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Chemical Structure| 80-09-1
Chemical Structure| 80-09-1
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Product Details of [ 80-09-1 ]

CAS No. :80-09-1 MDL No. :MFCD00002350
Formula : C12H10O4S Boiling Point : -
Linear Structure Formula :- InChI Key :VPWNQTHUCYMVMZ-UHFFFAOYSA-N
M.W : 250.27 Pubchem ID :6626
Synonyms :

Calculated chemistry of [ 80-09-1 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 62.43
TPSA : 82.98 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.27
Log Po/w (XLOGP3) : 1.9
Log Po/w (WLOGP) : 3.01
Log Po/w (MLOGP) : 1.87
Log Po/w (SILICOS-IT) : 1.32
Consensus Log Po/w : 1.88

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.98
Solubility : 0.263 mg/ml ; 0.00105 mol/l
Class : Soluble
Log S (Ali) : -3.27
Solubility : 0.136 mg/ml ; 0.000543 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.69
Solubility : 0.0505 mg/ml ; 0.000202 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.88

Safety of [ 80-09-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 80-09-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 80-09-1 ]
  • Downstream synthetic route of [ 80-09-1 ]

[ 80-09-1 ] Synthesis Path-Upstream   1~53

  • 1
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  • [ 80-09-1 ]
  • [ 1698-60-8 ]
YieldReaction ConditionsOperation in experiment
92.3% With ammonia In water EXAMPLE 2
Preparation of 4-amino-5-chloro-1-phenylpyridazin-6-one (chloridazon) using bis(4-hydroxyphenyl) sulfone as catalyst
In a 1 l stirring autoclave, 300 parts of water, 210 parts (3.09 mol) of 25percent strength ammonia, 36 parts (0.15 mol) of 4,5-dichloro-1-phenylpyridazin-6-one (purity: 99.7percent) and 37.5 parts (0.15 mol) of bis(4-hydroxyphenyl)sulfone were stirred at 130° C. for 8 hours.
The pressure rose steadily to about 5 bar.
After stirring overnight, the autoclave was depressurized to atmospheric pressure, with the excess ammonia being stripped off.
After cooling to room temperature, the precipitated solid was filtered off, washed with water and dried at 50° C. in a vacuum drying oven.
This gave 30.7 parts of 4-amino-5-chloro-1-phenylpyridazin-6-one having a purity of 99.9percent; this corresponds to a yield of 92.3percent of theory.
The pH of the filtrate was adjusted to 1.4 using 60percent strength sulfuric acid and the precipitated bis(4-hydroxyphenyl)sulfone was filtered off and washed with water.
This gave 53.5 parts of bis(4-hydroxyphenyl)sulfone having a water content of 30percent.
This corresponds to 99.8percent of the amount of catalyst used.
90% With ammonia In water EXAMPLE 1
Preparation of 4-amino-5-chloro-1-phenylpyridazin-6-one (chloridazon) using bis(4-hydroxyphenyl)sulfone
In a 250 ml stirring autoclave, 100 parts of water, 70 parts (1.03 mol) of 25percent strength ammonia, 12 parts (0.05 mol) of 4,5-dichloro-1-phenylpyridazin-6-one (purity: 99.7percent) and 12.5 parts (0.05 mol) of bis(4-hydroxyphenyl)sulfone were stirred at 130° C. for 8 hours.
The pressure rose steadily to about 5 bar.
After stirring overnight, the autoclave was depressurized to atmospheric pressure, with the excess ammonia being stripped off.
After cooling to room temperature, the precipitated solid was filtered off, washed with water and dried at 50° C. in a vacuum drying oven.
This gave 10.1 parts of 4-amino-5-chloro-1-phenylpyridazin-6-one having a purity of 98.8percent; this corresponds to a yield of 90percent of theory.
The pH of the filtrate was adjusted to 1.5 using 60percent strength sulfuric acid and the precipitated bis(4-hydroxyphenyl)sulfone was filtered off, washed with water and dried.
This gave 12.6 parts of bis(4-hydroxyphenyl)sulfone having a purity of 99.2percent; this corresponds to 100percent of the amount of catalyst used.
