Instrument
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
Tech-Prep Senior Event
Identification of Unknown Analgesic
Active Ingredients of Analgesics
Analgesics Active Ingredients
Tylenol
Acetaminophen
Aspirin
Acetylsalicylic Acid
Excedrin
Acetaminophen, Acetylsalicylic Acid,
Caffeine
Anacin
Acetylsalicylic Acid, Caffeine
GC Condition
GC Column: HP-5MS, 30m x 0.252mm x 0.25 m
CaffeineGC
Result
Acetaminophen
Acetylsalicylic Acid
Summary
Compounds in Unknown Analgesics
Compound
Retention Time (Min.)
Acetaminophen
4.6
Acetylsalicylic Acid
2.4, 3.2, 3.7
Caffeine
6.6
GC of the Analgesics
Excedrin
Aspirin
Anacin
Tylenol
Honors Project
Analysis of Perfumes
Dillon Andrews, 2010
GC Condition
Red for Men
HO
8%
13%
12%
104 Compounds
Red for Women
O
O
O
O
O
O
O
5%
10%
O
11%
Adidas
O
O
O
O
HO
32%
4%
86 Compounds
O
O
14%
Curve for Men
10%
6%
31%
41 Compounds
Honors Project Presentation
Gasoline Analysis
0 Analysis of top five major components of different
brand/grade gasoline
Ref.: Atterholt, et. al. (2000), JCE, vol. 77, No. 12, 1550-1551
GC Conditions
Shell Regular
Retention
Time (min.)
%
Composition
Compound
3.3
17.3
Toluene
5.4
18.2
P-Xylene
5.9
7.0
1,3-dimethylbenzene
7.3
7.5
1-ethyl-3-methylbenzene
7.8
10.7
1,2,4-trimethylbenzene
Speedway Regular
Retention
Time (min.)
% Composition
Compound
2.2
15.0
2,2,4-trimethylpentane
3.3
20.2
toluene
5.4
9.1
m-xylene
7.3
7.1
1-ethyl-3-methylbenzene
7.8
7.1
1,2,4-trimethylbenzene
Turbo Blue
Retention % Composition
Time (min.)
Compound
2.2
14.5
2,2-dimethylhexane
3.0
11.2
2,3,4-trimethylpentane
3.1
11.1
2,3,3-trimethylpentane
3.3
41.9
toluene
3.5
5.3
2,2,5-trimethylhexane
SAMS Gas
Retention
Time (min.)
% Composition
Compound
2.2
4.0
2,2,4-trimethylpentane
3.3
5.0
toluene
5.4
7.9
p-xylene
7.3
8.9
1-ethyl-3-methylbenzene
7.8
8.7
1,2,4-trimethylbenzene
Kerosene
Retention % Composition
Time (min)
Compound
7.9
3.0
Decane
8.9
6.4
Undecane
9.8
6.5
Dodecane
10.4
5.8
Tridecane
11.0
4.5
Tetradecane
11.6
2.7
Pentadecane
Synthesis and Identification of
Artificial Flavors
O
O
O
O
O
O
O
O
O
O
Synthesis of Ethyl Acetate
p.87
Synthesis of Ethyl Acetate
Apparatus for Higher Boiling Esters
Plastic
pipet
Test
tube
Hot plate/Sitrrer
vial
Heating
block
Reagents and Reaction Conditions
Ester Name
n-Octyl acetate
Acid (amount)
Acetic acid (1 mL)
Alcohol (amount)
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: 200-275oC
GC Condition
GC Column: HP-5MS, 30m x 0.252mm x 0.25 m
Result-Rum Flavor
Result-Apple Flavor
Result-Banana Flavor
Pineapple
Result-Pineapple Flavor
Summary of GC Analysis
Flavor
Compounds
Boiling
Retention
Point (oC)
Time
(min.)
Purity
(%)
Rum
Ethyl Propionate
98
2.7
100
Apple
Methyl Butyrate
100
2.8
100
Pineapple
Ethyl Butyrate
122
4.0
53
Banana
Isoamyl Acetate
142
5.5
81
Organic Reaction Product
Analysis
Analysis of Butene Mixture
H+
OH
HEAT
+
+
Williamson, Fig. 10.11, p. 218
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.
GC Condition
Column: AL/S, 0.32mm * 50 m * 8 mm, Sample size: 0.5 mL
GC of Butene Mixture
trans-2-butene (+0.4°C)
1-butene (−6.5°C)
cis-2-butene (+3.7°C)
Synthesis of 1-Bromobutane
NaBr,
H2SO4
OH
45 min.
http://college.cengage.com/chemistry/organic/williamson/macroscale/5e/resources/weblinks.html
Br
IR Spectrum
GC/MS Spectrum
Br
OH
Ref.: Illies et. al.(1995), JCE, vol. 72, No. 8, 717.
GC Condition
GC Column: HP-5MS, 30m x 0.252mm x 0.25 m
Reference:
Esterification of Benzoic Acid
Nitration of Methyl Benzoate
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.
Thank you!
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