9003-53-6

Usage

Uses

Used in Packaging Industry:
Poly(styrene) is used as a packaging material for food items, such as containers, tubs, and trays, due to its lightweight, insulation, and clarity properties. It is also used in the production of blister packs, meat trays, container lids, and cookie, candy, pastry, and other food packages where clarity is required.
Used in Housewares Industry:
Poly(styrene) is used as a material for refrigerator door liners and furniture panels due to its rigidity and ease of thermoforming. Extruded profiles of solid or foamed impact polystyrene are used for mirror or picture frames, and moldings for construction applications.
Used in General-Purpose Applications:
Poly(styrene) is extruded either clear or embossed for room dividers, shower doors, glazings, and lighting applications. Injection molding of impact polystyrene is used for household items, such as flower pots, personal care products, and toys.
Used in Consumer Electronics Industry:
Poly(styrene) is used in the production of cassettes, reels, and housings for consumer electronics due to its ease of processing and decorability.
Used in Medical Applications:
Poly(styrene) is used for sample collectors, petri dishes, and test tubes in the medical field due to its clarity and rigidity.
Used in Construction Industry:
Poly(styrene) is used in extruded foam board with flame-retardant additives for walls and under slabs to make homes and other buildings more energy efficient. It also complies with the requirements of major building codes, as well as federal and military specifications.
Used in Various Other Industries:
Poly(styrene) latex microspheres are utilized in flow cytometry, fluorescence microscopy, and as calibration particles. It is also employed as a stimulus responsive particulate emulsifier for oil-in-water emulsion. Other uses include packaging film, molded parts for automobiles, appliances, housewares, wire and cable coating, food container closures, coated and laminated products, bottles, artificial grass and turfs, plastic pipe, wearing apparel (acid-dyed), fish nets, surgical casts, strapping, synthetic paper, reinforced plastics, and nonwoven disposable filters.

Preparation

Styrene may be polymerized by means of all four techniques by bulk, solution, suspension and emulsion polymerization. Each of these methods is practised commercially, but solution polymerization is now the most extensively used. The four processes are described below.(a) Bulk polymerization In a common type of process, styrene is partially polymerized batch-wise by heating the monomer (without added initiator) in large vessels at about 80°C for 2 days until about 35% conversion is attained. The viscous solution of polymer in monomer is then fed continuously into the top of a tower which is some 25 feet high. The top of the tower is maintained at a temperature of about 100°C, the centre at about 150°C and the bottom at about 180°C. As the feed material traverses the temperature gradient, polymerization occurs and fully polymerized material emerges from the base of the tower. The reaction is controlled by a complex array of heating and cooling jackets and coils with which the tower is fitted. The molten material is fed into an extruder, extruded as filament and then cooled and chopped into granules. Since the product contains few impurities, it has high clarity and good electrical insulation properties. The polymer has a broader molecular weight distribution than polymer prepared at one temperature.(b) Solution polymerization Continuous solution processes have found wide commercial utilization, the main advantage over bulk methods being a lessening of the problems associated with the movement and heat transfer of viscous masses. However, the technique does require the added steps of solvent removal and recovery. Typically, a mixture of monomer, solvent (3-12% ethylbenzene) and initiator is fed into a train of three polymerization reactors, each with several heating zones. The reaction temperature is progressively increased, rising from 110-130°C in the first reactor to 150-170°C in the last. The polymer solution is then extruded as fine strands into a devolatilizing vessel. In this vessel, which is at a temperature of 225°C, removal of solvent and unreacted monomer takes place, being aided by the large surface area of the strands. The molten material is fed into an extruder, extruded as filament, cooled and chopped. It may be noted that this type of process is commonly regarded as a continuous bulk process since the amount of solvent used is so small.(c) Suspension polymerization Suspension processes simplify the heat transfer problems associated with bulk methods and, unlike solution methods, they do not involve solvent removal and recovery. The disadvantages of the suspension technique are that it requires the added step of drying and it does not readily lend itself to continuous operation. Typically, polymerization is carried out batch-wise in a stirred reactor, jacketed for heating and cooling.Reaction temperature is about 90°C. When polymerization is complete, the product, in the form of a slurry, is washed with hydrochloric acid and water to remove suspending agent, centrifuged, dried in warm air (at about 60°C), extruded and chopped. (d) Emulsion polymerization Emulsion processes are not used for making solid grades of polystyrene. This is because these processes lead to polymer containing large quantities of soap residues which impair the electrical insulation properties and optical clarity. Emulsion polymerization does, however, find limited application in the production of polystyrene latex used in water-based surface coatings. The techniques employed are very similar to those used for other polymer latices, e.g. poly(vinyl acetate) latex.

