DET REPORT NO. 69 JUNE 2015

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1 1.) THINKING BEYOND THE NPD BOX - INEXPENSIVE CONVERSION OF NPD EQUIPMENT TO MULTIPLE MODES OF SELECTIVE GC DETECTION. 2.) GC-CCID DIFFERENTIATION BETWEEN SATURATE VS. UNSATURATE AND MONO-UNSATURATE VS. POLYUNSATURATE FAMEs. 3.) TID-10 (TID-1) THERMIONIC SURFACE IONIZATION DETECTION OF DEGRADATION PRODUCTS IN PETROLEUM AND BIOFUEL SAMPLES. 4.) TID-10 (TID-1) SELECTIVE DETECTION OF COMPOUNDS CONTAINING A FIVE MEMBER CARBON OR NITROGEN RING STRUCTURE. By P.L. Patterson 1.) THINKING BEYOND THE NPD BOX - INEXPENSIVE CONVERSION OF NPD EQUIPMENT TO MULTIPLE MODES OF SELECTIVE GC DETECTION. Figure 1 depicts the NPD equipment configuration used on Agilent 6890/7890 and Thermo Trace 1300 GC models, as well as in DET retrofit hardware for other GC models. The basic components are an electrically heated ion source (bead) and a ion collector cylinder, contained in a detector structure that has provisions for adding H 2, Air, and Makeup detector gases in addition to effluent from the GC column. DET s development of ceramic ion sources with different catalytic ionizing activities, combined with the availability for supplying 3 different types of detector gases, allows NPD equipment to be transformed to modes of selective detection other than just NP. This conversion is both easy and inexpensive, and it provides a much wider range of possible applications for the same basic equipment. There are 4 key operating parameters that determine compound selectivity and sensitivity for the equipment depicted in Figure 1: 1. Catalytic ionizing activity of the ion source as determined by additives in the ceramic coating; 2. Temperature of the ion source as determined by the electrical heating current supplied; 3. Composition of the detector gases supplied (e.g., N 2, Air, O 2, N 2 O, H 2, and combinations thereof); 4. The magnitude of the polarizing voltage between the ion source and collector. Multiple modes of selective detection are achieved through various permutations of these 4 key parameters. Selectivity possibilities include compounds containing, O, N, P, Cl, Br, or I atoms, or NO 2, CH 2, Pyrrole, and certain other functional groups. Figure 1. Basic components of NPD equipment. Different modes of selective detection are achieved through inexpensive changes in the type of ion source and the composition of detector gases supplied. DET s ceramic ion sources are $410 each. No other detector technology provides so much versatility for so little cost. 1

