Homogeneous Catalysis A Personal View Matthias Beller

Homogeneous CatalysisA Personal View 1. Introduction

What does these processes have in common ?Life Relies on Chemical Reactions

Catalysis - Important for our SocietyValue of products made via catalysis > 2.5 x 106 Mio US$.

The Catalyst Group: The Intelligence Report: Global Shifts in the Catalyst Industry19972003Worldwide Merchant Catalyst Markets* toll manufacturing fees onlyBillion US$ 7.4 9.0PolymerRefineryChemicalEnvironmental1.6*1.72.12.0RefineryPolymerEnvironmental2.1*2.32.22.3Chemical

Catalysis - Research for the 21th Century

First Institute for Catalysis Research in Europe; founded 1952.2003: ca. 90 Employees (18 permanent scientists, >20 postdocs, 13 Ph.D. students). Background and main expertise is homogeneous catalysis, based on transition metal complexesTransfer of excellent basic research to industrial applications

Branch office in WarnemndeCatalysis research at the IfOK

Main building, Rostock-City

Biphase/multiple phaseActivity (of metal content)selectivityConditions of reactionLife-time of catalystSensitivity of deactivationProblems due to diffusionRecycling of catalystSteric and electronic propertiesMechanismMono phasehighvariablehighvariablemildharshvariablelonglowhighnoneusually difficulteasily changedrealistic models do existdifficult to solvecan easily be doneno variation possiblenot obviousHomogenous versus Heterogenous Catalysis

Homogenous CatalysisA Personal View 2. Biphasic Catalysis andHydroformylation

Example: Shell Higher Olefin Process (SHOP, 1968)KKABABKBA12Work-up(Distillation)C4-20--nOlefins

Cat. + Solv. OligomerisationCat.Ni(COD)2+2P-CH2CO2HSolv. 1,4-butanediolW. Keim et al. DE-P2054009 (1969) SHELLW. Keim, Chem. Ing.Techn. 56 (1984) 850C2H4C2H4Isomerisation(Mo/ Al2O3)Metathesis(Re/ Al2O3)C4-10C12-18C20+C10-14Two-Phase Catalysis

OHC8OC8CuCrO3Rh I / TPPMS + CO / H2Ni

+ H2HOOH1,9-Nonanediol++ H2OC4C4 Pd II / TPPMS Sulfolane/H2OHydrodimerizationIsomerizationHydroformylationHydrogenationN. Yoshimura et al., US-Pat. 4 808 756 (1989)4The Kuraray Nonanediol Process

R. Jackstell, M. Gomez, A. Frisch, H. Klein, A. Zapf, O. Briel, R. Karch, D. Rttger, M. Beller, Angew. Chem. Int. Ed. 2002, 41, 986-989. Telomerization: New CatalystsCatalyst performance:S/C = 1.000.000 : 1TON > 900.000TOF > 80.000 h-1

Reaction discovered 1938 by Otto Roelen Catalyst metals: first Cobalt, later RhodiumIn case of aliphatic olefins: linear aldehydes are preferred productsOne of the most important homogeneous catalytic reactions (> 7 Mio. to/a)Most important product: butyraldehyde (> 4 Mio to/a)Hydroformylation: General Aspects

actual catalyst: HRh(PR3)3CO studied first by Wilkinson et al. in 1968 most important processes for propene hydroformylation: UCC: PPh3 / Rh: 400 : 1, T: 85 - 90 C, p: 15 - 18 bar, n / i: 90 %Ruhrchemie/Rhone Poulenc: TPPTS / Rh = >100 : 1, T = 120 C, p < 20 barIn general two classes of ligands:Phosphines (P-C-bond)Phosphites (P-O-bond)Rh-catalyzed Hydroformylation

Gas phaseGas phaseGas phaseHydrocarbonHydrocarbonHydrocarbonphasephasephase Aqueous phaseFluorous phaseHRh(CO)[PPh3]3HRh(CO)[P(C6H4SO3Na)3]3HRh(CO)(P[CH2)2(CF2)5CF3]3)3Hydroformylation - The Multiphase Approach

Selectivitiestowards C4 products (%)towards C4 aldehydes (%)Products other thann-butanal (%)n-/ i-ratioManufacturing costsCapital expenditure costsWaste water volume

Energy consumption figuresSteamPowerSyngas compression

Reaction conditionsPressure (bar)Temperature (C)E factorCo high pressureprocessRCH/RPprocess9386

3180:20140>1.970

82>21.7

3001500.6-0.9>9999

Why internal olefins?Interesting feedstock:Butenes (raffinat-II)Hydroformylation of Internal OlefinsAmount of aldehydes produced by hydroformylation

Raising the Barr for the Perfect ReactionA. Seayad, M. Ahmed, H. Klein, R. Jackstell, T. Gross, M. Beller, Science, 2002, 297, 1676-1678.

steamcrackerlow severitycatcracker (FCC)gasoil, zeolitesteamcrackerhigh severityalkynes2432207726213221465472alkynes1212371315110,5Composition of C4-Fractions

1

fast isomerisation necessary no hydroformylation of internal double bonds fast and selective reaction of the terminal olefinHydroformylation of internal olefinsThe selective formation of linear aldehydes starting from internal alkenes is still one of the greater challenges in hydroformylation chemistry.P. W. N. M. van Leeuwen et al., In Rhodium Catalyzed Hydroformylation, P. W. N. M. van Leeuwen, C. Claver, Eds., Kluwer, Dordrecht, 2000, p.57.

