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1. Exposure Data (C) Chemical and Physical Properties of the Pure Substance

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1. Exposure Data (C) Chemical and Physical Properties of the Pure Substance STYRENE, STYRENE-7,8-OXIDE, AND QUINOLINE VOLUME 121 This publication represents the views and expert opinions of an IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, which met in Lyon, 20–27 March 2018 LYON, FRANCE - 2019 IARC MONOGRAPHS ON THE EVALUATION OF CARCINOGENIC RISKS TO HUMANS STYRENE AND STYRENE-7,8-OXIDE 1. Exposure Data (c) Chemical and physical properties of the pure substance 1.1 Styrene Description: Colourless, viscous liquid with a 1.1.1 Identification of the agent pungent odour (WHO, 1983) Melting/freezing point: −31 °C (IARC, 2002) (a) Nomenclature Boiling point: 145 °C at 101.3 kPa (IARC, Chem. Abstr. Serv. Reg. No.: 100-42-5 2002) 3 Previously used Chem. Abstr. Serv. Reg. No.: Density: 0.906 g/cm at 25 °C (Merck, 2017a) 79637-11-9 Relative density: d20/4, 0.9060 (water, 1) (IARC, Chem. Abstr. Serv. name: Ethenylbenzene 2002) IUPAC systematic name: Styrene Solubility in organic solvents: Miscible with acetone, benzene, carbon tetrachloride, Synonyms: Cinnamene; cinnamenol; cinnamol; (diethyl) ether, ethanol, heptane (Chevron phenylethene; phenethylene; phenylethylene; Phillips Chemical Co., 2010) styrol; styrole; styrolene; vinylbenzene; vinylbenzol Solubility in water: 0.31 g/L at 25 °C (NTP, 2016a) (b) Structural and molecular formulae, and Vapour pressure: 867 Pa at 25 °C (IARC, 2002) relative molecular mass Saturated vapour concentration: 8500 ppm at 25 °C (EPA, 1993) Relative vapour density: 3.6 (air, 1) (IARC, 2002) Evaporation rate: 1.92 (nBuAc, 1) (Chevron Styrene Phillips Chemical Co., 2010) Molecular formula: C8H8 Odour threshold: Low: 0.20 mg/m3 (pure) Relative molecular mass: 104.15 and 0.43 mg/m3 (stabilized); high: 860 mg/m3 (Ruth, 1986) Reactivity: Polymerizes readily at room temperature in the presence of oxygen and oxidizes on exposure to light and air (WHO, 1983). Styrene is stabilized by a small amount 37 IARC MONOGRAPHS – 121 of a polymerization inhibitor; if this is not present in adequate concentration, styrene Table 1.1 Trace components present in commercially produced styrene can polymerize and explode its container. Polymerization is also accelerated at temper- Trace chemical Concentration (ppm) atures above 66 °C (NIOSH, 1983); recom- α-methylstyrene 175 mended storage temperature is 25 °C or less Σ m- and p-xylene 120 (Shell, 2017). The vapours are heavier than air o-xylene 125 and spread along the ground; distant ignition Cumene 100 is possible (Shell, 2017). Propylbenzene 60 Ethylbenzene 50 Octanol/water partition coefficient (P): Phenylacetylene 50 log Kow, 2.95 (IARC, 2002) Σ m- and p-ethyltoluene 20 Conversion factor: 1 ppm = 4.26 mg/m3 at Aldehydes (as benzaldehyde) 15 normal temperature (25 °C) and pressure 4-tert-butylcatechol 12 (101 kPa) (IARC, 2002) Vinyltoluene 10 Σ m- and p-divinylbenzene < 10 Peroxides (as benzoyl peroxides) 5 (d) Technical products and impurities o-divinylbenzene < 5 Styrene monomer is available as a commer- Polymerized styrene 1 Benzene < 1 cial product with different levels of purity (i.e., Chlorides (as Cl) < 1 99.7% to >99.9%) The impurities present and their Sulfur < 1 concentrations depend upon the manufacturing Toluene < 1 route, as well as plant performance characteris- ppm, parts per million. tics. The typical inhibitor content of the standard Adapted from Chevron Phillips Chemical Co. (2010). grade is 10–15 ppm 4-tert-butylcatechol (CEFIC, 2007). The trace components in a commercial There are two commercially viable methods product of purity 99.93% are listed in Table 1.1 of producing styrene. The most important, (Chevron Phillips Chemical Co., 2010). which accounts for over 90% of total world styrene production, is catalytic dehydrogenation 1.1.2 Production and use of styrene in the vapour phase of high-purity ethylbenzene. Common catalysts are based on ferric oxide Worldwide, styrene is one of the most impor- (Fe2O3) with chromia (Cr2O3) as a stabilizer and tant monomers for polymers and copolymers potassium oxide as a coke retardant (Behr, 2017). that are used in a wide range of applications. Typically, the crude product of the dehydrogena- Globally, it is estimated that more than 15 000 tion process consists of 64% styrene, 32% ethylb- industrial plants in many countries produce or enzene, 2% toluene, 1% benzene, and 1% other use styrene in the manufacturing of polymeric substances. The isolation of pure styrene from products (The Styrene Forum, 2017). the mixture by distillations is difficult because of the similar boiling points of styrene and ethyl- (a) Production process benzene (Behr, 2017). Styrene was first isolated in 1831 by distil- The second process involves oxidation of lation of storax, a natural balsam. Commercial ethylbenzene to its hydroperoxide and reaction production of styrene via