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Number Associated # Attachment Name Attachment Filename of Pages Section CBI Number 001 EPA Letter (P-12-0425) (Final Report - Kow) (5- EPA Letter (P-12-0425) (Final 1 28-2013) (public) Report- Kow) (5-28-2013) 002 Report-18157-386- translatio n_p ublic Report-18157-386 - 27 translation
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### Associated PMN Section Number N/A Does not contain CBI



### Report Number EPAX130528304219814 SANITIZED SUBMISSIONMay 28,2013 U.S. Environmental Protection Agency Office of Pollution Prevention and Toxics Confidential Business Information Center (CBIC)- TS7407M Attention: Audrey Binder EPA East Building, Room 6428 1201 Constitution Avenue, NW Washington, DC 20004-3302 Dear Ms. Binder: Reference: PMN P-12-0425 Submission Report NumberPlease find attached the following final report on the PMN substance: Determination of Partition Coefficient (n-octanolfwater) of Liquid Chromatography (HPLC) Method OECD Guidelines for the Testing of Chemicals 117 (2004) One confidential copy and one public copy are attached.

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### Report Number EPAX1305283042 19814 SANITIZED SUBMISSION

### FINAL REPORT Detennination ofPartition Coefficient (n-octanoVwater) of High Performance Liquid Chromatography (HPLC) Method OECD Guidelines for the Testing ofChemicals 117 (2004)

Submitted to:

Prepared by:

May 10, 2013



### 1 , . 

### . ·.·· · . . 

### :

· 

## COMPLIANCE WITH THE GLP STANDARDS

Sponsor Study Title Determination of Partition Coefficient (n-octanol/water) of High Performance Liquid Chromatography (HPLC) Method OECD Guidelines for the Testing of Chemicals 117 (2004) Study 

### No. 

## i' hereby certify that this study was carried out in accordance with the protocol and with our standard operating procedures, and that the report accurately describes the fest results . The study described 

### in this report was conducted 

### in compliance with the following Good Laboratory Practice (GLP) standards:
OECD Principles of Good Laboratory Practice (1997)
Study Director Sealed date: May 10, 2013

2

## QUALITY ASSURANCE STATEMENT

Sponsor Study Title Detenninat . ion of Partition Coefficient (n-octanol/water) of High 

### Performance Liquid Chromatography (HPLC) Method OECD Guidelines for the Testing of Chemicals 117 (2004) 

### Study No.
I 

### verify that this study was carried out in accordance with the following Good Laboratory Practice(GLP) and the reported results reflect the raw data of the study: OECD Principles of Good Laboratory Practice (1997) The types of inspections and their dates, and the dates the results were reported to the test facility management and the study director are listed below:

Protocol: Phase of Study Inspected
Draft protocol Protocol Amendment 01 Amendment 02 Amendment 03 Amendment 

### 04 In-progress study: Date of Inspections August 7, 2012 October 16, 2012 October 29, 2012 November 26, 2012 April 10, 2013 April 12, 2013 Dates of Reporting to Test Facility Management and Study Director August 9, 2012 October 16, 2012 October 30, 2012 November 26, 2012 April 10, 2013 April 15, 2013 Preparation of test substance solutions October 19, 2012 October 19, 

### 2012 Measurement of retention time of test substance Final report:

Draft report Final report 

### Quality Assurance Personnel October 19, 2012 November 1, 2012 May 10, 2013 October 19, 

### 2012 November 1, 2012 May 10, 2013



### Sealed date: May 10, 2013
3{ \::
. 

### :: 

## INTRODUCTION 1 STUDY 

### TITLE Determination of Partition Coefficient (n-octanoVwater) of High Performance Liquid Chromatography (HPLC) Method, OECD Guidelines for the Testing of Chemicals 117 (2004)


