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E nvironmen ental al impac acts o of am amines es an and thei eir d deg egrad adat ation products: C urren ent stat atus an and k knowled edge e gap aps ore Syversen b and O Andy Booth a , E alck da Silva a , T unnar Brakstad a


  1. E nvironmen ental al impac acts o of am amines es an and thei eir d deg egrad adat ation products: C urren ent stat atus an and k knowled edge e gap aps ore Syversen b and O Andy Booth a , E alck da Silva a , T unnar Brakstad a irik F dd G a SINTE FMaterials and C hemistry, Dept. Marine E nvironmental T echnology b Institutefor Neuromedicine, NTNU SINTEF M M aterials and C hemistry 1

  2. Three m ee mai ain focus ar areas eas for em emissions E mission Atmospheric T errestrial and aquatic profileand transport, processes transport, processes concentration and deposition and exposure Thes ese e three p ee proces esses es ultimat atel ely det eter ermine w e who (peo eople) e) o or what at (en environmen ent) i is exposed ex ed t to w which chem emical als an and at at which concen entrat ation SINTEF M M aterials and C hemistry 2

  3. C apture ap e plan ant em emissions • Most focus has been on the use of ME A • An increasing number of studies are considering other solvent systems • C omputational chemistry and modellingused to predict ME A degradation products (and other amine solvents) • W ide range of degradation products - ammonia, nitrosamines, nitramines, alkylamines, aldehydes and ketones 1 • C ompounds of most concern (e.g. nitrosamines) are formed in very small amounts or thought to form in very small amounts (e.g. nitramines) • Ther ere e ar are e curren ently n no em emission s stan andar ards f for C C O 2 cap apture p e plan ants 1 Brakstad, O . G .; Silva, E . F . d.; Syversen, T . "Support oninput to environmental discharges - E valuationof degradationcomponents," SINTE F , 2010. SINTEF M M aterials and C hemistry 3

  4. Atmos osph pheric transpor port and pr proc ocesses Atmosphericprocesses 3 Local or long • Photo-induceddegradation Emissi ssion distance • C hemical degradation transport 2 Partitioning R ain Aerosols/particles W et deposition Dry deposition 3 Bråten, H. B.; Bunkan, A. J.; Bache- 2 Berglen, T . F .; T ønnesen, D.; Dye, C .; Karl, M.; Knudsen, Andreassen, L.; Solimannejad, M.; Nielsen, C . S.; T arrasón, L. "C O 2 T echnology C entre Mongstad – J. "Final report on a theoretical study on the updatedair dispersioncalculations. Updateof O R atmospheric degradation of selected 12/2008," NorwegianInstitute for Air Research, 2010. amines," NILU, 2009 SINTEF M M aterials and C hemistry 4

  5. T er erres estrial al an and aq aquat atic proces esses es • V ola latilis ilisatio ion • Ru Run-of off • Up Uptake OrgMat • Dis issolu lutio ion an and transpor port CLAY • C hem emical al reaction/hyd ydrolysi ysis OXIDE • Adsor orpt ption on Groundwater • Biodeg egrad adat ation Per ersisten ence e an and E Exposure e = ƒ ƒ (volat atilisat ation, run-off, leac eaching, c chem emical al reac eaction, b biodeg egrad adat ation, ad adsorption an and u uptak ake) e) SINTEF M M aterials and C hemistry 5

  6. ME A as as an an ex exam ample NH 2 H O SINTEF M M aterials and C hemistry 6

  7. E nv nvironm nment nt –ME E A A biod odeg egrad adat ation & & ecot otox ox dat ata A Ecotoxicity GROUP Degradation product Biodegradability (%) (EC 50 or LC 50 ; mg/L) N-nitroso-dimethylamine Judged biodegrable 4 (phytoplankton) 4-nitroso-morpholine No data 75 (fish) Nitrosamines N-nitroso-diethanolamine No data No data 2-(methyl-nitrosoamino)-ethanol No data No data No data Nitramines Dimethylnitramine No data Methylamine 55-100 10 (fish) Dimethylamine 30-100 9 (phytoplankton) Ethylamine 98-100 10 Diethanolamine (DEA) 93-97 Amines, amides, 2 (phytoplankton) aldehydes, ketones N-(2-hydroxyethyl)-formamide (HEF) No data No data N-(2-hydroxy-ethyl)imidazole (HEI) No data No data 2-methylaminoethanol 93 33 (Daphnia) 1,2-Ethanediol or ethyleneglycol (EG) 56 18 (Daphnia) Ammonia Nitrification 0.024 (fish) Formaldehyde 90 0.30 (phytoplankton Other compounds Acetaldehyde 80 31 (fish) Acetone 84-90 2840 (phytoplankton) Formamide 30-100 4600 (fish) A) Highest ecotoxicity selected from 3 trophic levels The e quan antity an and qual ality o of eq equival alen ent dat ata a av avai ailab able e for other er s solven ent types es i is usu sually y less ss than f for M MEA SINTEF M M aterials and C hemistry 7

