### p. 1 CBIC Control Number 

# OPPT CBIC Chemical " Corporation 2013OCT 18 PM 2= 14 asub~yaticcenomuK . 3676 Davis Road N

.W . " Dover, Ohio 44622 " (330) 343-7711 " 1-800-321-8805 " Fax: (330) 364-9626 

### September 25, 2013 Document Control Office (7407 M) Office of Pollution Prevention and Toxics (OPPT) Environmental Protection Agency EPA East Building, RoomE6428 (202-564-8930) 1201 Constitution Avenue, NW Washington, DC 20460 Attention: TSCA Section 4 Docket ID Number EPA-HQ-OPPT-2009-0112 ToWhom

It May Concern: Proposed Test Plan; Testing of Certain High Production Volume Chemicals; Third Group of Chemicals. Federal Register 76 (204), 65385-65410, October 21, 2011 . 1-Decene. sulfurized (CAS No . 72162-15-31 Dover Chemical Corporation submitted a test plan to be completed in three phases to satisfy the testing requirements of the subjecttest rule for 1-Decene, sulfurized (CAS # 72162-15-3) . The results of the Phase 1 study noted below are attached. Phase 1 Physical/Chemical Properties to Fulfill Testing Requirements A2 to 5 Boiling point: EC A

.2 / OECD 103/ OPPTS 830 .7220 Vapor Pressure: ASTM E 1782-08 (thermal analysis) N-Octanol/water partition coefficient (log 10 basis) or IogKoW by appropriate method as specified as MethodA, 40 CFR799.6755 (shake flask) ; Method B, ASTM E 1147-92 (reapproved 2005) (liquid chromatography) ; or Method C, 40 CFR799.6756 (generator column) . Atest to determinethe octanol/water partition coefficient is not required when the estimated log Kow (the log of the octanol/water partitioning coefficient) of the chemical is < 0 . 

# 356398 RECEIVED

Water solubility: By appropriate test method as specified as Method A, ASTM E 1148-02 (reapproved 2008) (shake flask) ; Method B, 40CFR 799 .6784 (shake flask) ; Method C, 40 CFR799.6784 (column elution) ; or Method D, 40CFR799 .6786 (generator column) .

# Chemical

" Corporation asuera .nawceenmsn~. 3676 Davis Road N

.W . " Dover, Ohio 44622 " (330) 343-7711 " 1-800-321-8805 " Fax: (330) 364-9626



### In addition, the ELCOCorporation, 100 Belt Line Street, Cleveland, Ohio 44109-2800, has applied for an exemption fromthe test rule requirements referenced above on the basis that the required testing for 1-Decene, sulfurized (CAS#72162-15-3) is being conducted by DoverChemical . The ELCOCorporation has agreed with Dover Chemical to pay a percentage of the testing costs incurred by Dover Chemical in conducting the testing. If you have any questions or comments, please contact me directly at 330-365-3610. Sincerely,

TimNowicki Manager Product Compliance Dover Chemical Corporation tnowickiP

.doverchem

.com

# FINAL REPORT

Studv Title 

## DETERMINATION OF PHYSICO-CHEMICAL PROPERTIES OF

1-DECENE, SULFURIZED " Validation of an analytical method " Boiling temperature " Vapour pressure " Watersolubility " Partition coefficient

Author K.A. Oudhoff, PhD

.

Test Facilitv WIL Research Europe B .V. Hambakenwetering 7 5231 DD's-Hertogenbosch The Netherlands Laboratorv Proiect Identification Project 502505 Substance 2047231A

- Page 1 of 32 -1-Decene, sulfurized Project 502505 

### 1 . CONTENTS 1 . CONTENTS . . . . . . . . . . . . . . . . .. . . . . .. .. .. .. .. .. .. . . . . . .. . . . . . . .. .. .. .. .. .. . . . . . .. . .. .. .. .. .. . . . . . .. . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .2 2. STATEMENT OF GLP COMPLIANCE .. . . . . . . . . . . . . . . . . . . . . . . . .. .. . . . . . . . .. . . . . . .. .. .. .. . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . .. . . . . . . .4 3 . QUALITYASSURANCESTATEMENT. . . . . . .. . . . . . . . . . . . . . . . . .. .. . . . . . . . . . . . . . . .. .. .. .. .. . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . .. . . . . . . .5 4 . SUMMARY.. .. .. .. .. .. .. .. .. .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . .. . . .. . . . . . . . . . . . . .. .. . . . . . . . . . . . . . . .. .. .. .. .. . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .6 5 . INTRODUCTION .. .. . . . . .. . . . . . . . . . . . . . . .. . . . . . . . .. . . . . . . . . . . . . . . .. .. . . . . . .. .. .. . . . . . .. . . . . . .. .. .. . . . . . . . . . . . . .. . . . . . . . . . . . . . . . .. .. .. . . . . . . . . .7 5 .1 . Preface . .. .. .. .. .. . . .. . . . . . . . .. . . . .. . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. .. .. .. . .. .. . . . . . .. .. .. .. . . . . . . . . . . .. . . . . . . . . . . . . . .. .. .. . . . . . . . . . . .7 5 .2. Aim