Reference: [1] Patent: US6538135, 2003, B1,
[2] Patent: US6538135, 2003, B1,
  • 2
  • [ 1698-53-9 ]
  • [ 80-09-1 ]
  • [ 1698-60-8 ]
Reference: [1] Patent: US6538135, 2003, B1,
  • 3
  • [ 80-09-1 ]
  • [ 383-29-9 ]
Reference: [1] Patent: US6242654, 2001, B1,
[2] Organic Letters, 2013, vol. 15, # 21, p. 5602 - 5605
  • 4
  • [ 108-95-2 ]
  • [ 80-09-1 ]
  • [ 5397-34-2 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With sulfuric acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5 h; Heating / reflux
Stage #2: at 170 - 185℃; for 2 h;
One hundred grams (1.0 mol) of 98percent sulfuric acid was added dropwise to a mixture of 144 g of mesitylene, 189 g (2.0 mol) of phenol and 11.9 g (0.05 mol) of benzene-1,3-disulfonic acid while stirring. The reaction solution was heated in a 200° C. oil bath. The reaction solution started boiling at a temperature near 145° C. Distillates were condensed by a condenser and separated into 2 phases by a trap. The upper phase, i.e., the organic phase, was continuously returned to the reaction system. Five hours after the beginning of distillation, the temperature of the reaction solution was 165° C., and the amount of water in the lower phase separated by the trap was steady at 38 ml. Crystals were precipitated in the reaction system, thereby forming a slurry. A small amount of the reaction slurry was sampled and analyzed by HPLC. The result showed a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=96.0/3.0/1.0. Thereafter, aftertreatment was conducted in the same manner as in Example 1, thereby giving 237 g of crystals. The crystals thus obtained had a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=99.5/0.5/0. The yield of 4,4'-BS based on the starting sulfuric acid was 94percent. Sulfonic acids, chiefly benzene-1,3-disulfonic acid and phenolsulfonic acid, were not detected in the crystals.
89% With sulfuric acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5 h; Heating / reflux A dehydration reaction was carried out in the same manner as in Example 1. The reaction suspension without any addition of phenol was cooled to 40° C., and the precipitated crystals were filtered off, washed and dried, thereby giving 245 g of crystals. The crystals had a 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone composition (weight ratio) of 92.5/6.0/1.5. The crystals also contained sulfonic acids, chiefly phenolsulfonic acid, in a proportion of 2percent. The yield of 4,4'-BS based on the starting sulfuric acid was 89percent.
83%
Stage #1: With sulfuric acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5 h; Heating / reflux
Stage #2: at 170 - 185℃; for 2 h;
One hundred grams (1.0 mol) of 98percent sulfuric acid was added dropwise to a mixture of 144 g of mesitylene and 189 g (2.0 mol) of phenol while stirring. The reaction solution was heated in a 200° C. oil bath for dehydration. The reaction solution started boiling at a temperature near 145° C. Distillates were condensed by a condenser and separated into 2 phases by a trap. The upper phase, i.e., the organic phase, was continuously returned to the reaction system. Five hours after the beginning of distillation, the temperature of the reaction solution was 165° C., and the amount of water in the lower phase separated by the trap was steady at 38 ml. Crystals were precipitated in the reaction system, thereby forming a slurry. A small amount of the resulting reaction suspension was sampled and analyzed by HPLC. The result showed a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=92.5/6.0/1.5. Phenol in an amount of 189 g was added to the reaction suspension and heated hermetically. When the temperature reached 185° C., the crystals were completely dissolved. The pressure in the reaction system at this point was 0.07 MPa. The solution was then cooled while stirring. Crystals started precipitating at 165° C. The solution was further cooled to 40° C., and the precipitated crystals were filtered off, washed and dried, thereby giving 208 g of crystals. The crystals thus obtained had a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=99.5/0.5/0. The yield of 4,4'-BS based on the starting sulfuric acid was 83percent. Phenolsulfonic acid and like sulfonic acids were not detected in the crystals.; A dehydration reaction was carried out in the same manner as in Example 1. After the reaction, 189 g of phenol was added to the reaction suspension. The mixture was heated to about 180° C. Although most crystals were dissolved, some crystals were present as a suspension (slurry), and then precipitation by cooling and aftertreatment were conducted in the same manner as in Example 1, thereby giving 208 g of crystals. The crystals thus obtained had a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=99.2/0.8/0. The yield of 4,4'-BS based on the starting sulfuric acid was 83percent. Phenolsulfonic acid and like sulfonic acids were not detected in the crystals.; The filtrate after filtering off the primary crystals of Example 1 (4,4'-BS/2,4'-BS=48:52 in the filtrate) was heated to 165° C. The solvents contained therein were recovered by distillation under reduced pressure until the solvent distillation terminated. The temperature was maintained at 170° C. for 2 hours to substantially complete the isomerization reaction from 2,4'-BS to 4,4'-BS, thereby giving a distillation residue. This distillation residue was mixed with 48 g of phenol and 36 g of mesitylene, and the mixture was heated for complete dissolution and then cooled to 40° C., thereby precipitating crystals. The crystals thus obtained were filtered off, washed and dried, thereby giving 28 g of secondary crystals. These secondary crystals had a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=99.1/0.6/0.3. The yield of 4,4'-BS based on the starting sulfuric acid in Example 1 was 11percent. The procedures described in Example 1 were repeated except that all of the secondary crystals obtained above were introduced into the reaction system after the dehydration reaction, thereby giving 237 g of crystals. The crystals thus obtained had a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=99.5/0.5/0. The yield of 4,4'-BS based on the starting sulfuric acid was 94percent. Phenolsulfonic acid and like sulfonic acids were not detected in the crystals.
