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MP! 

RESEARCH 

TSCA-HQ-2004-016, RCRA-HQ-2004-0016, TSCA-HQ-2005-5001 

SEP A Fluorotelomer-Based Product Characterization 

Subject: MP! Research Technical Progress Report 

l\/lay 22,2010 to June 25,2010 

1 Introduction *' 

This document presents the progress of the technical work for characterization of fluoroteiomerbased products and corresponding synthesized or purified polymers in support of the 

Biodegradation Testing Supplemental Environmental Project ("Biodegradation SEP"). This 

progress report is prepared pursuant to Characterization Laboratory Exhibit A: Scope of Wori<, 

Section 4f. This report desaibes the technical wori< performed from May 22, 2010 up to the week 

ending June 25, 2010. The following components of the Wori< Plan have been completed: 

Components 1, 2, 3, 5 and 6. 

2 Progress Summary 

The technical work consisted of method development outlined in Component 7 of the Wori< Plan. 

LC/MS/MS methods are being developed for the following analytes: 7-3 Fluorotelomer Acid, 8-2 

Fluorotelomer saturated Acid, 8-2 Fluorotelomer unsaturated Acid, Perfluorooctanoic Acid, 

Perfluorononanoic Acid, Perfluorodecanoic Acid and Perfluoroundecanoic Acid. 

GC/MS methods are being developed for the following analytes: 6-2 Fluorotelomer Alcohol, 8-2 

Fluorotelomer Alcohol, 1.0-2 Fluorotelomer Alcohol, 8-2 Fluorotelomer Ethene, 8-2 Fluorotelomer 

Iodide, 10-2 Fluorotelomer Iodide, Perfluorooctyl Iodide, Perfluorodecyl Iodide, 8-2 Fluorotelomer 

Acrylate, 7-2 Fluorotelomer iso-ethanol and PFOA telomer 8-2 ester. 

MP! Research has been infomried that the following non-commercially available standards that 

require synthesis are no longer required for this project: 2-H perfluorooctanoic acid, 7-3 

fluorotelomer unsaturated acid and 7-3 fluorotelomer unsaturated amide. Component 4 of the 

Wori< Plan will not be executed. 

The total method development time incurred for the period of time covered by this report was not 

tabulated at the time of this submission. It will be included in the next Technical Progress Report. 

MPI Research 06/30/2010 Technical Progress Report ^^^ ^ * ' ^ '* 
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3 Analysis by LC/MS/MS 

An HP1100 system interfaced to an Applied Biosystems API 4000 LC/MS/MS was used for the 

method development work. The chromatographic conditions for the following analytes were 

investigated: 

Analvtes 

8-2 Fluorotelomer saturated Acid 

8-2 Fluorotelomer unsaturated Acid 

7-3 Fluorotelomer Acid 

Perfluorooctanoic Acid 

Perfluorononanoic Acid 

Perfluorodecanoic Acid 

Perfluoroundecanoic Acid 

lUPAC name 

Decanoic 

acid,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,1 

0,10-heptadecafluoro2-decenoic 

acid,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10, 

10-hexadecafluoroacid,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10 

-pentadecafluoroPentadecafiuoroctanoic acid 

Perfluorononanoic acid 

Perfluorodecanoic acid 

Perfluoroundecanoic acid 

CAS# 

27854-31-5 

70887-84-2 

812-70^ 

335-67-1 

375-95-1 

335-76-2 

2058-94-8 

Two chromatographic systems were developed. An isocratic system for 8-2 fluorotelomer 

saturated acid and a gradient system for all the other compounds. Both systems utilize 

the same column and mobile phase which allows for a smooth transition between the two 

chromatographic systems. 

Quality control samples were prepared in Methyl-t-butyl ether (MTBE) to simulate samples. 

Both nitrogen evaporation (n-evap) and dilution techniques were investigated. Low 

recoveries were obtained with the nitrogen evaporation technique and this was most 

likely due to the volatility of the compounds. Sample dilution produced acceptable and 

reproducible results. The solubility of MTBE and the effects on the chromatographic 

conditions were also investigated. 

