INTERIM REPORT
IDENTIFICATION AND CONTROL OF TOXIC SUBSTANCES ? IN MUNICIPAL EFFLUENTS i
.
4 Project Number 70062
July 1986
Resources Research lnslitule OF THE UNIVERSITY OF NORTH CAROLINA 1 n 1 INTERIM REPORT n TO THE NORTH CAROLINA BOARD OF SCIENCE AND TECHNOLOGY ON IDENTIFICATION AND CONTROL OF TOXIC SUBSTANCES IN MUNICIPAL EFFLUENTS
for the period 7/1/85 - 6/30/86
Principal Investigators: Dr. David H. Moreau, Water Resources Research Institute Dr. Russel 1 F. Chri stman, Department of Environmental Sciences and Engineering , UNC-Chapel Hi 11 Dr. T. Michael Harvey, Department of Environmental Sciences and Engi neeri ng , UNC-Chapel Hi 1 1 Associated Faculty: Dr. Francis A. DiGiano, Department of Environmental Sciences and Engineering, UNC-Chapel Hill Research Assistants:. Ms. Julia F, Storm, Department of Environmental Sciences and Engineering, UNC-Chapel Hill Ms. Laurie Couture, Department of Environmental Sciences and Engineering, UNC-Chapel Hi 11
The work on which this report is based was supported by funds provided by the North Carolina Board of Science and Technology and the Water Resources Research Institute of The University of North Carolina. Project Number 70062 July 1986 1 INTRODUCTION n Nature, Scope and Objectives of Research This project, initiated in July, 1985, at the request of WRRI, seeks to develop and apply a systematic procedure for pinpointing the sources of and quantifying toxins that are found in the efflu- ents from municipal wastewater treatment plants. Current methods employed by the U.S. Environmental Protection Agency and the North Carolina Division of Environmental Management to assess the toxicity of these effluents rely on bio-monitoring techniques. While these have been effective at identifying problem areas, their results have been non-specif ic with respect-to_th~Ilnambig~~s~i~t-if;ic~-~ 1 tion of the causative agents and their ultimate source. The formu- lation of effective control strategies for toxic compounds in these effluents will be greatly facilitated if the precise target com- :1 ponents and sources are known. This study has several basic objectives. First, it seeks to refine and implement a fundamental protocol for identifying specific toxic chemical substances in municipal wastewater treat- ment effluents. The compositional information this protocol can provide will allow dischargers to take appropriate corrective action and eliminate possible hazards pinpointed by the screening test. Once the toxic substances are identified, the next objective is to determine their origin. The plant influent is examined in conjunction with the effluent to ascertain whether the components of interest are entering the plant from outside sources, or are somehow produced during the wastewater treatment process. :I Additional tracking of toxic materials and precursors found in the influent sfream will be undertaken in an attempt to pinpoint the upstream source. Source identification will likely be an 11 essential step toward the elimination of toxicity problems. -. 1 SamDlina Proaram Candidate facilities for the study were selected based on the following criteria:
(1) they serve at least 50,000 persons
(2) they have been identified by the Division of II Environmental Management as having toxins in their effluents from biological monitoring evaluations
(3) they have sufficiently diverse sources of waste to provide a realistic test for the procedure. Three such facilities are currently under investigation. They rl are: High Point Eastside High Point Westsi.de Durham, Farrington Road.
2 J SPECIFIC IDENTIFICATION OF CHEMICALS AT TREATMENT PLANTS
All are biological treatment plants of various configurations. Flow diagrams of each may be found in Figures 1-3. In general the industrial use of the High Point Westside plant is predominantly that of furniture finishing and manufacturing and chemical manufacturing, while the High Point Eastsi.de industrial users are primarily textile dyeing and manufacturing. The Durham Farrington Road plant serves fewer industries than either of the High Point facilities, with Duke Hospital being the predominant contributor.
In crd-r ts mp-Hhemical -profile- -uf--eTtqjIant 1 s in- _____ fluent and effluent over time and to coordinate our analyses with the respective lab's bio-monitoring results, sampling was scheduled weekly at both High Point plants and twice monthly at Durham over a two month period. Table 1 lists sampling dates, type of sample collected, and bio-monitoring toxicity test values. Samples from both High Point plants were 24-hour composites with effluent collection prior to chlorination, identical to samples collected for toxicity testing. Durham influent samples were 24- hour composites, while effluents were grab samples collected prior to chlorination. However, Durham effluent toxicity was determined on 24-hour composites collected after chlorination with the addi- tion of a chlorine-quenching substance.
Methodolosy Continuous liquid liquid extraction (CLLE), similar to EPA method 625, and closed loop stripping analysis (CLSA) were the techniques chosen (based on research done for WRRI by Gregory Durell completed in 1985) as the best methods covering a wide compound volatility range and having sensitivities in the part- per-billion and sub-part-per-billion ranges respectively. Flow charts detailing the steps in each technique are found in Figures 4 and 5. Primary and secondary internal standards of 2'5- dimethylphenol and 1,2-dichlorobenzene respectively were added to the sample and the final extract as a means of determining recoveries. Extracts obtained by each process were subjected to capillary column gas chromatography/mass spectrometry. Mass spectra obtained were compared with the NBS library of mass spectra for identification purposes. Gas chromatography/mass spectrometry was performed by Carol Haney of the North Carolina State University GC/MS laboratory.
Results The Appendix includes data generated thus far on the continuous liquid liquid extracts. Included for each sample are tptal ion chromatograms and library search results. A sample ion chromatogram is included in Figure 6. The library search results are presently unconfirmed; we are in the process bf manually examining the data to further (and more reliably) determine the structures of the compounds. Compounds identified in the library
'3 n n Table 1. SAMPLES COLLECTED AND CORRESPONDING BIO-MONITORING RESULTS 1 Plant Samp 1ing Sample Type Bio-Monitoriyg Results 1 1c50 Lo cat ion Date Influent Effluent Influent Effluent 1 High Point, 3/03/86 Eastside 3/11/86 3/26/86
p~4/01/86 1 4/08/86 High Point, 2/03/86 X 56% Wests ide 3/03/86 X X 90% n 3/11/86 X X 15% 90% 3/26/86 X X 90% 90% 4/01/86 X 33% 90% :1 4/02/86 X X 4/08/86 X 46% 66% 4/09/8 6 X X 3 4/30/86 49% Durham. 2/03/86 X 90% Farrington Rd 2/14/86 X 1 3/10/86 X 90% 3/24/86 X
‘1L_ Except where noted otherwise all samples are 24 hour composites.
The sample dilution at which 50% mortality, determined by graphical :I extrapolation of a series of dilutions, occurred is reported. A sample dilution of 15% is 15% sample 85% dilution water. A 90% value is given when insufficient mortality occurred to calculate an LC 50 * 3 Grab sample from aeration basin. 1 3 3 3 d 1 1 5 n n 1 3 z 1 d :1
6 UNDERDRAIN RETURN re------.------,,, SOIL CONDITIONER SLUDGE DRYING BEDS ---..---
Ii r----+
v
-LEGEND - PLANT FLOW FIGURF: 3. PROCESS FLOV DIAGRAM, DURHAM FARRINGTCN ROAD PLAfT -- .+.- SLUDGE FLOW -. --c- FLOW AS SHowN PUMPS n 1 1 3
izrlx 8 c 0
8 n 1 1 9
~.:L n
3 b 3 1
&:I i d
9 h
(II
G a
F d
&.> F 3. L -i? -i? G t
-: I- -
! search are ordered according to their relative quantity in the sample based on chromatographic peak height, with the compound present in the largest quantity listed first. In general an average of approximately 30-40 compounds have been isolated from High Point influent samples and are present roughly in the range of 10-100 parts per billion (ppb). In High Point effluent samples approximately 20-30 compounds have been isolated and occur approximately in the .5-15 ppb range. Approximately 20-30 compounds have been isolated from Durham influents and are also present roughly at the 10-100 ppb level. About 10-30 compounds have been extracted from Durham effluents at roughly the 1-10 ppb level. Samples analyzed by CLSA are not reported here. Due to the extreme sensitivity of the method and the unexpectedly high concentration of the samples, dilution factors selected were not large enough. Additional development work in this area is planned. The data suggest that some compounds enter the treatment plant and are removed, while others are produced within the plant, and still others enter the plant and are not removed or altered by the treatment process. The last category is of particular interest because it represents compounds that may be of industrial origin and are present in the bio-monitoring sample. Tables 2 and 3 show chromatographic peaks common to both influent and effluent samples and their corresponding possible identities. Once positive identification of chemicals is made in the next phase of the research, more use can be made of the data.
Future Work The results presented thus far are inconclusive. However, much information remains to be extracted from the data presented in the Appendix. The following tasks will be accomplished in the next 6 months:
8 positive identification of organic compounds by manual interpretation of library search results and mass spectra,
0 cross-referencing of these compounds with toxicological data from the literature, a identification of possible origin of chemicals of interest (generated within the plant or discharged from industry),
6 search for correlation between bio-monitoring results and presence of specific organic compounds,
0 refinement of analytical techniques (CLLE extraction at various pHs, determination of proper sample dilution for CLSA) ,
11 n
Table 2. CHROMATOGRAPHIC PEAKS COMMON TO BOTH INFLUENT AND EFFLUENT SAMPLES FROM n HIGH POINT WESTSIDE PLANT (4/02/86)
1 Possible Compound Identity Based on Peak Retention Time Unconfirmed GC/MS Library Search Results Influent Effluent 9 (Lc50 = 33%) (LCSO = 90%) 7.66 7.60 *2-ethyl-l-hexanol
~~ 1 7.23 - 7.24 l-(2-methoxypropoxy)-2-propanol 6.80 6.77 *dipropyleneglycol methyl ether or 1-(2- n methoxyl-methylethoxy)-2-propanol 6.95 6.88 *dipropylenglycol methyl ether or 1-(2- n methoxy-l-methylethoxy)-2-propanol 11.55 11.55 *trichlorobenzene
4.02 3.96 *xylene
*Compounds used by industrial users of High Point Eastside and/or Westside WWTP according to survey conducted by the City of High Point Department of Water and Sewer.
Table 3. CHROMATOGRAPHIC PEAKS COMMON TO BOTH INFLUENT AND EFFLUENT SAMPLES FROM DURHAM FARRINGTON ROAD PLANT (2/14/86)
Possible Compound Identity Based on Peak Retention Time Unconfirmed GC/MS Library Search Results Influent Effluent (LC5() = 1 (Lc50 = 90%) 3.3 3.3 4-methyl-3-penten-2-oneor 3-hexen-2-one
4.1 4.2 4-hydroxy-4-methyl-2-pentanone
12 e confirmation of industrial origin by sampling at the source. Due to limited funds available for the next 6 months ($10,000) no additional data will be collected at the Durham Farrington Road plant. 1 SEAHEiING FOR SOURCES 1 Given that tests on the influent to a municipal wastewater treatment plant indicate the presence of toxic substances, the task of isolating the origin(s) of that substance is by no menas 1 a trivial task. For any municipality of any size, the sewer system feeding a treatment plant collects wastes from thousands of individual residential, commercial and industrial discharges. The system will also include hundreds of miles of underground pipe and hundreds of manholes through which toxic substances may enter by infiltration of groundwater on inflow from surface water runoff. Pinpointing the location of contaminants and specifically identifying their chemical structure nay require substantial outlays of manpower, time, and money. It is imperative that activities of this kind be undertaken in an economically efficient manner.
Three alternative strategies for undertaking that search are described and evaluated in this section of the report. One is a random process; the other two are variations on a sequential search process. The logic of these is describeu below, and, in later sections, they are applied to and evaluated for the wastewater collection system on the south side of Durham, N. C.
Search Processes
A typical dendritic drainage pattern for gravity wastewater collection systems is shown in Figure 7. Each link in the system collects wastewater from a portion of the service area, the links are connecteo at modes in the system, and trie most downstream link terminates at a wastewater treatment plant.
The problem to be solved can be stated as follows: what is the most economical strategy for locating which subarea(s) of the service area is discharging a given substance into the collection system? df course the question may be stated in a manner that requires even more precision in the answer. One may want to identify one or more individual dischargers of a particular substance. The strategy for obtaining the answer to more precise answers could be the same as that which is useu to find the subarea ( s) from which the substance oriyinates; simply define each individaul source to be a subarea. A cost-effective approach however, may be a heirarchial scheme in which the substance is first traceo to one or more subareas, and then the same or a different search procedure is used to isolate individual sources within subareas. The choice, of course, will depend upon how strongly an investigator can associate a particular substance with its likely sources. In this report, the focus is on the search procedure regardless of whether it is applied in a single pass or in a heirarchial manner.
14 n Random Search 1 The first strategy to be considered is that of random search. It is a simple process of ranking the links in the network (or, equivalently, the subareas) according to an 1 investigator's judgment about the relative likelihoods of finding the substance in each of the subareas. Samples are then taken on each link in order of descending likelihood wnile using information from each sample to eliminate upstream links from the :1 search whenever possible.
