Analysis of Low Brominated DD/F Takeshi Nakano(Hyogo Pref. Inst. of Pub. Health and Env.Sci.)PCDD/DF/PCB in environment

,,,,PeCDF,,,,Co-PCB,,,TCDD,,,,,HxCN congeners congenerscongeners congeners

Trend of PCB Use in JapanTotal 58,000tAmount of PCB use (t)

PCB product use in JapanAr-1242 1248 1254 12601969-1971KC-300 400 500 600

KC300KC400KC500KC600JapanJapanHomologue patternreflects product use

Graph1

0

8.0308016321

26.7672437811

26.8077485563

22.4548453783

12.1968409665

2.9985865653

0.6297989168

0.0514895281

0.0014413042

Sheet1

1962196319641965196619671968196919701971

KC300KC400KC500KC600KC300KC400KC500KC600KC300KC400KC500KC600%KC300KC400KC500KC600

0000000010001001000100100010200.10300030

1001010204040030200501603010020050302001004301.121090500350

570480730850910710890720400590301,7401,0904001,050602,600420470500301,4209,160242,2301,2702,1401205,760

10010102050130208040014090260300380902107003709802.62005501400890

9060100160230340560790120650501,6101,0803808101802,45064040660701,4105,400142,5105402,1203005,470

1,3901,1601,7701,7002,5602,3202,6502,420620400903,5303,0104704501004,0301,620390440502,50020,080537,0501,4801,29024010,060

0009070140280508080021070501100230802010002001,0102.72001502900640

000010150200500050090009002000202900.8016000160

201010201010200000014010000240108000904301.115018000330

2,0901,7102,6302,8403,8303,7604,5904,0001,3901,7801707,3405,6401,7902,46034010,2302,9101,2701,7901506,12037,80012,5504,4506,03066023,690

KC300KC400KC500KC600

010000

60.025.714.30

38.722.037.22.1

22.561.815.70

45.99.938.85.5

70.114.712.82.4

31.323.445.30

010000

45.554.500

53.018.8253

Sheet1

Sheet2

Sheet3

0

0

0

0

0

0

0

0

0

0

0

0

0

0

0

0

()

%

PCB1969-1971

(t)

(1969-1971)

(t)

JapanHokkaidoTohokuKantoHokurikuTokaiKinkiChugokuShikokuKyusyu

D2CBs8.03080163211.23671482289.11303390696.01701449854.08351104596.919662701710.44666837154.96266241611.23671482287.3111572594

T3CBs26.767243781115.993511406530.83911308321.117657744820.019426338222.375062767433.530618987318.127786109815.993511406528.8398391406

T4CBs26.807748556347.588828633331.1654805225.199091247837.420030585921.676616672428.77958565124.375912625247.588828633339.3359573952

P5CBs22.454845378326.90772438419.012861957127.973982199426.372837922326.422234682316.375677518331.632689258526.90772438418.4014963762

H6CBs12.19684096655.77681562447.776407753515.60768959839.39065690617.17378725077.997129915117.27125075195.77681562444.3045587663

H7CBs2.99858656531.82265567541.63797506483.31329181362.09802288334.40210969162.26037288492.98354133071.82265567541.3235181246

O8CBs0.62979891680.58666708920.3494473020.66492593360.52185460220.9083879030.49148272140.550805080.58666708920.3818963792

N9CBs0.05148952810.07295376250.03723158050.05568429310.05858138630.06522542190.04128062410.05072437270.07295376250.0469271417

D10CB0.00144130420.00501763430.00148002270.00171999090.00330974970.00132643810.00104608710.0017779470.00501763430.0027368915

MCB0000000000

D2CBs8.01.29.16.04.16.910.45.01.27.3

T3CBs26.816.030.821.120.022.433.518.116.028.8

T4CBs26.847.631.225.237.421.728.824.447.639.3

P5CBs22.526.919.028.026.426.416.431.626.918.4

H6CBs12.25.87.815.69.417.28.017.35.84.3

H7CBs3.01.81.63.32.14.42.33.01.81.3

O8CBs0.60.60.30.70.50.90.50.60.60.4

N9CBs0.10.10.00.10.10.10.00.10.10.0

D10CB0.00.00.00.00.00.00.00.00.00.0

PCBHomologue DistributionandSource Estimation

Source estimationKCKCKCKCSediment ASediment BShip paintN.C.P.InsulatorInsulatorcapacitorcapacitor

To evaluate environmental risk

Daily variation of PCDD/Fsand PCBs in ambient air

Daily variation of Dioxin Concentration

Time trend of PCDD/F levels in ambient air

Time trend of PCDDs/PCDFsTEQMatsumura et al, symposium of J.Env.Chem, 2003.6Dioxin Emission Reduction Plan

0.000.100.200.300.400.50010002000300040005000600070008000Emission inventry (g-TEQ/yearPCDDs/PCDFspg-TEQ/m3)19971998199920002001Emission inventry vs Level in airMatsumura et al, symposium of J.Env.Chem, 2003.6

Matsumura et al, symposium of J.Env.Chem, 2003.6Time trend of Co-PCBsTEQ

Time trend of Co-PCBsTEQ

Time trend of PCB levels in ambient air

(log scale)

Ambient air

Low volume air sampler

Time trend of PCB levels in breast milk

Time trend of breast milk levels DioxinsPCBpg TEQ/g-fatg g-fat

60

40

20

0

Year (1973-2000)Konishi et al. (2003)Konishi et al (2003) Organohalogen compdspg TEQ/g-fatg / g-fatYear (1973-2000)

60

40

20

0

0.3

0.2

0.1

0

Development of congener specific analysis for PCBs using HT8-PCB

Congener number number of isomerof peakmono 3 3di 12 10tri 24 23tetra 42 39penta 46 38hexa 42 40hepta 24 23octa 12 12nona 3 3deca 1 1 total 209 192

Matsumura et al, J. Env. Chem. (2002)GC/MS-SIM chromatogram of TrCB (HT8-PCB)PCB product13C-TrCB