of thestudy.. . . . . . . . .. . . . . . . .. .. .. .. .. . . . . . . . . . . . . . . . . . . . . . . . .. .. .. .. .. . . .. . . . . .. .. .. .. . . . . . . . . . . .. . . . . . . . . . . . .. .. .. .. .. .. . . . . . . .7 5 .3. Storage and retention of records and materials . .. . . .. .. .. .. .. .. .. .. . . . . .. .. .. .. .. .. .. . . . . . .. .. .. .. .. . . . . . . . . . . . . . . .7 6 . MATERIALS.. .. .. .. .. .. .. .. .. . . . . . .. . . . . . . . . . . . . . . .. .. . . . . . .. .. .. . . . . . . . . . . . . .. .. .. . . . . . . . . . . . . .. .. .. .. .. .. .. . . . . .. . . . . . .. .. .. .. .. .. . . .. .. . . . . . . .8 6 .1 . Test substance . .. . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . .. .. .. .. .. . . .. . . . . .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. . . . . .. . . . . . .. .. .. .. .. .. .. .. . . . . . . . . .8 6 .2. Electronic data capture .. .. .. .. .. .. .. . . . . . . . .. .. .. .. . . .. .. . . . . .. .. .. .. .. .. .. .. .. .. . . . . . . .. .. .. .. .. .. . . . . . .. .. .. .. .. .. .. .. . . . . . . . . .8 6 .3. List of deviations . . . . . . .. .. .. .. .. .. .. . . . . .. . . . . . .. .. .. .. .. .. .. . . . . .. . . .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. . . . . . .. .. .. .. .. .. .. . . . . . . . . . . .8 7. VALIDATION OF AN ANALYTICAL METHOD . .. .. .. .. .. .. .. . . . . . . . . .. .. .. .. .. . . . . . . . . . . . . .. .. . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . .9 7.1 . Guidelines. . . . . .. .. .. . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . .. .. .. .. .. .. .. . . . . .. . . . . .. .. .. .. . . . . .. . . .. .. .. .. .. .. .. .. . . . . . .. .. .. .. . . .. . . .. .. . . . . . . .9 7.2. Reagents . . . . . . . . . . .. . . . . . .. .. . . .. .. .. .. .. .. .. . . . . . .. .. .. .. .. .. .. .. . . .. . . . . . . .. .. .. .. .. .. . . . . .. .. .. .. .. .. .. . . . . . .. .. .. .. . . . . . . . . .. . . . . . . .9 7.3 . Performance of the study . . . . . . . . . . . . . . . . . .. . . . . .. .. .. .. .. .. .. . . . . . . . . .. .. . . .. .. . . . . . . . . . . . . . . .. .. . . . . . .. .. .. . . . . . . . . . . . . . . . . . . .9 7.4 . Analytical method . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . . .. . . .. .. .. .. . . . . . . .. .. .. .. .. .. . . . . . .. .. . . . . . . . . . . . . . . . . . . 10 7.5. Formulas .. . . . . . . . . . . . . . . . . .. . . . . .. .. .. .. . . . . . . . . . . . .. . . .. .. .. .. .. .. .. .. . . . . . . .. .. .. .. .. .. . . . . . . . . .. .. .. .. .. . . . . . .. . . . . . . . . . . .. . . . . . . . .11 7.6. Results . . . .. . . . . . . . . . . . . . . . . .. .. .. .. .. .. . . . . . . . . . . . . . .. . . . . .. .. .. .. .. .. .. . . . . .. .. .. .. .. .. .. . . . . . . . . .. . . . . .. .. . . . . . .. . . . . . . . . . . .. . . . . . . . .12 7.7. Conclusion . . . . . . . . . . . . . . . .. . . . . . . .. .. . . . . . . . . . . . . . .. . . . . .. .. .. .. .. .. .. . . . . . . . . . . .. .. .. .. . . . . . . . . .. .. . . .. .. . . . . . .. . . . . . . . . . . . . . . . . . . . .14 7.8 . Figures . . . .. .. .. . . . . . . . . . . . . .. .. .. .. .. .. . . . . . . . . . . . . . .. . . . . . . .. .. .. .. .. .. . . . . .. .. .. .. .. .. .. . . . . . . . . .. .. .. . . . . . . . . . .. . . . . . . . . . . .. . . . . . . . .15 8 . BOILING TEMPERATURE .. . . . . . . . . . . . . . . . . . .. .. . . .. . . . . .. .. .. .. .. .. .. . . . . . . . . . . . . . . .. .. . . . . . .. . . . .. .. .. .. . . . . . .. . . . . . . . . . . . . . . . . . . . . 17 8 .1 . Guidelines .. . . . . . . . . . . . . . . .. . . . . . . .. .. . . . . . . . . . . . . . .. . . . . .. .. . . .. .. .. .. . . . . . . . . .. .. .. .. .. . . . . . . . . . . . . . . .. . . . . . . . .. . . . . . . . . . . . . . . . . . . . .17 8 .2. Performance of the test . . . . . . . . . . . . . . .. .. . . .. . . . . . . . . . . .. .. .. .. . . . . . . . . . . . . . . .. .. . . . . . .. .. .. . . . . . . . . . . . . .. . . . . . . . . . . . . . .. . . . . . 17 8.3. Analytical method . . . . .. . . . . . . . . . . . . . . . .. .. . . . . .. . . . . . . . . . . .. .. .. .. . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . .. . . . . . 17 8.4. Interpretation .. . . .. . . . . . . .. . . . . . .. . . . . . . . . . . . . . . . . .. . . . . . . . . . . .. .. .. .. . . . . . .. . . . . . .. .. .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . .. .. . . . . . 18 8.5. Results . . . .. .. .. .. .. .. . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . .. .. .. . . . . . . . . .. .. .. .. .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . .. . . . . . . . . .18 8.6. Conclusion . .. .. .. .. . . .. . . .. . . . . . .. . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . .. .. . . . . . .. . . . . . . . .. .. . . . . . .. . . . . . . . . . . . . . . . . .. . . . . . .. .. .. .. . . . . . . .18 8.7. Figures . . . .. .. .. .. .. .. .. .. .. .. . . . . . . . . . . . . . . . . . .. .. . . .. . . . . . . . . . . . . . . .. .. . . . . . . . . . . . . . . .. .. . . . . . .. . . . . . . . . . . . . . . . . .. . . . . . .. .. .. . . . . . . . . .19 9 . VAPOUR PRESSURE . .. .. .. .. . . . . . .. . . .. .. .. . . .. .. .. .. . . . . . . . . . . . . . . . . .. . . . . . .. .. .. . . . . . . . . . . . . .. .. .. . . . . . . . . . . . . .. . . . . . .. .. .. .. .. . . . . . 21 9 .1 . Guidelines .. .. .. .. .. .. .. .. .. . . . . . .. . . . . . . .. . . .. .. .. .. . . . . . . . . . . . . . . . . .. . . . . . .. .. . . . . . .. .. . . . . . .. .. .. .. .. . . . . . . . . .. . . . . . .. .. .. .. .. . . . . .21 9.2. Performance of the test . . .. .. .. .. .. .. . . . . .. .. . . . . . . . . . . . . . . . . .. . . . . . .. . . .. .. . . . . . . . . . . .. .. .. .. .. .. . . . . . . .. . . . . . .. .. .. .. .. . . . . . 21 9.3. Analytical method .. .. .. . . . . . .. .. .. .. . . . . .. .. .. .. . . . . . . . . . . . . . . . . .. . . . . . .. .. .. .. .. . . . . . . . . .. .. .. .. .. .. .. . . .. .. . . . . . .. .. .. .. .. . . . . . 21 9.4. Reference substances. . . . .. .. .. . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . .. .. .. .. .. .. . . . . . . .. . . .. .. .. .. .. .. .. .. . . . . . .. .. .. . . . . . . . . . 22 9.5. Interpretation . . .. .. .. .. .. .. . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . .. .. .. . . . . . . . . . . . . .. .. .. .. . . . . . . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . .. .. .. . . . . . . . . . 23 9.6. Results . . . .. . . . . . . . . .. .. .. .. .. . . . . . .. .. .. .. .. .. . . .. . . .. . . . . . .. .. .. . . . . . . . . . . . . .. .. . . .. . . . . . . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . .. .. . . .. .. . . . . .24 9.7. Conclusion . . . . . . . .. .. .. .. .. . . . . . .. .. .. .. .. . . . . . . .. .. . . . . . .. .. .. .. . . . . . . . . . . .. .. .. . . . . . . . . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . .. . . . . . . .. . . . . .24 9.8. Figures . . . .. . . . . . . . . .. .. .. .. .. . . . . . .. .. .. .. .. .. . . . . . . .. . . . . . .. .. .. .. . . . . . . . . . . .. .. .. .. .. . . . . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . .. . . . . .. .. . . . . .25 10 . WATERSOLUBILITY .. .. .. .. .. . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. .. .. .. . . . . . . . . . . .. .. .. .. .. .. . . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . .. . . . . . . . . . . . . . 26 10.1 . Guidelines . . . . . . . . .. . . . . . . .. . . . . . .. .. .. .. . . . . . . . . . . .. . . . . . .. .. .. .. . . . . . . . . . . .. .. .. .. .. . . . . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . .. . . . . .. .. . . . . .26 10.2. Reagents . . . . . . . . . . . .. . . . . .. . . . . . .. .. .. .. . . . . . . . . . . .. . . . . . .. .. .. .. . . . . . . . . . . .. .. .. .. .. . . . . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . .. . . . . .. .. . . . . . 26 10.3. Performance of the study . . . . . . . . . . . . . . . . . . . . . . . . .. .. .. .. . . . . . . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . . . . .. .. .. .. .. . . . . . .. . . . . . . . . . . . . . 26 10.4. Analytical method . . . . .. . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. .. .. .. . . . . . . . . . . .. . . . . .. .. .. .. .. . . .. .. .. .. .. .. .. .. .. .. . . . . . .. . . . . . . . . . . . . . 27 10.5. Interpretation . . . . . . . . . . . . . . . . . . . .. . . .. .. . . . . . . . . . . . . . . . . . .. .. .. .. .. .. . . . . . . .. . . . . .. .. .. . . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . .. . . . . . . . . . . . . . 28 10.6. Results. .. .. . . . . . . . . . . . . . . . . . . . . . . . .. .. .. . . . . . . . . . . . . . . . . . . . .. .. .. .. .. .. . . . . . . .. .. .. .. .. .. . . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . .. . . . . .. . . . . . . .29 10.7. Conclusion . . . . . . . . . . . . . . . . . . . . . . .. .. . . . . . . . . . . . . . . . . . . . . . .. .. .. .. .. .. . . . . . . .. . . .. .. .. .. .. .. . . .. . . .. .. .. .. .. .. .. .. . . . . . .. . . . . . . . . . . . . .30 11 . PARTITIONCOEFFICIENT. . . . . . .. . . . . . . . . . .. .. .. .. . . . . . . .. .. .. .. .. .. .. . . . . .. . . . . . . .. .. .. .. .. .. . . .. .. .. .. .. .. . . .. . . . . . .. . . . . . . . . . . . . . 31 11 .1 . Guidelines . . . . . . . . . . . . . . . . . . . . . . . .. .. . . . . . . . . . . . . . . . . . . . . . .. .. .. .. .. .. .. . . . . .. . . .. .. .. .. .. .. . . .. . . . . .. .. .. .. .. .. .. . . . . . .. . . . . . . . . . . . . .31 11 .2. Reagents . . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. .. .. .. .. .. .. .. . . .. .. .. .. .. .. .. .. . . .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . 31 11 .3. Performance of the study . . . . . . . . .. .. .. .. .. .. .. . . .. .. .. .. .. .. .. .. .. .. . . . . . . . . .. .. .. .. .. . . . . . . . . . . .. .. . . . . . . . . . .. . . . . . . . .. . . . . 31 11 .4. Results. .. .. . . . . . .. .. . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. . . .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. . . . . . . . . . . . . .. . . . . . . . . . .. . . . . . . . . . . . . .32 11 .5. Conclusion . . . . .. .. . . . . . . . . . . . . .. .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . .. .. .. .. .. . . .. . . .. .. .. .. .. .. .. .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . .. . . . . . .32



