Amine degradation in CO2 capture. 2. New degradation products of MEA. Pyrazine and alkylpyrazines: Analysis, mechanism of formation and toxicity

International Journal of Greenhouse Gas Control

Volumn 19, Issue , 2013, Pages 576-583

  Rey, A ^a   Gouedard, C ^b   Ledirac, N ^c   Cohen, M ^a   Dugay, J ^a   Vial, J ^a   Pichon, V ^a   Bertomeu, L ^c   Picq, D ^b,d   Bontemps, D ^e   Chopin, F ^e   Carrette, P L ^b  

^a PSL RESEARCH UNIVERSITY   (France)

^b IFP ENERGIES NOUVELLES   (France)

^c CEHTRA   (France)

^d LEPMI   (France)

^e EDF R AND D   (France)

Author keywords

HS SPME coupled with GC MS; MEA degradation; Mechanisms; Pyrazines toxicity; SAR

Indexed keywords

BENCHMARKING; CARBON DIOXIDE; DEGRADATION; MECHANISMS; PILOT PLANTS; TOXICITY;

ANALYTICAL METHOD; COMPUTATIONAL APPROACH; DEGRADATION PRODUCTS; HS-SPME; MECHANISM OF FORMATION; POTENTIAL IMPACTS; PYRAZINES; REPRODUCTIVE EFFECTS;

ETHANOLAMINES;

CARBON SEQUESTRATION; DEGRADATION; FORMATION MECHANISM; GAS CHROMATOGRAPHY; GENOTOXICITY; MASS SPECTROMETRY; TOXICITY; TOXICOLOGY;

EUROPE;

EID: 84887718791     PISSN: 17505836     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijggc.2013.10.018     Document Type: Article

References (51)