used for the hydroformylation of 2-butene different steric bulk at the P-atoms seems advantageous van Leeuwen: steric bulk in the ortho position of the bridge is necessaryLigands for Rh-catalyzed hydroformylation 1995 published by van Leeuwen et al. broad variation of the Bite angel 1999 hydroformylierung of internal olefins: 2-Octene: n / i: 90 : 10, TOF: 112 h-1 (bridged aryl-substituents), (2 bar, 120 C)

Conditions: t: 16 h, Rh / olefin: 0,01 mol %, P / Rh: 10 1977 published by Tamao et al.; later on patented by Eastman Kodak and Hoechst. very good n/i-selectivity at low pressure, however activity is too low.increase of activity possible by substituted Phenyl groups?Hydroformylation with NAPHOS

Pentene

p

(bar)

T

(C)

Yield

(%)

n / i

1

10

120

76

99 : 1

1

10

140

60

91 : 9

1

50

120

88

97 : 3

1

50

140

85

97 : 3

2

10

120

20

91 : 9

2

10

140

56

90 : 10

2

50

120

3

49 : 51

2

50

140

25

58 : 42

Yield (A...D): 44 %New synthetis of substituted NAPHOS-ligands

Conditions: 2-Pentene, t: 16 h, Rh / olefin: 0,01 mol %, p: 10 bar, T: 120 Cunusual increase of activityInfluence of the Ligand ConcentrationIPHOSTOF (20% conversion) = > 800 h-1H. Klein, R. Jackstell, D. Rttger, K.-D. Wiese, M. Beller, Angew. Chem. Int. Ed. 2001, 40, 3408.

L / Rh

Yield (%)

n / i

0

10

40 : 60

1,25

20

85 : 15

2,5

48

90 : 10

5

68

90 : 10

10

80

90 : 10

20

88

91 : 9

Homogenous CatalysisA Personal View 3. Challenges

Phenol from benzene and oxygen

Direct synthesis of aromatic aminesfrom ammonia

Selective oxidation of methaneto methanol

Oxidative coupling from methanol to ethylene

Anti-Markovnikov addition of alcohols and amines to olefinsLow-temperature oxidation of SO2 to SO3

High-conversion and selectiveproduction of olefins from alkanes

Facile decomposition of NOX

Low-temperature epoxidation of ethylene

Direct H2O2-synthesisfrom H2 and O2

Chem. Eng. News 1993, May 31, 23.Ten Challenges for Industrial Catalysis

R+ HXRXHRHX"When a hydrocarbon of unsymmetrical structure combines with a halogen hydracid the halogen adds itself to the less hydrogenated carbon atom, i.e. to the carbon which is more under the influence of other carbon atoms."(V. Markovnikov, Comptes rendus 1875, 82, 668.) Detours for anti-Markovnikov products:radical reactionshydroborationindirect paths (hydroformylation, telomerisation)Markovnikov productanti-MarkovnikovproductThe Markovnikov Rule

First hydroamino-methylation: W. Reppe, DBP 839800, 1943; W. Reppe, Experientia, 1949, 5, 93. available starting materials (olefins, ammonia, CO, hydrogen)industrially important productsanti-Markovnikov addition preferredProblemsselectivity for prim. amines and linear products (n/iso)catalyst recoverycatalyst activityHydroaminomethylation of olefins

Use of two-phase catalysisincrease of selectivity via extraction of prim. aminessimple catalyst recyclinguse of water solutions of ammonia Rh:Ir:B. Zimmermann, J. Herwig, M. Beller, Angew. Chem. Int. Ed. Engl. 1999, 38, 2372.A New Concept for Hydroaminomethylations

Yield of amine: 80 - 90 %

T=130C, p(start)=78bar (pentene/butene) or 60bar (propen/ethen), CO:H2=1:5, t=10h 0.026 mol-% Rh, 0.21 mol-% Ir, TPPTS: P/Rh=425, P/Ir=52, BINAS: P/Rh=140, P/Ir=18.NH2+ CO + 2 H2 + NH3+NH2Variation of Olefins and Ligands

TPPTS

BINAS

Olefin

NH3:

Olefin

n/i

prim.:

sec.

n/i

prim.:

sec.

Ethen

8

-

25:75

-

-

Propen

8

76:24

72:28

99:1

77:23

1-Buten

8

85:15

78:22

99:1

78:22

1-Penten

8

84:16

90:10

99:1

87:13

Ethen

0,5

-

3:97

-

-

Propen

0,5

82:18

20:80

99:1

1:99

1-Buten

0,5

87:13

38:62

99:1

1:99

1-Penten

0,5

82:18

48:52

99:1

10:90

Linear Amines from Internal OlefinsA. Seayad, M. Ahmed, H. Klein, R. Jackstell, T. Gross, M. BellerScience 2002, 297, 1676-1678.