### 2 PURPOSE This study was conducted to determine the partition coefficient (n-octanoVwater) of the test substance. 

## 3 TEST GUIDELINE OECD Guidelines for the Testing of Chemicals 117 (2004) "Partition Coefficient Znoctanol/water), High Performance Liquid Chromatography (HPLC) Method" 

### 4 GLP COMPLIANCE OECD Principles ofGood Laboratory Practice (1997) 

### 5 SPONSOR

6 

### TESTING 

### FACILITY (Head Office)

7 

### TESTING 

### FACILITY (Laboratory)

8 STUDY 

### DIRECTOR

4( 

### 9 EXPERIMENTAL SCIENTIST 

### (Experimental work) 10 STUDY PERIOD Study 

### initiation: Experiment: Study 

### completion: October 15, 2012 October 19, 20 12 May 10, 20 13 11 STORAGE AND RETENTION OF THE TEST SUBSTANCE AND RECORDS 

### The followings 

### will be stored in the 

### archives ofthe testing laboratory. 1) 

### Protocol 2) Final report 3) 

### Raw data 4) Test substance 5) Reference substance 6) Other requirements



### 5( 

## CONTENTS Page SUMMARY···· ················ ·· · ··················································· · ··7 TEST SUBSTANCES· · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 9

1.1 Name, structural formula and physico-chemical properties· · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 9 1.2 Source········································· ·· ·· · ··························· 10 1.3 Stability under the storage conditions·· · · · · · · · · · · · · · · · · · · : · · · · · · · · · · · · · · · · · · · · · · · · · · 10 2 TEST METHOD · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 11 2.1 2.2 2.3 2.4 2.5 2.6 2.7 2.8 Reference substances · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 11 Reagents · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 12 Apparatus··········· · ··· · ·· · ······· · · · ····· ·· ····· ··········· · · ······ · ······· · · 12 Analytical method · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 12 Preliminary estimate of the partition coefficient · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 12 Preparation of reference substance solutions · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 13 Preparation of test substance solutions · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · }).3 Verification of correlation between partition coefficient and retention time · · · · · · · · · · · · · · · 14 2.9 Measurement of retention time and calculation of partition coefficient · · · · · · · · · · · · · · · · · · · 14 2. 10 Validity of the test·· · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 15 3 MEASUREMENT of pH of The WATER EXTRACT of The TEST SUBSTANCE -1 · · · · · · 15 3.1 Measurement of pH · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 15 3.2 Apparatus · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 15 4 MEASUREMENT of pH of The WATER EXTRACT of The TEST SUBSTANCE -2 · · · · · · 15 4.1 Guideline · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 15 4.2 Measurement· · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 16 4.3 Apparatus and reagent · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 16 5 RESULTS AND DISCUSSION··· · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 16 5.1 Deviation and circumstance that might have affected the reliability of the test result · · · · · · 16 5.2 Results of the measurement of the Jog Pow · · · · · · · ······ ····· ················· · · · · · · 16 5.3 Results of the measurement of the pH · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 17 Table 1 Results of determination · · · · · · · · · · · · · · · · · · · · · · ·: · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 18 Figure l Correlation diagram between log Pow and log k · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 19 Figure 2**~omatograms** · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · : · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · 20 Appendix 1 Infrared absorption spectra. ............................................................................................. .. .. ..**22~23** Appendix 2 High performance liquid chromatograph (HPLC) analytical conditions ................................**24~25**

6

## SUMMARY Sponsor:
Study title:

Determination ofPartition Coefficient (n-octanol/water) of High Performance Liquid Chromatography (HPLC) Method OECD Guidelines for the Testing ofChemicals 117 (2004) Study number:

Test method: OECD Guidelines for the Testing ofChemicals 117 (2004) ''Partition Coefficient (n-octanol/water), High Performance Liquid Chromatography (HPLC) Method" 1) Reference substances : Methyl Benzoate Ethyl Benzoate 1,4-Dichlorobenzene Cumene (lsopropylben7...ene) 1,2,4-Trichlorobenzene Triphenylamine 2) Analytical method: High Performance Liquid Chromatograph (HPLC)



