US4532368A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for making meta- and para-alkylphenols
Assignee: Ethyl Corp
•
Filing: 1984-02-01
•
Granted: 1985-07-30
•
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 07:31
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.
References Cited (Backward Citations)
SU352868A1
Cited
GB1150209A
Cited
US3706807A
Cited
US3728408A
Cited
JPS4943943A
Cited
SU455743A1
Cited
US3992455A
Cited
SU730675A1
Cited
SU692825A1
Cited
SU863588A1
Cited
US4283573A
Cited
US4371714A
Cited
US4391998A
Cited
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 |