Matsumura et al, J. Env. Chem. (2002)GC/MS-SIM chromatogram of PeCB (HT8-PCB)13C-PeCBPCB product

Congener profiles of PCBsin environmental and human samples

Congener profiles of PCBs(Hexa-) in environmental and human samples

Congener profiles of PCBs(Hepta-) in environmental and human samples

Congener profiles of PCBsin human samples(pooled blood)

2831748099118153138163/164187180170Tri-CBsTetra-CBsPenta-CBsHexa-CBsHepta-CBsChromatogram of PCB in human blood 3~7ClHirai et al, (2003) Organohalogen compounds#187#180#153#138#74#99#118#28245-2345245-245245-234245-34245-2356245-4245-2424-4

Levels of the predominant PCB congeners in human bloodHirai et al, (2003) Organohalogen compounds245-23452345-234245-245245-234245-4245-24245-34245-2356245-2352345-34

22.334.142.449.054.559.663.467.070.373.375.6cumulative(%)

human milk/adipose tissue #74 (2,4,4',5-)#99 (2,2,4,4',5-)#118 (2,3,4,4',5-)#153(2,2',4,4',5,5'-)#138(2,2',3,4,4',5'-)#187(2,2',3,4,5,5,6-)PCB congeners predominant in human samples

Analysis of Low Brominated DD/F

ANALYSIS of MBDD/MBDF to T3BDD/T3BDF on a SP2331 - COLUMN

Introduction In the last two decades the increased use of brominated organic compounds especially brominated flame retardants (BFR) resulted in the presence of brominated compounds indoor, in the waste stream and in the environment.

IntroductionSome of the BFR, in particular the PeBDE, are associated with the presence and the formation potential of brominated dibenzo-p-dioxins and furans (PBDD/PBDF). Therefore the congener specific analysis of PBDD/PBDF received more attention in recent time.

IntroductionIn this respect also the analysis of low brominated DD/F homologues might be interesting in some processes and samples: Brominated aromatic compounds are subjected to debromination reaction under various conditions are dehalogenated more rapidly compared with chlorinated aromatic compounds.

IntroductionUnder UV or exposure to sunlight, brominated aromatic compounds can undergo rapid debromination . photo degradation

Debromination reactions are also observed during thermal degradation of polybrominated aromatics . thermal degradation

IntroductionTherefore it might be interesting to have selected samples analysed for low brominated DD/DF.

For this study we synthesised a low brominated DD and DF mixture and optimised a temperature program on a SP2331 column.

IntroductionWe have been reported complete assignment of M1CDD/F to T3CDD/F on SP-2331 (Dioxin 2000) DB5MS (Dioxin 2001) DB-Dioxin (Dioxin 2002)In this study, as the first step of complete assignment of M1BDD/F-T3BDD/F (74congeners)

Materials and MethodsStandards. (synthesised)The PBDD standards were synthesized by pyrolysis of bromophenols in Pyrex ampoules.The PBDD was synthesized by condensation of 2-monobromophenol, 2,4- and 2,6- dibromophenol(DBP) 2,4,6-tribromophenol (TBP) at 350C (30 min).

Standards PBDD by condensation2-BP + 2,4- DBP 2-M1BDD2-BP + 2,6- DBP 1-M1BDD2,4-DBP + 2,4- DBP 2,7/2,8-D2BDD2,4-DBP + 2,6- DBP 1,7/1,8-D2BDD2,6-DBP + 2,6- DBP 1,6/1,9-D2BDD2-BP + 2,4,6-TBP 1,3-D2BDD2,4- DBP + 2,4,6-TBP 1,3,7/1,3,8-T3BDD 2,6- DBP + 2,4,6-TBP 1,3,6/1,3,9-T3BDD 2,4,6- TBP + 2,4,6-TBP 1,3,6,8/1,3,7,9-T4BDD

Materials and MethodsStandards. (synthesised)For the PBDF mixture all three 2-/3-/4- bromophenol isomers, phenol, 2,4-DBP

were pyrolysed at 370C (15 minutes) in the presence of trace amounts of CuBr2

Standards PBDF4-BP + phenol 2-M1BDF3-BP + phenol 1-/3-M1BDF2-BP + phenol 4-M1BDF2,4-DBP + phenol 2,4-D2BDF4-BP + 4-BP 2,8-D2BDF3-BP + 3-BP 1,7-/3,7-/1,9-D2BDF2-BP + 2-BP 4,6-D2BDF------------------------------------------------------- 2,4-DBP + 4-BP 2,4,8-T3BDF-------------------------------------------------------2,4-DBP + 2,4-DBP 2,4,6,8-T4BDF

Materials and MethodsStandards. (commercially available )We obtained commercially available standards 2,7/2,8-D2BDD, 2,3,7-T3BDD 1,2,3,4-, 1,3,6,8-, 1,3,7,9-, 1,3,7,8-, 2,3,7,8-T4BDD 2,7-D2BDF, 2,8-D2BDF, 2,3,8-T3BDFEBC-2500 8-Br-2,3-CDF, 8-Br-2,3,4-CDF, 7-Br-2,3-CDD, 2-Br-3,7,8-CDD, EDF-2046: 13C-2,3,7,8-TeBrDF, 13C-2,3,7,8-TeBrDD (TeHxBrDD/DF)

GC/MS AnalysisThe analysis was carried out using HP 5890 II gas chromatograph connected to JMS-700 mass spectrometer (JEOL Ltd. Japan) operating at a resolution >10,000.

Temperature programTemperature program used for congener specific separation of the MBDD/F-T3BDD/F on SP2331 column (60m, 0.32mm i.d., 0.20um,): 120C, 1 min. isothermal; 20C/min. to 200C, 2C /min. to 260C, 30min. isothermal. Carrier gas flow rate: He 1.2mL/min.

