96-09-3

Basic information

• Product Name: Styrene oxide
• Synonyms: NSD1 human;nuclear receptor binding SET domain protein 1;Styrene Oxide 〔1,2-Epoxyethylbenzene〕;(epoxyethyl)-benzen;(Epoxyethyl)benzene;(R,S)-2-Phenyl-oxirane;1,2-Epoxy-1-phenylethane;1-Phenyloxirane
• CAS NO: 96-09-3
• Molecular Formula: C₈H₈O
• Molecular Weight: 120.15
• EINECS: 202-476-7
• Product Categories: Organics;Oxiranes;Simple 3-Membered Ring Compounds;Aromatics;Heterocycles;Metabolites & Impurities;Aromatics, Heterocycles, Metabolites & Impurities
• Mol File: 96-09-3.mol
• Article Data: 674

Chemical Properties

• Melting Point: -37 °C
• Boiling Point: 194 °C(lit.)
• Flash Point: 175 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.054 g/mL at 25 °C(lit.)
• Vapor Density: 4.14 (vs air)
• Vapor Pressure: <1 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.535(lit.)
• Storage Temp.: 0-6°C
• Solubility: 3g/l
• Explosive Limit: 1.1-22%(V)
• Water Solubility: 3 g/L (20 ºC)
• Stability: Stability Unstable - polymerises readily with compounds possessing a labile hydrogen (such as acids and alcohols) in the presenc
• BRN: 108582
• CAS DataBase Reference: Styrene oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Styrene oxide(96-09-3)
• EPA Substance Registry System: Styrene oxide(96-09-3)

Safety Data

• Hazard Codes: T
• Statements: 45-21-36-43-36/38-20/21-46
• Safety Statements: 53-45-36/37-26
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• RTECS: CZ9625000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 96-09-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Styrene oxide is used as an important intermediate for organic synthesis, particularly in the production of various organic compounds and pharmaceuticals. It is also used in perfume production, where it is added to hydrogen to produce monophenylethanol under the action of a catalyst.
Used in Flora Fragrances and Food Industry:
Styrene oxide is used in floral fragrances for daily use products and in the food industry, adding pleasant aromas to various items.
Used in Pharmaceutical Synthesis:
Styrene oxide is an important intermediate for the synthesis of levamisole hydrochloride, a broad-spectrum intestinal repellent used by humans and animals.
Used in Epoxy Resin Industry:
Styrene oxide is used as a reactive diluent in the epoxy resin industry, contributing to the production of various epoxy resins.
Used in Chemical Intermediates:
Styrene oxide is used as a chemical intermediate for making α-phenethyl alcohol, a fragrance material, and in the production of styrene glycol and its derivatives.

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 6668, 1984 DOI: 10.1021/ja00334a035Tetrahedron Letters, 21, p. 4449, 1980 DOI: 10.1016/S0040-4039(00)92196-8

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Styrene oxide is incompatible with oxidizing agents. Also incompatible with acids and bases. Reacts with 4-(4'-nitrobenzyl)pyridine. Polymerizes exothermally and reacts vigorously with compounds possessing a labile hydrogen (e.g. alcohols and amines) in the presence of catalysts such as acids, bases and certain salts .

Hazard

Toxic by ingestion and inhalation. Possible carcinogen.

Health Hazard

Styrene oxide is a mild to moderate skin irri-tant. Irritation from 500 mg was moderateon rabbit skin. The toxicity of this com-pound was low on test animals. Inhalationof 500 ppm in 4 hours was lethal to rats. Anin vivo and in vitro study in mice (Helmanet al. 1986) indicates acute dermal toxicity,causing sublethal cell injury.LD50 value, oral (mice): 1500 mg/kgStyrene oxide, however, may present aconsiderable health hazard as a mutagen,teratogen, and carcinogen. The reproduc-tive effects from inhalation observed in ratswere fetotoxicity, developmental abnormal-ities, and effects on fertility (Sikov et al.1986). There is sufficient evidence of its car-cinogenicity in animals, producing liver, gas-trointestinal tract, and skin tumors. Gavageexposure caused cancer in the forestomach ofboth sexes of rats and mice (McConnell andSwenberg 1994). Its cancer-causing effectson humans are unknown.No exposure limit has been set for thiscompound. Its toxic and irritant effects inhumans are quite low.

Fire Hazard

Styrene oxide is combustible.

Flammability and Explosibility

Nonflammable

Potential Exposure

Styrene oxide is used as a reactive intermediate, especially to produce styrene glycol and its derivatives. Substantial amounts are also used in the epoxy resin industry as a diluent. It may also have applications in the preparation of agricultural and biological chemicals, cosmetics, and surface coatings and in the treatment of textiles and fibers. Styrene oxide is made in quantities in excess of a million pounds per year, and further, is a presumed metabolite of styrene which is produced in much greater quantities.

