Phenol → Bisphenol S

HRID 971972

반응식

HRID 971972 반응식
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.C1C=C(O)C([S:20]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=CC=1.[OH-].[Na+]>O.ClC1C=CC=CC=1Cl>[CH:6]1[C:1]([OH:7])=[CH:2][CH:3]=[C:4]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:5]=1

참가 물질

7

반응물 4

HCID 996PhenolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 793812,4'-Dihydroxydiphenyl sulfone

생성물 1

HCID 6626Bisphenol S수율 91.2%

시약·촉매·용매 2

HCID 962Water용매2회HCID 72391,2-Dichlorobenzene용매2회

실험 절차

A mixture of 290 g (3.09 moles) of phenol, 146 g of 98% sulfuric acid and 150 g of o-dichlorobenzene is heated with stirring. When the temperature of the reaction system reaches about 150° 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 52 ml, the temperature of reaction mixture is about 180° 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 175° to 185° C. When analyzed by gas chromatography, the dried reaction mixture is found to contain 0.9% by weight of 2,4'-dihydroxydiphenylsulfone based on 4,4'-dihydroxydiphenylsulfone present therein (hereinafter referred to as isomer content). 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 332 g of 4,4'-dihydroxydiphenylsulfone, melting at 248° C., in a yield of 91.2% based on the sulfuric acid starting material. When analyzed by gas chromatography, the product is found to contain 0.8% of isomer content.

후처리

  1. temperatureis heated
  2. customreaches about 150° C.
  3. customgiving off
  4. customcondensed
  5. customseparated into two phases, i.e., water and o-dichlorobenzene
  6. customthe temperature of reaction mixture
  7. customis about 180° C
  8. distillationSubsequently o-dichlorobenzene containing small amounts of water and phenol is completely distilled off over a period of 3 hours
  9. customto produce
  10. customthe dried reaction mixture in a solid state
  11. customto 175° to 185° C
  12. customthe dried reaction mixture
  13. additionis added to the solution
  14. filtrationthe mixture is filtered
  15. filtrationThe resulting crystals are filtered off
  16. washwashed with water
  17. customdried

출처 및 근거

ORD 기록
ord-81a318f41e504ba293912ad20a74cdf8
출처 데이터셋
uspto-grants-1979_07
특허 번호
US04162270

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