Details of the search depena upon whether measurements are qualitative or quantitative, whether there is a single or n multiple source, and whether the discharges are continuous or intermittent. A qualitative measurement simply indicates the presence or absence of a suustance (or its effect) relative to n some threshold level. For example, the bioassay for toxicity gives a positive response if any substance or combination of substances causes a given fraction of the population of a "1L specified species to die within a stated period of time. If that result does not occur, the test is negative. There is nothing about this test to indicate at what concentration a substance(s) is present even if its identity is known. If the substance is 3 unknown, its ioeritity cannot ~e determined solely on the basis of a bioassay. By contrast, measurements of both the concentration of a specific substance and the rate of flow of waste in a pipe n lead to the quantitative estimation of the mass rate of flow of the substance. 1 Differences in the information contained in these two types of measurements have significant implications for the search procedure, especially when thee is reason to suspect multiple i sources. When a source is identified using quantitative I measurements, one can estimate what portion of the mass flow at the treatment plant can be accounted for by that source. With that information, an investigator can easily decide whether or 11. not to continue the search for other sources. Qualitative measurements contain much less information: samples at more locations may be required to reach a stopping point. That does not necessarily mean qualitative neasurements are less cost I] effective; the unit costs may be less than that of quantitative measurements.
Temporal characteristics of the waste flow are imprtant in detrmining the frequency ana duration of sampling. Those are important factors in desiyning the search process, but in this 11 paper, the scope is limitea to spatial characteristics of the procedure.
. In a random search process a suDarea can be identified if measurements at the downstream end of a terminal link indicate the suustance is present. For internal links, measurements must be made at both the downstream and upstream ends of the channel. A subarea is iaentified as a source if the downstream end shows a positive response and the upstream end is negative. A negative
15 finainy at the upstream end can also be used to eliminate the need to search further upstream.
Sequential Search
An alternative to a random search is a sequential process that begins at the wastewater treatment plant and systematically proceeds upstream. There are several variations on this scheme, two or which are further examined in this study. The first is referred to as a 2-Point Test, the other a 3-Point Test. The logic of the 2-Point Test can be seen by reference to the typical section of a network shown in Figure 7. As one moves upstream in the network, from the treatment plant, Node I is encountered. Samples can be taken on either of the links coming into that node and on the outlet node. The 2-point Test uses only measurements on the inlet links, labeled locations b and c. A positive result at I-b means a source is located somewhere on tne left-hand branch, and the process moves to Node 11, and is repeated; a negative result at I-b means, of course, that the search on the left branch can be abandoned. Similar conclusions can be drawn about the right-hand branch from results at I-c. If the substance is present at the plant and botn I-b and I-c are negative, then the substance must be located in Subarea 7, (on the outlet link to Node I) and the search can be terminated. A complete decision tree for this test is shown in Figure 8; in that example the left-hand branch is always tested first.
For the 2-Point Test, then, only one test may be required before moving to the next upstream node when the search is limited to a single source. If the branch that is chosen to be sampled first shows a positive result, then one can move immediately to the next upstream node. If that result is negative, a second test is required to either terminate the search or move to the next upstream node.
The 3-Point Test uses information from point c and, if necessary, information from either b or c. A negative result at a on the outlet link would immediately imply that the source is located on that link, and the search would be terminateo. A positive result of a would tlien lead one to pick either D or c, but in this case, iy is immaterial wnich one is picked if there is a single source. If I-a is positive ana I-b is positive, one would move to II-a. A positive value at I-a and a negative at I- b implies a positive at I-C so that one would go directly to III- a without testing at I-c.
Thus, in the 2-Point Test, picking the wrong branch to sample first would carry a penalty, but in a 3-Point Test there would be no such penalty. Eowever, in the 2-Point Test, a right choice would require only one sample where the 3-Point always requires two. In other words, uncertainty does not cost anything in a 3-Point Test, but it may require more steps than the 2-Point to decide to move upstream. Offsetting some of that advantage of the %-Point Test is the fact that it always requires two tests to
16 '1 isolate a source on the outlet branch; the 3-Point only requires one test for that decision.
Some criterion is needed to guide the decision in the 2- Point Test as to which branch to sample first. A logical criterion to use is to pick that Dranch which has the highest probability of containing a source. with that criterion comes the need to assign a probability to each link that a source is locatd in, in the tributary subarea. That task is rather simple under the assumption that there is only one source in the service area. Some inefficiencies in the search process may occur if one operates under that assumption; but, of course, the truth about Matt assumption will not be known until after the search is completed.
Assigning proDaDilities under these conditions is no major task. Land use, industrial activities, and other information about individual dischargers can be usea to form opinions about the most likely sources and to make judgments about how likely or unlikely the source is located in each area. Those opinions may be expressed by a set of relative weights, say on a scale of 0 to 10 or 0 to 100. For rhe system shown in Figure 7, say an investigator believes the most likely source is Subarea 5, the next most likely is 6, the next 1, etc., and that his intensities about those rankings are reflected by the set of weights (wl, w2, W3r W4, W5, Wg, W7, ) = (25, 10, 5, 15, 45, 30, 20). The total of those weights is 150, so that the initial assignment of FroDabilities is (p, , p2, p3, P5r Pgr P7) = (25/150, 10/150r 5/150, 15/150, 45/150, 30/150,p$h/150).
When deciuing whether to go left or right at Noae I, however, the only relevant information is that pertaining to upstream areas (information about Subarea 7 has no affect on the choice of going left or right at I). The total of all upstream weights is 130 so that the conditional probability of the source beiny located on the left branch is (25 + 10 + 5)/130 = 0.31, and that on the right is (15 + 45 + 30)/130 = 0.69. In this example, one would choose to test the right-hand branch first etore the left. Of course, if the source is located on the left branch and not the right, the search process will still find that out, but the cost of the search will be increased.
Evaluation for Southside Durham
As implied by the preceding discussion, the relative efficiencies of the three tests depend upon both the geometry of a particular system and the level of uncertainty about the location of the source. Those dependencies can be seen by an evaluation of the strategies for the collection system serving the southern portion of Durham, NC, more particularly that portion served by the Yarrinyton Road Wastewater Treatment Plant. This system serves approximately 50,000 people, the Duke University complex including several hospitals, several large commercial centers, and industrial areas. It covers
17 1 ant
Figure 7. Typical Sewer System and Tributary Areas
L= 1 1=2
Left-handed 2-Point Search 1=4 L= 5
Start L=l Left-handed 3-Poi nt Search 1=2 1=3
1=4 L= 7 L= 5 L= 6
Figure 8. Gecision Trees for Sequential Searches
18 approximately 18 square miles and collects an average daily flow 1 of 9 million gallons per day. For purposes of this discussion, the service area has been divided into 14 subareas as shown in Figure 9.. A simplified 1 schematic of the system is shown in Figure 10 . The 3-Point Test is not sensitive to uncertainty; the number of tests required to isolate a source in each of the subareas is 3 shown in the first column of Table . The other two tests were evaluated using Monte Carlo Simulation. For the 2-Point Test the expected number of tests required to locate the source was estimated for each of the possible locations for each of the 5 probabilities of knowing the locations as given in Table 4 . Each estimate represents the average of 100 trials. In each trial the location was "guessed" by randomly generating a n location in a manner that the probability of correctly identifying the location is the stated probability of knowing the location and all other locations are equally likely. Probabilities used to guide the search were then calculated by assigning the stated probability to the location that was guessea and all others being equally likely. These probabilities were 1 then used to calculate conditional probabilities of locating the source on the left and right branches at each node given that it is upstream ot that node. 3 The random search was evaluated by randomly locating the "most likely" source in such a manner that the probability of ueing correct is equal to the statecj probability. Those 3 probabilities were used to generate rankings for all the locations using the principles of sampling without replacement.