### Final report - Page 2 -1-Decene, sulfurized Project 502505 

### TABLES Table 1 Statistical parameters of the calibration curve. . . . . . . . .. . . . . . . . . . . . . .. .. .. . . . . . .. . . . . . . . . . . . . . . . . .. . . . . . .. .. . . . . 12 Table 2 Accuracysamples .. .. .. .. .. . . . . . . . . .. .. .. . . .. . . . . . . . . . . . . . . .. .. . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . . . . . . . . .12 Table 3 Stability of the analytical systemand end solutions .. . . . . . . . . .. . . . . . . . . . . . . . .. . . . . . . . . . . . . . . .. . . . . . . . .. .. . . . . 13 Table 4 Stored accuracy samples. . . . . . . . . .. .. .. .. . . . . . .. . . . . . . . . . .. . . . . . .. .. .. .. .. .. .. .. .. .. . . . . . .. . . .. .. .. .. .. .. .. .. . . . . . .. . . . . . . 13 Table 5 Results of the isothermal TGAanalysis .. .. .. .. . . . . . . . . . . .. . . . . .. .. .. .. .. .. .. . . . . . .. . . . . . . . . . . . . . . . . .. . . . . . .. . . . . . . 24 Table 6 Vapour pressure of thetest substance . .. .. .. .. . . . . . . . . . . .. . . .. .. .. .. .. .. .. .. . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. .. . . . . 24 Table 7 Main study-watersolubility of thetest substance . .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. .. . . . . 29 FIGURES Figure 1 GC-MS chromatogramof a 1 .20 mg/I test substance solution [res . id. 1888] . . . . . . . . . . .. .. . . . . 15 Figure 2 GC-MS chromatogramof the blank accuracy sample [res. id. 1921] . . . . . . . . . . . . . . . . . . . . . . . .. .. . . . . 15 Figure 3 GC-MS chromatogramin the full scan mode of a 50 mg/I test substance solution and a

blank n-hexane [inj . id. 1443 and 1450] . The MS spectrumof the compound at 8 .2 minutes is included. . . . . . . .. .. .. . . . . . . . . . . . . .. .. .. .. . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . .. . . . . . .. .. . . . . 15 Figure 4 Regression line: response of the test substance as a function of concentration [cal . curve

id . 1879] . . . . . .. . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . .. .. .. . . . . . .. .. .. .. . . .. . . . . . . .. . . .. .. .. .. .. .. .. .. . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . 16 Figure 5 TGAcurve of thetest substance. . . . . . . . . . . .. . . .. .. .. .. .. . . . . .. . . . . . . . . .. . . . . . . . . . . . . . .. . . . . . . . .. . . .. . . . . . . . . . . .. .. . . . . 19 Figure 6 DSCcurve of the test substance obtained with Experiment 1 . . . . . . . . . .. . . . . . . . .. . . . . . . . . . . . . . . .. .. . . . . 19 Figure 7 DSCcurve of the test substance obtained with Experiment 2. . . . . . . . . .. . . . . . . . . . . . . . . . . .. . . . . . .. .. . . . . 20 Figure 8 DSCcurve of the test substance obtained with Experiment 3. . . . . . . . . .. . . . . . . . . . . . . . . . . .. . . . . . .. .. . . . . 20 Figure 9 Weight loss curve ofthe test substance. .. .. .. .. .. .. .. .. .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. .. . . . . 25 Figure 10 Plot of log PT of thetest substance versus 1/T. .. .. .. .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . .. . . . . . . . . . . . . . . .. .. . . . . 25

Final report - Page 3 -

### 1-Decene, sulfurized Project 502505 2 . STATEMENT OF GLP COMPLIANCE WIL Research Europe B.V.,'s-Hertogenbosch, The Netherlands Thestudy described in this report has been correctly reported and was conducted in compliance with: 

### The Organization for Economic Co-operation and Development (OECD), OECDPrinciples on Good Laboratory Practice(GLP) (as revised in 1997),ENVIMC/CHEM(98) 17 . The sponsor is responsible for Good Laboratory Practice (GLP) compliance for all test substance Information unless determined by WIL Research Europe. WIL Research Europe B.V. E. Baltussen, PhD

. K .A . Oudhoff, PhD

. Section Head Study Director Analyk'cal & Physical

Date: .(J .~. . 

### Date: . .. . 13. . .&--:P .A.encite.'. . .ZC? 1 .~

. . . . .

Final report - Page 4-

### 1-Decene, sulfurized Project 502505 3. QUALITY ASSURANCE STATEMENT WIL Research Europe B

.V ., 's-Hertogenbosch, The Netherlands This report was inspected by the WIL Research Europe Quality Assurance Unit (QAU) toconfirmthat the methods and results accurately and completely reflect the rawdata. During the on-site process inspections, procedures applicable to this type of study were inspected. The dates of Quality Assurance inspections are given below . Start End Type of Inspection Inspection Reporting Inspections Phase/Process date date date Study Protocol 28-May-2013 28-May-2013 28-May-2013

Protocol Amendment 01 22-Aug-2013 22-Aug-2013 22-Aug-2013 Report 30-Aug-2013 30-Aug-2013 30-Aug-2013 

### Process Analytical and physical chemistry 13-May-2013 21-May-2013 27-May-2013

Test Substance Handling Observations/Measurements WIL Research Europe B .V . C .J . Mitchell, BSc

. 

### Head of Quality Assurance



### Date: . . . .. . ~. .. . . . . . . . . . . . .. . . .. .

Final report - Page 5 -1-Decene, sulfurized Project 502505 4 . SUMMARY The results of the physico-chemical properties of thetest substance aregiven below . 