Carcinogenicity

Styrene-7,8-oxide is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Purification Methods

Fractional distillation under reduced pressure does not remove phenylacetaldehyde. If this material is present, the styrene oxide is treated with hydrogen under 3 atmospheres pressure in the presence of platinum oxide. The aldehyde, but not the oxide, is reduced to .-phenylethanol, and separation is now readily achieved by fractional distillation. [Schenck & Kaizermen J Am Chem Soc 75 1636 1953, Beilstein 17/1 V 577.]

Incompatibilities

Vapors may form explosive mixture with air. May polymerize on heating above 200C, under the influence of strong acids, strong bases; oxidizers, metal salts; such as aluminum chloride; catalysts for vinyl polymers. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Waste Disposal

Styrene oxide is burned in a chemical incin-erator equipped with an afterburner andscrubber.

InChI:InChI=1/C8H8O/c1-2-4-7(5-3-1)8-6-9-8/h1-5,8H,6H2

Upstream product

• 100-42-5 styrene 
• 79-21-0 peracetic acid 
• 93-59-4 Perbenzoic acid 
• 100-52-7 benzaldehyde 
• 1073-67-2 4-vinylbenzyl chloride 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 4262-61-7 acetone di-tert-butylperoxyketal 
• 2167-23-9 2,2-bis(tert-butylperoxy)butane 
• 7735-97-9 2,2-Bis-tert-butylperoxy-3-methyl-butane 
• 93-56-1 phenylethane 1,2-diol 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 57308-70-0 2-iodo-1-phenylethan-1-ol 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 75-18-3 dimethylsulfide 

Downstream Products

• 17918-11-5 1-(2'-hydroxy-2'-phenylethyl)aziridine 
• 13626-20-5 1-phenyl-2-(piperidin-1-yl)ethan-1-ol 
• 4432-34-2 2-morpholino-1-phenylethanol 
• 101722-95-6 2-(phenyl)-β-hydroxyethyl 2-napthyl sulfide 
• 4249-72-3 2-phenoxy-1-phenylethanol 
• 53574-80-4 AB_0000810 
• 22081-44-3 N-(2-hydroxy-2-phenylethyl)pyrrodidin-2-one 
• 4641-56-9 1-(2-Hydroxy-2-phenylethyl)perhydro-2-azepinon 
• 3717-77-9 2-(4-methyl-piperidin-1-yl)-1-phenyl-ethanol 
• 68239-22-5 N-(2-hydroxy-2-phenylethyl)-2,5-pyrrolidinedione 
• 4641-52-5 2-(1-Hexamethyleneimino)-1-phenylethanol 
• 23175-16-8 β-hydroxy-N-methyl-N-hydroxyethylphenylethylamine 
• 1883-32-5 2,2-diphenyl ethanol 
• 5773-56-8 1,2-Diphenylethanol 

Relevant articles and documents

Aminopropyl group-modified SBA-15 covalent attachment Mn(salen) complexes as catalysts for styrene epoxidation

A series of aminopropyl group-modified ordered mesoporous silica materials impregnated with Mn(salen) were prepared using successive grafting procedures. The prepared composite catalysts were well characterized by inductively coupled plasma atomic emissio

Epoxidation of styrene to styrene oxide: Synergism of heteropoly acid and phase-transfer catalyst under Ishii-Venturello mechanism

Epoxidation of olefinic double bonds is of considerable importance in a variety of industries. Epoxides are raw materials for a wide variety of chemicals such as glycols, alcohols, carbonyl compounds, alkanolamines, and polymers such as polyesters, polyur

Are MnIV species involved in Mn(salen)-satalyzed Jacobsen-Katsuki epoxidations? A mechanistic elucidation of their formation and reaction modes by EPR spectroscopy, mass-spectral analysis, and product studies: Chlorination versus oxygen transfer

EPR and ESI-MS/MS evidence is presented that in the absence of an olefinic substrate the reaction between the MnIII(salen) complexes A1 (X = Cl) and A2 (X = PF6) and PhIO or NaOCl as oxygen sources leads to paramagnetic MnIV(salen) complexes. Depending on the solvent and the counterion, two distinct MnIV-(salen) complexes intervene. In CH2Cl2, regardless of the counterion, a ClOMnIV(salen) complex (B1) and a HOMnIV(salen) complex (B1′) are formed by Cl and H atom abstraction from CH2Cl2, and the latter deprotonates to the neutral OMnIV(salen) complex (B2). In EtOAc as solvent, only the complex B2 is obtained from A1 (X = Cl), presumably by inner-sphere electron transfer from the chloride ion. The MnIV(salen) complexes display the following reaction modes toward 1,2-dihydronaphthalene (1), styrene (2), and the radical probe 3 as substrates: Complex B1 chlorinates the olefins 1/2 through an electrophilic pathway to yield the 1,2-dichloro adducts 1a/2a and the chlorohydrins 1b/2b (nucleophilic trapping of the initially formed benzylic cation), while with olefin 3 the ring-opened dichloro product 3a results. Complex B2, however, epoxidizes these olefins through a radical pathway, as evidenced by the formation of isomerized stilbene oxide 4c (cis/trans ratio 36: 64) from cis-stilbene (4). The relevance of these paramagnetic MnIV(salen) species in Jacobsen-Katsuki catalytic epoxidations is scrutinized.