1 CONC LUSIONS
Several general conclusions can be drawn from the results given in Table 4. First, as one would expect, the average number of tests required to locate the source using either the 2-Point Test on Random Search decreases as the probability of knowing the :.I location increases. Sampling errors introduce some discrepancies in that general trend. Plore important, however, is the fact that the +Point Test is superior to the 3-Point Test except in those instances where the source is located near the treatment plant. One should use the 3-Point Test for the Durham system only when there is considerable confidence that the source is so located. It is also important to note that Random Search is preferred to the 2-Point Test only when there is a very high degree of confidence that the actual location is known. Even then Ranciom Search would be preferred only if there is a strong possibility ri that the source is remote from the plant and would require passing through several nodes in a sequential search.
19 to Farrington Road 20 Wastewater Treatment Plant 1 1 1
li'I1
3
Ill I
W Wastewater Treatment P1 ant
Figure 10. Schematic of Wastewater Collection System for Southside of Durham
21 Table 4. EXPECTED NUMBER OF TESTS REQUIRED TO LOCATE SOURCE
TWO-POINT SEQUENTIAL SEARCH RANDOM SEARCH Three- Actual Point Probabilities of Knowing Location Probabi 1i ti es of Knowi ng Location Location Search 0.2 0.4 9.6 0.8 1 .o 0.2 0.4 0.6 0.8 1 .o
1 6 4.1 3.42 3.35 3.24 3 10.29 6.2 5.29 3.7 1 2 6 4.84 4.08 3.65 3.4 3 9.76 7.49 4.88 3.56 1 3 5 5.04 4.48 4.27 4.23 4 9.29 7.15 5.23 4.36 2 4 4 3.82 3.01 2.73 2.34 2 7.97 6.35 4.4 2.65 1 5 3 4 3.39 3.26 3.13 3 7.43 5.48 4.63 3.27 2 6 10 5.18 5.3 5.22 5.14 5 14.44 10.22 7.07 4.37 1 7 10 5.96 5.83 5.6 5.3 5 15.55 9.47 7.55 4.56 1 N 8 9 G.03 6.39 6.2 6.12 6 13.21 10.08 6 {-6 4.73 2 N 9 8 4.75 4.9 4.63 4.25 4 11.19 9.98 6.6 3.32 1 10 7 5 5.34 5.17 5.1 5 11.26 9.48 6.33 4.51 2 11 5 4 4.32 4.17 4.11 4 9.07 7.89 5.45 3.85 2 12 4 3 2.93 2.62 2.27 2 8.3 6.32 4.77 2.59 1 13 3 3 3.31 3.15 3.09 3 7.61 6.66 4.84 3.79 2 14 1 2 2 2 2 2 5.21 4.25 3.83 2.67 2 1
PPPEU DIX
1 n High Point Westside Effluent 2/3/86 CLLE 1 Retention Time ComDounds from Librarv Search 13 .OO 1,2,3-trichlorobenzene 1,2,4- n I 1,3,5- It 13.9 1,2,3-trichlorobenzene 1,2,4- 11 :1 1,3,5- It 24.7 2-methylquinoline l-phenyl-1H-pyrrole n 5~,l’H-cholest-2-eno[3,2-b]indol-6-one 10H-phenothiazine
19 .O 3-(2,2-dimethylbutyl)-5-hydroxyl-l,2,3-oxadiazoli~,hydroxide, :I inner salt (24,5~,17~)-17-(acetyloxy)-2-methylestran-3-one 3 2-propanesulfonic acid, methyl ester 8.93 1,2-dichlorobenzene 36.7 nonanedioic acid, dibutyl ester :-I ethanedioic acid, dibutyl ester 3-methylpentane :I 32.7 cis-5-[(aminocarbonyl)amino]-4,5-dihydro-3-phenyl-4- -isoxazolecarboxamic (0)-6,7,12b,13-tetrahydro-4H-bis[l,3]benzodioxo10[5,6-a:4‘,5’-g] quinolizine :1 1,2-naphthalenedione :I 35.4
38.6 3-bromoheptane 11 1,2-benzenedicarboxylicacid, dioctyl ester 11 , diisooctyl ester
8.42 l-(2-methoxypropoxy)-2-propanol 1 l,l’-[(l-methyl-1,2-ethanediyl)bis(oxy)]bis-2-propanol 2-methoxy-1-propanol 11 23.65 l-(l-ethoxyeth0xy)pentane bis(1,l-dimethylethy1)phosphine l-cyclopentylethanone ;i 34. a7 2-(acetyloxy)-5,8-dihydroxy-7-methoxy-l,4-naphthalenedione 2-phenylquinoline, l-oxide 4 4-decyl-1,2,3,6,7,8-hexahydropyrene 11 1 11.8 dotriacontane ll-(2,2-dimethylpropyl)heneicosane l-methyl-5-oxo-L-proline,methyl ester l-piperidinecarboxaldehyde
8.0 l-(2-methoxy-l-methylethoxy)-2-propanol 2-(2-hydroxypropoxy)-l-propanol 2-methoxybutane
35.55 (2)-3-methyl-2-hexene 3-ethyl-2-pentene 2,3-dimethyl-l-pentene
23.88 2-(l-methylheptyl)cyclopentanone 3-methylcyclohexanone 2,5-dimethyl-3-hexene
23.3 l-[2,3]bis(l,l-dimethylethyl)-2-cyclopropen-l-yl]-2,2-dimethyl-l- propanone 4-hydroxy-3-methyl-2-(2-propenyl)-2-cyclo~enten-l-one 8-methyl-8-azabicyclo(3.2.l]oct-6-en-3-one
37.7 no match found
8.13 l-(2-methoxy-l-methylethoxy)-2-propanol muco-inositol scyllo-inositol
12.37 2,5-dimethylphenol
27.97 3(la,2,7,7a-tetrahydro-2-methoxy-8-pheny1-1,2,7-metheno-lH- cyclopropa[b]naphthalen-l-y1)pyridine 3,3’-(la,2,7,7a-tetrahydro-2-methoxy-1,2,7-metheno-lH- cyclopropa[b]naphthalene-l,8-diyl)bispyridine 5,6,7,8-tetrahydro-l-naphthalenecarboxylic acid
25.3 1,4-bis(l-methylethenyl)benzene and above listed pyridines
High Point Westside Influent 3/3/86 CLLE
Retention Time ComDounds from Library Search 17.9 1,l'-biphenyl 1,2-dihydroacenaphthylene acenaphthylene biphenylene
13.0 naphthalene azulene bicyclo[4.4.l]undeca-l,3,5,7,9-pentaen-1l-one
5.7 2-butoxyethanol ethanedioic acid, dibutyl ester bis(1,l-dimethylethy1)diazene
9.0 2-ethyl-l-hexanol 4-butyl-1,3-cyclopentanedione (Z)-2-hexene
9.1 benzenemethanol phenylsulfinylhydrazine ethenylmethylenecyclopropane
32.3 (z,z)-9,12-octadecadienoic acid 1- hep tadecanol 9,12-octadecadienal
15.9 benzeneacetonitrile l-azido-3-bromobenzene l-azido-2-bromobenzene 1H-indole
38.1 5-methyl-2-undecene 5-ethyl-2-methylheptane (ethenyloxy) isooctane
45.23 14-methylcholestane (5.~)-14-methylcholestane
7.8 N,N-dimethylcyclohexanamine N-ethylcyclohexanamine trans, 2-methyl-3-(l-methylethyl)aziridine
41.6 4,8,12-trimethyl-3,7,11-tridecatrienenitrile (Z,E)-3,7,11-trimethyl-2,6,lO-dodecatrien-l-o1 1-methyl-4-(1,5,9-trimethyl-1,5,9-decatrienyl)cyc1ohexene
46.2 1,2-octadecanediol l-pentadecene 1,1,3-trimethyl-2-(3-methylpentyl)cyclohexane II
47.6 1-hexacosanol 1 nonadecanol 1-eicosanol 1 54.6 1,2-octadecanediol l,l’-dodecylidenebis[4-methyl]cyclohexane 4,8,12-trimethyl-3,7,ll-tridecatrienoicacid, methyl ester [I 12.9 1,2,3-trichlorobenzene 1,3,5- W 1,2,4- It
:1 10.3 3-methylphenol 4-methylphenol :1 1,3-cyclohexadiene 10.4 l-methyl-3-(l-methylethyl)benzene l-methy-2- 11 :‘I 1- It -4- It 10.8 undecane 2,7-dimethylundecane J 2,4,6-trimethyldecane 18.8 I._. 11.2 1,2,3,4-tetramethylbenzene ._ 1,2,3,5- 11 ‘1 l-methyl-3-(l-methylethyl)benzene
11.4 same as RT 11.2 ‘-1C.. 13.3 2-methyl-5-(l-methylethyl)bicyclo[3.l.O]hexan-2-01 1,7,7-trimethyl-tricycl0[2.2.1.02,6]heptane l-methyl-3-(l-methylethenyl)cyclohexene ‘IL- (S)-N,~,4-trimethyl-3-cyclohexene-1-methanol
36.0 hexanedioic acid, dioctyl ester 11 -1L.. , bis(2-ethylhexyl) ester tetraco sane
50.7 1-hexacos ano 1 -1 1-heptacosanol 1-tetracosanol 11 24.0 isocyanobenzene quinoxaline (Z)-benzaldehyde, oxime ,
23.4 N,2-dimethyl-N-nitro-l-propanamine tetramethyloxirane 3-ethylcyclobutanol, acetate n 20.7 l-phenylcyclohexanecarboxylic acid, methyl ester 3,4-dihydro-2(1H)-naphthalenone bis(1-methylethy1)phosphine
20.9 2-(dimethylamino)-l-phenyl-5-nonanone N-methyl-N-(trifluoroacetyl)glycine, l-methylpentyl ester 3-(dimethylamino)propanenitrile
24.6 heptadecane nonacosane heptacosane
26.5 hencicosane 6-methyltridecane 3-ethyl-5-(2-ethylbutyl)octadecane
27.3 3,3-dimethylcyclobutene l-ethylcyclopentene 4-methylcyclopentene 3,7-dihydro-1,3,7-trimethyl-lH-purine-2,6-dione
18.5 2,6-dimethylnaphthalene 1,2- 11 2,5-cyclohexadien-l-yl-benzene
11.9 (2-methyl-l-propeny1)benzene 2,3-dihydro-4-methyl-lH-indene W - 5- 11
12.0 l-phenylcyclohexanecarboxylic acid, methyl ester 1,4-dihydro-l-methyl-3-pyridinecarbonitrile (1,l-dimethylbuty1)benzene l-(2-methoxypropoxy)-2-propanol
12.1 (2-methyl-l-propeny1)benzene 2,3-dihydro-4-methyl-lH-indene " -5- 11
12.2 2-ethyl-1,3-dimethylbenzene (4-methylpheny1)phenylethanedione (1,l-dimethylethy1)benzene
13.4 1-(4-ethylphenyl)ethanone ethyl-1,2,4-trimethylbenzene 3-(2,5-dimethylbenzoyl)butyric acid, methyl ester 13.5 do decane 6-methyltridecane heneicosane
13.8 1,2,3-trichlorobenzene 1,3,5- 11 16.2 2-methylnaphthalene 1,4-dihydro-1,4-methanonaphthalene l-methylnaphthalene 10.2 l-ethyl-3,s-dimethylbenzene (1,1,2-trimethylpropyl)benzene (1,l-dimethylbuty1)benzene
10.9 1,2,3,4-tetramethylbenzene l-ethyl-3,5-dimethylbenzene 1,2,3,5-tetramethylbenzene
13.9 nonaco s ane hep tacosane 3,4-dimethyldecane 17.1 (S)-3-(l-methyl-2-pyrrolidinyl)pyridine 2-methylene-4-pentenenitrile 3-vinyl-1,4-pentadiene
4.2 l-(2-propenyloxy)-2-propanol 6,10,14-trimethyl-Z-pentadecanone 3-ethoxy-l-propanol
4.4 azidocyclohexane 9,12-octadecadienal 4-methylhexanal
4.7 1,2-dimethylbenzene 1,4- 11 1,3- 11
5.1 2-cyclohexen-1-01 2,4-hexadien-l-ol 5-methoxy-4-methyl-l-heptene
5.2 1,3-dime thylbenzene 1,2- 11 1,4- 11
6.2 2-cyclohexen-l-one
6.1 2-methyl-2,4-pentanediol 2-(2-hydroxypropoxy)-l-propanol 1,2-butanediol
6.7 [(phenylmethoxy)imino]acetic acid, trimethylsilyl ester [(methylsulfinyl)methyl]benzene 1,1,2-trichloropropane l-chloro-2-methylbenzene
7.2 dimethyltrisulfide 3,8-dimethyl-s-triazolo[4,3-a]pyridine
7.7 - phenol carbamic acid, phenyl ester butylmethylcarbamic acid, phenyl ester n
8.0 hep t aco sane n decane pentacosane 1 8.6 1-(2-methoxypropoxy) -2-propanol 2-hydroxybutanoic acid, ethyl ester 3 2 -methoxy - 1 - prop ano 1 9.5 l-methyl-3-propylbenzene n -2- It (l-methylpropy1)benzene
9.7 1,2,3,4-tetramethylbenzene l-methyl-2-(l-methylethyl)benzene -3- It
30.6 molecular sulfur
31.8 2-ethyl-N,n-dimethyl-l-hexanamine 2-methylundecanal 2-methylhexadecanal
32.4 cis-2-(2-methylpropyl)-l,l’-bicyclohexyl 4-cyclohexyldodecane 4-cyclohexyl 2-butyl-l,l’-bicyclohexyl
