Reaxys
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199
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Heating;
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Rx-ID: 27986161 Find similar reactions
Kumar, B. N. Hitesh; Prakasam; Srinivasan; Arabindoo, Bhanumathi; Ramana
Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008 , vol. 47, # 6 p. 963 - 965 Title/Abstract Full Text View citing articles Show Details
200
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Rx-ID: 4724948
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85%
With sodium carbonate in acetone
1.5 h; Irradiation;
Yang; Cao; Evans; Kabalka
Synthetic Communications, 1996 , vol. 26, # 22 p. 4275 - 4278 Title/Abstract Full Text View citing articles Show Details
84%
With tetraethylammonium bromide; potassium oxide in N,N-dimethyl-formamide
T=30°C; 3.5 h;
Singh, Sundaram; Singh, Manorama; Singh, Krishna Nand
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1998 , vol. 37, # 1 p. 88 - 90 Title/Abstract Full Text Show Details
84%
With sodium hypochlorite in acetonitrile
T=20°C; 1 h;
Khurana; Sharma; Gogia; Kandpal
Organic Preparations and Procedures International, 2007 , vol. 39, # 2 p. 185 - 189 Title/Abstract Full Text View citing articles Show Details
201
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Rx-ID: 9519543 Find similar reactions
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92%
Stage #1: lithium methanoate With acetic anhydride; Nethyl-N,N-diisopropylamine in N,N-dimethyl-formamide
T=20°C; Stage #2: 1-(iodo)-4-methylbenzene With palladium diacetate; lithium chloride in N,N-dimethyl-formamide
T=80°C; 22 h;
Cacchi, Sandro; Fabrizi, Giancarlo; Goggiamani, Antonella
Organic Letters, 2003 , vol. 5, # 23 p. 4269 - 4272 Title/Abstract Full Text View citing articles Show Details
88%
With acetic anhydride; N-ethyl-N,Ndiisopropylamine; lithium chloride; palladium on activated charcoal in N,N-dimethyl-formamide
T=100°C; 24 h;
Cacchi, Sandro; Cotet, Cosmin L.; Fabrizi, Giancarlo; Forte, Giovanni; Goggiamani, Antonella; Martin, Laura; Martinez, Sandra; Molins, Elies; Moreno-Manas, Marcial; Petrucci, Francesco; Roig, Anna; Vallribera, Adelina
Tetrahedron, 2007 , vol. 63, # 11 p. 2519 - 2523 Title/Abstract Full Text View citing articles Show Details
A
B
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202
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A: 84% B: 12%
With sodium hypochlorite in acetonitrile
T=20°C; 0.5 h;
Khurana; Sharma; Gogia; Kandpal
Organic Preparations and Procedures International, 2007 , vol. 39, # 2 p. 185 - 189 Title/Abstract Full Text View citing articles Show Details
203
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With sodium hypochlorite in acetonitrile
T=20°C; 5 h;
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Rx-ID: 11000950 Find similar reactions
Khurana; Sharma; Gogia; Kandpal
Organic Preparations and Procedures International, 2007 , vol. 39, # 2 p. 185 - 189 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
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204
Synthesize Find similar Rx-ID: 11141808 Find similar reactions
With air; cyclohexene; carbon
24 h; Heating;
Sereda, Grigoriy; Rajpara, Vikul
Tetrahedron Letters, 2007 , vol. 48, # 19 p. 3417 - 3421 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
E
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205
Synthesize Find similar Rx-ID: 25760371 Find similar reactions
With Co, Mn, Br catalyst system T=160°C; Oxidation; Product distribution / selectivity; Hide Experimental Procedure
O'Meadhra, Ruairi Seosamh; Lin, Robert
Patent: US2007/179312 A1, 2007 ; Location in patent: Page/Page column 4 ; Title/Abstract Full Text Show Details
1:
Example 1; Paraxylene was oxidized at 160° C. utilizing a Co, Mn, Br catalyst system to produce a crude terephthalic acid slurry having 30-35percent solids. A
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C
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206
Synthesize Find similar Rx-ID: 25971994 Find similar reactions
With oxygen; WOx/SiO2-5.3 in acetonitrile
T=5 - 10°C; 1.5 h; UV-irradiation; Title compound not separated from byproducts.;
Tzirakis, Manolis D.; Lykakis, Ioannis N.; Panagiotou, George D.; Bourikas, Kyriakos; Lycourghiotis, Alexis; Kordulis, Christos; Orfanopoulos, Michael
Journal of Catalysis, 2007 , vol. 252, # 2 p. 178 - 189 Title/Abstract Full Text View citing articles Show Details
207
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Rx-ID: 10038743 Find similar reactions
90%
With toluene-4-sulfonic acid
0.0666667 h; microwave irradiation;
Lee, Jong Chan; Yoo, Eun Sang; Lee, Jin Seo
Synthetic Communications, 2004 , vol. 34, # 16 p. 3017 - 3020 Title/Abstract Full Text View citing articles Show Details
77%
With iodine; dimethyl sulfoxide
0.333333 h; Heating;
Taksande, Kiran N.; Sakate, Sachin S.; Lokhande, Pradeep D.
Tetrahedron Letters, 2006 , vol. 47, # 5 p. 643 - 646 Title/Abstract Full Text View citing articles Show Details
208
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With dihydrogen peroxide; urea; 1-n-butyl-3-
Synthesize Find similar Jong, Chan Lee; Jang, Mi Lee
Rx-ID: 10086698 Find similar reactions
methylimidazolium tetrafluoroborate
Synthetic Communications, 2006 , vol. 36, # 8 p. 1071 - 1074 Title/Abstract Full Text View citing articles Show Details
A
B
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209
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Rx-ID: 10185024 Find similar reactions
A: 80% B: 18%
With silica-supported selenamide; dihydrogen peroxide
T=55°C; 17 h;
Giurg; Brzaszcz; Mlochowski
Polish Journal of Chemistry, 2006 , vol. 80, # 3 p. 417 - 428 Title/Abstract Full Text View citing articles Show Details
A
B
C
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210
Synthesize Find similar Rx-ID: 10199973 Find similar reactions
A: 10% B: 72% C: 18%
With silica-supported selenamide; dihydrogen peroxide in tert-butyl alcohol
T=55°C; 27 h;
Giurg; Brzaszcz; Mlochowski
Polish Journal of Chemistry, 2006 , vol. 80, # 3 p. 417 - 428 Title/Abstract Full Text View citing articles Show Details
A
B
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211
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A: 4% B: 78%
With sodium periodate; sulfuric acid in water
T=95°C; 12 h;
Shaikh, Tanveer Mahammad Ali; Emmanuvel, Lourdusamy; Sudalai, Arumugam
Journal of Organic Chemistry, 2006 , vol. 71, # 13 p. 5043 - 5046 Title/Abstract Full Text View citing articles Show Details
212
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73%
With pyridine; 1,1'-bis(diphenylphosphino)ferrocene; palladium diacetate
T=150°C; 0.333333 h; microwave irradiation;
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Rx-ID: 10453379 Find similar reactions
Lesma, Giordano; Sacchetti, Alessandro; Silvani, Alessandra
Synthesis, 2006 , # 4 p. 594 - 596 Title/Abstract Full Text View citing articles Show Details
213
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Rx-ID: 11133260 Find similar reactions
89%
Stage #1: lithium methanoate With acetic anhydride; Nethyl-N,N-diisopropylamine in N,N-dimethyl-formamide
T=20°C; 1 h; Stage #2: para-bromotoluene With 1,1'-bis(diphenylphosphino)ferrocene; palladium diacetate in N,Ndimethyl-formamide
T=120°C; 2 h; Further stages.;
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Berger, Philippe; Bessmernykh, Alla; Caille, Jean-Claude; Mignonac, Sylviane
Synthesis, 2006 , # 18 p. 3106 - 3110 Title/Abstract Full Text View citing articles Show Details
214
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Multi-step reaction with 2 steps 1: 1-butyl-3-methylimidazolium tetrafluoroborate / 1 h / 60
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Rx-ID: 12613824 Find similar reactions
Jong, Chan Lee; Jang, Mi Lee
Synthetic Communications, 2006 , vol. 36, # 8 p. 1071 - 1074
°C 2: urea; hydrogen peroxide; 1-butyl-3-methylimidazolium tetrafluoroborate View Scheme
Title/Abstract Full Text View citing articles Show Details
A
B
C
D
E
F
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215
Synthesize Find similar Rx-ID: 23747620 Find similar reactions
With oxygen; acetic acid; hydrogen bromide; anhydrous cobalt diacetate; Manganese (II) acetate in water
T=160.3 - 161.2°C; P=4650.47 Torr; 8 h; Pilot scale; Product distribution / selectivity; Hide Experimental Procedure
Wonders, Alan George; Lavoie, Gino Georges; Sumner, Charles Edwan
Patent: US2006/47152 A1, 2006 ; Location in patent: Page/Page column 39-41 ; Title/Abstract Full Text Show Details
3; 4:
Examples 1-4 pertain to pilot-scale oxidations of para-xylene to terephthalic acid conducted in a pilot-scale system assembled around a mechanically agitated, hot-oil jacketed, 2-gallon, titanium reaction vessel. The gas dispersion type agitator within the reaction vessel was rotated at about 1,500 revolutions per minute (rpm), and the power draw of the agitator was about 220 watts. The pilot-scale system was equipped with means to control the pressure and temperature within the reaction vessel and to control the gas and liquid flow rates entering the reaction vessel. The feed of para-xylene was provided via a syringe pump at an effectively steady rate of about 0.28 kilograms per hour. Catalyst feed solution was pumped from a catalyst feed tank into the reaction vessel at an effectively steady rate of about 3.2 kilograms per hour. Both para-xylene and catalyst feed solution were released into the reaction medium through a dip tube ending below the level of aerated slurry within the reaction vessel. Using a nuclear level measurement system, the reaction mass in the reactor was maintained at an indicated value of around 40 percent by automatic operation of a drain valve located near the bottom of the reactor. By calibration, this indicated level corresponded to approximately 3 kilograms of reaction medium. Compressed air was fed effectively continuously through a tube ending below the level of the gas dispersion impeller within the reaction vessel. The off-gas from the reaction vessel was fitted with a condenser system designed to condense most organic vapor from the off-gas. Condensate from the off-gas was removed from the process at a rate of about 1.3 kilogram per hour, and the balance of the off-gas condensate was returned to the reaction vessel. The air feed rate was adjusted to maintain an oxygen concentration in the exiting gas of about 3 to 4 mole percent on a dry basis after the off-gas condenser. The gases exiting the reactor were continuously monitored for oxygen, carbon dioxide, and carbon monoxide using in-line gas analyzers. The product slurry, comprising crude terephthalic acid (CTA) solids, was collected in an unaerated, stirred receiving tank, which was drained batchwise every four hours into a second unaerated tank in which the slurry was cooled to about 40° C. to crystallize additional dissolved product. The resulting cooled slurry was filtered. The filtrate was collected, weighed and analyzed by HPLC-MS for low-level organic compounds, by x-ray for metals, by gas chromatography for methyl acetate and xylene, and by near infrared for water. The moist solids were weighed, and a sample was analyzed for moisture content. A portion of the remaining solids was washed with acetic acid, dried and analyzed by HPLC-MS for specific analytes. The reaction condensate was weighed and analyzed by a gas chromatography method calibrated with known concentrations of the specific analytes. For each oxidation run, the catalyst feed solution was prepared in an agitated catalyst feed tank. The catalyst feed solution contained glacial acetic acid and deionized water. The cobalt in the catalyst feed solution was added as cobaltous acetate tetrahydrate, the manganese was added as manganous acetate tetrahydrate, and the bromine was added as aqueous 48 percent hydrobromic acid. The amounts of each component in the catalyst feed solution were selected to give the reaction slurry compositions shown below. For start-up, the reaction vessel was charged with catalyst feed solution and xylene, was brought to the reaction temperature with a heating oil jacket and pressure, and was concentrated by evaporation to about half volume. Air diluted with nitrogen was introduced into the mixture until an exotherm was observed. Once the reaction was initiated, para-xylene and catalyst feed solution were fed to the reaction at the rates given above. The reaction was sustained at the conditions for about 8 hours before product was retained. Thereafter, slurry product was collected at about 4-hour intervals for the duration of the experiment, and analyses were conducted as stated above. The values for the gas flows, temperature, and pressure were recorded every ten minutes and averaged for each run. For some reactions disclosed below, the as-received, chromatographic (HPLC) grade of para-xylene was further purified by two cycles of partial freeze-thaw crystallization. The levels of several impurities in the feed para-xylene were as shown in Table 5, as determined by gas chromatographic analysis.; Now continuing to Examples 3 and 4, these show that an increase in the liquid-phase concentration of benzoic acid in the liquid-phase of the reaction medium leads to an increase in the rates for several undesirable reactions compared to the rate of production of TPA. In Example 4, the liquid phase concentration of benzoic acid was elevated by intentionally dissolving a desired amount of benzoic acid within the catalyst feed solution. This solution for Example 4, comprising acetic acid, water, cobalt, bromine, manganese and analytical grade benzoic acid, was analyzed by HPLC-MS for low levels of aromatic impurities, which most likely