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N,N-Dimethylformamide

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N,N-Dimethylformamide N,N-DIMETHYLFORMAMIDE N,N-Dimethylformamide was considered by the IARC Monographs Working Group in 1989 and 1998 (IARC, 1989, 1999). New data have become available and have been taken into consideration in the present evaluation. 1. Exposure Data 1.1.3 Physical and chemical properties of the pure substance 1.1 Identification of the agent Description: Colourless to slightly yellow 1.1.1 Nomenclature liquid with a faint amine-like odour (HSDB, 2015) Chem. Abstr. Serv. Reg. No.: 68-12-2 Degradation: Dimethylamine can be released Chem. Abstr. Serv. Name: N,N-Dimethyl- from N,N-dimethylformamide and, in the formamide presence of nitrogen oxides, carcinogenic IUPAC Systematic Name: N,N-Dimethyl- nitrosamines can be formed. Other potential formamide degradation products are ammonia, carbon monoxide, carbon dioxide, amines and Synonyms: N,N-Dimethylmethane amide, formaldehyde. formic acid dimethyl amide, N-formyl- 3 dimethylamine Density (at 20 °C): 0.95 g/cm (IFA, 2015) Acronym: DMF Octanol/water partition coefficient: log Kow, −1.01 (HSDB, 2015) Melting point: −61 °C (IFA, 2015) 1.1.2 Structure and molecular formula, and relative molecular mass Boiling point: 153 °C (IFA, 2015) Vapour pressure (at 20 °C): 0.377 kPa (2.83 mm Hg) (IFA, 2015) H3C O N Vapour density: 2.51 (air = 1) (HSDB, 2015) Solubility: Entirely soluble in water at 20 °C H C H 3 (IFA, 2015) Molecular formula: C3H7NO Flammable limits: Lower explosion limit: Relative molecular mass: 73.09 2.2 vol. %; upper explosion limit: 16 vol. % (IFA, 2015) Flash point: 58 °C (IFA, 2015) 119 IARC MONOGRAPHS – 115 Ignition temperature: 440 °C (IFA, 2015) USA remained constant between 1986 and 2002, Conversion factor (101 kPa, 20 °C): and was reported to be between 50 and 100 million 1 ppm = 3.04 mg/m3 (IFA, 2015). pounds [approximately 20 000 and 45 000 tonnes] (HSDB, 2015). The annual production and import volume of nine USA companies was about 50 1.2 Production and use million pounds [~25 000 tonnes] (HSDB, 2015) and the total annual production volume in the 1.2.1 Production European Union ranged from 50 000 to 100 000 N,N-Dimethylformamide is predominantly tonnes in 2000 (SCOEL, 2006). No production produced in a single-step reaction between volumes could be traced for Asia, but more than dimethylamine and carbon monoxide under 300 suppliers of N,N-dimethylformamide could pressure at high temperatures and in the pres- be identified globally, including > 200 in Asia, ence of basic catalysts such as sodium meth- > 60 in the USA, and > 30 in the European Union oxide. The crude product contains methanol and (ChemBook, 2015). N,N-dimethylformamide with increased purity (up to 99.9%) is obtained by multiple distillations 1.2.2 Use (HSDB, 2015). Alternatively, it can be produced N,N-Dimethylformamide is used predom- by a two-step process in which methyl formate is inantly as an aprotic solvent in the manufac- prepared separately and, in a second step, reacts ture of polyacrylonitrile fibres, and trends in with dimethylamine under similar conditions its production parallel those of the polyacrylic as those described for the single-step reaction. fibre industry (HSDB, 2015). It is also used in the No catalysts are involved in the process (HSDB, manufacture of high quality polyurethane and 2015). polyamide coatings (e.g. for leather or artificial N,N-Dimethylformamide is listed as a high leather fabrics), which are otherwise difficult to production volume chemical by the Organisation solubilize, and where a solvent with a slow rate of for Economic Co-operation and Development evaporation is needed. N,N-Dimethylformamide (OECD), indicating that this chemical is is commonly used as a solvent in the electronics produced or imported at levels greater than 1000 industry, in pesticides, in industrial paint-strip- tonnes per year in at least one member country ping applications, and as a reaction and crystal- or region (OECD, 2004, 2009). The OECD 2007 lizing solvent in the pharmaceutical industry. list of high production volume chemicals was It has limited use as a selective solvent for the compiled on the basis of submissions from eight separation of aliphatic hydrocarbons such as the member countries (including Australia, Canada, extraction of acetylene or butadiene from hydro- Japan, and the USA) in addition to the list carbon streams (HSDB, 2015). provided by the European Union (OECD, 2009). N,N-Dimethylformamide is also listed as a high production volume chemical in the USA 1.3 Measurement and analysis by the Environmental Protection Agency (EPA) Multiple methods exist for the analysis of indicating that > 1 million pounds [~450 tonnes] N,N-dimethylformamide and its