E!10050 New stable Isotope Labelled Certified Reference Materials for Hydrocarbon Analysis

WP1: Project Management Det siste prosjektmøtet ble avholdt i Chiron på 13. desember 2018. WP2: Exploitation and Dissemination GEUS publiserte prosjektresultater i Organic Geochemistry 129 (2019) 14-23. Et nytt manuskript for triaromatisk oleanan er også planlagt for Organic Geochemistry. WP4: Synthesis of labelled compounds Syntese av 13C-merkede PAH og PBDE er pågår, arbeidet vil fortsette etter at prosjektet er avsluttet. Syntese av 13C-merket kolestan har blitt gjort. Syntesen har blitt optimalisert og produktets renhet på 98-99% ble oppnådd. WP5: Isolation and Purification of native biomarkers from geological samples for 12C/13C measurements Fem triaromatiske triterpaner ble oppnådd veldig rent fra serbisk og colombiansk kull. Strukturen av triaromatisk oleanan, triaromatisk ursan og triaromatisk lupan ble bekreftet av NMR. Den fjerde forbindelsen ser ut til å være en triaromatisk lupan-stereoisomer. Bestemmelse av ekstraktstrukturen er i gang. Den siste forbindelsen er en ring-E demetylert oleanan / ursan. Ekstraksjon av umodne kinesisk kull er oppnådd. Isolering av diaromatiske triterpaner (noen fortsatt uidentifiserte) fant sted tidlig i 2019. En isolert forbindelse er nesten ren, noen mindre forbindelser trenger mer opp-rensing. NMR-analyse av isolerte forbindelser er planlagt. WP6: Product certification and implementation of the CRMs in analytical procedures pågår med 13C-merkede PAHs.

Biomarkers such as hopanes and steranes are unique products for Chiron, PAHs, alkyl PAHs and PBDEs are among the best sold products in Chiron?s product ranges. With the outcome of 13C-labelled reference materials and isotope ratio (13C/12C) reference materials developed in the project, Chiron has now a stronger and more competitive marked position for supply CRMs for forensic environmental analysis and petroleum exploration.

The 13C-CRM project aims at seizing a major market opportunity in developing unique isotope-labelled Certified Reference Materials (CRMs) for a more accurate analysis of environmental and petroleum compounds using mass spectrometry techniques. 13C labelled CRMs will be produced, certified, and commerciallized as reference stardards for hydrocarbon analysis, in quantitative GC-MS (gas chromatography - mass spectrometry analysis ) and GC-IRMS (gas chromatography-isotope ratio mass spectrometry). The lack of widely available CRMs has hindered the practice when analysing organic materials with GC-MS and GC-IRMS. The existing CRMs are usually based on structural analogues of the analytes or deuterium labelled versions. However, it has been shown that due to ion suppression effects, the quantitaive analytical results with deuterated standards may vary. Using of 13C labelled standards always yields the true value. In addition, 13C labelled standards can overcome the problems of deuterated standards of stability, recovery, instrument variations and ion suppression. In this 13C-CRM project, CRMs will be developed based on the combination of chemical synthesis and biosynthesis (fermentation) methods, which is not only unique in itself as far as the authors are aware, but essential for developing an attractive spectrum of new petroleum analytical standards. An integrated approach for continuous validation of results and advancements with cross-checking procedures between different techniques will be pursued as research methodology. Different development approaches will be applied for the different target products, e.g. 13C-labelled alkylated PAHs, 13C-labelled hopanoids and sterols.