US5162579A
Expired / Lapsed
US
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Preparation of alkoxyalkanoic acids
Assignee: Shell USA Inc
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Filing: 1991-08-30
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Granted: 1992-11-10
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Expires: 2011-08-30
Abstract
Abstract A process for the preparation of an alkoxyalkanoic acid of the formula RO(CH.sub.2 CHR'O).sub.n CH.sub.2 CO.sub.2 H wherein R is an alkyl group of from 1 to about 22 carbon atoms, R' is hydrogen or methyl or mixtures thereof (on the individual molecule) and n is an integer of from 1 to about 12, which comprises reacting the corresponding alkoxyalkanol with a stable free radical nitroxide having the formula: ##STR1## wherein each of R 1 , R 2 , R 3 and R 4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R 5 and R 6 is alkyl, hydrogen, aryl or a substituted heteroatom, and nitric acid in the presence of an oxidant at a temperature in the range of from about 0° C. to about 100° C. and thereafter separating out the alkoxyalkanoic acid.
Inventors
- 👤 Herbert E. Fried
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 20:05
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/16; C07C51/27
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
147 words
A process for the preparation of an alkoxyalkanoic acid of the formula RO(CH.sub.2 CHR'O).sub.n CH.sub.2 CO.sub.2 H wherein R is an alkyl group of from 1 to about 22 carbon atoms, R' is hydrogen or methyl or mixtures thereof (on the individual molecule) and n is an integer of from 1 to about 12, which comprises reacting the corresponding alkoxyalkanol with a stable free radical nitroxide having the formula: ##STR5## wherein each of R 1 , R 2 , R 3 and R 4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R 5 and R 6 is alkyl, hydrogen, aryl or a substituted heteroatom, and nitric acid in the presence of an oxidant at a temperature in the range of from about 0° C. to about 100° C. and thereafter separating out the alkoxyalkanoic acid.
Claim 2
Dependent Claim
147 words
A process for the preparation of an alkoxyalkanoic acid of the formula RO(CH.sub.2 CHR'O).sub.n CH.sub.2 CO.sub.2 H wherein R is an alkyl group of from 1 to about 22 carbon atoms, R' is hydrogen or methyl or mixtures thereof (on the individual molecule) and n is an integer of from 1 to about 12, which comprises reacting the corresponding alkoxyalkanol with a stable free radical nitroxide having the formula: ##STR5## wherein each of R 1 , R 2 , R 3 and R 4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R 5 and R 6 is alkyl, hydrogen, aryl or a substituted heteroatom, and nitric acid in the presence of an oxidant at a temperature in the range of from about 0° C. to about 100° C. and thereafter separating out the alkoxyalkanoic acid.
Claim 3
Dependent Claim
27 words
The process of claim 1 wherein the stable free radical nitroxide is selected from the group consisting of 2,2,6,6-tetramethyl-piperidine-1-oxyl, 4-hydroxy-2,2,6,6-tetramethyl-piperidine-1-oxyl, 4-oxo-2,2,6,6-tetramethyl-piperidine-1-oxyl, 2,2,6,6-tetramethyl-piperidine-1-oxyl-4-sulfate, 4-oxo-2,2,6,6-tetramethyl-piperidine, 4-alkoxy-2,2,6,6-tetramethyl-piperidine and mixtures thereof.
Claim 4
Dependent Claim
24 words
The process of claim 2 wherein the stable free radical nitroxide is selected from the group consisting of 2,2,6,6-tetramethyl-piperidine-1-oxyl, 2,2,6,6-tetramethyl-piperidine-1-oxyl-4-sulfate, 4-alkoxy-2,2,6,6-tetramethyl-piperidine-1-oxyl and mixtures thereof.
Claim 5
Dependent Claim
24 words
The process of claim 1 wherein said nitric acid has a concentration in the range of from about 50 percent to about 100 percent.
Claim 6
Dependent Claim
16 words
The process of claim 4 wherein said nitric acid has a concentration of about 70 percent.
Claim 7
Dependent Claim
32 words
The process of claim 1 wherein the amount of nitric acid is in the range of from about 5 mole percent to about 100 mole percent, basis the number of moles alkoxyalkanol.
Claim 8
Dependent Claim
28 words
The process of claim 1 wherein said alkoxyalkanol is contacted with said stable free radical nitroxide, followed by the addition thereto of said nitric acid and said oxidant.
Claim 9
Dependent Claim
35 words
The process of claim 7 wherein the amount of stable free radical nitroxide is in the range of from about 1 mole percent to about 50 mole percent, basis the number of moles of alkoxyalkanol.
Claim 10
Dependent Claim
35 words
The process of claim 8 wherein the amount of stable free radical nitroxide is in the range of from about 5 mole percent to about 20 mole percent, basis the number of moles of alkoxyalkanol.
Claim 11
Dependent Claim
33 words
The process of claim 7 wherein the amount of nitric acid is in the range of from about 5 mole percent to about 100 mole percent, basis the number of moles of alkoxyalkanol.
Claim 12
Dependent Claim
12 words
The process of claim 1 wherein said oxidant is an oxygen-containing gas.
Claim 13
Dependent Claim
21 words
The process of claim 11 wherein said oxygen containing gas is selected from the group consisting of pure oxygen and air.
Claim 14
Dependent Claim
12 words
The process of claim 12 wherein said oxygen-containing gas is pure oxygen.
Claim 15
Dependent Claim
30 words
The process of claim 1 wherein said process is carried out at a temperature in the range of from about 20° C. to about 70° C. and at atmospheric pressure.
Claim 16
Dependent Claim
30 words
The process of claim 14 wherein said process is carried out at a temperature in the range of from about 40° C. to about 60° C. and at atmospheric pressure.
References Cited (Backward Citations)
US4620033A
Cited
JPH0596516A
Cited
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