entered the mixture along with the purchased, analytical grade benzoic acid. For both Examples 3 and 4, the net generation of aromatic impurities reported in Table 7 were computed by adding the mass flow of each impurity in all stream exiting the reaction medium and then subtracting the mass flow of the same impurity in all streams entering the reaction medium. For convenience, the net creation rates for impurities are expressed as the weight of impurity produced divided by a theoretical weight of produced TPA computed by multiplying the weight of para-xylene feed times 166/106, the molecular weight ratio of TPA to para-xylene. These values are then multiplied by one million to provide a weight ratio expressed as ppmw. Comparing the results of Examples 3 and 4, note that phthalic acid formation was distinctly elevated by the presence of benzoic acid in the liquid phase of the reaction medium. The creation rate of phthalic acid in Example 4 was about 189 ppmw, which amount is comparable to that created from ortho-xylene impurity present in para-xylene within preferred ranges disclosed herein. Further comparing the results of Examples 3 and 4, note that the presence of benzoic acid in the liquid phase of the reaction medium greatly affected the formation of one colored impurity, 9-fluorenone-2-carboxylic acid, but it did not affect the formation of another colored species, 2,7-dicarboxyfluorenone. Note also that the formation of 4,4'-dicarboxybiphenyl was increased by an order of magnitude in Example 4 and that 4,4'-dicarboxybenzophenone increased significantly. The inventors also disclose that analogous results were observed when the liquid phase of the reaction medium was spiked with isophthalic acid or with phthalic acid in other similar experiments. For example, the creation rate of trimellitic acid was increased when either isophthalic acid or phthalic acid concentration was elevated. For example, specific types of poly-aromatic species, including highly colored 2,7-dicarboxyfluorenone, were consistently and proportionately elevated when isophthalic acid was added to the liquid phase of the reaction medium. Further comparing the results of Examples 3 and 4, note in Examples 4 the substantially increased amount of carbon dioxide, the small decline in carbon monoxide, and the marked shift in the ratio of these two gases, which come from both aromatic sources and acetic acid. Viewed simplistically, the overall carbon loss to carbon oxides in Example 4 was 6 percent greater than in Example 3. The inventors also disclose a similar result of elevated carbon oxide loss was observed in other experiments when the liquid phase of the reaction medium was spiked with concentrations of isophthalic acid or phthalic acid, as well as in repeated experiments using benzoic acid. Also note that the concentration of para-toluic acid in the liquid phase of the reaction medium is elevated in Example 4 compared to Example 3, indicating a somewhat lower level of reactivity. The source of this reactivity suppression is not apparent in the concentrations of catalyst components or of water, nor is it apparent in the reaction temperature or amount of excess oxygen. The inventors also disclose a similar result of lower reactivity was observed in other experiments when the liquid phase of the reaction medium was spiked with concentrations of isophthalic acid or phthalic acid, as well as in repeated experiments using benzoic acid. Thus, the increased creation of impurities undesirable in TPA, the loss of carbon oxides, and the suppression of reactivity appear to result when many aromatic compounds lacking non-aromatic hydrocarbyl groups are present in the liquid phase of the reaction medium at elevated levels. It is therefore desirable to control specified impurities in para-xylene feed, specified impurities in recycled solvent, and the self-generation of specified impurities.
With oxygen; acetic acid; hydrogen bromide; anhydrous cobalt diacetate; Manganese (II) acetate in water
T=160.3 - 161.2°C; P=4650.47 Torr; 8 h; Pilot scale; Product distribution / selectivity; Hide Experimental Procedure
Wonders, Alan George; Lavoie, Gino Georges; Sumner, Charles Edwan; Davenport, Bryan Wayne
Patent: US2006/47153 A1, 2006 ; Location in patent: Page/Page column 39-41 ; Title/Abstract Full Text Show Details
3; 4:
Examples 1-4 pertain to pilot-scale oxidations of para-xylene to terephthalic acid conducted in a pilot-scale system assembled around a mechanically agitated, hot-oil jacketed, 2-gallon, titanium reaction vessel. The gas dispersion type agitator within the reaction vessel was rotated at about 1,500 revolutions per minute (rpm), and the power draw of the agitator was about 220 watts. The pilot-scale system was equipped with means to control the pressure and temperature within the reaction vessel and to control the gas and liquid flow rates entering the reaction vessel. The feed of para-xylene was provided via a syringe pump at an effectively steady rate of about 0.28 kilograms per hour. Catalyst feed solution was pumped from a catalyst feed tank into the reaction vessel at an effectively steady rate of about 3.2 kilograms per hour. Both para-xylene and catalyst feed solution were released into the reaction medium through a dip tube ending below the level of aerated slurry within the reaction vessel. Using a nuclear level measurement system, the reaction mass in the reactor was maintained at an indicated value of around 40 percent by automatic operation of a drain valve located near the bottom of the reactor. By calibration, this indicated level corresponded to approximately 3 kilograms of reaction medium. Compressed air was fed effectively continuously through a tube ending below the level of the gas dispersion impeller within the reaction vessel. The off-gas from the reaction vessel was fitted with a condenser system designed to condense most organic vapor from the off-gas. Condensate from the off-gas was removed from the process at a rate of about 1.3 kilogram per hour, and the balance of the off-gas condensate was returned to the reaction vessel. The air feed rate was adjusted to maintain an oxygen concentration in the exiting gas of about 3 to 4 mole percent on a dry basis after the off-gas condenser. The gases exiting the reactor were continuously monitored for oxygen, carbon dioxide, and carbon monoxide using in-line gas analyzers. The product slurry, comprising crude terephthalic acid (CTA) solids, was collected in an unaerated, stirred receiving tank, which was drained batchwise every four hours into a second unaerated tank in which the slurry was cooled to about 40° C. to crystallize additional dissolved product. The resulting cooled slurry was filtered. The filtrate was collected, weighed and analyzed by HPLC-MS for low-level organic compounds, by x-ray for metals, by gas chromatography for methyl acetate and xylene, and by near infrared for water. The moist solids were weighed, and a sample was analyzed for moisture content. A portion of the remaining solids was washed with-acetic acid, dried and analyzed by HPLC-MS for specific analytes. The reaction condensate was weighed and analyzed by a gas chromatography method calibrated with known concentrations of the specific analytes. For each oxidation run, the catalyst feed solution was prepared in an agitated catalyst feed tank. The catalyst feed solution contained glacial acetic acid and deionized water. The cobalt in the catalyst feed solution was added as cobaltous acetate tetrahydrate, the manganese was added as manganous acetate tetrahydrate, and the bromine was added as aqueous 48 percent hydrobromic acid. The amounts of each component in the catalyst feed solution were selected to give the reaction slurry compositions shown below. For start-up, the reaction vessel was charged with catalyst feed solution and xylene, was brought to the reaction temperature with a heating oil jacket and pressure, and was concentrated by evaporation to about half volume. Air diluted with nitrogen was introduced into the mixture until an exotherm was observed. Once the reaction was initiated, para-xylene and catalyst feed solution were fed to the reaction at the rates given above. The reaction was sustained at the conditions for about 8 hours before product was retained. Thereafter, slurry product was collected at about 4-hour intervals for the duration of the experiment, and analyses were conducted as stated above. The values for the gas flows, temperature, and pressure were recorded every ten minutes and averaged for each run. For some reactions disclosed below, the as-received, chromatographic (HPLC) grade of para-xylene was further purified by two cycles of partial freeze-thaw crystallization. The levels of several impurities in the feed para-xylene were as shown in Table 5, as determined by gas chromatographic analysis. Now continuing to Examples 3 and 4, these show that an increase in the liquid-phase concentration of benzoic acid in the liquid-phase of the reaction medium leads to an increase in the rates for several undesirable reactions compared to the rate of production of TPA. In Example 4, the liquid phase concentration of benzoic acid was elevated by intentionally dissolving a desired amount of benzoic acid within the catalyst feed solution. This solution for Example 4, comprising acetic acid, water, cobalt, bromine, manganese and analytical grade benzoic acid, was analyzed by HPLC-MS for low levels of aromatic impurities, which most likely entered the mixture along with the purchased, analytical grade benzoic acid. For both Examples 3 and 4, the net generation of aromatic impurities reported in Table 7 were computed by adding the mass flow of each impurity in all stream exiting the reaction medium and then subtracting the mass flow of the same impurity in all streams entering the reaction medium. For convenience, the net creation rates for impurities are expressed as the weight of impurity produced divided by a theoretical weight of produced TPA computed by multiplying the weight of para-xylene feed times 166/106, the molecular weight ratio of TPA to para-xylene. These values are then multiplied by one million to provide a weight ratio expressed as ppmw.Comparing the results of Examples 3 and 4, note that phthalic acid formation was distinctly elevated by the presence of benzoic acid in the liquid phase of the reaction medium. The creation rate of phthalic acid in Example 4 was about 189 ppmw, which amount is comparable to that created from ortho-xylene impurity present in para-xylene within preferred ranges disclosed herein. Further comparing the results of Examples 3 and 4, note that the presence of benzoic acid in the liquid phase of the reaction medium greatly affected the formation of one colored impurity, 9-fluorenone-2-carboxylic acid, but it did not affect the formation of another colored species, 2,7-dicarboxyfluorenone. Note also that the formation of 4,4'-dicarboxybiphenyl was increased by an order of magnitude in Example 4 and that 4,4'-dicarboxybenzophenone increased significantly. The inventors also disclose that analogous results were observed when the liquid phase of the reaction medium was spiked with isophthalic acid or with phthalic acid in other similar experiments. For example, the creation rate of trimellitic acid was increased when either isophthalic acid or phthalic acid concentration was elevated. For example, specific types of poly-aromatic species, including highly colored 2,7-dicarboxyfluorenone, were consistently and proportionately elevated when isophthalic acid was added to the liquid phase of the reaction medium. Further comparing the results of Examples 3 and 4, note in Examples 4 the substantially increased amount of carbon dioxide, the small decline in carbon monoxide, and the marked shift in the ratio of these two gases, which come from both aromatic sources and acetic acid. Viewed simplistically, the overall carbon loss to carbon oxides in Example 4 was 6 percent greater than in Example 3. The inventors also disclose a similar result of elevated carbon oxide loss was observed in other experiments when the liquid phase of the reaction medium was spiked with concentrations of isophthalic acid or phthalic acid, as well as in repeated experiments using benzoic acid. Also note that the concentration of para-toluic acid in the liquid phase of the reaction medium is elevated in Example 4 compared to Example 3, indicating a somewhat lower level of reactivity. The source of this reactivity suppression is not apparent in the concentrations of catalyst components or of water, nor is it apparent in the reaction temperature or amount of excess oxygen. The inventors also disclose a similar result of lower reactivity was observed in other experiments when the liquid phase of the reaction medium was spiked with concentrations of isophthalic acid or phthalic acid, as well as in repeated experiments using benzoic acid. Thus, the increased creation of impurities undesirable in TPA, the loss of carbon oxides, and the suppression of reactivity appear to result when many aromatic compounds lacking non-aromatic hydrocarbyl groups are present in the liquid phase of the reaction medium at elevated levels. It is therefore desirable to control specified impurities in para-xylene feed, specified impurities in recycled solvent, and the self-generation of specified impurities. A
B
216
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With hydrogen; Pd/SiC in water
T=277°C; P=2585.81 Torr; 2 h; Product distribution / selectivity; Hide Experimental Procedure
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BP CORPORATION NORTH AMERICA INC.