### Parameter Guideline(s) Result Comment Analytical method Sanco 3029 successfully validated Boiling temperature ECA.2 no boiling temperature reaction and/or OECD 103 decomposition of the OPPTS 830

.7220 test substance at 

### > 200°C (> 473K) was observed Vapour pressure EC A .4 20°C 1 .8 x 10"2 Pa = isothermal TGA OECD 104 1 .3 x 10'° mmHg effusion method OPPTS 830

.7950 250C 2

.7 x 10"2 Pa = 

### 2.Ox10'°mmHg Water solubility ECA.6 5 10 Ng/I at 20°C by the OECD 105 column elution OPPTS 830

.7840 method Partition coefficient EC A .8 log P. : > 8 .0 at 20°C by the OECD 107 estimation method

Final report - Page 6-1-Decene, sulfurized Project 502505 

### 5. INTRODUCTION 5.1 . Preface Sponsor Dover Chemical Corporation 3676 Davis Road N

.W . Dover, Ohio 44622 USA 

### Study Monitor Mr. P. Leber Test Facility WIL Research Europe B .V. Hambakenwetering 7 5231 DD's-Hertogenbosch The Netherlands Study Director K.A . Oudhoff, PhD

. Study Plan Start : 31 May 2013 Completion : 26July 2013 5 .2. Aimof the study The aimof the study was to determinethefollowing physico-chemical properties for 1-Decene, sulfurized: Validation of an analytical method Boiling temperature Vapour pressure Water solubility Partition coefficient 5 .3. Storage and retention of records and materials Records and materials pertaining to thestudy including protocol, raw data, specimens (except specimens requiring refrigeration or freezing) and thefinal report are retained in the WIL Research Europe archives for a period of at least 2 years after finalization of the report. After this period, the sponsorwill be contacted to determine how the records and materials should be handled. W IL Research Europe will retain information concerning decisions made. Those specimens requiring refrigeration or freezing will be retained by W IL Research Europe for as long as thequality of thespecimens permits evaluation but no longer than three months after finalization of the report. W IL Research Europe will retain a test substance sample until the expiry date, but no longer than 10 years after finalization of the report . After this period the sample will be destroyed.

Final report - Page 7-1-Decene, sulfurized 

### 6. MATERIALS 6 .1 . Test substance 6 .1 .1 . Test substance information Identification Molecularformula Molecularweight CAS Number Description Batch Content Test substance storage Stability under storage conditions Expiry date 1-Decene, sulfurized CxH % 315-1000+ 72162-15-3 Dark brown liquid S31173 37.6% Sulfur At roomtemperature in the dark Stable 13 September 2013 6 .1 .2. Studyspecific test substance Information Purity/composition correction factor Reactivity 

### Test substance handling 6 .2 . Electronic data capture No Reactive to moisture Well-sealed container Project 502505

Systemcontrol, data acquisition and data processing were performed using thefollowing programmes: - Advantage Integrity Software version 3.0 (TA Instruments, New Castle, DE, USA) - Empowerversion 7.00 (Waters, Milford, MA, USA) - Enhanced Chemstation version D .00.01 .27 (Agilent Technologies, Wilmington, DE, USA) Temperature, relative humidity and/or atmospheric pressure during sample storage and/or performance of the studies was monitored continuously using the following programme: - REES Centron Environmental Monitoring systemversion SQL 2.0 (REES Scientific, Trenton, NJ, USA) 6.3 . List of deviations 6.3 .1 . List of protocol deviations 

### There were no deviations fromthe protocol . 6.3.2. List of standard operating procedures deviations Any deviations fromstandard operating procedures (SOPs) were evaluated and filed in the studyfile. There were no deviations fromSOPs that affected the integrity of the study.

Final report - Page 8 -1-Decene, sulfurized Project 502505 

### 7. VALIDATION OF ANANALYTICAL METHOD 7.1 . Guidelines 

### The study was based on the following guideline: European Commission: Guidance for Generating and Reporting Methods of Analysis in Support of Pre-registration Data Requirements forAnnex II (Part A, section 4) and Annex III (Part A, section 5) of Directive 91/414, SANCO/3029/99 rev. 4 (11/07/00) . 7.2 . Reagents 

### Water Tapwater purified by a Milli-Qwater purification system (Millipore, Bedford, MA, USA) n-Hexane Merck, Dannstadt, Germany Tetrahydrofuran (THF) VWRInternational, Leuven, Belgium All reagents were of analytical grade, unless specified otherwise. 7.3. Performance of the study Agas chromatographic method with mass spectrometric detection (GC-MS)for the quantitative analysis of the test substance in waterwas developed. Validation of theanalytical method was performed for the following parameters: Specific Atest substancesolution and blankaccuracy sample were analysed by single injection. The analytical method was found to be specific ifthe blank chromatogramshowed no response for the test substance or a response of < 30% of the limit of quantification. Calibration curve Calibration solutions were analysed in duplicate. The response of the calibration solutions was correlated with concentration using regression analysis with a 1/concentration2 weighting factor. A calibration curvewith a coefficient of correlation (r) of > 0 .99 and back calculated accuracies of the calibration solutions in the range 85-115% was accepted. Accuracy and repeatability 

### Accuracy samples were analysed by single injection into the analytical system . The analytical method was considered applicable for the determination of the test substance ifthe mean accuracy was in the range 70-110%and the coefficient of variation was 5 20% . Limit of auantification The limit of quantification (LOQ) is defined as the lowest concentration level at which an accuracy in the range 70-110%and a repeatability of 5 20% is demonstrated. The LOQ was obtained fromthe data of the accuracy- and repeatability test . Stability of theanalytical systemand end solutions Calibration solutions were injected throughout the validation sequence including the beginning and end. The analytical systemand/or end solutionswere found to be stable ifthe coefficient of variation on the responses of the solutions was:5 20% . Stability of stock solutions Stock solutions of the test substance were stored at roomtemperature for at least 12 hours. Additional calibration solutions were prepared and analysed by single injection. Thestock solutionswere found to be stable if thecoefficient of variation on the response factors of the calibration solutions prepared with fresh and stored stock solutions was 510% . Final report - Page 9 -

### 1-Decene, sulfurized Project 502505 Storage stability of samples Additional accuracy samples were prepared and stored in thefreezer (s -15°C) for at least 16 hours. On theday of analysis, the samples were defrosted at roomtemperatureand treated identically as freshly analysed accuracy samples. Thestored samples were found to be stable if the mean accuracy was in the range 70-110% . 7.4. Analytical method 7.4.1 . Analytical conditions Instrument Injector Detector 

### Column Carrier gas Carrier gasflow Injection PTV Mode Splitless time Split flow Gas saver Injection volume PTVtemperature program Initial temperature Initial time Rate Final temperature Hold time Oven temperature program Initial temperature Initial time Rate Final temperature Hold time MS Detection lonisation source 

### MS interface temperature Solvent delay Quantitation 7.4 .2. Preparation of solutions Gaschromatograph 6890N (Agilent Technologies, Palo Alto, CA, USA) CombiPal (CTC analytics, Zwingen, Switzerland) Mass selective detector (MSD) 5973N (Agilent Technologies) DB-5MS; 25 m

x 250 pm

i .d., df = 0

.25 pm (J&W Scientific, Folsom, CA, USA) Helium 1 ml/min (constant flow) Programmed temperature vaporizer (PTV) Splitless 60 sec 50 ml/min Off 1 PI 62°C 0 .01 min 720°C/min 300°C 5 min 60°C 1 min 25°C/min 300°C 2 min El* 280°C 3 min 

### m/z 236 amu Stock and spiking solutions Stock solutions of thetest substancewere prepared in n-hexane at concentrations of 1045 - 1125 mg/I . 

### Spiking solutions of the test substance were prepared in THF at concentrations of 7.49 - 1060 mg/I . Calibration solutions Six calibration solutions in the concentration range of 0 .04 - 6mg/1 were prepared fromtwo stock solutions. The end solution of the calibration solutions was n-hexane. Final report - Page 10 -1-Decene, sulfurized Project 502505 

### Accuracy samples 7 .5 ml waterwas spiked with thetest substance at a target concentration of 0 .01 and 1 mg/I . The accuracy samples were extracted in a 5:1 (v:v) ratio with n-hexane. Theshaking time was 30 seconds. The n-hexane layer was analysed. 

