US3950388A
Expired / Lapsed
US
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Process for making hydroxyether carboxylates
Assignee: Monsanto Co
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Filing: 1974-05-24
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Granted: 1976-04-13
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Expires: 1994-05-24
Abstract
Abstract Organic compounds having a substituent represented by the formula COOMCOOM ¦¦ -O-C---O--CH2 ¦ COOM wherein M is alkali metal or ammonium which are useful complexing agents for metal and/or alkaline earth metal ions are prepared by reaction of a conjugate base of a hemiketal of a ketomalonic acid diester and an alcohol with a bromo or iodo acetate ester and saponifying the resulting product.
Inventors
- 👤 Kent P. Lannert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 19:04
CPC Classifications
C; C11; C11D; C11D3/00; C11D3/16; C11D3/20; C11D3/2075; C11D3/2089; C07; C07C; C07C51/00; C07C51/41; C07C51/412
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
144 words
A process for making organic compounds having a substituent represented by the formula ##EQU42## wherein M is alkali metal or ammonium and acids or esters thereof, said process comprising reacting a conjugate base of a hemiketal of a ketomalonic acid diester and an alcohol having an active alcoholic hydroxy group with a bromo or iodo acetate ester to yield the ester form of said organic compounds; and, when the alkali metal salt form of said organic compounds is desired, reacting said ester form with an alkali metal hydroxide to yield said alkali metal salt form; and, when the acid form of said organic compounds is desired, acidulating said alkali metal salt form to yield said acid form; and, when the ammonium salt form of said organic compounds is desired, reacting said acid form with ammonia or ammonium hydroxide to yield said ammonium salt form.
Claim 2
Dependent Claim
144 words
A process for making organic compounds having a substituent represented by the formula ##EQU42## wherein M is alkali metal or ammonium and acids or esters thereof, said process comprising reacting a conjugate base of a hemiketal of a ketomalonic acid diester and an alcohol having an active alcoholic hydroxy group with a bromo or iodo acetate ester to yield the ester form of said organic compounds; and, when the alkali metal salt form of said organic compounds is desired, reacting said ester form with an alkali metal hydroxide to yield said alkali metal salt form; and, when the acid form of said organic compounds is desired, acidulating said alkali metal salt form to yield said acid form; and, when the ammonium salt form of said organic compounds is desired, reacting said acid form with ammonia or ammonium hydroxide to yield said ammonium salt form.
Claim 3
Dependent Claim
47 words
The process of claim 1 wherein said conjugate base of a hemiketal of a ketomalonic acid diester and an alcohol having an active alcoholic hydroxy group is prepared by reacting a conjugate base of an alcohol having an active alcoholic hydroxy group with a ketomalonic acid diester.
Claim 4
Dependent Claim
64 words
The process of claim 1 wherein said conjugate base of a hemiketal of a ketomalonic acid diester and an alcohol having an active alcoholic hydroxy group is prepared by reacting an alcohol having an active alcoholic hydroxy group with a ketomalonic acid diester to yield a hemiketal and reacting said kemiketal with a base sufficiently strong to convert said hemiketal to its conjugate base.
Claim 5
Dependent Claim
13 words
A process according to claim 1 wherein said alcohol is an aliphatic alcohol.
Claim 6
Dependent Claim
13 words
A process according to claim 1 wherein said alcohol is an alicyclic alcohol.
Claim 7
Dependent Claim
13 words
A process according to claim 1 wherein said alcohol is an aromatic alcohol.
Claim 8
Dependent Claim
14 words
A process according to claim 1 wherein said alcohol is an alkyl aromatic alcohol.
Claim 9
Dependent Claim
13 words
A process according to claim 1 wherein said alcohol is a monohydroxy alcohol.
Claim 10
Dependent Claim
13 words
A process according to claim 1 wherein said alcohol is a polyhydroxy alcohol.
Claim 11
Dependent Claim
13 words
A process according to claim 1 wherein said alcohol is an hydroxy ether.
Claim 12
Dependent Claim
14 words
A process according to claim 1 wherein said alcohol is a poly(alkylene oxide) alcohol.
Claim 13
Dependent Claim
29 words
A process according to claim 1 wherein said alcohol is represented by the formula C n H 2n -1 OH wherein n is an integer from 1 to 20.
Claim 14
Dependent Claim
11 words
A process according to claim 1 wherein said alcohol is methanol.
Claim 15
Dependent Claim
11 words
A process according to claim 1 wherein said alcohol is ethanol.
Claim 16
Dependent Claim
23 words
A process according to claim 1 wherein said alcohol is represented by the formula ##SPC1## m being an integer from 5 to 20.
Claim 17
Dependent Claim
171 words
A process for making an organic compound represented by the formula ##EQU43## wherein x is an integer from 1 to 2 and m is alkali metal or ammonium and acids and esters thereof, said process comprising reacting an alcohol C.sub.x H.sub.2x.sub.+1 OH conjugate base represented by the formula C.sub.x H.sub.2x O.sup.- with a ketomalonic acid diester represented by the formula ##EQU44## to form the hemiketal conjugate base ##EQU45## and reacting said hemiketal conjugate base with a haloacetate represented by the formula ZCH.sub.2 COOC.sub.x H.sub.2x.sub.+1 wherein Z is iodine or bromine to form the ester form of said organic compound; and, when the alkali metal salt form of said organic compound is desired, reacting said ester form with an alkali metal hydroxide to yield said alkali metal salt form; and, when the said form of said organic compound is desired, acidulating said alkali metal salt form to yield said acid form; and, when the ammonium salt form of said organic compound is desired, reacting said acid form with ammonia or ammonium hydroxide.
Claim 18
Dependent Claim
171 words
A process for making an organic compound represented by the formula ##EQU43## wherein x is an integer from 1 to 2 and m is alkali metal or ammonium and acids and esters thereof, said process comprising reacting an alcohol C.sub.x H.sub.2x.sub.+1 OH conjugate base represented by the formula C.sub.x H.sub.2x O.sup.- with a ketomalonic acid diester represented by the formula ##EQU44## to form the hemiketal conjugate base ##EQU45## and reacting said hemiketal conjugate base with a haloacetate represented by the formula ZCH.sub.2 COOC.sub.x H.sub.2x.sub.+1 wherein Z is iodine or bromine to form the ester form of said organic compound; and, when the alkali metal salt form of said organic compound is desired, reacting said ester form with an alkali metal hydroxide to yield said alkali metal salt form; and, when the said form of said organic compound is desired, acidulating said alkali metal salt form to yield said acid form; and, when the ammonium salt form of said organic compound is desired, reacting said acid form with ammonia or ammonium hydroxide.
References Cited (Backward Citations)
US3704320A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-04-13 | 1979-10-13 | 1980-04-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-04-13 | 1983-10-13 | 1984-04-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-04-13 | 1987-10-13 | 1988-04-13 | $7700.00 | Window Closed / Lapsed |