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1 1 1 Scheme 1 O 1 SCW + 420, 30 min, 035 g/ml 2 47% 3 31% 1 420, 30 min, 035 g/ml 3 31% 2 48% Scheme 1 Table g/ml min 1 16% 3 36% 5 11% 2 01 g/ml 1 44% 035 g/ml 2 48% 1 O Table 1 Reaction of Triphenylmethanol 1 a density of water / recovery / % yield / % g/ml a Reaction condition : 420, 30 min 1
2 , 2, Figure
3 Supercritical Water Subcritical Water 221 Water Critical Ice Point Steam 374 Tempereture / Figure 1 ase diagram of water MPa Supercritical water : SCW Subcritical water Pressure / MPa 1-21 Table 2 4 3
4 Table 2 ysicochemical properties of water as a function of temperature and pressure nomal water subcritical water supercritical water superheated steam temperature / pressure / MPa density / g/ml η / mpas λ / mw/m K MP ε Figure 2 5 ex : e = 245 : ε = 188 Relative permittivity ε K w log K w / mol 2 /kg Temperature / Figure 2 Temperature dependability of a dielectric constant and an ion product of water in 25 MPa 4
5 25 01 MP mol/l 2 25 MPa mol/l 2 Figure a MPa b c 1-22 Figure 3 6 Figure 3 Pattern diagram of solvation in a supercritical fluid Cage Cage Cage a b Cage I 2 I 2 5 5
6 1-3 Scheme 2 PET 7 8 Scheme 2 2 O OC CO O O OOC COO + O O 400 n 2 min O O C 2 O O O O O O O C 2 O 2 O n s 25 MPa O 2 C O O O O O C 2 O O O O + O O O O O O C 2 O 6
7 Scheme 3 ε Scheme 3 N O 2 O MPa N O O O 2 O O MPa O 2 O MPa O O + O Scheme
8 Scheme 4 O 2 O 460, 3 h 49 MPa O O O O Scheme Scheme 5 NO 2 SCW CO2 + 2O + NO 2 O 2 C3 C3 SCW 2 O 2 C3 CO C COO 2 O Pulse radiolysis O + 8
9 ex a Scheme 6 Scheme 6 O min d = 35 g/ml a 4 2 9
10 a 3 3 a MOPAC b 1 c 1 ESR 10
11 , 30 min, 035 g/ml Table 3 1 NMR 2 48% 3 31% Scheme Scheme 7 O 1 SCW + 420, 30 min, 035 g/ml 2 47% 3 31% 1 Table 3 1 Table 3 Table 4 σ y σ y = n i= 1 σ y σ y = n ( y i y) n 1 2 y = n = 11
12 Table 3 Reaction of substrate 1 in Sub- and Supercritical water temperature / time / density / recovery / % min g/ml total tr b tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr sec tr tr tr tr tr tr tr tr tr tr tr tr tr tr 32 tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr tr 77 a Value of water density g / volume of SUS316 tubular reactor 10 ml b tr : trace c phenylfluorenol(4) d benzophenone(5) a yield / % c d 12
13 Table 4 Average and standard deviation of recovery of 1 and yield of 2, 3, 4, and 5 in Table 3 a b c d e entry a temperature / time / density / recovery / % yield / % min g/ml total (047) 47 (36) 31 (25) tr - tr - 81 (17) (89) 26 (94) 16 (20) 85 (31) tr - 87 (55) (41) 42 (57) 26 (23) 88 (26) tr - 86 (22) b tr - 56 (44) 27 (088) tr - tr - 83 (49) (14) 44 (19) 37 (50) tr - tr - 82 (12) (10) 38 (00) 0 - tr - 85 (10) sec tr (11) 15 (61) 88 (34) 69 (22) tr - 96 (05) (40) 31 (41) 28 (20) 86 (15) tr - 80 (46) (10) 42 (27) 36 (79) tr - tr - 79 (72) (27) tr - 36 (46) 0-11 (19) 63 (58) (005) tr - 35 (30) tr - 42 (12) 83 (20) (50) 73 (20) 47 (65) 39 (045) 38 (046) 85 (25) (12) 28 (52) 42 (32) tr - tr - 71 (71) (30) 42 (78) 32 (34) 18 (11) tr - 82 (19) Value of water density g / volume of SUS316 tubular reactor 10 ml tr : trace phenylfluorenol(4) benzophenone(5) Standard deviation c d 13