81%
Stage #1: With sulfuric acid In 3,4-Dichlorotoluene at 145 - 165℃; for 5 h; Heating / reflux
Stage #2: at 170 - 185℃; for 2 h;
A dehydration reaction was carried out in the same manner as in Example 1 except for using 208 g of 3,4-dichlorotoluene in place of mesitylene, thereby giving a reaction suspension. A small amount of the reaction suspension was sampled and analyzed by HPLC. The result showed a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=91.5/7.0/1.5. Crystals present in the reaction suspension were completely dissolved in the same manner as in Example 1. The solution was then cooled, thereby giving 203 g of crystals. The crystals thus obtained had a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=99.3/0.7/0. The yield of 4,4'-BS based on the starting sulfuric acid was 81percent. Phenolsulfonic acid and like sulfonic acids were not detected in the crystals
80%
Stage #1: With sulfuric acid In 1,2,4-Trichlorobenzene at 145 - 165℃; for 5 h; Heating / reflux
Stage #2: at 170 - 185℃; for 2 h;
A dehydration reaction was carried out in the same manner as in Example 1 except for using 240 g of 1,2,4-trichlorobenzene in place of mesitylene, thereby giving a reaction suspension. A small amount of the reaction suspension was sampled and analyzed by HPLC. The result showed a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=90.7/7.6/1.7. Crystals present in the reaction suspension were completely dissolved in the same manner as in Example 1 except that, instead of phenol, 190 g of cresol was added to the reaction suspension. The solution was then cooled, thereby giving 200 g of crystals. The crystals thus obtained had a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=99.4/0.6/0. The yield of 4,4'-BS based on the starting sulfuric acid was 80percent. Phenolsulfonic acid and like sulfonic acids were not detected from the crystals.

Reference: [1] Patent: US2005/272956, 2005, A1, . Location in patent: Page/Page column 5-6
[2] Patent: US2005/272956, 2005, A1, . Location in patent: Page/Page column 6
[3] Patent: US2005/272956, 2005, A1, . Location in patent: Page/Page column 5
[4] Russian Journal of Applied Chemistry, 2006, vol. 79, # 3, p. 425 - 429
[5] Patent: US2005/272956, 2005, A1, . Location in patent: Page/Page column 6
[6] Patent: US2005/272956, 2005, A1, . Location in patent: Page/Page column 6
[7] Journal fuer Praktische Chemie (Leipzig), 1942, vol. <2> 160, p. 41,63
[8] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
[9] Journal of the Chemical Society, 1949, p. 2854,2856
[10] Journal fuer Praktische Chemie (Leipzig), 1942, vol. <2> 160, p. 41,63
[11] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
[12] Journal of the Chemical Society, 1949, p. 2854,2856
[13] Journal fuer Praktische Chemie (Leipzig), 1942, vol. <2> 160, p. 41,63
[14] Patent: EP1468987, 2004, A1, . Location in patent: Page 5
[15] Patent: EP1491528, 2004, A1, . Location in patent: Page column 16
[16] Patent: EP1491528, 2004, A1, . Location in patent: Page column 16-18
[17] Patent: EP1491528, 2004, A1, . Location in patent: Page column 18
[18] Asian Journal of Chemistry, 2014, vol. 26, # 22, p. 7759 - 7762
  • 5
  • [ 2664-63-3 ]
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YieldReaction ConditionsOperation in experiment
94% With dihydrogen peroxide In water at 20℃; for 0.833333 h; General procedure: To a mixture of sulfide (1 mmol) and catalyst (0.04 g), H2O2 30percent(v/v) (0.28 g, 2.5 equiv.) was added and stirred at room temperature for a specified time. After completion of the reaction, as indicated on thin-layer chromatography (TLC), ethyl acetate (20 mL) was added and the mixture was centrifuged to separate the catalyst. The filtrate was washed with brine and dried over anhydrous Na2SO4. Purification of the combined organics by preparative TLC (hexane-ethyl acetate, 10:1) provided pure products. The recycled catalyst was washed with ethyl acetate and acetone. After being dried at 60 °C, it can be reused without further purification. All of the products were known and identified by comparison of their melting points and spectral data with those reported in the literature 2.4.