### 7( 

### Results : The peaks ofthe test substance were detected on the chromatograms, Based on order ofthe retention time, component A

-F were defined. The partition coefficient (log Pow) value of each component ofthe test substance was calculated and was shown below. Component A was presumed to be one ofthe impurities 

### in the test substance. Because the retention time of Component A was very different from the reten tion time of the major components 

### in the · test substance, the structures ofthe major active ingredients 

### in the test substance are very similar and suggests that log Pow for these components should be similar, the log Pow for components was very different from the log Pow for the major components in the test sub

stance and also very different from the predicted log Pow( 4.87) . Component log Pow A 

### 2.8 B 4.5 

## c 4 .6 D 4.6 E 4 .8 F 4 .9



### 8 

## I I

## 1 TESTSUBSTANCES 1.1 Name, structural formula and physico-chemical properties Nameofthe 

# I chemical substance I

Alternate name 

# i CASRN I

# I l

Structural formula or 

# I

rational formula 

### I (ifboth ofthem are 

## ! unknown, outline of i**~** preparation or ! manufacturing) 

### I Molecular weight 362. 11 Purity{%) ofthe chemical substance 99.47 subjected to the study

Lot number ofthe chemical substance subjected to the study Name and content of impurities Vapor pressure 2.9kPa (25CC) Solubility in water**~1001** mg/L 1-octanol/waterpartition coefficient 

## - Melting point 

## - Boiling point llOCC(Representative value) Appearance Liquid at room temperature Stability Stable

9

# (
. Solubility in Solvent Solubility Stability 

### in solvent solvents and the like A cetone ;;;; 87889 mg/L 

## - Above mformatlon IS 

### provtded by the sponsor. 1.2 Source Supplier: 1 .3 Stability under the storage conditions During the study, the test substance was stored in a desiccator in the testing laboratory (storage condition: room temperature, dark, air

-tight).

· After the completion of the experiment, the infrared absorption spectrum of the test substance was measured. Stability of the test substance was confirmed by comparing the spectrum with that measured before the start ofthe experiment. [Appendix 1] Apparatus: Infrared spectrophotometer Nicolet iS 10, Thermo Fisher Scientific Inc.

10(**~.** 

## 2 TEST METHOD The study was conducted in accordance with the OECD Guidelines for the Testing of Chem icals 11 7 (2004) "Partitio n Coefficient (n

-octanol/water), High Perf ormance Liquid Chromatography (HPLC) Method' '. Six substances with kn own partition coefficients (see 2.1) were selected as referen ce substances by preliminary examination carried out before the study initiatio n . Thiourea (see 2.2) was selected as a non-retainable substance, for determination ofthe dead time 

