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Isobutyl Nitrite, Β-Picoline, and Some Acrylates Volume 122

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Isobutyl Nitrite, Β-Picoline, and Some Acrylates Volume 122 ISOBUTYL NITRITE, β-PICOLINE, AND SOME ACRYLATES VOLUME 122 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, 5–12 June 2018 LYON, FRANCE - 2019 IARC MONOGRAPHS ON THE EVALUATION OF CARCINOGENIC RISKS TO HUMANS 2-ETHYLHEXYL ACRYLATE 1. Exposure Data 1.1.3 Chemical and physical properties 1.1 Identification of the agent Description: colourless liquid (HSDB, 2018) Boiling point: 214–218 °C (HSDB, 2018) 1.1.1 Nomenclature Melting point: −90 °C (HSDB, 2018) Density: specific gravity, 0.880 g/cm3 at 25 °C Chem. Abstr. Serv. Reg. No.: 103-11-7 (HSDB, 2018) Deleted Chem. Abstr. Serv. Reg. Nos: 78733- Solubility: slightly soluble in water (< 0.01% 32-1; 84948-57-2; 93460-77-6 by weight, wt%, at 20 °C); soluble in alcohols, Chem. Abstr. Serv. name: 2-propenoic acid; ethers, and many organic solvents (acetone, 2-ethylhexyl ester benzene, ethyl ether, heptane, methanol, and IUPAC systematic name: acrylic acid; 2-ethyl- carbon tetrachloride) (Union Carbide Corp., hexyl ester 1982) Synonyms: 2-ethylhexyl 2-propenoate; 2- Vapour pressure: 0.14 mm Hg [19 Pa] at 20 °C ethyl hexyl acrylate; 2-ethyl-1-hexyl acrylate; Relative vapour density (air = 1): 6.4 at 20 °C 2-ethylhexanol acrylate; 2-ethylhexyl prop- (Hoechst Celanese Corp., 1992) 2-enoate. Flash point: 92 °C (open cup); rapid, uncon- trolled polymerization can cause explosion 1.1.2 Structural and molecular formulae, and (Tyler, 1993) relative molecular mass Conversion factor: 1 ppm = 7.54 mg/m3 at 1 atm, 25 °C. Molecular formula: C11H20O2 O 1.1.4 Technical products and impurities CH2 2-Ethylhexyl acrylate is available as a H3CO commercial product with a purity of 99% or greater. Impurities include: water, 0.05–0.10 wt% H C 3 maximum; acidity (as acrylic acid), 0.009 wt% (Royal Society of Chemistry, 2018) maximum; hydroquinone (polymerization Relative molecular mass: 184.28 inhibitor), 90–120 ppm; and monomethyl ether of hydroquinone (polymerization inhib- itor), 13–120 ppm (Union Carbide Corp., 1982; 137 IARC MONOGRAPHS – 122 Hoechst Celanese Corp., 1988; ECHA, 2005; food-packaging materials (Tyler, 1993). As a HSDB, 2018). plasticizing co-monomer, 2-ethylhexyl acrylate is used in the production of resins for pres- 1.2 Production and use sure-sensitive adhesives, latex paints, reactive diluents and/or cross-linking agents, textile and 1.2.1 Production process leather finishes, and coatings for paper HSDB,( 2018). 2-Ethylhexyl acrylate can also be used as a Direct, acid-catalysed esterification of acrylic co-monomer in solution polymers for industrial acid with 2-ethylhexanol is the principal method metal finishing Mannsville( Chemical Products for the manufacture of 2-ethylhexyl acrylate. The Corp., 1984; Tyler, 1993). A common use of most common catalysts are sulfuric and para-tol- 2-ethylhexyl acrylate is as a major component in uenesulfonic acid, and sulfonic acid functional acrylic pressure-sensitive adhesives. The typical cation-exchange resins. The monomethyl ether composition of an adhesive for general-purpose of hydroquinone is added as a polymerization tape is 75% 2-ethylhexyl acrylate (Temin, 1990). inhibitor, and the esters are used in this form in 2-Ethylhexyl acrylate is also used in ultra- most industrial applications (ECHA, 2005). violet-curable coatings without solvents, which provide a glossy, abrasion-resistant finish on book 1.2.2 Production volume covers, for example. A typical ultraviolet-cured 2-Ethylhexyl acrylate has been listed as formulation might include 10% 2-ethylhexyl a chemical with a high production volume acrylate diluent monomer and small amounts of (OECD, 2009). The estimated production volume photoinitiator (Mannsville Chemical Products of 2-ethylhexyl acrylate in the USA in 1991 Corp., 1984). was 48 thousand metric tonnes (United States More recent uses of 2-ethylhexyl acrylate International Trade Commission, 1993). By 1999, include in the manufacture of plastics for trans- the total European Union production volume dermal drug delivery systems applied in the was estimated to be 70 thousand metric tonnes fields of estrogen replacement therapy, and in per year (ECHA, 2005). Accounting for imports the delivery of anti-inflammatory drugs in eye and exports, in 1999 a total amount of 90 thou- surgery (Kotiyan & Vavia, 2001; Duarte et al., sand metric tonnes per year was estimated to be 2008). available on the European market, 32 thousand metric tonnes used as internal intermediate, 1.3 Analytical methods and 58 thousand metric tonnes sold to external processing sites (ECHA, 2005). Production Methods for sampling and analysing air have volume in China was 43 thousand metric tonnes been developed for vapours of acrylate mono- in 2008 (Chinese Report, 2008), and doubled mers, including 2-ethylhexyl acrylate (Bosserman to 85 thousand metric tonnes in 2010 (Chinese & Ketcham, 1980; Samimi & Falbo, 1982). The Report, 2010). most common method used is United States Occupational Safety and Health Administration 1.2.3 Use PV2026, in which the acrylate monomer vapour is adsorbed on activated silica gel or charcoal, Acrylic esters are used in the production of desorbed in carbon disulfide, and analysed by polymers and copolymers with a wide range gas chromatography with flame ionization detec- of applications. Polymers containing 2-ethyl- tion (OSHA, 2010). The limit of quantitation is hexyl acrylate are used in different types of 0.01 ppm (0.08 mg/m3). 