Reference: [1] Journal of the Chilean Chemical Society, 2018, vol. 63, # 1, p. 3829 - 3833
[2] RSC Advances, 2014, vol. 4, # 76, p. 40505 - 40510
[3] Monatshefte fur Chemie, 2007, vol. 138, # 7, p. 649 - 651
[4] Gazzetta Chimica Italiana, 1890, vol. 20, p. 362
[5] Gazzetta Chimica Italiana, 1890, vol. 20, p. 362
[6] Journal of the Iranian Chemical Society, 2012, vol. 9, # 3, p. 349 - 355
[7] Journal of the Iranian Chemical Society, 2017, vol. 14, # 5, p. 963 - 975
  • 6
  • [ 108-95-2 ]
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YieldReaction ConditionsOperation in experiment
80% With sulfuric acid In ISOPER G at 50 - 165℃; for 7 h; water separating duct In a four-necked flask (500 ml) provided with a stirrer, a thermometer, and water separating duct, 131.6 g (1.4 mole) of phenol and 70 ml of ISOPER G were introduced, and 72.2 g (0.7 mole) of 95percent sulfuric acid was added dropwise to the mixture with stirring at 50°C. After the completion of dropwise addition, the temperature of the reaction system was gradually increased while stirring the reaction mixture. Distillation of the reaction solution was started at about 144°C, and the distillate was condensed and separated in three layers including a solvent upper layer, an aqueous middle layer, and a phenol lower layer using the water separating duct. The solvent upper layer was continuously returned to the reaction system, and the phenol lower layer was extracted every 15 minutes and returned to the reaction system. The temperature of the reaction system reached 165°C after about seven hours from the start of increasing the temperature, and the generation of water stopped. Nearly all water and unreacted phenol were evaporated from the reaction solution. Then, the reaction mixture was cooled to 80°C, and 185 ml of methanol was added. The solution was stirred at 65°C for one hour. Then, 144 ml of water was added for separating layers, and an alcoholic aqueous layer was obtained. After this, 10percent sodium hydroxide aqueous solution was added to adjust pH to 5, and then 1 ml of 5percent aqueous solution of sodium EDTA2 was added dropwise. After sufficiently stirring the alcoholic aqueous layer, the solution was cooled to 30°C for precipitation. Precipitated crystals were filtered and dried to obtain 140.2 g (yield: 80percent) of a targeted product of 4,4'-dihydroxydiphenyl sulfone powder. Purity of the obtained 4,4'-dihydroxydiphenyl sulfone was 99.5percent or higher. The b value of the product measured by a color-difference meter (type: 1001DP, a product of Nippon Denshoku Co., Ltd.) was 2.5 or less, and no coloration was observed.
Reference: [1] Patent: EP1491528, 2004, A1, . Location in patent: Page column 18-19
[2] Patent: US2000061, 1933, ,
[3] Patent: US2122958, 1936, ,
[4] Patent: FR810090, 1936, ,
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 24, p. 1205
[6] Journal fuer Praktische Chemie (Leipzig), 1927, vol. <2> 117, p. 242 Anm. 2
[7] Bulletin de la Societe Chimique de France, 1923, vol. <4> 33, p. 183
[8] Justus Liebigs Annalen der Chemie, 1868, vol. 147, p. 52
[9] Justus Liebigs Annalen der Chemie, 1874, vol. 172, p. 33 Anm.
[10] Journal of the Chemical Society, 1907, vol. 91, p. 1119
[11] Patent: US4820831, 1989, A,
[12] Patent: CN104557637, 2017, B, . Location in patent: Paragraph 0024-0027; 0028-0031; 0032-0035
[13] Patent: US2000061, 1933, ,
  • 7
  • [ 95-50-1 ]
  • [ 108-95-2 ]
  • [ 80-09-1 ]
YieldReaction ConditionsOperation in experiment
90% With sulfuric acid In chlorobenzene EXAMPLE 2
385 g (4.1 moles) of phenol, 150 ml of chlorobenzene and 60 ml of o-dichlorobenzene were introduced under nitrogen into a 2 liter ground-flange vessel arranged in a circuit with a scraper cooler, and were refluxed. 209 g (2.05 moles) of 96percent strength by weight sulfuric acid were added dropwise over 2 hours.