Patent: WO2006/71407 A1, 2006 ; Location in patent: Page/Page column 24-26 ; Title/Abstract Full Text Show Details
1:
Example 1; A catalyst with palladium supported on silicon carbide (Pd/SiC) was prepared using a silicon carbide in the form of 3 mm diameter extrudate and having a BET surface area of 21 m2/g. The silicon carbide, identified as CTS- 10 from SICAT Corporation, had metallic impurities content of less than about Va wtpercent and was substantially free of silica and of alpha silicon carbide crystallites.The catalyst was prepared by an incipient wetness method in which1.36 grams of palladium nitrate hydrate (38.61 wtpercent Pd) were first dissolved in 16 ml deionized water to which a few drops of concentrated nitric acid had been added. The resulting cloudy solution was then added to 50 g of the silicon carbide in a glass bottle and the bottle was shaken gently for several EPO <DP n="26"/>rtirtUtels.i.tψ 'tnb'r.(C).tlgWl.y.' rti(ιx the solution and solids. The solids were then allowed to dry at room temperature under a flow of nitrogen gas until the liquid had evaporated. The dried solids were charged to a titanium autoclave reactor to which hydrogen was charged under pressure of 200 psi and the autoclave was heated gradually over about V* hour to about 1210C and then allowed to cool, after which the catalyst was removed and dried in a vacuum oven at about 660C overnight. Inductively Coupled Plasma analysis of the resulting solid showed that it contained 0.89 wtpercent Pd, calculated as metal.The activity of the resulting silicon carbide-supported palladium catalyst for purification of an impure terephthalic acid containing 4- carboxybenzaldehyde (4-CBA) was determined by a batch autoclave reaction test. The impure product was a crude terephthalic acid product comprising terephthalic acid and about 3000 ppmw 4-CBA that had been prepared commercially by liquid phase reaction of p-xylene with oxygen in acetic acid solvent using a bromine-promoted, catalyst containing cobalt and manganese at elevated temperature and pressure.A 290 g quantity of the crude terephthalic acid product was dissolved in 116O g deionized water by heating to about 2770C and stirring at 300 rpm in a 1 -gallon, agitated titanium batch autoclave reactor. The reactor had a 20- mesh titanium wire screen basket containing 10 cc of the Pd/SiC catalyst suspended over the liquid phase in the reactor. Weight of catalyst in the screen basket was 8.3 g. Hydrogen was added to the autoclave to a pressure of 50 psia. The agitator stirring rate was increased to 1000 rpm and the screen basket with catalyst was lowered into the liquid phase of the autoclave. Liquid samples were withdrawn at various times after the start of the reaction and analyzed by capillary electrophoresis for 4-CBA, p-toluic acid ("PTOL") and benzoic acid ("BA"). Results are shown in Table 1 below.TABLE 1 EPO <DP n="27"/>For comparison, the procedure described above was repeated using the silicon carbide without added palladium. Results are reported in Table 2.Example 1 and TABLES 1 and 2 indicate that the process using the high surface area silicon carbide-supported catalyst was very effective in reducing the concentration of 4-CBA in the terephthalic acid solution.Concomitant production of p-toluic acid, which is a product of 4-CBA hydrogenation that is more easily removed from terephthalic acid by crystallization, was observed in the process. The silicon carbide without palladium displayed essentially no activity for 4-CBA conversion or production of p-toluic acid.
With hydrogen in water
T=277°C; P=2585.81 Torr; 1 h; Product distribution / selectivity; Hide Experimental Procedure
BP CORPORATION NORTH AMERICA INC.
Patent: WO2006/71407 A1, 2006 ; Location in patent: Page/Page column 30 ; Title/Abstract Full Text Show Details
6:
Example 6; A small quantity of silicon carbide Sample 5A, as described in Example 5, was provided to a commercial catalyst manufacturer for use as a support for preparing an experimental catalyst composition with 0.5 wtpercent palladium. Activity of the resulting catalyst received from the catalyst manufacturer was tested by purifying impure terephthalic acid containing 4-CBA substantially as in Example 1. Results are reported in TABLE 4.TABLE 4Comparing TABLES 1 and 4, it is evident that the decrease in 4-CBA concentration with time was faster in this example than in Example 1 , indicating a more active catalyst in this example than in Example 1. A
B
C
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217
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With hydrogen bromide; oxygen; anhydrous cobalt diacetate; Manganese (II) acetate in water; acetic acid
T=140 - 161°C; P=3087.28 - 5414.51 Torr; 36 h; Product distribution / selectivity; Hide Experimental Procedure
Sumner, Charles Edwan; Hembre, Robert Thomas; Lange, David; Lavoie, Gino Georges; Tennant, Brent Alan; Floyd, Thomas Richard; Davenport, Bryan Wayne; Compton, Daniel Burts; Bays, Joseph Nathaniel
Patent: US2006/205977 A1, 2006 ; Location in patent: Page/Page column 7-10 ; Title/Abstract Full Text Show Details
1-30:
Examples 1-30; In examples 1-30, oxidations of p-xylene to terephthalic acid were carried out in a pilot reactor system assembled around an agitated, hot-oil jacketed, 2-gallon, titanium reaction vessel. The gas dispersion type agitator within the reaction vessel can be rotated at various speeds. At about 1,500 revolutions per minute (rpm), the power draw of the agitator was approximately 210 watts. The pilot reactor system was equipped with means to control the pressure and temperature within the reaction vessel and to control the gas and liquid flow rates entering the reaction vessel. para-Xylene was fed at an effectively steady rate of 2.64 moles per hour via a metering system. Catalyst feed solution was pumped from a catalyst feed tank into the reaction vessel at an effectively steady rate of 7.1 pounds per hour (3.2 kilogram per hour). Both para-xylene and catalyst feed solution were released into the reaction medium through a dip tube ending below the level of aerated slurry within the reaction vessel. Using a nuclear level detection system, the reaction mass in the reactor was maintained at an indicated value of around 40 percent by operation of an automatic drain valve located near the bottom of the reactor. By separate calibration, this indicated level corresponded to approximately 3 kilograms of slurry mass within the aerated, agitated reaction vessel. Air was fed effectively continuously through a tube ending below the level of the gas dispersion impeller within the reaction vessel. The off-gas from the reaction vessel was fitted with a condenser system designed to condense most organic vapor from the off-gas. Condensate from the off-gas was removed from the process at a rate of about 2.8 pounds per hour (1.3 kilogram per hour), and the balance of the off-gas condensate was returned to the reaction vessel. The air feed rate was adjusted to maintain an oxygen concentration in the exiting gas of about 3 to 4 mole percent on a dry basis after the off-gas condenser. The gases exiting the reactor were continuously monitored for oxygen, carbon dioxide, and carbon monoxide with in-line gas analyzers. The product slurry, containing crude terephthalic acid (CTA) solids, was continuously collected in an unaerated, stirred receiving tank kept at a temperature from about 138° C. to about 140° C. This first tank was drained batch-wise every four hours into a second unaerated tank (about 40° C.). The resulting slurry was cooled as rapidly as possible after dropping it from the first tank. It was held in this second tank until the previous sample was removed from the filter. The slurry was then blown through the bag pressure filter, then nitrogen was used to blow most of the filtrate through the filter. The filtrate passing through the bag filter was drained, weighed and sampled without further
processing. A sample of this filtrate was analyzed by liquid chromatography for compositional profile, by X-ray for metals, by gas chromatography for methyl acetate and xylene, and by near infrared for water. Before the next scheduled draining from the first to the second tank, the nitrogen flow was stopped, the bag pressure filter was removed and the wet solids were collected into a sample bag. The wet solids were weighed for calculating a mass balance. A small sample of the wet solids was removed and placed in a moisture balance to measure the percent moisture. About 100 g of the wet solids were collected and placed in a filtration funnel. They were washed at room temperature with acetic acid several times (until the acetic acid picked up no color). The washed solids were then removed from the filtration funnel and dried in a vacuum oven. A sample of these dried solids was analyzed by liquid chromatography. The reaction condensate was weighed and analyzed by gas chromatography and near infrared. For each oxidation run, the catalyst feed solution was prepared in an agitated catalyst feed tank. The catalyst feed solution contained glacial acetic acid and deionized water. The cobalt in the catalyst feed solution was added as cobaltous acetate tetrahydrate, the manganese was added as manganous acetate tetrahydrate, and the bromine was added as aqueous 48 percent hydrobromic acid. The amounts of each component in the catalyst feed solution were selected to give the reaction slurry compositions shown below. For start-up, the reaction vessel was charged with catalyst feed solution and xylene, was brought to the reaction temperature with a heating oil jacket and pressure, and was concentrated by evaporation to about half volume. Air diluted with nitrogen was introduced into the mixture until an exotherm was observed. Once the reaction was initiated, para-xylene and catalyst feed solution were fed to the reaction at the rates given above. The reaction was sustained at the conditions for about 8 hours before product was retained. Thereafter, slurry product was collected at about 4-hour intervals for the duration of the experiment, and analyses were conducted as stated above. The values for the gas flows, temperature, and pressure were recorded every ten minutes and averaged for each run. The concentration of DCF in the solids listed in Tables 1-5 refers to the concentration of 2,6-DCF in the solid isolated using the procedure presented earlier. Likewise, the p-TA in the filtrate refers to the concentration of this reaction intermediate in the filtrate collected as described above. The concentrations of total 2,6-DCF refers to the total concentration of this impurity in the slurry exiting the oxidizer. Table 1 lists results for oxidation runs carried out at 140-143° C. Table 2 lists results for runs at 148-153° C., and Table 3 lists results for 154-158° C. Table 4 contains results for runs at 159-161° C. Table 5 illustrates the relationship between temperature and acetic acid burn at similar conversions.
