US4008266A
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Coupling of aromatic compounds in the presence of molecular oxygen, a mercuric oxyanion compound, and a group VIII metal or group VIII metal oxyanion compound
Assignee: Monsanto Co
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Filing: 1974-01-02
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Granted: 1977-02-15
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Expires: 1994-01-02
Abstract
Abstract A catalytic process in which molecular oxygen is used to couple aromatic compounds to form a variety of polyaromatic compounds is disclosed. The process comprises reacting monoaromatic compounds in the presence of molecular oxygen and a catalyst system comprising a mercuric oxyanion compound, a Group VIII metal, or metal oxyanion compound and optionally a redox reagent consisting of a soluble salt of a multivalent metal having an oxidation potential greater than that of the Group VIII metal.
Inventors
- 👤 George M. Intille
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 01:10
CPC Classifications
C; C07; C07C; C07C17/00; C07C17/26; C07C17/263; C07C17/269; C07C2/00; C07C2/76; C07C2/82; C07C2/84; C07C201/00; C07C201/06; C07C201/12; C07C37/00; C07C37/11; C07C41/00; C07C41/01; C07C41/18; C07C41/30; C07C45/00; C07C45/27; C07C45/32; C07C45/33; C07C45/34; C07C45/36; C07C63/00; C07C63/33; C07C63/331; C07C67/00; C07C67/035; C07C67/30; C07C67/333; C07C67/343; C07C2531/00; C07C2531/02; C07C2531/04
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
104 words
A catalytic process for coupling aromatic compounds of the formula ##STR7## where n is an integer from 0 to 5 and each of the R groups is hydroxy, alkoxy, alkyl, aryloxy, aryl, acyl, alkanoate, carboxyl, carboxylic esters, halogen or nitro, and where two R groups, located on adjacent carbon atoms of the benzene ring, can be joined to form a carbocyclic or heterocyclic ring with molecular oxygen to produce coupled aromatic compounds comprising coupling said aromatic compounds with at least about 200 psi molecular oxygen in the presence of a mercuric oxyanion compound and a Group VIII metal or Group VIII metal oxyanion compound.
Claim 2
Dependent Claim
104 words
A catalytic process for coupling aromatic compounds of the formula ##STR7## where n is an integer from 0 to 5 and each of the R groups is hydroxy, alkoxy, alkyl, aryloxy, aryl, acyl, alkanoate, carboxyl, carboxylic esters, halogen or nitro, and where two R groups, located on adjacent carbon atoms of the benzene ring, can be joined to form a carbocyclic or heterocyclic ring with molecular oxygen to produce coupled aromatic compounds comprising coupling said aromatic compounds with at least about 200 psi molecular oxygen in the presence of a mercuric oxyanion compound and a Group VIII metal or Group VIII metal oxyanion compound.
Claim 3
Dependent Claim
14 words
A process according to claim 1 wherein said integer n is 0 to 1.
Claim 4
Dependent Claim
21 words
A process according to claim 2 wherein said integer n is one and said R group is hydroxy, alkoxy or aryloxy.
Claim 5
Dependent Claim
14 words
A process according to claim 1 wherein at least one R group is alkyl.
Claim 6
Dependent Claim
12 words
A process according to claim 4 wherein said alkyl group is methyl.
Claim 7
Dependent Claim
17 words
A process according to claim 1 wherein at least a portion of said aromatic compounds is phenol.
Claim 8
Dependent Claim
17 words
A process according to claim 1 wherein at least a portion of said aromatic compounds is benzene.
Claim 9
Dependent Claim
17 words
A process according to claim 1 wherein at least a portion of said aromatic compounds is toluene.
Claim 10
Dependent Claim
19 words
A process according to claim 1 wherein at least one of said R groups is carboxyl or carboxylic ester.
Claim 11
Dependent Claim
18 words
A process according to claim 1 wherein at least a portion of said aromatic compounds is diphenyl ether.
Claim 12
Dependent Claim
22 words
A process according to claim 1 wherein said Group VIII metal or Group VIII metal oxyanion compound is a metal oxyanion compound.
Claim 13
Dependent Claim
19 words
A process according to claim 11 wherein the metal component of said Group VIII metal oxyanion compound is palladium.
Claim 14
Dependent Claim
17 words
A process according to claim 11 wherein the Group VIII metal oxyanion compound is a palladium oxy-salt.
Claim 15
Dependent Claim
17 words
A process according to claim 11 wherein said Group VIII metal oxyanion compound is a palladium carboxylate.
Claim 16
Dependent Claim
15 words
A process according to claim 1 wherein said mercuric oxyanion compound is a mercuric oxy-salt.
