1. Lecture 3 Organic Compounds

2. AcetaldehydeIsopropanol AcetoneChloroform MethanolTrichloroethanol EthanolDichloroethane Carbon terachlorideToluene BenzeneFormaldehyde Commonly Found Volatiles

3. methanol ethanol isopropanol present in some drinks (“Kirsch”) technical alcohol mixtures Additional problem: mixed intoxication of ethanol and drugs

4. 1. acetaldehyde 2. methanol 3. acetone 4. ethyl formate 5. ethanol 6. ethyl acetate 7. n-propanol 8. sec-butanol 9. isobutanol 10. active amyl alcohol 11. isoamyl alcohol 12. n-amyl alcohol Rum Scotch

5. formaldehyde acetone methyl ethyl ketone 1. methanol 2. ethanol 3. diethyl ether 4. isopropanol 5. methylene chloride 6. acetone 7. methyl tert-butyl ether 8. hexane 9. chloroform 10. ethyl acetate 11. methyl ethyl ketone 12. benzene 13. trichloroethylene 14. toluene 15. methyl isobutyl ketone Headspace in blood – metabolic disorder, after an accident, etc.

6. Diethyl EtherPropanalAllyl ether Propanol, Butanol, Pentanol Methyl Acetate, Ethyl Acetate, Propyl Acetate Hexane, Heptane Octane PropionitrileDiethylamineAcetonitrile DichloromethaneXyleneCyclohexane TetrahydrofuranAcrylonitrileCamphor DioxaneCarbon DisulfideAcrolein DichloropropaneMethyl isobutyl ketoneMethylcyclohexane Infriquently found volatiles GC headspace

7. “Semivolatile” hazardous substances 1. 2-fluorophenol 2. phenol 3. 1,4-dichlorobenzene-d4 (IS) 4. nitrobenzene 5. napthalene-d8 (IS) 6. 2-fluorobiphenyl 7. acenaphthene-d10 (IS) 8. 1-naphthalenamine 9. 2-naphthalenamine 10. 5-nitro-o-toluidine 11. diphenylamine 12. 2,4,6-tribromophenol 13. 4-aminobiphenyl 14. phenanthrene-d10 (IS) 15. p-terphenyl 16. p-dimethylaminoazobenzene 17. 2-acetylaminofluorene 18. chrysene-d12 (IS) hazardous substances + internal standard mixture GC-MS

8. Paraquat Diquat MMP+ Peak List: Peak time (min.) 1. diquat 7.5 2. paraquat 8.8 acetonitrile, 95:5 (v/v) Flow: 1.0 mL/min. Temp.: 27°C Det.: UV @ 257nm (paraquat) UV @ 308nm (diquat) HPLC Herbicides:

9. 2,4-Dichlorophenoxyacetic acid (2,4-D) 2,4,5-Trichlorophenoxyacetic acid (2,4,5-T) 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) 1. 1,4,7,8-TCDD 2. 2,3,7,8-TCDD 3. 1,2,3,4-TCDD 4. 1,2,3,7 5. 1,2,3,8-TCDD 6. 1,2,7,8-TCDD GC: 2.0μL splitless injection of TCDD isomers, approximately 0.5ng each isomer Splitless hold: 0.45 min ECD detector

10. DDT Aldrin 1. 2,4,5,6-tetrachloro-m-xylene (ss) 2. α-BHC 3. γ-BHC 4. β-BHC 5. δ-BHC 6. heptachlor 7. aldrin 8. heptachlor epoxide 9. γ-chlordane 10. α-chlordane 11. endosulfan I 12. 4,4'-DDE 13. dieldrin 14. endrin 15. 4,4'-DDD 16. endosulfan II 17. endrin aldehyde 18. 4,4'-DDT 19. endosulfan sulfate 20. methoxychlor 21. endrin ketone Organochlorine Pesticides

11. sarin Malathion Malaoxon warfare agent Organophosphorus Pesticides GC

12. 30. fenthion 31. aspon 32. parathion-ethyl 33. chlorpyrifos 34. trichloronate 35. chlorfenvinphos 36. merphos 37. crotoxyphos 38. stirofos 39. tokuthion 40. merphos oxidation product 41. fensulfothion 42. famphur 43. ethion 44. bolstar 45. carbophenothion 46. triphenyl phosphate (IS) 47. phosmet 48. EPN 49. azinphos-methyl 50. leptophos 51. tri-o-cresyl phosphate 52. azinphos-ethyl 53. coumaphos 2. hexamethylphosphoramide 3. mevinphos 4. trichlorfon 5. TEPP 6. thionazin (IS) 7. demeton-O 8. ethoprop 9. tributyl phosphate (SS) 10. dicrotophos 11. monocrotophos 12. naled 13. sulfotepp 14. phorate 15. dimethoate 16. demeton-S 17. dioxathion 18. terbufos 19. fonophos 20. phosphamidon isomer 21. diazinon 22. disulfoton 23. phosphamidon 24. dichlorofenthion 25. parathion-methyl 26. chlorpyrifos methyl 27. ronnel 28. fenitrothion 29. malathion Organophosphorus Pesticides Oven temp.: 100°C to 180°C @ 10°C/min. (hold 2 min.), to 300°C @ 18°C/min. Inj. / det. temp.: 250°C / 280°C FPD Solvent: hexane

13. Carbaryl (1-naphthyl methylcarbamate) Methyl isocyanate (MIC) H 3 C-N=C=O Bhopal accident 1. aldicarb sulfone 2. aldicarb sulfoxide 3. oxamyl 4. methomyl 5. 3-hydroxycarbofuran 6. aldicarb 7. propoxur 8. carbofuran 9. carbaryl 10. methiocarb 11. 4-bromo-3,5- dimethylcarbamate HPLC Mobile phase: A: 90:10 water:methanol B: 90:10 methanol:acetonitrile UV @220 nm Pesticides (Carbamates)

14. Atrazine cyanuric acid Triazine Herbicides

15. chloroacetophenone, “tear gas”, “Mace” 2-chlorobenzalmalononitrile, CS gas Capsaicin, “pepper spray” Yperite C 4 H 8 Cl 2 S Carfentanil chemical warfare agent, has industrial use potential chemical warfare agent Tear gases: