By-Side Impurities in Chloronaphthalene Mixtures of the Halowax Series: All 209 Chlorobiphenyls

Abstract

202 congeners of chlorobiphenyl (CB) with 109 single-resolved compounds and 93 co-eluting, which represented from mono- to deca-CB were quantified as by-side impurities in all seven and of various type the technical chloronaphthalene (CN) formulations of the Halowax series. IUPAC No. 104, 145, 159, 169, 184, 186, and 188 were undetected (<0.05-<0.7 ng/g). The total CBs content of the Halowax formulations ranged between 220 and 640,000 ng/g, and lower chlorinated Halowaxes 1031 (27% Cl) and 1000 (35% Cl) were two to three orders of magnitude more contaminated with CBs than higher chlorinated Halowax 1001, 1099, 1013, 1014, and 1051 (49-70% Cl). The profile of CB homologue groups of the Halowaxes changed and followed somehow a degree of chlorination of the parent CN mixture. For Halowax 1031 and 1000, a decreasing trend in proportion from mono- to deca-CB was evident, while for Halowax 1001, 1099, 1013, 1014, and 1051 the relative proportions between the CB homologue groups varied somehow. Evidently content of lower chlorinated mono- and di-CBs highly decreased and steadily increased tri- to octa-CBs and they become dominating homologues in Halowax formulations in parallel with an increase of the content of higher molecular weight CN constituents, respectively. Among planar non- and mono-ortho CBs, total concentrations in Halowax formulations were detected in the range of 2.0-2600 ng/g, and only 3,3',4,4',5,5'-HxCB (no. 169) was undetected (<0.05ng/g). Detection of by-side CBs in technical Halowaxes demonstrate clearly that those formulations apart from a massive introduction of dioxin-like CNs become in the past also an early source of environmental pollution with CBs, which proceeded for around 20-30 years use of original CB formulations.

Risks for animal and human health related to the presence of polychlorinated naphthalenes (PCNs) in feed and food

“…Each mixtures series (e.g. Halowax series) differed in the chlorination degree of the naphthalene molecule resulting in different congeners present in the mixture (Falandysz et al, 2000(Falandysz et al, , 2008Falandysz et al, 2006aFalandysz et al, , 2006bNoma et al, 2004). Production was voluntary suspended by the companies in the 1980s in most countries (Cui et al, 2018;Fernandes et al, 2017).…”

Highly Toxic Chlorobiphenyl and By-Side Impurities Content and Composition of Technical Chlorofen Formulation

“…[1,2] Chlorofen is highly chlorinated type of technical chlorobiphenyl mixture and has an appearance of a light-to-dark-brown sticky and viscous resin. [11][12][13][14][15][16][17][18][19][20][21] Hence, a detailed knowledge on composition and content of toxic and persistent constituents of these mixtures is substantial to understand their effects and environmental fate but also for inventory, sources identification and monitoring purposes. [4][5][6][7][8][9][10] An original chlorobiphenyl and chloronaphthalene formulations become a diffuse type source of the environmental pollution both with a parent compounds but also a by-side contaminants including at least chemicals such as CBs, CNs, CDFs, CDDs, chlorobenzenes (CBzs), and chlorophenols (CPhs).…”

By-Side Chlorobenzenes and Chlorophenols in Technical Chlorobiphenyl Formulations of Aroclor 1268, Chlorofen, Clophen T 64, Kanechlor 600, and Kanechlor 1000

“…[1] It has been clarified recently that technical chloronaphthalene Halowax formulations, which were precursors to chlorobiphenyl mixtures, are contaminated with numerous by-side chemicals including chlorobenzenes (CBzs), chlorophenols (CPhs), chlorodibenzofurans (CDFs), chlorodibenzo-p-dioxins (CDDs), and CBs. [2][3][4][5][6] Apart from resistance to degradation and highly toxic CDD/Fs or planar CBs also chlorobenzenes and chlorophenols are environmentally relevant pollutants. [2,3,[7][8][9][10][11][12] In this study a full qualitative and quantitative characteristic were elucidated of 12 chlorobenzene and 19 chlorophenol congeners theoretically possible that contaminate relatively highly chlorinated technical CB formulations of Aroclor 1268 (USA), Chlorofen (Poland), and Kanechlor 600 (Japan), as well as Clophen T 64 (Germany) and Kanechlor 1000 (Japan).…”