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Encyclopedia > Styrene
Styrene
Styrene
General
Systematic name Phenylethene
Other names Vinyl benzene,
cinnamene
styrol
ethenylbenzene
phenethylene
phenylethene
cinnamene
diarex HF 77
styrolene
styropol
Molecular formula C8H8
SMILES c1ccccc1C=C
Molar mass 104.15 g/mol
Appearance colourless oily liquid
CAS number [100-42-5]
Properties
Density and phase 0.9 g/cm³
Solubility in water < 1%
Melting point -30 °C (243.15 K)
Boiling point 145 °C (418.15 K)
Viscosity  ? cP at ? °C
Structure
Molecular shape  ?
Dipole moment  ? D
Hazards
MSDS MSDS
Main hazards flammable, toxic
Flash point 31 °C
R/S statement R: 10-36 S: 38-20-23
RTECS number  ?
Supplementary data page
Structure & properties n, εr, etc.
Thermodynamic data Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Related styrenes Polystyrene
Stilbene
Related aromatics Ethylbenzene
Except where noted otherwise, data are given for
materials in their standard state (at 25°C, 100 kPa)
Infobox disclaimer and references

"C8H8" redirects here. For a compound with an identical formula see cubane. Image File history File links Styrene. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... This article describes water from a scientific and technical perspective. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... The pitch drop experiment at the University of Queensland. ... The poise (P) is the cgs unit of viscosity, 1 P = 1 g·cm-1·s-1 The SI analog is 1 pascal second (Pa·s) = 1 kg·m-1·s-1 = 10 P. It is named after Jean Louis Marie Poiseuille. ... four sp³ orbitals three sp² orbitals In chemistry, hybridisation or hybridization (see spelling differences) is the mixing of atomic orbitals belonging to a same electron shell to form new orbitals suitable for the qualitative description of atomic bonding properties. ... // The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... The examples and perspective in this article or section may not represent a worldwide view. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The refractive index (or index of refraction) of a material is the factor by which the phase velocity of electromagnetic radiation is slowed in that material, relative to its velocity in a vacuum. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... IR spectrum of a thin film of liquid ethanol. ... Nuclear Magnetic Resonance Spectroscopy most commonly known as NMR Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... Basic schematic of a mass spectrometer Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or in common speech mass-spec) is an analytical technique used to measure the mass-to-charge ratio of ions. ... Polystyrene is a polymer made from the monomer styrene, a liquid hydrocarbon that is commercially manufactured from petroleum. ... Stilbene is a colorless or yellowish crystalline compound. ... In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ... Chemical Structure of Ethylbenzene Ethylbenzene is an organic chemical compound which is an aromatic hydrocarbon with the chemical formula C8H10. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ...


Styrene, also known as vinyl benzene as well as many other names (see table), is an organic compound with the chemical formula C6H5CH=CH2. Under normal conditions, this aromatic hydrocarbon is an oily liquid. It evaporates easily and has a sweet smell. It often contains other chemicals that can result in a sharp, unpleasant smell. Benzene An organic compound is any member of a large class of chemical compounds whose molecules contain carbon, with the exception of carbides, carbonates, carbon oxides and elementary carbon. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... An aromatic hydrocarbon (abbreviated as AH) or arene [1] is a hydrocarbon, the molecular structure of which incorporates one or more planar sets of six carbon atoms that are connected by delocalised electrons numbering the same as if they consisted of alternating single and double covalent bonds. ... A liquid will usually assume the shape of its container. ...

