Patent US4532368A successfully refreshed from Google Patents.
US4532368A
Expired / Lapsed
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Process for making meta- and para-alkylphenols
Assignee: Ethyl Corp
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Filing: 1984-02-01
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Granted: 1985-07-30
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Expires: 2004-02-01
Abstract
Abstract A process for making a mixture of meta- and para-alkylphenols by contacting a mixture of phenol, ortho-alkylphenol and an alkylating agent (e.g. olefins or lower alcohols) with a zeolite having a silica:alumina ratio of at least 12:1 under alkylating conditions to obtain a mixture of ortho-, meta- and para-alkylphenols and then separating at least part of the ortho-alkylphenol which is recycled to a subsequent alkylation process carried out in the same manner.
Inventors
- 👤 Barry J. Swanson
- 👤 Ronald L. Shubkin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 20:37
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/11; C07C37/16; B; B01; B01J; B01J29/00; B01J29/04; B01J29/06; B01J29/40; C07C37/14; B01J2229/00; B01J2229/10; B01J2229/18
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
143 words
A process for making a mixture of meta- and para-alkylphenols containing only minor amounts of ortho-alkylphenol, said process comprising (a) passing a mixture of phenol, ortho-alkylphenol, and an alkylating agent selected from the group consisting of lower alcohols and olefins, through a zeolite catalyst having a silica:alumina mole ratio of at least about 12:1 under alkylating conditions at a temperature of about 200°-500° C. to obtain a mixture of ortho-, meta- and para-alkylphenols, (b) separating at least part of said ortho-alkylphenols from said mixture of ortho-, meta- and para-alkylphenols forming said mixture of meta- and para-alkylphenols containing only minor amounts of ortho-alkylphenols and (c) recycling the separated ortho-alkylphenol to a subsequent alkylation carried out as defined in step (a), (b) and (c) wherein said separated ortho-alkylphenol is used as said ortho-alkylphenol in said mixture of phenol, ortho-alkylphenol and alkylating agent in step (a).
Claim 2
Dependent Claim
143 words
A process for making a mixture of meta- and para-alkylphenols containing only minor amounts of ortho-alkylphenol, said process comprising (a) passing a mixture of phenol, ortho-alkylphenol, and an alkylating agent selected from the group consisting of lower alcohols and olefins, through a zeolite catalyst having a silica:alumina mole ratio of at least about 12:1 under alkylating conditions at a temperature of about 200°-500° C. to obtain a mixture of ortho-, meta- and para-alkylphenols, (b) separating at least part of said ortho-alkylphenols from said mixture of ortho-, meta- and para-alkylphenols forming said mixture of meta- and para-alkylphenols containing only minor amounts of ortho-alkylphenols and (c) recycling the separated ortho-alkylphenol to a subsequent alkylation carried out as defined in step (a), (b) and (c) wherein said separated ortho-alkylphenol is used as said ortho-alkylphenol in said mixture of phenol, ortho-alkylphenol and alkylating agent in step (a).
Claim 3
Dependent Claim
26 words
A process of claim 1 wherein said zeolite catalyst is selected from the group consisting of ZSM-5, ZSM-11, ZSM-12, ZSM-23, ZSM-35, ZSM-38, ZSM-48, Silicalite and Silicalite-2.
Claim 4
Dependent Claim
11 words
A process of claim 2 wherein said zeolite catalyst is ZSM-5.
Claim 5
Dependent Claim
11 words
A process of claim 3 wherein said ZSM-5 is phosphorus promoted.
Claim 6
Dependent Claim
11 words
A process of claim 2 wherein said zeolite catalyst is Silicalite.
Claim 7
Dependent Claim
11 words
A process of claim 5 wherein said Silicalite is silicone promoted.
Claim 8
Dependent Claim
19 words
A process of claim 2 wherein said alkylating agent is an alcohol containing 1 to about 12 carbon atoms.
Claim 9
Dependent Claim
15 words
A process of claim 7 wherein said alcohol contains 2 to about 4 carbon atoms.
Claim 10
Dependent Claim
11 words
A process of claim 8 wherein said zeolite catalyst is ZSM-5.
Claim 11
Dependent Claim
11 words
A process of claim 9 wherein said ZSM-5 is phosphorus promoted.
Claim 12
Dependent Claim
11 words
A process of claim 8 wherein said zeolite catalyst is Silicalite.
Claim 13
Dependent Claim
11 words
A process of claim 11 wherein said Silicalite is silicone promoted.
Claim 14
Dependent Claim
11 words
A process of claim 1 wherein said alkylating agent is ethanol.
Claim 15
Dependent Claim
11 words
A process of claim 13 wherein said zeolite catalyst is ZSM-5.
Claim 16
Dependent Claim
11 words
A process of claim 14 wherein said ZSM-5 is phosphorus promoted.
Claim 17
Dependent Claim
11 words
A process of claim 13 wherein said zeolite catalyst is Silicalite.
Claim 18
Dependent Claim
11 words
A process of claim 16 wherein said Silicalite is silicon promoted.
Claim 19
Dependent Claim
138 words
A process for making a mixture of meta- and para-alkylphenols containing none or a minor amount of ortho-alkylphenol, said process comprising (a) contacting a mixture of phenol and alkylating agent selected from the group consisting of lower alcohols, olefins and mixtures thereof and optionally including an ortho-alkylphenol, with a crystalline zeolite catalyst having a silica: alumina mole ratio of at least 12:1 under alkylating conditions at a temperature of about 200°-500° C. to obtain a mixture of ortho-, meta- and para- alkylphenols, (b) separating at least part of said ortho-alkylphenol from said mixture of ortho-, meta- and para- alkylphenols forming said mixture of meta- and para- alkylphenols containing none or minor amounts of ortho-alkylphenol and (c) recycling the separated ortho-alkylphenol to a subsequent alkylation carried out to include the above steps (a) and (b) and optionally step (c).
Claim 20
Dependent Claim
138 words
A process for making a mixture of meta- and para-alkylphenols containing none or a minor amount of ortho-alkylphenol, said process comprising (a) contacting a mixture of phenol and alkylating agent selected from the group consisting of lower alcohols, olefins and mixtures thereof and optionally including an ortho-alkylphenol, with a crystalline zeolite catalyst having a silica: alumina mole ratio of at least 12:1 under alkylating conditions at a temperature of about 200°-500° C. to obtain a mixture of ortho-, meta- and para- alkylphenols, (b) separating at least part of said ortho-alkylphenol from said mixture of ortho-, meta- and para- alkylphenols forming said mixture of meta- and para- alkylphenols containing none or minor amounts of ortho-alkylphenol and (c) recycling the separated ortho-alkylphenol to a subsequent alkylation carried out to include the above steps (a) and (b) and optionally step (c).
Claim 21
Dependent Claim
38 words
A process of claim 18 further characterized in that said ortho-alkylphenol is included in step (a) and that at least part of said ortho-alkylphenol is recycled from step (b) of a previous process conducted according to claim 18.
Claim 22
Dependent Claim
114 words
A process for making a mixture of meta- and para- alkylphenols containing none or a minor amount of ortho-alkylphenol, said process comprising (a) contacting a mixture of phenol, an alkylating agent selected from the group consisting of lower alcohols, olefins and mixtures thereof and an ortho-alkylphenol with a crystalline zeolite catalyst having a silica:alumina mole ratio of at least 12:1 under alkylating conditions at a temperature of about 200°-500° C. to obtain a mixture of ortho-, meta- and para- alkylphenols and (b) separating at least part of said ortho-alkylphenol from said mixture of ortho-, meta- and para- alkylphenols forming said mixture of meta- and para- alkylphenols containing none or a minor amount of ortho-alkylphenol.
Claim 23
Dependent Claim
114 words
A process for making a mixture of meta- and para- alkylphenols containing none or a minor amount of ortho-alkylphenol, said process comprising (a) contacting a mixture of phenol, an alkylating agent selected from the group consisting of lower alcohols, olefins and mixtures thereof and an ortho-alkylphenol with a crystalline zeolite catalyst having a silica:alumina mole ratio of at least 12:1 under alkylating conditions at a temperature of about 200°-500° C. to obtain a mixture of ortho-, meta- and para- alkylphenols and (b) separating at least part of said ortho-alkylphenol from said mixture of ortho-, meta- and para- alkylphenols forming said mixture of meta- and para- alkylphenols containing none or a minor amount of ortho-alkylphenol.
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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) | 1988-07-29 | 1989-01-28 | 1989-07-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-07-29 | 1993-01-28 | 1993-07-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-07-29 | 1997-01-28 | 1997-07-30 | $7700.00 | Window Closed / Lapsed |