### The blank accuracy sample was prepared and treated similarly to the accuracy samples. 7 .5. Formulas Response (R) Peak area of thetest substance [units] Response factor (Rf) Rr = R CN where : CN = nominal concentration [mg/1] Calibration curve R=a C N +b CN +c where: a = quadratic regression factor [units x (I/mg)2] b = linear regression factor [units x I/mg] c = intercept [units] Analvsedconcentration (Ce) C. = -b42 -4ax(c-R) xd where: 2a d = dilution factor Accuracy CA x100 [%] N

Final report - Page 11 -

### 1-Decene, sulfurized Project 502505 7.6 . Results 7.6 .1 . Specificity Chromatograms of a test substance solution and the blank accuracy sample are shown in Figure 1 and Figure 2, respectively. The chromatogramof thetest substance solution showed a major test substance peak at a retention time of 8 .2 minutes. The area of this peak was used as response in the calculations. It was considered that the compound was representative for the test substance. The chromatogramof the blank sample showed no peak at the retention time of the test substance. Since no interferences were detected, the specificity requirements were met and the analytical method wasfound to be specific for the test substance. Note: The compound at 8 .2 minutes was selected based on full scan GC-MSforthe test substance during method development (data is archived in the raw data) . Figure 3 shows chromatograms of a test substance solution and a corresponding blank. The test substance is a mixture of multiple components. The component al 8 .2 minutes was detected at m/z236 amu (see MS spectrumadded lo Figure 3) . 7 .6.2. Calibration curve The calibration line was constructed using all data points.Figure 4 illustrates the calibration curve and Table 1 shows the statistical parameters. There was a quadratic relationship between response and test substance concentration in the range of 0 .0401 - 6

.08 mg/I (in end solution) . Since thecoefficient of correlation (r) was > 0 .99 and the back calculated accuracies ofthe data points were in the range 85-115%the calibration line was accepted. Table 1 Statistical parameters of the calibration curve

Quadratic regression factor Linear regression factor Intercept Weightingfactor r 4 .36 x 107 8 .11 x 10s -9 .61 x 10' 1/concentrationZ 0 .997

7 .6 .3. Accuracy and repeatability The results of the accuracy samples are given in Table 2 . Since the mean accuracy at each concentration level fell in the criterion 70-110%and the coefficient of variation was :5 20% the analytical method was accepted for the analysis of the test substance in water in thetarget concentration range of 0 .01 -1 mg/I . 

### Table 2 Accuracy samples Target concentration [m g/11 Nominal

concentration m/I 

### Analysed

concentration [m g /11 Accuracy

% Mean

accuracy % Coefficient of

variation % 

### 0 .01 0.0100 0 .00594 59 1 0.0100 0

.00886 89 87 2.0 0.0100 0

.00873 87 0.0100 0

.00845 85 

### 0.0100 0.00877 88

Final report - Page 12 -

### 1-Decene, sulfurized Project 502505 Table 2 Continued Target concentration [m g/11 Nominal

concentration m/I Analysed

concentration [m g/11 Accuracy



### % Mean

accuracy % Coefficient of

variation °/u 

### 1 1 .00 0.965 97 92 13

1 .00 0

.864 86 

### 1 .00 0.961 96 1 .00 0.741 74 1 .00 1 .06 106 Outlier according to the Dixon's Q-test at 95% confidence level . 7.8.4 . Limit of quantification The limit of quantification (LOQ) was assessed at 0 .01 mg/I in water. 

### 7.6.5 . Stability of the analytical systemand end solutions The results of the stability of the analytical systemand end solutions are given in Table 3 . Since the coefficient of variation at both concentration levels was 5 20% the analytical systemand end solutions were stable over at least a 18.25 hour time interval . Table 3 Stability of the analytical systemand endsolutions Nominal concentration [m g/11 Elapsed time hours Coefficient of variation % 0 .0401 20.27 7.8 (n=8) 1 .20 18.25 4 .5 (n=8) 7.6.6. Stability of stock solutions The coefficient of variation on the response factors of thecalibration solutions prepared with fresh and stored stock solutions was 2.4% . Since the value was 510%the stocksolutions were stable when stored at roomtemperaturefor at least 18 days. 7.6.7. Storage stability of samples The results of the storage stability of thetest substance in thefreezer aregiven in Table 4 . Since the mean accuracy of thefrozen samples fell in the criterion 70-110%the samples were stable when stored in thefreezer. Table 4 Stored accuracy samples Target concentration [ m g /1 1 Nominal

concentration [m g/11 Analysed

concentration m /I Accuracy

% Mean accuracy

% 

### 0.01 0.0100 0.00813 81 84

0.0100 0.00862 86 

### 1 1 .00 0.896 90 92

1 .00 0

.953 95

Final report - Page 13 -

### 1-Decene, sulfurized 7.7. Conclusion Theanalytical method wasvalidated for thefollowing parameters: Specificity Calibration curve Accuracy Repeatability Limit of quantification Stability analytical systemand end solutions Stability stock solutions Storage stability specific r = 0 .997 87 and 92% 2.0 and 13% 0 .01 mg/I stable stable stable Project 502505



### Final report - Page 14 -1-Decene, sulfurized Project 502505 7.8. Figures 

### Note: the time scale of Figure 3 is different fromFigure 1 and Figure 2.

Figure 1 GC-MS chromatogramof a 1 .20 mg/I test substancesolution [res. Id. 1888] .

iG'S'J"'u'iG'1Y"4Y'iL'IL'W'lY'4'a 'u -m'u Ys bS Figure 2 GC-MS chromatogramof the blankaccuracy sample [res. Id. 1921] . _q- - , m

. .W . -

Figure 3 GC-MS chromatogramin the full scan mode of a 50 mgll test substance solution

and a blank n-hexane [inj . id. 1443 and 1450] . The MS spectrumof the compound at 8.2 minutes is included. Final report - Page 15 -

### 1-Decene, sulfurized Project 502505

Figure 4 Regression line: response of the test substance as afunction of concentration [cal .

curve id. 1879] .



### Final report - Page 16 -1-Decene, sulfurized Project 502505 

### 8 . BOILING TEMPERATURE 8 .1 . Guidelines European Community (EC), EC no . 440/2008, Part A

: Methods for the Determination of PhysicoChemical Properties, Guideline A .2: "Boiling Temperature", Official Journal of the European Union no. L142, May 31, 2008. Organization for Economic Co-operation and Development (OECD), OECD Guidelines for theTesting of Chemicals no. 103

: "Boiling Point", July 27, 1995. United States Environmental Protection Agency (EPA), Product Properties Test Guidelines no. OPPTS 830

.7220 : "Boiling Point/Boiling Range", August 1996. 8.2 . Performance of thetest The boiling temperature of the test substance wasdetermined using differential scanning calorimetry (DSC) . This technique records the difference in heat flowof two crucibles, onefilled with test substance and the other left empty as reference, while these crucibles are subjected to a controlled temperature programme . When the test substance undergoes atransition, such as evaporation, is indicated by a deviation from the base line of the heat-flowrecord. Because evaporation is a process in which heat is consumed, for this process the deviation fromthe base line is in the endothermic direction. The boiling temperature (if any) of thetest substance is evaluated fromthe DSC curveas the extrapolated onset temperature of the endothermic evaporation peak. As a safety precaution for the DSCcell a preliminary test was performed using a thermogravimetricanalyzer (TGA) . 