Contents

Occurence and history

Low levels of styrene also occur naturally in plants as well as a variety of foods such as fruits, vegetables, nuts, beverages, and meats. It is produced in industrial quantities from benzene and ethylene via the intermediate ethylbenzene. The production of styrene in the United States was increased dramatically during the 1940's to supply the war needs for synthetic rubber. Because the styrene molecule has a vinyl group with a double bond, it can polymerize. It is used as a monomer to make plastics such as polystyrene, ABS, styrene-butadiene (SBS) rubber, styrene-butadiene latex, SIS (styrene-isoprene-styrene), S-EB-S (styrene-ethylene/butylene-styrene), styrene-divinylbenzene (S-DVB), and unsaturated polyesters. These materials are used in rubber, plastic, insulation, fiberglass, pipes, automobile parts, food containers, and carpet backing. Benzene, also known as benzol, is an organic chemical compound with the formula C6H6. ... Ethylene (or IUPAC name ethene) is the simplest alkene hydrocarbon, consisting of four hydrogen atoms and two carbon atoms connected by a double bond. ... Chemical Structure of Ethylbenzene Ethylbenzene is an organic chemical compound which is an aromatic hydrocarbon with the chemical formula C8H10. ... In chemistry, a molecule is an aggregate of at least two atoms in a definite arrangement held together by special forces. ... Vinyl products (such as these records) come in many colors. ... Covalent bonding is a form of chemical bonding characterized by the sharing of one or more pairs of electrons between atoms, in order to produce a mutual attraction, which holds the resultant molecule together. ... Polymerization is a process of reacting monomer molecules together in a chemical reaction to forinear chains or a three-dimensional network of polymer chains [1]. There are many forms of polymerization and different systems exist to categorize them. ... In chemistry, a monomer (from Greek mono one and meros part) is a small molecule that may become chemically bonded to other monomers to form a polymer. ... Polystyrene is a polymer made from the monomer styrene, a liquid hydrocarbon that is commercially manufactured from petroleum. ... Monomers in ABS polymer Acrylonitrile butadiene styrene, or ABS, (chemical formula (C8H8· C4H6·C3H3N)x) is a common thermoplastic used to make light, rigid, molded products such as pipes, golf club heads (used for its good shock absorbance), automotive body parts, wheel covers, enclosures, protective head gear, and toys including... Styrene Butadiene SBR (SBR) is a polymeride consisting of styrene and butadiene. ... Latex being collected from a tapped rubber tree Rubber is an elastic hydrocarbon polymer which occurs as a milky colloidal suspension (known as latex) in the sap of several varieties of plants. ... It has been suggested that History of fiberglass be merged into this article or section. ... Karl Benzs Velo model (1894) - entered into the first automobile race An automobile (or motor car) is a wheeled passenger vehicle that carries its own motor. ...


Production

Dehydrogenation of ethylbenzene

Styrene is most commonly produced by the catalytic dehydrogenation of ethylbenzene. Ethylbenzene is mixed in the gas phase with 10–15 times its volume in high-temperature steam, and passed over a solid catalyst bed. Most ethylbenzene dehydrogenation catalysts are based on iron(III) oxide, promoted by several percent potassium oxide or potassium carbonate. On this catalyst, an endothermic, reversible chemical reaction takes place. It has been suggested that this article or section be merged into Catalysis. ... Hydrogenation is a chemical reaction in which unsaturated bonds between carbon atoms are reduced by attachment of a hydrogen atom to each carbon. ... Chemical Structure of Ethylbenzene Ethylbenzene is an organic chemical compound which is an aromatic hydrocarbon with the chemical formula C8H10. ... In physical chemistry, and in engineering, steam refers to vaporized water. ... Iron(III) oxide — also known as ferric oxide, Hematite, red iron oxide, synthetic maghemite, colcothar, or simply rust — is one of several oxide compounds of iron, and is most notable for its ferromagnetic properties. ... Potassium oxide is a compound of potassium and oxygen used mainly as a intermediate in inorganic synthesis. ... Carbonate of potash redirects here. ... Endothermic can mean: In biology, an endotherm is a type of animal that can control its body temperature. ... A reversible reaction is a chemical reaction that may proceed in both the forward and reverse directions. ... A chemical reaction occurs when vapours of hydrogen chloride and ammonia meet to form a cloud of a new substance, ammonium chloride Chemical reaction is a process that results in the interconversion of chemical substances [1]. The substance or substances initially involved in a chemical reaction are called reactants. ...

