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2012_April_Progress Report 1 PROGRESS REPORT: APRIL 2012

BIODEGRADATION TESTING SUPPLEMEN TAL ENVIRONMENTAL PROJECT

Submitted to

E.I du Pont de Nemours and Company Wilmington, Delaware 19898 U.S.A.

United States Environmental Protection Agency Washington, DC U.S.A. 

# Wildlife International, Ltd.

8598 Commerce Drive Easton, Maryland 21601 USA 1 (410) 822-8600

April 30, 2012

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2012_April_Progress Report 2 Table of Contents

Title Page .................................................................................................................... ...............1
Table of Contents ............................................................................................................. ..........2
Introduction .................................................................................................................. ..............3 Progress Summary .............................................................................................................. .......3 Appendix A. Invoice .......................................................................................................... .......8 Appendix B. Calibration Curves and Chroma tograms for Telomer Alcohol Standards byLC/MS/MS Before and Following Analysis of Activated Sludge MixedLiquor Fortified with Group A1 Polymers ......................................................10
Appendix C. Summary Data fo r Method Trials 1 Through 8 .................................................16 Trial 1 - Sludge and polymer b ackground - 2 MTBE extractions ...................17 Trial 2 - Telomer alcohol fortifie d sludge - 2 MTBE extractions ....................25 Trial 3 - Mass-labeled telomer alcohol and polymer fortified sludge - 3 MTBE extractions ..........................................................................33 Trial 4 - Procedural blanks and post-spikes for previous trial .........................57 Trial 5 - Telomer alcohol fortifie d sludge - 5 MTBE extractions ....................63 Trial 6 - Influence of experiment al variables on telomer alcohol procedural recoveries ........................................................................71 Trial 7 - Telomer alcohol and lab- scaled synthesized A1 polymer fortified sludge - 5 MTBE extractions ..............................................79 Trial 8 - Telomer alcohol and lab-purif ied A1 polymer fortified sludge - 5 MTBE extractions ..........................................................................87
Appendix D. Percent of Total Telomer Al cohol Mass Recovered as a Function of Sequential MTBE Extraction Number .............................................................96 Appendix E. Records of Sample, Stoc k, Standard and Reag ent Preparation .........................98Does Not Contain Confidential Business Information (CBI)

2012_April_Progress Report 3 Introduction This document presents the pr ogress of the technical work for the Biodegradation Testing Supplemental Environmental Project (“Biode gradation SEP”) performed from 24 March 2012 up to 27 April 2012. Stud ies conducted under protocol will be examined by the Wildlife International Quality Assurance Unit for compliance with Good Laboratory Practices, Standard Operating Procedures and the specified protocol. Ra w data that has been audited by the Wildlife International Quality Assurance will be included in the progress report, as appropriate.

Progress Summary The total costs associated with the project for the period covered in this Progress Report are approximately $18,755 for labor, $5,482.99 for mate rials and $18,900 for instrumentation.
The invoice and an allocation of costs with a ssociated tasks are presented in Appendix A.

The technical work consisted of a continuation of the work described in the SCAS Analytical Method Development Plan (20 Jan 2012.doc) as a pproved by EPA on February 14, 2012. In the March 2012 Progress Report, documentation of LC/MS/MS instrumental conditions, calibration standard ranges and st ability was provided in support of subsequent planned trials
to demonstrate determination of the telomer alcohol analytes 6-2 FTOH, 8-2 FTOH and 10-2
FTOH in MTBE-extracted SCAS matrices in the presence of Group A1 polymers. The completion of the above referenced method tr ials and their findings are summarized and presented here. A total of eight separate method trials were performed within the timeframe of the present report.

Using the recently established instrumental co nditions, freshly collected SCAS matrix was fortified with Group A1 polymer extracted tw ice with MTBE and analyzed by the proposed methodology to demonstrate an absence of a ca libration function shift or analyte carry-over
associated with GCMS determinations of 6-2 FTOH, 8-2 FTOH and 10-2 FTOH. At an equivalent loading of 180 mg/L of each Gr oup A1 polymer (or 540 mg/L as the test substance – aqueous dispersed polymer at 32.5 wt%), no such e ffects were evident using the proposed LC/MS/MS methodology (Appendix B).Does Not Contain Confidential Business Information (CBI)

