Chemistry 324W Fall 2010 Experiment 3 GC-MS Analysis of Commercial Product Fragrances E. S. (student)
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1 Chemistry 324W Fall 2010 Experiment 3 GC-MS Analysis of Commercial Product Fragrances E. S. (student) Introduction In this work we analyzed the common fragrance compounds in shampoo.it is assumed that shampoo from various companies have similar fragreance, in this lab we will study the some volatile fragrance from a shampoo manufactured in Israel by AHAVA inc. In order to compare the fragrance we will use GC-MS to differentiate the fragrance molecules, and the NIST 1 library to identify them. Experimental methods In this work we analyzed Dead Sea shampoo by AHAVA Industries. A sample of 1.0 g was added into a head-speace vial for GC-MS analysis. Below is the GS-MS setup. GC-Ms setup Parameter value Injection volume ml Syringe size 2.5ml Cycle details Incubation temperture 40 C Incubation time 60 C Syringe setup 40 C Agitator speed 600 rpm Oven Step 1 35 C for 2 min Step 2 10 C/min to 150 C for 0 min Step 3 15 C/min to 200 C for 0 min Toal 16, 83 min Run time-colum HP-5MS 5% Phenyl methyl length 30 m Initial flow 1 ml/min Carrier gas Helium Scan parameters Low mass 40.0 High mass 200.0
2 Results Limonene Beta-pinene Figure 1. TIC chromatogram of AHAVA shampoo volatiles Peaks analyzed I II III Figure 2. β-pinene fragments. NIST database predicts molecule with 91 quality rating. Peaks analyzed IV V VI Figure 3. Limonene fragments, NIST database predicts molecule with 94 quality rating
3 Two peaks were analyzed in this study. Using NIST 1 library the peaks at 7.8 and 8.6 min were identified as β-pinene and limonene with quality ratings of 91 and 94 respectively. Table 1.Fragmentaiton analysis Molecule Retention time (min) Integration Fragments m/z Fragment ion Abundance Percent fragment β-pinene III I II Limonene VI V IV Table 2.Fragmentaiton analysis m/z β-piene % exp % Theoretical Limonene % exp % Theoretical m m m NA Discussion Using HyperChem PM3/RHF for β-pinene and limonene I modeled the spin density for both molecules. As can be observed for both molecules, the radical electron forms where the π bond was. This observation agrees with what we would expect, the electrons in the π bond are more delocalized or less bonded to the nucleus, thus, have higher chance to eject in the MS. First, I will discuss β-pinene fragment (7.8 min). From observing figure 4, there is a good chance of the odd electron localizing on carbons b, g and h. This observation agrees with data. The base peak is β-pinene, 93.1 m/z. This fragment, fragment I, is a result of three homolytic bonds breaking, and the formation of two π bonds between carbons g and f, b and c, and a hydrogen rearrangement from carbon f to carbon h on to the isopropyl group. Two hypotheses can be generated for the high abundance of isopropyl fragment. One reason could be that carbons b and g are tertiary carbons; carbocations are known to be more stable at tertiary carbons. A second
4 hypothesis is the strong strain of the 4-carbon ring with the six-carbon ring. Odd angles on carbons b and g would initiate this breakage. The result is a positive 1-methylcyclohexa-1,4-diene carbocation and a radical isopropyl. Fragment III, m/z, is the result of a loss of a radical methyl by homolytic bond break between carbons c and d. The product is a positive 6,6- dimethylbicyclo[3.1.1]hept-ene and a radical methyl. Another peak that can be observed in figure 2 is the peak at 41.1m/z, fragment II. This fragment is a result of the lost of a positive propene and a radical 1-methycyclohexene. This fragemntation has an unsuaul step, a heterolytic bond break between carbon h and b. Both electrons create a π bond between carbons b and c. This advance leaves the propyl with a positive charge. At this point two homolytic bond break h,g and and between one of the hydrogens on carob i or j. The hydrogen shifts to carbon g where the propyl was previously connected, which can be considered as a substitution. Next, I will consider the fragmentation of limonene (8.66 min). The base peak is 68 m/z (figure 3), fragment IV, this fragment is a reverse Diels-Alder fragmentation 2. The fragment is formed from two homolytic breaks of the sigma bond between carbons i-j, and e-d to form π bonds between carbons e-f, c-d and j-b. The odd electron as well the carbocation are as likely to be on either fragment. Both fragments are part of the base peak. This fragmentation is unique because both fragments are 68 m/z, which explains its high abundance. The next peak is the fragment at 93.1 m/z. This fragment breaks from an isopropyl by the following steps: An electron is removed from the isopropyl, thus carbon c is a carbocation. A 1,2 hydrogen shift is followed by the hydrogen from the cyclohexane carbon e shifting to carbon f. The next step is a bond forming between the radical electron at the end of the isopropyl, carbon g, with a hydrogen and one electron from carbon i. The terminal step is the bond between carbons e and f homolyticly breaks to from a π-bond on the cyclohexane carbon. The product is a positive 1-methylcyclohexa-1,4-diene and a radical methyl. Fragment e is left as carbocation a radical isopropyl. Fragment f is the peak of
5 121.1 m/z. This fragment is a result of a lost electron between carbon b-c, and as a result the two electrons between carbons a and b break homololyticly to from a radical methyl and an isopropyl group bonded to a cyclohexene with a positive charge. By observing the m+1, and m+2, Table 2, theoretical and calculated abundance for both β-pinene and limonene agree, thus we can concluded that the limonene fragrance was confirmed. Conclusion Using GC-MS enabled us to compare the fragrance molecules from different shampoo vendors. By considering lab data, and the data of lab colleagues, the most common molecules are β-pinene and limonene. These molecules are known to be easy to extract from pine trees (β-pinene) and lemon peel (limonene). The molecules are both 10 carbons and no hydrogen bonds, so they are very volatile, and most importantly, we register these molecules as a good smell. j a g h i f c b β pinene 136 mw e d g h f i j c e d Limonene 136 mw b a
6 Figure 4. β-pinene Figure 5. Limonene Reference 1. GC-MS chemistry fragment, 2010, #ms2 2. NIST McMurry, John Organic Chemistry, Seventh Edition. Thomson Learning, Inc. Belmont, Ca.,
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