2 2.) GC-CCID DIFFERENTIATION BETWEEN SATURATE VS. UNSATURATE AND MONO-UNSATURATE VS. POLY-UNSATURATE FAMEs Catalytic Combustion Ionization Detection (CCID) is a GC detector method in which the sample compound itself provides the fuel for a momentary burst of flame ionization as it impacts the surface of a catalytically active ceramic. Since the process involves combustion ignition, the detector gas environment must contain Oxygen to support that combustion. Also, there is a sample threshold amount below which there is not enough sample to fuel the combustion. For a compound such as n-c 16, that threshold level is in the range of ng, depending on the temperature of the ceramic ionizing surface, and the Oxygen concentration in the detector gases. The unique characteristic of CCID is that it selectively detects compounds containing chains of the Methylene (CH 2 ) functional group. This includes Alkanes, Alkenes, FAMEs, and Triglycerides, amongst others. The other unique characteristic of CCID is that it does not ignite responses from Aromatic or Cyclo-Hydrocarbons. Therefore, this CCID technology provides an unprecedented means of generating simplified GC fingerprints of selected constituents in otherwise complex Petroleum and Biofuel samples. CCID is a detection mode that is achieved through simple and inexpensive conversion of NPD equipment. The key element in CCID is a TID-10 ion source (i.e., more robust version of an earlier TID-1 ion source) which has an especially high catalytic activity. TID-10 causes combustion ignition to occur at relatively low temperatures in the range of o C, and that combustion is due to oxidation of CH 2 functional groups. As a general rule, the more CH 2 groups in a sample compound, the greater the signal response. Consequently, when CCID detection is applied to real world Petroleum and Biofuel samples, it produces chromatograms in which responses of high boiling constituents (i.e., bigger molecules with longer elution times) are magnified relative to lower boiling constituents. Previous DET Reports have described CCID detection of compounds containing Linear Chains of CH 2 groups (examples, n-alkanes, saturated FAMEs). Also discussed previously was that the presence of a Branched Methyl (CH 3 ) group, or a Carbon Double Bond in a sample compound s molecular structure suppresses CCID response even when the sample compound contains many CH 2 groups (e.g., Alkenes or iso-alkanes vs. n-alkanes). Further investigation of CCID characteristics revealed that increasing the Oxygen concentration in the detector gases resulted in increasing the relative responses of both Branched and Double Bonded compounds to magnitudes more comparable to Linear Chain responses. Recent reexamination of previous data reveals that CCID also provides additional differentiation between compounds containing one Carbon Double Bond (Mono-Unsaturates) and compounds containing Two or more Carbon Double Bonds (Poly-Unsaturates). This is illustrated in Figure 2 for the analysis of a mixture of Saturated and Unsaturated FAME compounds. With a low concentration of Oxygen in the detector gas, CCID detection (TID-1-Air) detected only the Saturates. With a higher concentration of Oxygen (TID- 1-Oxygen), the Saturate peaks in the chromatogram were accompanied by additional peaks due to the Mono- Unsaturates in the sample, but not the Unsaturates. having more than one Carbon Double Bond. The sample analyzed in Figure 2 was Supelco U which was a 10 mg/ml solution of FAMEs mixed in the weight proportions shown. Several other features of the Figure 2 data are as follows: 1.) The solvent for the FAME sample was Methylene Chloride which can produce a large solvent peak from the TID-10 ion source. To avoid this baseline upset, the heating current to the ion source was turned off during solvent elution through the detector. This was accomplished by activating a Heating Current OFF run time event on Thermo NPD electronics. Alternatively, sample dilutions in solvents that do not contain Cl atoms provide much less solvent tailing problems. 2.) For this diluted mixture of FAMEs, the CCID chromatogram was missing some peaks for early eluting compounds containing the lowest numbers of CH 2 groups because those compounds fell below the threshold requirement for combustion ignition. 3.) Compared to the FID chromatogram, the CCID chromatogram exhibited increasing peak responses with increasing length of CH 2 chains in the FAME constituents. 4.) In the FID chromatogram, later eluting FAME compounds were not well resolved with the GC conditions that were used. CCID response differentiation between Saturates and Unsaturates provided clearer resolution amongst these later eluting sample constituents. 2

3 FAMEs SAMPLE: 1.) Butyric (C4:0), 4wt%; 2.) Caproic (C6:0), 4wt%; 3.) Caprylic (C8:0), 4wt%; 4.) Capric (C10:0), 4wt%; 5.) Undecanoic (C11:0), 2wt%; 6.) Lauric (C12:0), 4wt%; 7.) Tridecanoic (C13:0), 2wt%; 8.) Myristic (C14:0), 4wt%; 9.) Myristoleic (C14:1), 2wt%; 10.) Pentadecanoic (C15:0), 2wt%; 11.) cis-10-pentadecenoic (C15:1), 2wt%; 12.) Palmitic (C16:0), 6wt%; 13.) Palmitoleic (C16:1), 2wt%; 14.) Heptadecanoic (C17:0), 2wt%; 15.) cis-10-heptadecenoic (C17:1), 2wt%; 16.) Stearic (C18:0), 4wt%; 17.) Oleic (C18:1n9c), 4wt%; 18.) Elaidic (C18:1n9t), 2wt%; 19.) Linoleic (C18:2n6c), 2wt%; 20.) Linolelaidic (C18:2n6t), 2wt%; 21.) ã-linolenic (C18:3n6), 2wt%; 22.) á-linolenic (C18:3n3), 2wt%; 23.) Arachidic (C20:0), 4wt%; 24.) cis-11-eicosenoic (C20:1n9), 2wt%; 25.) cis-11,14-eicosadienoic (C20:2), 2wt%: 26.) cis-8,11,14-eicosatrienoic (C20:3n6), 2wt%; 27.) cis-11,14,17-eicosatrienoic (C20:3n3), 2wt%; 28.) Arachidonic (C20:4n6), 2wt%; 29.) cis-5,8,11,14,17 Eicosapentaenoic (C20:5n3), 2wt%; 30.) Heneicosanoic (C21:0), 2wt%; 31.) Behenic (C22:0), 4wt%; 32.) Erucic (C22:1n9), 2wt%; 33.) cis-13,16-docosadienoic (C22:2), 2wt%; 34.) cis-4,7,10,13,16,19-docosahexaenoic (C22:6n3), 2wt%; 35.) Tricosanoic (C23:0), 2wt%; 36.)Lignoceric (C24:0), 4wt%; 37.) Nervonic (C24:1n9), 2wt%. Figure 2. Comparison of FID and CCID responses for a mixture of Saturate and UnSaturate FAMEs. CCID data are chromatograms labeled TID-1". TID-1 is an earlier, less robust version of a TID-10 ion source. TID-10 has the same response as TID-1. CCID with Air detector gas responds only to the Saturate FAMEs. CCID with Oxygen detector gas includes added peaks due to Mono- Unsaturates, but not the Poly-Unsaturates. 3

