平成25年度 化学物質分析法開発報告書
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1 2,4-2,4-Dimethylaniline 2,4-2,4-Xylidine CH 3 CH 3 CAS C 8 H 11 N C 2) 214 C 2) g/cm 3 2) mmhg (25 C) 1) 1390 mg/l (25 C) 1) mg/l 25 C WSKOWWIN 5) mg/l 25 C 5) log P ow 1.68 (ph = 7.5) 3) pka 4.89 (25 C) 4) NH 2 282
2 LD mg/kg 3) LD mg/kg 3) LC mg/m 3 (7hr) 7) Leuciscas idas melanotus (48h) LC mg/l 4) 出典 : 1) Philip H. Howard, William M. Meylan, Handbook of Properties of Organic Chemcals 2) Lide, D.R,(ed), CRC Handbook of Chemistry and Physics 84th Edition 3) Hansch, C., A. Leo and D. Hoeckman(1995): Exploring QSAR-Hydrophobic, Electronic, and Steric Constants, Washington DC,ACS Professional Reference Book:45 4) Supelco MSDS 5) U. S. Environmental Protection Agency, WSKOWWIN TM v ) Meylan,W. M., P. H. Howard and R. S. Boethling(1996): Improved method for estimating water solubility from octanol/water partition coefficient :Environ. Toxicol. Chem. 15:-106 7) US National Institute for Occupational Safety and Health, Registry of Toxic Effects of Chemical Substances (RTECS) Database 1 (1) 0.01 mol/l -70% 2 GC/MS-SIM /(8:2) 0.01 mol/l -70% 1 mol/l 283
3 -10% 2 GC/MS-SIM (2) 2,4- Supelco 99.9% -2,3,4,5,6-d 5 CIL 99% Milli-Q JISK0557(1998) A4 Waters Sep-Pak Plus PS-2 Agilent Bond Elute PRS,500 mg 3 ml 0.01 mol/l -70%PS-2 50 μl 50 ml 35 ml 50 ml 0.5 mol/l 15% 10 g 75 g 500 ml ml mol/l -PRS 50 μl 50 ml 50 ml 1 mol/l -10%PRS 284
4 3.7 g 50 ml 30 ml 5 ml 50 ml 0.1 mol/l -10% 2.0 g 50 g 500 ml 1 L ml mg10 ml 1.00 mg/ml 1.00 μg/ml 1.00 μg/ml -d mg 10 ml 1.00 mg/ml 1.00 μg/ml ng/ml -d ng/ml (10 ml) (50 ml) (10 ml) (1 L, ml) 285
5 Sep-Pak Waters Waters TAITEC (3) ml 10 ml 20 ml 10 ml 20 ml mol/l 70% 3 ml 0.5 mol/l 15% 8 ml 4 ml g 1 4 ml 10.0 ng/ml 10 ml GC/MS 20 g 50 ml / (8:2) 20 ml rpm 10 ml / (8:2) 20 ml ml ml 10 ml 20 ml 10 ml 20 ml
6 5 ml 0.01 mol/l - 2 ml 0.01 mol/l- 70% 3 ml 0.01 mol/l - 2 ml 30 1 mol/l -10% 2 ml 0.5 mol/l -15% 8 ml 4 ml g 1 4 ml 10.0 ng/ml 10 ml GC/MS GC/MS GC/MS GC6890Agilent MS5973Agilent Supelco SUPELCOWAX m0.25 mm, 0.25 μm 50 C (1 min) 20 C /min 130 C (0 min) 3 C /min 163 C (0 min) 20 C /min 260 C (1 min) 1.0 min 210 C He (1.0 ml/min) 35 cm/sec 2 μl 270 C 230 C 150 C EI 70 ev 287
7 SIM 2,4- m/z m/z 120.0m/z d 5 m/z μl GC/MS 2 μl GC/MS C (ng/l) C RQ/V R : Q : (ng) = (ng/ml) (ml) V : (L) Q =.0 (ng) = (10.0 ng/ml) (10.00 ml) V = 0. (L) C = R 500 (ng/l) C (ng/g-dry) C RQ/V 288