33.6 l-(1,6-dioxooctadecyl)pyrrolidine bis(1,l-dimethylpropy1)diaziridinone 7-butyldocosane
34.1
35.8 octadecanoic acid, butyl ester l-hexacosonol l-heptacosanol
50.0 54.0 e- e-
1I
c .I
'-'1 .. I
m3 .;-1 I_J
/' 3
3 V " I /I High Point Westside Effluent 3/3/86 CLLE
Retention Time ComDounds from Library Search
7.4 N,N-dimethylcyclohexanamine N,-ethylcyclohexanamine l-aminocyclopentanecarboxylic acid
12.9 1,2,3-trichlorobenzene 1,2,4-trichlorobenzene 1,3,5-trichlorobenzene 13.8 1,2,3-trichlorobenzene 1,2,4- 11 1,3,5- If 2,2-dimethyl-2H-l-benzopyran 9.0 1,2-dichlorobenzene
4.3 3-methyl-7-oxabicyclo[4.l.O]heptane 6-nitro-l-hexene bicyclo[7.1.0]decane 18.7 3,6-octadecadiynoic acid, methyl ester 9-octadecen-12-ynoicacid, methyl ester 2-iodohexane 6.1 2-cyclohexen-l-one 20.7 1H-indole-3-aceticacid, methyl ester l-(1,l-dimethylallyl)-L-tryptophan 1H-indole-3-aceticacid, hydrazide 23.3 3-methoxy-quinoline
18.3 (3-cyclopentylpropyl)cyclohexane 7-nonynoic acid, methyl ester 1,ll-dodecadiene 23.6 2-piperidineacetic acid,& -phenyl-, methyl ester, hydrochloride 2,5-dimethyl-2-hexene 4-penten-2-one,3-methyl, O-methyloxime
5.05 3-methyl-7-oxabicyclo[4.l.O]heptane 6-nitro-l-hexene bicyclo[7.1.0]decane
16.7 -bicyclo[2.2.l]hept-5-en-2-yl-l-piperidinepropanol (l-methylpropy1)-cyclohexane octahydro-1,5-dinitroso-l,5-diazocine 22.5 1,2-benzenedicarboxylic acid, diethyl ester 1 1,2-benzenedicarboxylic acid, dibutyl ester 1,2-benzenedicarboxylic acid, dipropyl ester 1 9.8 l-methyl-1H-pyrrole l-chloro-2-nitrosocyclohexane cis-1,3-dichlorocyclohexane 26.7 no match found
36.2 2-ethyl-5-propylthiophene ” 2,3,4,4-tetramethyl-2-cyclopentene-l-thione (methoxymethoxy)-cyclooctane 38.1 3- (bromomethyl)heptane 1,2-benzenedicarboxylicacid, dipentyl ester 1,2-benzenedicarboxylic acid, dioctyl ester 37.2 no match
8.9 (Z)-l-(l-buteny1oxy)heptane (E)-l-(l-buteny1oxy)heptane 2-ethyl-N-(2-ethylbutyl)-l-butanamine 8.4
24.0 3a, 7-methano-3aH-cyclopentacyclooctene,l,4,5,6,7l8,9,9a-octahydro- 1,1,7-trimethyl-,[3aR-(3a.a(, 7a1 gap)]- 5-heptenylbenzene
30.0 5-(l-methylethylidene)-l,3-cyclopentadiene 4-hydroxy-2-methoxybenzonitrile 3-methyl-5-propylpyridine 32.3 N,N-dimethyl-3-phenylalanine, ethyl ester 2-acetyl-2,8-dihydro-7-methyl-8-methylenepyrazolo[5,l-c] [1,2,4]triazine 2,4-dimethylpentanal 7.9 1,2,4-trimethylbenzene 1,3,5-trimethylbenzene 1,2,3-trimethylbenzene 12.2 2,5-dimethylphenol 16.0 3,4-dimethylsyolnone cyanic acid, sec-butyl ester n 17.4 l-propanol, 2,3-dimethyl-, 4-nitrobenzoate 11.7 3-[(l-methylethyl)amino]propanenitrile trans-2,3-bis(l-methylethyl)oxirane 1 2,3,4-trimethyloxetane 40.5 1,2-benzenedicarboxylic acid, dibutyl ester 1 - prop oxypentane D sulfurous acid, bis(1-methylethyl) ester 5.9
8.0 -D-xylofuranoside, methyl 4-methyl-3-hexanol ‘1‘^
3 3 -1._
‘1&- :I
I 3 I
'I :1 High Point Westside Influent 3/11/86 CLLE
Retention Time Compounds from Librarv Search
8.52 l-(2-methoxypropoxy)-2-propanol l,l'-[l-methyl-1,2-ethanediyl)bis(oxy)]bis-2-propanol 2-methoxy-1-propanol 3 3-methoxy-1-butanol 17.75 benzoic acid, butyl ester benzoyl chloride :1 4-oxobenzenebutanoic acid
8.02 decane :.I 6-methyl-octadecane 1-iodooctane
8.18 l-(2-methoxy-l-methylethoxy)-2-propanol :1 2-(2-hydroxypropoxy)-l-propanol 3-methoxypentane II 12.85 1,2,3-trichlorobenzene 1,2,4- 11 1,3,5- 11 3 l-bromo-3,5-dichlorobenzene 19.58 1,2-benzenedicarboxylic acid, dimethyl ester terephthalic acid, methyl vinyl ester 1,3-benzenedicarboxylicacid, dimethyl ester 38.17 1-iodooctane 5-ethyl-2-methylheptane 1,2-benzenedicarboxylicacid, dibutyl ester 17.a7 1,l' -biphenyl 1,2-dihydroacenaphthylene 3 biphenylene 24. a7 benzoic acid, pentyl ester :.I 3-methyl-1-butanolbenzoate 2-cyano-2-hydroxyhexanoicacid benzoate, ethyl ester 10.80 nonacosane II octacosane undecane ;1 13.02 naphthalene azulene bicyclo[4.4.l]undeca-l,3,5,7,9-pentaen-1l-one
3 8.88 trans-1-ethyl-3-methylcyclopentane 7-ethyl-2-methyl-4-undecanol d 2-ethyl-1-hexanol 1
13.28 4,d,-4-trimethyl-3-cyclohexene-l-methanolacetate n 1,7,7-trimethyltricyclo[2.2.1.02,6]heptane 2,6-dimethyl-2,4,6-octatriene
1 24.02 l-methyl-4(1H)-quinazoline (2)-benzaldehyde,oxime pyrido[2,3-d]pyridazine
1 54.90 octahydro-l-(2-octyldecyl)-pentalene l-hexacosanol :i (Z) -9,17-octadecadienal 45.33 2-(acetyloxy)-l-[(acetyloxy)methyl]ethyl ester of (z)-9-octadecenoic acid l-Dotriacontanol :1 octahydro-l-(2-octyldecyl)pentalene 14-methylcholestane 5 ,14-methylcholestane 4a,sa,4,~-epoxycholestane 4.65 1,2-dimethylbenzene 1,4- It 3 1.3- It 5.48 2-butoxyethanol ethanedioic acid, dibutyl ester 3 2,2,4,10,12,12-hexamethyl-7-(3,5,5-trime:hylhexyl) tr ic ecane 47.77 l-Dotriacontanol l-hexacosanol 3 17-pentatriacontene 15.83 2-methylnaphthalene 3- 1- I? methylbutanedioic acid, bis(1-methylpropyl) ester
'1I.. 13.2 S-(l-methylethyl) ester of propanethioic acid 6.65 [(methylsulfinyl)methyl]benzene l-chloro-2-methylbenzene 3-chloro-1,3,5-cyclohepatriene
41.73 (Z,E)-4,8,12-trimethyl-3,7,ll-tridecatrienoi.cacid, methyl ester 4,8,12-trimethyl-3,7,11-tridecatrienenitrile 2,3,6-trimethyl-1,5-heptadiene 50.92 l-dotriacontanol nonacosanol 1- hep tacosanol 18.8 lf5-dimethylnaphthalene 1,2- 11 1,7- 11 I 20.7 1H-indole-3-aceticacid, methyl ester 1 2-methyl-3-oxo-1-indazolinecarboxylicacid, ethyl ester .. 1,2-bis(l-methylethyl)benzene 16.23 2-methylnaphthalene 1 1-methylnaphthalene 1,4-dihydro-1,4-methanonaphthalene 27.38 3,7-dihydro-1,3,7-trimethyl-lH-purine-2,6-dione 3 1-pentylcyclopentene 1-cycloocten-1-yldiethylborane
13.78 1,2,3-trichlorobenzene n 11 1,2,4- 1,3,5- 11 1 5.95 :1 23.45 isobutyl isopropyl sulfide 2,5-dimethoxy-2,5-dimethylhexane 3 2-decanol, propanoate 7.85 carbamic acid, phenyl ester (octy1oxy)benzene 1 7-methyl-4-octano1,acetate 3 20.8
5.35 nonane 3 4-ethylheptane 2,4-dimethylhexane 31.72 17-pentatriacontene 3 1,4-didecylcyclohexane 9,12-octadecadienal 35.48 1-phenanthrenecarboxylic acid, 1;2,3,4,4a,9,10,10a-octahydro-l, :1 4a-dimethyl-7-(l-methylethyl), methyl ester, [lR-(l.a,4zy&lOa&)] 6-bromo-3,4-dihydro-3-(phenylmethyl)-2H-l,3-benzoxazine 1 5-(phenylmethyl)-2-thioxo-4-imidazolidinone 4.47 ethylbenzene 2-methyl-4,6-octadiyn-3-one (phenylmethy1)phosphonous dichloride 1 also; dimethylbenzene isomers 35,33 pentatriacontane octadecanoic acid, butyl ester octacosane 4 LI 1 n 1 11.73 cis-d,~,4,5-tetramethyl-1-cyclopentene-1-methano1 trans, 11 3-propyl-3-hepten-2-one
1 9.80 undecane 2 -bromooctane ll-(l-ethylpropy1)heneicosane
3 26.8 l-chloro-2-methylazetidine 3,3-diethylpentane 2,2-dimethylpropanamide n 32.3 4-cyclohexyldodecane, 4-cyclohexyl- 3-cyclohexyltridecane, 3-cyclohexyl- :1 3-cyclohexyldodecane, 3-cyclohexyl- 11.0 tX,a-dimethylbenzeneethanamine 2,2'-oxybis[N,N-dimethylethanamine N,a-dimethylbenzeneethanamine '1L 35.9 hexanedioic acid, bis(2-ethylhexyl) ester (E)-l-(l-ethoxyethoxy)-2-hexene 3 1,l-dimethylcyclopentane 13.4 isothiocyanatobenzene fX-methyl-0c-vinyl-2-furanacetaldehyde 3 l-methyl-4-(l-methylethyl)-l,3-cyclohexadiene
13.45 do decane 5,7-dimethylundecane 2,6,6-trimethyldecane I 1 -1 P1 3 :1
:I I
:I - 1 V
*It. J
VI L'1 i
I d 1 1 High Point Westside Effluent 3/11/86 CUE
Retention Time ComDounds from Library Search 19.62 1,2-benzenedicarboxylicacid, dimethyl ester terephthalic acid, methyl vinyl ester e thynylbenzene
36.33 nonanedioic acid, dibutyl ester 2-ethyl-5-isopentylthiophene l-(ethenyloxy)-2-methylpropane
12.83 1,2,3-trichlorobenzene 1,2,4- If 1,3,5- 11
8.43 l-(2-methoxypropoxy)-2-propanol 2-methoxy-l-propanol 2-methoxybutane
8.93 1,2-dichlorobenzene 34.53 thiocyanic acid, phenyl ester 2-(4-methylphenoxy)benzoic acid benzenethiol 38.20 1,2-benzenedicarboxylicacid, dipentyl ester II , diisooctyl ester
14.70 hexahydro-2H-azepin-2-one 4-amino-2(1H)-pyrinidinethione 2 - oxepanone
24.02 l-(2-hydroxy-5-methylphenyl)-2-hexen-l-one It -4-methyl-2-penten-l-one l-methyl-4(1H)-quinazolinone
23.42 3-O-methyl-D-fructose 2-methyl-2-(l-methylethyl)-l,3-dioxolane (la-~,lb-~,5a-~,60c,6a.IY)-hexahydro-5a,6-dihydroxy-la-methyl- oxiremo[4,5]cyclopenta[l,2-c]pyran-2(laH)-one
8.03 l-(2-methoxy-l-methylethoxy)-2-propanol 2-(2-hydroxypropoxy)-l-propanol 2-methoxybutane
43.00 1,2-benzendicarboxylic acid, dipentyl ester I1 , dicyclohexyl ester
13.78 1,2,3-trichlorobenzene 1,3,5- II 1,2,4- I1 1
30.05 d-(acety1amino)benzeneacetic acid, methyl ester n 6-methylpyrido[3,2-d]pyrimidine-2,4(1H,3H)-dione 1,4-dihydro-2,3-quinoxalinedione 1 1,2-dihydro-3H-indazol-3-one 40.62 no library match 3 32.40 4- ace ty lb enzoni tr ile nitrobenzene quinoline 6.83 phenyl carbamic acid, methyl ester isocyanatobenz ene benzeneacetaldehyde 1H-benzotriazole 33.97 5 -cyclohexyl decane 1,l’-oxybiscyclohexane octadecanoic acid
8.13 l-(2-methoxy-l-methylethoxy)-2-propanol cis-inositol my0 - inos ito1 26.80 3-phenyl-2-propen-1-01propanoate 4-acetylmorpholine thiocyanic acid, butyl ester 2-pentanone, thiosemicarbazone 23.63 2,5-dimethyl-2-hexene l,l-dichloro-2-(1,2-dimerhylbutylbutyl)cyclopropane 3-methylcyclohexanone 45.33 no library match 20.03 1,6-heptadiyne [(methylsulfinyl)methyl]benzene (phenylmethy1)phosphonous dichloride 35.02 5 -methoxybenzo furan N-methyl-N-pheny1formami.de 27.38 20.70 3-cyanobenzoic acid 3,3’-[dithiobis(methylene)]bis-lH-indole 18.78 monacosanol 6-ethyl-3-hydroxy-3,7-dimethyl-4-octenoicacid, methyl ester l-heptadecanol, acetate 24.43 10H-pheno thiazine 4-phenyl-2(1H)-pyridinone 1 18.37 4-pentylphenol 45.2 no library match
1 16.57 4-(l-methylethyl)benzoic acid, methyl ester
12.23 2,5-dimethylphenol u H I-
i
b 0
.-. .-.. High Point Westside Influent 3/26/86 CLLE
Retention Time Compounds from Librarv Search
