US5175359A
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: 1992-12-29
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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 20, which comprises reacting the corresponding alkoxyalkanol with a solubilized 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, a NO x -generating compound selected from the group consisting of an alkali metal nitrosodisulfonate, nitric acid, nitrous acid and mixtures thereof, and a chloride ion-containing compound 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 17:26
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/16; C07C51/21; C07C51/23; C07C51/235; C07C51/27
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
172 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 20, which comprises reacting the corresponding alkoxyalkanol with a solubilized 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, a NO x -generating compound selected from the group consisting of an alkali metal nitrosodisulfonate, nitric acid, nitrous acid and mixtures thereof, and a chloride ion-containing compound 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
172 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 20, which comprises reacting the corresponding alkoxyalkanol with a solubilized 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, a NO x -generating compound selected from the group consisting of an alkali metal nitrosodisulfonate, nitric acid, nitrous acid and mixtures thereof, and a chloride ion-containing compound 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 solubilized stable free radical nitroxide is selected from the group consisting of 2,2,6,6-tetra-methyl-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-alkoxy-2,2,6,6-tetramethyl-piperidine-1-oxyl and mixtures thereof.
Claim 4
Dependent Claim
25 words
The process of claim 2 wherein the solubilized 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
29 words
The process of claim 1 wherein said NO x -generating compound is an alkali metal nitrosodisulfonate selected from the group consisting of potassium nitrosodisulfonate, sodium nitrosodisulfonate, and mixtures thereof.
Claim 6
Dependent Claim
16 words
The process of claim 4 wherein said NO x -generating compound is an alkali metal nitrosodisulfonate.
Claim 7
Dependent Claim
13 words
The process of claim 5 wherein said alkali metal nitrosodisulfonate is potassium nitrosodisulfonate.
Claim 8
Dependent Claim
14 words
The process of claim 1 wherein said NO x -generating compound is nitric acid.
Claim 9
Dependent Claim
30 words
The process of claim 7 wherein said nitric acid has a concentration in the range of from about 5 mole percent to about 100 mole percent, basis the starting alkoxyalkanol.
Claim 10
Dependent Claim
31 words
The process of claim 1 wherein said chloride ion-containing compound is selected from the group consisting of a quaternary alkyl chloride, a tetraalkyl chloride, an alkali metal chloride and mixtures thereof.
Claim 11
Dependent Claim
27 words
The process of claim 9 wherein said chloride ion-containing compound is selected from the group consisting of tricaprylylmethyl ammonium chloride, sodium chloride, potassium chloride and mixtures thereof.
Claim 12
Dependent Claim
35 words
The process of claim wherein said alkoxyalkanol is contacted with said solubilized stable free radical nitroxide and said chloride ion-containing compound, followed by the addition thereto of said NO x -generating compound and said oxidant.
Claim 13
Dependent Claim
37 words
The process of claim 11 wherein the amount of solubilized stable free radical nitroxide is in the range of from about 1 mole percent to about 25 mole percent, basis the number of moles of the alkoxyalkanol.
Claim 14
Dependent Claim
37 words
The process of claim 12 wherein the amount of solubilized 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 the alkoxyalkanol.
Claim 15
Dependent Claim
12 words
The process of claim 1 wherein said oxidant is an oxygen-containing gas.
Claim 16
Dependent Claim
21 words
The process of claim 14 wherein said oxygen containing gas is selected from the group consisting of pure oxygen and air.
Claim 17
Dependent Claim
12 words
The process of claim 15 wherein said oxygen-containing gas is pure oxygen.
Claim 18
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 19
Dependent Claim
30 words
The process of claim 17 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)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-12-29 | 1996-06-29 | 1996-12-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-12-29 | 2000-06-29 | 2000-12-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-12-29 | 2004-06-29 | 2004-12-29 | $7700.00 | Window Closed / Lapsed |