8 R : Q : (ng) = (ng/ml) (ml) V : (g-dry) Q =.0 (ng) = (10.0 ng/ml) (10.00 ml) C = R /V (ng/l) (IDL) GC/MS IDL IDL IDL *1 (ng/ml) (ml) IDL * , *1 L g-wet *2 ng/l ng/g-wet (MDL) (MQL) MDL MQL MDL MQL *1 MDL *2 MQL *2 (ml) , *1 L g-wet 68.6% *2 ng/l ng/g-dry 289
9 1 2IDL IDL N- (N-EA) N--o- (N-Me-o-T) N--p- (N-Me-p-T) N--m- (N-Me-m-T) 2,6- (26XLD) o- (o-ea) (L) (ml) (ng/ml) (μl) (ng/ml) (ng/ml) (ng/ml) (ng/ml) (ng/ml) (ng/ml) (ng/ml) (ng/ml) (ng/ml) IDL (ng/ml) * IDL (ng/l) IDL (ng/g-wet) S/N CV (%) *: IDL = t (n-1, 0.05) σ n
10 2,4- (24XLD) 3-2 IDL 2,5- (25XLD) p- (p-ea) m- (m-ea) 3,5- (35XLD) 2,3- (23XLD) 3,4- (34XLD) (L) (ml) (ng/ml) (μl) (ng/ml) (ng/ml) (ng/ml) (ng/ml) (ng/ml) (ng/ml) (ng/ml) (ng/ml) (ng/ml) IDL (ng/ml) * IDL (ng/l) IDL (ng/g-wet) S/N CV (%) *: IDL = t (n-1, 0.05) σ n
11 イオン ( ~ ): _1ppb_1.D\data.ms N-Me-mT 24XLD p-ea 35XLD N-Me-oT 26XLD m-ea 25XLD 23XLD o-ea N-EA N-Me-pT 34XLD イオン ( ~ ): _1ppb_1.D\data.ms イオン ( ~ ): _1ppb_1.D\data.ms イオン (97.50 ~ 98.50): _1ppb_1.D\data.ms d 5 1 IDL (2 pg) 292
12 3MDL MQL MDL MQL N- (N-EA) N--o- (N-Me-o-T) N--p- (N-Me-p-T) N--m- (N-Me-m-T) 2,6- (26XLD) o- (o-ea) (L) (ng) (ng/l) (ml) (ng/ml) (μl) (ng/l)* 1 ND ND ND ND ND ND (ng/l) *2 ND ND ND ND ND ND 1 (ng/l) (ng/l) (ng/l) (ng/l) (ng/l) (ng/l) (ng/l) (ng/l) (ng/l) MDL (ng/ml) * MQL (ng/ml) * S/N CV (%) *1(n=1) *2MDL (n=1) *3MDL = t (n-1,0.05) σ n-1 2 *4MQL = σ n
13 4-2 MDL MQL 2,4- (24XLD) 2,5- (25XLD) p- (p-ea) m- (m-ea) 3,5- (35XLD) 2,3- (23XLD) 3,4- (34XLD) (L) (ng) (ng/l) (ml) (ng/ml) (μl) (ng/l)* 1 ND ND ND ND ND ND ND (ng/l) *2 ND ND ND ND ND ND ND 1 (ng/l) (ng/l) (ng/l) (ng/l) (ng/l) (ng/l) (ng/l) (ng/l) (ng/l) MDL (ng/l) * MQL (ng/l) * S/N CV (%) *1(n=1) *2MDL (n=1) *3MDL = t (n-1,0.05) σ n-1 2 *4MQL = σ n
14 (120.50~121.50): _L1_2.D\data.ms 35XLD N-Me-oT N-Me-mTo-EA 25XLD N-EA 24XLD m-ea 23XLD N-Me-pT 26XLD p-ea 34XLD (119.50~120.50): _L1_2.D\data.ms (105.50~106.50): _L1_2.D\data.ms (97.50~98.50): _L1_2.D\data.ms 400 -d MDL 295
15 5-1 MDL MQL N- (N-EA) N--o- (N-Me-o-T) N--p- (N-Me-p-T) N--m- (N-Me-m-T) 2,6- (26XLD) o- (o-ea) (g-dry) (ng) (ng/g-dry) (ml) (ng/ml) (µl) (ng/g-dry)* 1 ND ND ND ND ND ND (ng/g-dry) *2 ND ND ND ND ND ND 1 (ng/g-dry) (ng/g-dry) (ng/g-dry) (ng/g-dry) (ng/g-dry) (ng/g-dry) (ng/g-dry) (ng/g-dry) (ng/g-dry) MDL (ng/g-dry) * MQL (ng/g-dry) * S/N CV (%) *1(n=1) *2MDL (n=1) *3MDL = t (n-1,0.05) σ n-1 2 *4MQL = σ n