### 8.2.1 . Preliminary test 8.15 mg test substance was heated at a rate of 20°C/minutefrom25°Cto 295°C . At this point 70% weight loss of thetest substance was observed. After the experiment, the sample was cooled to and equilibrated at 50°C and the consistency of thetest substance was determined. 8.2.2. Main study An overviewof the experimental conditions of the main study is given below . Experiment 1 2 3 Sample amount (mg) 6 .06 5 .41 6.40 Initial temperature (°C) 25 25 25 Rate (°C/minute) 20 20 20 End temperature (°C) 275 400 400 The experiments were performed under a flowof nitrogen and at atmospheric pressure . 8.3. Analytical method Preliminary test Instrument Q50thermogravimetricanalyzer (TGA) (TA Instruments, New Castle, DE, USA) Sample container aluminium ; closed with a lid in which a small hole was drilled

Final report - Page 17-1-Decene, sulfurized Project 502505 

### Main studv Instrument Q100 differential scanning calorimeter (TA Instruments) Sample container aluminium ; closed (Experiment 3) or closed with a lid in which a small hole was drilled (Experiment 1 and Experiment 2) 

### Reference empty sample container 8.4. Interpretation The standard boiling temperature is defined as the temperature at which the vapour pressure of a liquid is the same as the standard pressure (1013.25 hPa) . 8.5. Results 8.5.1 . Preliminary test The TGA-curve of the test substance is shown in Figure 5 . From250°C upwards the weight of the sample decreased significantly . At 275°Cthe sample weight had decreased by 25% . After the experiment, a black residuewas observed on the lid of the sample container and a dark brown residue remained in the sample container (original colour: dark brown) . The black residue on the lid of the sample container indicated reaction and/or decomposition ofthetest substance. 8.5.2. Main study The DSC-curve obtained with Experiment 1 is shown in Figure 6 . An endothermic peak was observed starting at 200°C

. The effect was most likely obtained due to reaction and/or decomposition ofthe test substance. After the experiment, a dark red residue remained in the sample container. To investigate the endothermic peak a higher end temperature was applied in the Experiment 2 . Figure 7 shows the DSC-curves obtained. An exothermic peak was observed between 200°Cand 325°C . The extrapolated onset temperatureof the peak was 257.06°C . Theeffect was most likely obtained dueto reaction and/or decomposition of the test substance . After the experiment, a dark brown residue remained in the sample container. To further investigate the endothermic peak a closed sample container wasapplied. Figure 8shows the DSC-curve obtained. The extrapolated onset temperature of the peak was 258.09°C . Since the endothermic peak did not shift to higher temperatures it demonstrated that reaction and/or 

### decomposition of the test substance was the reason for the endothermic effect . After the experiment, a dark brown residue remained in the sample container. 8 .6. Conclusion The boiling temperature of 1-Decene, sulfurized was investigated using DSC . Reaction and/or decomposition of thetest substance was observed at temperatures of > 200°C (>473K) . Boiling of the test substancewas not observed below the temperatureat which reaction and/or decomposition started. Based on this, the test substance has no boiling temperature.

Final report - Page 18-

### 1-Decene, sulfurized Project 502505 8.7. Figures

e 60 120

100

t D4 .61C70 .00%tam 20- FIB. NDT0X20101369994882

+ T792TC2500%I+cs

150 e(° Figure 5 TGAcurve of the test substance .

-15-1- 0 300 UAamIV0

.7ATAIreNmmb

Rio : NDT0X20101369995464

gmy, T-P-b- M ~IV47ATAIMV,Me Figure 6 DSC curve of the test substance obtained with Experiment 1 .

Final report - Page 19 -1-Decene, sulfurized Project 502505

10

~6 -10 ¢

-p

eoy, RIe:N0T0%E0101370004385

P5708°C

1E0 . . . A . . .260 . . . ,~ . . . ,~ . 460 TaTperall" CC) ~rvavATAImmm .rln Figure 7 DSCcurve of the test substance obtained with Experiment 2 . FIe :ND'r0%20101370004452

I~~

- ¢

.25 0 50 100 150 200 250 300 3rA 400 ~L~p TWTMWMI^Q UYwuIVO>ATAIMViab Figure 8 DSCcurve of the test substance obtained with Experiment 3 .

Final report - Page 20 -1-Decene, sulfurized Project 502505 

### 9 . VAPOUR PRESSURE 9 .1 . Guidelines European Community (EC), EC no. 761/2009, Part A : Methods for the Determination of PhysicoChemical Properties, GuidelineA .4: "Vapour Pressure", Official Journal of the European Union no . L220,August 24,2009 . Organization for Economic Co-operation and Development (OECD), OECD Guidelines for theTesting of Chemicals no.104: "Vapour Pressure", March 23, 2006 . United States Environmental Protection Agency (EPA), Product Properties Test Guidelines no . OPPTS830

.7950 : "Vapor pressure", August 1996. 9 .2 . Performance of the test Thevapour pressure ofthe test substance (PT) was determined by the isothermal thermogravimetric effusion method . The method is validated in the range 10"8 -103 Pa using a set offive reference substances with known vapour pressures (see paragraph 9.4) . The validity of the method was verified maximum

one month before this study using hexachlorobenzene as referencecontrol substance . The logarithmof the evaporation rate at 20°C (log vT, Zo) deviated < 10% from the average valueobtained during thevalidation test. Fromthis, it was possible to apply theconstants obtained with the validation test for the determination of the vapour pressure of thetest substance. An amount of 9

.89 and 11 .7 mg ofthe test substance was applied to the surface of a roughened glass plate as a homogeneous layer. Start temperature Isothermal intervals Increment steps End temperature 

### 100°C 10 minutes 10°C 200°C The weight loss of thetest substance was measured continuously as a function of time at defined isothermal temperatures. The evaporation rate of thetest substance (vT) was calculated from the weight loss of thecompound. The PT values at the defined isothermal temperatures were determined using the vapour pressure equation with the constants cand d specific for the experimental arrangement. Linear regression analysis of the log PT values and 1lT was performed using a least squares method. The PT values of thetest substance at 20°C and 25°C were determined using the vapour pressure regression curve . 9 .3 . Analytical method Instrument Q50thermogravimetric analyzer (TGA) (TA Instruments, New Castle, DE, USA) Surface of theglass plate 0 .50 cmZ The experiments were performed under a flowof nitrogen and at atmospheric pressure.

Final report - Page 21 -

### 1-Decene, sulfurized Project 502505 9 .4 . Reference substances Validation ofthe method is performed at least once every year (project 502186) . Each reference substance was measured in duplicate by TGAusing a temperature programthat was specific for thesubstance . Plots of log vT obtained at elevated temperatures and 1!Twere inter- or extrapolated to determine the log vT values at 20°C (log vT,zo)

. The log vT,zo values were plotted against the logarithmofthe vapour pressure at 20°C in Pascal units (log PT, Zo)

. Linear regression analysis usingthe least squares method yielded an equation of log PT,2o = 1 .05 x log vT,2o + 4 .32. The coefficient of correlation (r) was > 0 .99. The constants cand dspecific for theexperimental arrangementwere 1 .05 and 4 .32, respectively. Reference substance Reference PT values 20°C Pa mmH Corresponding PT values 25°C pa mmH 

### Literature Benzo(ghi)perylene 1 .33 x 10"8 1 .00 x 10-'0 1 .52 x 10'a" 1 .14 x 10-'e° 1 

### Chrysene 8.40 x 10"' 6 .30 x 10"a 2.18 x 10"8° 1 .64 x 10'8" 2 Hexachlorobenzene 1 .47 x 10"3 1 .10x 10'5 1 .01 x 104 7 .57 x 10"5" 1 Naphthalene 7.56 x 100 5 .67 x 10"2 1 .15 x 10' 8 .61 x 10-2 3 Water 2.34 x 103 1 .75 x 10' 3 .17 x 10s 2.38 x 10' 3 " Detennined by the vapour pressure regression curve of the validation study. No literature value ms available. 9 . Verschueren, K., Handbook of environmental data on organic chemicals, 4" edition, Wiley Chemistry 2. Borges, H.T., Formal toxicity summary for Chrysene, The Risk Assessment Information System(RAIS), 1994 3. Lide, D.R., CRC Handbook of Chemistry and Physics, 79" edition, CRCPress LLC., Boca Raton, FL, USA, 1998 4- 2- 0- -2 - a -4 - -6 - -8 - -10 , i i r -14 -12 -10 -8 -6 -4 -2 log VT,2o