4 Analysis by GC/MS 

The analyses were performed on a Hewlett-Packard GC/MS system with positive chemical 

ionization using helium carrier gas and methane reagent gas. A HP-1 MS column was used for 

the development work for the following analytes: 

Analvtes 

6-2 Fluorotelomer Alcohol 

8-2 Fluorotelomer Alcohol 

10-2 Fluorotelomer Alcohol 

8-2 Fluorotelomer Ethene 

lUPAC name 

1 H,1 H,2H,2H-perfluorooctan-1-ol 

1H,1H,2H,2H-perfluorodecan-1-ol 

1 H,1 H,2H,2H-perfluorododecan-1-ol 

1 H,1 H,2H-perfluoro-1-decene 

CAS# 

647-42-7 

678-39-7 

865-86-1 

21652-58^ 

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8-2 Fluorotelomer Iodide 

10-2 Fluorotelomer Iodide 

Perfluorooctyl Iodide 

Perfluorodecyl Iodide 

8-2 Fluorotelomer Acrylate 

7-2 Fluorotelomer iso-ethanol 

PFOA telomer 8-2 ester 

1H,1H,2H,2H-perfluorodecyl iodide 

1H,1H,2H,2H-perfluorododecyl iodide 

Perfluorooctyl Iodide 

Perfluorodecyl Iodide 

2-propenoic acid, 

3,3,4,4,5,5,6.6,7,7,8,8.9,9,10,10,10-

heptadecafluorodecyl ester 

2-nonanol, 

3,3,4,4,5,5,6,6,7,7.8,8.9,9,9-

pentadecafluoroOctanoic acid, pentadecafluoro3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-

heptadecafluorodecyl ester 

2043-53-0 

2043-54-1 

507-63-1 

423-62-1 

27905-45-9 

24015-83-6 

Not 

Available 

10-2 Fluorotelomer Alcohol and 8-2 Fluorotelomer Iodide co-elute. Altemative instmment 

conditions were explored and better resolution between these two analytes was achieved. 

The secondary ions for 8-2 Fluorotelomer ethene exhibited weak intensity under the PCI mode. 

Alternative ionization mode. Negative Chemical Ionization, was explored. The intensities of the 

secondary ions are much better under NCI condition. The ions monitored under NCI are 406, 

386 and 426. 

The peak of 8-2 Fluorotelomer ethene is broad and un-symmetric. A DB-624 column (30m x 

0.25mm x 1.40pm) was used and resulted in much better peak shape. 

Due to the compatibility of PFOA telomere 8-2 ester with other analytes, it was prepared by itself 

at the following concentrations: 10. 20, 50, 100, 500 and lOOOng/mL and analyzed under PCI 

condition. A linear calibration curve was generated. It was show that the curve is linear from 10 

ng/mL to 500 ng/mL.. 

5 Attachments 

5.1 Appendix A: 

5.2 Appendix B: 

5.3 Appendix C: 

Raw Data (LC/MS/MS) 

Raw Data (GC/MS) 

Certificates of Analysis 

6 Signatures 

I certify under penalty of law that I have examined and am familiar with the infomriation submitted 

in this document and all attachments and that this document and its attachments were prepared 

either by me personally or under my direction for supervision in a manner designed to ensure that 

qualified and knowledgeable personnel property gather and present the infomnation contained 

therein. I further certify, based on my personal knowledge or on my inquiry of those individuals 

immediately responsible for obtaining the infomriation, that the information is true, accurate and 

complete. I am aware that there are significant penalties for submitting false information, including 

IVIPI Research 06/30/2010 Technical Progress Report PAGE 3 OF 4 
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the possibility of fines and imprisonment for knowingly and willfully submitting a materially false 

statement. 

&Mi^^ 

Xiang (Robert) Zhu, Study Director Date 

rviPI Research 06/30/2010 Technical Progress Report PAGE 4 OF 4