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## 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 WhomIt May Concern: 

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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method for vapor pressure listed in the OPPTS Harmonized Guidelines (ASTME 1782-08thermal analysis) uses equipment that is obsolete as determined by the outside laboratory (Impact Analytical, Midland, Michigan 48640, PH:989-832-5555) contracted for the testing.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: ASTMD2879-10 3 . N-Octanol/water partition coefficient (log 10 basis) or logKoW by Method B, ASTME 1147-92 (reapproved 2005) (liquid chromatography) .



## CONTAINS NOCBIp. 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 .comif you have any further questions. Sincerely, Philip Benes Director of Technology & Product Development

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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 : WilliamHehemann 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 WilliamHehemann 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 . Astandard 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. Asummary 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) . Astirred 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 fromthe 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 K

oW 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 pagessulfonic acid was conducted following ASTM method E 1147-92 (Reference 1) . Solutions ofthe sample and reference materials were injected into an Agilent 1100 Series high-performance liquid chromatographic (HPLC) systemthat was equipped with a multiple wavelength detector (MWD) . The MWDmonitored a wavelength of 210 nn . Separations were achieved using a 150 x 4.6 mm

Unison UK-C18 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 pHof 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 200mL 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, dipostassiumsalt . 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 2of 10 pages IA Report R11-0778Results and Discussion

HPLC-UV for K

o, 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, dipostassiumsalt) 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. Aplot 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 fromthe literature. The octanol-water partition coefficient (KoW) for xylene sulfonic acid sample was calculated to be 1 .37 fromthe standard plot . Xylene sulfonic acid was observed as a mixture of several isomers. An average retention time ofthe 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-UVchromatogramofthe 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 belowthe boiling point, so a boiling point could not be reported. Vapor Pressure by Isoteniscope The rawdata fromthe vapor pressure by isoteniscope ofxylene 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 R11-0778References

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. Ifyou 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 4of 10 pages IA Report R11-0778Table 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 aThe internal standard of 2,5-dihydroxy-p-benzene disulfonic acid, dipostassiumsalt, had a retention time ofapproximately 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 R11-0778Table 11 . Raw Data of the Vapor Pressure Determination of Xylene Sulfonic Acid,

Lot N35P79 (S11-2023) Measured Tem perature (°C) Measured Vapor

Pressure (mm

H g ) Temperature

(1/K) Log Vapor Pressure

(mm H g ) 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 6of 10 pages IA Report R11-0778Intens. 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 chromatogramof 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 1-0778Intens. mAU

750-

500

250-

AL 4%

Sample components -250- 28DEC11000003.D : UVChromatogram, 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 chromatogramof 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 N35P79 (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 N35P79 (S11-2023) . Data from Table II .

IA Project P11-0744 10 of 10 pages IA Report R11-0778Nease Corporation 4480 Lake Forest Drive Suite 312 Cincinnati, OH 45242



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