Table.1Monitoring ionM1BrDD 261.9629263.9610D2BrDD 339.8735341.8715T3BrDD 419.7820421.7800T4BrDD 497.6925499.6904M1BrDF 245.9680247.9661D2BrDF 323.8785325.8765T3BrDF 403.7870405.7850T4BrDF 481.6975483.6955

Results and DiscussionThe use of the 2,4-DBP (resulting in 2- and 3- (7- and 8-) PBDD substitution) and 2,6-DBP (resulting in 1- and 4- (6- and 9-) PBDD substitution) produced a wide range of congeners within the D2BDD.

GC/MS-SIM chromatogram of M1BrDDT3BrDDSP2331 ; 60m x 0.32mmid. 0.20um; 120C (1 min.), 20C/min. to 200C, 2C /min. to 260C (30min).; He 1.2mL/min.

Reliable assignment (blue color) Confirmation by authentic standards

Progressing assignment red color Estimation from -formation ratio (major/minor) -regularity of elution order -comparison of RRT for PXDD/F (Cl and Br)

Brominated DD Mixture (Synthesis)

Major component

DiBrDD 13-, 27/28- , 16-/19-, 17/18-

TrBrDD 137-, 138-, 136-, 139-

TeBrDD 1368-, 1379-

2-MBP2,6-DBP2,4-DBP2,4,6-TBP1,3-DBDD2,8-DBDD2,7-DBDD1,3,6-D1,3,7-D1,3,8-D1,3,9-D

GC/MS-SIM chromatogram of M1BrDDT3BrDDSP2331 ; 60m x 0.32mmid. 0.20um; 120C (1 min.), 20C/min. to 200C, 2C /min. to 260C (30min).; He 1.2mL/min.

Results and Discussion

The use of all three monobromophenols produced a wide range of congeners within the D2BDF. Due to the higher pyrolysis temperature and the addition of CuBr2 the isomerisation/bromination reactions had a significant impact and hence a broad range of T3BDF were formed .

GC/MS-SIM chromatogram of M1BrDFT3BrDFSP2331 ; 60m x 0.32mmid. 0.20um; 120C (1 min.), 20C/min. to 200C, 2C /min. to 260C (30min).; He 1.2mL/min.

Reliable assignment (blue color) Confirmation by authentic standards

Progressing assignment red color Estimation from -formation ratio (major/minor) -regularity of elution order -comparison of RRT for PXDD/F (Cl and Br)

Brominated DF Mixture (Synthesis)

Major component M1BDF 2-, 1-, 3- , 4- (4:2:2:1) D2BDF 24-, 28- , 18-, 27-, 17-, 19-, 26-, 37- 16-, 26-, 46- T3BDF 248-, 247-, 246-, 249-(168-) T4BDF 2468-

2,8-DBDF2-MBDF1-MBDF3-MBDF4-MBDF2,4-DBDF2,4-DBP2-MBP3-MBP4-MBP

GC/MS-SIM chromatogram of M1BrDFT3BrDFSP2331 ; 60m x 0.32mmid. 0.20um; 120C (1 min.), 20C/min. to 200C, 2C /min. to 260C (30min).; He 1.2mL/min.

PCDFPBDFMCDFDCDFTCDFMBDFDBDFTBDF

On the high polar SP2331-column, all 4 M1BDF were separated and also for D2BDF and T3BDF a reasonable selectivity was achieved. However on the less polar DB5 column even the 4 brominated M1BDF were not completely separated while the 4 chlorinated M1CDF isomers could be separated also on this low polar column. This demonstrates that the selectivity for brominated congeners is smaller compared with the chlorinated congeners.

Separation of low chlorinated DD/F (Dioxin 2000, 2001, 2002) congener ULTRA-2 DB-5MS SP-2331 DB-DIOXINMCDF 4 4 4 4 4D2CDF16 8 10 15 16T3CDF28 8 10 23 21 congener ULTRA-2 DB-5MS SP-2331 DB-DIOXINMCDD 2 2 2 2 2D2CDD10 5 4 8 9T3CDD14 6 5 12 12

Separation of low brominated DD/F on BPX35 & SP-2331 congener BPX35 SP-2331MBDF 4 4 4D2BDF16 8 13T3BDF28 16 15 congener BPX35 SP-2331MBDD 2 2 2D2BDD10 5 7T3BDD14 6 9

Comparison of Separation for PXDD/F on SP-2331 (Cl/Br)congenerClBrMXDF 4 4 4D2XDF161513T3XDF282315congenerClBrMXDD 2 2 2D2XDD10 8 7T3XDD1412 9the selectivity for brominated congeners is smaller compared with the chlorinated congeners.

Comparison of Separation D2CDF and D2BDF 1,9-D2CDF 1,9-D2BDF

Low Brominated DD/F in Stack Gas Samples

GC/MS-SIM chromatogram(D2BrDF)SP2331 ; 60m x 0.32mmid. 0.20um; 120C (1 min.), 20C/min. to 200C, 2C /min. to 260C (30min).; He 1.2mL/min.PeCB(323.8834,325.8805)DiBrDF(323.8785, 325.8765)#126

GC/MS-SIM chromatogram(BrClDF)SP2331 ; 60m x 0.32mmid. 0.20um; 120C (1 min.), 20C/min. to 200C, 2C /min. to 260C (30min).; He 1.2mL/min.BrClDFBrCl2DF, BrClDDBrCl2DD

Thank you for your attention

Low Chlorinated DD/F in Environmental Samples

Ambient air

(MCDFTrCDF)Ambient airIncineration (flyash)Isomer distribution of ambient air(MCDF-TrCDF)

(MCDDTrCDD)Isomer distribution of ambient air(MCDD-TrCDD)Incineration (flyash)Ambient air

(MCDFTrCDF)28-23-27-37-2-238-128-237-1278-TCDF2378-TCDF238-TrCDF237-TrCDF128-TrCDF37-DiCDF27-DiCDF23-DiCDF28-DiCDFIsomer distribution of bleaching process(MCDF-TrCDF)

(MCDFTrCDF)(MCDFTrCDF)28-27-238-128-237-2-124-24-Isomer distribution of ambient air(MCDF-TrCDF)Isomer distribution of bleaching process(MCDF-TrCDF)Ambient air