6.07 N,N-dimethylcyclohexanamine N-Ethylcyclohexanamine 23.59 Benzoic acid, pentyl ester Benzoic acid, phenyl ester 3.47 1,4-Dimethylbenzene 1,2-Dimethylbenzene 1,3-Dimethylbenzene 3.32 Ethylbenzene 1,2-Dimethylbenzene 1,3-Dimethylbenzene 2.18 Methylbenzene 3.97 1,4-Dimethylbenzene 1,2-Dimethylbenzene 1,3-Dimethylbenzene 7.58 2-Ethyl-1-hexanol 12.01 oS-Terpineol Linalyl propionate
7.15 l-(2-Methoxypropoxy)-2-propanol 3-Methoxy-2-butanol 4.25 2-Butoxyethanol 7.68 Benzenemethanol 3-Methylphenol 16.58 1,l’-biphenyl 7.47 D-limonene Bornylene 11.65 Naphthalene
5.32 1-Chloro-2-Methylbenzene 1-Chloro-3-Methylbenzene
6.72 l-(l-Methoxy-l-methylethoxy)-2-propanol Dipropyleneglycol methyl ether 11.51 1,3,5-Trichlorobenzene 1,2,4-Trichlorobenzene 1,2,3-Trichlorobenzene
36.86 3-Nitro-1,2-benzenedicarboxylic acid 1,2-Benzenedicarboxylic acid, bis(2-ethylhexyl) ester 1,2-Benzenedicarboxylic acid, diisooctyl ester 34.68 Octadecanoic acid, butyl ester 36.21 Tritetracontane Tetratetracontane Heneicosane 6.86 Dipropyleneglycol methyl ether l-(2-methoxy-l-mehtylethoxy)-2-propanol 5.61 l-Ethyl-2-mehtylbenzene l-Ethyl-3-methylbenzene l-Ethyl-4-mehtylbenzene 6.47 1,2,3-Trimethylbenzene 1,3,5-Trimethylbenzene 1,2,4-Trimethylbenzene 9.04 4-Methylphenol 9.54 Undecane 2-Methyldecane
13.65 Hexahydro-2H-azepin-2-one Octahydroazocine 14.87 2-Methylquinoline l-Methylisoquinoline 20.83 Dodecanoic acid Decanoic acid 24.69 Decanoic acid Dodecanoic acid 26.02 Caffeine 28.31 Undecanoic acid Dodecanoic acid Tridecanoic acid 30.20 Tetradecanol-018 1-Hexadecene 31.17 No library match 31.70 N,N8-di-2-propenylurea Trans-2,3-bis(l-methylethyl)oxirane
31.92 Doc0 sane Tr ic o sane Octacosane
33.42 E icos ane Octacosane 9-Octylheptadecane
34.86 2,6,10,15-Tetramethylheptadecane Heptacosane Hexatriacontane '1'. 40.04 Nonadecane Hexatriacontane
43.44 Desace tylcinobufagin ,I Dihydrocholesterol
48.83 3-oxo-D:A-friedooleanan-28-al (kA), '1I. l-Naphthalenepropano1,cx -ethenyldecahydro-5-(hydropha 4+, 5a,8a.a] 10,13-eicosadienoic acid, methyl ester 3 44.01 Heptadecene-(8)-carbonic acid-(1) (z)-, II 9-Octadecenoic acid ethyl ester
3 T- I 7 1555 I -I
I L I I I I I I 1 I I I I
I i I 1 High Point Westside Effluent 3/26/86 CLLE
Retention Time ComDounds from Librarv Search
7.43 N,N-dimethyleyclohexanamine N-ethylcyclohexanamine S-(cyclohexylmethyl)-2-pyrrolidinone
8.72 l-(2-methoxypropoxy)-2-propanol l,l’-[(l-methyl-1,2-ethanediyl)bis(oxy)]bis-2-propanol 3-methoxy-l-butanol
8.22 l-(2-methoxy-l-methylethoxy)-2-propanol 2-(2-hydroxypropoxy)-l-propanol cis-inositol 8.32 Sames as 8.22 except allo-inositol
8.97 l,l’-[(l-methyl-1,2-ethanediyl)bis(oxy)]bis-2-propanol 2 - (2 -hydroxypropoxy)- 1-propanol 2-methoxy-l-propanol
16.58 (3-methy1penty)cyclohexane 2-(l-methylethylidene)cyclohexanone 13.02 1,2,3-trichlorobenzene 1,2,4-trichlorobenzene 1,3,5-trichlorobenzene 9.03 1,2-dichlorobenzene
15.03 Hexahydro-2H-azepin-2-one trans,l,2-diethylcyclobutane 6-nitro-2-hexene 23.73 1,2,3- trime thoxypropane 1,3,4,5-tetra-O-methyl-D-galactitol,diacetate 36.77 Nonanedioic acid, dibutyl ester N-heptyl-N-nitroso-l-heptanamine ~-ethyl-8-methoxy-a,~-dimethyl-2-naphthalenepropanoicacid, methyl ester 19.07 2-[(1-butyl-2-propynyl)oxy]tetrahydro-2H-pyran 3,6-0ctadecadiynoic acid, methyl ester Palmitaldehyde, diisopentyl acetal 16.12 2-propyl-1,3-cyclohexanedione 1,4-dimethyl-2-(2-methylpropyl)-cyclohexane, (la, 2p,Sa) Diethylcyclohexane 5.67 No match 38.63 3,6-0ctadecadiynoic acid, methyl ester 2-(l,l-dimethylethyl)phenol 1,2-benzenedicarboxylic acid, dipropyl ester
27.13 Bis(1,l-dimethylethy1)peroxide 2-Methyl-3,5-pyridinedicarbonitrile 2,Z-dimethyloxetane 9.20 N-N-dimethylbenzenemethanmine N-nitroso-N-(phenylmethy1)benzenemethanamine Cycloheptatrienylium, iodide
11.07 N-N-dimethyl-1,3-propanediamine 0-methyloxime of cyclopentanone 1-Butylcyclobutanol 1,4-dihydro-3,6-dimethyl-l,2,4,5-tetrazine
12.43 2,5-dimethylphenol 2,4-dimethylphenol 2,3-dimethylphenol
5.17 1-methyl-1-phenylhydrazine 0-(phenylmethy1)hydroxylamine 1,1’-(1,3-propanediyl)bisbenzene 34.92 1-phenylisoquinoline, 2-oxide 7H-indeno[2,1-a]anthracen-7-one 2-(acetyloxy)-5,8-dihydroxy-7-methoxy-l,4-naphth 1 nedi ne ’
37.37 1-phenylcyclohexanecarboxylic acid, methyl ester l-(l-adamentyl)-3-(l-methylcyclopentyl)-2-aziridinone
13.97 1,2,3-trichlorobenzene 1,3,5-trichlorobenzene 1,2,4-trichlorobenzene 27.83 2-neopentylpyridine 2-methyl-1-phenylazetidine 2-phenylazetidine
16.28 2-ethyl-N-(2-ethylbutyl)-l-butanamine N,N-dipropyl-1-propanamhe 4-methyl-N-(4-methylpentyl)-l-pentanamine
16.95
34.43 N,N’-dihexyl-1,3-propanediamine 5-oxoproline, 2,4,5-trichlorphenylester
36.35 Octadecanoic acid, butyl ester Docosanoic acid 17-Pentatriacontene 1
13.43 ~,~,4-Trimethyl-3-cyclohexene-l-methanol,acetate n (O)-l-methyl-3-(l-methylethenyl)cyclohexene 2,6-dimethyl-2,4,6-octatriene 1 .- . - ,..- :1 1 1 3 n :1
'_'I 3 1 I] :1
'1L. :1 1 1 3 d 1 4ib a -2 - -3F
-5:c * High Point Westside Influent 4/02/86 CLLE
Retention Time Compounds from Library Search 7.66 2-ethyl-l-hexanol 9.02 4-methylphenol 3-methylphenol
7.23 l-(2-methoxypropoxy)-2-propanol 34.14 1,2-benzenedicarboxylicacid, butyl phenylmethyl ester 2.20 Toluene 22.72 4-Methylquinazoline, 3-oxide 7.73 Benzenemethanol 11.69 Naphthalene
12.01 1- c(- terp ineo 1 a-t erp ineo 1 6.80 l-(2-methoxy-l-methylethoxy)-2-propanol dipropyleneglycol methyl ether 14.62 1H- indole 6.95 l-(2-methoxy-l-methylethoxy)-2-propanol Dipropyleneglycol methyl ether
20.86 Dodecanoic acid 6.48 Pheno 1
16.72 Decanoic acid 24.72 tetradecanoic acid 23.61 Diphenylethanedione 19.44 4-Methyl-5-phenyl-4-imadazolin-2-one 11.55 1,3,5-Trichlorobenzene 1,2,3-Trichlorobenzene 1,2,4-Trichlorobenzene 3.52 1,3-Dimethylbenzene 17.62 N-(4-Hydroxyphenyl)acetamide 9.12 Benzenemethanethiol 1,2,4-Trithiolane
16.62 1,l’-Biphenyl 14.55 l-Methylnaphthalene 2-Methylnaphthalene
21.86
29.14 Molecular sulfur
14.94 l-Methylnaphthalene 2-Methylnaphthalene
2.73 6-Methyl-2-phenylindole
3.38 Ethylbenzene 1,3-Dimethylbenzene
4.02 1,2-Dimethylbenzene 1,3-Dimethylbenzene 1,4-Dimethylbenzene
19.51 1,2,4,6-Tetrathiepane 1,2,4-Trithiolane n
n :1 :1
G &I-
1
5 E Tp 0 0- mLD I 41 0 rl d w- 3t
-A , , , . , . . . , , , . , , , , , , . . . , *, , , , . . , .-. , , , , , .,, - e’ a 0 c3 0 0 4z 0 0 0 0 AO 0 c3 0 0 m N High Point Westside Effluent 4/02/86 CLLE
Retention Time ComDounds from Librarv Search 7.24 l-(2-methoxypropoxy)-2-propanol 22.68 7.60 2-ethyl-l-hexanol 6.77 Dipropyleneglycol methyl ether l-(2-methoxy-l-methylethoxy)-2-propanol
19.37 Thiocyanic acid, 1H-indol-3-ylester 2-isopropylidenedihydrobenzofuran-3-one
7.52 1,2-Dichlorobenzene 6.88 Dipropyleneglycol methyl ether 11.45 1,2,4-trichlorobenzene 1,3,5-trichlorobenzene
25.97 Caffeine 31.03 2,2,5,7-Tetramethyl-l-tetralol 3.96 o,m, or p-xylene Ethylbenzene
10.95 2,5-Dimethylphenol 2.46 Hexanal 7.81 N,N-Dimethylbenzenemethanmine 12.38 1,2,3-Trichlorobenzene 1,3,5-Trichlorobenzene 1,2,4-Trichlorobenzene
35.03 6.13 N-ethylcyclohexanamine N,N-Dimethylcyclohexanaine
14.8 Nonamide 3-Heptanone
33.6 6-Mercapto-2-phenyl-4(lH)-pyrimidinone 3,4-Benzo-6,7-dihydro-6,7-dimethyl(lH)azepine-2,5-dione
36.78 1,2-benzenedicarboxylic acid, dioctyl ester 5.31 1-Chloro-2-methylbenzene 1-chloro-3-methylbenzene 1 1-chloro-4-methylbenzene 8.42 17.08 .- -A LL I .I:'..? ,_.: .cf .I. TIC
n n 1 3 n
1-l L 1
L1 e- _,.2 , 3 3 I
3 ;] ;] L.. li ,, '?"? ri u H I- I- n .-
:1 High Point Westside Aeration Basin 4/30/86 CLLE 1 Retention Time ComDounds from Library Search 9.02 4-Methylphenol 14.63 1H-Indole 1 Benzeneacetonitrile
16.85 3-Methyl-1H-indole :1 1H-indole-3-ethanamine 2-Methyl-1H-indole
28.35 Hexadecanoic acid :'1 Tetradecanoic acid '1.. 31.18 No library match 7.63 2-Ethyl-l-hexanol 3 6.45 Phenol 11.53 1,2,3-Trichlorobenzene 1,2,4-Trichlorobenzene :[I 1,3,5-Trichlorobenzene 5.81 Dimethyltrisulfide :I 7.24 l-(2-Methoxypropoxy)-2-propanol 3-Methoxy-2-butanol
7*< 11.99 Linalyl propionate 1- o(- terp ineo 1 1 17.13 1,l' -0xybisbenzene 22.71 3 11.67 Naphthalene 24.71 Tetradecanoic acid 3 18.92 1,3-Dihydro-2H-indol-Z-one 2,3-Dihydro-4-methyl-lH-indole 14.53 l-Methylnaphthalene 1 2-Methylnaphthalene
14.92 l-Methylnaphthalene 3 2 -Methylnaphthalene d 3 11 36. a7 3-Nitro-1,2-benzenedicarboxylic acid 1,2-Benzenedicarboxylic acid, diisooctyl ester 1,2-Benzenedicarboxylic acid, bis(2-ethylhexyl) ester 1 6.81 Dipropyleneglycol methyl ether l-(2-Methoxy-l-methylethoxy)-2-propanol 17.49 1,8-Dimethylnaphthalene 3 1,7-Dimethylnaphthalene 1,4-Dimethylnaphthalene
6.92 l-(2-Methoxy-l-methylethoxy)-2-propanol n Dipropyleneglycol methyl ether n 40.41 12.13 Isothiocyanatobenzene Thiocyanic acid, phenyl esster n 12.45 1,2,4-Trichlorobenzene 1,3,5-Trichlorobenzene :1 1,2,3-Trichlorobenzene 43. a4 Globulol 1,2-Dimethyl-3,5-bis(l-methylethenyl)cyclohexane n 10.70 2-Ethylhexanoic acid 25.82 (z)-9-0ctadecenoic acid :1 Tetradecanoic acid 23.53 Octyl phenol isomer 1 4-(2,2,3,3-Tetramethylbutyl)phenol 16.60 1,l'-Biphenyl II 17.56 1,8-DTmethylnaphthalene 1,4-Dimethylnaphthalene 1,3-Dimethylnaphthalene 3 2,3-Dimethylnaphthalene I1 11 1 :1 1 :1 1 :I 11 :I 1 :I 11 :1 :I II 11 * Ij 5 Ll 1 1 n'
1. 2 I <.:I 3
1. 3. I, 5 :3
1 ~1 c n 1 High Point Eastside Effluent 3/03/86 CLLE 1 Retention Time ComDounds from Library Search 7.61 1,2-Dichlorobenzene 10.29 Phosphoric acid, triethyl ester 11.54 1,3,5-Trichlorobenzene 1,2,3-Trichlorobenzene . 1,2,4-Trichlorobenzene 35.05 16.83 26.51 (Ethylsulfony1)benzene 4.90 (2-Methoxyethoxy)ethene
21.40 2-Methylpropanoic acid, l-(l,l-dimethylethyl)-2-methyl-l,3 -propanediyl ester
