Patent US4123470A successfully refreshed from Google Patents.
US4123470A
Expired / Lapsed
US
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Biaryl production
Assignee: Phillips Petroleum Co
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Filing: 1977-06-06
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Granted: 1978-10-31
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Expires: 1997-06-06
Abstract
Abstract Aromatic hydrocarbons are converted to biaryl compounds in a two-step process comprising hydroalkylation of the aromatic hydrocarbons to cycloalkyl aromatic hydrocarbons followed by dehydrogenation in the presence of a metal dehydrogenation catalyst and an acidic support to convert the cycloalkyl aromatic hydrocarbons to biaryl compounds. In one embodiment, benzene is hydroalkylated to cyclohexylbenzene, and the cyclohexylbenzene then dehydrogenated to biphenyl.
Inventors
- 👤 Timothy P. Murtha
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 18:43
CPC Classifications
C; C07; C07C; C07C15/00; C07C15/12; C07C15/14; C07C2/00; C07C2/74; C07C5/00; C07C5/32; C07C5/367; C07C2521/00; C07C2521/02; C07C2521/04; C07C2521/16; C07C2523/00; C07C2523/38; C07C2523/40; C07C2523/42; C07C2523/46; C07C2527/00; C07C2527/06; C07C2527/128; C07C2527/13; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
81 words
A process for the production of biaryl compounds from monocyclic aromatic hydrocarbons which comprises: (a) contacting at least one monocyclic aromatic hydrocarbon with hydrogen in the presence of a hydroalkylation catalyst and under hydroalkylation conditions which produce cycloalkyl aromatic hydrocarbons, and (b) treating said cycloalkyl aromatic hydrocarbons produced in (a) with hydrogen in the presence of a metal dehydrogenation catalyst on an acidic support and under dehydrogenation conditions which produce biaryl compounds substantially free of by-product triaryls and higher ring assemblies.
Claim 2
Dependent Claim
81 words
A process for the production of biaryl compounds from monocyclic aromatic hydrocarbons which comprises: (a) contacting at least one monocyclic aromatic hydrocarbon with hydrogen in the presence of a hydroalkylation catalyst and under hydroalkylation conditions which produce cycloalkyl aromatic hydrocarbons, and (b) treating said cycloalkyl aromatic hydrocarbons produced in (a) with hydrogen in the presence of a metal dehydrogenation catalyst on an acidic support and under dehydrogenation conditions which produce biaryl compounds substantially free of by-product triaryls and higher ring assemblies.
Claim 3
Dependent Claim
37 words
A process according to claim 1 wherein the effluent from (a) is treated in (b) without any separation of the components of said effluent to convert the cycloalkyl aromatic hydrocarbon components present to the corresponding biaryl hydrocarbon.
Claim 4
Dependent Claim
50 words
A process according to claim 1 wherein the effluent from (a) is subjected to separation to separate the cycloalkyl aromatic hydrocarbon from said effluent in a relatively pure state followed by treatment of the separated cycloalkyl aromatic hydrocarbon with hydrogen under dehydrogenation conditions in (b) to obtain the biaryl hydrocarbon.
Claim 5
Dependent Claim
18 words
A process according to claim 1 wherein an inert hydrocarbon diluent is present in the feed to (b).
Claim 6
Dependent Claim
112 words
A process according to claim 1 wherein (a) said monocyclic aromatic hydrocarbon contains from 6 to about 12 carbon atoms per molecule, said catalyst is a ruthenium halide-active clay or rhodium-active clay catalyst, and said hydroalkylation conditions include a temperature ranging from about 100° C. to about 250° C. and a hydrogen pressure of from about 100 psig to about 2,000 psig (690-13,800 kPa), and (b) said catalyst is a noble metal on an acidic support, and said dehydrogenation conditions include a temperature ranging from about 200° C. to about 550° C. and a mole ratio of hydrogen to cycloalkyl aromatic hydrocarbon of about 0.1 to 1 to about 20 to 1.
Claim 7
Dependent Claim
54 words
A process according to claim 1 wherein unreacted aromatic hydrocarbons are recovered from the effluent from (b) and are recycled to (a) and unreacted cycloalkyl aromatic hydrocarbon in the effluent from (b) is recovered and recycled to (b) and unreacted hydrogen is recovered from the effluent of (b) and recycled to (a) and/or (b).
Claim 8
Dependent Claim
54 words
A process according to claim 1 for converting benzene to biphenyl which comprises: (a) contacting benzene with hydrogen under hydroalkylation conditions which produce cyclohexylbenzene, and (b) treating the cyclohexylbenzene produced in (a) with hydrogen in the presence of a catalyst comprising a noble metal on an acidic support under dehydrogenation conditions which produce biphenyl.
Claim 9
Dependent Claim
39 words
A process according to claim 7 wherein the catalyst in (b) is platinum-alumina, the temperature in (b) ranges from about 350° C. to about 450° C., and the feed passed to (b) is a mixture of benzene and cyclohexylbenzene.
References Cited (Backward Citations)
US3274276A
Cited
US3829516A
Cited
US3829514A
Cited
US3829517A
Cited
US3829515A
Cited
US3956183A
Cited
US3928481A
Cited
US3962362A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-30 | 1982-05-01 | 1982-10-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-30 | 1986-05-01 | 1986-10-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-30 | 1990-05-01 | 1990-10-31 | $7700.00 | Window Closed / Lapsed |