4480 LAKE FOREST DRIVE 

SUITE 312 

RLUE ASH, OHIO 45242 

in 

E 

PERFORMANCE 

CHEMICALS 

P. 

3 Ll 'P C2,0 

2012 FE-11 29 AN 6- 00 

February, 22, 2012 

Document Control Office (7407 M) 

Office of Pollution Prevention and Toxics (OPPT) 

Environmental Protection Agency 

1200 Pennsylvania Ave, NW. 

Washington, DC 20460-0001 

Attention: 40 CFR 799.5089 

Docket ID Number EPA-HQ-OPPT-2009-0112 

To Whom It May Concern: 

uuup~ipniuiiiquupugu0 ur5 iuiunu 

RE : Testing of Certain High Production Volume Chemicals; Third Group of Chemicals. 

Federal Register 76 (204), 65385-65410, October 21, 2011 . 

Benzenesulfonic acid, dimethvl (CASRN No. 25321-41-9) 

Nease Corporation previously submitted letter of intent (December 1, 2011) to comply with the 

subject test rule for Benzenesulfonic acid, dimethyl (CASRN No. 25321-41-9). 

Nease Corporation has conducted the following studies in compliance with the test rule and 

according to current OPPTS Harmonized Guidelines except Vapor Pressure which was tested 

using ASTM D 2879-10. The method for vapor pressure listed in the OPPTS Harmonized 

Guidelines (ASTM E 1782-08 thermal analysis) uses equipment that is obsolete as determined 

by the outside laboratory (Impact Analytical, Midland, Michigan 48640, PH:989-832-5555) 

contracted for the testing. The outside laboratory used of ASTM D 2879-10 (Standard Test 

Method for Vapor Pressure-Temperature Relationship and Initial Decomposition Temperature of 

Liquids by Isoteniscope) as a suitable replacement. 

1 . Boiling point: ASTM E 1719-05 

2. Vapor Pressure: ASTM D 2879-10 

3. N-Octanol/water partition coefficient (log 10 basis) or log KoW by Method B, ASTM E 

1147-92 (reapproved 2005) (liquid chromatography). 

CONTAINS NO CBI 
p. 2 

4480 LAKE FOREST DRIVE 

SUITE 312 

BLUE ASH, OHIO 45242 

N GhSE CHEMICA 

SNCE 

Attached please find a robust summary of those test results as reported by Impact Analytical, 

Midland, MI . 

Please feel free to contact me at 513-587-2804 or Phil . benesCaD-neasecorp .com if you have any 

further questions. 

Sincerely, 

Philip Benes 

Director of Technology & Product Development 
~y 1 M PACT 

ANALYTICAL 

1910 W. Saint Andrews Road - Midland, MI 48640 - USA 

Phone : (989) 832-5555 - Fax: (989) 832-5636 " www.impactanalytical .com 

A Michigan Molecular Institute Center of Excellence 

Customer: William Hehemann Report Number*: R11-0778 

Company: Nease Corporation Date Submitted: " 12/9/2011 

Address : 4480 Lake Forest Drive Report Date: 2/20/2012 

Suite 312 

Cincinnati, OH 45242 

Databook #: 580 (MTH), 574 (JMC), Analyst(s): J . Chatterton, M. Hall, 

436 (MFR) J . Roy, M. Rozniak 

Samples: S11-2023 QC: (Initial/Date) KAR 2/20/2012 

Determination of Octanol-Water Coefficient and Other Physical Properties of 

Xylene Sulfonic Acid 

Summary 

William Hehemann of Nease Corporation submitted a xylene sulfonic acid sample for the 

determination of octanol-water partition coefficient (KoW), boiling point, and vapor pressure. The 

determination of KoW was conducted using high-performance liquid chromatography with 

ultraviolet detection (HPLC-UV) . 

The determination of KoW for xylene sulfonic acid was conducted following ASTM method E 

1147-92 (Reference 1) . Reference materials with known KoW values were analyzed by HPLCUV and were used to bracket the retention time that was observed for the xylene sulfonic acid 

sample. A standard curve was used to generate the estimated log Ko , . The estimated log KoW for 

the xylene sulfonic acid sample was determined to be 1 .37. A summary of results that were 

obtained for the KoW determination are provided in Table 1. 