Hazard

Questionable carcinogen.

Safety Profile

Questionable carcinogen with experimental tumorigenic data by implant. When heated to decomposition it emits acrid smoke and irritating fumes. See also POLYMERS, IN SOLUBLE.

Purification Methods

Precipitate polystyrene repeatedly from CHCl3 or toluene solution by addition of MeOH. Dry it in vacuo. [Miyasaka et al. J Phys Chem 92 249 1988.]

InChI:InChI=1/C9H8/c1-8(2)9-6-4-3-5-7-9/h1-8H

Upstream product

• 689-97-4 3-buten-1-yne 
• 67-56-1 methanol 
• 111-34-2 -butyl vinyl ether 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 116999-34-9 dimethyl(1-phenylethyl)sulfonium iodide 
• 28289-44-3 dimethyl-phenethyl sulfonium ; iodide 
• 107-01-7 butene-2 
• 57362-02-4 [1-(phenyl)ethyl] ethyl carbonate 
• 60-12-8 2-phenylethanol 
• 140-10-3 (E)-3-phenylacrylic acid 
• 4173-52-8 2,2,3-triphenylcyclobutanone 
• 5441-68-9 α-phenyl-β-bromopropionic acid 

Downstream Products

• 39657-33-5 2-methyl-1-phenethyl-aziridine 
• 57308-70-0 2-iodo-1-phenylethan-1-ol 
• 13684-98-5 2-methoxy-2-phenylethyl iodide 
• 52763-05-0 (2-chloro-1-phenyl-ethyl)-propyl ether 
• 18624-59-4 β-Chlor-α-phenyl-α-methylthio-ethan 
• 18624-58-3 1-chloro-2-methylthio-1-phenylethane 
• 3740-49-6 1,1,1,3-tetrabromo-3-phenylpropane 
• 850481-05-9 N,N'-bis(2-phenylethyl)hexane-1,6-diamine 
• 857764-98-8 3-chloro-3-phenylpropanoic acid chloride 
• 4537-11-5 (1-butylhexyl)benzene 
• 102470-69-9 bis-(6-phenyl-dihydro-[1,3]oxazin-3-yl)-methane 
• 18792-80-8 1-phenylbenzanthrone 
• 19798-87-9 tetrahydro-3-methyl-6-phenyl-2H-1,3-oxazine 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 

Relevant academic research and scientific papers

Photoredox Catalyzed Sulfonylation of Multisubstituted Allenes with Ru(bpy)3Cl2 or Rhodamine B

A highly regio- and stereoselective sulfonylation of allenes was developed that provided direct access to α, β-substituted unsaturated sulfone. By means of visible-light photoredox catalysis, the free radicals produced by p-toluenesulfonic acid reacted with multisubstituted allenes to obtain Markovnikov-type vinyl sulfones with Ru(bpy)3Cl2 or Rhodamine B as photocatalyst. The yield of this reaction could reach up to 91%. A series of unsaturated sulfones would be used for further transformation to some valuable compounds.

Selective C(sp3)?N Bond Cleavage of N,N-Dialkyl Tertiary Amines with the Loss of a Large Alkyl Group via an SN1 Pathway

Polar disconnection of the C(sp3)?N bond of N,N-dialkyl-substituted tertiary amines via ammonium species conventionally favored the loss of the smaller alkyl group by an SN2 displacement, while selective C(sp3)?N bond cleavage by cutting off the larger alkyl group is still underdeveloped. Herein, we present a novel Pd0-catalyzed [2+2+1] annulation, proceeding through an alkyne-directed palladacycle formation and consecutive diamination with a tertiary hydroxylamine by cleaving its N?O bond and one C(sp3)?N bond, for the rapid assembly of tricyclic indoles in a single-step transformation. Noteworthy, experimental results indicated that large tert-butyl and benzyl groups were selectively cleaved via an SN1 pathway, in the presence of a smaller alkyl group (Me, Et, iPr). Under the guidance of this new finding, tricyclic indoles bearing a removable alkyl group could be exclusively obtained by using a (α-methyl)benzyl/benzyl or tert-butyl/2-(methoxycarbonyl)ethyl mixed amino source.

Mild and efficient desulfurization of thiiranes with MoCl5/Zn system

Desulfurization of a variety of thiiranes to alkenes occurs chemoselectively in high yields upon treatment with MoCl5/Zn system under mild conditions. The new methodology demonstrates high functional group tolerance toward chloro, bromo, fluoro, methoxy, ester, ether and keto groups.

Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold

The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)3 is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts. This journal is

Oxidative Alkenylation of Arenes Using Supported Rh Materials: Evidence that Active Catalysts are Formed by Rh Leaching

This work focuses on the synthesis of supported Rh materials and study of their efficacy as pre-catalysts for the oxidative alkenylation of arenes. Rhodium particles supported on silica (Rh/SiO2; ～3.6 wt% Rh) and on nitrogen-doped carbon (Rh/NC

Heterogeneously Catalyzed Selective Decarbonylation of Aldehydes by CeO2-Supported Highly Dispersed Non-Electron-Rich Ni(0) Nanospecies

Aldehyde decarbonylation has been extensively investigated, primarily using noble-metal catalysts; however, nonprecious-base-metal-catalyzed aldehyde decarbonylation has been hardly reported. We have established an efficient selective aldehyde decarbonylation reaction with a broad substrate scope and functional group tolerance utilizing a heterogeneous Ni(0) nanospecies catalyst supported on CeO2. The high catalytic performance is attributable to the highly dispersed and non-electron-rich Ni(0) nanospecies, which possibly suppress a side reaction producing esters and adsorbed CO-derived inhibition of the catalytic turnover, according to detailed catalyst characterization and kinetic evaluation.

Palladium nanoparticlesin situsynthesized onCyclea barbatapectin as a heterogeneous catalyst for Heck coupling in water, the reduction of nitrophenols and alkynes

This study develops an effective method for thein situsynthesis of palladium nanoparticles (PdNPs) usingCyclea barbatapectin as a green reducing and stabilizing reagent. The PdNP@pectin nanocomposite was well characterized by analysis techniques such as UV-vis, FTIR, EDX, XRD, SEM, HR-TEM and STEM-mapping. Crystalline PdNPs were found to be distributed in the size range of 1-25 nm with the highest frequency of 6-12 nm. PdNP@pectin exhibited excellent recyclable catalysis activity for the Heck coupling reaction in water medium. The kinetics and recyclability of nanoparticles were investigated for the catalytic reduction ofo-,m- andp-nitrophenol. The result showed a good catalysis efficiency with five successful recycles without compromising much. In particular, the nanocomposite was used as a catalyst for the conversion of alkynes intocis-alkenes with KOH/DMF as a hydrogenation source. The reaction was also utilized effectively for the synthesis of sex pheromones, includingPlutella xylostella((Z)-11-hexadecen-1-yl acetate) andCylas formicarius((Z)-3-dodecen-1-yl(E)-2-butenoate) with the total yields of 70% and 68%, respectively. Therefore, PdNPs supported onC. barbatapectin are promising catalysis materials for application in various fields.

A stable well-defined copper hydride cluster consolidated with hemilabile phosphines

Copper hydrides are very useful in hydrogenation reactions. We report a stable Stryker-type copper hydride reagent protected by hemilabile phosphines: [Cu8H6(dppy)6](OTf)2(Cu8-H, dppy = diphenylphosphino-2-pyridine). The metal core of this cluster has a bicapped octahedral configuration, and the copper-bound hydrides each triply bridges over a triangular face of the octahedron. This cluster is attractive due to its facile preparation and excellent stability under ambient conditions. The comparable activity and selectivity both in the stoichiometric and catalytic reactions makeCu8-Ha promising alternative to Stryker's reagent.

Preparation of Recyclable and Versatile Porous Poly(aryl thioether)s by Reversible Pd-Catalyzed C–S/C–S Metathesis

Porous organic materials (polymers and COFs) have shown a number of promising properties; however, the lability of their linkages often limits their robustness and can hamper downstream industrial application. Inspired by the outstanding chemical, mechanical, and thermal resistance of the 1D polymer poly(phenylene sulfide) (PPS), we have designed a new family of porous poly(aryl thioether)s, synthesized via a mild Pd-catalyzed C–S/C–S metathesis-based method, that merges the attractive features common to porous polymers and PPS in a single material. In addition, the method is highly modular, allowing to easily introduce application-oriented functionalities in the materials for a series of environmentally relevant applications including metal capture, metal sensing, and heterogeneous catalysis. Moreover, despite their extreme chemical resistance, the polymers can be easily recycled to recover the original monomers, offering an attractive perspective for their sustainable use. In a broader context, these results clearly demonstrate the untapped potential of emerging single-bond metathesis reactions in the preparation of new, recyclable materials.

Selective continuous flow phenylacetylene hydrogenation over Pd-biogenic calcium carbonate

CaCO3 obtained from Sporosarcina pasteurii isolated from agricultural soils has been employed as catalytic support for Pd that was subsequently loaded on CaCO3 by wet impregnation with a metal loading of 0.5 wt.% using Palladium acet