# .**~ALBEMARLE®** Albemarle Corporation 451 Florida Street Telephone: 225-388-8011 Baton Rouge, Louisiana 70801-1765 Facsimile: 225-388-7686

June 29, 2012

VIA OVERNIGHT MAIL

Document Control Office (7 407M) Office of Pollution Prevention and Toxics (OPPT) Environmental Protection Agency 1201 Constitution Ave., N.W. Washington, DC 20004-3302

Attn: TSCA Section 4 tJ 

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### OPPT CB!C


## 2012 JUL -6 

## AH II: 00

In compliance with the final rule, "Testing of Certain High Production Volume Chemicals; Second Group of Chemicals", 76FR1067, January 17, 2011, Albemarle Corporation and Lonza Inc submit these Studies to meet the end points listed below for "Benzenediamine, ar,ar-diethyl-ar-methyl-", CAS number 68479-98-1.

One paper copy and one electronic copy are provided for each study. Robust summaries of submissions for each end point are also attached.

A3

- Vapor Pressure A4

- n-octanollwater partition coefficient A5

- Water solubility C1

- Aquatic toxicity: Acute Toxicity to Fish Acute Toxicity to Daphnia

The submission of these studies completes the testing requirements for the listed end points under the test rule for this substance. The only outstanding end point for this chemical is F1

- Developmental Toxicity Study. The preliminary range finding study for developmental effects is in progress. Please contact me at 225-388-7776 if you have any questions.

### Sincer~"-""

# ~oudreaux Regulatory Advisor

cc: Paul Campanella (w/o attachments) Chemical Control Division (7405M) Office of Pollution Prevention and Toxics Environmental Protection Agency 1200 Pennsylvania Ave., N.W. Washington, DC 20460-0001

Via email Wayne Chu (Lanza) 1111111111111111111111111111111111111111111111111111111111111111 4 0 1 2 0 0 0 0 0 7 6



## CONTAINS NO CBI.u:1:.ul:_,UJwa..:.:2wa.uwa:fecEX_NEWExpres;US8 9 9 6 6 9 7 4099 2Ill11111111IIIIIIIFromThisporti_nem-ovedforRecipient'srecords.4ExpressPat.Empl21151005JUL12DCAA5!5Cl/E052/AA44__FedEx8 9 9 6 6 9 7 4099 2Date0?J-_j...b._..e._rNOTE:Serviceorderhaschanged.Pleaseselectcarefully.NextBusmessDay/Sender's;/Name1,t\7";'.·(,,.--,·-,--.,/L.-FedExFirstOvernightf;2('L'(,'(.:•\1'XPhone.t5S:-/f'JIlbEarliestnextbusmessmornmgdettverytoselect•·locattonsFndayshtpmentswtilhenPitvererlonCompany•...UFM/-\J::i...:-.·r..Address/!r·i;:rFMondayunlessSATURDAYDeltverytsselected,--...s'rfExPriorityOvernightbusmessmornmg'Frtdaysh1pmentsw1llbedelrveredonMondaySATURDAYDel1veryrsselectedcFedExStandardOvernightNer1busmessafternon•1'SaturdayDellveryNOTavJri<Ji''eFelixExpressFreightUSAirbi/1.2or3BusinessDaysNEWFedEx2DavA.M.SaturdayDetiveryNOTavatlableFedExExpressSaverThrrdbusu•essd,ry•SaturdayDelrvfH\1NOTDeptJHoor/Surte!Room-------------------------------------------------------------Q!y_·!--!..i!'-!H)0.i.::StateZIPBoxTube'o--t"""''\!''•5Packaging*Declaredvaluelimlt$500.A.,;_.1'--{,.:..1Envelope*FedExPak*FedExFedEx[ther.'..33To_,16SpecialHandlingandDeliveryOptions2YourInternalBillingReferenceReciprent"s.L,1;:0::;;.,-;l_-Name-4.Phone..;_'jf3(.'CQrlljlarl'L_'L•HOLDWeekdayFedExlocatmnaddressREQUIREDNOTavailabletorFedExF1rstOvernrghtr,,DirectSignature_jDoesthisshipmentcontaindangerousgoods?OneboxmusthecheckP.d'ad!1ress.snmeonentanerghborrngad!1ressmaysrgnlordehveryForresrdentraldPirverresonlyFeeapplill&Dept.Jfloor/Surte/Room,I.fHOLDSaturdayFildExlocaMnaddressREI1UIREDAvaitabteONLYtorFildExPnontyOvernrghtandHldEx2DaytoselectlocahonsYesYes\.i[»6Asperattacl1edShrpper'sDe_claratmn'·y'--·Shtpper'sOeclaratiOni'retrequlr'edLJ1845kgAddress4------J..-/!-1·1,t:_Useth1slrnelortheHOLDlocatronaddressorCi!Y\.1;,,[J,!J..'{.Stater)(.....v).....ZIPJLIIIIIIRnIIIIIII899669740992''1-;>.J(._.,...,-.:.:.1·-/1:..?-';'.Dangerousgoodstmrrrrl1mgdry1ce1nrlf1Fe!1Expaekagrngorplacedr11aFedExExpressDropBox7PaymentBillto:CargoAircraftOnlyco00G)"?,tn00Eiwwwt.OTEST SUMMARY

