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Furfuryl Alcohol SOME CHEMICALS THAT CAUSE TUMOURS OF THE URINARY TRACT IN RODENTS VOLUME 119 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, 6–13 June 2017 LYON, FRANCE - 2019 IARC MONOGRAPHS ON THE EVALUATION OF CARCINOGENIC RISKS TO HUMANS FURFURYL ALCOHOL 1. Exposure Data 1.1.3 Chemical and physical properties 1.1 Identification of the agent Description: Furfuryl alcohol is a colour- less or pale yellow liquid with characteristic 1.1.1 Nomenclature “burning” odour and bitter taste; it turns red or brown on exposure to light and air Chem. Abstr. Serv. Reg. No.: 98-00-0 Boiling point: 170 °C Chem. Abstr. Serv. name: Furanmethanol Melting point: –15 °C EC name: Furfuryl alcohol Density: 1.1296 g/cm3 at 20 °C IUPAC systematic name: 2-Furylmethanol Solubility: Very soluble in ethanol and ethyl Synonyms: 2-Furanmethanol, furfurol, ether, soluble in ketone and chloroform; it 2-(hydroxymethyl)furan, 2-furylcarbinol; 2- dissolves cellulose nitrate, some dyes and furancarbinol; α-furylcarbinol; furfural co hol synthetic resins (Ellis, 1972); it is miscible From NTP (1999); European Commission with water, forming an azeotrope at atmos- (2011) pheric pressure (water, 80 wt%; boiling point, 98.5 °C). 1.1.2 Structural and molecular formulae, and Volatility: Vapour pressure, 53 kPa at 20 °C relative molecular mass Flash point: 65 °C (tag closed cup) Explosive limits: 1.8–16.3 vol% in air OH Stability: Pure furfuryl alcohol decomposes O upon standing for extended periods; it should be stored in a dark bottle in a refrigerator at 0 °C (NIOSH, 1994) Relative vapour density: 3.4 (air = 1) Molecular formula: C5H6O2 Octanol/water partition coefficient (P): log Relative molecular mass: 98.10 (NTP, 1999) Kow, 0.28 Odour threshold: About 28 mg/m3 in humans; 50% response at 8 ppm Conversion factor: 1 ppm = 4.01 mg/m3 at normal temperature (25 °C) and pressure (103.5 kPa) 83 IARC MONOGRAPHS – 119 Impurities: No data on impurities were avail- has been explored as an alternative; however, it able; overall purity is usually > 98% (NTP, is still relatively understudied and not widely 1999; Hoydonckx, 2007). applied (Mandalika et al., 2014). From NTP (1999); Lide (2005); Hoydonckx (2007); European Commission (2011). 1.2.2 Production volume Global production of furfuryl alcohol was 1.2 Production and use estimated at about 300 000 tonnes in 2015 (Grand View Research, 2015). Furfuryl alcohol is listed 1.2.1 Production process by the Organisation for Economic Co-operation and Development (OECD) (OECD, 2018) and the Furfuryl alcohol is produced industrially by United States Environmental Protection Agency the hydrogenation of furfural. Vapour-phase (EPA) as a chemical with a high production reaction or liquid-phase reaction are both used, volume, with more than 1 million pounds [more although the vapour-phase reaction at atmos- than 453 tonnes] produced annually (Franko pheric pressure is currently the most widely et al., 2012). China is the main global manufac- employed, except in China (Chen et al., 2002; turer and user of furfuryl alcohol, with 80–85% of Hoydonckx, 2007; ITC, 2012). global capacity and production, and about 60% of Furfural contains two kinds of reactive group global consumption in 2015 (IHS Markit, 2016). – a carbonyl group and carbon–carbon double Between 10 000 and 100 000 tonnes are manu- bonds; hydrogenation of the former gives furfuryl factured and/or imported into the European alcohol, and hydrogenation of the latter results in Economic Area each year (ECHA, 2018a). A tetrahydrofurfural. The catalytic hydrogenation single industrial plant in Belgium produced of the furfural carbonyl group requires the pres- around 40 000 tonnes per year (IFC, 2016). The ence of heterogeneous or homogeneous catalysts. database ChemSources-Online lists 31 manufac- The heterogeneous copper chromite catalyst has turing companies worldwide (Chemical Sources been used at an industrial scale for more than International, 2017). six decades (Villaverde et al., 2013); however, the toxicity and carcinogenic potential asso- 1.2.3 Use ciated with chromite (IARC, 1990; Chen et al., 2002), and environmental problems associated It has been estimated that the production with deactivated copper chromite catalyst have of furan resins for foundry sand binders in the prompted the development of other catalysts metal casting industry accounted for about based on copper (Vargas-Hernández et al., 2014; 85–90% of furfuryl alcohol used worldwide (IHS Jiménez-Gómez et al., 2016), nickel (Baijun et al., Markit, 2016). Furfuryl alcohol is also used as a 1998; Li et al., 2003; Kotbagi et al., 2016), ruthe- wetting agent and as a solvent for dyes and as nium (Tukacs et al., 2017), platinum, and palla- corrosion inhibitor in fibre-reinforced plastics, dium (O’Driscoll et al., 2017), among others. in cements and mortars, and in wood protec- Production of furfuryl alcohol from xylose tion. Applications also include use in flavours over a dual