DETERMINATION OF THE VAPOR PRESSURE OF DIETHYLTOLUENE DIAMINE (DETDA)

WILDLIFE INTERNATIONAL, LTD. PROJECT NUMBER: 471C-146

U.S. EPA Product Properties Test Guideline OPPTS 830.7950, Vapor Pressure

and

Organisation for Economic C ooperation and Development OECD Guideline 104: Vapour Pressure

AUTHORS:

William R. Schutt, B.S. Willard B. Nixon, Ph.D.

STUDY INITIATION DATE: March 14, 2012

STUDY COMPLETION DATE: June 27, 2012

SUBMITTED TO:

Albemarle Corporation
451 Florida Street Baton Rouge, LA 70801


# Wildlife International, Ltd.

8598 Commerce Drive Easton, Maryland 21601 (410) 822-8600

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TABLE OF CONTENTS

Title/Cover Page .............................................................................................................. ....................... 1

Good Laboratory Practice Compliance Statement ................................................................................. 2

Quality Assuran ce Statement ................................................................................................... .............. 3

Report Approval ............................................................................................................... ...................... 4

Table of Contents ............................................................................................................. ...................... 5

Summary ....................................................................................................................... ......................... 7

Introduction .................................................................................................................. .......................... 8

Objective ..................................................................................................................... ........................... 8

Experimental Design ........................................................................................................... ................... 8

Materials and Methods ......................................................................................................... .................. 8
Test Substance ............................................................................................................... ............ 8
Reference Substance .......................................................................................................... ........ 9 System Configuration ......................................................................................................... ....... 9
Test Procedure ............................................................................................................... ............ 9
Calculations ................................................................................................................. ............ 10

Results and Discussion ........................................................................................................ ................. 10

Conclusions ................................................................................................................... ....................... 11

Refere nces .................................................................................................................... ........................ 12

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TABLE OF CONTENTS
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TABLES

Table 1. Vapor Pressure Measurements and Out-Gassing Rates for Toluene by the Static Method at 20 ± 1°C ...................................................................................... 13

Table 2. Vapor Pressure Measurements and Out-Gassing Rates for DETDA by the Static Method at 20 ± 1°C ...................................................................................... 14

FIGURES

Figure 1. Diagram of high vacuum system configuration ................................................................ 15

Figure 2. Image of the high vacuum system .................................................................................... 16

Figure 3. Representative vapor pressure plot for toluene at 20 ± 1°C ............................................. 17

Figure 4. Representative vapor pressure plot for DETDA at 20 ± 1°C ............................................ 18

APPENDICES

Appendix 1. Protocol ...................................................................................................................... 19

Appendix 2. Characterization Report and Ce rtificate of Analysis .................................................. 31
Test Substance .................................................................................................. 32
Reference Substance ......................................................................................... 35

Appendix 3. Personnel Involved in the Study ................................................................................. 36

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SUMMARY

STUDY TITLE : Determination of the Vapor Pressure of Diethyltoluene Diamine (DETDA)

WILDLIFE INTERNATIONAL

, LTD

. PROJECT NUMBER : 471C-146

SPONSOR : Albemarle Corporation
451 Florida Street Baton Rouge, LA 70801

TESTING FACILITY : Wildlife International, Ltd. Easton, Maryland 21601

SPONSOR ’ S REPRESENTATIVE : Marcia L. Hardy, DVM, Ph.D.

LOCATION OF STUDY

, RAW

DATA AND A COPY OF THE

FINAL REPORT : Wildlife International Ltd. Easton, Maryland 21601

TEST SUBSTANCE : Diethyltoluene Diamine (DETDA)

TEST DATES : Experimental OECD Start – March 26, 2012 Experimental EPA Start – March 26, 2012 Experimental Termination – April 1, 2012

S UMMARY : The mean vapor pressure for DETDA at 20 ± 1°C was 32.4 ± 2.8 Pa (N = 3, CV = 8.7%) using the static method.

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INTRODUCTION

The vapor pressure of diethyltoluene diamine (D ETDA) was determined at 20 ± 1°C using the

static method. The study was conducted by Wildlife International, Ltd. for Albemarle Corporation at the

Wildlife International, Ltd. chemistry facility in Easton, Maryland. Vapor pressure analyses were

conducted from March 26, 2012 to April 1, 2012. Raw data generated by Wildlife International, Ltd. and

a copy of the final report are filed under Project Number 471C-146 in archives located on the Wildlife

International, Ltd. site. The original signed report will be maintained by Albemarle Corporation, Baton

Rouge, Louisiana.