Entry

Olefin

Amine

Conv. (%)

Total amine Selec. (%)

Linear amine Selec.

l:b

1

100

97

88

90:10

2

88

98

82

82:18

3

71

69

53

72:28

4

78

90

83

91:9

5

100

65

74

78:22

6

80

87

62

71:29

7

77

91

76

78:2

8

60

96

90

94:6

_1086767239.cdx

_1086767529.cdx

_1086767611.cdx

_1086767647.cdx

_1086767696.cdx

_1086767538.cdx

_1086767320.cdx

_1086767500.cdx

_1086767297.cdx

_1086767086.cdx

_1086767128.cdx

_1086766712.cdx

RR4-5 % fast isomerisation necessary no hydroformylation of internal double bonds fast and selective reaction of the terminal olefinHydroaminomethylation of internal olefins

Homogenous CatalysisA Personal View 4. Fine Chemicals

Produce a minimum of waste; use available feedstocksEfficiencyApply energy-efficient processes with 100% atom economy; use domino processes and mcrsSelectivityHighly selective (chemo-, regio-, stereoselective) processes (100% yield)EconomicsPerform reactions in standard equipment; minimize catalyst costs (real catalytic processes); look for high space/time yieldsEnvironmentThe Ideal Chemical Synthesis

E = kg waste productkg desired productoil refiningbulk chemicalsfine chemicalspharmaceuticals106 - 108104 - 106102 - 104101 - 1030.1

IbuprofenBoots process(CH3OC)2O / AlCl3ClCH2CO2C2H5 / NaOC2H5H+ / H2OH2NOHH+ / H2OClassic Process for Ibuprofen

IbuprofenBoots process(CH3OC)2O / AlCl3ClCH2CO2C2H5 / NaOC2H5H+ / H2OH2NOHH+ / H2OHoechst process(CH3OC)2O / HFH2 / Kat.CO / PdNew Process for Ibuprofen

Improved Synthesis of Pharmaceuticals52-67%90-99%M. Beller, C. Breindl, Tetrahedron, 1998, 54, 6359.

1,0 mol% Pd 240,- Euro 0,1 mol% Pd 24,- Euro 0,005 mol% Pd 1,2 EuroRaw material costs for 1 kg benzoic acid:Ph-OTf 660,- Euro Ph-I 30,- EuroPh-Br 2,0 EuroPh-Cl 0,57 EuroAryl-X ActivationClR

ProsulfuronNaproxenM. Beller, A. Zapf, Top. Cat. 2001 in press. First commercial Heck reaction developed by Ciba-Geigy in mid 80s (> 100 to/a). New process by AlbermarleHeck reactions

2PdXArLLPdLPdXLLArRPdLLXHPdXArLR+ 2 LRed.+ L+ L- L- LArXLLArRBHB Xsp2-C-X bond dissociationenergies at 298 K:C-F527 kJ/molC-Cl402 kJ/molC-Br339 kJ/molC-I272 kJ/molrequirements for active catalysts:- coordinatively unsaturated Pd species- highly nucleophilicuse of bulky and electron rich ligandsMechanism for Heck Reactions

3-5%2%J. F. Cairns, H. L. Roberts, J. Chem. Soc. C 1968, 640-642.KnowledgeUnderstanding is getting familiar with facts and thoughts.

203040ppm203040ppmPdL2PdL239.5 ppm39.5 ppm22.5 ppm22.0 ppm5 min25 min45 min75 min125 min5 min25 min45 min65 min30 C+50 COxidative Addition of Aryl Chlorides to Pd(PCy3)2

OTBNLosartanLosartan process by MSD Hoechst (Clariant) process for ATII-antagonists Suzuki reactions

ClB(OH)2+RR0.005 mol% Pd(OAc)20.01 mol% BuPAd2toluene, K3PO4100 C, 20 ha) 4 hA. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315.BuPAd2 - Variation of SubstratesBuPAd2

Entry

R

Yield [%]

TON

1

4-Me

87

17,400

2a)

4-Me

74

14,800

3

2-Me

85

17,000

4

2,6-Me2

68

13,600

5

H

80

16,000

1234IMesIPrIPrIPrEt2O / THFEt2O / THFToluene / THFTHF4545808020202051.5 mol% Pd2(dba)3Entry L Solvent Temp. [C] Time [h] Yield [%] 567noneIMesIPrDioxane / THFDioxane / THFDioxane / THF80808033335971086041994 mol % LHClLit.: Huang, J.; Nolan, S. P. J. Am. Chem. Soc. 1999, 121, 9889-9890.L = IPrCross Coupling of Grignard Reagents

Wakamatsu reaction(Co-catalyzed)CO / H2(50 - 100 bar)

HCo(CO)4(1 - 5 mol%)N-Acyl Amino AcidOne-pot Synthesis of N-Acyl Amino Acids with 100 % Atom Utilization

High Selectivity and Chemical YieldTolerance of various functional groupsAmidocarbonylation ReactionsM. Beller, M. Eckert, Angew. Chem. 2000, 112, 1027; Angew. Chem. Int. Ed. 2000, 39, 1010.

Mechanism

N-Acetyl-cysteineSarcosinatesAspartameCaptoprileMethotrexateVancomycineRNCH3COOHONCOOHOSHNCOOHSHOHHOOCNCORHO2HNNNOOOOOROOHHHH2NCO2HNCO2CH3COHN-Acylamino Acids: Fine Chemicals and Pharmaceuticals

Strecker reaction:Amidocarbonylation (Wakamatsu reaction):Advantages:no salt productioninexpensive ubiquitous feedstockshigh yields and selectivitiesRCHOHCN, NH3RHCNNH2CH2O, H+RCHCOOHNH 2R"ClO- HClHNR"CHRCOOOHRCHOH2NR"O+CO, H2Cat.HN"OCHRCOOHRH. Wakamatsu.et al., J. Chem. Comm. 1971, 1540.Comparison of Syntheses of N-Acylamino Acids

