Uses of GC/MS. Synthesis of 1-Bromobutane Butenes from 2-Butanol Fisher Esterification of Benzoic Acid Nitration of Methyl Benzoate

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1

2 Instrument

3 Uses of GC/MS 0 TechPrep Senior Event 0 Honors Project 0 Gasoline Analysis-General Chemistry 0 Ester Synthesis and Analysis-Chemistry for Liberal Arts Majors 0 Organic Reaction Product Analysis Synthesis of 1-Bromobutane Butenes from 2-Butanol Fisher Esterification of Benzoic Acid Nitration of Methyl Benzoate

4 Tech-Prep Senior Event Identification of Unknown Analgesic

5 Active Ingredients of Analgesics Analgesics Tylenol Active Ingredients Acetaminophen Aspirin Acetylsalicylic Acid Excedrin Anacin Acetaminophen, Acetylsalicylic Acid, Caffeine Acetylsalicylic Acid, Caffeine

6 GC Condition GC Column: HP-5MS, 30m x 0.252mm x 0.25 m

7 GC Result Caffeine

8 Acetaminophen Acetylsalicylic Acid

9 Summary Compounds in Unknown Analgesics Compound Retention Time (Min.) Acetaminophen 4.6 Acetylsalicylic Acid 2.4, 3.2, 3.7 Caffeine 6.6

10 GC of the Analgesics Excedrin Aspirin Anacin Tylenol

11 Honors Project Analysis of Perfumes Dillon Andrews, 2010

12 GC Condition

13 Red for Men HO 8% 13% 12% 104 Compounds

14 Red for Women O O O O O O 5% 10% O O 11%

15 Adidas O O HO O O O 32% 4% 14% O 86 Compounds

16 Curve for Men 10% 6% 31% 41 Compounds

17 Honors Project Presentation

18 Gasoline Analysis 0 Analysis of top five major components of different brand/grade gasoline Ref.: Atterholt, et. al. (2000), JCE, vol. 77, No. 12,

19 GC Conditions

20 Shell Regular Retention Time (min.) % Composition Toluene P-Xylene Compound ,3-dimethylbenzene ethyl-3-methylbenzene ,2,4-trimethylbenzene

21 Speedway Regular Retention Time (min.) % Composition Compound ,2,4-trimethylpentane toluene m-xylene ethyl-3-methylbenzene ,2,4-trimethylbenzene

22 Turbo Blue Retention Time (min.) % Composition Compound ,2-dimethylhexane ,3,4-trimethylpentane ,3,3-trimethylpentane toluene ,2,5-trimethylhexane

23 SAMS Gas Retention Time (min.) % Composition Compound ,2,4-trimethylpentane toluene p-xylene ethyl-3-methylbenzene ,2,4-trimethylbenzene

24 Kerosene Retention Time (min) % Composition Compound Decane Undecane Dodecane Tridecane Tetradecane Pentadecane

25 Synthesis and Identification of Artificial Flavors O O O O O O O O O O

26 Synthesis of Ethyl Acetate p.87

27 Synthesis of Ethyl Acetate

28 Apparatus for Higher Boiling Esters Plastic pipet Test tube vial Hot plate/sitrrer Heating block

29 Reagents and Reaction Conditions Ester Name Acid (amount) Alcohol (amount) n-octyl acetate Acetic acid (1 ml) Octanol (1.5 ml) Isoamyl acetate Acetic acid (1 ml 3-Methylbutanol (1 ml) Ethyl propionate Propionic acid (1 ml) Ethanol (1 ml) Methyl butyrate Butyric acid (5 drops) Methanol (1 ml) Ethyl butyrate Butyric acid (5 drops) Ethanol (1 ml) Catalyst: Dowex Cation Exchange Resin Reaction Time: 5 15 min. Hot Plate Setting: o C

30 GC Condition GC Column: HP-5MS, 30m x 0.252mm x 0.25 m

31 Result-Rum Flavor

32 Result-Apple Flavor

33 Result-Banana Flavor Pineapple

34 Result-Pineapple Flavor

35 Summary of GC Analysis Flavor Compounds Boiling Point (oc) Retention Time (min.) Purity (%) Rum Ethyl Propionate Apple Methyl Butyrate Pineapple Ethyl Butyrate Banana Isoamyl Acetate

36 Organic Reaction Product Analysis

37 Analysis of Butene Mixture OH H + HEAT + + Williamson, Fig , p. 218

38 Analysis of the Butene Mixture A good, general-purpose column is a 10 ft ¼ in. column packed with 10% SE-30, a methyl silicone rubber coated on 60/80 mesh Chromosorb W. For the separation of the methyl butanes and cis- and trans-2-butenes, this column must be operated at room temperature with a helium flow rate of 40 ml per minute. For capillary column analysis use 1-10 μlof the gaseous vapor above the liquid. Carry out the analysis at room temperature.

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40 GC Condition Column: AL/S, 0.32mm * 50 m * 8 mm, Sample size: 0.5 ml

41 GC of Butene Mixture trans-2-butene (+0.4 C) 1-butene( 6.5 C) cis-2-butene (+3.7 C)

42 Synthesis of 1-Bromobutane OH NaBr, H 2 SO 4 Br 45 min.

43 IR Spectrum

44 GC/MS Spectrum Br OH Ref.: Illies et. al.(1995), JCE, vol. 72, No. 8, 717.

45 GC Condition GC Column: HP-5MS, 30m x 0.252mm x 0.25 m Reference:

46 Esterification of Benzoic Acid

47 Nitration of Methyl Benzoate

48 Summary GC/MS promoted students learning by Biotech students-teaching the uses of gc/ms in industry Honor student -providing a tool for creative project General chemistry students-providing a better way to identify the major compounds in different gasoline samples Liberal arts chemistry students- providing a way to make connections between the flavor and the structure Organic chemistry students-providing a way to analyze their reaction products.

49 Thank you! NSF SCC SCC Grants Office Miami Valley Regional Crime Lab