Throughout the reaction time, water was removed from the system and the organic phase was recycled to the reaction vessel.
The entire reaction solution (at 168° C.) was then pumped, in a closed heated system, over the scraper cooler (at 100° C.) and back into the reaction vessel.
The product which deposited on the supercooled cooler was scraped off continuously and removed After a reaction time of 3 hours, bis(4-hydroxyphenyl)sulfone was obtained in a purity of >99.5percent (HPLC) and in 90percent yield.
To effect further purification, the procedure described in Example 1 may be followed.
Reference: [1] Patent: US5059715, 1991, A,
[2] Patent: US4162270, 1979, A,
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YieldReaction ConditionsOperation in experiment
92.6% With sodium hydroxide; sulfuric acid In water EXAMPLE 4
A mixture of 343 g (3.69 moles) of phenol, 146 g (1.46 moles) of 98percent sulfuric acid and 300 g of o-dichlorobenzene is heated with stirring.
When the temperature of the reaction system reaches about 140° C., the mixture begins to boil, giving off an azeotropic mixture of water and o-dichlorobenzene, which is condensed and separated into two phases, i.e., water and o-dichlorobenzene.
The o-dichlorobenzene is continuously returned to the reaction mixture.
With continuous heating, when the amount of the aqueous phase reaches 55 ml, the temperature of reaction mixture is about 184° C.
Subsequently o-dichlorobenzene containing small amounts of water and phenol is completely distilled off over a period of 3 hours by reducing a pressure of the reaction system to produce the dried reaction mixture in a solid state, while adjusting the temperature to 180° to 190° C.
A solution of 62 g of sodium hydroxide in 3.5 l of water is added to the residue, 5 g of active carbon is added to the solution, the mixture is filtered and the filtrate is neutralized with sulfuric acid.
The resulting crystals are filtered off, then washed with water and dried, giving 338 g of 4,4'-dihydroxydiphenylsulfone, melting at 248.5° C., in a yield of 92.6percent based on the sulfuric acid starting material.
When analyzed by gas chromatography, the isomer content is found to be 0.6percent in the dried reaction mixture and 0.5percent in the product.
Reference: [1] Patent: US4162270, 1979, A,
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Reference: [1] ACS Catalysis, 2013, vol. 3, # 7, p. 1657 - 1664
[2] Journal of the Iranian Chemical Society, 2017, vol. 14, # 5, p. 963 - 975
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  • [ 1698-60-8 ]
Reference: [1] Patent: US6538135, 2003, B1,
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  • [ 5397-34-2 ]
Reference: [1] Patent: US9434199, 2016, B2, . Location in patent: Page/Page column 18
  • 12
  • [ 80-07-9 ]
  • [ 7402-67-7 ]
  • [ 80-09-1 ]
Reference: [1] Chemical Communications, 1997, # 6, p. 567 - 568
  • 13
  • [ 609-46-1 ]
  • [ 80-09-1 ]
Reference: [1] Patent: US8956423, 2015, B2, . Location in patent: Page/Page column
  • 14
  • [ 98-48-6 ]
  • [ 108-95-2 ]
  • [ 80-09-1 ]
Reference: [1] Patent: US4820831, 1989, A,
  • 15
  • [ 80-07-9 ]
  • [ 38980-51-7 ]
  • [ 80-09-1 ]
  • [ 5397-34-2 ]
Reference: [1] Patent: WO2011/67649, 2011, A2, . Location in patent: Page/Page column 36
  • 16
  • [ 108-95-2 ]
  • [ 80-09-1 ]
  • [ 5397-34-2 ]
Reference: [1] Patent: EP1491528, 2004, A1, . Location in patent: Page column 15
[2] Patent: EP1491528, 2004, A1, . Location in patent: Page column 15-16
  • 17
  • [ 108-95-2 ]
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  • [ 5397-34-2 ]
Reference: [1] Patent: US4125562, 1978, A,
  • 18
  • [ 98-48-6 ]
  • [ 80-09-1 ]
Reference: [1] Patent: US4820831, 1989, A,
[2] Patent: US4820831, 1989, A,
  • 19
  • [ 80-07-9 ]
  • [ 80-09-1 ]
Reference: [1] Patent: US2288282, 1941, ,
[2] DRP/DRBP Org.Chem.,
[3] DRP/DRBP Org.Chem.,
  • 20
  • [ 3112-80-9 ]
  • [ 80-09-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1942, vol. <2> 160, p. 41,63
[2] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
  • 21
  • [ 66294-58-4 ]
  • [ 80-09-1 ]
Reference: [1] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
  • 22
  • [ 69-72-7 ]
  • [ 80-09-1 ]
Reference: [1] Roczniki Chemii, 1953, vol. 27, p. 348,359[2] Chem.Abstr., 1955, p. 918
  • 23
  • [ 98-67-9 ]
  • [ 108-95-2 ]
  • [ 80-09-1 ]
Reference: [1] Zhurnal Obshchei Khimii, 1958, vol. 28, p. 1274; engl. Ausg. S. 1330
  • 24
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  • [ 80-09-1 ]
Reference: [1] Journal of the Chemical Society, 1907, vol. 91, p. 1119
[2] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
[3] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
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Reference: [1] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
[2] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
[3] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