Amidocarbonylation Reactions

Homogeneous CatalysisA Personal View 6. Oxidation Chemistry

Capacity10 6 to/y0.51.01.71018HydrocyanationOligomerisationHydrogenationOxidationHydroformylationand other CO reactionse.g. Terephthalic Acidand -Anhydrideca. 5 mio to/yelemental O2 (some O3)H2O2tBu-OOHNaOClCrO3, K2SO5, K2S2O8 ...Homogenous Catalysis and Industrial Impact

M = Os, Ru, Mn1912 Hofmannfirst catalytic process (with ClO3)1936-42Criegeerate enhancement with pyridine1936MilasH2O2 as secondary oxidant1956 Upjohn-processNMO as secondary oxidant1980 Sharplessstoichiometric AD1987Sharplesscatalytic AD1990 TsujiK3[Fe(CN)6] as secondary oxidant-Dihydroxylation of Olefins

Proposed Catalytic Cycle

K2[OsO2(OH)4]The Sharpless AD: Ready for Application?

thermo-statvacuumpumpstirrerc = 5*10-4 mol/lin buffer pH 10.4T = 25COxidation of Os(VI)0220230240250260270280290300310320330340350360370380390400Wellenlnge [nm]UV / VISspectrophotometerOs(VI)0,20,40,60,811,21,41,61,82AbsorptionO2airN2Ooptrode

air O2c = 5*10-4 mol/lin buffer pH 10.4T = 25CAbsorption/Time Curves for the Reoxidation of Os(VI) (at 232 nm)

GMTD000

gm 0...Zeit [min]Zeit rel. [min]Abs. (232)Abs. rel.