### (fc). 2.1 Reference substances

No . Name CASRN Structura l formula Supplier 

# J Reagent Grade Lot No. Purity 1 Methyl benzoate 93-58-3 Hl\ 

# o-<**~** Wako Pure Chemical 

## ! Industries, l.td., [ Wako guaranteed grade KWH4529 99 .9% 

# I

2 Ethyl benzoate 93-89-0 

# / H 3 

# o-<-CR, Wako Pure Chemical 

### ! Industries, Ltd., !Wako guaranteed grade KWP4133 99 .9%
3 I,4

-DicWorobenzene 106-46

-7 

# C l --o--CI Tokyo Chemical

### Tokyo Chemical ICBHIB 99 .9% Industry Co., Ltd. g uaranteed grade 4 Cumene (Isopropylbenzene) 98

-82

-8 

# o-r· Tokyo Chemical 

## I Tokyo Chemical 

# c\
J 6YAKC 99.9% CH1 Industry Co. , Ltd. !guaranteed grade I I C l I 5 I,2,4- Tricl\lorobenzene 1120-82

- 1

# ~ I Tokyo Chemical 

## I Tokyo Chemical ftrst 3LYYC 99.6% # a [ndustry Co., Ltd. grade Cl I 6 Triphenylamine 

# I 

# 9 603

-34

-9
Kanto Chemical Co., 

# I 004W2038 100.0% 

# UND Inc.**guaranteed** grade



### 11

## L 2.2 Reagents

2.3

2.4 Thiourea: Guaranteed grade, Kanto Chemical Co., Inc . Purity 98.9% , Lot No. 107N2156 Methanol: HPLC grade, Wa.ko Pure Chemical Industries, Ltd. Sodium Dihydrogenphosphate Dihydrate: Guaranteed grade, Wa.ko Pure Chemical Industries, Ltd., Disodium Hydrogenphosphate 12-Water: Guaranteed grade, Wa.ko Pure Chemical Industries, Ltd., Ultra pure water: Grade A4 in Japanese Industrial Standards (JIS) K0557 Apparatus Electro balance: AG204, Mettler 

### K.K. PB3002, Mettler K.K. pH meter: 

### Twin pH B-212, Horiba , Ltd. Analytical method .::



### The retention times ofthe test substance and reference substances were measured with high performance liquid chromatograph (HPLC). Analytical conditions are 

### shown 

### in Appendix 2. The pH ofthe HPLC eluent (10mM sodium phosphate buffer' :methanol= 25 : 75 ) was 7.9. *Prepara tion of 1 OmM 

### sodium phosphate buffer : 0.78 g of sodium dihydrogenphosphate and 1.79 g ofdihydrate disodium hydrogenphosphate 12-Waterwere dissolved to 

### 1 L with ultra pure water. 2.5 Preliminary estimate ofthe partition coefficient The value ofthe partition coefficient (log Pow) ofthe test substance was estimated to be 4 .87, by the testing laboratory using the EPI (Estimation Programs Interface) Suite ver. 4.10. KowWin ver. 1.68 (U.S.EPA, 2011).

12·: 

### .. ·. l '
. \. 

### 2.6 Preparation ofreference substance solutions Following the table below, duplicate solutions ofthe reference substances were prepared by mixing appropriate volumes of 1

### OmM sodium phosphate buffer, the stock solution ofthiourea (dissolved in methanol) and the stock solutions of each reference substance (dissolved in methanol). The relative proportion of the solvents in the mixed solution was equal to the eluent ofthe HPLC. Partition Concentration Volume Concentration in Coefficient

# . ofthe stock collected the final solution Name solution (log Pow) (mg!L) (f.lL) (mg/L) 10 mM Sodium phosphate buffer 

## - 375 

## - Methanol 

# - - 855 

## - Thiourea 

## - 500 30 10

_ , 

### . , Methyl benzoate 2.1 1000 40 27 Ethyl benzoate 2.6 1000 40 27 1,4-Dichlorobenzene 3.4 1000 50 33 Cumene (Isopropylbenzene) 3.7 1000 50 33 1,2,4- Trichlorobenzene 4.2 2000 20 27 Triphenylamine 5 .7 1000 40 27 Total volume of Methanol 1125 (J.L Total volume of the final solution 1500 

### f.1L Concentration of Methanol 75% 

## * : OECD Guidelines for the Testing of Chemicals 117 (2004)
2.7 Preparation oftest substance solutions The 125 .8 J.LL (specific gravity : 1.59•) portion ofthe test substance was dissolved to 20 mL with methanol as stock solution. Following the table below, duplicate mixed solutions of the test substance were prepared by mixing 

### lOmM sodium phosphate buffer, the stock solution of thiourea (dissolved in methanol ) and the stock solution of the test substance (dissolved in methanol). The relative proportion ofthe solvents in the mL'(ed solution was equal to the eluent ofthe HPLC. 