1. Adams A., Polizzi V., van Boekel M., De Kimpe N. Formation of pyrazines and a novel pyrrole in Maillard model systems of 1,3-dihydroxyacetone and 2-oxopropanal. J. Agric. Food Chem. 2008, 56:2147-2153.
2. Aeschbacher H.U., Wolleb U., Loliger J., Spadone J.C., Liardon R. Contribution of coffee aroma constituents to the mutagenicity of coffee. Food Chem. Toxicol. 1989, 27:227-232.
3. Beckman S., Binderup M.L., Brimer L., Castle L., Engel K.H., Franz R., Gontard N., Gurtler R., Husoy T., Jany K.D., Leclercq C., Lhuguenot J.C., Mennes W., Milana M.R., Pratt I., Svensson K., Toldra F., Wolfle D., Beltoft V., Bursch W., Carere A., Frandsen H., Hill F., Larsen J.C., Lund P., Mulder G., Norby K., Speijers G., Wallin H., Nielsen K.R. Scientific opinion on Flavouring Group Evaluation 17, Revision 3 (FGE.17Rev3): Pyrazine derivatives from chemical group 24. EFSA J. 2011, 9(5):66.
4. Bramwell A.F., Payne L.S., Riezebos G., Ward P., Wells R.D. The nuclear alkylation of pyrazines by ketones and aldehydes. J. Chem. Soc. C 1971, 1627-1632.
5. Chakma A., Meisen A. Corrosivity of diethanolamine solutions and their degradation products. Ind. Eng. Chem. Prod. Res. Dev. 1986, 25:627-630.
6. Chakma A., Meisen A. Degradation of aqueous DEA solutions in a heat-transfer tube. Can. J. Chem. Eng. 1987, 65:264-273.
7. Chakma A., Meisen A. Identification of methyl diethanolamine degradation products by gas-chromatography and gas-chromatography mass-spectrometry. J. Chromatogr. 1988, 457:287-297.
8. Chakma A., Meisen A. Methyl-diethanolamine degradation - mechanism and kinetics. Can. J. Chem. Eng. 1997, 75:861-871.
9. Choy E.T., Meisen A. Gas-chromatographic detection of diethanolamine and its degradation products. J. Chromatogr. 1980, 187:145-152.
10. 2 capture. Ind. Eng. Chem. Res. 2012, 51:13329-13338.
11. Davis J., Rochelle G. Thermal degradation of monoethanolamine at stripper conditions. Energy Procedia 2009, 1:327-333.
12. DeHart T.R., Hansen D.A., Mariz C.L., McCullough J.G. Solving corrosion problems at the NEA Bellingham Massachussetts carbon dioxide recovery plant. Presented at the NACE International Conference Corrosion '99 1999.
13. x in the flue gas degradation of MEA. Energy Procedia 2011, 4:1566-1573.
14. Freeman S.A., Davis J., Rochelle G.T. Degradation of aqueous piperazine in carbon dioxide capture. Int. J. Greenhouse Gas Control 2010, 4:756-761.
15. Freeman S.A., Rochelle G.T. Thermal degradation of piperazine and its structural analogs. Energy Procedia 2011, 4:43-50.
16. Fung V.A., Cameron T.P., Hughes T.J., Kirby P.E., Dunkel V.C. Mutagenic activity of some coffee flavor ingredients. Mutat. Res. Genet. Toxicol. Test. 1988, 204:219-228.
17. 2 capture I. A review. Int. J. Greenhouse Gas Control 2012, 10:244-270.
18. Guerra P.V., Yaylayan V.A. Dimerization of azomethine ylides: an alternate route to pyrazine formation in the Maillard reaction. J. Agric. Food Chem. 2010, 58:12523-12529.
19. 2 service. 48th Laurance Reid Gas Conditioning Conference 1998, 146-160.
20. Islam M.S., Yusoff R., ALi B.S., Islam M.N., Chakrabarti M.H. Degradation studies of amines and alkanolamines during sour gas treatment process. Int. J. Plant Sci. 2011, 6:5883-5895.
21. Pyrazine derivatives. JECFA Food Additives Series 2002, 48. JEFCA. http://www.inchem.org/documents/jecfa/jecmono/v48je12.htm.
22. Kohl A.L., Riesenfeld F.C. Gas Purification 1985, Gulf Publishing, Houston, TX.
23. Krems I.J., Spoerri P.E. The pyrazines. Chem. Rev. 1947, 40:279-358.
24. 2 absorption from flue gases. Ind. Eng. Chem. Res. 2005, 44:1874-1896.
25. Lee H., Bian S.S., Chen Y.L. Genotoxicity of 1,3-dithiane and 1,4-dithiane in the CHO/SCE assay and the Salmonella/microsomal test. Mutat. Res. Genet. Toxicol. 1994, 321:213-218.
26. Lepaumier H., da Silva E.F., Einbu A., Grimstvedt A., Knudsen J.N., Zahlsen K.R., Svendsen H.F. Comparison of MEA degradation in pilot-scale with lab-scale experiments. Energy Procedia 2011, 4:1652-1659.
27. 2. Ind. Eng. Chem. Res. 2009, 48:9061-9067.
28. 2 capture. II. Oxidative degradation mechanisms. Ind. Eng. Chem. Res. 2009, 48:9068-9075.
29. 2 capture. III. Effect of alkyl chain length between amine functions on polyamines degradation. Ind. Eng. Chem. Res. 2010, 49:4553-4560.
30. Maarse H., Visscher C.A., Willemsens L.C., Nijssen L.M., Boelens M.H. Volatile Components in Food 1999, TNO Nutrition and food Research. 6th ed.
31. Maga J.A. Pyrazines in foods: an update. CRC Crit. Rev. Food Sci. Nutr. 1982, 16:1-48.
32. Moran E.J., Easterday O.D., Oser B.L. Acute oral toxicity of selected flavor chemicals. Drug Chem. Toxicol. 1980, 3:249-258.
33. 2 capture. IV. Degradation, corrosion and quantitative structure property relationship model. Ind. Eng. Chem. Res. 2012, 51:6283-6289.
34. Oser B.L., Carson S., Oser M. Toxicological tests on flavouring matters. Food Cosmet. Toxicol. 1965, 3:563-569.
35. Posternak J.M., Linder A., Vodoz C.A. Toxicological tests on flavouring matters. Food Cosmet. Toxicol. 1969, 7:405-407.
36. Renberg L., Simonsson R., Hoffmann K.J. Identification of two main urinary metabolites of [14C]omeprazole in humans. Drug Metab. Dispos. 1989, 17:69-76.
37. Rooney P.C., Dupart M.S., Bacon T.R. Oxygen's role in alkanolamine degradation. Hydrocarbon Process 1998, 77:109-113.
38. Sexton A.J. Amine Oxidation in Carbon Dioxide Capture Processes 2008, University of Texas, Austin, Thesis.
39. Sexton A.J., Rochelle G.T. Reaction Products from the oxidative degradation of monoethanolamine. Ind. Eng. Chem. Res. 2011, 50:667-673.
40. Sjoedin P., Wallin H., Alexander J., Jaegerstad M. Disposition and metabolism of the food mutagen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in rats. Carcinogenesis 1989, 10:1269-1275.
41. Snyder R.D., Pearl G.S., Mandakas G., Choy W.N., Goodsaid F., Rosenblum I.Y. Assessment of the sensitivity of the computational programs DEREK, TOPKAT, and MCASE in the prediction of the genotoxicity of pharmaceutical molecules. Environ. Mol. Mutagen. 2004, 43:143-158.
42. 2 capture facility. Energy Fuels 2003, 17:1034-1039.
43. Stedman R.L. The chemical composition of tobacco and tobacco smoke. Chem. Rev. 1968, 68:153-207.
44. Stich H.F., Stich W., Rosin M.P., Powrie W.D. Mutagenic activity of pyrazine derivatives: a comparative study with Salmonella typhimurium, Saccharomyces cerevisiae, and Chinese hamster ovary cells. Food Cosmet. Toxicol. 1980, 18:581-584.
45. 2 capture from flue gas streams. Energy Procedia 2011, 4:591-598.
46. Tang J., Jin Q.Z., Shen G.H., Ho C.T., Chang S.S. Isolation and identification of volatile compounds from fried chicken. J. Agric. Food Chem. 1983, 31:1287-1292.
47. Vevelstad S.J., Eide-Haugmo I., da Silva E.F., Svendsen H.F. Degradation of MEA: a theoretical study. Energy Procedia 2011, 4:1608-1615.
48. 2 capture. Ind. Eng. Chem. Res. 2012, 51:6529-6536.
49. Yamada K., Shimizu A., Komatsu H., Sakata R., Ohta A. Effects of 2,5-dimethylpyrazine on plasma testosterone and polyamines- and acid phosphatase-levels in the rat prostate. Biol. Pharm. Bull. 1994, 17:730-731.
50. Yamada K., Shimizu A., Ohta A. Effects of dimethylpyrazine isomers on reproductive and accessory reproductive organs in male rats. Biol. Pharm. Bull. 1993, 16:203-206.
51. Yamada K., Takahashi H., Ohta A. Effects of 2,5-dimethylpyrazine on reproductive and accessory reproductive organs in female rats. Res. Commun. Chem. Pathol. Pharmacol. 1992, 75:99-107.