2012_April_Progress Report 4 The first trial employed two sequential MTBE ex tractions at the same matrix-to-extraction ratio (2.5 mL MTBE: 10 mL SCAS mixed-liquo r) prescribed in the most recent proposed activated sludge mixed-liquor method out line (e.g., August 2011 Progress Report). Background activated sludge mixed- liquor without addition of polymer was also analyzed
and showed no detectable traces of the three telomer alcohol analytes. Quantifiable amounts of the three telomer alcohols, presumably resi duals from the specific manufacturing process, were evident in the polymer fortified matrices. It was noted that the polymer fortified matrices yielded a substantial percentage of th e total measured mass of telomer alcohol in the
second extract for each of the telomer alcohols investigated. The percentage of the total
recovered mass recovered in the second extrac tion increased with telomer alcohol chainlength and ranged from a mean of 36% for 6- 2 FTOH to 77% for 10-2 FTOH. The trends were consistent for both polymers although the total measured residual mass of each telomer alcohol for the lab-purified (sparged) polymer (WLI No. 9373) was approximately seven times greater compared with the lab-scaled synthesized variant (WLI # 9382) following two sequential MTBE extractions. (Note: summary da ta and experimental details for each of the eight method trials are pr ovided in Appendix C).

In the second trial, approximately 300 nanogram s each of the three telomer alcohols were fortified into activated sludge mixed-liquor without addition of polymer and the samples
were twice extracted with MTBE as before to see if the polymer matrices were having an influence on extraction efficiency for telomer alcohol residuals. The mean percent recoveries were 55%, 75% and 84% of the nominal for tified mass for 6-2 FTOH, 8-2 FTOH and 10-2 FTOH, respectively. Although acceptable reco very was obtained for 8-2 FTOH and 10-2 FTOH, the total mass recovered in the second MTBE extraction for all three telomer alcohols was still a significant percentage of the to tal fortified mass (range 24% - 30%). One difference noted from the previous trial, wher e polymer was present in the matrix and the
telomer alcohols were most likel y associated with re siduals in the test material, was an absence of the significant skewing to higher pe rcentage of total mass in the second MTBE extraction with increased telomer alcohol chain-length.

The SCAS Analytical Method Development Pl an specifies performing a telomer alcohol fortification into the anticipate d SCAS testing matrix which consists of both the polymer andDoes Not Contain Confidential Business Information (CBI)

2012_April_Progress Report 5 activated sludge mixed-liquor. Producing a defendable result was deemed challenging following completion of the first two trials gi ven the magnitude and distribution of telomer alcohol background levels observed across th e two MTBE extractions, low procedural recovery obtained for 6-2 FTOH, and the expectation to perform sequential MTBE
extractions until less than 10% of the total mass was recovered in the final extraction. In an attempt to overcome these limitations, 13 C labeled telomer alcohols were fortified into the SCAS testing matrix at the same levels used fo r the unlabeled materials in the second trial. In addition, three sequential MTBE extractions were performed instead of two sequential
MTBE extractions. Modification to the base LC/MS/MS method were required to allow monitoring of the 13 C labeled telomer alcohol recoveries and included specifying the expected mass transitions in the acquisition method, use of fewer calibration standards to conserve mass-labeled material, and elimina tion of matrix verification standards for quantitation. These same 13 C labeled telomer alcohols were employed for that purpose in the
base method.

Quantitative procedural recoveries were obtained for 13 C-labeled 6-2 FTOH and 8-2 FTOH for three sequential MTBE extractions at the fortification level used (312.5 ng). A subsequent post-spike test demonstrated that the matrix verification standard would have been required to effect quantitative recovery for 13 C-labeled 10-2 FTOH (Trial 4). In the case of 6-2 FTOH, the quantitative recoveries obtained in this trial were later attributed to use
of a fortification stock prepared in methanol versus MTBE (Trial 6), as opposed to studied experimental variables including number of extractions, extraction vigor and extraction solvent ratio. More significant, the third MT BE extraction was essential to obtain mass balance for each analyte and the third MTBE extract still contained an appreciable percentage of the total fortified mass. A sim ilar skewing of percentage of recovered mass with chain length as was observed for un-fortifie d SCAS/polymer matrices (e.g., in the initial trial) was evident. Another similarity with the previous trial was the finding that more 10-2 FTOH mass was actually removed in the second MTBE extraction than in the first MTBE extraction. In summary, these findings suggest th at at least four MTBE extractions may be required using the current extraction conditions to achieve the 10% of total mass criterion for completion of MTBE extraction steps in the overall method.Does Not Contain Confidential Business Information (CBI)

2012_April_Progress Report 6 The fifth trial was essentially a repeat of the second trial (non-labeled telomer alcohol
fortification into activated sl udge only) except that five sequ ential MTBE extractions rather than two sequential MTBE extractions were used. The purpose of this trial was to evaluate the requisite number of seque ntial extractions without poten tial recovery cal culation bias from the residual telomer alcohols in the polymers (please note that the 6-2 FTOH results for this fifth trial were generated before the change in fortification stock solvent (to methanol) was implemented (Note- For this evaluation, use of mass-labeled telomer alcohol in the presence of the polymers would have consumed an unacceptable quantity of material). The
results illustrate that less than 10% of to tal fortified mass was recovered in the fourth sequential MTBE extraction for 6- 2 FTOH, 8-2 FTOH and 10-2 FTOH.

