US4623726A
Expired / Lapsed
US
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Method for oxidizing alkyl groups on pyridine, quinoline and benzene ring compounds to carboxylic acids under basic conditions
Assignee: BASF SE
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Filing: 1983-04-18
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Granted: 1986-11-18
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Expires: 2003-04-18
Abstract
Abstract There is provided a novel process for the preparation of carboxylic acids from alkyl groups under basic conditions utilizing oxides of copper, cobalt and silver.
Inventors
- 👤 William A. Daniels
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 13:31
CPC Classifications
C; C07; C07B; C07B33/00; C07C; C07C51/00; C07C51/16; C07C51/21; C07C51/215; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/79; C07D213/803; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/54
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
106 words
A method for the oxidation of one or more CH 3 groups to a carboxylic acid product, wherein said CH 3 group is attached to a pyridine, quinoline or benzene ring compound, said method comprising: reacting said CH 3 substituted compound with a hydroxide or oxide of formula (I) X.sub.m Y.sub.n (I) wherein X is copper, cobalt or silver; Y is oxygen or hydroxyl; m is an integer of 1 or 2; n is an integer of 2 to 6; and n>m; with a molar excess of 50% to 250% of an aqueous hypochlorite salt at a temperature of 25° C. to 95° C. at pH>9.
Claim 2
Independent Claim
106 words
A method for the oxidation of one or more CH 3 groups to a carboxylic acid product, wherein said CH 3 group is attached to a pyridine, quinoline or benzene ring compound, said method comprising: reacting said CH 3 substituted compound with a hydroxide or oxide of formula (I) X.sub.m Y.sub.n (I) wherein X is copper, cobalt or silver; Y is oxygen or hydroxyl; m is an integer of 1 or 2; n is an integer of 2 to 6; and n>m; with a molar excess of 50% to 250% of an aqueous hypochlorite salt at a temperature of 25° C. to 95° C. at pH>9.
Claim 3
Dependent Claim
18 words
A method according to claim 1, wherein said hydroxide or oxide of copper, cobalt or silver is CuO.
Claim 4
Dependent Claim
30 words
A method according to claim 2, wherein said CH 3 -substituted mono-nitrogen heterocyclic ring or benzene ring compound is 2-methyl nicotinic acid; and said carboxylic acid product is 2,3-pyridinecarboxylic acid.
Claim 5
Dependent Claim
29 words
A method according to claim 2, wherein said CH 3 -substituted mono-nitrogen heterocyclic ring or benzene ring compound is 2-methyl-3-quinolinecarboxylic acid; and said carboxylic said product is 2,3-quinolinedicarboxylic acid.
Claim 6
Independent Claim
101 words
A method for the oxidation of one or more CH 3 groups to carboxylic acid product, wherein said CH 3 group is attached to a mono-nitrogen heterocyclic ring or benzene ring compound, said method comprising: reacting said CH 3 -substituted mono-nitrogen heterocyclic ring or benzene ring compound with an oxide or hydroxide of formula (I) XmYn (I) wherein X is copper, cobalt or silver; Y is oxygen; m is an integer of 1 or 2; n is an integer of 2 to 6; and n≧m; with 50% to 250% molar excess of chlorine gas; and conducting said reaction at a pH>9.
Claim 7
Independent Claim
101 words
A method for the oxidation of one or more CH 3 groups to carboxylic acid product, wherein said CH 3 group is attached to a mono-nitrogen heterocyclic ring or benzene ring compound, said method comprising: reacting said CH 3 -substituted mono-nitrogen heterocyclic ring or benzene ring compound with an oxide or hydroxide of formula (I) XmYn (I) wherein X is copper, cobalt or silver; Y is oxygen; m is an integer of 1 or 2; n is an integer of 2 to 6; and n≧m; with 50% to 250% molar excess of chlorine gas; and conducting said reaction at a pH>9.
Claim 8
Dependent Claim
20 words
A method according to claim 5, wherein said oxide or hydroxide of copper, cobalt or silver is Cu(OH) 2 .
Claim 9
Dependent Claim
30 words
A method according to claim 6, wherein said CH 3 -substituted mono-nitrogen heterocyclic ring or benzene ring compound is 2-methyl nicotinic acid; and said carboxylic acid product is 2,3-pyridinecarboxylic acid.
Claim 10
Dependent Claim
29 words
A method according to claim 6, wherein said CH 3 -substituted mono-nitrogen heterocyclic ring or benzene ring compound is 2-methyl-3-quinolinecarboxylic acid; and said carboxylic acid product is 2,3-quinolinedicarboxylic acid.
Claim 11
Dependent Claim
29 words
A method according to claim 6, wherein said CH 3 -substituted mono-nitrogen heterocyclic ring or benzene ring compound is o-toluic acid; and said carboxylic acid product is phthalic acid.
Claim 12
Dependent Claim
28 words
A method according to claim 6, wherein said CH 3 -substituted mono-nitrogen heterocyclic ring or benzene ring compound is 3-(3-pyridinyl)propanol; and said carboxylic acid product is nicotinic acid.
Claim 13
Dependent Claim
28 words
A method according to claim 6, wherein said CH 3 -substituted mono-nitrogen heterocyclic ring or benzene ring compound is 1,2,4-trimethylbenzene; and said carboxylic acid product is 1,2,4-benzenitricarboxylic acid.
Claim 14
Dependent Claim
31 words
A method according to claim 6, wherein said CH 3 -substituted mono-nitrogen heterocyclic ring or benzene ring compound 2,3-lutidine; and said carboxylic acid product is 2,3-pyridinedicarboxylic acid or 2-methyl nicotinic acid.
Claim 15
Dependent Claim
15 words
A method according to claim 6, wherein said oxide or hydroxide of XmYn is CoO.
Claim 16
Dependent Claim
29 words
A method according to claim 13, wherein said CH 3 -substituted mono-nitrogen heterocyclic ring or benzene ring compound is 2-methyl-3-quinolinecarboxylic acid; and said carboxylic acid product is 2,3-quinolinedicarboxylic acid.
References Cited (Backward Citations)
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