NAME OF STUDY, AUTHORS, TEST LABORATORY, STUDY NUMBER, DATE: Determination ofthe Vapor Pressure ofDiethyltoluene Diamine (DETDA) William R. Schutt, B.S. Willard B. Nixon, Ph.D. Wildlife International, Ltd. Project number: 471C-146 June 27, 2012

TEST MATERIAL: Diethyl-toluenediamine (DETDA; Ethacure 1 00)

CAS NUMBER: 68479-98-1

GUIDELINES FOLLOWED: OPPTS 830.7950 OECD Guideline 104

STUDY OBJECTIVES: Determination of the vapor pressure ofDETDA 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 system 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 pumps and the test material was introduced into the evacuated system. The pressure increase 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.

DOSE LEVELS (NOMINAL AND MEASURED): N/A

RESULTS: 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 consistent with published values. The mean measured vapor pressure of the test substance, DETDA, by the static method was 32.4 ± 2.8 Pa at 20 ± 1 °C.



### CONTJ\INS NO CBICONCLUSIONS: 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.

### TEST SUMMARY

NAME OF STUDY, AUTHORS, TEST LABORATORY, STUDY NUMBER, DATE: Determination of the n-Octanol/Water Partition Coefficient of Diethyltoluene Diamine (DETDA) by the Shake Flask Method William R. Schutt, B.S. Willard B. Nixon, Ph.D. Wildlife International, Ltd. Project number: 471C-143 June 27, 2012

TEST MATERIAL: Diethyl-toluenediamine (DETDA; Ethacure 1 00)

CAS NUMBER: 68479-98-1

GUIDELINES FOLLOWED: OPPTS 830.7550 OECD Guideline 107

STUDY OBJECTIVES: Experimental determination of the n-octanol/water partition coefficient of DETDA by equilibrating the test substance in a two-phase system of n-octanol/water by the flaskshaking method and analyzing the two phases by appropriate analytical methodology.

EXPERIMENTAL DESIGN: The n-octanol/water partition coefficient of DETDA was determined using the flaskshaking method. The method consisted of shaking the solute (DETDA) with the two immiscible solvents (n-octanol and HPLC-grade reagent water) at 25 ± 1 °C over a period of time (15 minutes) and analyzing the n-octanol and aqueous phases for the solute concentration using HPLCIUV. The concentration ofDETDA in each partition phase was maintained at less than 0.01 M. A feasibility trial was performed at an n-octanol/water volume ratio of 1:1 (v/v) to confirm that the shake flask experimental design was appropriate for the test substance and to provide an estimate of appropriate solvent ratios for the definitive test. The definitive portion of the test was conducted at three noctanol/water solvent ratios.

DOSE LEVELS (NOMINAL AND MEASURED): Nominal concentration: 4.00 mg DETDA/mL Mean measured test concentration: 3.95 mg DETDA/mL (n = 3)

RESULTS: The feasibility trial at a 1: 1 n-octanol/water volume ratio yielded a mean estimated partition coefficient of 21.8 (log P = 1.34). Based on these results, it was concluded that

ow



### CONTA!NS NO CBrthe n-octanol to water volume ratio of 1:1 would be appropriate for use in the definitive
test.

Prior to the definitive test, the measured pH of the reagent water (saturated with noctanol) was 8.57. The measured pH value of the aqueous phase from a selected partition sample was 8.53.

The total mass recovered was calculated for each of the six definitive test vessels. Mass balance was obtained for DETDA in all vessels. The overall mean percent recovery for DETDA for the six partition test vessels was 101 ± 2.4%.

Partition coefficients were calculated from the measured concentrations of DETDA in each phase for each of six samples. Overall mean n-octanollwater partition coefficients and overall mean of the logarithm (base 

### 1 0) of the n-octanollwater partition coefficients

were calculated for each of the six samples. The mean P values for DETDA at n- ow octanol/water solvent ratios of 1:1, 1:2 and 1:4 were determined to be 23.3, 24.9 and 24.0, respectively.

CONCLUSIONS: The n-octanol/water partition coefficient of DETDA at 25°C, expressed as the logarithm (base 1 0), was determined to be 1.3 8 ± 0.019 (n = 6, CV = 1.4% ).

### TEST SUMMARY

NAME OF STUDY, AUTHORS, TEST LABORATORY, STUDY NUMBER, DATE: Diethyltoluene Diamine (DETDA): Determination of Water Solubility by the Shake Flask Method William R. Schutt, B.S. Willard B. Nixon, Ph.D. Wildlife International, Ltd. Project number: 4 71 C-144 March 19, 2012

TEST MATERIAL: Diethyl-toluenediamine (DETDA; Ethacure 1 00)

CAS NUMBER: 68479-98-1

GUIDELINES FOLLOWED: OPPTS 830.7840 OECD Guideline 105

STUDY OBJECTIVES: Experimental determination of the water solubility of DETDA in reagent water at 20°C using the shake flask method.

EXPERIMENTAL DESIGN: A preliminary test was conducted to estimate the water solubility. An excess amount of the test substance was shaken in the presence of reagent water at 20°C and sampled after

a 24-hour period. The definitive test consisted of shaking an excess amount of test substance with reagent water at an elevated temperature (30°C) for 24, 48, and 72 hours followed by equilibration at 20°C for 24 hours prior to analysis and quantitation of soluble test substance in the aqueous phase of the saturated solution.

DOSE LEVELS (NOMINAL AND MEASURED): N/A

RESULTS: In the preliminary trial the mean measured test substance solubility under the test condition was 21.5 mg DETDA/mL +/- 0.25 mg DETDA/mL (CV 

### = 1.1%, N 

### = 3). Based

on this finding, the target nominal concentration for DETDA in the definitive test was set at a concentration of 131 mg/mL.

The pH of the test system water and samples was evaluated concurrent with the definitive solubility test. The pH of the test system (reagent) water at 20°C was 8.50. The measured pH from the diluted supernatant of reagent water saturated with DETDA at 19.6, 23.1, and 22.3 mg DETDA/mL at 20°C was 9.45, 9.14, and 9.18, respectively.



### CONTAINS NO CBf

### Mean measured water-soluble DETDA concentrations for saturation samples were well within the 15% difference criterion of the protocol (3.3%).

CONCLUSIONS: The mean water solubility (n 

### = 6) for DETDA at 20 °C was 22.7 mg DETDA/mL +/- 

### 0.44 mg DETDA/mL (CV 

### = 2.0%).TEST SUMMARY

NAME OF STUDY, AUTHORS, TEST LABORATORY, STUDY NUMBER, DATE: Diethyltoluene Diamine (DETDA): A 96-Hour Static Acute Toxicity Test with the Fathead Minnow (Pimephales promelas) DanielS. Brougher, M.S. Timothy Z. Kendall, M.S. Sean P. Gallagher, B.S. Henry 0. Krueger, Ph.D. Wildlife International, Ltd. Project number: 471C-123 March 26, 2012

TEST MATERIAL: Diethyl-toluenediamine (DETDA; Ethacure 1 00)

CAS NUMBER: 68479-98-1

GUIDELINES FOLLOWED: OPPTS 850.1075 OECD Guideline 203

STUDY OBJECTIVES: Determination of the acute effects of Diethyltoluene Diamine (DETDA) on the fathead minnow (Pimephales promelas) during a 96-hour exposure period under static test conditions.

EXPERIMENTAL DESIGN: Fathead minnows were exposed to a geometric series of five test concentrations and a negative control (dilution water) for 96 hours under static conditions. Two replicate test chambers were maintained in each treatment and control group, with 1 0 fish in each test chamber, for a total of 20 fish per concentration.

Fathead minnows were impartially assigned to exposure chambers at test mttiatiOn. Observations of mortality and other signs of toxicity were made approximately 2, 24, 48, 72 and 96 hours after test initiation. Cumulative percent mortality observed in the
treatment groups was used to determine LC50 values at 24, 48, 72 and 96 hours. The nomortality concentration and the no-observed-effect concentration (NOEC) were determined by visual interpretation of the mortality and biological observation data.

DOSE LEVELS (NOMINAL AND MEASURED): Nominal concentrations: 7.5, 15, 30, 60 and 120 mg a.i./L. Mean measured test concentrations: 7.2, 15, 29, 70 and 106 mg a.i./L.



### CONTAINS NO CP'RESULTS: Water temperatures were within the 22 ± 1 

# oc range established for the test. Dissolved
oxygen concentrations remained**~6.1** mg/L**(~70%** of saturation) throughout the test. Measurements of pH ranged from 8.2 to 8.4 during the test. The measurements of hardness, alkalinity and specific conductance in the dilution water at test initiation were typical of Wildlife International, Ltd. well water. Light intensity at test initiation was 695 lux at the surface of the water of one representative test chamber.

All fish in the negative control group appeared normal throughout the test. All fathead minnows in the 7 .2, and 15 mg a.i./L treatment groups also appeared normal throughout the test, with no mortalities or overt signs of toxicity observed. Signs of toxicity observed
among fish in the 29, 70 and 106 mg a.i./L treatment groups included surfacing, loss of equilibrium and lethargy. Percent mortality in the 29, 70 and 106 mg a.i./L treatment groups at test termination was 5, 0 and 20%, respectively. While there was no mortality at the 70 mg a.i./L test concentration, signs of toxicity were noted in the 29 mg a.i./L
treatment group and the single mortality at this concentration could not be precluded as treatment related.

CONCLUSIONS: The 96-hour LC50 value was > 106 mg a.i./L, the highest concentration tested. The 96- hour no-mortality concentration and the NOEC were 15 mg a.i./L.TEST SUMMARY

NAME OF STUDY, AUTHORS, TEST LABORATORY, STUDY NUMBER, DATE: Diethyltoluene Diamine (DETDA): A 48-Hour Static Acute Toxicity Test with the Cladoceran 

### (Daphnia magna) Daniel S. Brougher, M.S. Timothy Z. Kendall, M.S. Sean P. Gallagher, B.S. Henry 

### 0. Krueger, Ph.D. Wildlife International, Ltd. Project number: 471A-122 March 20, 2012

TEST MATERIAL: Diethyl-toluenediamine (DETDA; Ethacure 1 00)

CAS NUMBER: 68479-98-1

GUIDELINES FOLLOWED: OPPTS 850.1010 OECD Guideline 202

STUDY OBJECTIVES: Determination of the acute effects of Diethyltoluene Diamine (DETDA) on the cladoceran, 

### Daphnia magna, during a 48-hour exposure period under static test conditions.

EXPERIMENTAL DESIGN: Daphnids were exposed to a geometric series of six test concentrations and a negative control (dilution water) for 48 hours under static conditions. Two replicate test chambers

were maintained in each treatment and control group, with 10 daphnids in each test chamber, for a total of20 daphnids per concentration.

Daphnids were impartially assigned to exposure chambers at test initiation. Observations of immobility and other signs of toxicity were made approximately 2.5, 24 and 48 hours after test initiation. Cumulative percent immobility observed in the treatment groups was used to determine EC50 values at 24 and 48 hours. The no-immobility concentration and the no-observed-effect concentration (NOEC) were determined by visual interpretation of the immobility and biological observation data.

DOSE LEVELS (NOMINAL AND MEASURED): Nominal concentrations: 0.25, 0.5, 1.0, 2.0, 4.0 and 8.0 mg a.i.IL. Mean measured test concentrations: 0.24, 0.49, 0.98, 1.9, 3.9 and 7.8 mg a.i.IL.

### ~ONTP.INS 

## NO:·;--RESULTS: Water temperatures were within the 20 ± 1 

# oc range established for the test. Dissolved
oxygen concentrations remained 2:8.5 mg/L (2:93% of saturation) throughout the test. Measurements of pH ranged from 8.1 to 8.5. The measurements of hardness, alkalinity, specific conductance and TOC in the dilution water at test initiation were typical of Wildlife International, Ltd. well water. Light intensity at test initiation was 61 7 lux at the surface of the water of one representative test chamber.

Daphnia in the negative control groups appeared normal throughout the test. All daphnids in the 0.24, 0.49, and 0.98 mg a.i./L treatment groups also appeared normal throughout the test, with no immobility or overt signs of toxicity observed. Percent immobility at test termination in the 3.9 and 7.8 mg a.i./L treatment groups was 25 and 70%, respectively. Three daphnids in the 1.9 mg a.i./L treatment group appeared lethargic at test termination, while the remaining daphnids in this treatment group appeared normal throughout the test. Lethargic daphnids were observed in the3.9 mg a.i./L treatment group at test termination, and lethargic daphnids were observed in the 7.8 mg a.i./L treatment group at both the 24-hour interval and at test termination.

CONCLUSIONS: The 48-hour EC50 value was 5.8 mg a.i./L, with a 95% confidence interval of 4.7 to 7.6 mg a.i./L. The slope of the concentration-response curve was 4.616. The no-immobility concentration was 1.9 mg a.i./L and the NOEC was 0.98 mg a.i./L.