Based on the findings from the previous trials , definitive telomer alcohol plus A1 polymer fortification trials were perfor med in activated sludge mixed- liquor using unlabeled materials and five sequential MTBE extractions (Trial 7 for lab-scaled synthesized A1 polymer and Trial 8 for the lab-purified A1 variant). The telomer alcohol and polymer fortification levels and the MTBE extraction ratios and extraction pr ocedures were identical to those employed for the previous trials. Fortification recoveries were tabulated by analyzing duplicate samples containing activated sludge mixed liquor and the applicable polymer, averaging the residuals in a given sequentia l extraction and subtracting the mean background from the corresponding sequential extract result from the telomer alcohol fortified sample (e.g., the mean background for MTBE extract “A” of the appropriate polymer fortified sludge sample is subtracted from extract “A” for a given telo mer alcohol fortification sample in the polymer fortified sludge sample of the same polymer type).

Five sequential MTBE extractions were requir ed in the presence of the A1 polymers to
demonstrate that all three telomer alcohols were below the 10% of total mass threshold (Appendix D). For the lab-scaled synthesi zed polymer, 6-2 FTOH was well below 10% by
the third MTBE extraction. For 8–2 FTOH a nd 10-2 FTOH, the fourth sequential MTBE
extraction still contained an av erage of approximately 7% and 14%, respectively, of the total mass in both activated sludge mixed-liquor sa mples fortified with polymer only and in samples fortified with both telomer alcohol anal ytes and the polymer. Acceptable proceduralDoes Not Contain Confidential Business Information (CBI)

2012_April_Progress Report 7 recoveries were obtained for all three telome r alcohols in activated sludge mixed-liquor samples fortified with lab-scal ed synthesized polymer matrix.

Another not unexpected finding was that the c hosen telomer alcohol fortification amounts were more appropriate relative to the residual levels present in the laboratory-scaled synthesized variant (approximate ly 3:1 fortified to residual telomer alcohol mass ratio). Although an approximately 3:7 fo rtified to residual telomer alcohol mass ratio was evident for activated sludge mixed-liquor samples for tified with lab-purified polymer, acceptable procedural recovery was f ound for all 8-2 FTOH and 10-2 FT OH fortified samples and for 6-2 FTOH in one of the replicates.

Records of sludge collection and preparation and records of stock, standard and reagent preparations required to perform the experimental trials summarized in this Progress Report are provided in Appendix E.Does Not Contain Confidential Business Information (CBI)

2012_April_Progress Report 8 Appendix A
InvoiceDoes Not Contain Confidential Business Information (CBI)2012_April_Progress Report9Allocation of CostsMonth, Year Tasks TotalDesign andProcurementof SCAS Units(Task A)AcquisitionofStandards(Task B)Adaptation ofAnalyticalMethod (Task C)Pilot StudiesTask (D)Refinementof MethodsTask (E)MethodVal(Task F)StorageStability(Task G)BiodStudies(Task H)InstrumentLeaseDec 2009 $1,803 $1,085 $42,422 $45,310Jan 2010 $29,227 $29,227Feb 2010 $1,300 $36,745 $38,045Mar 2010 $14,350 $14,350 $18,900Apr 2010 $570 $15,935 $16,505 $18,900May 2010 $760 $71,860 $72,620 $18,900June 2010 $57,870 $35,003 $92,873 $18,900July 2010 $42,430 $15,130 $57,560 $18,900Aug 2010 $32,530 $113,718 $146,248 $18,900Sep 2010 $1,350 $115,228 $116,578 $18,900Oct 2010 $88,823 $3,613 $92,478 $18,900Nov 2010 $42,690 $855 $570 $44,115 $18,900Dec 2010 $18,385 $3,530 $3040 $24,955 $18,900Jan 2011 $15,570 $15,570 $18,900Feb 2011 $2,945 $2,945 $18,900Mar 2011 $8,075 $8,075 $18,900Apr 2011 $9,820 $9,820 $18,900May 2011 $5,770 $5,770 $18,900June 2011 $2,850 $190 $3,040 $18,900July 2011 $2,965 $2,965 $18,900Aug 2011 $950 $10,713 $11,663 $18,900Sep 2011 $1,140 $1,140 $18,900Oct 2011 $380 $950 $1,330 $18,900Nov 2011 $1,235 $1,235 $18,900Dec 2011 $1,520 $1,520 $18,900Jan 2012 $1,140 $1,140 $18,900Feb 2012 $1,140 $1,140 $18,900Mar 2012 $5,335 $5,335 $18,900Apr 2012 $18,755Labor Total $1,803 $3,715 $344,719 $430,318 $97,920 $3,800 $882,275Materials $6,800 $10,500 $20,644 $1,724 $7,296 $46,965Total Cost $8,603 $14,215 $365,363 $432,042 $105,216 $3,800 $929,240 $491,400Does Not Contain Confidential Business Information (CBI)