CNP(MCDFTrCDF)(MCDFTrCDF)248-246-124-24-24-Isomer distribution of ambient air(MCDF-TrCDF)Isomer distribution of pesticide CNP (MCDF-TrCDF)pesticide CNPAmbient air

4-MCP3,4-DCP2,3,8-TrCDF1,2,8-TrCDF

Synthesis of 1,4,X-T3CDF isomers from chlorophenol Authentic standard (1,4,7- : NMR)2,5-DCP4-MCP3-MCP2-MCPO-m-p-1,4,6-TrCDF1,4,8-TrCDF1,4,9-TrCDF1,4,7-TrCDF

NMR 1,4,7-TrCDFAuthentic standardH9H6H8H2 ; H3

PCB levels andHomologue profiles in Environmental samples

PCB levels in air, water, sediment and biota (2002, MOE Japan)AirSedimentWaterBiota0.1-10ng/m30.1-10ng/L0.05-800ng/g-dry0.1-800ng/g-wet

Homologue profiles of PCBsin human samples

AirWaterBirdHuman bloodBreast milk

Congener profiles of TrCB,TeCBin human and combustion sample (A)

PCB congeners predominant in human samples (TrCB, TeCB)PCB productCombustionBreast milkCombustionPCB productBreast milk

Graph12

0.2521362922

0

3.8553943236

1.1804652803

1.1188671759

0.9913795665

3.090930818

2.2161453055

1.0284836765

0

0.0989663006

1.2892687915

0.3956011163

1.3119141826

7.5799999604

4.7246340261

3.4849474171

5.4313946986

3.7206443439

2.0699075764

4.3878581091

2.9854283841

0

0

0.0084507582

0.0740101554

KC400

KC

KC300KC400KC500KC600

_10.100.010.020.00

_20.000.000.000.00

_30.000.000.000.00

_100.120.000.000.00

_45.990.390.080.05

_90.280.020.010.00

_70.070.010.000.00

_61.040.090.020.01

_8_57.070.700.130.05

_140.000.000.000.00

_110.000.000.000.00

_13_120.000.000.000.00

_150.030.020.010.00

_191.750.250.030.02

_300.010.000.000.00

_1814.253.860.280.16

_175.501.180.110.09

_240.210.030.000.00

_270.880.170.020.01

_323.881.120.080.04

_164.490.990.100.06

_230.010.000.000.00

_340.020.010.000.00

_290.030.010.000.00

_260.730.290.030.02

_250.310.090.010.00

_313.903.090.190.06

_283.542.220.150.07

_210.020.010.000.00

_20_332.751.560.130.04

_221.931.030.070.03

_360.000.000.000.00

_390.000.000.000.00

_380.000.000.000.00

_350.000.000.000.00

_370.040.100.010.00

_540.040.020.000.00

_500.030.020.000.00

_531.061.290.070.03

_510.370.400.010.00

_451.181.310.040.03

_460.490.500.020.01

_52_694.417.584.280.42

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_650.000.000.000.00

_750.000.000.000.00

_48_472.913.480.120.05

_620.000.000.000.00

_443.455.431.120.09

_590.450.450.020.01

_421.411.720.060.02

_642.243.720.300.04

_720.000.000.000.00

_711.341.970.080.02

_410.810.810.020.02

_680.010.000.020.00

_400.760.900.050.01

_570.010.020.000.00

_670.070.120.010.00

_630.110.220.020.00

_580.000.000.000.00

_610.000.000.000.00

_740.682.070.250.02

_701.394.391.220.05

_760.040.060.010.00

_800.000.000.000.00

_661.072.990.260.02

_550.060.090.070.03

_600.561.150.070.00

_560.962.070.160.01

_790.000.000.000.00

_780.000.000.000.00

_810.000.010.010.00

_770.010.070.010.00

_1040.000.000.000.00

_960.040.200.040.00

_1030.010.040.030.00

_1000.000.030.010.00

_940.010.050.020.00

_102_930.110.280.120.00

_98_951.313.909.776.80

_880.010.030.000.00

_910.281.030.930.07

_1210.000.000.000.00

_920.290.461.560.51

_840.471.862.670.25

_890.060.210.030.00

_90_1011.373.469.816.20

_1130.010.020.000.01

_990.652.302.610.18

_112_1190.050.130.080.00

_830.080.220.320.02

_1080.000.000.000.00

_86_117_970.521.732.330.16

_125_1160.000.000.000.00

_87_1150.692.003.860.52

_1110.000.000.000.00

_850.341.190.810.07

_120_1101.164.059.001.76

_820.260.790.490.03

_1240.020.070.200.00

_109_1070.030.180.290.06

_1230.010.040.040.00

_1060.000.000.000.00

_1180.241.523.840.24

_1140.030.100.120.05

_1220.000.040.020.00

_105_1270.140.981.230.04

_1260.000.000.010.01

_1550.000.000.000.00

_1500.000.010.020.00

_1520.000.000.020.00

_1450.000.000.000.00

_1360.120.271.706.31

_1480.000.000.000.00

_1540.000.010.060.01

_1510.090.271.347.67

_1350.060.130.942.35

_1440.030.060.421.65

_1470.020.040.170.00

_149_1390.420.995.6920.32

_1400.000.000.030.00

_1430.000.010.030.00

_1340.030.080.550.61

_1420.000.000.000.00

_1310.010.040.160.08

_1330.000.010.100.09

_1650.000.000.000.00

_1460.050.150.811.40

_1320.250.513.305.09

_1610.000.000.000.00

_1530.400.865.5016.33

_1680.000.000.000.07

_1410.090.191.173.20

_1370.030.080.400.03

_1300.030.080.420.21

_164_1630.160.351.943.98

_1380.430.925.347.10

_1600.000.000.000.00

_1580.090.150.890.87

_1290.040.100.390.07

_1660.010.020.040.10

_1590.000.000.000.09

_1280.130.261.140.06

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Y-MWGeo-TOGeoPlsm-1PlsmVT-alklVT-trp-1VT-trp-2VTR

