US4570011A
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Preparation of cyclobutene substituted aromatic hydrocarbons
Assignee: Dow Chemical Co
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Filing: 1984-05-21
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Granted: 1986-02-11
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Expires: 2004-05-21
Abstract
Abstract The invention is a process for the preparation of an aromatic hydrocarbon with a cyclobutene ring fused to the aromatic hydrocarbon which comprises, dissolving an ortho alkyl halomethyl aromatic hydrocarbon in an inert solvent and pyrolyzing the solution of ortho alkyl halomethyl aromatic hydrocarbon in the inert solvent under conditions such that the ortho alkyl and halomethyl substituents form a cyclobutene ring thereby forming an aromatic hydrocarbon having a fused cyclobutene ring.
Inventors
- 👤 Ying-Hung So
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 05:03
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/76
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
95 words
A process for the preparation of an aromatic hydrocarbon with a cyclobutene ring fused to the aromatic hydrocarbon which comprises, dissolving an ortho alkyl halomethyl aromatic hydrocarbon wherein the carbon atom of the ortho alkyl group directly bound to the aromatic ring has at least one hydrogen atom bound to said carbon atom; in an inert solvent and pyrolyzing the solution of ortho alkyl halomethyl aromatic hydrocarbon in the inert solvent under conditions such that the ortho alkyl and halomethyl substituents form a cyclobutene ring thereby forming an aromatic hydrocarbon having a fused cyclobutene ring.
Claim 2
Dependent Claim
95 words
A process for the preparation of an aromatic hydrocarbon with a cyclobutene ring fused to the aromatic hydrocarbon which comprises, dissolving an ortho alkyl halomethyl aromatic hydrocarbon wherein the carbon atom of the ortho alkyl group directly bound to the aromatic ring has at least one hydrogen atom bound to said carbon atom; in an inert solvent and pyrolyzing the solution of ortho alkyl halomethyl aromatic hydrocarbon in the inert solvent under conditions such that the ortho alkyl and halomethyl substituents form a cyclobutene ring thereby forming an aromatic hydrocarbon having a fused cyclobutene ring.
Claim 3
Dependent Claim
22 words
The process of claim 1 wherein the weight ratio of solvent to the ortho alkyl halomethyl aromatic hydrocarbon is 2:1 or greater.
Claim 4
Dependent Claim
18 words
The process of claim 2 wherein the solvent is benzene, a substituted benzene, diphenyl or a substituted diphenyl.
Claim 5
Dependent Claim
21 words
The process of claim 3 wherein the solvent is a benzene, toluene, xylene, a chlorobenzene, nitrobenzene, alkyl benzoate, phenylacetate, or diphenylacetate.
Claim 6
Dependent Claim
10 words
The process of claim 4 wherein the solvent is xylene.
Claim 7
Dependent Claim
14 words
The process of claim 5 wherein the pyrolysis temperature is 550° C. or greater.
Claim 8
Dependent Claim
17 words
The process of claim 6 wherein the pyrolysis pressure is between about 10 and 760 mm Hg.
Claim 9
Dependent Claim
16 words
The process of claim 7 wherein the pressure is between about 25 and 75 mm Hg.
Claim 10
Dependent Claim
24 words
The process of claim 8 wherein the aromatic radical of the substituted aromatic hydrocarbon is benzene, naphthalene, phenanthracene, anthracene, biphenyl, binaphthyl or a diarylalkane.
Claim 11
Dependent Claim
22 words
The process of claim 9 wherein the aromatic radical of the substituted aromatic hydrocarbon is benzene, naphthalene, biphenyl, binaphthyl or a diphenylalkane.
Claim 12
Dependent Claim
16 words
The process of claim 10 wherein the aromatic radical of the substituted aromatic hydrocarbon is benzene.
Claim 13
Dependent Claim
78 words
The process of claim 11 wherein the ortho alkyl halomethyl aromatic hydrocarbon corresponds to the formula ##STR13## and the aromatic hydrocarbon with a fused cyclobutene ring corresponds to the formula ##STR14## wherein R 1 is separately in each occurrence hydrogen or C 1-20 alkyl; and R is separately in each occurrence carbonyloxyhydrocarbyl, oxycarbonylhydrocarbyl, carboxamide, carboxy, carbonylhalo, cyano, nitro, hydroxy, hydrocarbyloxy or halo; X is chloro or bromo; and a is an integer of between 0 and 4, inclusive.
Claim 14
Dependent Claim
32 words
The process of claim 12 wherein R 1 is hydrogen or C 1-3 alkyl; R 2 is carbonyloxyhydrocarbyl, oxycarbonylhydrocarbyl, carboxamide, carboxy, carbonylhalo, nitro or hydrocarbyloxy; X is chlorine; and a is 1.
Claim 15
Dependent Claim
19 words
The process of claim 13 wherein R 1 is hydrogen; and R 2 is carbonyloxyhydrocarbyl, oxycarbonylhydrocarbyl, carboxamide or hydrocarbyloxy.
Claim 16
Dependent Claim
10 words
The process of claim 14 wherein R 2 is carbonyloxyalkyl.
Claim 17
Dependent Claim
10 words
The process of claim 15 wherein R 2 is carbonyloxymethyl.
References Cited (Backward Citations)
No citation records indexed.
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