N-(1,3-Dimethylbutyl)-N

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OECD SIDS N-(1,3-DIMETHYLBUTYL)-N´-PHENYL-1,4-PHENYLENEDIAMINE 3. ENVIRONMENTAL FATE AND PATHWAYS ID: 793-24-8 DATE: 11.05.2005 Test substance : other TS: Purity > 99 % (see Test substance) Deg. products : Phenylbenzoquinone imine 106-51-4 203-405-2 p-benzoquinone 108-09-8 203-549-6 1,3-dimethylbutylamine 122-37-2 204-538-9 4-anilinophenol 62-53-3 200-539-3 aniline Remark : A blank control (sterile mineral medium only), positive control (aniline as reference compound at 100 mg/l) and 6PPD control (6PPD in pure water at 100 mg/l) in 300 ml were incubated simultaneously. Oxygen consumption resulting from biodegradation of the compounds was measured over 28-day test period using an Okura Electric Closed System Oxygen Consumption measuring apparatus (Coulometer). Percentage biodegradation was calculated based on BOD, TOC and HPLC analysis. The test solutions were maintained in a darkened room at a temperature of 25 ±1 °C and continuously stirred by magnetic stir bars over the 28-day test period. Percent degradation (%) was obtained from the following equations. BOD Degradation (%) = (BOD - B)/ThOD * 100 BOD (mg): BOD in Sludge + 6PPD system B (mg): BOD in Sludge blank ThOD: theoretical oxygen demand required when 6PPD was completely oxidized. HPLC Degradation (%) = (Sw - Ss)/Sw * 100 Sw (mg): Residual amount of 6PPD detected by HPLC in Water + 6PPD system Ss (mg): Residual amount of 6PPD detected by HPLC in Sludge + 6PPD system Result : Analysis of Residual Compounds and Mineralization to CO2 in Biodegradation Test Reactions after 28 Days Water+6PPD Sludge+6PPD Theoretical amount n=1 n=1 n=2 n=3 Mean BOD* (mg) 2.6 3.6 1.3 2.2 2.4 93 Residual 6PPD (mg) 5.1 2.2 2.3 2.3 2.3 30 (by HPLC)(%) 17 7 8 8 7.7 - Residual compound 1,2** (mg) 3.3 13.6 12.9 13.1 13.2 20.7 (by HPLC)(%) 16 66 62 63 64 - Residual compound 3*** (mg) 4.5 0 0 0 0 10.4 (by HPLC)(%) 43 0 0 0 0 - Residual compound 4**** (mg) 10.3 11.0 11.0 11.8 10.9 11.3 (by HPLC)(%) 91 97 98 95 97 - *Results are corrected for corresponding blank values **Compounds 1,2: p-Hydroxydiphenylamine, Phenylbenzoquinone imine ***Compound 3: Aniline ****Compound 4: 1,3-<strong>Dimethylbutyl</strong>amine Biodegradation Test and Reference Material Percent degradation of 6PPD (%) (after 28 days) n=1 n=2 n=3 Mean BOD 4 1 2 2.3 HPLC 93 92 92 92 68 UNEP PUBLICATIONS
OECD SIDS N-(1,3-DIMETHYLBUTYL)-N´-PHENYL-1,4-PHENYLENEDIAMINE 3. ENVIRONMENTAL FATE AND PATHWAYS ID: 793-24-8 DATE: 11.05.2005 Percent degradation of aniline (%) After 7 days After 14 days BOD 64 71 Test condition : Inoculum Sludge samples were collected from the 10 sites such as sewage treatment works, industrial wastewater treatment works, rivers, lakes, and sea throughout Japan and mixed thoroughly. A filtrate (500 ml) of the supernatant of the mixed sludge was then mixed with 5 liters of the filtered supernatant of an activated sludge in the present use. After the combined sludge solution (pH adjusted at 7.0 ± 1.0) was aerated for 30 min, the supernatant corresponding 1/3 of the whole volume was discarded. An equal volume of pure water was then added to the remaining portion and the supernatant (final concentration: 0.1 %) of the resulting sludge solution was mixed with sterile mineral medium and continuously aerated at 25 ± 2 °C to allow minimization of residual dissolved organic carbon according to the procedure outlined in the TG. The test was conducted in triplicate with 6PPD in sterile mineral medium at 100 mg/mL and with a small volume of the activated sludge to give a final MLSS concentration of 30 mg/L in 300 mL. Test substance : Source: Seiko Chemical Co., Ltd., Lot No. 40533, Purity: > 99 %, Impurity: 4-Aminodiphenylamine, N-bis-(1,3-<strong>Dimethylbutyl</strong>)- N-phenyl-1,4-phenylendiamine. The structure was confirmed by IR, NMR and MASS spectrometry. Kept at cold temperature until use. Conclusion : Based on BOD, ca. 2 % of 6PPD was biodegraded; based on HPLC, ca. 92 % of 6PPD was degraded Reliability : (1) valid without restriction Well conducted study, carried out by the Chemicals Evaluation and Research Institute (Kurume, Japan) Flag : Critical study for SIDS endpoint 05.08.2003 (6) Type : Aerobic Inoculum : predominantly domestic sewage Concentration : 100 mg/l related to Test substance related to Contact time : Degradation : 13 - 40 (±) % after 28 day(s) Result : other: not readily biodegradable Deg. product : Method : other: Respirometer-Test, ISO DP 9408, EG Directive 79/831/ Annex V, modified MITI I Test (OECD 301C) Year : 1984 GLP : No Test substance : as prescribed by 1.1 - 1.4 Remark : The large difference between the results of 2 parallel experiments (13 %, 40 %) was explained with the poor solubility of the TS Result : Oxygen consumption of experiment with lower degradation: day BOD of test substance (BOD of aniline)[blank] 4 16 (157) [16] 6 19 (197) [17] 8 23 (220) [19] 10 24 (235) [19] 12 28 (247) [23] 18 30 (249) [23] 20 32 (252) [23] 22 35 (258) [23] 24 41 (269) [23] UNEP PUBLICATIONS 69
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N-(1,3-Dimethylbutyl)-N

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