50-82.331.6207

66-76.331.61390.9930285011

712-70.331.61630.9954890301

818-64.331.61690.9961041624

924-58.331.6261.0054336682

1030-52.331.62471.0041008817

1136-46.331.62311.002460529

1242-40.331.62591.0053311462

1348-34.331.62311.002460529

1454-28.331.62471.0041008817

1560-22.331.62391.0032807054

1666-16.331.62681.0062538446

1772-10.331.62831.0077916752

1878-4.331.63121.0107648144

19841.671.62691.0063563666

20907.671.6311.0105597704

219613.671.63161.0111749026

2510219.671.63381.0134303875

2610825.671.59840.9771375846

2711431.671.55720.9348985032

2812037.671.50680.8832273939

2912643.671.45070.8257125282

3013249.671.39630.7699405372

3113855.671.34310.7153988107

3214461.671.28880.6597293418

3315067.671.24450.6143120771

3415673.671.19470.5632561001

3516279.671.16710.5349600164

3616885.671.13080.4977445151

3717491.671.09410.4601189256

3818097.671.06560.4309001435

39186103.671.03680.4013737954

40192109.671.00820.3720524913

41198115.670.98610.34939512

42204121.670.97030.3331966373

43210127.670.94760.3099241337

44216133.670.92890.2907525118

45222139.670.91260.2740414189

46228145.670.89550.2565101497

47234151.670.88030.2409267993

48240157.670.86690.2271888456

49246163.670.85680.2168341193

50252169.670.84130.2009432028

51258175.670.83150.1908960426

52264181.670.8210.1801312282

53270187.670.81080.1696739799

54276193.670.80270.1613696945

55282199.670.79320.1516301005

56288205.670.7870.1452737339

57294211.670.77990.1379946689

58300217.670.77430.1322534345

59306223.670.76550.1232314948

60312229.670.75970.1172852163

61318235.670.75610.1135944228

62324241.670.74780.1050850933

63330247.670.74730.1045724831

64336253.670.74160.0987287267

65342259.670.73670.0937051466

66348265.670.7350.0919622719

67354271.670.72970.0865286036

68360277.670.72570.082427722

69366283.670.72530.0820176338

70372289.670.72090.0775066639

75402319.670.70860.0648964527

80432349.670.69950.0555669469

85462379.670.68980.0456223088

90492409.670.68450.0401886406

95522439.670.67890.0344474062

100552469.670.6740.0294238261

110612529.670.6680.0232725036

120672589.670.65950.01455813

130732649.670.65880.0138404757

140792709.670.65540.0103547263

150852769.670.65130.0061513225

160912829.670.6480.0027680951

170972889.670.64710.0018453968

1801032949.670.64530

&A

Seite &P

GMTD001

Zeit [min]Zeit rel. [min]Abs.Abs. rel

010.650

0.511.150.00061.00

111.650.00031.00

1.512.150.00061.00

212.65-0.0011.00

2.513.150.00031.00

313.650.00081.00

3.514.150.0011.00

414.650.00031.00

4.515.1501.00

515.650.00071.00

5.516.1501.00

616.650.00071.00

6.517.150.00031.00

717.650.00081.00

7.518.150.00131.00

818.650.00091.00

8.519.150.09881.13

919.650.01591.02

9.520.150.00491.01

1020.6501.00

10.521.15-0.0021.00

1121.65-0.0060.99

11.522.15-0.0080.99

1222.65-0.0080.99

12.523.15-0.010.99

1323.65-0.0110.99

13.524.15-0.0150.98

1424.65-0.0190.97

14.525.15-0.0230.97

1525.65-0.0270.96

15.526.15-0.030.96

1626.65-0.0320.96

16.527.15-0.0350.95

1727.65-0.040.95

17.528.15-0.0460.94

1828.65-0.0490.94

18.529.15-0.0530.93

1929.65-0.0580.92

19.530.15-0.0610.92

2030.65-0.0660.91

20.531.15-0.0690.91

2131.65-0.0740.90

21.532.15-0.0790.90

2232.65-0.0830.89

22.533.15-0.090.88

2333.65-0.0920.88

23.534.15-0.0980.87

2434.65-0.1010.87

24.535.15-0.1080.86

2535.65-0.1130.85

25.536.15-0.1170.84

2636.65-0.1210.84

26.537.15-0.1260.83

2737.65-0.130.83

27.538.15-0.1360.82

2838.65-0.1420.81

28.539.15-0.1460.81

2939.65-0.1510.80

29.540.15-0.1560.79

3040.65-0.1610.79

30.541.15-0.1640.78

3141.65-0.1710.77

31.542.15-0.1760.77

3242.65-0.180.76

32.543.15-0.1850.75

3343.65-0.1890.75

33.544.15-0.1930.74

3444.65-0.1970.74

34.545.15-0.2020.73

3545.65-0.2070.73

35.546.15-0.2110.72

3646.65-0.2150.71

36.547.15-0.2190.71

3747.65-0.2240.70

37.548.15-0.2280.70

3848.65-0.2320.69

38.549.15-0.2350.69

3949.65-0.240.68

39.550.15-0.2450.68

4050.65-0.2480.67

40.551.15-0.2520.67

4151.65-0.2560.66

41.552.15-0.2590.66

4252.65-0.2650.65

42.553.15-0.2670.65

4353.65-0.2710.64

43.554.15-0.2760.63

4454.65-0.2790.63

44.555.15-0.2830.62

4555.65-0.2860.62

45.556.15-0.290.62

4656.65-0.2920.61

46.557.15-0.2980.60

4757.65-0.30.60

47.558.15-0.3040.60

4858.65-0.3060.59

48.559.15-0.310.59

4959.65-0.3130.58

49.560.15-0.3160.58

5060.65-0.3190.58

50.561.15-0.3220.57

5161.65-0.3260.57

51.562.15-0.3290.56

5262.65-0.3320.56

52.563.15-0.3350.56

5363.65-0.3380.55

53.564.15-0.3410.55

5464.65-0.3440.54

54.565.15-0.3460.54

5565.65-0.350.54

55.566.15-0.3530.53

5666.65-0.3550.53

56.567.15-0.3570.53

5767.65-0.3610.52

57.568.15-0.3650.52

5868.65-0.3670.51

58.569.15-0.3680.51

5969.65-0.3730.51

59.570.15-0.3740.50

6070.65-0.3760.50

60.571.15-0.3790.50

6171.65-0.3810.49

61.572.15-0.3840.49

6272.65-0.3860.49

62.573.15-0.3880.49

6373.65-0.3910.48

63.574.15-0.3940.48

6474.65-0.3950.48

64.575.15-0.3970.47

6575.65-0.4010.47

65.576.15-0.4030.47

6676.65-0.4050.46

66.577.15-0.4070.46

6777.65-0.4090.46

67.578.15-0.4110.45

6878.65-0.4140.45

68.579.15-0.4160.45

6979.65-0.4170.45

69.580.15-0.420.44

7080.65-0.4220.44

70.581.15-0.4240.44

7181.65-0.4270.43

71.582.15-0.4280.43

7282.65-0.4290.43

72.583.15-0.4320.43

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932942.65-0.7480.01

932.5943.15-0.7480.01

933943.65-0.7480.01

933.5944.15-0.7480.01