[4] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
  • 26
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Reference: [1] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
[2] Gazzetta Chimica Italiana, 1887, vol. 17, p. 91[3] Gazzetta Chimica Italiana, 1893, vol. 23 I, p. 194
  • 27
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  • [ 80-09-1 ]
Reference: [1] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
[2] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
[3] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
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Reference: [1] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
[2] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
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  • [ 80-09-1 ]
Reference: [1] Roczniki Chemii, 1953, vol. 27, p. 348,359[2] Chem.Abstr., 1955, p. 918
[3] Roczniki Chemii, 1953, vol. 27, p. 348,359[4] Chem.Abstr., 1955, p. 918
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Reference: [1] Roczniki Chemii, 1953, vol. 27, p. 348,359[2] Chem.Abstr., 1955, p. 918
  • 31
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Reference: [1] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
  • 32
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  • [ 80-09-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1923, vol. 433, p. 342
  • 33
  • [ 98-67-9 ]
  • [ 108-38-3 ]
  • [ 80-09-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1923, vol. 433, p. 342
  • 34
  • [ 609-46-1 ]
  • [ 108-38-3 ]
  • [ 80-09-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1923, vol. 433, p. 342
  • 35
  • [ 98-67-9 ]
  • [ 108-88-3 ]
  • [ 80-09-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1923, vol. 433, p. 342
  • 36
  • [ 609-46-1 ]
  • [ 108-88-3 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1923, vol. 433, p. 342
  • 37
  • [ 98-67-9 ]
  • [ 71-43-2 ]
  • [ 80-09-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1923, vol. 433, p. 342
  • 38
  • [ 609-46-1 ]
  • [ 71-43-2 ]
  • [ 80-09-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1923, vol. 433, p. 342
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  • [ 108-95-2 ]
  • [ 80-09-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1927, vol. <2> 117, p. 21
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  • [ 80-08-0 ]
  • [ 80-09-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1923, vol. 433, p. 342
  • 41
  • [ 14052-63-2 ]
  • [ 80-09-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1923, vol. 433, p. 342
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Reference: [1] Zhurnal Obshchei Khimii, 1949, vol. 19, p. 1943,1948[2] Chem.Abstr., 1950, p. 1922
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Reference: [1] Journal of the Chemical Society, 1949, p. 2854,2856
[2] Journal fuer Praktische Chemie (Leipzig), 1961, vol. <4> 13, p. 39,40, 43
  • 44
  • [ 609-46-1 ]
  • [ 108-88-3 ]
  • [ 599-66-6 ]
  • [ 80-09-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1923, vol. 433, p. 342
  • 45
  • [ 7664-93-9 ]
  • [ 7446-11-9 ]
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1942, vol. <2> 160, p. 41,63
  • 46
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  • [ 7545-50-8 ]
Reference: [1] Roczniki Chemii, 1953, vol. 27, p. 348,359[2] Chem.Abstr., 1955, p. 918
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  • [ 80-09-1 ]
  • [ 5397-34-2 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With sulfuric acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5 h; Heating / reflux
Stage #2: at 170 - 185℃; for 2 h;
One hundred grams (1.0 mol) of 98percent sulfuric acid was added dropwise to a mixture of 144 g of mesitylene, 189 g (2.0 mol) of phenol and 11.9 g (0.05 mol) of benzene-1,3-disulfonic acid while stirring. The reaction solution was heated in a 200° C. oil bath. The reaction solution started boiling at a temperature near 145° C. Distillates were condensed by a condenser and separated into 2 phases by a trap. The upper phase, i.e., the organic phase, was continuously returned to the reaction system. Five hours after the beginning of distillation, the temperature of the reaction solution was 165° C., and the amount of water in the lower phase separated by the trap was steady at 38 ml. Crystals were precipitated in the reaction system, thereby forming a slurry. A small amount of the reaction slurry was sampled and analyzed by HPLC. The result showed a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=96.0/3.0/1.0. Thereafter, aftertreatment was conducted in the same manner as in Example 1, thereby giving 237 g of crystals. The crystals thus obtained had a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=99.5/0.5/0. The yield of 4,4'-BS based on the starting sulfuric acid was 94percent. Sulfonic acids, chiefly benzene-1,3-disulfonic acid and phenolsulfonic acid, were not detected in the crystals.
