# US 5,347,057 A · Method for oxidation of methane and other hydro-carbons

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- Number: US 5,347,057 A
- Document ID: US5347057A
- Status: Granted
- Kind: A
- Application number: 08/008,185
- Filed: 1993-01-25
- Granted: 1994-09-13
- Earliest claimed: 1993-01-25
- Inventors: Mirza M. T. Khan
- Web page: https://patentgrep.com/patent/US5347057A

## CPC

- C07C 29/50: with molecular oxygen only
- C07C 45/33: of CHx-moieties
- Y02P 20/52: using catalysts, e.g. selective catalysts
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

This invention teaches the oxidation of alkanes and cycloalkanes in the presence of air or oxygen and a ruthenium metal complex catalyst containing an end or bridged-oxo group with a liquid L and carboxylato groups. This oxidation process results in very high yields, utilizes very little energy and has a high catalyst turnover rate.

## Claims

### Claim 1

A process for selectively oxidizing alkanes or aromatic hydrocarbons where the products of oxidation are alcohols, ketones or mixtures thereof comprising the steps of:
(a) placing the alkane or aromatic hydrocarbon in contact with oxygen, and
(b) adding a ruthenium metal complex catalyst activated by an "end-oxo"
group, said catalyst having the formula LRu=O, where L is a Schiff or a substituted Schiff base; or
a "bridging -oxo" group, said catalyst having the formula: ##STR3## wherein L is a Schiff base or a substitute Schiff base and R is H, or an alkyl (C<10) or an aryl (C<30).

### Claim 2 (depends on 1)

The process as claimed in claim 1 wherein said alkane has between 1 and 15 carbon atoms.

### Claim 3 (depends on 1)

The process as claimed in claim 1 wherein said alkane has between 1 and 10 carbon atoms.

### Claim 4 (depends on 1)

The process a claimed in claim 1 wherein the aromatic hydrocarbons have side chains that selectively oxidized and where the products of oxidation are alcohols, ketone or acids, or a mixture thereof.

### Claim 5 (depends on 1)

The process as claimed in claim 1, wherein the alkane or aromatic hydrocarbon is first added to a mixed aqueous-organic solvent.

### Claim 6 (depends on 5)

The process as claimed in claim 5, wherein the reaction temperature is between 20.degree.-60.degree. C. and the pressure is between 5-20 atmospheres.

### Claim 7 (depends on 6)

The process as claimed in claim 6, wherein said temperature is 30.degree. C. and said pressure is 14 atmospheres.

### Claim 8 (depends on 1)

The process as claimed in claim 1, wherein said ruthenium metal complex catalyst is coordinated with a Schiff base or a substituted Schiff base.

### Claim 9 (depends on 8)

The process as claimed in claim 8, wherein said ruthenium metal complex catalyst is activated by said end-oxo or said bridging-oxo group and by at least one carboxylato group.

### Claim 10 (depends on 9)

The process as claimed in claim 9, wherein said alkane is methane.

### Claim 11 (depends on 10)

The process as claimed in claim 10, wherein said methane is first added to in a mixed aqueous-organic solvent.

### Claim 12 (depends on 11)

The process as claimed in claim 11, wherein the temperature is 30.degree. C., and the pressure is 14 atmospheres of CH.sub.4 :O.sub.2.

### Claim 13

A process for selectively oxidizing alkanes or aromatic hydrocarbons comprising the steps of:
(a) adding said alkane or hydrocarbon to a mixed aqueous-organic solvent in the presence of oxygen;
(b) adding a ruthenium metal complex, activated by an end-oxo group, said catalyst having the formula LRu-), where L is a Schiff or a substituted Schiff base;
(c) or a bridging-oxo group said catalyst having the formula: ##STR4## wherein L is a Schiff base or a substituted Schiff base and R is H or alkyl (C40) or an aryl (CL30).
(d) and at least one carboxylato group to the solvent system in a concentration range of 10.sup.3 to 10.sup.-6 moles of catalyst per liter of solution and
(e) where the temperature ranges between 20.degree.-60.degree. C. and the pressure ranges between 5-20 atmospheres.

### Claim 14 (depends on 13)

The process as claimed in claim 13, wherein said temperature is 30.degree. C. and said pressure is 14 atmosphere of CH.sub.4 :O.sub.2.

### Claim 15 (depends on 14)

The process as claimed in claim 14, wherein said alkane is methane.

### Claim 16 (depends on 15)

The process as claimed in claim 15, wherein said ruthenium metal complex is coordinated with a Schiff base or a substituted Schiff base.