With cobalt hydroxide; hydrogen bromide; oxygen; Manganese (II) acetate in water
T=145 - 185°C; P=4380.18 - 9551.8 Torr; 8 h; Product distribution / selectivity; Hide Experimental Procedure
Sumner, Charles Edwan; Hembre, Robert Thomas; Lange, David; Lavoie, Gino Georges; Tennant, Brent Alan; Floyd, Thomas Richard; Davenport, Bryan Wayne; Compton, Daniel Burts; Bays, Joseph Nathaniel
Patent: US2006/205977 A1, 2006 ; Location in patent: Page/Page column 11 - 13 ; Title/Abstract Full Text Show Details
37 - 119:
Examples 37-115; The oxidations of p-xylene described in examples 37 to 115 were carried out under conditions different from those used for Examples 1 through 30. Each reaction was performed in a 3-gal titanium agitated autoclave equipped with a means to control the pressure, temperature, gas flow, and a condenser system designed to remove a predetermined amount of condensed vapor from the process. Para-xylene was fed with a metering system at a rate of 330 g/h, and fresh catalyst solution was pumped from a feed tank into the autoclave at a rate of 3330 g/h. The gases exiting the reactor were continuously monitored for oxygen, carbon dioxide, and carbon monoxide with an in-line gas analyzer. The air feed rate was adjusted so as to maintain an oxygen concentration of that listed in the Tables. The level in the reactor was maintained at around 43percent by operation of an automatic drain valve located in the bottom of the reactor. Reaction condensate was removed from the process at a rate of 2390 g/h. The product slurry was continuously collected in a receiving tank, which was drained batch-wise every four hours into a second tank in which the product was cooled to crystallize any dissolved product. The resulting slurry was filtered and the filtrate was collected and weighed and analyzed by liquid chromatography for low-level organic compounds, X-ray for metals, and percent water was determined for the liquid portion by using a Karl Fisher titration procedure. A portion of the remaining solids was washed with acetic acid, dried and analyzed by liquid chromatography. For each oxidation run, the catalyst feed mixture was prepared in the feed tank. The cobalt was added as cobalt hydroxide, the manganese was added as manganous acetate tetrahydrate, and the bromine was added as aqueous hydrobromic acid. The autoclave was charged with catalyst feed and xylene, brought to the reaction temperature and pressure, and was concentrated to about half volume. Air diluted with nitrogen was introduced into the mixture until an exotherm was observed. Once the reaction was initiated, xylene and catalyst were fed to the reaction at the rates given above. The reaction was sustained at the conditions for 8 h before product was retained. The reaction was continued and product was collected at 4-h intervals for a minimum of 20 h. The resulting data points were averaged to give average value for each run for water, organic products, and catalyst concentration. The values for the gas flows, temperature, and pressure were recorded every ten minutes and averaged for each run. The values for the COx/2 listed in these examples correspond to the total molar quantity of CO and CO2 per mole of TPA produced, divided by 2. The concentrations of 2,6-DCF and total p-TA refer to the total concentration of these impurities in the slurry exiting the oxidizer; Examples 112-115; Examples 112-115 (Table 8), conducted as in Examples 37-111 above, further demonstrate that decreasing the temperature alone is not sufficient to decrease the generation rate of 2,6-DCF if the Co:Mn ratio remains low at a value of 17; Examples 116-119 Examples 116-119 were carried out as above in Examples 37-111, and the data set forth in Table 9 below.
218
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93%
With dinitrogen tetraoxide in acetonitrile
T=-20°C; 3 h;
Kim, Yong Hae; Kim, Kweon; Park, Young Jun
Tetrahedron Letters, 1990 , vol. 31, # 27 p. 3893 - 3894 Title/Abstract Full Text View citing articles Show Details
90%
With phthalic anhydride; silica gel
microwave irradiation;
Heravi, Majid M.; Zargarani, Dordaneh; Shoar, Rahim Hekmat; Khaleghi, Shahnaz
Journal of Chemical Research, 2005 , # 2 p. 119 - 120 Title/Abstract Full Text View citing articles Show Details
Gattermann; Schmidt
Justus Liebigs Annalen der Chemie, 1888 , vol. 244, p. 52 Chemische Berichte, 1887 , vol. 20, p. 860 Full Text Show Details
Hide Details
With alkaline solution
With sulfuric acid; sodium nitrite
Gattermann; Schmidt
Justus Liebigs Annalen der Chemie, 1888 , vol. 244, p. 52 Chemische Berichte, 1887 , vol. 20, p. 860 Full Text Show Details
Gattermann
Chemische Berichte, 1899 , vol. 32, p. 1119 Justus Liebigs Annalen der Chemie, 1888 , vol. 244, p. 55 Full Text Show Details
With sodium acetate; acetic acid
T=170°C; also in the presence of ethers of 1,8dioxyxanthones; Rate constant;
Beddoes, Roy S.; Cox, Brian G.; Mills, Owen S.; Mooney, Nichola J.; Watt, C. Ian F.; Kirkland, David; Martin, Daryl
Journal of the Chemical Society. Perkin Transactions 2, 1996 , vol. 10, p. 2091 - 2098 Title/Abstract Full Text View citing articles Show Details
A
B
C
219
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Rx-ID: 9674804 Find similar reactions
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With dipotassium peroxodisulfate; trifluoroacetic acid; palladium (II) trifluoroacetate
T=80°C; 70 h;
Shibahara, Fumitoshi; Kinoshita, Shinsuke; Nozaki, Kyoko
Organic Letters, 2004 , vol. 6, # 14 p. 2437 - 2439 Title/Abstract Full Text View citing articles Show Details
With dipotassium peroxodisulfate; (4-CH3O-C6H4-NCH2)2PO3SCF3; palladium (II) trifluoroacetate in trifluoroacetic acid
T=30°C; 48 h; Title compound not separated from byproducts;
Sakakibara, Ken; Yamashita, Makoto; Nozaki, Kyoko
Tetrahedron Letters, 2005 , vol. 46, # 6 p. 959 - 962 Title/Abstract Full Text View citing articles Show Details
A
B
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220
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With chromium(VI) oxide; perchloric acid; acetic acid; [2,2']bipyridinyl
T=34.85°C; Kinetics; Further Variations:ReagentsTemperatures;
Meenakshisundaram, Subbiah; Gopalakrishnan; Nagarajan; Sarathi; Sumathi
Journal of Chemical Research, 2005 , # 2 p. 73 - 79 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
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221
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Rx-ID: 9883307 Find similar reactions
With oxygen; Co/Mn/Br in water; acetic acid
T=95°C; atmospheric pressure; KineticsProduct distribution; Further Variations:Catalystsamount of water;
Partenheimer, Walt
Advanced Synthesis and Catalysis, 2005 , vol. 347, # 4 p. 580 - 590 Title/Abstract Full Text View citing articles Show Details
A
B
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222
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B: 96 % Chromat.
in water; acetonitrile
6 h; Photolysis; Quantum yield;
Singh, Anil K.; Khade, Prashant K.
Tetrahedron, 2005 , vol. 61, # 42 p. 10007 - 10012 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
E
F
G
H
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223
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With oxygen; hydrogen bromide; anhydrous cobalt diacetate; Manganese (II) acetate in water; acetic acid
T=136.101 - 198.323°C; P=11206.7 - 13171.9 Torr; 1.25 2.8 h; Product distribution / selectivity; Hide Experimental Procedure
Belmonte, Frank G.; Sikkenga, David L.; Ogundiran, Olusola Sunday; Abrams, Kenneth J.; Leung, Linus Kai-Wah; Meller, Christopher G.; Figgins, Dale A.; Mossman, Allen B.
Patent: US2005/107630 A1, 2005 ; Location in patent: Page/Page column 6-12 ; Title/Abstract Full Text Show Details
1; 2; 3; 4; 5; 6; 7; 8; 9; 10; 11; 12; 13; 14; 15; 16; 17; 18; A; B; C.1; C.2; C.3; C.4; C.5; C.6; C.7; C.8; C.9:
Illustrative Examples 1-18 and Comparative Examples A and B The feed solution in each of Illustrative Examples 1-18 and Comparative Examples A and B was made up of measured amounts of solvent (acetic acid and water), catalyst (cobalt acetate, manganese acetate and hydrobromide) and paraxylene (PX), and was stored in a solvent/catalyst/PX feed tank. This feed was pumped into the first reactor at a fixed rate. Amounts of nitrogen and compressed air were mixed to produce a stream that is equal to the volume and had the same oxygen content of the, stream of non-condensable vapor that was withdrawn from the second reactor. Thus the resulting stream of compressed air and nitrogen being fed to the first reactor simulated the composition and volume of the vent stream from the second reactor and was introduced to the first reactor. The first reactor contents were kept well mixed with an agitator. The reactor pressure was maintained at the desired level with a pressure regulator in a vent line for venting non-compressed vent gas from the first reactor. The reactor temperature was regulated with a heater wrapping around the reactor. The reactor level was maintained by opening and closing a valve between the first and the second reactor. For experimental convenience, the first reactor pressure was maintained slightly higher than the second reactor pressure so that material was transferred by differential pressure from the first reactor to the second reactor when that valve was open. The PX and the oxygen reacted in the first reactor to form a reaction solution or slurry containing unreacted PX, oxidation intermediates thereof and terephthalic acid as the final oxidation product. The heat of reaction was removed by vaporizing some of the solvent. The vent stream from the first reactor was sent to a condenser where most of the solvent vapor was condensed. The condensed reflux was either returned to the first reactor or passed to the second reactor or a combination of both. A slip stream of the non-condensable vapor was withdrawn and analyzed to monitor the extent of the reaction. The reaction solution or slurry was passed from the first reactor to the second reactor. Additional solvent and PX were also fed at specified rates to the second reactor. The amount of compressed air added to the second reactor was such that the oxygen concentration in the vent from this reactor was at the desired level. The control of the second reactor was similar to that of the first reactor, except that a small slip stream was removed from the reflux to control the water concentration of the reactor content at the desired level. The oxidation of the PX and its oxidation intermediates in the second reactor were carried to a high degree of completion. The terephthalic acid product was removed from the second reactor through a slugging valve. The specific reaction conditions employed and results for Illustrative Examples 1-18 and Comparative Examples A and B are presented in Tables 1-7. In Tables 1-7, PX, HAc, HMBA, TA, 4CBA and BA represent ylene, acetic acid, hydroxymethylbenzoic acid, terephthalic acid, 4-carboxybenzaldehyde and benzoic acid, respectively. H2O conc in the last column of Table 1 under Reactor Liquid represents the concentration of water in the first reactor that includes the water formed in the oxidation reaction. SCFH means standard cubic feet per hour. HAc burn means the amount of acetic is acid consumed in the example and is reported as pounds of HAc per thousand pounds of PX (lbs/M1bPX). The solvent ratio in Table 4 is reported as pounds of solvent per pound of the total PX feed to both reactors (lb solv./lb total PX feed). OD 340 represents the optical density of TA at 340 nm after it has been recovered, washed and filtered. Comparative Examples 1-9 The same procedure employed for Examples 1-18 was also employed for Comparative Examples 1-9, except that Comparative Examples 1-9 did not employ two oxidation reactors. A single oxidation reactor was employed and was controlled in substantially the same manner as the second oxidation reactor employed in Examples 1-18. All of the components of the reaction mixture were introduced directly into the single oxidation reactor employed. The non-condensable vapor from the oxidation reactor was withdrawn from the reactor as described for the first oxidation reactor in Examples 1-18. The specific reaction conditions employed and the results for Comparative Examples 1-9 are presented in Tables 8-11. The abbreviations and units employed in Tables 8-11 are the same as those employed in Tables 1-7. Comparison of the results of Comparative Examples 4, 5, 6 and 7 with that of Comparative Examples 1, 2, 3 and 8 illustrates that if the vent oxygen is lowered to about 1 volume percent from the normal of about 4 volume percent, the color of the terephthalic acid product, as measured by the optical density (OD 340), will increase significantly and render the TA product unacceptable.
