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NAERINGSPH-Nærings-phd

Synthesis of stable isotope labelled poly-/per-halogenated alkanes as reference standards for environmental analysis

Alternative title: Syntese av stabile isotop-merkede poly- / per-halogenerte alkaner som referansestandarder for miljøanalyse

Awarded: NOK 2.3 mill.

Project Manager:

Project Number:

298628

Project Period:

2019 - 2023

Funding received from:

Organisation:

Synthesis of CP congeners has been improved and the process has been established for making pure individual CP compounds. The synthesis methods developed have been applied for the synthesis of 13C-labelled CPs. A patent application for the process was submitted in march 2022. A synthesis route for making 13C-labelled PFAS is still under developing, more investigation need to be done in order to develop a safe and cost efficient way for the preparation. The candidate has been working on 3 articles beside the patent application, one is about the NMR technique for chlorine content analysis which was published at “Chemosphere”; the second article is on the synthesis of pure CP congeners; the third one purification and X-ray structure of CP stereoisomers: I. S. Valderhaug, H. Liu, A. Gorovoy, J. E. Johansen, O. R. Gautun Synthesis of constitutionally defined chlorinated paraffins as reference standards. Submitted to Results in Chemistry. II. (patent) A. Gorovoy, H. Liu, J. Tuma, S. Valderhaug, Jonatan Nygren, J. E. Johansen 13C-Labelled chlorinated paraffins and their preparation. Submitted to European Patent Office (Appl. No. EP22162109.7) III. S. Valderhaug, N. Paškanová, J. Tuma, J. Herciková, V. Eigner, H. Liu, A. Gorovoy, J. E. Johansen, O. R. Gautun Synthesis, identification, chiral separation and crystal structure of (3R,4R,7S,8S)- 3,4,7,8-tetrachlorodecane and its stereoisomers. Submitted to Journal of Molecular Structure IV. S. Valderhaug, H. Liu, A. Gorovoy, J. E. Johansen, L. van Mourik, J. de Boer, O. R. Gautun Nuclear magnetic resonance as a tool to determine chlorine percentage of chlorinated paraffin mixtures. Chemosphere 308 136312 (2022)

The outcomes from the project are commercial products of chlorinated paraffins (CPs), Perfluorinated alkyl substances (PFASs). Synthesis of CPs standards has been the main focus in this project, together with other projects at Chiron, about 100 CP native products, 8 13C-labelled CP internal standards have been synthesized, these are unique products for Chiron, also several groups of single chain mixture are available at Chiron. Several PFAS native standards, PAPs for example, have also been developed in this project for both environmental and food safety analytical application The technologies developed in this project will also be used in the preparation of other reference materials in environmental analysis or other analysis filed of food analysis, petroleum analysis and pharmaceutical and forensic analysis. The marketing of these standards and internal standards will help to give accurate and presis monitoring and analysis results of these substances which have greatest environmental concerns

Poly- / Per-halogenated substances are organic halogen compounds containing highly halogenated alkyl chain (poly-halogenated) or fully halogenated alkyl chain (per-halogenated). The main goals of this project are to develop reference materials and internal standards for two tyeps of organic halogen compounds - polychlorinated alkanes also called chlorinated paraffins (CPs) and perfluorinated alkyl substances (PFASs). Chlorinated paraffins (CPs) are a class of industrial chemicals used as high-temperature lubricants and as flame-retardant plasticizers in vinyl plastics. CPs are highly toxic to mammalians via bioaccumulation and are potential carcinogenic to humans. The project aims to develop certificated reference materials for short- and medium chained chlorinated paraffins, including pure native (unlabelled) single CPs as Reference standards, 13C-labelled CPs as internal standards, and new and robust analysis methods for fast and safe monitoring and quantification of CPs in complex matrixes in environmental analysis and environmental toxicology. Perfluorinated alkyl substances (PFASs) is a group of chemical substances that contain perfluoroalkyl chains. PFASs have strong surfactant properties and have been exploited in numerous applications due to the unique property and the stability of the carbon-fluorine bonds. PFASs are of great environmental concern due to their persistence, bioaccumulation and biomagnification. The project aims to develop synthesis method for stable isotop 13C-labelled PFASs as internal standards for safe monitoring and quantification of PFSAs in complex matrices, mainly targeting perfluorinated carboxylic acids, perfluorinated alkyl sulfonic acids, fluorinated telomer alcohols and related derivatives. The CPs and PFASs reference standards/internal standards developed will be tested and validated in various complex matrixes for environmental analysis.

Publications from Cristin

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Funding scheme:

NAERINGSPH-Nærings-phd