16 5-2 MDL MQL 2,4-2,5-3,5- p- m- (p-ea) (m-ea) (24XLD) (25XLD) (35XLD) 2,3- (23XLD) 3,4- (34XLD) (g-dry) (ng) (ng/g-dry) (ml) (ng/ml) (μl) (ng/g-dry)* 1 ND ND ND ND ND ND ND (ng/g-dry) *2 ND ND ND ND ND ND ND 1 (ng/g-dry) (ng/g-dry) (ng/g-dry) (ng/g-dry) (ng/g-dry) (ng/g-dry) (ng/g-dry) (ng/g-dry) (ng/g-dry) MDL (ng/g-dry) * MQL (ng/g-dry) * S/N CV (%) *1(n=1) *2MDL (n=1) *3MDL = t (n-1,0.05) σ n-1 2 *4MQL = σ n
17 m/z 121 NN-DMA m/z 120 m/z 106 イオン ( ~ ): _MDL_A.D\data.ms 26XLD N-Me-o-T o-ea 25XLD N-Me-m-T 35XLD 24XLD N-EA N-Me-p-T m-ea 23XLD p-ea 34XLD イオン ( ~ ): _MDL_A.D\data.ms イオン ( ~ ): _MDL_A.D\data.ms イオン (97.50 ~ 98.50): _MDL_A.D\data.ms m/z 98 -d 5 -d 5 3 MDL 298
18 ml 20 ml Sep-Pak Plus PS-2 10 ml/min mol/l- 70% 3 ml 0.5 mol/l- 15% 8 ml 4 ml g GC/MS-SIM 10 ml -d5 ng
19 2 20 g-wet /(8:2) 20 ml rpm10 10 ml 20 ml Sep-Pak Plus PS-2 10 ml/min 30 Bond Elute PRS 0.01 mol/l- 70% 3 ml Sep-Pak Plus PS mol/l- 2 ml 30 1 mol/l- 10% 2 ml mol/l- 15% 8 ml 4 ml g GC/MS-SIM -d5 ng 10 ml
20 ,4- (A s ) (ng/ml) 2,4- (A is ) (A s /A is ) (C s ) (m/z 121) -d 5 (m/z 98) *10.0 ng/ml (ng/ml) (0.5)(1)(2) (5) (10) (ng/ml) (10) (20) (50) () () ng/ml10 ng/ml 301
21 2, NN- DMA イオン ( ~ ): _5ppb_1.D\data.ms N-Me-pT o-ea N-Me-mT 25XLD 35XLD N-Me-oT - -24XLD 23XLD m- EA 26XLD N-EA 34XLD p-ea イオン ( ~ ): _5ppb_1.D\data.ms イオン ( ~ ): _5ppb_1.D\data.ms イオン (97.50 ~ 98.50): _5ppb_1.D\data.ms d ng/ml) 302
22 2,4- ng/ml -d スキャン 1395 (9.602 min): scan_24xldppb_d_1.d\data.ms (-1344) (-) m/z--> ,4- スキャン 2570 ( min): SCAN_ANILINED5.D\data.ms (-2487) (-) m/z--> d 5 303
23 イオン ( ~ ): _BL_PS_2_1.D\data.ms 2,4-XLD イオン ( ~ ): _BL_PS_2_1.D\data.ms イオン ( ~ ): _BL_PS_2_1.D\data.ms イオン (97.50 ~ 98.50): _BL_PS_2_1.D\data.ms 400 -d
24 イオン ( ~ ): _BL_1.D\data.ms 55 2,4-XLD 50 イオン ( ~ ): _BL_1.D\data.ms イオン ( ~ ): _BL_1.D\data.ms イオン (97.50 ~ 98.50): _BL_1.D\data.ms -d
25 (ml) (ng) (ng/l) (%) CV (%) 2,4-1 ND ND ND (g-wet) (ng) (ng/ g-wet) (%) CV (%) 2, ND ND ND
26 イオン ( ~ ): _ 茨戸河川水無添加.D\data.ms ,4-XLD イオン ( ~ ): _ 茨戸河川水無添加.D\data.ms イオン ( ~ ): _ 茨戸河川水無添加.D\data.ms イオン (97.50 ~ 98.50): _ 茨戸河川水無添加.D\data.ms
27 (120.50~121.50): _ 茨戸 A_day0.D\data.ms N-Me-o-T o-ea 25XLD N-Me-m-T 35XLD 24XLD N-EA N-Me-p-T 26XLD m-ea 23XLD p ĒA 34XLD (119.50~120.50): _ 茨戸 A_day0.D\data.ms (105.50~106.50): _ 茨戸 A_day0.D\data.ms (97.50~98.50): _ 茨戸 A_day0.D\data.ms -d
28 65 イオン ( ~ ): _ 茨戸無添加 _0227.D\data.ms 2,4-XLD イオン ( ~ ): _ 茨戸無添加 _0227.D\data.ms イオン ( ~ ): _ 茨戸無添加 _0227.D\data.ms イオン (97.50 ~ 98.50): _ 茨戸無添加 _0227.D\data.ms d
29 イオン ( ~ ): _ 茨戸 A_day0.D\data.ms N-Me-oT N-EA N-Me-mT o-ea 25XLD 35XLD 23XLD 26XLD m-ea 24XLD p-ea 34XLD N-Me-pT イオン ( ~ ): _ 茨戸 A_day0.D\data.ms イオン ( ~ ): _ 茨戸 A_day0.D\data.ms イオン (97.50 ~ 98.50): _ 茨戸 A_day0.D\data.ms d ph 1 L 500 ng 1 310