Ethylbenzene Image: ctk-arrow-eq.png Styrene Image: ctk-plus.png Hydrogen

Steam serves several roles in this reaction. It is the source of heat for powering the endothermic reaction and it continuously removes coke that tends to form on the iron oxide catalyst through the water/gas shift reaction C + 2H2O --> CO2 + 2H2. The potassium promoter on the catalyst is present to enhance this decoking reaction. The steam injected with the reactor feed also dilutes the concentration of the reactant and products in the reaction mixture, shifting the position of chemical equilibrium towards products. A typical styrene plant operates two or three reactors in series and operates under vacuum conditions to enhance the conversion and selectivity of the reaction. Typical per-pass conversions are on the order of 65% if two reactors are used and 70% to 75% if three reactors are used. Selectivity to styrene is 93% to as high as 97% depending upon reactor operating pressure, catalyst and conversion. The main byproducts of the reaction are benzene and toluene, these are somewhat easily removed by distillation. The separation of styrene from the remaining ethylbenzene requires tall distillation towers and high reflux ratios, because styrene and ethylbenzene have similar boiling points (145 °C for styrene, 136 °C for ethylbenzene). Distillation and separation of the crude styrene into product styrene is also complicated by the fact that the temperatures involved in the distillation of styrene initiate the polymerization of the styrene. To combat this, early styrene plants added elemental sulfur to inhibit the rate of polymerization. During the 1970's additive chemicals consisting of phenol based retarders were developed. These and the more recently developed free radical inhibitor chemicals are now added prior to distillation. These additives limit the rate of polymerization and allow for the separation and purification of the product styrene. Flash point 15-20 °C R/S statement R: 11, 20 S: 2, 16, 24/25, 29 RTECS number DA0700000 Supplementary data page Structure and properties n, εr, etc. ... Image File history File links Ctk-arrow-eq. ... Styrene (also vinyl benzene, ethenylbenzene, phenethylene or phenylethene, cinnamene, diarex HF 77, styrolene, styrol, styropol) is an organic compound which is an aromatic hydrocarbon having the chemical formula C8H8. ... Image File history File links Ctk-plus. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... Chemical equilibrium is the state in which the concentrations of the reactants and products have no net change over time. ...


Improving conversion and so reducing the amount of ethylbenzene that must be separated is the chief impetus for researching alternative routes to styrene. Other than the POSM process, none of these routes like obtaining styrene from butadiene have been commercially demonstrated.


Via ethylbenzenehydroperoxide

Commercially styrene is also co-produced with propylene oxide in a process known as POSM for Propylene Oxide / Styrene Monomer. In this process ethylbenzene is reacted with oxygen to form the hydroperoxide of ethylbenzene. This hydroperoxide is then used to oxidize propylene to propylene oxide. The resulting phenylethanol is dehydrated to give styrene: Propylene, also known by its IUPAC name propene, is an organic compound having the chemical formula C3H6. ...

C6H5CH2CH3 + O2 → C6H5CH2CH2O2H
C6H5CH2CH2O2H + CH3CH=CH2 → C6H5CH2CH2OH + CH3CHCH2O
C6H5CH2CH2OH → C6H5CH=CH2 + H2O

Propylene oxide is a highly toxic flammable chemical compound. ...

Laboratory synthesis

A laboratory synthesis of styrene entails the decarboxylation of cinnamic acid.[1] A Decarboxylation is any chemical reaction in which a carboxyl group (-COOH) is split off from a compound as carbon dioxide (CO2). ... Cinnamic acid Cinnamic acid has the formula C6H5CHCHCOOH and is an odorless white crystalline acid, which is slightly soluble in water. ...


Health effects

Styrene is a toxin, an irritant, and a potential carcinogen. See MSDS. In pathology, a carcinogen is any substance or agent that promotes cancer. ...


References

  1. ^ Abbott, T. W.; Johnson, J. R. "Phenylethylene [Styrene]" Organic Syntheses, Coll. Vol. 1, p.440 (1941).

External links

  • Link page to external chemical sources.

  Results from FactBites:
 
ATSDR - ToxFAQs™: Styrene (956 words)
Styrene is a colorless liquid that evaporates easily and has a sweet smell.
Styrene evaporates from shallow soils and surface water.
Styrene that remains in soil or water may be broken down by bacteria or other microorganisms.
  More results at FactBites »

 
 

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