  8. T er erres estrial al an and aq aquat atic proces esses es • M ost ter erres estrial al an and aq aquat atic en environmen ent s studies es h hav ave e focused ed on par aren ent am amines es o only, h howev ever er: • A recent study assessed the biodegradability and ecotoxicity of A degradation products using modelling and reported data 1 ME • All compounds with available data appeared to be biodegradable (30-100% ), whilst ecotoxicity varied significantly • E xperimental data is missing for many compounds and compound groups (e.g. nitrosamines and nitramines) • Some degradation products may persist in the environment due to low biodegradability, posing a possible risk if accumulated in aquatic systems (e.g. groundw ater). 1 Brakstad, O . G .; Silva, E . F . d.; Syversen, T . "Support oninput to environmental discharges - E valuationof degradationcomponents," SINTE F , 2010. SINTEF M M aterials and C hemistry 8

  9. Hu Human heal ealth –ME E A A d deg egrad adat ation pr prod oducts d data Acute LD 50 Occupational exposure GROUP Degradation product Long-term (mg/kg bw) limits (OEL – mg/m 3 ) N-nitroso-dimethylamine < 0.5 (inhalation) CMR 0.001 4-nitroso-morpholine < 0.5 (inhalation) CM(R) 0.001 Nitrosamines N-nitroso-diethanolamine >2000 (oral) CM(R) 0.001 2-(methyl-nitrosoamino)- Ethanol No data CM(R) --- Nitramines Dimethylnitramine 300-2000 (oral) (C) --- Methylamine 0.5-20 (inhalation) M 0.13 Dimethylamine 2-10 (inhalation) S 3.5 Ethylamine 50-300 (oral) ? 18 Amines, amides, Diethanolamine (DEA) No data ? --- aldehydes, N-(2-hydroxyethyl)- Formamide (HEF) No data ? --- ketones N-(2-hydroxy-ethyl)imidazole (HEI) 300-2000 (oral) ? --- 2-methylaminoethanol 300-2000 (oral) ? 9.4 1,2-Ethanediol or ethyleneglycol (EG) 300-2000 (oral) R --- Ammonia 0.5-2 (inhalation) (M) 18 Formaldehyde < 0.5 (inhalation) CM(R)S 0.6 Other compounds Acetaldehyde 300-2000 (oral) CMRS 45 Acetone Negligible --- 295 Formamide 10-20 R 18 Long-term toxicity Acute toxicity Occupational exposure limits (OEL) – C –carcinogenicity – LD – OEL is exposure limits for healthy people 50 is the concentration of a chemical which – M –mutagenicity causes 50% mortality in a population – OEL may vary from country to country – R –reproduction toxicity – OEL used here are the strictest available limits – S –sensitisation SINTEF M M aterials and C hemistry 9

  10. Human heal Hu ealth • Human an heal ealth haz azar ards ar are as e associat ated ed with s sev ever eral al o of the e sugge ggested degr gradation on pr prod oducts for or M M E A, h how owever: • Data for many products are not available • Potential long-term effects associated with mutagenicity, genotoxicity/carcinogenicity and reproduction effects are documented for specific nitrosamines, volatile aldehydes and alkylamines • Indicates that nitrosamines may contribute to the health risk of the population, although their emission concentration is small 1 • The real risks cannot be estimated until the fate of these compounds has been determined • The e quan antity an and qual ality o of eq equival alen ent dat ata a av avai ailab able f e for o other er so solvent typ ypes s is u s usu sually l y less ss than for M M E A SINTEF M M aterials and C hemistry 10

  11. Ho Howdo o we we us usethi his data??? ??? RISK SK A ANAL YSI SIS! S! • R A combines the toxicity and ecotoxicity information with the potential fate of the components in the environment • R A identifies the concentrations people and the environment are exposed to • F ate data (and therefore environmental concentrations) are difficult to predict............but we can use available models (e.g. Q SAR and computational chemistry) • Need to understand the limitations with using such modelling methods to generate predicted values SINTEF M M aterials and C hemistry 11

  12. C as ase e liter erat ature e study Nitrosam amines es –fat ate i e in t the aq e aquat atic en environmen ent SINTEF M M aterials and C hemistry 12

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