224
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Rx-ID: 5343347 Find similar reactions
95%
With Montmorillonite K-10 clay; toluene
Dealkylation; 0.333333 h; Microwave irradiation;
Gajare, Anil S.; Shaikh, Nadim S.; Bonde, Bhushan K.; Deshpande, Vishnu H.
Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 5 p. 639 - 640 Title/Abstract Full Text View citing articles Show Details
80%
With toluene-4-sulfonic acid
0.0666667 h; microwave irradiation;
Lee, Jong Chan; Yoo, Eun Sang; Lee, Jin Seo
Synthetic Communications, 2004 , vol. 34, # 16 p. 3017 - 3020 Title/Abstract Full Text View citing articles Show Details
A
B
C
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225
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With Sn-Beta zeolite; dihydrogen peroxide in acetonitrile
T=79.85°C; Baeyer-Villiger oxidation; 7 h;
Corma, Avelino; Fornes, Vicente; Iborra, Sara; Mifsud, Maria; Renz, Michael
Journal of Catalysis, 2004 , vol. 221, # 1 p. 67 - 76 Title/Abstract Full Text View citing articles Show Details
With Sn-Beta-2 zeolite; dihydrogen peroxide in 1,4-dioxane
Renz, Michael; Blasco, Teresa; Corma, Avelino; Fornes, Vicente; Jensen, Robert; Nemeth, Laszlo
Chemistry - A European Journal, 2002 , vol. 8, # 20 p. 4708 - 4717 Title/Abstract Full Text View citing articles Show Details
T=80°C; Baeyer-Villiger oxidation; 7 h; Product distribution; Further Variations:Solvents;
With water; oxygen; O2Si0992Sn0008 in 1,4-dioxane
T=80°C; 7 h; Conversion of starting material; Hide Experimental Procedure
CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS; UNIVERSIDAD POLITECNICA DE VALENCIA
Patent: EP1489065 A1, 2004 ; Location in patent: Page 7 ; Title/Abstract Full Text Show Details
7:Example 7
Catalyst A was tested by means of the procedure Oxidation of 4-methoxybenzaldehyde in dioxane and described in Example 6 with 4-n-propoxybenzaldehyde, with 4-methylbenzaldehyde and with benzaldehyde. After 7 hours the conversion and selectivity to the corresponding arylic formiate (1) and substituted phenol (2) and to the corresponding aromatic acid (3) were determined. These results are shown in Table 3. Hide Details
With water; oxygen; O2Si0992Sn0008 in acetonitrile
T=80°C; 7 h; Conversion of starting material; Hide Experimental Procedure
CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS; UNIVERSIDAD POLITECNICA DE VALENCIA
Patent: EP1489065 A1, 2004 ; Location in patent: Page 7 ;
Title/Abstract Full Text Show Details
7:Example 7
Catalyst A was tested by means of the procedure Oxidation of 4-methoxybenzaldehyde in dioxane and described in Example 6 with 4-n-propoxybenzaldehyde, with 4-methylbenzaldehyde and with benzaldehyde. After 7 hours the conversion and selectivity to the corresponding arylic formiate (1) and substituted phenol (2) and to the corresponding aromatic acid (3) were determined. These results are shown in Table 3.
226
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Rx-ID: 9516422 Find similar reactions
2.9%
With potassium hydroxide; [{μ-P,PPPh2CH2PPh2}Co2(CO)4{μ-PPh2CCPPh2}PdCl2]; water
T=25°C; 24 h;
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Hong, Fung-E; Chang, Yu-Chang; Chang, Chin-Pei; Huang, Yi-Luen
Dalton Transactions, 2004 , # 1 p. 157 - 165 Title/Abstract Full Text View citing articles Show Details
227
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Rx-ID: 9519780 Find similar reactions
100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in 1,4-dioxane
2 h; Heating;
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Herbert, John M.
Tetrahedron Letters, 2004 , vol. 45, # 4 p. 817 - 819 Title/Abstract Full Text View citing articles Show Details
A
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C
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228
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With phosphate buffer; dihydrogen peroxide in water
T=30°C; pH=6.0; Kinetics; Further Variations:pHvaluesSolvents;
Nomura, Yasuo; Kubozono, Takayasu; Hidaka, Makoto; Horibe, Mineko; Mizushima, Naoki; Yamamoto, Nobuyuki; Takahashi, Toshio; Komiyama, Makoto
Bioorganic Chemistry, 2004 , vol. 32, # 1 p. 26 - 37 Title/Abstract Full Text View citing articles Show Details
A
B
C
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229
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With phosphate buffer; dihydrogen peroxide in water
T=30°C; pH=6.0; Kinetics; Further Variations:pHvaluesSolvents;
Nomura, Yasuo; Kubozono, Takayasu; Hidaka, Makoto; Horibe, Mineko; Mizushima, Naoki; Yamamoto, Nobuyuki; Takahashi, Toshio; Komiyama, Makoto
Bioorganic Chemistry, 2004 , vol. 32, # 1 p. 26 - 37 Title/Abstract Full Text View citing articles Show Details
A
B
C
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230
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With phosphate buffer; dihydrogen peroxide in water
T=30°C; pH=6.0; Kinetics; Further Variations:pHvaluesSolvents;
Nomura, Yasuo; Kubozono, Takayasu; Hidaka, Makoto; Horibe, Mineko; Mizushima, Naoki; Yamamoto, Nobuyuki; Takahashi, Toshio; Komiyama, Makoto
Bioorganic Chemistry, 2004 , vol. 32, # 1 p. 26 - 37 Title/Abstract Full Text View citing articles Show Details
A
B
C
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231
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With phosphate buffer; dihydrogen peroxide in water
T=30°C; pH=6.0; Kinetics; Further Variations:pHvaluesSolvents;
Nomura, Yasuo; Kubozono, Takayasu; Hidaka, Makoto; Horibe, Mineko; Mizushima, Naoki; Yamamoto, Nobuyuki; Takahashi, Toshio; Komiyama, Makoto
Bioorganic Chemistry, 2004 , vol. 32, # 1 p. 26 - 37 Title/Abstract Full Text View citing articles Show Details
A
B
C
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232
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With phosphate buffer; dihydrogen peroxide in water
T=30°C; pH=6.0; Kinetics; Further Variations:pHvaluesSolvents;
Nomura, Yasuo; Kubozono, Takayasu; Hidaka, Makoto; Horibe, Mineko; Mizushima, Naoki; Yamamoto, Nobuyuki; Takahashi, Toshio; Komiyama, Makoto
Bioorganic Chemistry, 2004 , vol. 32, # 1 p. 26 - 37 Title/Abstract Full Text View citing articles Show Details
A
B
C
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233
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With phosphate buffer; dihydrogen peroxide in water
T=30°C; pH=6.0; Kinetics; Further Variations:pHvaluesSolvents;
Nomura, Yasuo; Kubozono, Takayasu; Hidaka, Makoto; Horibe, Mineko; Mizushima, Naoki; Yamamoto, Nobuyuki; Takahashi, Toshio; Komiyama, Makoto
Bioorganic Chemistry, 2004 , vol. 32, # 1 p. 26 - 37 Title/Abstract Full Text View citing articles Show Details
A
B
C
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234
Rx-ID: 22986488 Find similar reactions
Daicel Chemical Industries, Ltd.
Patent: EP1452517 A1, 2004 ; Location in patent: Page 6 ;
Title/Abstract Full Text Show Details
A
B
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235
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Rx-ID: 9382550 Find similar reactions
With methanol; oxygen
T=20°C; Irradiation; Title compound not separated from byproducts;
Oecal, Nueket; Yano, Lovelle M.; Erden, Ihsan
Tetrahedron Letters, 2003 , vol. 44, # 36 p. 6947 - 6949 Title/Abstract Full Text View citing articles Show Details
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D
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236
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A: 5% B: 24% C: 3% D: 60%
With oxygen; acetic acid; 1,3,5-trihydroxyhexahydro-1,3,5triazine-2,4,6-trione; anhydrous cobalt diacetate
T=100°C; P=760 Torr; 6 h;
Hirai, Naruhisa; Sawatari, Naoko; Nakamura, Norihiro; Sakaguchi, Satoshi; Ishii, Yasutaka
Journal of Organic Chemistry, 2003 , vol. 68, # 17 p. 6587 - 6590 Title/Abstract Full Text View citing articles Show Details
A
237
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Rx-ID: 9455678 Find similar reactions
With aluminum tri-bromide in benzene
T=20°C; P=22501.8 Torr; 3 h; Title compound not separated from byproducts;
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Hattori, Tetsutaro; Suzuki, Yutaka; Miyano, Sotaro
Chemistry Letters, 2003 , vol. 32, # 5 p. 454 - 455 Title/Abstract Full Text View citing articles Show Details
A
B
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238
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Rx-ID: 9455917 Find similar reactions
With aluminum tri-bromide in benzene
T=20°C; P=22501.8 Torr; 3 h; Title compound not separated from byproducts;
Hattori, Tetsutaro; Suzuki, Yutaka; Miyano, Sotaro
Chemistry Letters, 2003 , vol. 32, # 5 p. 454 - 455 Title/Abstract Full Text View citing articles Show Details
A
B
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239
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With aluminum tri-bromide in benzene
T=20°C; P=22501.8 Torr; 3 h; Title compound not separated from byproducts;
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Hattori, Tetsutaro; Suzuki, Yutaka; Miyano, Sotaro
Chemistry Letters, 2003 , vol. 32, # 5 p. 454 - 455 Title/Abstract Full Text View citing articles Show Details
A
240
B
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Rx-ID: 9455920 Find similar reactions
With aluminum tri-bromide in benzene
T=20°C; P=22501.8 Torr; 3 h; Title compound not separated from byproducts;
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Hattori, Tetsutaro; Suzuki, Yutaka; Miyano, Sotaro
Chemistry Letters, 2003 , vol. 32, # 5 p. 454 - 455 Title/Abstract Full Text View citing articles Show Details
241
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Rx-ID: 9519545 Find similar reactions
62%
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Stage #1: potassium formiate With acetic anhydride; Nethyl-N,N-diisopropylamine in N,N-dimethyl-formamide
T=20°C; Stage #2: 1-(iodo)-4-methylbenzene With tris(dibenzylideneacetone)dipalladium (0); lithium chloride in N,N-dimethyl-formamide
T=80°C; 21 h;
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Cacchi, Sandro; Fabrizi, Giancarlo; Goggiamani, Antonella
Organic Letters, 2003 , vol. 5, # 23 p. 4269 - 4272 Title/Abstract Full Text View citing articles Show Details
242
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Rx-ID: 23923572 Find similar reactions
95%
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With hydrogenchloride; sodium sulfate; OsO4 in ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol
Board of Trustees of MICHIGAN STATE UNIVERSITY
Patent: US2003/149299 A1, 2003 ;
Hide Experimental Procedure
Title/Abstract Full Text Show Details
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23:EXAMPLE 23
EXAMPLE 23 This example shows the oxidation of 4,4-dimethyl stilbene using Condition A. 4,4'-Dimethyl stilbene (10 mg) was dissolved in DMF (1 mL), and OsO4 (0.006 mL, 2.5percent in tBuOH) was added and stirred for 5 min. OXONE (0.118 g) was added in one portion and the reaction had a final volume (1.2 mL). The reaction was stirred at room temperature for 3 hours or until the solution becomes colorless. This usually marks the completion of the reaction which was verified by TLC or GC. Na2SO3 (60 mg) was added, to reduce the remaining Os(VIII), and stirred for an additional hour or until solution became dark brown/black. EtOAc was added to extract the products and 1N HCl was used to dissolve the salts. The organic extract was washed with 1N HCl (10 mL*3) and brine (10 mL), dried over Na2SO4, and the solvent was removed under reduced pressure to obtain the crude product. 4-Methyl benzoic acid was obtained in 95percent yield without the need for further purification.