OBJECTIVE

The objective of this study was to determine the vapor pressure of DETDA at 20 ± 1°C.

EXPERIMENTAL DESIGN

The static method is applicable to both liquids and solids with vapor pressures at or above the

upper range of the spinning rotor gauge method (0.5 Pa ). Measurements were performed using a Pirani

capacitance diaphragm manometer. The vacuum syst em and manometer were isolated from the test

substance, maintained at a temperature of 20° ± 1° C, until ultimate vacuum was achieved. The system

and manometer were then isolated from the vacuum pum ps and the test material was introduced into the

evacuated system. The pressure in crease was monitored by the capacitance manometer at approximately

one-second intervals. A linear regression was obtained for pressure increase as a function of time. The

y-intercept of this regression corresponds to the vapor pressure of the sample.

MATERIALS AND METHODS

The study was conducted according to the procedures outlined in the protocol, “Determination of

the Vapor Pressure of Diethyltoluene Diamine (DET DA)” (Appendix 1). The test was performed based

on procedures in the U.S. EPA Product Properties Test Guidelines, OPPTS 830.7950, Vapor Pressure

(1) and OECD Guideline for the Testing of Chemicals, 104: Vapour Pressure (2).

Test Substance

The test substance was received from Albemarl e Corporation on September 21, 2011, and was

assigned Wildlife International, Ltd. identificati on number 10232. The test substance was a liquid

identified as DETDA; Lot number – 4500051816-011110. A purity of 97.27% was obtained from the

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characterization report provided by the Sponsor (A ppendix 2). The test substance was stored under

ambient conditions.

Reference Substance

The toluene reference substance was receive d from Sigma-Aldrich Chemical Company on

August 11, 2006, and was assigned Wildlife Internati onal, Ltd. identificati on number 7688 upon receipt.

The reference standard, a liquid, was identified as: Toluene, anhydrous, 99.8%; lot number 01062LD;

CAS number 108-88-3. The reference standard had a reported purity of 99.84%, and was stored in

darkness under ambient conditions (Appendix 2). An expiration date of August 31, 2012 was assigned.

System Configuration

The high vacuum system consisted of a vacuum chamber configured with a mechanical vacuum

pump (Edwards Model E2M2), a turbomolecular pump (Leybold TURBOVAC 50), a pirani capacitance

diaphragm manometer (Inficon PCG400), all-metal isol ation valves, a sample chamber and miscellaneous

vacuum fittings required to assemble the components. The pirani gauge controller was connected to a

computer via the serial interface (RS-232 port). A diag ram of the apparatus configuration and an image

of the high vacuum system are presented in Figures 1 and 2, respectively.

The sample chamber consisted of a Pyrex tube (~2.5 cm o.d. X 12 cm) joined to a quick-fit type

metal flange (NW-25). Empty sample chambers were used for background measurement. The

temperature of the sample chamber was maintained at 20 ± 1°C during pressure measurements. A

refrigerated recirculator, attached to a copper wate r jacket, regulated the temperature of the sample

chamber. The minimum and maximum temperature of the sample chamber during measurement were

recorded with a NIST-traceable digital thermometer.

Test Procedure

Prior to analysis of the reference or test subs tance, the vacuum system, including the capacitance

manometer, was isolated from the sample chamber and evacuated to achieve ultimate vacuum. Once the

system had achieved ultimate vacuum, the vacuum sy stem was isolated from the vacuum pumps and the

reference or test substance was introduced into the evacu ated system. The rate of pressure increase due to

out-gassing and permeation in the presence of the reference or test material was determined at least three

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times at 20 ± 1°C. Pressure increase was measured for at least fifteen minutes after introduction of the

reference or test material.

A 5.00-mL aliquot of toluene was used as a vapor pressure reference to ve rify the accuracy of the

system configuration. The vapor pressure of the re ference substance by the static method was compared

to the published values by the dynamic method (1).

An approximate 5.00-gram aliquot of the test substance, DETDA, was used for vapor pressure

determination.

Calculations

Least-squares-fit linear regression analysis was performed on the vapor pressure measurements

collected after the valves to the v acuum pump were closed to determine the out-gassing rate. A minimum

of ten data points from the end of the vapor pressure curve with an average rate of change for the

replicates of less than or equal to 0.30% was used for the linear regression of the test substance since it

provided the best linearity. In the absence of sample, the slope of the regression would be equal to the

out-gassing rate of the system, and the y-intercep t would be considered the baseline or background

pressure. With sample present, the sample vapor pr essure was also taken as the y-intercept of the

corresponding regression line.

