Abstract
In the past decades, the environmental presence and ecological risks of chlorinated paraffins (CPs), an emerging class of organic halogen compounds, have been receiving increasing attention worldwide. Short-chain CPs (SCCPs) and medium-chain CPs (MCCPs) constitute the important CPs of considerable concern. In this review article, the state-of-the-art research status on the environmental transformation of CPs, including thermal decomposition, photolytic and photocatalytic degradation, biological metabolism, and atmospheric transformation, was summarized and integrated in detail. The degradation efficiency and transformation products of CPs in these environmental processes were evaluated, in which dechlorination was considered as the major reaction pathway. Notably, waste incineration of CPs has been demonstrated to generate a variety of persistent chlorinated aromatic hydrocarbons such as polychlorinated biphenyls and polychlorinated naphthalenes, which have more significant environmental impacts. Additionally, photodegradation and photocatalysis are suggested as the feasible techniques for efficient removal of SCCPs from water matrices. Overall, the current transformation studies of CPs could facilitate the comprehensive understanding of their environmental behaviors and fate as well as the development of promising remediation strategies for pollution control.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Data availability
The datasets generated and/or analyzed during the current review article are available in the Web of Science. The copyright permission has been obtained for the reproduced figures.
References
Allpress JD, Gowland PC (1999) Biodegradation of chlorinated paraffins and long-chain chloroalkanes by Rhodococcus sp. S45-1. Int Biodeterior Biodegrad 43:173–179. https://doi.org/10.1016/S0964-8305(99)00050-5
Bergman A, Hagman A, Jacobsson S, Jansson B, Ahlman M (1984) Thermal degradation of polychlorinated alkanes. Chemosphere 13:237–250. https://doi.org/10.1016/0045-6535(84)90130-9
Chen X, Zhao Q, Li X, Wang D (2016) Enhanced photocatalytic activity of degrading short chain chlorinated paraffins over reduced graphene oxide/CoFe2O4/Ag nanocomposite. J Colloid Interface Sci 479:89–97. https://doi.org/10.1016/j.jcis.2016.06.053
Darnerud PO, Biessmann A, Brandt I (1982) Metabolic fate of chlorinated paraffins: degree of chlorination of [1-14C]-chlorododecanes in relation to degradation and excretion in mice. Arch Toxicol 50:217–226. https://doi.org/10.1007/BF00310853
El-Morsi TM, Budakowski WR, Abd-El-Aziz AS, Friesen KJ (2000) Photocatalytic degradation of 1,10-dichlorodecane in aqueous suspensions of TiO2: a reaction of adsorbed chlorinated alkane with surface hydroxyl radicals. Environ Sci Technol 34:1018–1022. https://doi.org/10.1021/es9907360
Feng M, Clayton Baum J, Nesnas N et al (2019) Oxidation of sulfonamide antibiotics of six-membered heterocyclic moiety by ferrate(VI): kinetics and mechanistic insight into SO2 extrusion. Environ Sci Technol 53:2695–2704. https://doi.org/10.1021/acs.est.8b06535
Feng M, Jinadatha C, J. McDonald T, K. Sharma V (2018) Accelerated oxidation of organic contaminants by ferrate(VI): the overlooked role of reducing additives. Environ Sci Technol 52:11319–11327. https://doi.org/10.1021/acs.est.8b03770
Feng M, Qu R, Habteselassie M, Wu J, Yang S, Sun P, Huang Q, Wang Z (2015a) Hepatic transcriptome responses in mice (Mus musculus) exposed to the nafion membrane and its combustion products. PLoS One 10:e0128591. https://doi.org/10.1371/journal.pone.0128591
Feng M, Qu R, Wei Z, Wang L, Sun P, Wang Z (2015b) Characterization of the thermolysis products of Nafion membrane: a potential source of perfluorinated compounds in the environment. Sci Rep 5:9859. https://doi.org/10.1038/srep09859
Feng M, Wang X, Wang C et al (2015c) Antioxidant status and Na+, K+-ATPase activity in freshwater fish Carassius auratus exposed to different combustion products of Nafion 117 membrane: an integrated biomarker approach. Environ Sci Pollut res 22. https://doi.org/10.1007/s11356-014-3826-3
Glüge J, Schinkel L, Hungerbühler K, Cariou R, Bogdal C (2018) Environmental risks of medium-chain chlorinated paraffins (MCCPs): a review. Environ Sci Technol 52:6743–6760. https://doi.org/10.1021/acs.est.7b06459
Glüge J, Wang Z, Bogdal C, Scheringer M, Hungerbühler K (2016) Global production, use, and emission volumes of short-chain chlorinated paraffins – a minimum scenario. Sci Total Environ 573:1132–1146. https://doi.org/10.1016/j.scitotenv.2016.08.105