36.88 3-Nitro-1,2-benzenedicarboxylic acid 1,2-benzenedicarboxylic acid, bis(2-ethylhexyl) ester 11.04 2,5-Dimethylphenol 22.69
12.47 1,2,4-Trichlorobenzene 1,2,3-Trichlorobenzene 1,3,5-Trichlorobenzene 7.90 6.22 7.47 1,2,3-Trimethoxypropane 26.05 Caff e ine 9.68 Chloroform
19.43 2-Hydroxy-1,4-naphthalenedione 2-Isopropylidenedihydrobenzofuran-3-one 39.27 1,2-Benzenedicarboxylic acid, dibutyl ester 1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) ester N 1 0 0 ('CI 0 1 0 n :1
,-I n .-
:1
3 II I 3 3
5s f t f$. 3 1' n II 3 '1 1 1 :..I 3 :I 1 11
.* 1 11 '3 . 1 1. J 4 1 11 0.93 c i-.- .-:- ! 7- I *' ri I)!- I ! :: 8 .-+ r-i .. ij,E. :>- .- R .-!- .. e: L .:.. :- I &:. iz c.: .-. I: .-c TJ 5.: m .r+ sf ._ z !J .72 .r( .!! !_I t; 10 !% ..+.. -!! 5 .?i 7.T.- !J ii.. i..! % .:i -. .r-. .:..I: .A .:-: ti 3 .. .. r- _.'* i.: !sj iJ .rj z c .- i3 I-:- .. .: i .- ....I 5 - :*. :>. f i: C' E! ._ t-- ._c @I- r. r. I !I _!3 :..; 9-j L7.j t! 1
u H I- 4
!& H W a H ccn
5 E High Point Eastside Influent 3/26/86 CLLE
Retention Time 12.00 linalyl propionate o(- t1erp ineo 4.25 2-butoxyethanol 21.89 1,2,3,5,6-pentathiepane 1,Z14-trithiolane 9.00 4-methylphenol 3- 11
28.32 hexadecanoic acid 7.57 2-ethyl-1-hexanol 23.50 hexathiepane 6.39 phenol 43.41 desacetylcinobufagin N-hexyl-2-benzothiazolamine 40.41 10-demethylsqualene trans-farnesol 43.84 3P-cholest-5-en-301 11.64 naphthalene 23.39 octacosane 2,6,10,15-tetramethylheptadecane 13.75 6-amino-hexanoic acid hexahydro-2H-azepin-2-one
9.89 1,2,3,5-tetramethylbenzene 1,2,3,4- n 1,2,4,5- 11
10.10 l12,4,5-tetramethylbenzene 1,2,3,4- 11 1,2,3,5- 11 34.65 octadecanoic acid, butyl ester butyl myristate 34.a3 tetracosane iron,tricarbonyl[N-(phenyl-2-pyridinylmethylene)benzenamine-N,N'] heneicosane 21.43 hexadecane n 1-iodoctatetracontane 8-methylheptadecane 1 24.68 tetradecanoic acid 25.25 tetracosane 3 octadecane 27.04 heneicosane docosane n (other hydrocarbons) 26.03 caffeine 38.80 hep tacosane triacontane (other hydrocarbons)
I- '1 33.40 tr ic os ane hexatriacontane rl (other hydrocarbons) 29.11 molecular sulfur 32.65 36. a3 1,2-benzenedicarboxylic acid, bis(2-ethylhexyl) ester It 3-nitro 41.23 heneicosane tr ic os ane octacosane
37.51 tr ic os ane 9-butyldocosane 36.23 heneicosane pentacosane 3 28.75 eicosane 2,6,10,15-tetramethylheptadecane doc0s ane
L- :1 6.86 2-(2-ethoxyethoxy)ethanol J 18.82 30.18 1- oc tade cano 1 1-heptadecene 1-docosanol 9.53 2-methyldecane 3,6-dimethyldecane 5-methylundecane 40.05 hep taco sane 1 pentacosane (0ther hydrocarbons) -I 14.71 1H-indole 31.5 hexadecanoic acid 3 octadecanoic acid 31.36 1 26.75 1-pentadecanol 1 - oc tadecano 1 2-hexadecanol
:1 16.68 decanoic acid
8.11 (1-methylpropy1)benzene :.I 1-methyl-3-propylbenene 1- 1' -2- n
10.78 2,3-dihydro-l-methyl-lH-indene 3 W -4- I1 I1 -5- 11 1 1R-methyl-2T-phenylcyclopropane 3 1.1 1 :I :I 1 3 I 3 11 High Point Eastside Effluent 3/26/86 CLLE
Retention Time ComDounds from Library Search
4.4 2-Hexanone, 5-methyl 2-Nonanone 2-Tridecanone 17.8 Benzoic acid, butyl ester Benzenebutanoic acid, gamma, -oxo Thiophene-2-01,benzoate
25.8 1-Butene, 4-bromo-3-chloro-3,4,4-trifluoro Spiro[bicyclo]o[3,2,1] oct-3-one-2,2'-[1,3]dioxolane 1H-Indole-3-adeticacid, 5-methoxy 38.1 2-Undecene, 5-methyl Pentane, 2,2,3,3-tetramethyl Heptane, 3 -bromo 9 .o Benzene, 1,2-dichloro 20.9 Phenol, 2,6-bis(l,l-dimethylethyl)-4-methyl Phenol, 2,6-bis(l,l-dimethylethyl)-4-methyl-,methylcarbamate Cyclohexanecarboxylic acid, 1-phenyl, methyl ester 22.5 1,2-Benzenedicarboxylicacid, diethyl ester 1,2-Benzenedicarboxylicacid, dipropyl ester 1,2-Benzenedicarboxylicacid, 2-ethoxy-2-oxoethy1,ethyl ester
24.0 1H-Indole-3-aceticacid, ethyl ester Quinoxaline 2,3-Pyridinedicarbonitrile 35.2 Phenol, 2-(l-methylethoxy)-methylcarbamate 11.5 Phosphoric acid, triethyl ester 2 -0ctan01 2-Propanone, 1-cyclopentyl-3-ethoxy 29.3 1,2-Benzenedicarboxylic acid, dibutyl ester 1,2-Benzenedicarboxylicacid, butyl 2-methylpropyl 1,2-Benzenedicarboxylic acid, dipropyl ester 13.0 Azulene Naphthalene Bicyclo [4,4,1]undeca-1,3,5,7,9-pentaen-ll-one i
48.0 2-Nonen-1-01,(E) I Furan, 2,3-dihydro-4-(l-methylethyl) Cyclohexane, 1,2-dimethyl-,cis 1 46.6 1,3-Cyclopentanedione,4-hydroxy-2-methyl Propane, 2-(2-isopropylidene-3-methylcyclopropyl), trans i Bicyclo[2.2.l]heptane,l,3,3-trimethyl 5.1 2-Cyclohexen-1-01 2,4-Hexadion-l-ol l-Butene, 2-ethyl-3-methyl I 5.3 Propane, l-ethoxy 3-Hexanol, 5-methyl I 3-Heptanol 6.1 2-Cyclohexen-1-one Pheno1 I Methyl amine, N-cyclopentylidene 8.9 Cyclohexanone, 3-methyl-(2,4-dinitrophenyl)hydrozone Propanoic acid, octyl ester I l-Pentene, 4-methyl 15.8 1,7-0ctodiyne II Benzene, (3-chloroallyl) Benzene, (l-ethyl-2-propenyl) 17.9 1,l-Biphenyl I Acenaphthalene, 1,2-dihydro Benzene, (2,4-cyclopentadion-l-ylidenemethyl) 18.6 4,7-Methano-lH-indene,3a,4,7,7a-tetrahydro I 5-Azatricyclo [7,2,0,01,4]undeca-2,5,7,10-tetraene, 6-methoxy Naphthalene, 1,2,3,4-tetrahydro-l,5-dimethyl i 19.9 Benzene, 1-(2-bromomethyl)-4-methoxy Benzene, l-methoxy-4-propyl Methanone, cyclohexyl-3-furanyl I 20.0 Ethanone, 1-(3,4-dimethoxyphenyl) 6-Nonynoic acid l,$-Nonadiyne i 20.4 Benzeneactaldehyde, alpha-phenyl Hydrazine, phenylsulfinyl 1 Benzene, 1,l-ethylidenebis 22.6 2-Hepten-3-01,4,5-dimethyl Butyric acid, thio, S-decyl ester i Butyric acid, thio, S-sec-butyl.ester 23.4 1,3-Propanediol,2-methyl-2-propyl 2-Piperidinone 1 2-Pentanone, l-methoxy-3-methylene ! 23.7 Benzene, 1,l'-[oxybis(methylene)]bis Benzene, methyl 1,5-Heptadion-3-yal
26.5 Pyridine, 4-(methylthio) Bicyclo [5,1,0] octane-3-01, (l,alpha, 3, alpha, 7, a1,pha) Carbonochloridic acid, 3-chloropropyl ester
26.8 Piperidine, 1-methyl Ethanol, 2,2,2-trichloro
36.2 2H-Pyrrol-2-one,1,5-dihydro-5-methoxy3-5-dimethyl
36.6 Carbonic acid, neopentyl phenyl ester Benzene, (1,2-dimethyl propoxy) Ethanol, 2-phenoxy 1-
I I
I High Point Eastside Influent 4/01/86 CLLE I Retention Time Compounds from Library Search 12.02 & - Terp ineo 1 Linalyl propionate
I 8.98 4-Methylphenol 3-Methylphenol I 21.90 1,2,3,5,6-Pentathiepane 29.14 Molecular sulfur
I 23.51 Hexathiepane
26.04 Caffeine I 7.59 1,2-Dichlorobenzene 18.76 1,3-Dihydro-2H-indol-2-one I 2,3-Dihydro-4-methyl-lH-indole
15.73 No Library match I 21.29 1,2-Benzenedicarboxylic acid, diethyl ester I 6.41 Phenol i I I i I 1
1 1 I -1 I
1I 1 1 n :I 3 n :I
'1L_
1-I 1 .1
'IL- _i
Ll 52 R 0 I! 0 Ld
I,- I,- ..
...,
0 H I- I-
34 .. E5 -Ti- 0 CD LD m n
1P I T I?
C mH c c
K -?
5 a E 3 m it 0 I d LD In
t
...... ; ..+ .... t- (~ ., i;.~...... j -f- d -!I ...... !... -. ,- , . I 1411; .. 1.. ?::! c
J
I High Point Blank 3/12/86 CLLE
Retention Time ComDounds from Librarv Search
8.93 1,2-dichlorobenzene 1,4-dichlorobenzene 1,3-dichlorobenzene
4.3 2,4-dimethyl-2-pentene
5-methyl-4-hexen-3-one I 6,d-dimethylcyclopropanemethanol
6.15 No library match
16.55 4-(l-methylethyl)benzoic acid, methyl ester z H IE \ wL3 n CD
u t-. u H I- I-
I
7
b
I
I Durham Influent 2/03/86 CLLE 2/07/86
Retention Time Compounds from Library Search 12.0 1,4-Hexadiene,2-methyl 2,5-Heptadiene 9-Cycloheptadecen-l-one 9-Octadecenal
13.2 3-Cyclohexene-l-methanol,a ,o( , 4-trimethyl, acetate 3-Cyclohexene-1-01,4-methyl-l-(l-methylethyl), acetate Cyclohexene, l-methyl-3-(l-methylethenyl) 3-Cyclohexene-l-methanol,a, w, 4-trimethyl 10.2 3-methylphenol 4-methylphenol 2 -methy lpheno 1 15.9 Benzeneacetonitrile 1H - indo le Benzene, l-isocyano-4-methyl Benzonitrile, 3-methyl 23.2 Benzene, l-[(l,l-dimethylethyl) thiol-2-methyl 1,2,4,6-tetrathiepane - 3-Dodecanol, 3,7,11-trimethyl 1,2,3,5,6-pentathiepane 27.3 lH-purine-2,6-dione,3,7-dihydro-1,3,7-trimethyl Borane, l-cycloocten-l-yldiethyl 7.1 Trisulfide, dimethyl Disulfide, dimethyl 41.6 9,17-0ctadecadienal 6,10,14-hexadecatrien-l-ol,3,7,11,15-tetramethyl 2H-cyclopentacycloocten-2-one, decahydro-3a-methyl, trans l-propyne, 3-(2-bromoethoxy) 24.9 Acetic acid, (4-formylphenoxy), ethyl ester hexathiepane
36.2 2,5,10-Undecatrienoic acid, methyl ester Cytidine, 2-deoxy-5-methyl Cyclododecene Ethanedioic acid, dibutyl ester 29.3 1,2-Benzenedicarboxylic acid, dibutyl ester 1,2-Benzenedicarboxylic acid, butyl 2-methylpropyl ester 22.5 1,2-Benzenedicarboxylic acid, diethyl ester 1,2-Benzenedicarboxylic acid, dibutyl ester 1,3-Benzenedicarboxylic acid 45.2 11,14,17-Eicosatrienoic acid, methyl ester Nonadecanol 1- hep tadecanol 1-tetracosanol 8.9 1,2-dichlorobenzene 22.6 Decane, 2,6,6-trimethyl Decane, 2,4,6-trimethyl Octane, 2,6,6-trimethyl Tridecane, 6-methyl 1- iodohep tane 24.6 Octadecane, 6-methyl Acetic acid, nonyl ester Heptadecane, 4-propyl Cyclooctanone, 2-methyl 1- Nonano 1 30.5 Sulfur, molecular 17.1 Pyridine, 3-(l-methyl-2-pyrrolidinyl) Benzene, 2,4-dimethyl-l-(l-methylpropyl) lH-Indole-2,3-dione,4-methyl lH-Indole-2,3-dione,6-methyl 17.8 2-Furanol, tetrahydro-2-methyl Cyclopentanone, 2,2-dimethyl l-hexene, 2-methyl Butane, l-(2,2-dichloro-l-methylcyclopropyl)
10.5 Borinic acid, diethyl,5-hexynyl ester Cyclohexanol, 4-sec-butyl 3,4-Pentadien-l-ol 1,2,4-trithiolane 12.8 6-Octen-1-01,3,7-dimethyl, proponate Cyclohexanol, 5-methyl-2-(l-methylethyl) 11,14-Eicosadienoic acid, methyl ester l-Undecyne 9,12-0ctadecadienoic acid
8.0 2-propanol, 1-(2-methoxy-l-methylethoxy) Octane Pentane, 2-methyl Pentane, 2-methoxy-2,4,4-trimethyl 2-Decanol 8.1 2-Propanol, 1-(2-methoxy-l-methylethoxy) 1,e-Butanediol
5.5 2,2-dimethyl propanoyl chloride 7-Octen-4-01 Propanoic acid, 2 propenyl ester Propane, l,l-[methylenebis(oxy)]bis[2-methyl] c 1
7.7 Pyridinamine
7.6 . . 2-Pyridinamine
12.7 Ethanone, 1-(2-Furanyl) 1,3-Benzenediol Ethanone, l-(lH-pyrazol-4-y1) 14.a 2H-Azepin-2-one,hexahydro 3 -0cten- 1-01 3-Piperidinone, 1-methyl ' I.