The boiling point determination followed ASTM method E1719-05 (Reference 2). A stirred 

flask ebulliometer was used, and the sample decomposed below the boiling point, so a boiling 

point could not be reported. 

The vapor pressure measurement was outsourced to an Impact Analytical approved laboratory. 

The analysis followed ASTM D2879-10 (Reference 3). The results from the analysis are 

provided in Table II. 

Experimental 

Sample Identification 

Impact Analytical ID Customer ID 

Sl 1-2023 Xylene Sulfonic Acid; Lot# N35P79 

HPLC-UV for KoW Determination 

The HPLC-UV analysis was performed using Impact Analytical standard operating procedure 

SOP-SEP-003 as a guideline for instrument operation . The determination of KoW for xylene 

1 of 10 pages 
sulfonic acid was conducted following ASTM method E 1147-92 (Reference 1). Solutions of the 

sample and reference materials were injected into an Agilent 1100 Series high-performance 

liquid chromatographic (HPLC) system that was equipped with a multiple wavelength detector 

(MWD). The MWD monitored a wavelength of 210 nn. Separations were achieved using a 150 

x 4 .6 mm Unison UK-C 18 column with 3 pm particles . Eluents of water with 0.1 % formic acid 

(Eluent A) and acetonitrile (Eluent B) were used for the isocratic method. A 10 gL injection was 

used for this analysis. Formic acid was used in Eluent A to obtained good peak shapes for the 

sample and for the reference materials. The pH of Eluent A containing water with 0.1 % formic 

acid was 2.52 for the analysis . The pH of the eluent is reported per requirement of ASTM 

method E 1147-92 (Reference 1). 

HPLC-UV Sample Preparation 

Approximately 0.01 gram of six reference standards (all reference compounds except 2,6-

difluorobenzoic acid and 2-fluorobenzoic acid ; see Table I) and the xylene sulfonic acid sample 

were individually weighed into a weighing boat and transferred to a single 50 mL volumetric 

flask. The contents of the flask were diluted with 20 mL of internal standard solution (0 .1 g 

internal standard in 200 mL of 50:50 water/methanol) and filled to volume with a 50 :50 

water/methanol mixture. The internal standard used for the analysis was 2,5-dihydroxy-pbenzene disulfonic acid, dipostassium salt . 

Approximate retention times for the six reference standards and the sample solution were 

determined via injections of single analyte solutions prior to the actual analysis that was used for 

the KoW determination. These preliminary analyses were conducted to correlate the retention 

times to the various reference materials and to find compounds that had retention times similar to 

xylene sulfonic acid. 

Solutions of two additional reference compounds (2,6-difluorobenzoic acid and 2-fluorobenzoic 

acid) were also prepared by weighing 0.01 gram of compound into separate weighing boats and 

by transferring to separate 25 mL volumetric flasks. Ten milliliters of internal standard were 

added to each flask, and the contents of each flask were diluted to volume with a 50:50 mixture 

of water/methanol . The two additional reference compounds were obtained and analyzed to 

obtain additional data points for the standard plot. 

Boiling Point Determination 

The ASTM method E1719-05 (Reference 2) was followed for this determination. A stirred flask 

ebulliometer was assembled, and the measurements were made in duplicate. The temperature of 

the sample continued to rise throughout the measurement even though a steady reflux was 

observed under vacuum. This is an indication of sample decomposition. 

Vapor Pressure by Isoteniscone 

The determination of the vapor pressure by isoteniscope followed ASTM method D2879-10 

(Reference 3) and was outsourced to an Impact Analytical approved laboratory. 

IA Project P11-0744 2 of 10 pages IA Report R11-0778 
Results and Discussion 

HPLC-UV for Ko, Determination 

The determination of Ko,v for xylene sulfonic acid was conducted following ASTM method E 

1147-92 (Reference 1). Known KoW values were obtained from several sources (References 4 

through 7). An internal standard (2, 5-dihydroxy-p-benzene disulfonic acid, dipostassium salt) 

was used to provide a reference retention time (to) for the retention time of the reference 

materials (tr) and for the xylene sulfonic acid sample. A plot of log Or - to) versus log Ko, was 

generated for the Ko, determination. 