934944.65-0.7470.01

934.5945.15-0.7480.01

935945.65-0.7470.01

935.5946.15-0.7470.01

936946.65-0.7470.01

936.5947.15-0.7470.01

937947.65-0.7470.01

937.5948.15-0.7470.01

938948.65-0.7480.01

938.5949.15-0.7470.01

939949.65-0.7490.01

939.5950.15-0.7470.01

940950.65-0.7480.01

940.5951.15-0.7470.01

941951.65-0.7480.01

941.5952.15-0.7470.01

942952.65-0.7480.01

942.5953.15-0.7470.01

943953.65-0.7490.01

943.5954.15-0.7490.01

944954.65-0.7480.01

944.5955.15-0.7480.01

945955.65-0.7480.01

945.5956.15-0.7480.01

946956.65-0.7470.01

946.5957.15-0.7480.01

947957.65-0.7480.01

947.5958.15-0.7480.01

948958.65-0.7490.01

948.5959.15-0.7490.01

949959.65-0.7480.01

949.5960.15-0.7480.01

950960.65-0.7480.01

950.5961.15-0.7490.01

951961.65-0.7490.01

951.5962.15-0.7490.01

952962.65-0.7490.01

952.5963.15-0.7480.01

953963.65-0.7480.01

953.5964.15-0.7490.01

954964.65-0.7490.01

954.5965.15-0.750.01

955965.65-0.7490.01

955.5966.15-0.7490.01

956966.65-0.750.01

956.5967.15-0.7480.01

957967.65-0.7480.01

957.5968.15-0.7490.01

958968.65-0.7480.01

958.5969.15-0.7490.01

959969.65-0.7490.01

959.5970.15-0.7490.01

960970.65-0.7480.01

960.5971.15-0.7490.01

961971.65-0.7490.01

961.5972.15-0.7490.01

962972.65-0.7490.01

962.5973.15-0.7490.01

963973.65-0.7490.01

963.5974.15-0.7490.01

964974.65-0.7490.01

964.5975.15-0.7490.01

965975.65-0.7490.01

965.5976.15-0.7490.01

966976.65-0.750.01

966.5977.15-0.7490.01

967977.65-0.7490.01

967.5978.15-0.7490.01

968978.65-0.7490.01

968.5979.15-0.750.01

969979.65-0.750.01

969.5980.15-0.750.01

970980.65-0.7490.01

970.5981.15-0.7490.01

971981.65-0.750.01

971.5982.15-0.750.01

972982.65-0.750.01

972.5983.15-0.750.01

973983.65-0.750.01

973.5984.15-0.7490.01

974984.65-0.7490.01

974.5985.15-0.7490.01

975985.65-0.7490.01

975.5986.15-0.7490.01

976986.65-0.750.01

976.5987.15-0.7490.01

977987.65-0.750.01

977.5988.15-0.750.01

978988.65-0.750.01

978.5989.15-0.7490.01

979989.65-0.750.01

979.5990.15-0.7510.00

980990.65-0.750.01

980.5991.15-0.750.01

981991.65-0.750.01

981.5992.15-0.750.01

982992.65-0.7510.00

982.5993.15-0.7510.00

983993.65-0.7510.00

983.5994.15-0.750.01

984994.65-0.750.01

984.5995.15-0.750.01

985995.65-0.750.01

985.5996.15-0.750.01

986996.65-0.7510.00

986.5997.15-0.750.01

987997.65-0.7510.00

987.5998.15-0.750.01

988998.65-0.7510.00

988.5999.15-0.7510.00

989999.65-0.750.01

989.51000.15-0.7510.00

9901000.65-0.7510.00

990.51001.15-0.750.01

9911001.65-0.750.01

991.51002.15-0.750.01

9921002.65-0.750.01

992.51003.15-0.750.01

9931003.65-0.7510.00

993.51004.15-0.7520.00

9941004.65-0.750.01

994.51005.15-0.7510.00

9951005.65-0.7510.00

995.51006.15-0.7510.00

9961006.65-0.7510.00

996.51007.15-0.7520.00

9971007.65-0.750.01

997.51008.15-0.750.01

9981008.65-0.7510.00

998.51009.15-0.750.01

9991009.65-0.7510.00

999.51010.15-0.750.01

10001010.65-0.7520.00

1000.51011.15-0.7510.00

10011011.65-0.7510.00

1001.51012.15-0.7510.00

10021012.65-0.7520.00

1002.51013.15-0.7520.00

10031013.65-0.7510.00

1003.51014.15-0.7510.00

10041014.65-0.7510.00

1004.51015.15-0.7510.00

10051015.65-0.7520.00

1005.51016.15-0.7510.00

10061016.65-0.7510.00

1006.51017.15-0.7510.00

10071017.65-0.7520.00

1007.51018.15-0.7520.00

10081018.65-0.7510.00

1008.51019.15-0.7520.00

10091019.65-0.7530.00

1009.51020.15-0.7520.00

10101020.65-0.7520.00

1010.51021.15-0.7520.00

10111021.65-0.7510.00

1011.51022.15-0.7520.00

10121022.65-0.7520.00

1012.51023.15-0.7520.00

10131023.65-0.7510.00

1013.51024.15-0.7510.00

10141024.65-0.7520.00

1014.51025.15-0.7510.00

10151025.65-0.7510.00

1015.51026.15-0.7510.00

10161026.65-0.7520.00

1016.51027.15-0.7520.00

10171027.65-0.7520.00

1017.51028.15-0.7520.00

10181028.65-0.7510.00

1018.51029.15-0.7520.00

10191029.65-0.7520.00

1019.51030.15-0.7520.00

10201030.65-0.7520.00

1020.51031.15-0.7520.00

10211031.65-0.7520.00

1021.51032.15-0.7520.00

10221032.65-0.7520.00

1022.51033.15-0.7520.00

10231033.65-0.7520.00

1023.51034.15-0.7520.00

10241034.65-0.7520.00

1024.51035.15-0.7520.00

10251035.65-0.7520.00

1025.51036.15-0.7520.00

10261036.65-0.7530.00

1026.51037.15-0.7520.00

10271037.65-0.7530.00

1027.51038.15-0.7530.00

10281038.65-0.7520.00

1028.51039.15-0.7520.00

10291039.65-0.7530.00

1029.51040.15-0.7530.00

10301040.65-0.7530.00

1030.51041.15-0.7530.00

10311041.65-0.7530.00

1031.51042.15-0.7520.00

10321042.65-0.7510.00

1032.51043.15-0.7520.00

10331043.65-0.7520.00

1033.51044.15-0.7530.00

10341044.65-0.7530.00

1034.51045.15-0.7520.00

10351045.65-0.7530.00

1035.51046.15-0.7520.00

10361046.65-0.7530.00

1036.51047.15-0.7530.00

10371047.65-0.7530.00

1037.51048.15-0.7530.00

10381048.65-0.7530.00

1038.51049.15-0.7520.00

10391049.65-0.7520.00

1039.51050.15-0.7520.00

10401050.65-0.7530.00

1040.51051.15-0.7530.00

10411051.65-0.7520.00

1041.51052.15-0.7530.00

10421052.65-0.7530.00

1042.51053.15-0.7530.00

10431053.65-0.7530.00

1043.51054.15-0.7530.00

10441054.65-0.7530.00

1044.51055.15-0.7530.00

10451055.65-0.7540.00

1045.51056.15-0.7520.00

10461056.65-0.7540.00

1046.51057.15-0.7530.00

10471057.65-0.7530.00

1047.51058.15-0.7540.00

10481058.65-0.7540.00

1048.51059.15-0.7530.00

10491059.65-0.7530.00

1049.51060.15-0.7530.00

10501060.65-0.7540.00

&A

Seite &P

GMTD002

Zeit [min]Zeit rel. [min]Abs.Abs. rel.