RESULTS AND DISCUSSION

The mean measured vapor pressure of the reference substance, toluene, by the static method was

2976 ± 51 Pa at 20 ± 1°C. The vapor pressure was cons istent with published values (2). Individual and

mean measured vapor pressures (y-intercept of linear regression function) and the corresponding

out-gassing rates (slope of linear regression function) for the reference substance at 20 ± 1  C are

presented in Table 1. A representative vapor pressu re plot for toluene is presented in Figure 3.

The mean measured vapor pressure of the test subs tance, DETDA, by the static method was 32.4 ±

2.8 Pa at 20 ± 1°C. Individual and mean measured vapor pressures (y-intercept of linear regression

function) and the corresponding out-gassing rates (sl ope of linear regression function) for the test

substance at 20 ± 1  C are presented in Table 2. A representative vapor pressure plot for DETDA is

presented in Figure 4.

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CONCLUSIONS

The mean vapor pressure for DETDA at 20 ± 1°C was 32.4 ± 2.8 Pa (N = 3, CV = 8.7%) using the

static method.

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REFERENCES

1. U.S. EPA Product Properties Test Guidelines. 1996. OPPTS 830.7950. Vapor Pressure.

2. Organisation for Economic Cooperation and Development. 2006. Guidelines for the Testing of Chemicals, 104: Vapour Pressure.

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Table 1

Vapor Pressure Measurements and Out-Gassing Rates for Toluene by the Static Method at 20 ± 1  C

Measured Vapor Pressure (Pa) Min/Max Temperature (°C) Mean
Measured Vapor Pressure 1
(Pa) Standard
Deviation (Pa)

2975

3027 19.6/20.0 2976 51

2925

1 Literature value was 3.0 x 10 3 Pa and range was 2.9 x 10 3 Pa to 3.1 x 10 3 Pa using the dynamic method (2).

Measured Out-gassing Rate (Pa/s) Min/Max Temperature (°C) Mean
Measured Out-gassing Rate (Pa/s) Standard
Deviation

(Pa/s)

7.24 x 10 -3

-8.82 x 10 -2 19.6/20.0 -2.28 x 10 -2 5.67 x 10 -2

1.26 x 10 -2

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Table 2

Vapor Pressure Measurements and Out-Gassing Rates for DETDA by the Static Method at 20 ± 1  C

Measured Vapor Pressure (Pa) Min/Max Temperature (°C) Mean
Measured Vapor Pressure (Pa) Standard
Deviation (Pa)

29.1

34.1 19.9/20.0 32.4 2.8

33.9

Measured Out-gassing Rate (Pa/s) Min/Max Temperature (°C) Mean
Measured Out-gassing Rate (Pa/s) Standard
Deviation

(Pa/s)

1.43 x 10 -3

1.67 x 10 -3 19.9/20.0 1.57 x 10 -3 1.27 x 10 -4

1.62 x 10 -3WildlifeInternational,Ltd.Project Number 471C-146- 15 -1. Vacuum Pump 6. Turbomolecular Pump2. Turbopump Controller 7. Capacitance Manometer3. Capacitance Manometer Controller8. Spinning Rotor Gauge (Not Used)4. Spinning Rotor Gauge Controller (Not Used) 9. Sample Chamber5. Computer WorkstationFigure 1.Diagram of high vacuum system configuration.

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Figure 2 . Image of the high vacuum system.

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-1.0E-04 5.0E+02 1.0E+03 1.5E+03 2.0E+03 2.5E+03 3.0E+03 3.5E+03

8:52:48 9:07:12 9:21:36 9:36:00 9:50:24 

## TimePascal

Figure 3 . Representative vapor pressure plot for toluen e at 20 ± 1°C. Arrow indicates time of valve closing (vacuum isolation) and introduction of sample into the evacuated system. 9:10:08

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-1.0E-04 5.0E+00 1.0E+01 1.5E+01 2.0E+01 2.5E+01 3.0E+01 3.5E+01

7:55:12 8:09:36 8:24:00 8:38:24 8:52:48 

## TimePascal

Figure 4 . Representative vapor pressure plot for DETDA at 20 ± 1°C. Arrow indicates time of valve closing (vacuum isolation) and introduction of sample into the evacuated system. 8:10:07

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Appendix 1

Protocol

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Appendix 2

Characterization Report and Certificate of Analysis

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Test Substance

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Reference Substance

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Appendix 3

Personnel Involved in the Study

The following key Wildlife International, Ltd. personnel were involved in the conduct or

management of this study:

1. Willard B. Nixon, Ph.D., Director of Chemistry

2. Raymond L. Van Hoven, Ph .D., Senior Scientist

3. William R. Schutt, B.S., Chemist