US4568782A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of indenes
Assignee: SOHIO A CORP OF OHIO
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Filing: 1985-06-17
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Granted: 1986-02-04
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Expires: 2005-06-17
Abstract
Abstract Disclosed is the vapor phase cyclodehydration of an aldehyde or ketone over a solid Lewis acid as catalyst to make indene or a substituted indene according to the equation: ##STR1##
Inventors
- 👤 Marco Pagnotta
- 👤 Mark C. Cesa
- 👤 James D. Burrington
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 06:52
CPC Classifications
C; C07; C07C; C07C13/00; C07C13/28; C07C13/32; C07C13/45; C07C13/465; C07C1/00; C07C1/20; C07C1/24; C07C2602/00; C07C2602/02; C07C2602/04; C07C2602/08
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
158 words
A process for the synthesis of indene and substituted indenes by the catalytic cyclodehydration of a substrate substituted and unsubstituted 3-phenylpropionaldehydes and 3-phenylpropylketones, according to the equation: ##STR3## wherein no R group contains ethylenic or acetylenic unsaturation; wherein the R group attached to the carbonyl group is selected from H and hydrocarbyl and each of the remaining R groups is selected independently from hydrogen. halo, nitro. trihalomethyl, acyl, acyloxy, acylthio, lower alkyl secondary amino where each alkyl has 1-4 C atoms. and hydrocarbyl. hydrocarbyloxy and hydrocarbylthio having 1-10 C atoms; wherein hydrocarbyl ring(s) can be formed from one or more adjacent pairs of R groups on the benzene ring; and wherein one of the R groups attached to the benzylic carbon can form a hydrocarbyl ring with the R group attached to the ortho position, said cyclodehydration being effected by passing the starting material aldehyde or ketone in the vapor phase over a solid Lewis acid as catalyst.
Claim 2
Dependent Claim
158 words
A process for the synthesis of indene and substituted indenes by the catalytic cyclodehydration of a substrate substituted and unsubstituted 3-phenylpropionaldehydes and 3-phenylpropylketones, according to the equation: ##STR3## wherein no R group contains ethylenic or acetylenic unsaturation; wherein the R group attached to the carbonyl group is selected from H and hydrocarbyl and each of the remaining R groups is selected independently from hydrogen. halo, nitro. trihalomethyl, acyl, acyloxy, acylthio, lower alkyl secondary amino where each alkyl has 1-4 C atoms. and hydrocarbyl. hydrocarbyloxy and hydrocarbylthio having 1-10 C atoms; wherein hydrocarbyl ring(s) can be formed from one or more adjacent pairs of R groups on the benzene ring; and wherein one of the R groups attached to the benzylic carbon can form a hydrocarbyl ring with the R group attached to the ortho position, said cyclodehydration being effected by passing the starting material aldehyde or ketone in the vapor phase over a solid Lewis acid as catalyst.
Claim 3
Dependent Claim
13 words
A process accordng to claim 1 wherein said substrate contains 9-35 C atoms.
Claim 4
Dependent Claim
20 words
A process according to claim 1 wherein the temperature of the cyclodehydration reaction is in the range from 50-600° C.
Claim 5
Dependent Claim
20 words
A process according to claim 1 wherein the temperature of the cyclodehydration reaction is in the range from 200-500° C.
Claim 6
Dependent Claim
16 words
A process of claim 4 wherein the contact time is in the range from 0.01-100 seconds.
Claim 7
Dependent Claim
12 words
A process of claim 4 wherein the contact time is 0.1-10 seconds.
Claim 8
Dependent Claim
22 words
A process according to claim 2 wherein the R groups not on the benzene ring are independently chosen from H and methyl.
Claim 9
Dependent Claim
16 words
A process according to claim 7 wherein all R groups on the benzene ring are H.
Claim 10
Dependent Claim
19 words
A process according to claim 1 wherein said substrate is 3-phenylpropionaldehyde and the product of said synthesis is indene.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-02-03 | 1989-08-05 | 1990-02-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-02-03 | 1993-08-05 | 1994-02-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-02-03 | 1997-08-05 | 1998-02-04 | $7700.00 | Window Closed / Lapsed |