## * : measured value obtained by our testing facility

13\ 

### ( Concentration Volume Concentration in ofthe stock Name collec ted the final solution solution (mg/L)**(~)** (mg/L)
1 OmM Sodium phosphate buffer 

## - 375 

## - Methanol 

## - 845 

## - Thiourea 

### 500 30 10 Test substance 

### 10000 250 1670 Total volume of Methanol 1125**~** Total volume of the final solution 1500**~** Concentration of Methanol 

### 75%**~** 

### 2.8 Verification ofcorrelation between partition coefficient and retention time The duplicate reference substance solutions were analyzed with HPLC. The retention times (min.) 

### of the reference substances and thiourea were determined from the chromatograms. The retention time of the reference substances (tR) was corrected by subtracting the retention time of thiourea 

### (to), i.e. tR- 

## to. The capacity factor (k) 

### was calculated according to the followi ng equation. 

### k

## = (tR- 

### to) I to The log Pow for each reference substance was plotted against its logarithmic value of capacity factor (log k), 

### and the regression line was drawn by the least squares method. log Pow 

## =a 

### + b log k 

### where a: y-intercept ofregression line b: slope ofregression line A correlation coefficient (r) between log 

### k and log Pow was determined to verify the linearity. Criteria for linearity is that r value is greater than or equal to 0.98. 2.9 Measurement ofretention time and calculation ofpartition coefficient The duplicate test solutions of the test substance were analyzed with HPLC. The retention times (min.) of the test substance and thiourea were determined from the chromatograms. The logarithmic value ofthe capacity factor (log k) 

### ofthe test substance was calculated from the retention time of the test substance (tR) and that of thiourea (to). The Partition coefficient (log Pow) of the test substance was calculated using the linear regression formula derived in Section 2.8.


### 14

### 2.10 Validity ofthe test • The value oflog Pow determined from duplicate measurements should fall within a range 

### of±0.11ogunits. • The temperature during the measurement should not vary by more than 

### ±1 °C. 

### 3 

## MEASUREMENT of pH of The WATER EXTRACT of The TEST SUBSTANCE -1 The pH ofthe water extract ofthe test substance was measured. ( 3 .1 Measurement ofpH The 

### 10.0 g

### 6289~**)** portion of the test substance and the 

### 10.0 g of ultra pure watJr* were entered in the 30 mL-separating funnel, mixed with shaking apparatus for 5 min. and leaved to separate to two layers completely. Upper water layer was sampled and the pH was measured.

*Ultrapure water: Grade A4 in Japanese Industrial Standards (JIS) K0557 pH5 .3 (measured value)
3.2 Apparatus pH/D.O. meter : 

### MM-60R, OKK-TOA Corporation Shaking apparatus : SA-31 Yamato Scientific Co.,Ltd.


### 4 

## MEASUREMENT of pH of The WATER EXTRACT of The TEST SUBSTANCE -2 The pH of the water extract of the test substance was measured in accordance with the Guideline "ASlM standard 

### 02110-00 (Reapproved 

### 2012)" to obtaine the pH-value correctly. 4.1 Guideline ASTM standard 

### 02110-00 (Reapproved 

### 201 2)



### 15

### 4.2 Measurement 

### 1 Preparation ofthe water Approximately 1000 mL of the 

### ultra pure water was sampled in the 

### 1 000-mL Pyrex beaker , boiled for 5min with electric hot plate, then covered and cooled to room temperature. A 250 

### mL aliquot ofthe water (pH 5.8) was to pH 7.3 with the titration of0.23 

### mL of 0 .01 N NaOH. The amount of0.46 

### mL was added to 500 

### mL water and confirmed pH of 7.1. 2 Pretreatment Aliquot of 50 mL ofthe test substance was transferd to a 200-mL separatory funnel containing 

### 50 

### mL of Ultra pure water (pH 7.1) prepared by the above procedure, shaken the mixture for 30 min, then let stand for 30 

### min. The water extract 

### was collected and the pH 

### was determined with pH meter(n=S). 4 .3 Apparatus and reagent pH/D.O . meter : MM
-60R, DKK-TOA Corporation Shaking apparatus : SA-31 Yamato Scientific Co.,Ltd.
0.01 moVl Sodium Hydroxide Solution (N/ 100) : Kanto Chemical Co ., Inc. 