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A
B
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243
Rx-ID: 24145672 Find similar reactions
E. I. du Pont de Nemours and Company
Patent: US6548698 B1, 2003 ;
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Title/Abstract Full Text Show Details
8.b:(b)
(b) Reaction A mixture of toluene (5 mL), trifluoroacetic anhydride (1 mL), and the catalyst solution as prepared above (0.3 mL) was pressurized, at room temperature, with air (1000 psig) and CO (120 psig). The resulting mixture was stirred at 200° C. for 2 hours. After the mixture was cooled down to room temperature, the solvents were evaporated. The residue was redissolved in ether and analyzed by GC-MS with chlorobenzene as an internal standard. A mixture of p-toluic acid and m-toluic acid (70:30) was produced with TON=20, along with trace amounts of o-toluic acid.
244
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Rx-ID: 24208830 Find similar reactions
420 mg (91%)
With NMM; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate in water; N,N-dimethyl-formamide
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QIAGEN Genomics, Inc.
Patent: US6623928 B2, 2003 ; Title/Abstract Full Text Show Details
19.B:Example 19
B. To a solution of Boc-5-aminopentanoic acid (1.09 mmol) and NMM (3.27 mmol) in dry DMF (6 ml), was added HATU (1.14 mmol) and the reaction mixture stirred at room temperature for 0.5 hours. A solution of compound 3 (1.20 mmol) in dry DMF (1 ml) was added and the reaction mixture stirred at room temperature for 18 hours. The reaction was diluted with EtOAc (50 ml) and washed with 1.0 M HCl (2*50 ml) and D.I. H2O (2*50 ml). The organic extracts were dried (MgSO4) and evaporated to dryness. The residue was subjected to column chromatography to give 420 mg (91percent) of compound 4: 1H NMR (DMSO-d6): δ8.65 (d, 1H), 7.88 (d, 1H), 7.65 (m, 2H), 7.48 (t, 1H), 6.73 (br s, 1H), 5.85 (m, 1H), 5.55 (m, 1H), 5.23 (q, 2H), 4.55 (d, 2H), 2.80 (m, 2H), 2.05 (t, 2H), 1.33 (s, 9H), 1.20-1.30 (m, 4H). A
B
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A: 90%
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Rx-ID: 24217464 Find similar reactions
Daicel Chemical Industries, Ltd.
Patent: EP1338336 A1, 2003 ; Title/Abstract Full Text Show Details
4:EXAMPLE 4
EXAMPLE 4 A mixture of 2 mmol of p-xylene, 0.1 mmol of N-acetoxyphthalimide, 0.01 mmol of cobalt(II) acetate and 3 ml of acetic acid was stirred at 150OEC in an atmosphere of air (30 atm = 3 MPa) for 3 hours and thereby yielded terephthalic acid in a yield of 90percent. The yield of p-toluic acid was less than 1percent.
B: 76%
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Daicel Chemical Industries, Ltd.
Patent: US5958821 A1, 1999 ; Title/Abstract Full Text Show Details
E.4:Example E4
Example E4 The reaction was carried out in the same manner as Example E3 except that the stirring was effected at 100° C. for 6 hours, and, as a result, p-xylene was transformed into terephthalic acid (yield 9percent) and p-methylbenzoic acid (yield 76percent) with a transformation rate of 99 percent.
B: 63%
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Mitsubishi Chemical Corporation
Patent: US5760288 A1, 1998 ; Title/Abstract Full Text Show Details
4:Example 4
Example 4 A 500-milliliter titanium autoclave fitted with a reflux condenser and a stirrer was charged with 150 ml of a 0.57M-H3 BO3 buffer solution (pH=5.1) and 10.35 g of p-xylene. To this solution was added a deficient silicotungstate having Ru incorporated therein K5 SiRu(H2 O)W11 O39! such that the Ru concentration reached 1,656 ppm. The inside of the autoclave was purged with nitrogen, and it was heated to 200° C. When the temperature reached 200° C., air was fed under pressure of 6 MPa continuously at a rate of 39 Nl/hr for 2 hours. Subsequently, the reactor was cooled, and the contents were withdrawn therefrom. The product was separated through filtration. The resulting product was analyzed through high-performance liquid chromatography and gas chromatography. As a result, the conversion of p-xylene was 94percent. Relative to p-xylene charged, the yield of terephthalic acid was 63percent, and the yield of p-toluic acid was 9percent. The by-product was mainly CO2 formed through burning. Hide Details
B: 42%
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Daicel Chemical Industries, Ltd.
Patent: US5958821 A1, 1999 ; Title/Abstract Full Text Show Details
E.6:Example E6
Example E6 The procedure of Example E5 was repeated except that the stirring was effected at a temperature of 100° C. for 6 hours. As a result, p-xylene was transformed into terephthalic acid (yield 57percent) and p-methylbenzoic acid (yield 42percent) with a transformation rate of 99 percent. B: 27%
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Daicel Chemical Industries, Ltd.
Patent: US5958821 A1, 1999 ; Title/Abstract Full Text Show Details
E.5:Example E5
Example E5 To 25 milliliters of acetic acid were added 1.06 grams (10 millimoles) of p-xylene, 0.16 gram (1 millimole) of N-hydroxyphthalimide and 0.018 gram (0.05 millimole) of acetylacetonatocobalt(II) Co(AA)2, and the resultant mixture was stirred in an oxygen atmosphere at a temperature of 100° C. for 12 hours. With a transformation rate of 99 percent, p-xylene was transformed into terephthalic acid (yield 70percent) and p-methylbenzoic acid (yield 27percent).
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Daicel Chemical Industries, Ltd.
Patent: EP1338336 A1, 2003 ; Title/Abstract Full Text Show Details
1:EXAMPLE 1
EXAMPLE 1 A mixture of 2 mmol of p-xylene, 0.4 mmol of N-acetoxyphthalimide, 0.01 mmol of cobalt(II) acetate, 0.01 mmol of manganese (II) acetate and 5 ml of acetic acid was stirred at 100OEC in an atmosphere of oxygen gas (1 atm = 0.1 MPa) for 14 hours and thereby yielded terephthalic acid and p-toluic acid in yields of 92percent and 1percent, respectively.
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Daicel Chemical Industries, Ltd.
Patent: EP1338336 A1, 2003 ; Title/Abstract Full Text Show Details
2:EXAMPLE 2
EXAMPLE 2 A mixture of 2 mmol of p-xylene, 0.4 mmol of N-acetoxyphthalimide, 0.01 mmol of cobalt(II) acetate and 5 ml of acetic acid was stirred at 100OEC in an atmosphere of oxygen gas (1 atm = 0.1 MPa) for 14 hours and thereby yielded terephthalic acid and p-toluic acid in yields of 91percent and 1percent, respectively.
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Daicel Chemical Industries, Ltd.
Patent: EP1338336 A1, 2003 ; Title/Abstract Full Text Show Details
3:EXAMPLE 3
EXAMPLE 3 A mixture of 2 mmol of p-xylene, 0.2 mmol of N-acetoxyphthalimide, 0.01 mmol of cobalt(II) acetate and 2 ml of acetic acid was stirred at 100OEC in an atmosphere of oxygen gas (1 atm = 0.1 MPa) for 14 hours and thereby yielded terephthalic acid and p-toluic acid in yields of 89percent and 1percent, respectively. A
B
C
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246
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A: 2 % Spectr. B: 20% C: 5 % Spectr.
With magnesium
T=600°C; P=0.01 - 0.1 Torr;
Aitken, R. Alan; Hodgson, Philip K.G.; Morrison, John J.; Oyewale, Adebayo O.
Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 3 p. 402 - 415 Title/Abstract Full Text View citing articles Show Details
A
247
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Rx-ID: 9007358 Find similar reactions
With N -hydroxyphthalimide; oxygen; cobalt(II) acetate in acetic acid
T=100°C; 3 h; Title compound not separated from byproducts.;
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Minisci, Francesco; Punta, Carlo; Recupero, Francesco; Fontana, Francesca; Franco Pedulli, Gian
Journal of Organic Chemistry, 2002 , vol. 67, # 8 p. 2671 - 2676 Title/Abstract Full Text View citing articles Show Details
A
B
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248
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Rx-ID: 9055709 Find similar reactions
A: 80% B: 8%
With 4 A molecular sieve; sodium carbonate; bis(benzonitrile)palladium(II) dichloride; 1-[2(dicyclohexylphosphino)ferrocenyl]ethyldicyclohexylphosphine T=145°C; P=750.06 Torr; 16 h;
Maegerlein, Wolfgang; Indolese, Adriano F; Beller, Matthias
Journal of Organometallic Chemistry, 2002 , vol. 641, # 1-2 p. 30 - 40 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
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249
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With dihydrogen peroxide; manganese bromide tetrahydrate in water
Dunn, Jennifer B.; Urquhart, Douglas I.; Savage, Phillip E.
Advanced Synthesis and Catalysis, 2002 , vol. 344, # 3-4 p. 385 - 392
T=380°C; Product distribution; Further Variations:water density; contents of reagent, catalyst, title comp.;
Title/Abstract Full Text View citing articles Show Details
250
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91%
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Rx-ID: 9129759 Find similar reactions
Lakouraj, Moslem M.; Movassagh, Barahman; Bahrami, Kyumars
Monatshefte fur Chemie, 2002 , vol. 133, # 9 p. 1193 - 1196 Title/Abstract Full Text View citing articles Show Details
With Amberlyst A-26 (OH-); dihydrogen peroxide in 1,4dioxane
T=20°C; 12 h;
A
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C
D
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A
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D
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251
Synthesize Find similar Rx-ID: 9130127 Find similar reactions
With oxygen; CoSBA-15 in acetic acid
T=129.85°C; P=1520 Torr; 16 h; Product distribution; Further Variations:CatalystsPressuresTemperaturestime;
Burri, Raju; Jun, Ki-Won; Kim, Young-Ho; Kim, Ji Man; Park, Sang-Eon; Yoo, Jin S.