4 Figure 3 compares FID, CCID, and TID-1-Nitrogen chromatograms for a sample of B20 Biodiesel prepared as a dilution in Methylene Chloride. As indicated previously, TID-1 was an earlier, less robust ceramic formulation that provided the same response now obtained from a TID-10 ion source. Also as mentioned earlier, the upsetting effect of a chlorinated solvent can be eliminated by turning off the heating current during solvent elution. That procedure was used for the CCID and TID data of Fig. 3. In Fig. 3, peaks labeled C refer to Linear Alkanes, while peaks labeled F are FAMEs. Whereas the FAME peaks in the FID chromatogram were not well resolved, there was sufficient resolution in the CCID chromatogram to identify the main FAME components, Palmitic (F12), Oleic (F17), and Stearic (F16). This peak resolution was a consequence of the CCID differentiation between Saturates vs. Unsaturates, and Mono-Unsaturates vs. Poly-Unsaturates. When the detector gas environment was changed to Nitrogen, the prominent peaks due to Linear Alkanes and the major FAMEs disappeared, but still leaving a number of peaks that have not yet been identified. Fig. 3 3.) TID-10 (TID-1) THERMIONIC SURFACE IONIZATION DETECTION OF DEGRADATION PRODUCTS IN PETROLEUM AND BIOFUEL Petroleum and Biofuel mixtures can degrade in time upon exposure to Air, and/or interaction with a storage vessel. Figures 4-6 illustrate how the selectivity and high sensitivity of TID-10 surface ionization can reveal degradation products as they accumulate. Figure 4 compares chromatograms of an aged B100 Biodiesel sample that had acquired a slight rancid aroma. CCID detection provided resolution of the main FAME constituents plus enhanced peaks d1 - d3" associated with oxidative degradation of the sample. Changing to Nitrogen as the detector gas provided even greater enhancement of the degradation peaks while eliminating the CCID type response to the FAMEs. TID-10 is known to be especially sensitive to Phenol, Carboxylic Acid, and Glycol type Oxygenated compounds. Figure 5 illustrates the selective detection of degradation products that build up in time with usage of Motor Oils. Figure 6 illustrates extraneous contamination that can build up with storage of Gasoline samples in commonly used Polyethylene containers. Fig. 4 4

5 Fig.5 Fig. 6 4.) TID-10 (TID-1) SELECTIVE DETECTION OF COMPOUNDS CONTAINING A FIVE MEMBER CARBON OR NITROGEN RING STRUCTURE The Thermionic Surface Ionization process using a TID-10, or its predecessor TID-1 ion source, is very sensitive to compounds containing electronegative atoms or functional groups, and the response often depends on where those electronegative entities are located within a compound s molecular structure. One of the particular types of compounds that respond selectively to TID-10 ionization are those containing a five member ring structure. Figure 7 illustrates this in comparing FID, NPD, and TID-1 analyses of a mixture of polynuclear Nitrogen and Hydrocarbon compounds. In this figure, the FID responded to all the components, NPD responded to all the N constituents, and TID-1 responded to the N compounds, Indole and Carbazole, which contain a five member Pyrrole type ring structure. For analyses of Petroleum samples, its noteworthy that TID-10 and TID-1 surface ionization provides selectivity for the Pyrrole functional group, but not the Pyridine group. The TID-1 chromatogram in Figure 7 also exhibited some indication of a lower level of selective response for Indene and Fluorene. These are Hydrocarbon analogs of Indole and Carbazole which also contain a five member ring structure. Figure 8 provides a further illustration of TID-1 selectivity for Fluorene versus other Polynuclear compounds. The analysis of a Cyclo-Hydrocarbon mixture shown in Figure 9 provides further indication of TID-1 selectivity for five member ring structures with the selectivity for Dicyclopentadienne. TID-10 and TID-1 surface ion processes can contribute selective responses in either an inert Nitrogen gas environment or in an oxidizing Air or Oxygen gas environment. Consequently, a CCID chromatogram of a complex sample may also include peaks contributed by direct thermionic surface ionization processes. 5

6 Fig. 8 Fig. 9 Fig. 7 Equal Volumes, 1=cyclopentene, 2=cyclopentane, 3=cyclohexane, 4=iso-octane, 5=toluene, 6=cycloheptane, 7=cyclooctene, 8=cyclooctane, 9=dicyclopentadiene, 10=n-dodecane. 6

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