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
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
7383.65-0.4340.42
73.584.15-0.4360.42
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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
156.5146.330.68030.1073703367
157146.830.6810.108166515
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