heterogeneous catalyst system has and fragrances. Moreover, furfuryl alcohol is also been described (Perez & Fraga, 2014; Cui used as a laboratory reagent and as a chemical et al., 2016). building block for drug synthesis (Sriram & The potential of microbial conversion of Yogeeswari, 2010; European Commission, 2011; furfural for the production of furfuryl alcohol IHS Markit, 2016). In addition, the product of 84 Furfuryl alcohol Table 1.1 Representative methods for the analysis of furfuryl alcohol Sample matrix Assay procedure Limit of detection Reference Air of workplace TDS-GC-FID 2.25 mg/m3 (LOQ) Tschickardt (2012) TDS-GC-FID NR ISO (2000, 2001); NIOSH (1994) Dust particles GC-UV ≤ 0.4 μg/g Nilsson et al. (2005) Foundry resins GC-FID 173 μg/L Oliva-Teles et al. (2005) LC-UV 5.2 mg/L Fruit juices LC-UV 3 mg/L Yuan & Chen (1999) Environmental water GC-MS 0.02 μg/L Kawata et al. (2001) Roasted coffee SPME-GC-MS NR Yang & Peppard (1994) Wine SPME-GC-MS 7 µg/L Carrillo et al. (2006) Coffee HS-SPME-GC-MS 0.59 mg/L Petisca et al. (2013a) Coffee NMR 3.2 mg/L Okaru & Lachenmeier (2017) Deep-fried products HS-SPME-GC-MS 1.5 mg/kg Pérez-Palacios et al. (2012) GC-FID, gas chromatography-flame ionization detector; GC-MS, gas chromatography-mass spectrometry; GC-UV, gas chromatography- ultraviolet spectrometry; HS, headspace; LC-UV, liquid chromatography-ultraviolet spectrometry; LOQ, limit of quantification; NMR, nuclear magnetic resonance; NR, not reported; SPME, solid-phase microextraction; TDS, thermal desorption system the hydrogenation of furfuryl alcohol, tetrahy- volatile compounds like furfuryl alcohol (Carrillo drofurfuryl alcohol, is used in plant protection et al., 2006; Pérez-Palacios et al., 2012; 2013; 2014; products (ECHA, 2018b). Petisca et al., 2013a, 2013b, 2014). The first reports on analysis indicated headspace incubation and 1.3 Analytical methods extraction temperatures of 80 °C for at least 30 minutes (EFSA, 2004), but temperature was later Representative methods for the analysis of reduced to 60 °C (FDA, 2005), and even lower furfuryl alcohol in environmental and food (Pérez-Palacios et al., 2012), to avoid formation matrices are summarized in Table 1.1. In general, of additional amounts of furanic compounds gas chromatography with mass spectrometry during analysis. (GC-MS) is preferred due to its higher sensitivity. Thermal desorption combined with GC-MS 1.4 Occurrence and exposure or with gas chromatography-ultraviolet spec- trometry (GC-UV) has been used to analyse 1.4.1 Occurrence furfuryl alcohol adsorbed to indoor dust parti- cles (Nilsson et al., 2005). Due to its high production volume and large Extraction of furfuryl alcohol from food number of industrial and consumer uses, furfu- matrices (before chromatographic analysis) ryl alcohol is ubiquitous in the environment. can be performed by different methods, namely Should furfuryl alcohol be released to the solvent extraction, solid-phase extraction, simul- soil, it is expected to have very high mobility taneous distillation extraction, and solid-phase based upon an estimated soil adsorption coeffi- cient, K , of 34. If released into water, furfuryl microextraction (Yang & Peppard, 1994; Cocito oc et al., 1995; Spillman et al., 1998; Gómez Plaza alcohol is not expected to adsorb to suspended et al., 1999; Jerković et al., 2007). solids and sediment, based upon an observed Headspace-solid phase microextraction degradation of 75–79% in 2 weeks. If released to methods are advantageous for the analysis of air, furfuryl alcohol will exist solely as a vapour 85 IARC MONOGRAPHS – 119 in the atmosphere (on the basis of its vapour et al., 2017; Pico et al., 2017) also contain furfuryl pressure), and will be degraded by reaction with alcohol. photochemically produced hydroxyl radicals. Among the many heterocyclic compounds The half-life for this reaction is estimated to be reported to be present in roasted coffee, furans 3.7 hours. Furfuryl alcohol may also be suscep- were found to be abundant (Flament & Bessiere- tible to direct photolysis by sunlight, on the basis Thomas, 2002; Petisca et al., 2013a). The forma- of its absorption of ultraviolet light at wavelengths tion of furanic compounds in roasted coffee has > 290 nm (National Library of Medicine, 2018). been attributed to Maillard reactions; however, Furfuryl alcohol has been identified as a side degradation of less volatile coffee constituents, product in Maillard reactions (Schirle-Keller & such as quinic, caffeic, and chlorogenic acids can Reineccius, 1992; Chen & Ho, 1999). Its forma- also result in the formation of furfuryl alcohol tion from glucose in aqueous systems has been (Moon & Shibamoto, 2010). described. The mechanism involves the oxidation During wine ageing, furfuryl alcohol is of glucose to gluconic acid, which is decarboxy- formed by microbiological reduction of the lated to a pentitol and followed by dehydration furfuryl aldehydes (Spillman et al., 1998).
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