Claim 17
Dependent Claim
15 words
A process according to claim 1 wherein said mercuric oxyanion compound is a mercuric carboxylate.
Claim 18
Dependent Claim
52 words
A process according to claim 1 wherein the reacting of said aromatic compound with molecular oxygen is conducted in the presence of a mercuric oxyanion compound, a Group VIII metal or metal oxyanion compound, and redox compound capable of oxidizing the Group VIII metal and capable of being oxidized by molecular oxygen.
Claim 19
Dependent Claim
16 words
A process according to claim 17 wherein said redox compound is a ferric or cupric salt.
Claim 20
Dependent Claim
16 words
A process according to claim 18 wherein said redox compound is a ferric or cupric carboxylate.
Claim 21
Dependent Claim
64 words
A process for coupling aromatic compounds of the formula ##STR8## where n is an integer from 0 to 1 and the R group is hydroxy, alkoxy, carboxyl, alkyl, aryl, aryloxy or halogen, comprising reacting said compounds with at least about 200 psi molecular oxygen in the presence of a catalyst system comprising a mercuric oxy-salt, a Group VIII metal oxy-salt and a redox agent.
Claim 22
Dependent Claim
64 words
A process for coupling aromatic compounds of the formula ##STR8## where n is an integer from 0 to 1 and the R group is hydroxy, alkoxy, carboxyl, alkyl, aryl, aryloxy or halogen, comprising reacting said compounds with at least about 200 psi molecular oxygen in the presence of a catalyst system comprising a mercuric oxy-salt, a Group VIII metal oxy-salt and a redox agent.
Claim 23
Dependent Claim
26 words
A process according to claim 20 wherein said Group VIII metal oxy-salt is a palladium oxy-salt and said redox agent is a cupric or ferric salt.
Claim 24
Dependent Claim
18 words
A process according to claim 20 wherein said catalyst system comprises mercuric acetate, palladium acetate and cupric acetate.
Claim 25
Dependent Claim
16 words
A process according to claim 1 wherein the reaction is conducted homogeneously in the liquid phase.
Claim 26
Dependent Claim
16 words
A process according to claim 1 wherein the reaction is conducted heterogenously in the gas phase.
Claim 27
Dependent Claim
22 words
A process according to claim 1 wherein said aromatic compound is toluene and at least one of the products is dimethyl biphenyl.
Claim 28
Dependent Claim
32 words
A process according to claim 1 wherein said aromatic compound is benzoic acid or an ester thereof and at least one of the products is dicarboxylic acid diphenyl or an ester thereof.
Claim 29
Dependent Claim
21 words
A process according to claim 1 wherein said aromatic compound is xylene and the products are tetramethyl biphenyl and methylphenyl-dimethylphenyl methane.
Claim 30
Dependent Claim
22 words
A process according to claim 1 wherein said aromatic compound is anisole and at least one of the products is dimethyl biphenyl.
Claim 31
Dependent Claim
22 words
A process according to claim 1 wherein said aromatic compound is ethylbenzene and at least one of the products is diethyl biphenyl.
Claim 32
Dependent Claim
102 words
A catalytic process for coupling aromatic compounds of the formula ##STR9## where n is an integer from 0 to 5 and each of the R groups is hydroxy, alkoxy, alkyl, aryloxy, aryl, acyl, alkanoate, carboxyl, carboxylic esters, halogen or nitro, and where two R groups, located on adjacent carbon atoms of the benzene ring, can be joined to form a carbocyclic ring with molecular oxygen to produce coupled aromatic compounds comprising coupling said aromatic compounds with at least about 200 psi molecular oxygen in the presence of a mercuric oxyanion compound and a Group VIII metal or Group VIII metal oxyanion compound.
Claim 33
Dependent Claim
102 words
A catalytic process for coupling aromatic compounds of the formula ##STR9## where n is an integer from 0 to 5 and each of the R groups is hydroxy, alkoxy, alkyl, aryloxy, aryl, acyl, alkanoate, carboxyl, carboxylic esters, halogen or nitro, and where two R groups, located on adjacent carbon atoms of the benzene ring, can be joined to form a carbocyclic ring with molecular oxygen to produce coupled aromatic compounds comprising coupling said aromatic compounds with at least about 200 psi molecular oxygen in the presence of a mercuric oxyanion compound and a Group VIII metal or Group VIII metal oxyanion compound.
References Cited (Backward Citations)
US3539622A
Cited
US3728409A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-02-15 | 1980-08-16 | 1981-02-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-02-15 | 1984-08-16 | 1985-02-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-02-15 | 1988-08-16 | 1989-02-15 | $7700.00 | Window Closed / Lapsed |