metabolites were produced in or imported into the USA in in air, water, urine, and blood. The methods 1990 and/or 1994 (HSDB, 2015). are largely based on gas chromatography (GC) The annual production volume ofN ,N- and high-performance liquid chromatography dimethylformamide (excluding imports) in the (HPLC) with various detection systems such as 120 N,N-Dimethylformamide flame ionization, nitrogen-sensitive, or mass-sen- mercapturic acids of organic compounds rather sitive detection. than measuring AMCC alone (Schettgen et al., N,N-Dimethylformamide is most commonly 2008; Schettgen, 2010; Alwis et al., 2012). [The measured in air by adsorbing on a silica gel and Working Group noted that AMCC can also be analysis by GC/flame ionization detection. The detected in the urine of the general population level of detection is approximately 0.05 mg per as a result of its endogenous production in the sample in a 15-L air sample or higher at a flow body (Käfferlein & Angerer, 1999).] rate of 0.01–1 L/min (NIOSH, 1994). Several diffusive sampling devices have 1.4 Occurrence and exposure been described for exposure assessment of N,N-dimethylformamide in the air of the work- 1.4.1 Natural occurrence place (Tanaka et al., 2002; Baglioni et al., 2007). Because of the potential for dermal uptake, N,N-Dimethylformamide is not known to exposure to N,N-dimethylformamide should occur as a natural product. be measured by biomonitoring. Major metabo- lites in urine are N-hydroxymethyl-N-methyl- 1.4.2 Environmental occurrence formamide (HMMF), N-methylformamide and Industrial releases of N,N-dimethylform- N-acetyl-S-(N-methylcarbamoyl)cysteine amide into the air appear to be considerably (AMCC) (Gescher, 1993). HMMF degrades at larger than those into other environmental injection temperatures > 250 °C, which allows media. N,N-Dimethylformamide is expected the determination of total N-methylformamide to exist almost entirely in the vapour phase in in biological samples (Kawai et al., 1992). ambient air. When emitted into air, most of the An HPLC method also has been described N,N-dimethylformamide released remains in that has a pre-heat phase to convert HMMF to that compartment where it is degraded by chem- N-methylformamide. The reported detection ical reactions with hydroxyl radicals; its half-life limit was 0.5 mg/L (Tranfo et al., 1999). As an in the air is estimated to be in the range of few alternative, HMMF can be converted chemi- days. Some atmospheric N,N-dimethylform- cally to N-methylformamide in the presence of amide can reach the aquatic and terrestrial envi- potassium carbonate during sample preparation ronment, presumably during periods of rain. (Mráz & Turecek, 1987). The limits of detec- Releases into the water or soil are expected to be tion are usually approximately 1 mg/L for total followed by relatively rapid biodegradation (half- N-methylformamide and sufficient for exposure life, 18–36 hours) (IPCS, 2001; HSDB, 2015). assessment in N,N-dimethylformamide-exposed Measurements of N,N-dimethylformamide workers (Mráz et al., 1987). in air and water are presented in Table 1.1. Recently, a method for simultaneously analysing total N-methylformamide and AMCC (a) Air by capillary GC and nitrogen-selective detector In Lowell, MA, USA, N,N-dimethylform- with an injector temperature > 250 °C has been amide was detected in the air over an aban- described (Käfferlein & Angerer, 2005). Under doned chemical waste reclamation plant (mean, these conditions, the limits of detection were 7 μg/m3), a neighbouring industry (> 150 μg/m3), 1 mg/L of urine for total N-methylformamide and a residential area (24 μg/m3) (Amster et al., and 0.5 mg/L of urine for AMCC. 1983; cited in IPCS, 2001). In ambient air samples The measurement of AMCC in urine can collected in the north-eastern USA in 1983, levels also form part of a multi-analysis of various 121 122 IARC MONOGRAPHSIARC 115 – Table 1.1 Environmental exposure to N,N-dimethylformamide Country Duration Sites/situation DMF exposure Reference DMF in air NMF in urine DMF in surface water (μg/L) (μg/m3) (mg/g creatinine) No. Mean SD Range No. Mean SD No. Mean SD Range China 1-year “Unpolluted” area in 366a 98.3 109.7 4.4–678.3 Wang et al.(2014) follow-up Longwan Cross- Near synthetic A 25 297.5 95 25 7.7 6.2 sectional leather factories in B 39 430 122.5 39 6.7 2.7 Longwan C 22 180 0 22 1.5 1.7 D 23 565 516.2 23 23.4 24.9 E 24 270 84.9 24 1.8 0.8 Japan Cross- All over Japan 105b 0.092c 0.016–0.49 47d 0.27c ND–0.53 Ministry of the sectional Environment Japan (2012) USA North-eastern ND–14 Kelly et al. (1994) USA Massachusetts/ 7– > 150 Amster et al. (1983) polluted area cited in IPCS (2001) a Monitoring daily throughout 2008 b Three samples were measured from 35 sites in Japan.
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