14 Figure 4 30 min 035 g/ml O O Total Yield Recovery / % Temperature / Figure 4 Reaction temperature dependability of the recovery of 1 and yield of 2, 3, 4, and total in Table 3 Condition was fixed 30 min, 035 g/ml ,
15 Figure g/ml O O Total Yield Recovery / % Time / min Figure 5 Reaction time dependability of the recovery of 1 and yield 2, 3, 4, and total in Table 3 Condition was fixed 420, 035 g/ml
16 Figure min O O O Total 100 Yield Recovery / % Density / min Figure 6 Water density dependability of the recovery of 1 and yield 2, 3, 4, 5, and total in Table 3 Condition was fixed 420, 30 min 1 d = 0 g/ml 01 g/ml 3 d = 0 g/ml 5 Figure g/ml
17 Scheme 8 Scheme 8 O 2 O O [1,5] 2 Scheme 9 17
18 Scheme 9 O 2 O O [1, 5] [1, 5] min d = 035 g/ml Scheme 10 O 4 48% SCW min, d = 035 g/ml 2 41% 18
19 2 41% 4 48 Scheme 10 Figure min min 2 n-henicosane O 4 n-heptadecane?? Figure 9 GC chart of reaction of 4 in SCW(420, 30 min, d = 035 g/ml) Condition : CBP-5 column, kept for 5 min by 60, increased 5 /min from 60 to 250, kept for 5 min by 250 Figure min min 4 Scheme 11 Scheme 11 O + O 4 19
20 , 30 min, d = 035 g/ml Table 5 Table 5 Stability of 3 in SCW temperature / time / density / recovery / % yield / % min g/ml tr min Figure , 180 min, d = 035 g/ml
21 n-henicosane 3 Figure 10 GC chart of reaction of 3 in SCW(420, 30 min, d = 035 g/ml) Condition : CBP-5 column, kept for 5 min by 60, increased 5 /min from 60 to 250, kept for 5 min by Figure Scheme 11 Scheme 11 O O
22 Scheme 12 Scheme [1,5] [1,5] [1,5] [1,5] MOPAC ESR 1 22
23 3-41 MOPAC 1 3 MOPAC AM1 Figure ε = MOPAC AM1 : Austin Model O 2412 f / (kcal/mol) 389 O 1 O Figure 11 Energy diagram of the reaction of 1 to give kcal/mol 104 kcal/mol 1371 kcal/mol 23
24 3-42 ESR ESR 1 Ar ESR 300, mg / 0141mL g 022 mt Field / mt Figure 12 ESR spectrum of 1 in subcritical water Condition : 300, 033 g/ml Figure 12 g 022mT 24 g 0277mT 24
25 O Scheme 13 Scheme 13 O O O 1 3 9, Scheme Scheme 13 Scheme 13 O O O + O O O O O 25
26 Table 6 Table 6 Reaction of 1 with reducing agent in SCW reducing agent temperature / time / density / recovery / % yield / % min g/ml ,10 -dihydroanthracene > ,5 -di-t -butylhydroquinone no % % % MOPAC ESR d = 0 g/ml % < 1% 2 48% 3 31% Scheme 15 26
27 Scheme 15 neat 420, 30 min O O 5 O 16% (recovery) 36% 11% 1 SCW 420, 30 min, d = % 48% Scheme 15 Scheme 16 1 Cage
28 Scheme 16 O 1 O O [1,5] [1,5] Scheme 16 Scheme 17 4 Scheme 17 28
29 1 4 2 Scheme Scheme 18 O O O Figure Figure d = 0 g/ml 3 36% 5 11% 1 16 Scheme 19 1 Path A Path B Path A 3 Path B 5 29
30 MOPAC Path A 104 kcal/mol Path B 107 kcal/mol Path A 3 kcal/mol 3 Scheme 19 Path A O O f = 104 kcal/mol 3 1 Path B O O f = 107 kcal/mol 5 01 g/ml 0 g/ml Figure g/ml d = 01 g/ml 2 30
31 4 4-1 SUS ml 1 50 mg 0192 mmol 35 ml KNO 3, NaNO 2 n- n- CBP-5, Figure n- 5 n NMR Figure 15 1 NMR CDCl 3 TMS 00 ppm
32 n-henicosane 2 Figure 14 Example of GC chart after the reaction of 1 (420, 30 min, 035 g/ml) 32
33 3 2 Figure 15 Example 1 NMR spectrum after the reaction of 1 (420, 30 min, 035 g/ml) 33
34 min d = 035 g/ml n- CBP-5, min d = 035 g/ml n- n- CBP-5, 4 Figure NMR 2 3 Figure 16 Figure NMR 1 NMR CDCl 3 TMS 00 ppm 2 O n-henicosane 4 n-heptadecane Figure 16 GC chart of reaction of 4 in SCW(420, 30 min, d = 035 g/ml) Condition : CBP-5 column, kept for 5 min by 60, increased 5 /min from 60 to 250, kept for 5 min by