Table I lists the reference compounds that were analyzed and the corresponding known KoW 

values from the literature . The octanol-water partition coefficient (KoW) for xylene sulfonic acid 

sample was calculated to be 1 .37 from the standard plot . Xylene sulfonic acid was observed as a 

mixture of several isomers. An average retention time of the two largest chromatographic peaks 

was used to calculate the retention time of xylene sulfonic acid for the determination of the KoW 

value. 

The HPLC-UV chromatograms of the sample and reference compounds are shown in Figure 1 . 

The HPLC-UV chromatogram of the sample without any reference compounds is shown in 

Figure 2. The plot of log (tT - to) versus log Ko, for the determination of the octanol-water 

partition coefficient (Ko,) for xylene sulfonic acid is shown in Figure 3 . 

Boiling Point Determination 

The boiling point determination followed ASTM method E 1719-05 (Reference 2). A stirred 

flask ebulliometer was used, and the sample decomposed below the boiling point, so a boiling 

point could not be reported. 

Vapor Pressure by Isoteniscope 

The raw data from the vapor pressure by isoteniscope of xylene sulfonic acid; lot# N35P79 is 

provided in Table 11 . A plot of the data is provided in Figure 4. The plot shows a non-linear 

portion near the low temperature end. This is the initial decomposition temperature of the 

sample, 30 °C . 

IA Project P11-0744 3 of 10 pages IA Report R11-0778 
References 

1 .) ASTM International, "Standard Test Method for Partition Coefficient (N-Octanol/Water) 

Estimation by Liquid Chromatography," Designation : E 1147-92, Reapproved 2005 . 

2 .) ASTM International, "Standard Test Method for Vapor Pressure of Liquids by 

Ebulliometery," Designation : E 1719-05. 

3 .) ASTM International, "Standard Test Method for Vapor Pressure-Temperature 

Relationship and Initial Decomposition Temperature of Liquids by Isoteniscope," 

Designation : D2879-10. 

4 .) Qiao, Y. Xia, S. Ma, P, "Octanol/Water Partition Coefficient of Substituted Benzene 

Derivatives Containing Halogens and Carboxyls: Determination Using the Shake-Flask 

Method and Estimation Using the Fragment Method," J. Chem. Eng. Data, Vol 53, 2008, 

pp . 280-282. 

5.) Webpage, "p-Toluenesulfonic Acid MSDS,° www.chemblink.com, 28 December 2011 . 

6.) Webpage, "Phenol Acid MSDS," www.inchem.org, 28 December 2011 . 

7.) Mackay, D. ; Bobra, A. ; Shiu, W.Y., "Relationships between aqueous solubility and 

octanol-water partition coefficients," Chemosphere, Vol. 9, 1980, pp. 701-711 . 

* This analysis is provided in good faith with no warranty expressed or implied. MMI and Impact Analytical assume no obligation or liability 

with respect to the use of the results. If you have questions about this analysis, please contact the lead analyst or the Impact Analytical 

Business Manager at (989)-832-5555, ext. 563. 

IA Project P11-0744 4 of 10 pages IA Report R11-0778 
Table 1 . List of Reference Materials Used for HPLC-UV Analysis According to 

ASTM Method E 1147-92, with Retention Times and Known KoW Values 

Compound log Or - to) tr - t

. a (min)' 

Retention 

time 

(min) 

~w Reference 

No. 

p-Toluene sulfonic acid 

monohydrateb 0.415 2 .6 5.3 0 .90 4 

Phenoxyacetic acid, 98+% 1 .18 15 .0 17.7 1 .26 2 

Phenylacetic acid 1 .24 17 .3 20.0 1 .41 2 

Phenol 1 .03 10.7 13 .4 1 .46 5 

2,6-Difluorobenzoic acid 0.832 6.8 9.5 1 .59 3 

2-Fluorobenzoic acid 1 .12 13 .1 15 .8 1 .77 3 

Benzoic acid 1 .22 16.6 19.3 1 .87 2 

Salicylic acid 1 .30 20.0 22 .7 2.26 2 

a The internal standard of 2,5-dihydroxy-p-benzene disulfonic acid, dipostassium salt, had a 

retention time of approximately 2 .7 minutes . 

bThe sample solution afforded two large chromatographic peaks with retention times of 8.5 and 

10 .9 that were averaged and used for the KoW determination. 