_1901666.2149.925.56.13.1661.4

_3006.400.50.70001.3

_183.9147.5626.2123.981.9204.476.975.4832.4

_172.5116.1246.445.935.774.828.426.9281.5

_241.711.6102.22.46.52.30.75.8

_271.41446.410.67.118.37.77.724.7

_323.149.6164.539.22659.326.631105.6

_162.247.6140.840.224.972.933.319.80

_231.513.63.91.51.40.80.70.40

_341.87.21.71.83.11.21.80

_292.916.69.42.71.85.93.81.90

_267.166.814928.919.665.656.380.51.8

_256.462.260.81311.424.122.633.30.7

_3114.6214.1495.5145.687159.4179.4269.65.6

_2815201.1381.9136.578.6107.8126.8203.94.3

_214.867.822.21.13.52.10.30

_20_3317.5168.2258.1114.463.9133.3163.7160.53

_2211.874.2118.359.433.455.384.495.11.9

_369.824.24.92.31.91.52.54.30

_390151.13.122.40.31.72.60

_3813.620.502.42.31.64.72.50

_3551.830.617.111.43.76.766.875.60

_3762.659.738.825.313.518.5168.1212.60.6

_548.52.50.60.6

_504.92.92.40.40.3

_534.4266.728.212.877.334.729.9

_51269.392.113.85.717.610.19.2

_453.4178.629.313.156.837.422

_461.474.314.15.627.817.214.3

_52_69222.61023.3168.961.3224.9209.2208.2

_73, _43_491.395.5676.4103.845123.5137.5135.9

_65, _751.1965.7508.91004581.1105.195.6

_441.714.2564.212346.6141.4222.3235.3

_590.85.575.541.711.232.581.7111.6

_421.19.418940.814.53768.874

_642.78306.172.231.961.3123.8134.1

_722.37.2230.346.227.1459390.9

_71, _4171.923.910.419.737.328.2

_682.7300.995.92.82.51.91.8

_401.32.569.421.68.223.556.944

_571.56.32.21.22.24.75.1

_672.21.832.55.557.12729.1

_632.5121.65.33.4515.117.8

_586.42.61.11.45.35.2

_615.47.9216.957.332.529.4156.1184.9

_74, _70918.2513.9124.266.788.2511.6475.2

_762.915.4293.8614.372.4

_808.930.8338.399.843.155.6291.4429.5

_668.9254.577.547.4276.8393.9

_554.11.29.13.82.71.718.221.9

_6014.14.962.733.716.519.9239.4233.9

_5612.78.5147.756.431.630.2290.9371.3

_7917.11.911.93.85.5

_7817.11.83.23.1

_8117.11.11.95.27.4

_7745.94.39.919.45.43.1132.5169.5

_2021.336.411.7

_20146.94.59.2

_2042.34.910.8

_1972.141.53.4

_2002.86.84.99

_198_1993.35.418.556.4

_19675.413.139.5

_2033.14.812.425.8

_1952.63.49.722.9

_1949.44.239.4143.4

_2057.76.75.97.3

_208137.996.30.61.98.5

_207178.394.52.50.78.8

_206234.278.32.11255.7

_209693.24224.53.418.6

ng/g-lipidStructurering-1ring-2

#190.0465517241

#300.0581896552

#180.3336206897

#170.2017241379

#16, #320.3413793103

#260.124137931

#280.19784482762,4',4-424

#311.0241379312,4',5-425

#220.1396551724

#350.0465517241

#370.0892241379

TrCB2.7

#530.0533216235

#510.0263471551

#450.1417727872

#73, #520.4755034189

#43, #490.3130292955

#47, #48, #750.6291951571

#440.3600777868

#59, #420.1486732325

#41, #64, #680.3745059908

#400.0677498275

#630.0784141522

#743.85734897432,4,4',5-4245

#70, #760.2659808042

#80, #661.9553352989

#56, #600.7508939213

#790.3883068816

#810.0815507183

#770.0319929741

TeCB10

#102, #98, #93, #95, #121, #880.3553240741

#920.3333333333

#84, #101, #90, #891.1851851852

#996.11805555562,2',4,4',5-24245

#97, #86, #125, #111, #87, #117, #116, #1150.5555555556

#120, #850.3310185185

#1100.400462963

#124, #107, #1090.6631944444

#1189.64351851852,3',4,4',5-34245

#114, #1220.5474537037

#105, #1271.7662037037

#1260.1006944444

PeCB22

#1510.6407624633

#135, #1440.2668621701

#1470.1730205279

#139, #149, #1400.4780058651

#143, #134, #133, #1310.5747800587

#142, #165, #146, #1614.1158357771

#15329.88563049852,2',4,4',5,5'-245245

#141, #1370.6818181818

#1300.6099706745

#13817.71700879772,2',3,4,4',5'-234245

#166, #1590.9882697947

#1620.3431085044

#128, #1671.4105571848

#1562.5527859238

#1570.5469208211

#1690.0146627566

HxCB61

#1790.2823889405

#186, #1781.7649308781

#1879.34167531832,2',3,4',5,5',6-2356245

#1832.3982296049

#1850.116277799

#174, #1810.564777881

#1771.7919239386

#1710.5938473307

#173, #192, #1721.0174307415

#18013.66887055352,2',3,4,4',5,5'-2345245

#193, #1910.905305721

#1705.11207037872,2',3,3',4,4',5-2345234

#1890.4422709142

HpCB38

#2020.5056674338

#2010.1099539701

#2040

#1970.0277905639

#2000.0181242808

#1980.0652474108

#1991.27232451092,2',3,3',4,5,5',6'-23452356

#196, #2031.11403912542,2',3,3',4,4',5',6-23452346

#1950.2543440736

#1940.8004890679

#2050.0320195627

OcCB4.2

#2080.0846428571

#2070.0664285714

#2060.14892857142,2',3,3',4,4',5,5',6-234562345

NoCB0.3

#2090.1

198219851986198719881992199319941995199619971998199920002001

18_1735.273358455751.011673274736.32386741611.78306860330.383363545610.54088424136.20637004498.978390570511.196043053811.70384529317.91126995365.92006824252.640150813750.8819286853.9234657556