- Durham Influent
Retention Time ComDounds from Librarv Search 32.8 9,12,15-0ctadecatrienoic acid, methyl ester Cyclohexane, 1,l'-ethyldenebis 2(H)-Benzocyclooctenone, decahydro-loa-methyl,trans 9-Octadecenal 32.6 l-Hexacosanol 9,12-0ctadecadienoic acid l-Eicosene 9,17-0ctadecadienal 3.3 3-Penten-2-one,4-methyl 3-hexen-2-one
17.2 Pyridine, 3-(l-methyl-2-pyrrolidinyl) Benzoic Acid, 3,5-dimethyl 3(2H)-Benzofuranone, 5,6-dimethyl Benzene, 2,4-dimethyl-l-(l-methylpropyl) 4.1 2-pentanone, 4-hydroxy-4-methyl Propane, l-ethoxy-2-methyl 13.2 Ethanol, 1-(2-butoxyethoxy) Ethanol, 2-(2-butoxyethoxy)
5.6 Ethanol, 2 -butoxy Ethanol, 2-[2-(2-methoxyethoxy)ethoxy], acetate Propane, 2,2'-[1,2-ethanediylbis(oxy)]bis(2-methyl) Methanol, dibutoxy 37.3 Benzamide, N-acetyl Benzamide, N-propyl Benzoic acid, 2-benzoylhdrazide 2,6-piperazinedione,4-benzoyl, 2-oxime
36.4 Nonanedioic acid, dibutyl ester Thiopene, 2-ethyl-5-propyl Thiopene, 2-ethyl-5-isopentyl
37.1 Benzami.de, N-propyl Benzoic acid, 2-benzoylhydrazide 2,6-Piperazinedione,4-benzoyl-,2-oxime Ethanone, 2-(fomyloxy)-l-phenyl
45.2 Cholestane, 4,5-epoxy 9 .o Benzene, 1,2-dichloro 25.2 Benzoic acid, l-methylethyl ester 1 1,2-propanedione, l-phenyl Ethanone, 2-chloro-l-phenyl I Benzoic acid, l-benzoyl-2,2-dimethylhydrazide 27.4 lH-Purine-2,6-dione,3-7-dihydro-1,3, 7-trimethyl . 3-Hexan-1-01,formate 3 Cyclopentene, l-pentyl Cyclopentane, (2-methylbutyldiene) 8.2 2-Butanol Ethanol, 2-(2-ethoxyethoxy) Propanoic acid, 2-hydroxy-2-methyl 47.6 l-Hexacosanol l-Eicosanol Tridecane 5-cyclohexyl, 5-cyclohexyl Nonadecanol 41.7 3,7,11-Tridecatrienenitrile, 4,8,12-trimethyl Bicyclo[2,2,l]hept-2-ene, 1,7,7-trimethyl 6,10,14-hexadecatrien-l-ol,3,7,ll,l5-tetra1nethyl 3,7,11-Tridecatrienoicacid, 4,8,12-trimethylmethylester 42.4 Octacosane Hexacosane Docosane, 7-hexyl hexadecane, l-iodo 24.6 Hep tadecane Octane, l-iodo Heptacosane Undecane, 2,7-dimethyl 20.5 Pentadecane Octacosane e”. Hep tacosane Octadecane, 3-ethyl-5-(2-ethylbutyl) 25.4 Ethanone, 2-chloro-l-phenyl Ethanone, 2-bromo-l-phenyl 1,2-Propanedione, l-phenyl 2-Quindinecarbonitrile, l-benzoyl-1,2-dihydro Ethanone, 2-chloro-l-phenyl Benzamide , N-propyl Benzoic acid, 2-benzoylhydrazide 2,6-Piperazinedione, 4-benzoyl, 2-oxime l-Hexacosanol l-Eicosene l-Eicosanol 9,12-0ctadecadienoic acid Nonadecanol 22.6 Octacasone n Hexadecane Hep tacos ane 1 Undecane, 2,7-dimethyl 17.0 Pyridine, 3-(l-methyl-2-pyrrolidinyl) Benzoic acid, 3,5-dimethyl 2-piperidineacetic acid 3 2-propanone, l-(l-methyl-2-pyrrolidinyl)
38.2 Decane, 2,6,7-trimethyl Tert-dodecanethiol Ether, butyl isopentyl Hexane, l,l’-oxybis[2-ethyl-] 13 .O 3-cyclohexene 1-methanol Cyclohexene, l-methyl-3-(l-methylethylene) Bicyclo[3.l.0]hexan-2-01, 2-methyl-5-(l-methylethyl)
15.2 2H-Pyran, tetrahydro-2-(2-propynyloxy) 2H-Azepin-2-one,hexahydro
38.8 Tetracosane Doc o sane Heptadecane, 9-hexyl 41.3 Cholest-3-ene 1H-Purine, l-methyl-6-(methylthiol) ./ I Durham Effluent 2/14/86 CLLE
Retention Time ComDounds from Library Search
3.3 3-Penten-2-one, 4-methyl 3-Hexen-2-one
4.2 2-Pentanone, 4-hydroxy-4-methyl
8.9 1,2-Dichlorobenzene
9.6 2-Cyclohexen-l-one, 3-methyl
13.2 Undecane, 5,7-dimethyl Undecane, 3,7-dimethly
12.0 1H-1, 2,4-Triazole
9.5 Oxazolidine, 2,2,5-trimethyl-3-propyl 4-heptanone, 2-methyl
8.7 Cyclohexanol, 2-chloro, trans
22.6 2-Undecen-4-01 Butyric acid, ester w/butyl lactate Pentane, 2 - iodo n I
1 Durham Effluent 3/19/86 CLLE
Retention Time Compounds from Library Search 8.9 Benzene, 1,2-dichloro Benzene, 1,4-dichloro Benzene, 1,3-dichloro
8.7 1H-Pyrrole, 1-methyl Cyclohexane, 1,3-dichloro,cis 1-Hexene-3-01 43.0 1,2-Benzenedicarboxylicacid, dipentyl ester 1,2-Benzenedicarboxylicacid, dibutyl ester 1,2-Benzenedicarboxylic acid, butyl 2-methylpropyl ester
40.6 1,2-Benzenedicarboxylic acid, dipentyl ester 1,2-Benzenedicarboxylicacid, dibutyl ester 1,2-Benzenedicarboxylic acid, butyl 2-methylpropyl ester 1-Hexene, 2-methyl 26.7 Phosphorothioic acid, 0,O-diethyl Triacontane Octadecane, 3-ethyl-5-(2-ethylbutyl)
45.2 1,2-Benzenedicarboxylic acid, dibutyl ester 1,2-Benzenedicarboxylicacid, butyl 2-methylpropyl ester 1,2-Benzenedicarboxylic acid, dipentyl ester 47.6 1,2-Benzenedicarboxylic acid, dipentyl ester 1,2-Benzenedicarboxylic acid, dibutyl ester 1,2-Benzenedicarboxylic acid, bis (1-methylethyl) ester Aziridine, 2-methylene-l-(l-methylethyl) 45.3 Pentalene, octahydro-l-(2-octyldecyl) 9-Octadecenoic acid Manganeese, tricarbonyl 2-Propen-1-01
54.3 1-Heptanamine, N-heptyl Heptane, 2-methyl Heptane, 1-(2-propenyloxy) 1-Hexene-3-one
39.6 1,2-Benzenedicarboxylic acid, I ibuty - ester Nonane, 2,3-dimethyl 1-Propanol, 2,2-dimethyl-4-nitrobenzoate
31.8 1,4-Methano-2H-cyclopent(d)oxepin-2,5(4H)dione Cyclohexaneethanamine, N-alpha-dimethyl 2 -Heptan01 , 3 -methy1 9.7 1,2-Cyclohexanediol, trans Cyclohexanone, 3-methy1, (2,4-dinitrophenyl)hydrazone Propane, l-Bromo-2,2-dimethyl 38.1 1,2-Benzenedicarboxylic acid, dibutyl ester 11 , butyl 2-methylpropyl 11 , bis(1-methylethyl) ester
50.3 2H-Pyran-2-01,tetrahydro 12.2 Phenol, 2,s-dimethyl 11 It 9 284- n '* 9 296- 6.1 2-cyclohexen-l-one Butanoic acid, 4-hydroxy-2-methylene 1,2-Pentadiene,4-methoxy-4-methyl 2H-Pyran-2-one 37.2 1,2-Benzenedicarboxylic acid, dibutyl ester I1 , dirpropyl ester n , butyl 2-methylpropyl ester l-Penten-3-one,4-methyl 42.2 1,2-Benzenedicarboxylic acid, dibutyl ester Octane, 2,5-dimethyl Butane, 2-isocyanate 54.3 1-Heptanamine, N-heptyl Heptane, 2-methyl Heptane, 1-(2-propenyloxy) l-Hexen-3-one 39.7 1,2-Benzenedicarboxylic acid, dibutyl ester 11 , bis(1-methylethyl) ester I1 , butyl 2-methylpropyl ester Cyanic acid, sec-butyl ester
46.6 Pentalene, octahydro-l-(2-octydecyl) 7,10,13-Hexadecatrienoic acid, methyl ester lH-3a,7-Methanoazulene,octahydro 1,4,9,9-tetramethyl 20.5 Pentadecane Nonacosane Hep tacos ane
45.3 Pentalene, octahydro-l-(2-octyldecyl) 9-Octadecenoic acid Manganeese, tricarbonyl 2-Propen-1-01 5.0 2,4-Hexadien-l-ol l-Hexene, 6-nitro Diazene, cyclohexylmethyl-,1-oxide '1
1 24.7 Tetracosane, 2,6,10,15,19,23-hexamethyl Eicosane, 7-hexyl .- Decane, 5-ethyl-5-methyl 38.2 Heptane, 5-ethyl-2-methyl Octane , 1- iodo Nonane, 2,6-dimethyl 2-Piperidinone, l-methyl 20.0 l-Heptadecanol l-Octadecane 1- Hep tadecane l-Hexadecane 29.4 1,2-Benzenedicarboxylicacid, dibutyl ester It , butyl 2-methylpropyl ester It , , dipropyl ester Benzene, dodecyl 41.7 1,2-Benzenedicarboxylicacid, dioctyl ester Bicyclo(2.2.l)heptane-2-one, 1,3,3-trimethyl 3,7,11-Tridecatrienenitrile, 4,8,12-trimethyl
24.6 Docosane, 7-hexyl Hep tadecane Nonacosane 44.3 1,2-Benzenedicarboxylicacid, dipentyl ester It , dicyclohexyl ester 11 , dibutyl ester
Octacosane Hep tadecane Nonacosane I 1
- 1 I I I
I I I I
I , I I I
I - , I Y I i I I Durham Influent 3/24/86 CLLE
Retention Time ComDounds from Library Search 45.9 Cholestan-l-one 33.7 9,17-0ctadecadienal 9,12-0ctadecadienal Cyclopentane
42.3 No library match 40.1 No libary match 37.8 No library match 48.6 l-Dotriacontanol Nonacosanol Oleic acid, tetradecyl ester
13.4 3-cyclohexene-l-methanol Bicyclo (3.1.0) hexan-2-01,2-methyl-5-(l-methylethyl) 2,4,6-0ctatriene, 2,6-dimethyl Cyclohexene, l-methyl-3-(l-methylethenyl) 40.4 No library match 45.4 Hexadecane, l-iodo 38.7 No library match 43.1 Hexadecane, l-iodo tetracosane, 2,6,10,15,19,23-hexamethyl Heptadecane, 9-octyl 20.9 Pentadecane Nonacosane Heptacosane
40.7 Tetracosane, 2,6,10,15,19,23-hexamethyl Eicosane, 7-hexyl Octadecane, 3-ethyl-5-(2-ethylbutyl)
42.0 Cholest - 3 - ene 27.8 lH-Purine-2,6-dione,3,7-dihydro-1,3,7-trimethyl Ethanone, l-(1,3-dimethyl-3-cyclohexen-l-yl) 2-Norbornanecarboxaldehyde, 3-methyl, 2-endo-3-exo 23.0 Hexadecane 3 Undecane, 2,3-dimethyl d Decane, 2,3,6-trimethyl 3 5.4 Ethanol, 2-butoxy n Ethanedioic acid, dibutyl ester Diazene, bis(1,l-dimethylethyl)
25.0 Hep tadecane Nonacosane Hep taco sane
18.6 Tetradecane Unedecane, 2,3-dimethyl Decane, 2,3,6-trimethyl
39.3 No library match
38.0 No library match I
J i, I
-1
Durham Effluent 3/24/86 CLLE
9.0 Benzene, 1,2-dichloro It , 1,4-dichloro n , 1,3-dichloro
41.1 1,2-Benzenedicarboxylicacid, dipentyl ester 11 , dibutyl ester 11 , butyl 2-methypropyl ester
43.6 1,2-Benzenedicarboxylic acid, dibutyl ester 11 , butyl 2-methylpropyl ester It , bis(1-methylethyl) ester hydroperoxide, pentyl 45.7 1,2-Benzenedicarboxylic acid, dipentyl ester 11 , dibutyl ester 38.7 2-Undecene, 5-methyl Heptane, 5-ethyl-2-methyl Hexane, 1,l'-oxybis(2-ethyl) 45.9 Cholestan-1-one 2H-1-Benzopyran-6-01 Pregn-20-en-3-01,20-methyl 38.5 1,2-Benzenedicarboxylic acid, dibutyl ester It , butyl 2-methylpropyl ester 11 , bis(1-methylethyl ester