Final report - Page 22 -1-Decene, sulfurized Project 502505 9 .5. Interpretation 9 .5.1 . Specifications The vapour pressure is a function of the temperatureand is specified in Pascal (Pa) or in mmHg. 9 .5 .2. Formulas Evaporation rate (vT) VT = 4m [g/cm2/h] F t where: Am = weight loss of the test substance [g] F = surface of thesample plate [cmZ] t = elapsed time for the weight loss [h] Vapour pressure equation log PT = c IogvT + d where: c = constant specific for theexperimental arrangement d = constant specific for theexperimental arrangement 

### Vapour pressure regression curve log PT = a 1/T+b where: T = temperature [K] a = slope [K] b = intercept

Final report - Page 23 -1-Decene, sulfurized Project 502505 

### 9.8 . Results Arepresentative weight loss curve ofthe test substance is shown in Figure 9 . The results of the isothermal TGAanalysis for the test substance and the vapour pressure at 20°C and 25°C are given in Table 5 and Table 6

. The plot of the log PT of thetest substance as function of the reciprocal temperatures is shown in Figure 10. Theequation of the curve was: 109 PT,ZO =-3282 x 1/T + 9 .44 (r = 0 .992, n = 8) . Table 5 Results of the Isothermal TGAanalysis Temperature °C Weight loss

/min vT

/cmZ/h log vT log PT PT Pa 110 5.078 6 .06 x 10-0 -3.22 0 .93 8

.5 x 100 4.218 5

.03 x 10" -3.30 0 .85 7.0 x 10° 

### 120 7.453 8.90 x 10-0 -3.05 1 .11 1 .3 x 10'

6.675 7.97 x 10-0 -3.10 1 .06 1 .1 x 10, 

### 130 11 .56 1 .38 x 10'3 -2.86 1 .31 2.0 x 101

10 .79 1 .29 x 10-' -2.89 1 .28 1 .9 x 10, 140 18

.39 2

.20 x 103 -2.66 1 .52 3.3 x 101 17.71 2

.11 x 10-3 -2.67 1 .50 3.2 x 101 Table 6 Vapour pressure of the test substance Temperature l oci log PT PT [ Pal PT [mmH gj 20 -1 .75 1 .8 x 10-2 1 .3 x 104 25 -1 .57 2 .7 x 10"2 2 .0 x 10'°

9 .7. Conclusion The isothermal TGAeffusion method was applied for the determination of thevapour pressure of 1-Decene, sulfurized. The vapour pressure ofthe test substanceat 20°C (293K) and 25°C (298K) was : 

### 20°C 25°C Pa mmH Pa mmH Test substance 1 .8 x 10-2 1 .3 x 10'° 2 .7 x 10-z 2

.0 x 10'

Final report - Page 24 -

### 1-Decene, sulfurized Project 502505 9 .8. Figures R1e:N0T0k20101370265757

Figure 9 Weight loss curve of the test substance. 1 .6 - 1 .4 - 1 .2 - 1- F ~ 0 .8 0 .6 0 .4 0 .2 

### 0 0 .0024 0.00245 0 .0025 0

.00255 0.0026 0 .00265 1/T [K-11 Figure 10 Plot of log P7 of the test substance versus 1/T .

Final report - Page 25 -1-Decene, sulfurized Project 502505 

### 10 . WATER SOLUBILITY 10.1 . Guidelines European Community (EC), EC no. 440/2008, Part A : Methods for the Determination of PhysicoChemic .al Properties, GuidelineA .6: "Water Solubility", Official Journal of the European Union no. L142, May 31, 2008. Organization for Economic Co-operation and Development (OECD), OECD Guidelines for the Testing of Chemicals no

. 105 : "Water Solubility", July 27, 1995. United States Environmental Protection Agency (EPA), Product Properties Test Guidelines no. OPPTS 830

.7840: "Water Solubility: Column Elution Method; Shake Flask Method", March 1998. 10.2. Reagents 

### Double distilled water Waldeck, Miinster-Roxel, Germany n-Hexane Merck, Dannstadt, Germany All reagents were of analytical grade, unless specified otherwise . 10.3. Performance of the study Two methods are available for the determination of thewater solubility of a test substance: 1 . Column elution method The method is based on the elution of the test substancewith waterfroma column which is charged with an inert support material, such as bare silica particles, coated with an excess of thetest substance. It can be applied to test substances with a water solubility of < 10-Z g/I . 2. Flask method The mass concentration ofthetest substance in aqueous solutions saturated with the test substance will be determined after stirring or shaking at a specific temperature for a specific period of time. The method can be used for test substances with a water solubility of t 10~2 g/I . Apreliminary test was carried out as a range-finding test prior to performance of thecolumn elution method or flask method. Preliminary test Test substancewas stirred with double distilled water at a nominal concentration of 103 mg/I at 19.8 t 0 .2°C for 19 hours. After stirring, the water phasewas centrifuged, treated and analysed. In the preliminary test the water solubility of thetest substancewas < 10'Z g/I . Therefore, the column elution method was chosen for the main study. 

### Main studv Asolution with an absolute test substance quantity of 76 .2 mg was prepared in n-hexane. The solution was mixed with 5.5 g LiChroprep Si 60 25-40 umcolumn material (Merck, Darmstadt, Germany) . The n-hexane was completely evaporated at 45°C using a rotary evaporator. The loaded carrier material was stored overnight at roomtemperature. A 150 mmx 4.6 mm

i .d. column was filled with the carrier material and 0.5 um frits were used to enclose the column. Double distilled water was pumped through the column until it was completely filled. The systemwas allowed to equilibrate for two hours. After the equilibration period, the column was eluted overnight with double distilled water at a flowrate of 12 ml/hour.

Final report - Page 26 -

### 1-Decene, sulfurized Project 502505 Thefollowing day the flowwas increased to 24 ml/hour. Ten consecutive samples of 2 ml were taken. Theflowwas halved to 12 ml/hour and ten consecutive samples of 2 ml were taken. After sampling theflow of the column elution systemwas halved to 6ml/hour. Analysis was performed on subsamples of 1 .5 ml . The aqueous samples were extracted in a 5 :1 (v:v) ratiowith n-hexane. The shaking time was 30 seconds. The n-hexane layer wasanalysed. With analysis it was observed that differential results were obtained forthe water solubility at theflow rates of 12 and 24 ml/hour. Therefore, thetest at 24 ml/hour was repeated. 

### The pH was measured fromthe water fractions that were collected for the determination ofthe flow rates. The eluates were checked for the presence of undissolved particles using a turbidimeter. The experiment was also performed using a column filled with blank carrier material . The procedure was identical to the procedure used for the column loaded with test substance. At each flowrate, two consecutive samples were taken for analyses. 

### The column elution method was performed at 19.7°C t 0.3°C. 10.4 . Analytical method 10.4 .1 . Analytical conditions Quantitative analysis was performed according to the analytical method as validated in Chapter 7. Turbidity measurements: Instrument 2100 AN IS Laboratory Turbidimeter (Hach Company, Loveland, Colorado, USA) Unit NTU Calibration range < 0 .2 to 7500 NTU 10.4 .2. Preparation of the calibration solutions Stock solutions Stock solutions ofthe test substancewere prepared in n-hexane at concentrations of 1085 - 2110 mg/I . 