89% With sulfuric acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5 h; Heating / reflux A dehydration reaction was carried out in the same manner as in Example 1. The reaction suspension without any addition of phenol was cooled to 40° C., and the precipitated crystals were filtered off, washed and dried, thereby giving 245 g of crystals. The crystals had a 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone composition (weight ratio) of 92.5/6.0/1.5. The crystals also contained sulfonic acids, chiefly phenolsulfonic acid, in a proportion of 2percent. The yield of 4,4'-BS based on the starting sulfuric acid was 89percent.
83%
Stage #1: With sulfuric acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5 h; Heating / reflux
Stage #2: at 170 - 185℃; for 2 h;
One hundred grams (1.0 mol) of 98percent sulfuric acid was added dropwise to a mixture of 144 g of mesitylene and 189 g (2.0 mol) of phenol while stirring. The reaction solution was heated in a 200° C. oil bath for dehydration. The reaction solution started boiling at a temperature near 145° C. Distillates were condensed by a condenser and separated into 2 phases by a trap. The upper phase, i.e., the organic phase, was continuously returned to the reaction system. Five hours after the beginning of distillation, the temperature of the reaction solution was 165° C., and the amount of water in the lower phase separated by the trap was steady at 38 ml. Crystals were precipitated in the reaction system, thereby forming a slurry. A small amount of the resulting reaction suspension was sampled and analyzed by HPLC. The result showed a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=92.5/6.0/1.5. Phenol in an amount of 189 g was added to the reaction suspension and heated hermetically. When the temperature reached 185° C., the crystals were completely dissolved. The pressure in the reaction system at this point was 0.07 MPa. The solution was then cooled while stirring. Crystals started precipitating at 165° C. The solution was further cooled to 40° C., and the precipitated crystals were filtered off, washed and dried, thereby giving 208 g of crystals. The crystals thus obtained had a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=99.5/0.5/0. The yield of 4,4'-BS based on the starting sulfuric acid was 83percent. Phenolsulfonic acid and like sulfonic acids were not detected in the crystals.; A dehydration reaction was carried out in the same manner as in Example 1. After the reaction, 189 g of phenol was added to the reaction suspension. The mixture was heated to about 180° C. Although most crystals were dissolved, some crystals were present as a suspension (slurry), and then precipitation by cooling and aftertreatment were conducted in the same manner as in Example 1, thereby giving 208 g of crystals. The crystals thus obtained had a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=99.2/0.8/0. The yield of 4,4'-BS based on the starting sulfuric acid was 83percent. Phenolsulfonic acid and like sulfonic acids were not detected in the crystals.; The filtrate after filtering off the primary crystals of Example 1 (4,4'-BS/2,4'-BS=48:52 in the filtrate) was heated to 165° C. The solvents contained therein were recovered by distillation under reduced pressure until the solvent distillation terminated. The temperature was maintained at 170° C. for 2 hours to substantially complete the isomerization reaction from 2,4'-BS to 4,4'-BS, thereby giving a distillation residue. This distillation residue was mixed with 48 g of phenol and 36 g of mesitylene, and the mixture was heated for complete dissolution and then cooled to 40° C., thereby precipitating crystals. The crystals thus obtained were filtered off, washed and dried, thereby giving 28 g of secondary crystals. These secondary crystals had a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=99.1/0.6/0.3. The yield of 4,4'-BS based on the starting sulfuric acid in Example 1 was 11percent. The procedures described in Example 1 were repeated except that all of the secondary crystals obtained above were introduced into the reaction system after the dehydration reaction, thereby giving 237 g of crystals. The crystals thus obtained had a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=99.5/0.5/0. The yield of 4,4'-BS based on the starting sulfuric acid was 94percent. Phenolsulfonic acid and like sulfonic acids were not detected in the crystals.