40.1 1,2-Benzenedicarboxyli.c acid, dipentyl ester 11 , dibutyl ester 2 -Decanol 42.6 1,2-Benzenedicarboxylic acid, dipentyl ester I1 , dibutyl ester It , butyl 2-methylpropyl ester 1-Propene, 1-(2-propenyloxy) 40.3 1,2-Benzenedicarboxylicacid, butyl 2-methylpropyl ester Cyanic acid, sec-butyl ester Butane, 2-isocyanato Ethanethioic acid, S-(2-methylpropyl) ester 12.4 Phenol, 2,5-dimethyl 20.3 1-Dotriacentanol 1-Hexacosanol 17-Pentatriacontene 37.7 1,2-Benzenedicarboxylic acid, butyl 2-methylpropyl ester II , dipropyl ester Ethanethioic acid, S-(2-methylpropyl) ester 1
32.2 1,4-Methano-2H-cyclopent(d)oxepin-2,5(4H)dione 2-Pentamine, 2,4,4-trimethyl Hexylamine, 1,l-dimethyl 1 31.8 17-Pentatriacontene Nonaco sanol 1-heptacosanol J 23.0 Butyric acid, thio-, S-decyl ester 2-Butenedioic acid(E)-, bis(2-ethylhexyl) ester Carbonoic acid, dineopentyl 'ester n Decane, l-(nonylthio) 24.5 l-Dotriacontanol l-Hexacosanol 'I 17-Pentatriacontene l-Heptadecene 33.0 l-Eicosene 7-Heptadecene, 17-chloro 7- I# , 1-chloro 8- N , l-chloro 35.9 Benzonitrile, m-phenethyl 1,2-Benzenedicarboxylic acid, butyl 2methylpropyl ester 'c Benzene, 3-butenyl 36.6 Pentatriacontane Tetratriacontane Tetracosane
38.0 , Tetratriacontane Pentatriacontane Docosane, 7-hexyl Pentacosane
41.8 Tetratriacontane Hexadecane , 1-iodo Tetracosane, ll-decyl
42.2 3,7,11-Tridecatrienenitrile, 4,8,12-trimethyl It , 4,8,12-trimethyl,methyl ester
42.7 1,2-Benzenedicarboxylic acid, dibutyl ester Decane, 2-5-dimethyl Cyanic acid, sec-butyl ester hydroperoxide, pentyl
44, .2 Heneicosane, ll-(l-ethylpropyl) Oc tacosane tetracosane, ll-decyl Hep tade cane 44.8 1,2-Benzenedicarboxylicacid, dipentyl ester Undecane, 2-methyl Hydroxylamine, 0-hexyl ? Butane, 1-bromo-2-methyl 44.9 1,2-Benzenedicarboxylic acid, bis(2-ethylbutyl) ester I1 , dicyclohexyl ester J I1 , dibutyl ester 46.5 Dotriacontane Pentatriacontane tetratriacontane
47.1 6-Tridecene 9-Octadecenoic acid(z), hexyl ester Cyclohexanone, 4-ethyl
47.2 2H-Pyran, 2-(7-heptadecynyloxy)tetrahydro Azulene ... (1-methylethenyl) 47.7 Tetratriacontane Pentatriacontane Octacosane Nonadecane 48.2 1,2-Benzenedicarboxylic acid, dibutyl ester 11 , dipropyl ester Octane 1-Henen-3-one l-Penten-3-one,4-methyl 51.1 Pentanal, 2-methyl 2 -Heptadecanone 8.4 Benzene, 1,2-dichloro 1s , 1,4- " n 1* # 193- 8.7 Heptane, 2,3,5-trimethyl Cyclohexanone, 4-(l,l-dimethylethyl) 1-Hexen-3-01 r' Durham Blank 2/21/86 CLLE
Retention Time Compounds from Library Search 8.9 Benzene, 1,2-dichloro 40.5 1,2-Benzenedicarboxylic acid, dipentyl ester 1,2-Benzenedicarboxylic acid, dibutyl ester 1,2-Benzenedicarboxylicacid, butyl-2-methylpropyl ester 42.8 1,2-Benzenedicarboxylicacid, dibutyl ester 1,2-Benzenedicarboxylicacid, butyl 2-methylpropyl 1,2-Benzenedicarboxylicacid, dipentyl ester
22.6 2-Hepten-3-01,4,5-dimethyl Butyric acid, thio, S-decyl ester Furan, 2-butyltetrahydro 37.9 1,2-Benzenedicarboxylic acid, dibutyl ester 1,2-Benzenedicarboxylic acid, butyl-2-methylpropylester Pentane, 2-methoxy-2,4,4-trimethyl
45.1 1,2-Benzenedicarboxylicacid, dibutyl ester Cyclohexanecarboxylic acid, l-(1,l-dimethylethyl) 1,3-Dioxolane, 2-(l,l-dimethylethyl)-2-methyl 41.9 1,2-Benzenedicarboxylicacid, dicyclohexyl ester 4.4 1,2-Cyclohexanediol,cyclic sulfite, cis 1,2-Cyclohexanediol,cyclic sulfite, trans l-Butyne, 3-ethoxy-3-methyl 2-pentene, 2,4-dimethyl 12.2 2,5-dimethylphenol 39.5 1,2-Benzenedicarboxylic acid, dicyclohexyl ester Ether, hexyl pentyl l-Butanol, 2-ethyl n m I
I
:I
. I I. Durham Blank 3/19/86 CLLE
Retention Time ComDounds from Library Search 9.0 1,2-Dichlorobenzene 41.0 1,2-Benzenedicarboxylicacid, dipentyl ester 11 , dibutyl ester n , butyl 2-methylpropyl ester
45.7 1,2-Benzenedicarboxylicacid, dipentyl ester 11 , dibutyl ester I1 , butyl 2-methylpropyl ester
43.5 1,2-Benzenedicarboxylic acid, dibutyl ester 11 , butyl 2-methylpropyl ester It , dipropyl ester
26.2 l-Butene, 4-bromo-3-chloro-3,4,4-trifluoro Ethane, l-chloro-2-nitro Acetamide, 2,2,2-trichloro-N-phenyl
38.5 1,2-Benzenedicarboxylicacid, dibutyl ester n , butyl 2-methylpropyl ester I1 , bis(1-methyl-ethy1)ester
42.5 1,2-Benzenedicarboxylicacid, dibutyl ester ? dicyclohexyl ester 2-Propenal, 3-(2-Furanyl)
35.7 No Match 37.6 1,2-Benzenedicarboxylic acid, dibutyl ester
11
37.0 Benzene (1,2-dimethylpropoxy) Benzene, butoxy 1,3-Cycloheptadiene
12.4 Phenol, 2,5-dimethyl 38.6 Undecane, 4,6-dimethyl Pentadecane, 2,6,10,14-tetramethyl Octane, 2,5,6-trimethyl 40.0 1,2-Benzenedicarboxylicacid, dipentyl ester I1 , dibutyl ester 11 , butyl 2-methylpropyl ester 2,4-Pentanedione, 3-diazo
40.2 1,2-Benzenedicarboxylicacid, dibutyl ester 42.7 1,2-Benzenedicarboxylic acid, dibutyl ester Octane, 2,5-dimethyl Heptane, 3,5-dimethyl 44.7 1,2-Benzenedicarboxyic acid, dicyclohexyl ester 11 , dibutyl ester Hexane, 3-ethyl Butane, 2-isocyanato 44.8 1,2-Benzendicarboxylic acid, dicyclohexyl ester Tricyclo (4.3.1.13,8) undecane, l-chloro Tricyc lo 11 , l-Bromo 2-Cyclohexen-l-one,3-methyl-6-(l-methyl ethenyl) 47.1 1,2-Benzenedicarboxylic acid, dipentyl ester Pyrrolidine, 1-(2-methyl-l-butenyl) Cyclohexanone, 2-(dimethylamino) 48.2 1,2-Benzendicarboxylic acid, dibutyl ester 11 , bis(1-methylethyl) ester 2-0ctanone, 1-nitro 1,2,3-Cyclohexanetriol 2H-Pyran, tetrahydro-2-(methylthio) 22.8 1,2-Benzedicarboxylic acid, diethyl ester 11 , dipropyl ester I1 , 2-ethoxy-2-oxoethyl
29.7 1,2-Benzenedicarboxylic acid, dibutyl ester 11 , butyl 2-methylpropyl ester 11 , dipropyl ester
20.7 Benzene, 1,l'-ethylidenebis Benzene, 1,l'-(chloromethy1ene)bis Propanoic acid, 2-methyl, 2-pentylethyl ester
13.1 Bicyclo(4.4.l.)undeca-l,3,5,7,9-pentaen -11-one Azulene Naphthalene 8.6 Disulfide, 1,l-dimethylethyl methyl Butanamide, N((acetylamino)carbonyl)2-broma-2-ethyl Cyclohexane, 1,2-dichloro, trans 5-Hexene-3-one
37.4 1,2-Benzenedicarboxylic acid, butyl 2-methylpropyl ester 2-Propen-l-amine,N-2-propenyl 1,4-Cyclohexanediol,diacetate, trans 39.2 Decane, 5-methyl I1 Pentadecane, 5-methyl ‘1 .- ’ Heptane, 2-methyl 39.7 1,2-Benzedicarboxylic acid, dipentyl ester 4(1H)-Pyrimidinone, 2,3-dihydro-2-thioxo 4-Pentenal, 2,2-dimethyl 41.5 1,2-Benzenedicarboxylic acid, dipentyl ester Cyclopropane, l,l-dimethyl-2-nonyl 3-Decene, 2-methyl 42.2 1,2-Benzenedicarboxylic acid, 2-butoxyethyl butyl ester Ethane, 1-chloro-1-fluoro :1 3H-Pyrazol-3-one,2,4-dihydro-4,4,5-trimethyl 43.8 4-Octenoic acid, 6-ethyl-3-hydroxy-3,7-dimethyl Ketone, 2,2-dimethylcyclohexylmethyl 1 2-0xabicyclo(2.2.2)octane, 1,3,3-triethyl 44.2 Butamide Butanoic acid, 3-methyl-2-methylene,methyl ester 2 -Butenediamide 3H-Pyrazol-3-one,2,4-dihydro-4,4,5-trimethyl n 3 3 3 +
I Durham Blank 3/24/86 CLLE
Retention Time Compounds from Library Search 9.0 1,2-Dichlorobenzene 41.0 1,2-Benzenedicarboxylicacid, dibutyl ester 1,2-Benzenedicarboxylicacid, dicyclohexyl ester 1,2-Benzenedicarboxylicacid, butyl 2-methylpropyl ester Butane, 2-isocyanato
43.4 1,2-Benzenedicarboxylicacid, dipentyl ester 1,2-Benzenedicarboxylicacid, dipropyl ester 1,2-Benzenedicarboxylicacid, dibutyl ester
4.5.7 1,2-Benzenedicarboxylic acid, dipentyl ester 1,2-Benzenedicarboxylic acid, dibutyl ester l,a-Nonanediol, 8-methyl Cyclohexanamine, 5-methyl-2-(1-methylethyl) 38.4 1,2-Benzenedicarboxylic acid, dibutyl ester 1,2 Benzenedicarboxylic acid, butyl 2-methylpropyl ester 2-hexanone, 3-hydroxy-3,5-dimethyl 38.6 Hexanal, 4-methyl 1-Hexene, 3,4,5-trimethyl 1,2-Benzenedicarboxylicacid, dioctyl ester 1-Hexene, 5-methyl
40.0 1,2-Benzenedicarboxylicacid, dicyclohexyl ester Cyanic acid, butyl ester 3-piperidinol, 1-ethyl 40.2 1,2-Benzenedicarboxylic acid, dibutyl ester 1,2-Benzenedicarboxylic acid, dipropyl ester 4(3H)-Pteridinone, 2,6,7-trimethyl
42.7 2-Hexanone, 3-hydroxy-3,5-dimethyl 1,2-Benzenedicarboxylic acid, dipropyl ester 2-Buten-1-one 2-Hexanone, 5-methyl 43.4 1,7-0ctanediol,3,7-dimethyl 1-Hexen-3-one Pentanal, 3-methyl
37.6 Phenol, 4-(l,l-dimethylethyl)-2-methyl 22.8 1,2-Benzenedicarboxylicacid, diethyl ester 1,2-Benzenedicarboxylic acid, dibutyl ester 1,2-Benzenedicarboxylic acid, dipropyl ester 22.9 2-Hepten-3-01, 4,5-dimethyl 2-Butanol, 2-nitroso-, acetate (ester) Butane, l-bromo-2-methyl Furan, 2-butyltetrahydro