Barium hexaferrite (BaFe12O19) nanoparticles as highly active and magnetically recoverable catalyst for selective epoxidation of styrene to styrene oxide

Herein, we are reporting the use of pure single phase barium hexaferrite (BaFe12O19) nanoparticles as an efficient catalyst for epoxidation of styrene. BaFe12O19 nanocatalysts exhibit high conversion of styrene

Gold nanoparticles supported on cellulose aerogel as a new efficient catalyst for epoxidation of styrene

A new efficient heterogeneous catalyst was introduced for the epoxidation of styrene. The catalyst was obtained from deposition of gold nanoparticles on the cellulose aerogel. The catalyst was characterized with XRD, TGA, EDX, BET, FAAS and SEM. High yield and excellent selectivity were achieved for the epoxidation of styrene in solvent-free conditions at room temperature using H2O2 as a green oxidant during 1?h. The reaction has some advantages such as solvent-free and mild reaction conditions, low catalyst loading, high yield, excellent selectivity, green oxidant and short reaction duration. In addition, the catalyst is recyclable and applicable for six times without decrease in yield.

Manganese triacetate as an efficient catalyst for bisperoxidation of styrenes

A method was developed for the bisperoxidation of styrenes with tert-butyl hydroperoxide in the presence of a catalytic amount of manganese(III) acetate. It was shown that compounds of manganese in oxidation states 2, 4, and 7 also catalyze this reaction. The target [1,2-bis(tert-butylperoxy)ethyl]arenes were synthesized in yields from 46 to 75%.

Colloidal gold immobilized on mesoporous silica as a highly active and selective catalyst for styrene epoxidation with H2O2

Colloidal gold nanoparticles were synthesized by different procedures affording suspensions with two different mean sizes (2 and 5 nm). Au catalysts were prepared by sol immobilization onto several silica frameworks with different 2D and 3D mesoporosities. The catalysts were tested in styrene oxidation reactions showing excellent efficiency and selectivity. The effect of nanoparticle size and mesoporous framework on the physical and catalytic properties of the final materials was studied. The most selective catalyst was prepared from the 5 nm Au nanoparticles and the more interconnected silica framework (3D mesoporosity).

Catalytic oxygen atom transfer promoted by tethered Mo(VI) dioxido complexes onto silica-coated magnetic nanoparticles

The preparation of three novel active and stable magnetic nanocatalysts for the selective liquid-phase oxidation of several olefins, has been reported. The heterogeneous systems are based on the coordination of cis-MoO2 moiety onto three different SCMNP@Si-(L1-L3) magnetically active supports, functionalized with silylated acylpyrazolonate ligands L1, L2 and L3. Nanocatalysts thoroughly characterized by ATR-IR spectroscopy, TGA and ICP-MS analyses, showed excellent catalytic performances in the oxidation of conjugated or unconjugated olefins either in organic or in aqueous solvents. The good magnetic properties of these catalytic systems allow their easy recyclability, from the reaction mixture, and reuse over five runs without significant decrease in the activity, either in organic or water solvent, demonstrating their versatility and robustness.

Efficient and selective oxidation of hydrocarbons with tert-butyl hydroperoxide catalyzed by oxidovanadium(IV) unsymmetrical Schiff base complex supported on γ-Fe2O3 magnetic nanoparticles

The catalytic activity of an oxidovanadium(IV) unsymmetrical Schiff base complex supported on γ-Fe2O3 magnetic nanoparticles, γ-Fe2O3@[VO(salenac-OH)] in which salenac-OH = [9-(2′,4′-dihydroxyphenyl)-5,8-diaza-4

Oxygen Atom Transfer Mechanism for Vanadium-Oxo Porphyrin Complexes Mediated Aerobic Olefin Epoxidation

The development of catalytic aerobic epoxidation by numerous metal complexes in the presence of aldehyde as a sacrificial reductant (Mukaiyama epoxidation) has been reported, however, comprehensive examination of oxygen atom transfer mechanism involving free radical and highly reactive intermediates has yet to be presented. Herein, meso-tetrakis(pentafluorophenyl) porphyrinatooxidovanadium(IV) (VOTPFPP) was prepared and proved to be efficient toward aerobic olefin epoxidation in the presence of isobutyraldehyde. In situ electron paramagnetic resonance spectroscopy (in situ EPR) showed the generation, transfer pathways and ascription of free radicals in the epoxidation. According to the spectral and computational studies, the side-on vanadium-peroxo complexes are considered as the active intermediate species in the reaction process. In the cyclohexene epoxidation catalyzed by VOTPFPP, the kinetic isotope effect value of 1.0 was obtained, indicating that epoxidation occurred via oxygen atom transfer mechanism. The mechanism was further elucidated using isotopically labeled dioxygen experiments and density functional theory (DFT) calculations.