30 1 L ,4-8 ph 1 (%) 8 26 (ng/l) (%) % ,4-XLD 10-1 (%) (ng/l) ,4-XLD 10-2 (ng/g-wet) (%)
31 10-3 (%) 7 14 (ng/g-wet) 2,4-XLD PS-2 1 μg/ml μl 10 ml PS-2 2 ml 1 ml 0.1 mol/l -10% 4 ml 1 ml 5 GC/MS 10 N- N--o- 70% 2 ml90% 1 ml 70% 3 ml 312
32 10 PS-2 Bond Elute PRS 1 μg/ml μl 0.01 mol/l 2 ml Bond Elute PRS 2 ml 1 ml 0.1 mol/l -10% 4 ml 1 ml 5 GC/MS mol/l KCl 1 mol/l KCl-20% 24XLD 5%
33 mol/l KCl-10%1 2 3 ml 30% 3 2 ml mol/l KCl 20% Bond Elute PRS mol/l KCl-10% 1 mol/l KCl-30% Bond Elute PRS 314
34 2, (ml) (ng) N-(N-EA) CV (ng/l) (%) (%) N--o-(N-Me-o-T) N--p-(N-Me-p-T) N--m-(N-Me-m-T) ,6-シ メチルアニリン (26XLD) o-(o-ea) ,4-シ メチルアニリン (24XLD) ,5-シ メチルアニリン (25XLD) p-(p-ea) m-(m-ea) ,5-シ メチルアニリン (35XLD) ,3-シ メチルアニリン (23XLD) ,4-シ メチルアニリン (34XLD)
35 N-(N-EA) 11-2 (g-dry) (ng) (ng/ g-dry) (%) o-(o-ea) ,4-シ メチルアニリン (24XLD) ,5-シ メチルアニリン (25XLD) CV (%) N--o-(N-Me-o-T) N--p-(N-Me-p-T) N--m-(N-Me-m-T) ,6- シ メチルアニリン (26XLD) p-(p-ea) m-(m-ea) ,5- シ メチルアニリン (35XLD) ,3- シ メチルアニリン (23XLD) ,4- シ メチルアニリン (34XLD)
36 12-1 (%) *1 (ng/l) *2 3 *2 7 *2 28 *2 N-(N-EA) N--o-(N-Me-o-T) N--p-(N-Me-p-T) N--m-(N-Me-m-T) ,6-シ メチルアニリン (26XLD) o-(o-ea) ,4-シ メチルアニリン (24XLD) ,5-シ メチルアニリン (25XLD) p-(p-ea) m-(m-ea) ,5-シ メチルアニリン (35XLD) ,3-シ メチルアニリン (23XLD) ,4-シ メチルアニリン (34XLD) *1 % * n=3 317
37 12-2 (%) *1 (ng/g-wet) *2 3 *2 7 *2 7 *2 N-(N-EA) N--o-(N-Me-o-T) N--p-(N-Me-p-T) N--m-(N-Me-m-T) ,6-シ メチルアニリン (26XLD) o-(o-ea) ,4-シ メチルアニリン (24XLD) ,5-シ メチルアニリン (25XLD) p-(p-ea) m-(m-ea) ,5-シ メチルアニリン (35XLD) ,3-シ メチルアニリン (23XLD) ,4-シ メチルアニリン (34XLD) *1 % * n=3n=1 n=1n=1 318
38 12-3 (%) *1 (ng/g-wet) *2 3 *2 7 *2 14 *2 N-(N-EA) N--o-(N-Me-o-T) N--p-(N-Me-p-T) N--m-(N-Me-m-T) ,6-シ メチルアニリン (26XLD) o-(o-ea) ,4-シ メチルアニリン (24XLD) ,5-シ メチルアニリン (25XLD) p-(p-ea) m-(m-ea) ,5-シ メチルアニリン (35XLD) ,3-シ メチルアニリン (23XLD) ,4-シ メチルアニリン (34XLD) *1 % * n=2n=1 n=2n=3 2,4- MDL MQL 14 ng/l 36 ng/l 7.3 ng/g-dry 19 ng/g-dry 2,4-1 ng/ml ng/ml (R=0.998) 10 μg/l ng/g-wet 2,4-12 MDL MQL 11 ng/l22 ng/l 28 ng/l56 ng/l 5.5 ng/g-dry7.8 ng/g-dry 14 ng/g-dry20 ng/g-dry 2, % % % 77102% 7 319
39 2,4-13 1) 2 6 2) N-N,N TEL FAX [email protected] 320