## 5 RESULTS AND DISCUSSION 5.1 Deviation and circumstance that might have affected the reliability ofthe test result There was no deviation or specific factor that might have affected the reliability ofthe test results. 5.2 Results ofthe measurement ofthe log Pow The measurement results are shown in Table 1, correlation diagram between log Pow and log k 

### is shown 

### in Figure 1, and HPLC chromatograms are shown 

### in Figure 2. The regression line formula is shown below. The correlation coefficient r 

### was fulfilled the criteria, r**0.98.** 

### log Pow = 

### 1 .704 

## + 2.867 x 

### log k 

### r = 0 .9968 The peaks ofthe test substance were detected on the chromatograms, Based on order of the retention time, component 

### A-F were defmed. The partition 

### coefficient (log Pow ) value
16

# t... .. of each component ofthe test substance was calculated and was shown below. This study was judged valid since the value of log Pow derived from repeated measurements f ell within a range of± 0.1 log units, and the temperature during the measurement was within a range of± 1°C. Average values shown below are judged to be log Pow of the test substance. Component A was 

### presumed to be one of the impurities in the test substance:**~ecause** 

### the retention time of Component A was very different from the retention time of the major components in the test substance, the structures ofthe major active ingredients in the test substance are very similar and suggests that log Pow for these components should be similar, the log Pow for component A was very different from the log Pow for the major components in the test substance and also very different from the predicted log Pow(4 .87). comPOnent Actual measurement Average A 2.85 2.8 2 .84 B 4.49 4 .5 4.49 

## c 4.55 4 .6 4.55 D 4.65 4.6 4 .64 E 4.79 4.8 4.79 F 4.85 4.9 4 . 85 

### 5.3 Results ofthe measurement ofthe pH The pH ofthe water extract prepared according to the procedure described in Section 4.2 was measured to be 4.7 . The measured values were 4 .7, 4.5, 4.7, 4.8 and 4.6(n=5).

Methoxytridecafluoroheptene which is the main component ofthe test substance is nondissociative and hardly

-soluble in water. Thus, the main component in water extract is thought to be very few. So, it was considered that the obtained pH value did not represent the property ofmain component.

The pH of the water extract prepared according to the procedure described in Section 3.1 was measured to be 4 .5