### Calibration solutions Calibration solutions in the concentration range of 0 .04 - 6mg/1 were prepared fromtwostock solutions. The end solution of the calibration solutions was n-hexane. 10.4 .3. Sample Injections Calibration solutions were injected in duplicate . Test samples were analysed by single injection. 10.4.4 . Calibration curves Calibration curves were constructed using at least five concentrations. For each concentration, two responses were used . Quadratic regression analysis was performed using the least squares method with a 1/concentration2 weighting factor. The coefficient of correlation (r) was > 0 .99 for each curve.



### Final report - Page 27 -1-Decene, sulfurized Project 502505 

### 10.5. Interpretation 10.5.1 . Specifications 

### The water solubility of a test substance is specified by the saturation mass concentration of the test substance in water at a given temperature and is expressed in g/I . 10.5.2 . Formulas Response (R) Peak area of the test substance [units] Maximum

difference highest value-lowest value x100% mean value where: 'mean value' is the mean ofthe highest and lowest value. 

### Calibration curve R=a CN + b CN + c where : a = quadratic regression factor [units x (I/mg)Z] b = linear regression factor [units x I/mg] 

### c = intercept [units] Analvsed concentration (Ce) C. - - b +Jb2 - 4a x (c - R) x d 2a where: d = dilution factor

Final report - Page 28 -1-Decene, sulfurized Project 502505 10 .6. Results 10 .6.1 . Preliminary test The content of test substance dissolved in thewater sample was 46.9 Ng/I . Note: The value obtained could be overestimated since the content of the centrifugation control sample was significantly lower (i .e. 25.3 pg/I). Further research to investigate the results was not performed since both values were significantly below 10 mg/I . According to this, the column elution method was selected for the main study. 10.8 .2. Main study The results for thewater samples of the column elution method are given in Table 7. With a flowrate of 24 ml/h a mean water solubility of 9.86 ug/I was obtained. Thecoefficient of variation (CV) was 5 30% . Asmall response of thetest substancewas observed in the chromatograms of the test samples obtained at the flowrate of 12 ml/h. The concentrations were below the nominal concentrationof the lowest calibration solution. Taking thesample extraction method into account it corresponds with a water solubility of < 8Ng/I . The test at 24 ml/h was repeated. With the new test, the sample concentrations were close to the noise level of the GC-MS instrument and therefore below the nominal concentration of the lowest calibration solution. Taking the sample extraction method into account it correspondswith a water solubility of < 8Ng/I . Based on the results obtained it was concluded that the water solubility of the test substanceis 510pg/I . Amore accurate value could not be given since the test concentrations were close to the detection limit of the GC-MS method. The analytical method with a 5:1 (v:v) extraction method and sample volumes of 1 .5 ml was considered to be optimal for the support of thecolumn elution method. No test substance was detected in the samples fromthe blank column. Theturbidity of the eluates was < 0 .5 NTU . It wasconsidered that the eluates had no undissolved test substance particles (i .e. the test substance was a liquid. Particles of thetest substance could not be present) . 

### Table 7 Main study-water solubility ofthe test substance Flowrate Sample Concentration ana l sed pH 

### no. Individual Mean CV Mean MD ml/h /I /I % /I % 24 1 10.7 9 .86 7.8 <10 n.a. 7.9 2 11 .0 3 9

.21 4 10.2 5 10.4 6 9

.64 

### 7 8.67 8 13.7 9 9 9

.47 

### 10 9.42

Final report - Page 29 -1-Decene, sulfurized Project 502505 Table 7 Continued Flowrate Sample Concentration ana l ed pH 

### no. Individual Mean Cv Mean MD ml/h /I /I % 12 1 < 8 < 8 n.a. 8 .0 

### 2 <8 3 <8 4 <8 5 <8 6 <8 7 <8 8 <8 9 <8 

### 10 <8 24 1 < 8 < 8 n.a. 6.6

2 <8 

### 3 <8 4 <8 5 <8 6 <8 7 <8 

### 8 <8 9 <8 10 <8 Mean of the concentrations obtained at one flowrate. Mean of the concentrations obtained at a flowrate of 12 ml/h and repeated 24 ml/h. Outlier according to the Dixon's 0-test at 95%confidence level . 10 .7. Conclusion Thecolumn elution method was applied for thedetermination of thewater solubility of 1-Decene, sulfurized . Thewater solubility of the test substance at 20°C was 510jig/I . The pH of the aqueous samples was 6 .6 - 8.0.

Final report - Page 30 -

### 1-Decene, sulfurized Project 502505 11 . PARTITION COEFFICIENT 11 .1 . Guidelines European Community (EC), EC no. 440/2008, Part A : Methods for the Determination of PhysicoChemical Properties, GuidelineA .8 : "Partition Coefficient", Official Journal of the European Union no . L142, May 31, 2008. Organization for Economic Co-operation and Development (OECD), OECD Guidelines for the Testing of Chemicals no. 107: "Partition Coefficient (n-octanol/water), Shake Flask Method", July 27, 1995. United States Environmental Protection Agency (EPA), Product Properties Test Guidelines no . OPPTS 830

.7550 : "Partition Coefficient (n-octanol/water), Shake Flask Method", August 1996. 11 .2 . Reagents n-Octanol Sigma-Aldrich, Steinheim, Germany 

### All reagents were of analytical grade, unless specified otherwise. 11 .3. Performance of thestudy Four methods are available for the determination of the partition coefficient (Po ,) of the test substance. The principle of each method is described below : 1 . Shake flask method Test substance is partitioned in a two-phase systemof n-octanol and water. After phase separation, the concentration of the test substance in both phases is determined by a suitable analytical method. The shake flask method can be used for test substance with a log P. value in the range of -2 to 4. 2 . HPLC method Asolution of the test substance is injected onto a reversed-phase HPLC column. The log Pmvalue is calculated fromthe retention time of thetest substance. The HPLC method covers log Po , values in the range of 0to 6

. 3 . Estimation method The solubility of the test substance in n-octanol and in water is determined. Thequotient of the noctanol solubility and thewater solubility is an estimation of the Po , . The estimation method can be applied if the shakeflask method and HPLC method are not applicable. 

### 4. Calculation method The calculation method is based on thetheoretical fragmentation of the molecule into suitable substructures for which reliable log Pa,. increments are known. The log Po, ., is obtained by summing the fragment values and the correction terms for intramolecular interactions. Lists of fragment constants and correction terms are available. The test substance is a mixture of multiple components with high log P"w values. The shake flask method was therefore not applicable for the test substance. The HPLC method with UV and refractive index (RI) detection was tested to determinethe log P of the test substance. However, it was found that the components of the test substance had no sufficient sensitivity for both UV and RI detection. According to this the log Po , of the test substance was determined by the estimation method. n-Octanol solubility Test substance was stirred with n-octanol at a 1 :1 (w/v) ratio (i .e. at a nominal concentration of 1 .01 x 103 g/I) at 19.8 t0 .2°C for approximately 2 .5 hours . After stirring, the test sample wasvisually interpreted. Final report - Page 31 -1-Decene, sulfurized Project 502505 

### Water solubility Information on the water solubility of thetest substance is given in Chapter 10. The water solubility was 510x 10's g/I . 11 .4 . Results After the stirring period, the n-octanol sample was clear and no undissolved test substancewas observed. Fromthis it was concluded that the n-octanol solubility of the test substance was > 1 x 103 g/I . The Po calculated as the quotient of the n-octanol and water solubility, is > 1 .0 x 108 . It corresponds with a log Pow

value of > 8.0. 11 .5. Conclusion 

### The estimation method was applied for the determination of the partition coefficient (P.) of 1-Decene, sulfurized. The PoV, value of the test substance at 20°C was > 1 .0 x 108. It corresponds with a log P value of > 8.0.



### Final report - Page 32 -

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