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2012_April_Progress Report 1

PROGRESS REPORT: APRIL 2012 

BIODEGRADATION TESTING SUPPLEMENTAL 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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Table of Contents 

Title Page ...................................................................................................................................1 

Table of Contents .......................................................................................................................2 

Introduction ................................................................................................................................3 

Progress Summary .....................................................................................................................3 

Appendix A. Invoice .................................................................................................................8 

Appendix B. Calibration Curves and Chromatograms for Telomer Alcohol Standards by 

LC/MS/MS Before and Following Analysis of Activated Sludge MixedLiquor Fortified with Group A1 Polymers ......................................................10 

Appendix C. Summary Data for Method Trials 1 Through 8 .................................................16 

Trial 1 - Sludge and polymer background - 2 MTBE extractions ...................17 

Trial 2 - Telomer alcohol fortified 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 fortified sludge - 5 MTBE extractions ....................63 

Trial 6 - Influence of experimental 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-purified A1 polymer fortified sludge - 

5 MTBE extractions ..........................................................................87 

Appendix D. Percent of Total Telomer Alcohol Mass Recovered as a Function of 

 Sequential MTBE Extraction Number .............................................................96 

Appendix E. Records of Sample, Stock, Standard and Reagent Preparation .........................98 
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Introduction 

This document presents the progress of the technical work for the Biodegradation Testing 

Supplemental Environmental Project (“Biodegradation SEP”) performed from 24 March 

2012 up to 27 April 2012. Studies 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. Raw 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 materials and $18,900 for instrumentation. 

The invoice and an allocation of costs with associated 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 approved by EPA on February 14, 2012. In 

the March 2012 Progress Report, documentation of LC/MS/MS instrumental conditions, 

calibration standard ranges and stability 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 trials 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 conditions, freshly collected SCAS matrix was 

fortified with Group A1 polymer extracted twice with MTBE and analyzed by the proposed 

methodology to demonstrate an absence of a calibration 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 Group A1 polymer (or 540 mg/L as the test 

substance – aqueous dispersed polymer at 32.5 wt%), no such effects were evident using the 

proposed LC/MS/MS methodology (Appendix B). 
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The first trial employed two sequential MTBE extractions at the same matrix-to-extraction 

ratio (2.5 mL MTBE: 10 mL SCAS mixed-liquor) prescribed in the most recent proposed 

activated sludge mixed-liquor method outline (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 residuals 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 the 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 extraction 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 data and experimental details for each of the 

eight method trials are provided in Appendix C). 

In the second trial, approximately 300 nanograms 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 fortified mass for 6-2 FTOH, 8-2 FTOH and 10-2 

FTOH, respectively. Although acceptable recovery 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 total fortified mass (range 24% - 30%). One 

difference noted from the previous trial, where polymer was present in the matrix and the 

telomer alcohols were most likely associated with residuals in the test material, was an 

absence of the significant skewing to higher percentage of total mass in the second MTBE 

extraction with increased telomer alcohol chain-length. 

The SCAS Analytical Method Development Plan specifies performing a telomer alcohol 

fortification into the anticipated SCAS testing matrix which consists of both the polymer and 
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activated sludge mixed-liquor. Producing a defendable result was deemed challenging 

following completion of the first two trials given the magnitude and distribution of telomer 

alcohol background levels observed across the 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, 13C labeled telomer alcohols were fortified into the 

SCAS testing matrix at the same levels used for 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 13C 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 elimination of matrix verification standards for 

quantitation. These same 13C labeled telomer alcohols were employed for that purpose in the 

base method. 

Quantitative procedural recoveries were obtained for 13C-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 13C-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 MTBE 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 similar skewing of percentage of recovered mass 

with chain length as was observed for un-fortified 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 that 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. 
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The fifth trial was essentially a repeat of the second trial (non-labeled telomer alcohol 

fortification into activated sludge only) except that five sequential MTBE extractions rather 

than two sequential MTBE extractions were used. The purpose of this trial was to evaluate 

the requisite number of sequential extractions without potential recovery calculation 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 total 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 performed 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 procedures 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 sequential 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 telomer alcohol fortification sample in the polymer 

fortified sludge sample of the same polymer type). 

Five sequential MTBE extractions were required 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 synthesized polymer, 6-2 FTOH was well below 10% by 

the third MTBE extraction. For 8–2 FTOH and 10-2 FTOH, the fourth sequential MTBE 

extraction still contained an average of approximately 7% and 14%, respectively, of the total 

mass in both activated sludge mixed-liquor samples fortified with polymer only and in 

samples fortified with both telomer alcohol analytes and the polymer. Acceptable procedural 
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recoveries were obtained for all three telomer alcohols in activated sludge mixed-liquor 

samples fortified with lab-scaled synthesized polymer matrix. 