0-10.171.4651

0.5-9.671.46571.0006824386

1-9.171.46380.9985213831

1.5-8.671.46420.9989763421

2-8.171.46310.9977252047

2.5-7.671.46551.0004549591

3-7.171.46410.9988626024

3.5-6.671.46671.0018198362

4-6.171.46490.9997725205

4.5-5.671.46681.001933576

5-5.171.46440.9992038217

5.5-4.671.46611.0011373976

6-4.171.46651.0015923567

6.5-3.671.46490.9997725205

7-3.171.46030.9945404914

7.5-2.671.46721.002388535

8-2.171.46360.9982939035

8.5-1.671.46511

9-1.171.4661.0010236579

9.5-0.671.46611.0011373976

10-0.171.46621.0012511374

10.50.331.46651.0015923567

110.831.46721.002388535

11.51.331.46621.0012511374

121.831.4671.0021610555

12.52.331.46871.0040946315

132.831.46771.0029572338

13.53.331.4681.0032984531

143.831.46561.0005686988

14.54.331.46581.0007961783

154.831.46681.001933576

15.55.331.46931.0047770701

165.831.46531.0002274795

16.56.331.46611.0011373976

176.831.46450.9993175614

17.57.331.471.0055732484

187.831.46851.003867152

18.58.331.47011.0056869882

198.831.46661.0017060965

19.59.331.46511

209.831.46851.003867152

20.510.331.46480.9996587807

2110.831.46841.0037534122

21.511.331.46841.0037534122

2211.831.46621.0012511374

22.512.331.46531.0002274795

2312.831.46931.0047770701

23.513.331.46891.004322111

2413.831.46611.0011373976

24.514.331.46891.004322111

2514.831.46781.0030709736

25.515.331.46731.0025022748

2615.831.46831.0036396724

26.516.331.46891.004322111

2716.831.4671.0021610555

27.517.331.46831.0036396724

2817.831.47111.0068243858

28.518.331.46851.003867152

2918.831.46941.0048908098

29.519.331.62191.178343949

3019.831.46440.9992038217

30.520.331.47741

3120.831.45990.9940855323

31.521.331.4941

3221.831.48231

32.522.331.45680.9905595996

3322.831.45540.9889672429

33.523.331.44760.9800955414

3423.831.44380.9757734304

34.524.331.4380.9691765241

3524.831.43220.9625796178

35.525.331.42610.9556414923

3625.830.945

36.526.331.41020.9375568699

3726.831.40090.9269790719

37.527.330.91

3827.831.38280.9063921747

38.528.331.37370.8960418562

3928.831.3620.8827343039

39.529.331.3540.8736351228

4029.831.34250.86055505

40.530.331.33260.8492948135

4130.831.32530.8409918107

41.531.331.31140.8251819836

4231.830.81

42.532.331.29330.8045950864

4332.831.28420.794244768

43.533.331.27250.7809372157

4433.831.2630.7701319381

44.534.331.2560.7621701547

4534.830.75

45.535.330.74

4635.830.73

46.536.330.72

4736.831.20940.7091674249

47.537.331.19970.6981346679

4837.831.19130.6885805278

48.538.330.68

4938.830.67

49.539.331.16950.6637852593

5039.831.16040.6534349409

50.540.331.15230.64422202

5140.831.14540.6363739763

51.541.331.13760.6275022748

5241.831.13120.6202229299

52.542.331.12330.6112374886

5342.831.11550.6023657871

53.543.331.10940.5954276615

5443.831.10360.5888307552

54.544.331.09670.5809827116

5544.831.09020.5735896269

55.545.331.08320.5656278435

5645.831.07650.5580072793

56.546.331.07280.5537989081

5746.831.06720.5474294813

57.547.331.060.5392402184

5847.831.05460.5330982712

58.548.331.04650.5238853503

5948.831.04290.5197907188

59.549.331.03640.5123976342

6049.831.03260.5080755232

60.550.331.02680.5014786169

6150.831.02170.495677889

61.551.331.01890.4924931756

6251.831.01550.4886260237

62.552.33

6352.831.00460.4762283894

63.553.330.99910.4699727025

6453.830.99940.4703139217

64.554.330.99110.4608735214

6554.830.98690.4560964513

65.555.330.98110.449499545

6655.830.97650.4442675159

66.556.330.97340.4407415833

6756.830.96920.4359645132

67.557.330.96440.4305050045

6857.830.960.425500455

68.558.330.9580.4232256597

6958.830.95470.4194722475

69.559.330.94930.4133303003

7059.83

70.560.330.94120.4041173794

7160.830.93580.3979754322

71.561.330.93330.3951319381

7261.830.93070.3921747043

72.562.330.92720.3881938126

7362.830.92330.3837579618

73.563.330.91990.3798908098

7463.830.91440.3736351228

74.564.330.91380.3729526843

7564.830.91020.3688580528

75.565.330.90770.3660145587

7665.830.90480.3627161056

76.566.330.90070.3580527753

7766.830.8980.3549818016

77.567.330.89370.3500909918

7867.830.89190.3480436761

78.568.330.88960.3454276615

7968.830.88670.3421292084

79.569.330.88250.3373521383

8069.830.87770.3318926297

80.570.330.87720.3313239308

8170.830.87590.3298453139

81.571.330.87150.3248407643

8271.830.86860.3215423112

82.572.330.86530.317788899