138 2-Ethylhexyl acrylate No biological markers are reported for expo- 1982). The personal concentrations of 2-ethyl- sure to 2-ethylhexyl acrylate. hexyl acrylate at a process reactor (Reactor A) that had an opening hatch for the addition of 1.4 Occurrence and exposure starting products ranged from not detectable to 2 ppb [20 µg/m3] (mean, 0.4 ppb [3 µg/m3]); 1.4.1 Environmental occurrence nine personal samples taken at a similar reactor contained no detectable concentrations. 2-Ethylhexyl acrylate is readily biodegrad- A further 13 personal samples collected from able in air, water, and soil (ECHA, 2005). The workers tending a completely closed reactor atmospheric half-life is approximately 19 hours ranged from not detectable to 5 ppb [40 µg/m3] (ECHA, 2005). 2-Ethylhexyl acrylate has (mean, 1 ppb [8 µg/m3]). No detectable concen- moderate mobility in soil (HSDB, 2018). In the trations were found in six personal samples taken effluent of an onsite waste-treatment facility, from workers at a closed polymer flake contin- 2-ethylhexyl acrylate was detected at concentra- uous reactor. In 11 personal samples collected tions ranging from 0.6 to 11 ppb (µg/L) (mean, at the unloading docks, concentrations ranged 4 ppb). The treatment facility received water from not detectable to 5 ppb [40 µg/m3] (mean, from a large petrochemical plant where the 2 ppb [20 µg/m3]). Eight area samples taken at influent untreated wastewater contained 2-ethyl- Reactor A had concentrations ranging from not hexyl acrylate at 0.55–5.60 ppm (mg/L) (mean, detectable to 161 ppb [1.21 mg/m3] (mean, 30 ppb 2.0 ppm) (Berglund & Whipple, 1987). [230 µg/m3]); the remaining 41 area samples had no detectable concentrations (Samimi & Falbo, 1.4.2 Exposure in the general population 1982). 2-Ethylhexyl acrylate is not known to occur as Detailed data on the exposure of workers a natural product. Exposure in the general popu- during the manufacture of 2-ethylhexyl acrylate lation may occur through the use of consumer in four plants in the USA were summarized by products (e.g. adhesives, furniture coatings, Tyler (1993). Workers were exposed to mean or paints) or through inadvertent release by concentrations ranging from 30 to 500 ppb 3 industry in the local environment (HSDB, 2018). [0.23–3.77 mg/m ], depending upon manufac- No quantitative information on exposure was turing plant location (Tyler, 1993). available to the Working Group. In a study from spring/summer 2016 among 13 road workers from three companies using 1.4.3 Occupational exposure paint containing 2-ethylhexyl acrylate, exposure to organic solvents and acrylates was measured Occupational exposure occurs in both the over a 5-day working period (de Poot, 2016); manufacture and use of 2-ethylhexyl acrylate. 8-hour time-weighted average (TWA) concentra- As a result of its low vapour pressure, exposure tions of methyl methacrylate, butyl acrylate, and by inhalation is expected to be low. Dermal expo- 2-ethylhexyl acrylate were measured. Although sure may occur during spills or leaks (Björkner the highest concentrations of methyl meth- et al., 1980). acrylate were measured during manual sput- The exposure of workers to styrene and tering, mechanical extruding, and paint spraying, several acrylates (including 2-ethylhexyl acrylate) all three measurements of 2-ethylhexyl acrylate and area concentrations were monitored in a were below the limit of detection (0.4 mg/m3). United States facility where acrylic ester-styrene For short-term task-based measurements, the copolymers were produced (Samimi & Falbo, highest concentrations of methyl methacrylate 139 IARC MONOGRAPHS – 122 resulted from filling spraying reservoirs with 3.1 Mouse paint. One task-based measurement was below the limit of detection for 2-ethylhexyl acrylate 3.1.1 Skin application 3 (7 mg/m ) (de Poot, 2016). A group of 40 male C3H/HeJ mice (age, 7–10 weeks) was exposed to a 75% (by volume) 1.5 Regulations and guidelines solution of 2-ethylhexyl acrylate (purity, 99%) in acetone three times per week for their lifetime A small number of countries have occupa- (DePass, 1982; DePass et al., 1985). The fur was tional exposure limits for 2-ethylhexyl acrylate. clipped from the back of each mouse once per In Germany, Poland, and Switzerland the 8-hour week. Treated mice received “one brushful” of TWA and short-term occupational exposure the dosing solution per application, a dose of limit is 38 mg/m3, and in Austria it is 82 mg/m3.
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