### 17Table 1 Results ofmeasurement 

## I Peak jchromato1 

## to or tR 

## I k 

# l logk log Pow Name 

### ! gram 

# I I 

### i N o. No. 1 (min) 

# I i Thiourea 

# I 1 I 

### ! 1 .440 

## I 

## - I 

# - - I (Dead time measurement to) 2 1.441 

## - - Methyl benzoate 

## I 2 

### 1 

# I 3.313 

## I 1.301 

# I O.li4 2.1 

## I 2 ; 3.3 12 

### j 1.298 0.113 I Q) Ethyl benzoate I 3 

### 1 . 4287 1.977 I 0.296 2.6 () I

### ~ 

# l I 2 I 4.286 1.974 

# l 0.295 {I) I .0 ::: 1 ,4-Dichlorobenzene 

# I 4 1 

## i 7.278 4.054 1 o.6o8 3.4 {I) Q) 2 

## I 7.274 

# I 4.048 1 o.6o7 () 

## I 

# = Q)

.Cumene (lsopropylbenzene)l 5 1 9.711 5.744 0.759 3.7 t.J 

## .a OJ'. 2 1 9.7o5 

## I 5.735 

# I 0 .759**:** I I ,2,4- Trichlorobenzene 

# l 6 I 1 12.109 . 7.409 0.870 4 .2 " 2 12.100 

# l 7.397 0.869 I Triphenylamine 1 7 1 34.335 j 22.844 

# I 1.359 5.7 

### I 2 1 34.306 

## I 22.807 1358 Thiourea 

# I 1 1 1.4 41 

### I 

## - I 

## - - ! (Dead time measurement: to) 2 

## i 1.440 

## - - ) ' 

# l 2 I I 5.043 2.500 

# l 0.398 2.85 !Average Component A 

### l 2 ! 5 .035 2.497 1 o.397 2.84 2.8 

## I 3 1 

## l 14.983 

## I 9.398 I 0.973 4.49 !Average Component B 

### I 2 11 4 .943 9 .377 I 0.972 4.49 

### 1 4.5**~** I

... c 

# I 4 1 1 15 .643 9.856 

# ! 0.994 4.55 tAverage II) tQ Component C Q) - 115.653 

# I 4.55 

# ! 4.6**E-<~** i 2 9.870 

## i 0.994 ;:I ! II) 

## I 5 1 16.743 10.619 

# I 1 .026 4.65 iAverage ComponentD 2 16.699 10.597 

### I 1.025 4.64 4 .6 ! I 6 1 118.665 1 11 .953 

### I 1.077 4.79 Average i Component E 

# i I 2 1 18.616 1 11.928 1.077 4.79 4.8 I 7 

### 1 19.484 1 12.521 I 1.098 4.85 Average ComponentF 

### I ! 

## ! 2 I9.432 12.494 1.097 4.85 4 . 9 

## to: Dead ttme tR: Retention time ofreference substance or test substance k: Capacity factor Equat ions: k 

## =(tR-to) I 

## to Log Pow of the test substance is calculated using the following regression formula 

### Regression formula calculated from the reference substances data log Pow= 1.704 

### + 2.867 x log k 

### r= 0.9968



### 18

### Figure 1 Correlation diagram between log Pow and log k



### 6.0 5.0 

### 4.0**~** 0 Q.. 

### 3.0 bO 0 

# - 2.0 1.0 0.0 0.0 y= 1.704 

### + 2.867 X r= 

### 0.9968 

### 0.5 log k



### 19 

# I !

..-- - -,1 

# I • Reference substance OComponent A 

### 0 Component 

### B !:!:. 

### Component C 

### I0 Component D 

### X Component 

### E +Component 

### F 1. 0 

### 1.5

### Figure 2 Chromatograms Reference substances, 

### No. 1



## · ·- 100 

## !**~** :; 

# ; ;;

### ~ .: :;; eo


## ..,
to 0 ,;, 

## ... 

# t\

,;,**·-- -----..~~···**  

# -·--·---·-·--· -··-----·-· t" · t lT tff •

I fah) (ala)**1.~0** 

# .. 0. 011 uu !t.S U U ll 

# .. o.m 650. 4 UIT 

# .. o.m 'tS. I f.%11 

# .. O.Zll llU S . fll 

# • o.w**l~f 4**  11 .1**·-~** 53. f T .O 0.4 11.0 fl.l IS.t l Liot 

# • o .m 1444.5 S4.SJI 

# • o .n1 10tf.4 B
. t au 3U 2.9.0**:** UILJ**---.----- ~** **------~--------------­** •u IDd or IQort ... 

### Reference substances, 

### No.2

""'-V i 100**~** ! eo 

# .. :!**~** I! .: 

### "' eo 

# I i 

## .., 

# A Jt 0



## ... 

# ..**.~ -~** **----· --** **----------------** illlll"·t>ll«'·l

1. 441 

# • O . OM sou t7.0 ? . 1 1.1 11 Fl o . m 591.7 14.1 '-4 UN 1111 0.1 51 191.! su f.l t.m Ill o. n1 lit.I IL l 11.1 t. TOI 1111 o. w 101U fU IS. I U .IOO 1111 0.341 1515. I lS.S 11. s U.JOI Ill 0.971 Ull.S n.1 11.0 ) · 1•: 1051.1 4tl . l

._...,.._••..-- •• ..