Chemistry Letters, 2002 , # 2 p. 212 - 213 Title/Abstract Full Text View citing articles Show Details
252
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Rx-ID: 9142644 Find similar reactions
A: 3.6% B: 5.3%
With oxygen; CoSBA-15 in acetic acid
T=129.85°C; P=15200 Torr; 3 h; Further byproducts given;
Burri, Raju; Jun, Ki-Won; Kim, Young-Ho; Kim, Ji Man; Park, Sang-Eon; Yoo, Jin S.
Chemistry Letters, 2002 , # 2 p. 212 - 213
C: 4.1% D: 36.1%
Title/Abstract Full Text View citing articles Show Details
A
B
C
D
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A
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C
D
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253
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Rx-ID: 9142645 Find similar reactions
A: 12.6% B: 0.7% C: 1.1% D: 76.6%
With oxygen; Manganese (II) acetate; cobalt(II) dibromide in acetic acid
T=129.85°C; P=1520 Torr; 16 h; Further byproducts given;
Burri, Raju; Jun, Ki-Won; Kim, Young-Ho; Kim, Ji Man; Park, Sang-Eon; Yoo, Jin S.
Chemistry Letters, 2002 , # 2 p. 212 - 213 Title/Abstract Full Text View citing articles Show Details
254
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Rx-ID: 9142646 Find similar reactions
A: 82.7% B: 0.7% C: 0.6% D: 3.8%
With oxygen; Manganese (II) acetate; cobalt(II) dibromide in acetic acid
T=189.85°C; P=15200 Torr; 3 h; Further byproducts given;
Burri, Raju; Jun, Ki-Won; Kim, Young-Ho; Kim, Ji Man; Park, Sang-Eon; Yoo, Jin S.
Chemistry Letters, 2002 , # 2 p. 212 - 213 Title/Abstract Full Text View citing articles Show Details
A
B
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255
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With hydrogen cation in water
Aronova; Ginak
Russian Journal of Applied Chemistry, 2002 , vol. 75, # 1 p. 164 - 165 Title/Abstract Full Text View citing articles Show Details
A
B
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256
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A: 89% B: 4%
With dihydrogen peroxide; poly(bis-9,10anthracenyl)diselenide in tert-butyl alcohol
T=55°C; 7 h;
Giurg; Mlochowski; Ambrozak
Polish Journal of Chemistry, 2002 , vol. 76, # 12 p. 1713 - 1720 Title/Abstract Full Text View citing articles Show Details
A
B
C
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257
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A: 68% B: 10% C: 13%
With dihydrogen peroxide; sodium carbonate; acetonitrile
T=55°C; 24 h;
Giurg; Mlochowski; Ambrozak
Polish Journal of Chemistry, 2002 , vol. 76, # 12 p. 1713 - 1720 Title/Abstract Full Text View citing articles Show Details
258
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91%
With Oxonereg;; osmium(VIII) oxide in N,N-dimethyl-
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Rx-ID: 9242357 Find similar reactions
Travis, Benjamin R.; Narayan, Radha S.; Borhan, Babak
formamide; tert-butyl alcohol
T=20°C; 3 h;
Journal of the American Chemical Society, 2002 , vol. 124, # 15 p. 3824 - 3825 Title/Abstract Full Text View citing articles Show Details
A
B
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259
Synthesize Find similar Rx-ID: 10401962 Find similar reactions
With hydroxide in water; dimethyl sulfoxide
T=25°C; Alkaline hydrolysis; Kinetics;
Um, Ik-Hwan; Han, Hyun-Joo; Ahn, Jung-Ae; Kang, Swan; Buncel, Erwin
Journal of Organic Chemistry, 2002 , vol. 67, # 24 p. 8475 - 8480 Title/Abstract Full Text View citing articles Show Details
260
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Multi-step reaction with 2 steps 1: H+ / H2O View Scheme
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Rx-ID: 14697355 Find similar reactions
Aronova; Ginak
Russian Journal of Applied Chemistry, 2002 , vol. 75, # 1 p. 164 - 165 Title/Abstract Full Text View citing articles Show Details
A
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C
D
E
F
G
H
I
J
K
L
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261
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B: 0% G: 0% H: 0%
With oxygen; manganese bromide tetrahydrate in water
T=200 - 400°C; P=187519 Torr; 0.0025 0.213333 h; Industry scaleNear supercritical condition;
E.I. DU PONT DE NEMOURS AND COMPANY
Patent: WO2002/6201 A1, 2002 ; Location in patent: Page 28 ;
J: 0%
Title/Abstract Full Text Show Details
262
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Rx-ID: 24066292 Find similar reactions
in diethylene glycol dimethyl ether; ethylene glycol
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Larhed, Mats; Alterman, Mathias; Wan, Yiqian; Hallberg, Anders; Kaiser, Nils-Fredrik
Patent: US2002/161266 A1, 2002 ; Title/Abstract Full Text Show Details
1.2:Type I: Carbonylation
Utilizing the SmithSynthesizer 0.200 mL 4 M K2CO3(aq), 0.700 mL diglyme, 0.300 mL ethylene glycol and p-tolyl iodide (0.229 mmol, 0.100 mL of a stock solution of 1.00 g (4.59 mmol) p-tolyl iodide in 2.00 mL diglyme) were dispensed into the microwave tube. The tube was sealed (Crymper-seal) and the mixture was heated by microwaves at 150° C. for 15 minutes. The mixture turned black during irradiation. Thereafter, 1 mL of 12 M HCl(aq) was added to the reaction mixture. The reaction mixture gets warm! The cold crude acidic mixture was extracted 2-3 times with diethyl ether. The separated diethyl ether phases was subsequently extracted twice with 2 M NaOH(aq). Finally, the carboxylic acid 3 was precipitated by addition of 12 M HCl(aq) to the combined NaOH(aq)-phases and extracted into diethyl ether. A
B
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263
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A: 50% B: 40%
With sulfuric acid; dihydrogen peroxide; boric acid in tetrahydrofuran; water
T=60°C; Oxidation; 48 h;
Roy, Amrita; Reddy; Mohanta, Pramod K.; Ila; Junjappa
Synthetic Communications, 1999 , vol. 29, # 21 p. 3781 - 3791 Title/Abstract Full Text View citing articles Show Details
With sodium perchlorate; PMS in water; acetic acid
oxidation at various percentage of acetic acid, in the presence or absence of atmospheric oxiper, ΔH(excit.), ΔS(excit.) and ΔG(excit.) were given; Product distributionThermodynamic data;
Renganathan, Rajalingam; Maruthamuthu, Pichai
Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1986 , p. 285 - 290 Title/Abstract Full Text Show Details
A: 63 % Chromat. B: 22 % Chromat.
With PMP in ethanol; water
T=25°C; var pH; Rate constant;
Ogata, Yoshiro; Sawaki, Yasuhiko; Tsukamoto, Yasuyuki
Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 7 p. 2061 - 2064 Title/Abstract Full Text Show Details
Hide Details
With anhydrous butyl ether; bis[3,5bis(trifluoromethyl)diphenyl] diselenide in 2,2,2trifluoroethanol
T=20°C; Baeyer-Villiger oxidation; 2 h;
Ten Brink; Vis; Arends; Sheldon
Journal of Organic Chemistry, 2001 , vol. 66, # 7 p. 2429 - 2433 Title/Abstract Full Text View citing articles Show Details
264
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Rx-ID: 2945554 Find similar reactions
96%
With sodium hydroxide in water; tert-butyl alcohol
T=70°C; Ni-anode, 16 mA/cm2;
Borsotti; Foa; Gatti
Synthesis, 1990 , # 3 p. 207 - 208 Title/Abstract Full Text View citing articles Show Details
68%
With 4 Angstroem MS; [Me(n-C8H17)3N]HSO4; sodium tungstate
T=90°C; 18 h;
Shi; Feng
Journal of Organic Chemistry, 2001 , vol. 66, # 9 p. 3235 - 3237 Title/Abstract Full Text View citing articles Show Details
265
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100%
With tetrabutyl ammonium fluoride in tetrahydrofuran
Product distribution;
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Rx-ID: 8781438 Find similar reactions
Sawada, Daisuke; Ito, Yukishige
Tetrahedron Letters, 2001 , vol. 42, # 13 p. 2501 - 2504 Title/Abstract Full Text View citing articles Show Details
266
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Rx-ID: 8798146
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95%
With sodium hydroxide
0.0166667 h; microwave irradiation;
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Matloubi Moghaddam; Ghaffarzadeh
Synthetic Communications, 2001 , vol. 31, # 2 p. 317 - 321 Title/Abstract Full Text View citing articles Show Details
A
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C
D
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267
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A: 82% D: 4%
With 2-hydroxy-1,3-isoindolinedione; oxygen; Manganese (II) acetate; anhydrous cobalt diacetate in acetic acid
T=100°C; P=760 Torr; 14 h; KineticsProduct distribution; Further Variations:CatalystsReagentsSolventsTemperaturesratio;
Tashiro, Yasutaka; Iwahama, Takahiro; Sakaguchi, Satoshi; Ishii, Yasutaka
Advanced Synthesis and Catalysis, 2001 , vol. 343, # 2 p. 220 - 225 Title/Abstract Full Text View citing articles Show Details
A
B
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268
Synthesize Find similar Rx-ID: 8824400 Find similar reactions
A: 60% B: 19%
With C2H2Cl2F3O2V; oxygen in tert-butyl alcohol
T=50°C; 3 h;
Hirao, Toshikazu; Morimoto, Chihiro; Takada, Takashi; Sakurai, Hidehiro
Tetrahedron Letters, 2001 , vol. 42, # 10 p. 1961 - 1963 Title/Abstract Full Text View citing articles Show Details
A
269
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B
C
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A: 12% B: 64% C: 19%
With oxygen; vanadyl chloride diisopropoxide in tert-butyl alcohol
T=50°C; 3 h;
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Hirao, Toshikazu; Morimoto, Chihiro; Takada, Takashi; Sakurai, Hidehiro
Tetrahedron, 2001 , vol. 57, # 24 p. 5073 - 5079 Title/Abstract Full Text View citing articles Show Details
270
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100%
With C2H2Cl2F3O2V; oxygen in tert-butyl alcohol
T=50°C; 36 h;
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Rx-ID: 8824402 Find similar reactions
Hirao, Toshikazu; Morimoto, Chihiro; Takada, Takashi; Sakurai, Hidehiro
Tetrahedron Letters, 2001 , vol. 42, # 10 p. 1961 - 1963 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
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B
C
271
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Rx-ID: 8832524 Find similar reactions
With dipotassium peroxodisulfate; trifluoroacetic acid; rhodium(III) trifluoroacetate
T=50 - 55°C; P=760.051 Torr; 16 h; KineticsProduct distribution; Further Variations:CatalystsReagentsTemperaturesPressuresratio;
Grushin, Vladimir V.; Marshall, William J.; Thorn, David L.