31_2887.698293275273.070568976776.749610326134.662151285661.687985970335.994336741318.241597536627.47620441235.643555342424.079688918933.571665578133.084999451414.250569333474.341222528117.627689696

5286.6059563124106.631378212679.042468353339.295105974364.199947856528.527087543118.911456697525.8844012129.980653073520.839554109735.748812805845.545800818315.685781920546.704001903416.0429980157

4966.8471193417113.747279483770.275254047728.779785231341.199585977427.260529586212.738072745530.184519541423.314379318219.78828391739.852616505649.49769352112.006271632642.669988518515.8951139955

47_4852.528423856972.551450583947.01210473717.911244999625.496651508118.69792086849.188658039222.627067167616.750693060413.006998040126.577262587534.1037572978.401747193224.057261630710.6208657281

4448.317501921958.446640841642.746940912719.178999204929.787377777115.78396548889.454540300712.778910614213.233093100511.282428096515.443239310917.86683144357.897861773912.65771591446.9301351442

41_6453.902291282760.233278697242.548737468728.627204373428.959815267315.16271680869.35907117112.842230195317.707936364411.8882047817.551934504520.5286214969.27706890818.45980074639.2415971244

7457.490795530668.35435165548.163585900232.75274739334.161865771618.26454894610.873765481718.617492743519.062944764112.439443912827.109237566934.139818892711.305454770319.74828334211.8258659427

7080.00173148264.671966188260.288265855637.425737031649.099041615422.612547690613.460349534420.393060304824.444382318215.938427999930.033504341131.82206853713.70850767419.362699354612.2650423654

6696.896025867141.161492956775.289677868540.601354787950.642069971335.760300165917.406275076927.704407478730.45531620923.418524307452.292581357662.021394837818.073654563632.184562355122.2702794618

60_5644.188205328347.975592204129.868509976520.215825601624.961372385412.61940670367.56420415019.30003685814.66783598528.684687836116.890397651215.8128607528.173948727814.3107559297.8825999447

9581.1898141643105.416437080471.392545568543.447111499851.729393779230.546109667419.561010865525.825375645120.286935196919.599420489536.806880000541.474866789520.554548692719.517532004417.280885061

90_101158.5101892379239.4757139963168.936032509694.6942505853118.138004280364.451891858946.046881262573.845656510463.968042938751.1230589042105.2869514801106.311717448251.016100889851.280069036349.3601186706

9997.6871890622184.7764077691120.225627937966.693364708577.935043971850.427388597930.178966377373.098054124650.028428136342.035249889694.0612855968106.176457137936.588350338340.673857560444.2406531739

9728.426838054843.343222350627.66148933617.301897982822.149438956911.11015327757.879975442310.6192946199.08360774238.064689283715.211551665115.66891645647.6027333597.79257887487.8523007874

8753.55437161967.135303493150.444505514335.326787725543.488624665820.051677205515.306598619418.668350864116.935940786614.012887484624.73655086824.74021463215.57897658716.117454938613.6167867167

8525.234269542639.867788840125.99016021116.691429256720.05257039710.15505757887.218201528211.40730344119.84121179697.895368506215.175747397215.39272821227.979035238.92411174028.3431983388

110106.3890892576135.301229829899.477341839368.153960590576.148992499939.368711927328.795941634334.586507783234.536719046328.134718651353.217683360550.849133949728.995187250429.662882152128.2018316805

118149.71933967228.9042427392156.8716975056110.9127587537127.066344586366.319073150443.068000720174.952573927962.514837726651.867762121101.4179133087100.695715704851.266285538256.736570086256.1907559555

10548.109111362569.068851916446.438008350834.198799567639.089068034919.408631641313.162237308719.593703878618.306720377614.318375536125.526779649626.356969907614.739111277817.222205828717.4413326774

15144.48740113390.397303693649.89901618829.574425204834.786485639621.049295787611.194596679828.681865798724.861595419415.349022631336.864198559844.887749985716.952961391516.608156444216.2346073064

149132.8993018479231.4071114183152.792864479499.768421718699.886499104266.237490313938.955179440880.997398958270.518415506248.2966762988101.9686745416128.065844495554.875723423749.91685134454.7337602443

14635.943780605681.132292266147.017173474428.086286536929.796137127821.950327524712.049091268534.937692675427.145638357718.984262639444.437294392459.311591619919.811747739520.92661947221.1241681162

153263.1700790084444.1623450553313.9694477118198.8309019479215.2377332667140.686964895384.9465180345212.799208736177.8355067539122.9660483324269.5898704047351.3480654674130.3053099953135.4678934606137.037746695

132_16826.142809955833.747836406526.340515453819.064787756619.026658191310.43402678466.26127328269.97045911898.99118902837.071960053213.461284282213.4508917847.00375140567.73502652076.8490880404

138237.4564946731390.6038045655267.0538552447191.1866791885200.2973416697112.355544895575.1115394889141.2980829655129.018534504295.3137203376183.9231888756199.6430864461103.5034745505109.8129594232102.7357746498

128_16733.608421682350.727021868337.724887347428.990126100529.608847272616.044270821210.399301120918.903229984716.179099790212.673374799925.082951418725.01830512313.396664321515.580109965913.6362075097

18765.4859658407167.509759815681.231826205749.718777555949.932107356137.941818367219.230192512365.050928151661.376961897836.980138693977.3679607062129.68515751443.202470043937.550451998139.8901958292

18081.0148274028142.067468339182.460726440257.328350951663.32770360634.649590381521.956551049349.634300623764.639524095132.744813979272.637032075886.562650522144.6499961934.898617249733.3877266178