•-•-wmu ...

# ___

tu hd of lt»rt 

### '*'*
20( "\ ,, 

### Figure 2 Chromatograms (continued) Test substance, No.1

J •.AU i 140 

### "
to
10 <10 20 

# b Q**=~** 0 :l:!. fi.

..... 

## ••
t'-t It J!t II

• (lila) (liJaJ 1.441 • s.ou •**1~1*1** • 1$.14) • lf

. 7U • lUIS • lt

. IM Ill Hl: O.OM o. uo o.no o.m 0.$11 o.m 0.411 i :!

## h



## ...**~"'** 

## "' 3.0 1. 4 m. s IIIII.S lOQ.G l7U.t
U t. W ofltocrt t .U 

### Test substance, No .2**·~· j~** 

100 10 10 

# ..

9T. I 0.5 0. 1 0.1 1.1 45.1 10

. 5 15l.4**·---~ ------** **------·--~~~---------­** --- ·--.;.. ·**,;;llliii';.;;.;'_·~;,.IW;.;;..·;. ~---~=**  t'·t



### ' l410 1'1 S.OlS l1 11.111 l1 IU$1 l1 lUll l1 lUll llr lt. 4ll I'll Hrr:**(o~** 0.011 0.150 O.IU o.m 0.531 0.120 o. c

n ! U.t u l.O I. I m. a IT!6.1 IIU mu 110. 4 0.1 0.1 0.1 7.4 "·I I f. I 115

. 1 11.) 1. 2 0.1 G. I 1.1 ll. t 10.1

II. I O.l 0.1 o.o 1.5 11.1 10.1



# ...._ __**""-·--- --~,....~-~**  U t bd of te.orl Ut 

### 21

# Appendix 1
Infrared absorption spectra



### 22

### Figure A-1-1 Infrared absorption spectrum ofthe test substance before the measurement



### • 0 i 

### ,i 

# II 100 90 90 70 liO 50 40 30 20 10 4000 8#: 

# * Jun 29 13:19:40 2012 (GMT009:00} 

### ***A~:.-:32**

### ~-- •tOOO 

# I

# ~~**I**

... ;;:;

2500 2000 1SOO**Wwe~** cm-1



### Figure A-1-2 Infrared absorption spectrum ofthe 

### test substance after the measurement 100**~** y T

# ~

# '~ 90

# w~**.** I 80 

# I I 10 60

## ~**~** 8 

### , ,.,. 

# ... c; !! <0 

### " so 

## ... 

# .. 

# "" "' 

# .. ...**~** ..... 40 

## I 

# - 30 !::: 

## ... 

## ...**~** 20 

# }e 10 I 0 ::! - 

# I 4000 3500 3000 2500 2000 1500 1000 w.v......,.,.,.Ccm-1) 8#: 

# * Apo-1213:08:07**2013(GMT-+0~)** • *Apr 12 13.1l8:07 2013 (GMT-+09!10) Ap!W'&tu.S: Nleolet 1510 ;tud• NumMr! 

# -**A~'\<z32** "est**ubttan~** 

# - l.otN**~~~J~:~~:** · A.-.( IJI"(f>'£--;;;:;-**~-C:** 4.000 m " L "1.



### 23High Performance Liquid Chromatograph (HPLC) Analytical Conditions System High performance liquid chromatograph Agilent 110.0 (No.6), Agile nt Technologies Work station: Degasser: Pump: Auto sampler: Column oven: Photodiode array detector (DAD):
Conditions Chemstation Gl379A G1311A (Quaternary pump) Gl313A G1316A Gl3 15B

Column: lnertsil ODS-3, 5 JliD, 3.0 

### m.m i.d. x 150 

### mm, GL Sciences 

### Inc. Column oven temperature: 40°C Eluent: lOmM sodium phosphate buffer : methanol= 25: 75 (pH 7.9) Flow rate: Wavelength: Injection volume: 0.5 rnUmin 210nm

25