Advanced Synthesis and Catalysis, 2001 , vol. 343, # 2 p. 161 - 165 Title/Abstract Full Text View citing articles Show Details
A
272
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Rx-ID: 8880763 Find similar reactions
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A
B
C
D
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A: 1% B: 1% C: 68%
With copper diacetate; [Rh3O(OAc)6(H2O)3]OAc in acetic acid
T=25°C; 20 h;
Uemura; Ohe; Motofusa
Bulletin of the Chemical Society of Japan, 2001 , vol. 74, # 7 p. 1343 - 1348 Title/Abstract Full Text View citing articles Show Details
A: 41% B: 3% C: 14%
With copper dichloride; Rhodium trichloride in acetonitrile
T=25°C; 20 h;
Uemura; Ohe; Motofusa
Bulletin of the Chemical Society of Japan, 2001 , vol. 74, # 7 p. 1343 - 1348 Title/Abstract Full Text View citing articles Show Details
273
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Rx-ID: 8880765 Find similar reactions
A: 47% B: 3% D: 1%
With copper dichloride; palladium dichloride in acetic acid
T=25°C; 20 h;
Uemura; Ohe; Motofusa
Bulletin of the Chemical Society of Japan, 2001 , vol. 74, # 7 p. 1343 - 1348 Title/Abstract Full Text View citing articles Show Details
274
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275
With tetrabutylammonium (meta)periodate in 1,4-dioxane
2 h; Heating;
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Rx-ID: 8913028 Find similar reactions
Lee, Jong Chan; Choi, Ju-Hee; Lee, Yong Chan
Synlett, 2001 , # 10 p. 1563 - 1564 Title/Abstract Full Text Show Details
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With tetrabutylammonium (meta)periodate in 1,4-dioxane
2 h; Heating;
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Rx-ID: 8913034 Find similar reactions
Lee, Jong Chan; Choi, Ju-Hee; Lee, Yong Chan
Synlett, 2001 , # 10 p. 1563 - 1564 Title/Abstract Full Text Show Details
276
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95%
With hydrogenchloride
T=100°C; 16 h;
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Rx-ID: 8913859 Find similar reactions
Clerici, Francesca; Gelmi, Maria Luisa; Gambini, Andrea; Nava, Donatella
Tetrahedron, 2001 , vol. 57, # 30 p. 6429 - 6438 Title/Abstract Full Text View citing articles Show Details
277
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100%
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide in tetrahydrofuran
42 h; Heating;
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Rx-ID: 8930149 Find similar reactions
Giurg; Said; Syper; Mlochowski
Synthetic Communications, 2001 , vol. 31, # 20 p. 3151 - 3159 Title/Abstract Full Text View citing articles Show Details
278
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96%
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide in tetrahydrofuran
18 h; Heating;
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Rx-ID: 8941387 Find similar reactions
Giurg; Said; Syper; Mlochowski
Synthetic Communications, 2001 , vol. 31, # 20 p. 3151 - 3159 Title/Abstract Full Text View citing articles Show Details
279
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99%
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide in tetrahydrofuran
60 h; Heating;
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Rx-ID: 8961428 Find similar reactions
Giurg; Said; Syper; Mlochowski
Synthetic Communications, 2001 , vol. 31, # 20 p. 3151 - 3159 Title/Abstract Full Text View citing articles Show Details
280
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Multi-step reaction with 2 steps 1: 93 percent / conc. HCl / tetrahydrofuran / 1 h / 20 °C 2: 95 percent / aq. HCl / 16 h / 100 °C View Scheme
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Rx-ID: 15281902 Find similar reactions
Clerici, Francesca; Gelmi, Maria Luisa; Gambini, Andrea; Nava, Donatella
Tetrahedron, 2001 , vol. 57, # 30 p. 6429 - 6438 Title/Abstract Full Text View citing articles Show Details
281
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Multi-step reaction with 2 steps 1: 95 percent / sulfur / 0.07 h / microwave irradiation 2: 95 percent / aq. NaOH / 0.02 h / microwave irradiation View Scheme
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Rx-ID: 15507302 Find similar reactions
Matloubi Moghaddam; Ghaffarzadeh
Synthetic Communications, 2001 , vol. 31, # 2 p. 317 - 321 Title/Abstract Full Text View citing articles Show Details
282
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Rx-ID: 4900643 Find similar reactions
97%
With Montmorillonite K-10 clay; methoxybenzene
Dealkylation; 0.333333 h; Microwave irradiation;
Gajare, Anil S.; Shaikh, Nadim S.; Bonde, Bhushan K.; Deshpande, Vishnu H.
Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 5 p. 639 - 640 Title/Abstract Full Text View citing articles Show Details
10%
With methoxybenzene in toluene
15 h; Heating;
Gajare; Shingare; Kulkarni; Barhate; Wakharkar
Synthetic Communications, 1998 , vol. 28, # 1 p. 25 - 33 Title/Abstract Full Text View citing articles Show Details
A
B
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283
Synthesize Find similar Rx-ID: 8611231 Find similar reactions
With sulfuric acid; acetic acid; ruthenium trichloride
T=24.85 - 39.85°C; Catalytic oxidation; Kinetics;
Annapoorna; Prasad Rao; Sethuram
International Journal of Chemical Kinetics, 2000 , vol. 32, # 10 p. 581 - 588 Title/Abstract Full Text View citing articles Show Details
A
B
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Synthesize Find similar
284
Synthesize Find similar Rx-ID: 8619432 Find similar reactions
With sulfuric acid; acetic acid; ruthenium trichloride
T=24.85 - 39.85°C; Catalytic oxidation; Kinetics;
Annapoorna; Prasad Rao; Sethuram
International Journal of Chemical Kinetics, 2000 , vol. 32, # 10 p. 581 - 588 Title/Abstract Full Text View citing articles Show Details
A
B
Synthesize Find similar
Synthesize Find similar
285
Synthesize Find similar Rx-ID: 8619870 Find similar reactions
With sulfuric acid; acetic acid; ruthenium trichloride
T=24.85 - 39.85°C; Catalytic oxidation; Kinetics;
Annapoorna; Prasad Rao; Sethuram
International Journal of Chemical Kinetics, 2000 , vol. 32, # 10 p. 581 - 588 Title/Abstract Full Text View citing articles Show Details
A
B
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Synthesize Find similar
286
Synthesize Find similar Rx-ID: 8626944 Find similar reactions
With sulfuric acid; acetic acid; ruthenium trichloride
T=24.85 - 39.85°C; Catalytic oxidation; Kinetics;
Annapoorna; Prasad Rao; Sethuram
International Journal of Chemical Kinetics, 2000 , vol. 32, # 10 p. 581 - 588 Title/Abstract Full Text View citing articles Show Details
A
B
Synthesize Find similar
Synthesize Find similar
287
Synthesize Find similar Rx-ID: 8639070 Find similar reactions
With sulfuric acid; acetic acid; ruthenium trichloride
T=24.85 - 39.85°C; Catalytic oxidation; Kinetics;
Annapoorna; Prasad Rao; Sethuram
International Journal of Chemical Kinetics, 2000 , vol. 32, # 10 p. 581 - 588 Title/Abstract Full Text View citing articles Show Details
A
B
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Synthesize Find similar
288
Synthesize Find similar Rx-ID: 8736610 Find similar reactions
A: 80% B: 9%
With HOF* CH3CN in chloroform
T=0 - 20°C;
Dayan; Ben-David; Rozen
Journal of Organic Chemistry, 2000 , vol. 65, # 25 p. 8816 - 8818 Title/Abstract Full Text View citing articles Show Details
A
B
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289
Synthesize Find similar Rx-ID: 8838353 Find similar reactions
With water in acetonitrile
T=37°C; pH=2.0; 0.166667 h; Acid hydrolysis; Kinetics; Further Variations:pH-valuesreaction
Liu, Ding Y.; Liu, Zu D.; Lu, Shu L.; Hider, Robert C.
Pharmacology and Toxicology, 2000 , vol. 86, # 5 p. 228 - 233 Title/Abstract Full Text View citing articles Show Details
time;
A
B
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290
Synthesize Find similar Rx-ID: 5100043 Find similar reactions
A: 89%
With dihydrogen peroxide; methyltrioxorhenium (VII); acetic acid; sodium bromide in methanol
10 h; Ambient temperature;
Espenson; Zhu; Zauche
Journal of Organic Chemistry, 1999 , vol. 64, # 4 p. 1191 - 1196 Title/Abstract Full Text View citing articles Show Details
A
B
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291
Synthesize Find similar Rx-ID: 5120691 Find similar reactions
With sodium perchlorate; water in acetonitrile
T=25°C; also in base and acid buffers; Rate constant;
Lopes, Francisca; Moreira, Rui; Iley, Jim
Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 3 p. 431 - 439 Title/Abstract Full Text View citing articles Show Details
A
B
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292
Synthesize Find similar
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Rx-ID: 5136319 Find similar reactions
A: 47%
With RuIII-Montmorillonite K10 in acetonitrile
Nikalje, Milind D.; Sudalai
B: 29%
4 h; Heating;
Tetrahedron, 1999 , vol. 55, # 18 p. 5903 - 5908 Title/Abstract Full Text View citing articles Show Details
A
B
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Synthesize Find similar
293
Synthesize Find similar
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Rx-ID: 5192940 Find similar reactions
B: 67%
With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide
T=50°C; Carbonylation; 1 h;
Xia, Min; Chen, Zhen-Chu
Journal of Chemical Research - Part S, 1999 , # 5 p. 328 - 329 Title/Abstract Full Text View citing articles Show Details
A
B
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294
Synthesize Find similar
Synthesize Find similar
Rx-ID: 5192942 Find similar reactions
B: 64%
With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide
T=50°C; Carbonylation; 1 h;
Xia, Min; Chen, Zhen-Chu
Journal of Chemical Research - Part S, 1999 , # 5 p. 328 - 329 Title/Abstract Full Text View citing articles Show Details
A
B
C
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295
Synthesize Find similar Rx-ID: 5204838 Find similar reactions
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B: 53%
With BF3·2HOAc in hexane
Aldol-Grob reaction; 2.5 h; Heating;
Kabalka; Li; Tejedor; Malladi; Gao; Trotman
Synthetic Communications, 1999 , vol. 29, # 16 p. 2783 - 2787 Title/Abstract Full Text View citing articles Show Details
A
B
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Synthesize Find similar
296
Synthesize Find similar Rx-ID: 5267565 Find similar reactions
With disodium hydrogenphosphate; sodium acetate; permanganate(VII) ion
T=29.85°C; Oxidation; pH=6.5; Kinetics; Further Variations:TemperaturesReagents;
Sikkandar; Ahamed, K.A.Basheer; Kannan
Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry, 1999 , vol. 38, # 2 p. 183 - 186 Title/Abstract Full Text View citing articles Show Details
A
B
C
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297
Synthesize Find similar Rx-ID: 5287457 Find similar reactions
in methanol-d4
T=34.85°C; Rearrangement; KineticsActivation energy; Further Variations:Temperatures;
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Campbell, John J.; Glover, Stephen A.
Journal of Chemical Research, Miniprint, 1999 , # 8 p. 2075 - 2096 Title/Abstract Full Text Show Details