Preparation of ortho-(alkyl- or arylthio)phenols
AssigneeE. I. Du Pont de Nemours and Company
InventorPaul W. Wojtkowski
Life of this patent
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Abstract
Strong acids, e.g., aluminosilicates and sulfonic acids are employed as catalysts for the (alkyl or aryl)thiolation of phenols using dialkyl or diaryl disulfides and/or (alkyl- or arylthio)phenols as thiolating agents, and for the isomerization of (alkyl- or arylthio)phenols, to prepare ortho(alkyl- or arylthio)phenols as the predominant products.
Claims17
A process for the preparation of ortho(alkylthio- or arylthio)phenols wherein the alkylthio- and arylthio- moieties are of the formula RS-which comprises reacting a corresponding phenol having the formula ##STR2## wherein X and Y are independently selected from the group consisting of H, OH, C.sub.1 -C.sub.6 alkyl, OR.sub.1, Cl, F, I, Br, aryl or aryl substituted with C.sub.1 -C.sub.6 alkyl, OR.sub.1, Cl, F, I or Br, or when X and Y are on adjacent carbon atoms, they may be taken together to form CH.dbd.CH--CH.dbd.CH;
- and
- R.sub.1 is C.sub.1 -C.sub.6 alkyl or phenyl;
- provided that X and Y cannot simultaneously be OH, and when X or Y is OH and the other is hydrogen, the OH cannot be in the para position;
- with a compound selected from the group consisting of alkyl or aryl disulfides having the formula (RS).sub.2
- wherein R is C.sub.1 -C.sub.6 alkyl or aryl wherein aryl is unsbustituted or substituted with one or more substituents selected from the group consisting of C.sub.1 -C.sub.6 alkyl, Cl, F, I, Br, OR.sub.1, aryl where R.sub.1 is C.sub.1 -C.sub.6 alkyl or phenyl
- provided that when R is C.sub.4 -C.sub.6 alkyl, the carbon bonded to the heteroatom must be substituted by one or two hydrogen atoms;
- or (alkylthio- or arylthio)phenols, or mixtures of the foregoing wherein the alkylthio- and arylthio- moieties are of the formula RS- and the phenol moieties correspond to Formula I above in the presence of an aluminosilicate having catalytically active acidic sites.
Dependencies are inferred from the claim text.