IA Project P11-0744 5 of 10 pages IA Report R11-0778 
Table 11 . Raw Data of the Vapor Pressure Determination of Xylene Sulfonic Acid, 

Lot N35P79 (S11-2023) 

Measured 

Temperature (°C) 

Measured Vapor 

Pressure (mm Hg) 

Temperature 

(1/K) 

Log Vapor Pressure 

(mm Hg) 

50 36 .4 0.003095 1 .561 

40 30 .1 0.003193 1 .479 

30 25.3 0.003299 1 .403 

20 22.2 0.003411 1 .346 

IA Project P11-0744 6 of 10 pages IA Report R11-0778 
Intens. 

mAU 

9 .5 

2.7 

750 

Internal 

Standard 

500 

250 

13 .4 

15 .8 

17 .7 

22.7 

20.0 

8.5 

5.3 19 .3 

10.9 

LLN 

V~- r 

. 

\' I 

I I 

I 

Sample components 

-250 

compound retention 

time 

p-toluene sulfonic 

acid monh drate 5 .3 

phenol 13 .4 

phenoxyacetic acid, 

98+% 17 .7 

benzoic acid 19 .3 

phenylacetic acid 20.0 

salicylic acid 22.7 

2,6-difluorobenzoic 

acid 9 .5 

I 2-fluorobenzoic acid I 15 .8 

Time [min] 

Figure 1 . HPLC-UV chromatogram of a solution of xylene sulfonic acid, Lot N35P79 

(S11-2023) and reference materials. Additional chromatograms of 2,6-difluorobenzoic acid and 

2-fluorobenzoic acid were obtained separately to afford additional datapoints for the plot of log 

(tr - to) versus log Ka , 

IA Project PI 1-0744 7 of 10 pages IA Report RI 1-0778 
Intens. 

mAU 

750- 

500 

250- 

AL 4% 

Sample components 

-250- 

28DEC11000003.D: UV Chromatogram, 210 nm 

0.0 2.5 5.0 7.5 10 .0 . '12.5 . . . . 15.0. f 17 .5 20 .0 22 .5 Time [min] 

Figure 2. HPLC-UV chromatogram of xylene sulfonic acid, Lot N35P79 (S11-2023) without 

any reference compounds. Different chromatographic methods were used during method 

development. The method was optimized for analysis, showing different retention times. 

IA Project P11-0744 8 of 10 pages IA Report R11-0778 
Octanol-Water Cofficient of Xylene Sulfonic Acid 

Reference Curve 

2 .5 ; 

b 

Y 

0 

1 .5 

0 .5 , 

y = 0.9891x+ 0.5352 

0 0.2 0.4 0.6 0.8 1 1.2 1 .4 

log (tr-to) 

Figure 3. Plot of log (tr - to) versus log KoH, for the deterniination of the octanol-water partition 

coefficient (Ko,) for xylene sulfonic acid, Lot N3 5P79 (S11-2023). 

IA Project P11-0744 9 of 10 pages IA Report R11-0778 
1 .60 

1 .55 

= 1 .50 

E 

E 

a> 

N 1 .45 

L 

1 .40 

1 .35 

1 .30 ` 

0 .00300 0.00320 0.00340 0 .00360 

Temperature (1/K) 

Figure 4. Plot of vapor pressure measurements (log pressure versus 1 /temperature) for xylene 

sulfonic acid, Lot N3 5P79 (S11-2023). Data from Table II . 

IA Project P11-0744 10 of 10 pages IA Report R11-0778 
Nease Corporation 

4480 Lake Forest Drive 

Suite 312 

Cincinnati, OH 45242 

, p $006.600 

000,685F,4- FEF 23 20 

MA.~LEJ FROM L',aCODE q52 

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