Another not unexpected finding was that the chosen telomer alcohol fortification amounts 

were more appropriate relative to the residual levels present in the laboratory-scaled 

synthesized variant (approximately 3:1 fortified to residual telomer alcohol mass ratio). 

Although an approximately 3:7 fortified to residual telomer alcohol mass ratio was evident 

for activated sludge mixed-liquor samples fortified with lab-purified polymer, acceptable 

procedural recovery was found for all 8-2 FTOH and 10-2 FTOH 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. 
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Appendix A 

Invoice 
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Allocation of Costs 

Month, Year Tasks 

Design and 

Procurement 

of SCAS Units 

(Task A) 

Acquisition 

of 

Standards 

(Task B) 

Adaptation of 

Analytical 

Method (Task C) 

Pilot Studies 

Task (D) 

Refinement 

of Methods 

Task (E) 

Method 

Val 

 (Task F) 

Storage 

Stability 

(Task G) 

Biod 

Studies 

(Task H

Dec 2009 $1,803 $1,085 $42,422 Jan 2010 $29,227 Feb 2010 $1,300 $36,745 Mar 2010 $14,350 Apr 2010 $570 $15,935 May 2010 $760 $71,860 June 2010 $57,870 $35,003 July 2010 $42,430 $15,130 Aug 2010 $32,530 $113,718 Sep 2010 $1,350 $115,228 Oct 2010 $88,823 $3,613 Nov 2010 $42,690 $855 $570 Dec 2010 $18,385 $3,530 $3040 Jan 2011 $15,570 Feb 2011 $2,945 Mar 2011 $8,075 Apr 2011 $9,820 May 2011 $5,770 June 2011 $2,850 $190 July 2011 $2,965 Aug 2011 $950 $10,713 Sep 2011 $1,140 Oct 2011 $380 $950 Nov 2011 $1,235 Dec 2011 $1,520 Jan 2012 $1,140 Feb 2012 $1,140 Mar 2012 $5,335 Apr 2012 $18,755 Labor Total $1,803 $3,715 $344,719 $430,318 $97,920 $3,800 Materials $6,800 $10,500 $20,644 $1,724 $7,296 Total Cost $8,603 $14,215 $365,363 $432,042 $105,216 $3,800 
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Appendix B 

Calibration Curves and Chromatograms for Telomer Alcohol Standards by LC/MS/MS Before 

and Following Analysis of Activated Sludge Mixed-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. 
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Representative Calibration Standards for 6-2 FTOH by LC/MS/MS 

(A) 

(B) 

(A): Before polymer analysis 

(B): After polymer analysis 
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Representative Calibration Curve for 8-2 FTOH by LC/MS/MS 

Note: All initial and final calibration standard injections included in calibration curve. 
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Representative Calibration Standards for 8-2 FTOH by LC/MS/MS 

(A) 

(B) 

(A): Before polymer analysis 

(B): After polymer analysis 
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Representative Calibration Curve for 10-2 FTOH by LC/MS/MS 

 

Note: All initial and final calibration standard injections included in calibration curve.
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Representative Calibration Standards for 10-2 FTOH by LC/MS/MS 

(A) 

(B) 

(A): Before polymer analysis 

(B): After polymer analysis 
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Appendix C 

Summary Data for Method Trials 1 Through 8 
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Trial 1 - Sludge and polymer background - 2 MTBE extractions 
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Trial 2 - Telomer alcohol fortified sludge - 2 MTBE extractions 
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Trial 3 - Mass-labeled telomer alcohol and polymer fortified sludge - 3 MTBE extractions 
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Trial 4 - Procedural blanks and post-spikes for previous trial 
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Trial 5 - Telomer alcohol fortified sludge - 5 MTBE extractions 
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Trial 6 - Influence of experimental variables on telomer alcohol procedural recoveries 
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Trial 7 - Telomer alcohol and lab-scaled synthesized A1 polymer fortified sludge - 5 MTBE 

extractions 
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Trial 8 - Telomer alcohol and lab-purified A1 polymer fortified sludge - 5 MTBE extractions 
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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 Recovere

d

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 Recovere

d

6-2 FTOH

8-2 FTOH

10-2 FTOH

Threshold
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Average FTOH Fortified Polymer #2 (WIL 9382) Recoveries 

(Background Subtracted)

0%

10%

20%

30%

40%

50%

60%

70%

80%

12345

Extraction Number

% Total Mass Recovere

d

6-2 FTOH

8-2 FTOH

10-2 FTOH

Threshold
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Appendix E 

Records of Sample, Stock, Standard and Reagent Preparation 
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