene resins, butylene oxide, and butanone. Manufacturing 1-Butene is produced by separation from crude C4 refinery streams and by ethylene dimerization. The former affords a mixture of 1-and 2-butenes, while the latter affords only the terminal alkene. It is distilled to give a very high purity product. An estimated 12 billion kilograms were produced in 2011. See also *Butene *Dimer (chemistry) *Octene Oct ...
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2-Butene
But-2-ene is an acyclic alkene with four carbon atoms. It is the simplest alkene exhibiting ''cis''/''trans''-isomerism (also known as (''E''/''Z'')-isomerism); that is, it exists as two geometric isomers ''cis''-but-2-ene ((''Z'')-but-2-ene) and ''trans-''but-2-ene ((''E'')-but-2-ene). It is a petrochemical, produced by the catalytic cracking of crude oil or the dimerization of ethylene. Its main uses are in the production of gasoline (petrol) and butadiene,. although some but-2-ene is also used to produce the solvent butanone via hydration to 2-butanol followed by oxidation. The two isomers are extremely difficult to separate by distillation because of the proximity of their boiling points (~4 °C for ''cis'' and ~1 °C for ''trans''Chemical Safety Information from Intergovernmental Organizations
) ...
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Heterogeneous Catalysis
In chemistry, heterogeneous catalysis is catalysis where the phase of catalysts differs from that of the reactants or products. The process contrasts with homogeneous catalysis where the reactants, products and catalyst exist in the same phase. Phase distinguishes between not only solid, liquid, and gas components, but also immiscible mixtures (e.g. oil and water), or anywhere an interface is present. Heterogeneous catalysis typically involves solid phase catalysts and gas phase reactants. In this case, there is a cycle of molecular adsorption, reaction, and desorption occurring at the catalyst surface. Thermodynamics, mass transfer, and heat transfer influence the rate (kinetics) of reaction. Heterogeneous catalysis is very important because it enables faster, large-scale production and the selective product formation. Approximately 35% of the world's GDP is influenced by catalysis. The production of 90% of chemicals (by volume) is assisted by solid catalysts. The chemical and ...
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Olefin Metathesis
Olefin metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins) by the scission and regeneration of carbon-carbon double bonds. Because of the relative simplicity of olefin metathesis, it often creates fewer undesired by-products and hazardous wastes than alternative organic reactions. For their elucidation of the reaction mechanism and their discovery of a variety of highly active catalysts, Yves Chauvin, Robert H. Grubbs, and Richard R. Schrock were collectively awarded the 2005 Nobel Prize in Chemistry. Catalysts The reaction requires metal catalysts. Most commercially important processes employ heterogeneous catalysts. The heterogeneous catalysts are often prepared by in-situ activation of a metal halides (MClx) using organoaluminium or organotin compounds, e.g. combining MClx–EtAlCl2. A typical catalyst support is alumina. Commercial catalysts are often based on molybdenum and ruthenium. Well-defined organometallic co ...
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Phillips Petroleum Company
Phillips Petroleum Company was an American oil company incorporated in 1917 that expanded into petroleum refining, marketing and transportation, natural gas gathering and the chemicals sectors. It was Phillips Petroleum that first found oil in the North Sea on December 23, 1969, at a position that was later named Ekofisk. On August 30, 2002, Conoco Inc. merged with Phillips Petroleum to form ConocoPhillips, becoming the third largest integrated energy company and second-largest refining company in the United States. The company moved its headquarters to Houston.Christopher J. Castaneda,"Phillips Petroleum Company." ''Encyclopedia of Oklahoma History and Culture''.Accessed 04 February 2013. In 2012, ConocoPhillips split into two separate companies. The legacy company kept its name, and spun off the midstream and downstream portions of its business. The new company, which owns the refinery, chemical and pipeline assets formerly held in ConocoPhillips, is named Phillips 66, the bra ...
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Catalyst
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quickly, very small amounts of catalyst often suffice; mixing, surface area, and temperature are important factors in reaction rate. Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process of regenerating the catalyst. Catalysis may be classified as either homogeneous, whose components are dispersed in the same phase (usually gaseous or liquid) as the reactant, or heterogeneous, whose components are not in the same phase. Enzymes and other biocatalysts are often considered as a third category. Catalysis is ubiquitous in chemical industry of all kinds. Estimates are that 90% of all commercially produced chemical products involve catalysts at some s ...
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Molybdenum Hexacarbonyl
Molybdenum hexacarbonyl (also called molybdenum carbonyl) is the chemical compound with the formula Mo(CO)6. This colorless solid, like its chromium and tungsten analogues, is noteworthy as a volatile, air-stable derivative of a metal in its zero oxidation state. Structure and properties Mo(CO)6 adopts an octahedral geometry consisting of six rod-like CO ligands radiating from the central Mo atom. A recurring minor debate in some chemical circles concerns the definition of an "organometallic" compound. Usually, organometallic indicates the presence of a metal directly bonded via a M–C bond to an organic fragment, which must in turn have a C–H bond. Mo(CO)6 is prepared by the reduction of molybdenum chlorides or oxides under a pressure of carbon monoxide, although it would be unusual to prepare this inexpensive compound in the laboratory. The compound is somewhat air-stable and sparingly soluble in nonpolar organic solvents. Occurrence Mo(CO)6 has been detected in landfil ...
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Tungsten Hexacarbonyl
Tungsten hexacarbonyl (also called tungsten carbonyl) is the chemical compound with the formula W(CO)6. This complex gave rise to the first example of a dihydrogen complex.Kubas, G. J., Metal Dihydrogen and σ-Bond Complexes, Kluwer Academic/Plenum Publishers: New York, 2001. This colorless compound, like its chromium and molybdenum analogs, is noteworthy as a volatile, air-stable derivative of tungsten in its zero oxidation state. Preparation, properties, and structure W(CO)6 is prepared by the reduction of tungsten hexachloride under a pressure of carbon monoxide. The compound is relatively air-stable. It is sparingly soluble in nonpolar organic solvents. Tungsten carbonyl is widely used in electron beam-induced deposition technique - it is easily vaporized and decomposed by the electron beam providing a convenient source of tungsten atoms. W(CO)6 adopts an octahedral geometry consisting of six rod-like CO ligands radiating from the central W atom with dipole moment 0 D. ...
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Molybdenum Oxide
Molybdenum oxide may refer to: * Molybdenum(IV) oxide (molybdenum dioxide, ) * Molybdenum(VI) oxide Molybdenum trioxide describes a family of inorganic compounds with the formula MoO3(H2O)n where n = 0, 1, 2. These compounds are produced on the largest scale of any molybdenum compound. The anhydrous oxide is a precursor to molybdenum metal, ... (molybdenum trioxide, ) Other stoichiometric binary molybdenum-oxygen compounds include and . References

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