2012_April_Progress Report 10 Appendix B Calibration Curves and Chromatograms for Telo mer Alcohol Standards by LC/MS/MS Before and Following Analysis of Activated Sludge Mi xed-Liquor Fortified with Group A1 Polymers

Representative Calibration Curve for 6-2 FTOH by LC/MS/MS

Note: All initial and final calibration standard injections included in calibration curve.Does Not Contain Confidential Business Information (CBI)

2012_April _Progress Report 11 Representative Calibration Standards for 6-2 FTOH by LC/MS/MS

(A)

(B)

(A): Before polymer analysis (B): After polymer analysisDoes Not Contain Confidential Business Information (CBI)

2012_April _Progress Report 12 Representative Calibration Curve for 8-2 FTOH by LC/MS/MS

Note: All initial and final calibration standard injections included in calibration curve.Does Not Contain Confidential Business Information (CBI)

2012_April _Progress Report 13 Representative Calibration Standards for 8-2 FTOH by LC/MS/MS

(A)

(B)

(A): Before polymer analysis (B): After polymer analysisDoes Not Contain Confidential Business Information (CBI)

2012_April_Progress Report 14 Representative Calibration Curve for 10-2 FTOH by LC/MS/MS

Note: All initial and final calibration standard injections included in calibration curve.Does Not Contain Confidential Business Information (CBI)

2012_April _Progress Report 15 Representative Calibration Standards for 10-2 FTOH by LC/MS/MS

(A)

(B)

(A): Before polymer analysis (B): After polymer analysisDoes Not Contain Confidential Business Information (CBI)

2012_April _Progress Report 16 Appendix C Summary Data for Method Trials 1 Through 8Does Not Contain Confidential Business Information (CBI)

2012_April _Progress Report 17 Trial 1 - Sludge and polymer background - 2 MTBE extractionsDoes Not Contain Confidential Business Information (CBI)

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2012_April _Progress Report 25 Trial 2 - Telomer alcohol fortif ied sludge - 2 MTBE extractionsDoes Not Contain Confidential Business Information (CBI)

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2012_April _Progress Report 33 Trial 3 - Mass-labeled telomer alcohol and pol ymer fortified sludge - 3 MTBE extractionsDoes Not Contain Confidential Business Information (CBI)

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2012_April _Progress Report 57 Trial 4 - Procedural blanks and post-spikes for previous trialDoes Not Contain Confidential Business Information (CBI)

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2012_April _Progress Report 63 Trial 5 - Telomer alcohol fortif ied sludge - 5 MTBE extractionsDoes Not Contain Confidential Business Information (CBI)

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2012_April _Progress Report 71 Trial 6 - Influence of experi mental variables on telomer al cohol procedural recoveriesDoes Not Contain Confidential Business Information (CBI)

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2012_April _Progress Report 79 Trial 7 - Telomer alcohol and lab-scaled synt hesized A1 polymer fortified sludge - 5 MTBE
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2012_April _Progress Report 88 Trial 8 - Telomer alcohol and lab-purified A1 polymer fortified sludge - 5 MTBE extractionsDoes Not Contain Confidential Business Information (CBI)

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2012_April _Progress Report 96 Appendix D
Percent of Total Telomer Alcohol Mass Recovered as a Function of Sequential MTBE Extraction Number

Average Polymer #1 (WIL 9373) Background

0% 10% 20% 30% 40% 50% 60%

12345 Extraction Number% Total Mass Recovered 6-2 FTOH 8-2 FTOH 10-2 FTOH Threshold

Average Polymer #2 (WIL 9382) Background

-10%

0% 10% 20% 30% 40% 50% 60%

12345 Extraction Number% Total Mass Recovered 6-2 FTOH 8-2 FTOH 10-2 FTOH ThresholdDoes Not Contain Confidential Business Information (CBI)

2012_April _Progress Report 97 Avera g e FTOH Fortified Pol y mer #2 ( WIL 9382 ) Recoveries (Background Subtracted)

0% 10% 20% 30% 40% 50% 60% 70% 80%

12345 Extraction Number% Total Mass Recovered 6-2 FTOH 8-2 FTOH 10-2 FTOH ThresholdDoes Not Contain Confidential Business Information (CBI)

2012_April _Progress Report 98 Appendix E Records of Sample, Stock, Sta ndard and Reagent PreparationDoes Not Contain Confidential Business Information (CBI)

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