dehydrogenation with propylene to yield propylene oxide. The of ethylbenzene began in Germany in 1925 co-product α-methylphenyl carbinol is then (Tossavainen, 1978). dehydrated to styrene (Behr, 2017). A third 38 Styrene and styrene-7,8-oxide process, involving oxidative dehydrogenation of of styrene in 2006 was 9600 million pounds ethylbenzene to styrene with carbon dioxide, has [~43 × 105 tonnes], more than 99% of which was been proposed (Chon, 2003). in the production of polymers and copolymers (NTP, 2016a). (b) Production volume The USA is a producer and net exporter of Styrene is considered to be a high produc- styrene to the rest of the world. In 2014, the tion volume chemical (USDOE, 2012). In 2004, production capacity of styrene in Canada the global styrene demand was reported to be and the USA was 880 thousand tonnes and over 24 million metric tonnes (CEFIC, 2007). 4.8 million tonnes, respectively. The amount of In 2010, the global production of styrene was styrene imported into the USA recently has been 27.5 million United States tons [25 million small, and only from Canada. In 2014, the USA tonnes], of which approximately 4.4 million exported 1.53 million tonnes of styrene (ICIS, United States tons [4 million tonnes] originated 2014). in the USA. In 2012, the world production of In 2016, 1 767 053 metric tons of styrene mono- styrene monomer exceeded 26.4 million metric mer was produced in Japan (Statista, 2017). tonnes (Aghayarzadeh et al., 2014). In 2016, China imported 3.5 million tonnes China consumes far more styrene than other of styrene monomer; 1.23 million tonnes (35%) countries. In 2014, 30% of the world consump- of this quantity came from the Republic of Korea, tion of styrene was estimated to be by China (IHS making it the largest supplier of styrene monomer Markit, 2017). Styrene consumption is expected to China. Meanwhile, China’s total styrene to remain relatively constant, growing at an monomer demand has gradually increased from average rate of 1.6% per year during 2014–2019. 8.49 million tonnes in 2013 to 9.1 million tonnes Higher growth in the production of expand- in 2016, at an average annual growth rate of able polystyrene (EPS) is predicted, especially 2.38%. According to industry sources, China’s in construction where it is being increasingly annual domestic styrene monomer production used as concrete forms and as insulation, driven was about 8.39 million tonnes in 2017, and was by demand for higher energy efficiency. Styrene expected to rise by 2.3 million tonnes per year consumption for EPS production is expected to to 10.7 million tonnes by 2019 (Plastemart.com, grow at an average rate of 2.3% per year during 2017). 2019–2024. Styrene consumption for the produc- Styrene is presently manufactured in and/or tion of acrylonitrile–butadiene–styrene (ABS) imported into the European Economic Area at resins and styrene–butadiene rubber (SBR) is a rate of 1–10 million tonnes per year (ECHA, expected to see the highest annual growth rates 2017). of 3.6% and 4.1%, respectively (IHS Markit, 2017). (c) Uses The production of styrene in the USA has risen steadily since 1960. Between 1960 and In the 1930s, styrene was used mainly in the 2006, estimated production ranged from a low of production of synthetic rubber; the application 1740 million pounds [~7.9 × 105 tonnes] in 1960 of styrene as a solvent and cross-linking agent to a high of 11 897 million pounds [~54 × 105 in the production of fibreglass-reinforced plas- tonnes] in 2000. In 2006, eight United States tics started in the 1950s (Tossavainen, 1978). manufacturers produced an estimated 11 387 The resins generally contain between 30% and million pounds [~51 × 105 tonnes] of styrene; 50% styrene by weight (Haberlein, 1998). Today, the three largest producers accounted for 54% styrene is primarily used as a monomer in the of production. United States consumption production of polystyrene plastics and resins. 39 IARC MONOGRAPHS – 121 Styrene producers sell styrene monomer to 1.2 Styrene-7,8-oxide companies that use styrene to make various compounds and resins. Fabricators then process 1.2.1 Identification of the agent the resins into a wide variety of products (Cohen (a) Nomenclature et al., 2002). According to The Styrene Forum (2017), there Chem. Abstr. Serv. Reg. No.: 96-09-3; (R)-(+)- are six major styrene resin families: (i) polysty- styrene-7,8-oxide: 20780-53-4; (S)-(-)- rene (PS); (ii) SBR; (iii) styrene–butadiene latex styrene-7,8-oxide: 20780-54-5; (±)-styrene- (SBL); (iv) ABS; (v) styrene-based unsaturated 7,8-oxide: 67253-49-0 polyester resins (UPR); and (vi) styrene–acry- Previously used Chem. Abstr. Serv. Reg. No.: lonitrile (SAN). Industry estimates of the relative 62497-63-6 amounts of styrene consumed by these six resin Chem. Abstr. Serv. name: 2-Phenyloxirane families are as follows: PS, 50%; SBR, 15%; SBL, 12%; ABS, 11%; UPR, 11%; and SAN, 1% (The Synonyms: Epoxyethylbenzene; 1,2-(epoxy- Styrene Forum, 2017).
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