35 4-4 ESR 15 mm 27 mm 0141 ml 1 05 mg mmol or 5 mg mmol 00459mL Ar , 033 g/ml ESR , 30 min, d = 035 g/ml 3 Figure min min n ml GPC Peak A Peak B Figure 18 JAI-GEL 1 JAI-GEL 2 35
36 n-henicosane Figure 17 GC chart of reaction of 1 in SCW(420, 30 min, d = 035 g/ml) Condition : CBP-5 column, kept for 5 min by 60, increased 5 /min from 60 to 250, kept for 5 min by 250 Peak A Peak B Figure 18 GPC chart of sample that is Figure 18 36
37 GPC Peak B Figure min Figure 20 1 NMR Figure 21, C NMR Figure 23 GC-MS 2 1 NMR 400 Mz, CDCl 3 δ 780 d, J = 76 z, 2, m, 7, 709 dd, J = 8, 16 z, 2, 505 s, 1 13 CNMR Mz, CDCl 3 δ C, C, C, C, C, C, C, C, C, 5440 C ; MS EI m/z 242 M + Figure 20 GC spectrum of separated peak B in Figure 19 : Condition : CBP-5 column, kept for 5 min by 60, increased 5 /min from 60 to 250, kept for 5 min by
38 38 Figure 21 1 NMR chart of peak B in Figure
39 39 Figure 22 Magnified figure of Figure 21
40 40 FiFigure C NMR chart of peak B in Figure
41 GPC Peak A Figure min Figure 20 1 NMR Figure 21, 22 GC-MS 3 1 NMR 400 Mz, CDCl 3 δ m, 16, 555 s, 1 ; MS EI m/z 244 M + Figure 20 GC chart of separated peak A in Figure 19 Condition : CBP-5 column, kept for 5 min by 60, increased 5 /min from 60 to 250, kept for 5 min by
42 42 Figure 21 1 NMR chart of separated peak A in Figure 19
43 43 Figure 22 Magnified figure of Figure 21
44 GC-MS GC-MS 4-6 nacalai nacalai Aldrich nacalai n- TCI n- TCI Kanto chemical TMS Aldrich CDCl 3 Aldrich nacalai GC Shimadzu, Co, Ltd, GC-17A CBP-5, Shimadzu, Co, Ltd NMR UNITY INOVA VARIAN 400 Mz GPC Recycle Preparative PLC Japan Analytical Industry Co, Ltd GC-MS Shimadzu, Co, Ltd QP5050 DB-1, J&W Scientific ESR Santry, Co, Ltd 44
45 Cage 1 ESR 45
46 1, Paul T Anastas,,, ,,,,, ,,,,,,,,, Broll, D; Kaul, C; Kramer, A; Krammer, P; Richter, T; Jung, M; Bogel, ; Zehner, P, Angew Chem Int Ed, 1999, 38, Tester, J W; olgate, R; Armellini, F J; Webley, PA; Killilea, WR; ong, GT; Barner, E, ACS Symp Ser, 1993, 518, Chapter 3 6,,, Otto, B; Schoroeder, J; Troe, J J Chem ys, 1984, 81, Sasaki, M ; Kabyemela, B ; Malaluan, R ; irose, S ; Takeda, N ; Adaschiri, T ; Arai, K, Journal of Supercritical Fluids, 1998, 13, Sato, O; Ikushima, Y; Yokoyama, T, J Org Chem, 1998, 63, Ikushima, Y; atakeda, K; Sato, O; Yokoyama, T; Arai M J Am Chem Soc, 2000, 122, Ikushima, Y; atakeda, K; Sato, O; Yokoyama, T; Arai M, Angew Chem IntEd Engl, 1999, 38,
47 12 Ikushima, Y; atakeda, K; Sato, O; Yokoyama, T; Arai M, Angew Chem IntEd Engl, 2001, 40, ,, Arita, T; Nkahara, K; Nagami, K; Kajimoto, O, Tetrahedron Letters, 2002, Takahashi, ; isaoka, S; Nitta, T Chemical ysics Letters, 2002, 363, ,,, ua, I; Zhang, G Ind Eng Chem Res 2003, 42, Yi, S C; Kim, Y L; Kim, J D Lim, J S; Lee, Y W Ind Eng Chem Res 2002, 41, Brenneck, J F; Aki, K chateauneuf, E; J AmChemSoc 2002, 124, Gomberg, M, J Am Chem Soc 1900, 22, Shi, M; Okamoto, Y; Takamuku, S, J Chem Research (M), 1990, Lloyd, D; Walton, J D; Declercq, J P; Germain, G; Meerssche, V M; J Chem Research (S), 1979, Dewar, Michael J S; Zoebisch, Eve G; ealy, Eamonn F; Stewart, James J P J Am Chem Soc 1985, 107,
48 24 Maki, A ; Allendoerfer, R D; Danner, J C; Keys, R T J Am Chem Soc 1968, 31,
49
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