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US4339614A Expired / Lapsed US ⏱️ 0.0 years remaining

Superacid catalyzed preparation of resorcinol from meta-isopropylphenol

Assignee: Produits Chimiques Ugine Kuhlmann
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Filing: 1980-03-14
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Granted: 1982-07-13
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Expires: 2000-03-14
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Abstract

Abstract Resorcinol is prepared by an improved process through superacid (such as perfluorinated alkanesulfonic acids of one to eighteen carbon atoms or polymeric perfluorinated resinsulfonic acids, such as Nafion-H catalyzed cleavage-rearrangement reaction of meta-isopropylphenol hydroperoxide in the form of its protected ether or ester derivatives, including readily cleavable and reusable trimethylsilyl and trifluoromethanesulfonyl derivates. Part of the process is the preparation of needed meta-isopropylphenol in high purity free of other isomers by treating any mixture of isopropylphenol isomers in an excess of anhydrous hydrogen fluoride or a perfluorinated alkanesulfonic acid of one to six carbon atoms and a Lewis acid fluoride or by alkylating (transalkylating) phenol with a propyl alkylating agent in the presence of the aforementioned superacid systems.

Inventors

  • 👤 George A. Olah

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 14:50
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/01; C07C37/055; C07C37/0555; C07C37/08; C07C37/11; C07C37/14; C07C37/16; C07C37/18; C07C37/48; C07C37/68; C07C37/86

Claims Analysis

Total Claims: 5
Claim 1
Independent Claim 56 words
The process of producing resorcinol, selectively in high yield, which comprises reacting an ether or ester derivative of meta-isopropylphenol hydroperoxide in which the ether or ester group is an easily cleavable phenol protecting group with a superacid cleavage rearrangement catalyst comprising a perfluoroalkanesulfonic acid at a temperature sufficient to produce resorcinol with selectively with high yields.
Claim 2
Dependent Claim 56 words
The process of producing resorcinol, selectively in high yield, which comprises reacting an ether or ester derivative of meta-isopropylphenol hydroperoxide in which the ether or ester group is an easily cleavable phenol protecting group with a superacid cleavage rearrangement catalyst comprising a perfluoroalkanesulfonic acid at a temperature sufficient to produce resorcinol with selectively with high yields.
Claim 3
Dependent Claim 22 words
The process according to claim 1 in which the superacid catalyst is a perfluorinated alkanesulfonic acid of 1 to 18 carbon atoms.
Claim 4
Dependent Claim 16 words
The process according to claim 1 in which the superacid is a polymeric perfluorinated sulfonic acid.
Claim 5
Dependent Claim 23 words
The process according to claim 1, or 2 in which the ether group is trimethylsilyl and the ester group is trifluoromethanesulfonyl or trifluoroacetyl.

References Cited (Backward Citations)

GB819450A Cited
US3028410A Cited
GB857113A Cited
GB873676A Cited
GB982514A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-07-12 1986-01-11 1986-07-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-07-12 1990-01-11 1990-07-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-07-12 1994-01-11 1994-07-13 $7700.00 Window Closed / Lapsed

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