170_19034.623398584562.416678019138.178385981326.095250553628.713854726915.78952728699.819079517921.586745513427.027701759314.35517949630.951178640437.03879362520.032698664316.353064486315.0644067832

cement

UTSDCl

_1680250111201

_2930180009.115001

_339015005.93701

_10_430150.416.32

_9_7351300.51342

_627700.28272

_8_5481500.56172

_14172300.17252

_11442000.61282

_12_13426100.44562

_152.1210.0533.22

_19181.30.0592.13

_300.930.0140.333

_1857120.34133

_17256.90.114.53

_276.23.30.0231.23

_241.74.60.0180.693

_16_32369.40.168.83

_342.55.80.011.43

_232.5290.0161.53

_292.4280.0161.83

_2658.70.0394.53

_253120.0222.93

_3116120.12143

_28136.70.139.13

_33_20_2111580.12103

_224.690.0473.53

_361.5190.0111.43

_3907.70.0091.63

_381.2620.0123.23

_353.2610.0382.73

_371.1150.0291.43

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_533.60.910.0195.64

_511.50.440.011.94

_453.50.960.01554

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_430.490.720.0030.954

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_47_48_755.93.90.055154

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_422.11.40.0165.84

_71_720.320.5600.624

_41_682.42.60.0219.14

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_580.0442050476100.124

_630.171.10.0020.754

_610.233.10.00724

_74120.0163.24

_760.45612050671.10.00914

_701.73.90.038.74

_66_801.54.60.038104

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_89_1130.030.160.0060.385

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_86_1250.0350.2200.195

_111_1170.010.2500.135

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_87_1150.380.870.00883.85

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_1230.0110.1500.0925

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_1500.0080.036006

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_145_1480.0060.06600.0136

_136_1540.20.2600.726

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_1440.030.06400.196

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_1400.0040.02200.0126

_134_133_1430.0280.07300.146

_131_1650.0090.04900.0366

_146_161_1420.0450.210.0030.326

_153_1680.20.550.0161.76

_1320.10.190.0050.426

_1410.0370.100.36

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_1300.0110.0450.0010.0696

_164_1630.0510.190.0040.326

_1380.180.470.01416

_158_1600.0140.130.0020.0966

_1290.010.03500.0366

_16600.0200.0356

_15900.022006

_16200.042006

_128_1670.0220.110.0030.0996

_1560.0020.080.0020.0246

_15700.0300.0076

_16900.008006

_18800.007007

_18400.016007

_1790.0560.09700.437

_1760.0170.03600.147

_178_1860.0120.04500.137

_17500.01300.0277

_187_1820.0510.140.0040.587

_1830.0230.0760.00090.297

_1850.0040.01300.0457

_174_1810.0320.0650.0020.317

_17700.03400.147

_1710.0080.0290.00120.0737

_1730000.0047

_172_19200.01600.0377

_180_1930.0370.110.0070.417

_19100.01300.0097

_1700.0130.050.0040.127

_19000007

_18900.007007

_20200.00800.0358

_20100.0100.028

_20400008

_19700.00700.018

_20000.00700.0168

_19800008

_1990.0080.01700.0688

_196_2030.0080.02100.0818

_19500008

_19400.0080.0010.0288

_20500.005008

_20800.00700.0079

_20700.00800.0059

_2060.0040.01400.0149

_2090.0090.02300.01310

10-12

IUPAC10-198210-198510-198610-198710-198810-199210-199310-199410-199510-199610-199710-199810-199910-200010-200111-198211-198511-198611-198711-198811-199211-199311-199411-199511-199611-199711-199811-199911-200011-200112-198212-198512-198612-198712-198812-199212-199312-199412-199512-199612-199712-199812-199912-200012-200110-12_198210-12_198510-12_198610-12_198710-12_198810-12_199210-12_199310-12_199410-12_199510-12_199610-12_199710-12_199810-12_199910-12_200010-12_2001

190.631.931.130.390.860.150.000.100.220.320.000.000.002.950.190.000.000.000.070.000.000.000.000.000.000.000.000.000.000.000.070.040.030.000.030.000.020.000.000.000.000.000.000.000.000.711.961.170.460.890.150.020.100.220.320.000.000.002.950.19

18_1732.7849.6533.1511.2428.699.764.918.458.1210.847.355.511.7250.493.652.151.302.880.541.460.781.300.533.080.860.360.410.410.390.160.340.060.290.000.240.000.000.000.000.000.200.000.520.000.1135.2751.0136.3211.7830.3810.546.218.9811.2011.707.915.922.6450.883.92

24_271.833.252.390.731.740.650.270.540.630.710.310.210.002.970.160.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.020.030.000.000.000.000.000.000.000.000.030.000.060.000.001.853.282.390.731.740.650.270.540.630.710.340.210.062.970.16

16_3212.4820.3213.256.069.283.811.163.353.253.731.380.000.0013.620.130.980.611.450.210.720.420.470.361.740.420.140.150.210.160.170.000.000.000.000.000.000.000.000.000.000.000.000.000.000.0013.4620.9314.706.2710.004.221.633.715.004.151.520.150.2113.780.30

269.6510.439.263.088.823.301.572.622.493.023.083.660.8421.142.030.400.190.610.100.300.180.140.161.040.220.000.120.000.000.110.060.000.080.000.030.000.000.000.000.000.090.000.190.050.1110.1110.619.953.189.143.481.712.783.533.243.173.781.0321.192.24

254.645.673.761.303.761.510.690.980.911.141.701.530.6211.211.020.260.000.360.000.100.100.060.100.520.000.000.000.000.000.100.080.000.090.000.070.080.000.080.060.000.080.120.000.000.004.995.674.211.303.931.680.751.161.491.141.781.650.6211.211.12

31_2879.5968.4168.1032.3255.0431.9215.8224.2420.9321.5124.2330.508.9371.7814.437.754.667.942.346.654.072.433.2414.712.577.641.773.301.802.020.360.000.710.000.000.000.000.000.000.001.700.812.020.761.1887.7073.0776.7534.6661.6935.9918.2427.4835.6424.0833.5733.0814.2574.3417.63

3313.6014.8212.265.059.664.682.822.923.933.833.271.211.385.022.311.890.652.500.271.620.750.600.874.300.760.270.250.280.350.270.150.000.260.000.030.000.000.000.000.000.580.000.690.180.4415.6315.4715.025.3211.325.433.413.798.234.594.121.472.365.543.02