Heeb NV, Schalles S, Lehner S, Schinkel L, Schilling I, Lienemann P, Bogdal C, Kohler HPE (2019) Biotransformation of short-chain chlorinated paraffins (SCCPs) with LinA2: a HCH and HBCD converting bacterial dehydrohalogenase. Chemosphere 226:744–754. https://doi.org/10.1016/j.chemosphere.2019.03.169
Koh IO, Thiemann W (2001) Study of photochemical oxidation of standard chlorinated paraffins and identification of degradation products. J Photochem Photobiol A Chem 139:205–215. https://doi.org/10.1016/S1010-6030(00)00427-5
Lee J, von Gunten U, Kim JH (2020) Persulfate-based advanced oxidation: critical assessment of opportunities and roadblocks. Environ Sci Technol 54:3064–3081. https://doi.org/10.1021/acs.est.9b07082
Li C, Xie HB, Chen J, Yang X, Zhang Y, Qiao X (2014) Predicting gaseous reaction rates of short chain chlorinated paraffins with •OH: overcoming the difficulty in experimental determination. Environ Sci Technol 48:13808–13816. https://doi.org/10.1021/es504339r
Li T, Wan Y, Gao S, Wang B, Hu J (2017a) High-throughput determination and characterization of short-, medium-, and long-chain chlorinated paraffins in human blood. Environ Sci Technol 51:3346–3354. https://doi.org/10.1021/acs.est.6b05149
Li Y, Chen W, Kong W, Liu J, Schnoor JL, Jiang G (2020) Transformation of 1,1,1,3,8,10,10,10-octachlorodecane in air phase increased by phytogenic volatile organic compounds of pumpkin seedlings. Sci Total Environ 704:135455. https://doi.org/10.1016/j.scitotenv.2019.135455
Li Y, Hou X, Chen W, Liu J, Zhou Q, Schnoor JL, Jiang G (2019) Carbon chain decomposition of short chain chlorinated paraffins mediated by pumpkin and soybean seedlings. Environ Sci Technol 53:6765–6772. https://doi.org/10.1021/acs.est.9b01215
Li Y, Hou X, Yu M, Zhou Q, Liu J, Schnoor JL, Jiang G (2017b) Dechlorination and chlorine rearrangement of 1,2,5,5,6,9,10-heptachlorodecane mediated by the whole pumpkin seedlings. Environ Pollut 224:524–531. https://doi.org/10.1016/j.envpol.2017.02.035
Liu R, Zhang C, Kang L, Sun X, Zhao Y (2015) The •OH-initiated chemical transformation of 1,2,4,6,8,10,11-heptachloroundecane in the atmosphere. RSC Adv 5:37988–37994. https://doi.org/10.1039/c5ra00612k
Lu M (2013) Degradation of short chain polychlorinated paraffins by a new isolate: tests in pure culture and sewage sludge. J Chem Technol Biotechnol 88:1273–1279. https://doi.org/10.1002/jctb.3971
Omori T, Kimura T, Kodama T (1987) Bacterial cometabolic degradation of chlorinated paraffins. Appl Microbiol Biotechnol 25:553–557. https://doi.org/10.1007/BF00252016
Peng Y, Fang W, Yan L, Wang Z, Wang P, Yu J, Zhang X (2020) Early life stage bioactivity assessment of short-chain chlorinated paraffins (SCCPs) at environmentally relevant concentrations by concentration-dependent transcriptomic analysis of zebrafish embryos. Environ Sci Technol 54:996–1004. https://doi.org/10.1021/acs.est.9b04879
Schinkel L, Bogdal C, Canonica E, Cariou R, Bleiner D, McNeill K, Heeb NV (2018a) Analysis of medium-chain and long-chain chlorinated paraffins: the urgent need for more specific analytical standards. Environ Sci Technol Lett 5:708–717. https://doi.org/10.1021/acs.estlett.8b00537
Schinkel L, Lehner S, Heeb NV, Lienemann P, McNeill K, Bogdal C (2017) Deconvolution of mass spectral interferences of chlorinated alkanes and their thermal degradation products: chlorinated alkenes. Anal Chem 89:5923–5931. https://doi.org/10.1021/acs.analchem.7b00331
Schinkel L, Lehner S, Knobloch M, Lienemann P, Bogdal C, McNeill K, Heeb NV (2018b) Transformation of chlorinated paraffins to olefins during metal work and thermal exposure – Deconvolution of mass spectra and kinetics. Chemosphere 194:803–811. https://doi.org/10.1016/j.chemosphere.2017.11.168
Shang H, Fan X, Kubwabo C, Rasmussen PE (2019) Short-chain and medium-chain chlorinated paraffins in Canadian house dust and NIST SRM 2585. Environ Sci Pollut Res 26:7453–7462. https://doi.org/10.1007/s11356-018-04073-2
UNEP (2017). Report of the conference of the parties to the Stockholm convention on persistent organic pollutants on the work of its eighth meeting. UNEP/POPS/COP.8/32
van Mourik LM, Gaus C, Leonards PEG, de Boer J (2016) Chlorinated paraffins in the environment: a review on their production, fate, levels and trends between 2010 and 2015. Chemosphere 155:415–428. https://doi.org/10.1016/j.chemosphere.2016.04.037
