Hydroquinone → Ethylene Oxide

HRID 1780226Notes

Reaction equation

[C:1]([OH:5])(=O)[CH:2]=C.S(=O)(=O)(O)O.[C:11]1([CH:18]=[CH:17][C:15]([OH:16])=[CH:14][CH:13]=1)O.[C:19]1(C)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:19]1([C:17]2[CH:18]=[CH:11][CH:13]=[CH:14][C:15]=2[OH:16])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:1]1[O:5][CH2:2]1

Participants

Reactant 4

HCID 785Hydroquinone

HCID 1118Sulfuric Acid

HCID 1140Toluene

HCID 6581Acrylic Acid

Product 2

HCID 6354Ethylene Oxide

HCID 7017(1,1'-Biphenyl)-2-ol

Procedure

258 parts of a compound represented by formula (6) ##STR8## (produced by Sanyo Chemical Industries, Ltd., reaction product of 1 mol of o-phenylphenol and 2 mol of ethylene oxide, trade name: Newpol OPE-20, OH value 217.5), 86.5 parts of acrylic acid, 300 parts of toluene, 21 parts of sulfuric acid and 5 parts of hydroquinone were charged and the mixture was heated. The produced water was distilled out together with the solvent, condensed and collected in a separator. When 18 parts of water was collected at the separator, the reaction mixture was cooled. The reaction temperature was 130°-40° C. The reaction mixture was solved in 500 parts of toluene, neutralized by 20% NaOH aqueous solution, and washed three times with 100 parts of 20% NaCl aqueous solution. By distilling off the solvent under reduced pressure, 303 parts of and acrylate represented by formula (7) was obtained. ##STR9##

Sources & evidence

ORD record: ord-d5ce6af3a265449ea242a6e990d1a9a2
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05629445

Reaction notes

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