229.658.596.165.037.093.382.411.862.932.542.131.680.355.341.320.860.371.260.170.920.440.280.392.390.480.130.220.000.150.140.000.000.030.000.000.000.000.000.000.000.540.120.840.300.4210.518.967.445.208.013.822.692.255.323.012.802.021.195.781.88

372.943.482.042.352.150.650.230.450.220.240.490.380.000.640.001.010.321.070.150.720.500.230.402.890.470.760.220.350.180.110.090.040.250.070.030.000.000.000.000.000.180.000.340.210.264.043.843.362.572.911.150.460.843.110.711.430.600.691.040.37

540.000.150.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.150.000.000.000.000.000.000.000.000.000.000.000.000.00

501.281.491.190.190.680.690.240.820.000.240.160.090.000.140.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.001.281.491.190.190.680.690.240.820.000.240.160.090.000.140.00

534.318.345.312.273.331.980.862.051.391.431.712.000.823.061.170.000.000.190.080.070.000.080.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.004.318.345.502.353.401.980.942.051.391.431.712.000.823.061.17

512.946.353.842.041.651.330.472.171.051.211.401.720.792.221.320.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.030.000.000.000.000.000.000.000.000.000.000.000.000.000.002.976.353.842.041.651.330.472.171.051.211.401.720.792.221.32

453.935.073.561.732.621.060.650.890.730.820.860.970.521.070.510.170.000.140.000.000.000.000.000.000.000.000.000.000.000.000.040.000.000.000.000.000.030.000.000.000.000.000.000.000.004.145.073.701.732.621.060.680.890.730.820.860.970.521.070.51

69_460.101.030.180.320.310.090.030.120.150.150.000.150.140.210.140.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.101.030.180.320.310.090.030.120.150.150.000.150.140.210.14

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4964.65112.9868.7327.7240.3326.8712.3129.7320.9819.1239.5148.7711.7442.2915.622.040.731.451.010.790.350.360.422.250.670.320.730.240.380.280.160.030.090.040.070.050.070.040.090.000.030.000.030.000.0066.85113.7570.2828.7841.2027.2612.7430.1823.3119.7939.8549.5012.0142.6715.90

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15611.8217.9113.4811.0110.925.883.497.036.444.869.939.815.115.445.252.413.102.281.551.770.720.810.530.890.470.820.370.751.110.840.680.570.420.430.430.220.140.160.140.070.140.060.080.130.0414.9121.5816.1813.0013.126.824.447.727.475.4010.8910.245.946.686.13

1572.464.143.012.342.281.400.751.751.611.182.502.811.371.311.180.540.490.470.380.350.140.230.000.250.100.170.120.290.290.150.080.070.050.060.070.030.000.000.000.000.000.000.000.000.003.084.703.532.792.701.570.981.751.861.292.672.931.661.591.33

1690.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.00

1880.120.610.270.110.150.170.040.290.200.160.380.850.150.170.190.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.120.610.270.110.150.170.040.290.200.160.380.850.150.170.19

1840.691.031.000.630.680.700.250.660.610.712.501.631.765.942.180.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.691.031.000.630.680.700.250.660.610.712.501.631.765.942.18

17914.2029.3316.7710.3911.418.193.1512.6410.107.0514.3320.767.045.937.220.000.491.370.670.100.080.000.190.190.000.250.240.190.000.070.000.000.000.000.000.000.000.000.000.000.000.000.000.000.0014.2029.8218.1411.0611.518.273.1512.8310.297.0514.5821.007.235.937.29

1763.706.663.782.562.751.770.742.442.151.453.013.911.591.241.510.000.170.400.140.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.003.706.834.182.702.751.770.742.442.151.453.013.911.591.241.51

1788.7925.5011.017.077.555.772.679.489.035.7711.6218.226.155.365.501.331.681.660.920.950.280.600.530.710.150.370.300.660.640.570.050.030.030.030.030.000.000.000.000.000.000.000.000.000.0010.1627.2112.708.028.526.053.2710.019.745.9211.9918.526.816.006.07

1750.982.401.200.921.000.520.260.750.990.551.301.630.690.520.490.200.320.280.090.100.000.000.000.070.000.000.050.000.090.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.001.182.721.481.011.100.520.260.751.060.551.301.680.690.620.49

18756.36157.0970.8043.1944.5236.3215.8361.8156.4635.8074.49127.1738.8833.0735.938.9910.3510.366.465.331.593.383.244.881.182.882.514.324.463.960.130.070.070.060.080.040.020.000.040.000.000.000.000.020.0065.49167.5181.2349.7249.9337.9419.2365.0561.3836.9877.37129.6943.2037.5539.89

18318.8636.4219.2813.9314.698.824.6612.2315.198.9119.6124.4810.898.008.683.774.523.892.142.560.701.261.322.180.631.020.551.331.341.170.720.410.440.410.460.190.120.130.130.060.120.060.070.090.0523.3541.3523.6116.4817.719.716.0413.6817.509.6020.7525.0912.309.439.90

1851.883.411.661.191.280.710.290.881.070.601.471.810.780.610.540.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.000.001.883.411.661.191.280.710.290.881.070.601.471.810.780.610.54

17418.8731.3518.5212.3013.768.334.269.9911.839.2914.3117.888.526.426.820.952.642.301.150.660.250.650.721.140.170.630.280.450.550.270.040.000.030.000.000.000.000.000.000.000.000.000.000.000.0019.8533.9920.8413.4514.428.584.9110.7112.989.4514.9418.168.976.967.09

17716.8542.1020.6413.9613.2610.464.9115.1713.128.6918.8223.1710.278.509.662.373.713.501.721.670.501.011.351.820.350.900.601.061.000.980.090.050.060.040.050.000.000.000.000.000.000.000.000.000.0019.3145.8524.2115.7214.9810.965.9316.5214.949.0419.7223.7711.339.5010.64

1717.0113.377.575.225.503.501.714.765.523.227.749.624.023.083.321.161.731.330.620.950.230.340.620.640.230.380.210.420.440.360.260.140.150.1