Von Gunten U (2018) Oxidation processes in water treatment: are we on track? Environ Sci Technol 52:5062–5075. https://doi.org/10.1021/acs.est.8b00586
Wang XT, Zhang Y, Miao Y, Ma LL, Li YC, Chang YY, Wu MH (2013) Short-chain chlorinated paraffins (SCCPs) in surface soil from a background area in China: occurrence, distribution, and congener profiles. Environ Sci Pollut Res 20:4742–4749. https://doi.org/10.1007/s11356-012-1446-3
Wang Y, Gao W, Jiang G (2017) Strengthening the study on the behavior and transformation of medium-chain chlorinated paraffins in the environment. Environ Sci Technol 51:10282–10283. https://doi.org/10.1021/acs.est.7b03251
Wei GL, Liang XL, Li DQ, Zhuo MN, Zhang SY, Huang QX, Liao YS, Xie ZY, Guo TL, Yuan ZJ (2016) Occurrence, fate and ecological risk of chlorinated paraffins in Asia: a review. Environ Int 92–93:373–387. https://doi.org/10.1016/j.envint.2016.04.002
Xin S, Gao W, Cao D, Lv K, Liu Y, Zhao C, Wang Y, Jiang G (2019) The thermal transformation mechanism of chlorinated paraffins: an experimental and density functional theory study. J Environ Sci 75:378–387. https://doi.org/10.1016/j.jes.2018.05.022
Xin S, Gao W, Wang Y, Jiang G (2018) Identification of the released and transformed products during the thermal decomposition of a highly chlorinated paraffin. Environ Sci Technol 52:10153–10162. https://doi.org/10.1021/acs.est.8b01729
Xin S, Gao W, Wang Y, Jiang G (2017) Thermochemical emission and transformation of chlorinated paraffins in inert and oxidizing atmospheres. Chemosphere 185:899–906. https://doi.org/10.1016/j.chemosphere.2017.07.019
Xiong W, Li X, Zhao Q, Shi Y, Hao C (2018) Insight into the photocatalytic mineralization of short chain chlorinated paraffins boosted by polydopamine and Ag nanoparticles. J Hazard Mater 359:186–193. https://doi.org/10.1016/j.jhazmat.2018.07.066
Yuan B, Muir D, MacLeod M (2019a) Methods for trace analysis of short-, medium-, and long-chain chlorinated paraffins: critical review and recommendations. Anal Chim Acta 1074:16–32. https://doi.org/10.1016/j.aca.2019.02.051
Yuan B, Vorkamp K, Maria Roos A et al (2019b) Accumulation of short-, medium-, and long-chain chlorinated paraffins in marine and terrestrial animals from Scandinavia. Environ Sci Technol 53:3526–3537. https://doi.org/10.1021/acs.est.8b06518
Zellmer S, Heiserich L, Kappenstein O, Merkel S, Schulte A, Luch A (2020) MCCP: are medium-chain chlorinated paraffins of concern for humans? Arch Toxicol 94:955–957. https://doi.org/10.1007/s00204-020-02681-x
Zhang W, Gao Y, Qin Y, Wang M, Wu J, Li G, An T (2019) Photochemical degradation kinetics and mechanism of short-chain chlorinated paraffins in aqueous solution: a case of 1-chlorodecane. Environ Pollut 247:362–370. https://doi.org/10.1016/j.envpol.2019.01.065
Zhang ZY, Lu M, Zhang ZZ, Xiao M, Zhang M (2012) Dechlorination of short chain chlorinated paraffins by nanoscale zero-valent iron. J Hazard Mater 243:105–111. https://doi.org/10.1016/j.jhazmat.2012.10.004
Zhou Y, Yuan B, Nyberg E, Yin G, Bignert A, Glynn A, Odland JØ, Qiu Y, Sun Y, Wu Y, Xiao Q, Yin D, Zhu Z, Zhao J, Bergman Å (2020) Chlorinated Paraffins in human Milk from urban sites in China, Sweden, and Norway. Environ Sci Technol 54:4356–4366. https://doi.org/10.1021/acs.est.9b06089
Acknowledgements
This work was supported by the Sponge City Special Research of Wanzhou District (No. SW-2017-064) and the National Natural Science Foundation of China (No. 51709024).
Author information
Authors and Affiliations
Contributions
In this review article, SY is responsible for the writing, reviewing, and editing. MW is responsible for the supervision, conceptualization, methodology, reviewing, and editing. BL and JW are responsible for the reviewing and editing. All authors have read and approved the final manuscript.
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Ethical approval
Not applicable.
Consent to participate
All authors consent to participate in this review article.
Consent to publish
All authors consent to publish this review paper in Environmental Science and Pollution Research.
Additional information
Responsible editor: Roland Peter Kallenborn
Publisher’s note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Yuan, S., Wang, M., Lv, B. et al. Transformation pathways of chlorinated paraffins relevant for remediation: a mini-review. Environ Sci Pollut Res 28, 9020–9028 (2021). https://doi.org/10.1007/s11356-021-12469-w
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11356-021-12469-w