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Lecture 3 Organic Compounds. Commonly Found Volatiles. methanol. present in some drinks (“Kirsch”). ethanol. isopropanol. technical alcohol mixtures. Additional problem: mixed intoxication of ethanol and drugs. Scotch. 1. acetaldehyde 2. methanol 3. acetone 4. ethyl formate

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slide1

Lecture 3

Organic Compounds

slide3

methanol

present in some drinks (“Kirsch”)

ethanol

isopropanol

technical alcohol mixtures

Additional problem: mixed intoxication of ethanol and drugs

slide4

Scotch

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

slide5

Headspace

formaldehyde

acetone

in blood – metabolic disorder,

after an accident, etc.

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

methyl ethyl ketone

slide6

GC headspace

Infriquently

found volatiles

slide7

“Semivolatile” hazardous substances

GC-MS

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

slide8

Herbicides:

Diquat

Paraquat

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

slide9

2,4-Dichlorophenoxyacetic acid (2,4-D)

2,4,5-Trichlorophenoxyacetic acid (2,4,5-T)

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

2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)

GC: 2.0μL splitless injection of TCDD isomers,

approximately 0.5ng each isomer

Splitless hold: 0.45 min ECD detector

slide10

DDT

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

Aldrin

Organochlorine Pesticides

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

slide11

sarin

warfare agent

GC

Malathion

Malaoxon

Organophosphorus Pesticides

slide12

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

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

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

slide13

Pesticides (Carbamates)

Carbaryl (1-naphthyl methylcarbamate)

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

Bhopal accident

Methyl isocyanate (MIC)

H3C-N=C=O

HPLC Mobile phase: A: 90:10 water:methanol

B: 90:10 methanol:acetonitrile

UV @220 nm

slide14

Atrazine

Triazine Herbicides

cyanuric acid

slide15

Tear gases:

chloroacetophenone, “tear gas”, “Mace”

2-chlorobenzalmalononitrile, CS gas

Capsaicin , “pepper spray”

Yperite

Carfentanil

C4H8Cl2S

potential chemical warfare agent

chemical warfare agent, has industrial use