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US4568782A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of indenes

Assignee: SOHIO A CORP OF OHIO
•
Filing: 1985-06-17
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Granted: 1986-02-04
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Expires: 2005-06-17
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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)

CA625240A Cited
US3210433A Cited
SU513962A1 Cited
US4232178A Cited

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

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