81%
Stage #1: With sulfuric acid In 3,4-Dichlorotoluene at 145 - 165℃; for 5 h; Heating / reflux
Stage #2: at 170 - 185℃; for 2 h;
A dehydration reaction was carried out in the same manner as in Example 1 except for using 208 g of 3,4-dichlorotoluene in place of mesitylene, thereby giving a reaction suspension. A small amount of the reaction suspension was sampled and analyzed by HPLC. The result showed a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=91.5/7.0/1.5. Crystals present in the reaction suspension were completely dissolved in the same manner as in Example 1. The solution was then cooled, thereby giving 203 g of crystals. The crystals thus obtained had a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=99.3/0.7/0. The yield of 4,4'-BS based on the starting sulfuric acid was 81percent. Phenolsulfonic acid and like sulfonic acids were not detected in the crystals
80%
Stage #1: With sulfuric acid In 1,2,4-Trichlorobenzene at 145 - 165℃; for 5 h; Heating / reflux
Stage #2: at 170 - 185℃; for 2 h;
A dehydration reaction was carried out in the same manner as in Example 1 except for using 240 g of 1,2,4-trichlorobenzene in place of mesitylene, thereby giving a reaction suspension. A small amount of the reaction suspension was sampled and analyzed by HPLC. The result showed a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=90.7/7.6/1.7. Crystals present in the reaction suspension were completely dissolved in the same manner as in Example 1 except that, instead of phenol, 190 g of cresol was added to the reaction suspension. The solution was then cooled, thereby giving 200 g of crystals. The crystals thus obtained had a composition (weight ratio) of 4,4'-BS/2,4'-BS/trihydroxytriphenyldisulfone=99.4/0.6/0. The yield of 4,4'-BS based on the starting sulfuric acid was 80percent. Phenolsulfonic acid and like sulfonic acids were not detected from the crystals.

Reference: [1] Patent: US2005/272956, 2005, A1, . Location in patent: Page/Page column 5-6
[2] Patent: US2005/272956, 2005, A1, . Location in patent: Page/Page column 6
[3] Patent: US2005/272956, 2005, A1, . Location in patent: Page/Page column 5
[4] Russian Journal of Applied Chemistry, 2006, vol. 79, # 3, p. 425 - 429
[5] Patent: US2005/272956, 2005, A1, . Location in patent: Page/Page column 6
[6] Patent: US2005/272956, 2005, A1, . Location in patent: Page/Page column 6
[7] Journal fuer Praktische Chemie (Leipzig), 1942, vol. <2> 160, p. 41,63
[8] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
[9] Journal of the Chemical Society, 1949, p. 2854,2856
[10] Journal fuer Praktische Chemie (Leipzig), 1942, vol. <2> 160, p. 41,63
[11] Journal of the Chinese Chemical Society (Peking), 1947, vol. 15, p. 129,132
[12] Journal of the Chemical Society, 1949, p. 2854,2856
[13] Journal fuer Praktische Chemie (Leipzig), 1942, vol. <2> 160, p. 41,63
[14] Patent: EP1468987, 2004, A1, . Location in patent: Page 5
[15] Patent: EP1491528, 2004, A1, . Location in patent: Page column 16
[16] Patent: EP1491528, 2004, A1, . Location in patent: Page column 16-18
[17] Patent: EP1491528, 2004, A1, . Location in patent: Page column 18
[18] Asian Journal of Chemistry, 2014, vol. 26, # 22, p. 7759 - 7762
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  • [ 108-90-7 ]
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  • [ 5397-34-2 ]
Reference: [1] Patent: US9434199, 2016, B2, . Location in patent: Page/Page column 18
  • 49
  • [ 80-07-9 ]
  • [ 38980-51-7 ]
  • [ 80-09-1 ]
  • [ 5397-34-2 ]
Reference: [1] Patent: WO2011/67649, 2011, A2, . Location in patent: Page/Page column 36
  • 50
  • [ 108-95-2 ]
  • [ 80-09-1 ]
  • [ 5397-34-2 ]
Reference: [1] Patent: EP1491528, 2004, A1, . Location in patent: Page column 15
[2] Patent: EP1491528, 2004, A1, . Location in patent: Page column 15-16
  • 51
  • [ 108-95-2 ]
  • [ 80-09-1 ]
  • [ 5397-34-2 ]
Reference: [1] Patent: US4125562, 1978, A,
  • 52
  • [ 7664-93-9 ]
  • [ 108-95-2 ]
  • [ 80-09-1 ]
  • [ 5397-34-2 ]
Reference: [1] Journal of the Chemical Society, 1949, p. 2854,2856
[2] Journal fuer Praktische Chemie (Leipzig), 1961, vol. <4> 13, p. 39,40, 43
  • 53
  • [ 7664-93-9 ]
  • [ 7446-11-9 ]
  • [ 108-95-2 ]
  • [ 80-09-1 ]
  • [ 5397-34-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1942, vol. <2> 160, p. 41,63
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