8372.830.86490.3173339399

83.573.330.86060.3124431301

8473.830.85830.3098271156

84.574.330.85630.3075523203

8574.830.85490.3059599636

85.575.330.85290.3036851683

8675.830.85110.3016378526

86.576.330.84610.2959508644

8776.830.84470.2943585077

87.577.330.84140.2906050955

8877.830.84010.2891264786

88.578.330.83630.2848043676

8978.830.83530.28366697

89.579.330.83240.2803685168

9079.830.83170.2795723385

90.580.330.82950.2770700637

9180.830.82840.2758189263

91.581.330.82420.2710418562

9281.830.82340.2701319381

92.582.330.81990.2661510464

9382.830.81920.2653548681

93.583.330.81610.2618289354

9483.830.81520.2608052775

94.584.330.81270.2579617834

9584.830.81050.2554595086

95.585.330.810.2548908098

9685.830.8080.2526160146

96.586.330.80550.2497725205

9786.830.80350.2474977252

97.587.330.80610.2504549591

9887.830.80180.2455641492

98.588.330.79980.243289354

9988.830.79740.2405595996

99.589.330.79530.2381710646

10089.830.79320.2357825296

100.590.330.79230.2347588717

10190.830.79080.2330527753

101.591.330.78860.2305505005

10291.830.78770.2295268426

102.592.330.78640.2280482257

10392.830.7840.2253184713

103.593.330.78110.2220200182

10493.830.78080.2216787989

104.594.330.78070.2215650591

10594.830.77820.2187215651

105.595.330.77620.2164467698

10695.830.77390.2138307552

106.596.330.77370.2136032757

10796.830.77290.2126933576

107.597.330.77030.2097361237

10897.830.76820.2073475887

108.598.330.76860.2078025478

10998.830.76510.2038216561

109.599.330.76470.203366697

11099.830.76350.2020018198

110.5100.330.76280.2012056415

111100.830.76280.2012056415

111.5101.330.7610.1991583258

112101.830.75880.196656051

112.5102.330.75670.1942675159

113102.830.75560.1930163785

113.5103.330.75420.1914240218

114103.830.75550.1929026388

114.5104.330.7530.1900591447

115104.830.74960.1861919927

115.5105.330.75070.1874431301

116105.830.74910.1856232939

116.5106.330.7480.1843721565

117106.830.74640.1825523203

117.5107.330.74410.1799363057

118107.830.7450.1809599636

118.5108.330.74290.1785714286

119108.830.74090.1762966333

119.5109.330.74190.1774340309

120109.830.74110.1765241128

120.5110.330.74010.1753867152

121110.830.73640.1711783439

121.5111.330.73590.1706096451

122111.830.73570.1703821656

122.5112.330.73520.1698134668

123112.830.73260.1668562329

123.5113.330.73320.1675386715

124113.830.73150.1656050955

124.5114.330.73150.1656050955

125114.830.7290.1627616015

125.5115.330.72730.1608280255

126115.830.72820.1618516833

126.5116.330.72740.1609417652

127116.830.72450.1576433121

127.5117.330.7240.1570746133

128117.830.72350.1565059145

128.5118.330.72260.1554822566

129118.830.72190.1546860783

129.5119.330.72090.1535486806

130119.830.71940.1518425842

130.5120.330.71930.1517288444

131120.830.71740.1495677889

131.5121.330.71720.1493403094

132121.830.71590.1478616924

132.5122.330.7160.1479754322

133122.830.71470.1464968153

133.5123.330.71410.1458143767

134123.830.71150.1428571429

134.5124.330.71280.1443357598

135124.830.71060.141833485

135.5125.330.70970.1408098271

136125.830.70930.1403548681

136.5126.330.70880.1397861692

137126.830.70850.13944495

137.5127.330.70750.1383075523

138127.830.70570.1362602366

138.5128.330.70680.137511374

139128.830.70630.1369426752

139.5129.330.70350.1337579618

140129.830.70340.133644222

140.5130.330.70150.1314831665

141130.830.70170.131710646

141.5131.330.70030.1301182894

142131.830.70.1297770701

142.5132.330.69890.1285259327

143132.830.69780.1272747953

143.5133.330.69820.1277297543

144133.830.69680.1261373976

144.5134.330.69670.1260236579

145134.830.69490.1239763421

145.5135.330.69450.1235213831

146135.830.69370.122611465

146.5136.330.69520.1243175614

147136.830.69420.1231801638

147.5137.330.69540.1245450409

148137.830.69090.1194267516

148.5138.330.6910.1195404914

149138.830.69040.1188580528

149.5139.330.6910.1195404914

150139.830.6890.1172656961

150.5140.330.68990.118289354

151140.830.68760.1156733394

151.5141.330.68550.1132848044

152141.830.68490.1126023658

152.5142.330.68640.1143084622

153142.830.68460.1122611465

153.5143.330.68420.1118061874

154143.830.68420.1118061874

154.5144.330.68450.1121474067

155144.830.68290.1103275705

155.5145.330.6820.1093039126

156145.830.68130.1085077343

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