40 2,4-Dimethylaniline A simultaneous analysis method for the determination of 6 isomers of xylidine (XLD), 3 isomers of N-methyltoluidine,4 isomers of ethylaniline in water and sediment samples has been developed by gas chromatography/mass spectrometry with selected ion monitoring. A ml of water sample is passed through a preconditioned solid-phase extraction cartridge (PS-2) to collect previously described 13 isomers and then eluted with 3 ml of 0.01 mol/ml HCl - 70% methanol solution. The eluate is diluted with alkaline sodium chloride solution, and 13 isomers are extracted with 4 ml of hexane twice. Sediment samples are extracted by methanol / pure water (8:2) solution using sonication and centrifuge. Crude extract is diluted with pure water and solid-phase extracted in the same way as water samples. MDL, MQL of 2,4-dimethylaniline in water samples and sediment samples are 13 ng/l, 35 ng/l and 7.3 ng/g-dry, 19 ng/ g-dry, respectively. The recoveries of 2,4-dimethylaniline spiked to river water, seawater and river sediment were 92.3%-102%, 102% and 48.3%-75.5%, respectively. None of 13 isomers was detected in environmental samples. Water Sample Solid phase extraction ml wash:purifried water 20 ml Sep-Pak Plus PS-2 10 ml/min Dehydration over 30 sec Elution 0.01 mol/l HCl- 70%methanol 3 ml 0.5 mol/lnaoh-15%nacl 8 ml Shaking Extraction hexane 4 ml 5 min 2 times Phase partitioning more than 5 min Dehydration anhydrous Na2SO4 0.5 g syringe spike aniline-d 5 ng Make up volume hexane 10 ml GC/MS-SIM 321
41 Sediment sample Ultrasonic extraction 20 g-wet methanol/pure water (8:2) 20 ml 10 min 2 times Centrifugation 2500 rpm, 10 min Make up volume pure water ml Solid phase extraction rince the bottle: pure water 20 ml Sep-Pak Plus PS-2 10 ml/min Dehydration 30 min Clean up connect to cation exchange cartridge Bond Elute PRS Elution 0.01 mol/lhcl- 70%methanol 3 ml Wash 0.01 mol/lhcl-methanol discard 2 ml Sep-Pak Plus PS-2 Dehydration 30 min Elution 1 mol/lhcl-10%methanol 2 ml 2 times Liquid-liquid extraction 0.5 mol/lnaoh-15%nacl 8 ml hexane 4 ml 5 min Phase partitioning more than 5 min Dehydration anhydrous Na2SO4 0.5 g syringe spike aniline-d5 ng Make up volume hexane 10 ml GC/MS-SIM 322
42 2,4-2,4-Dimethylaniline 2,4-2,4-Xylidine ml 20 ml Sep-Pak Plus PS-2 10 ml/min 30 GC/MS-SIM ( ng/l) mol/l- 70% 3 ml 0.5 mol/l- 15% 8 ml (ng/g-dry) ml g GC 6890 (Agilent) MS 5973 (Agilent) -d5 ng 10 ml GC/MS-SIM SUPELCOWAX m 0.25 mm, 0.25 µm 323
43 2 20 g-wet /(8:2) 20 ml rpm10 ml 20 ml Sep-Pak Plus PS-2 10 ml/min 30 Bond Elute PRS 0.01 mol/l- 70% 3 ml Sep-Pak Plus PS mol/l- 2 ml mol/l- 10% 2 ml 0.5 mol/l- 15% 8 ml 4 ml g GC/MS-SIM -d5 ng 10 ml 324
平成26年度 化学物質分析法開発報告書
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平成26年度 化学物質分析法開発報告書
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