US4159991A
Expired / Lapsed
US
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Acyloxy-N,N'-diacylmalonamides and methods for their preparation
Assignee: Produits Chimiques Ugine Kuhlmann
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Filing: 1977-08-22
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Granted: 1979-07-03
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Expires: 1997-08-22
Abstract
Abstract α-Acyloxy-N,N'-diacylmalonamides of the formula ##STR1## wherein R 1 , R 2 , R 3 , and R 4 are the same or different and are hydrogen, straight chain or branched alkyl radicals having from one to eleven carbon atoms, or hydrocarbon radicals with six to twelve carbon atoms and comprising at least one aromatic ring, are novel compounds prepared by the action of a mixture of carboxylic acids R 3 COOH and R 4 COOH upon an α-acyloxymalononitrile, R 1 COO--C(CN) 2 --R 2 , in the presence of an acid catalyst and are useful as intermediates in organic synthesis and low temperature activators in bleaching or scouring compositions.
Inventors
- 👤 Bernard Dubreux
- 👤 Serve Y. Delavarenne
- 👤 Jean-Pierre Schirmann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 06:19
CPC Classifications
C; C07; C07C; C07C235/00; C07C235/88; C07C255/00; C07C237/00; C07C237/52; C11; C11D; C11D3/00; C11D3/39; C11D3/3902; C11D3/3905; C11D3/3907; C11D3/3917
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
55 words
α-Acyloxy-N,N'-diacylmalonamides of the formula ##STR3## wherein R 1 , R 2 , R 3 , and R 4 are the same or different and are hydrogen, straight-chain or branched-chain alkyl radicals having from one to eleven carbon atoms, or hydrocarbon radicals having from six to twelve carbon atoms and containing at least one aromatic ring.
Claim 2
Dependent Claim
55 words
α-Acyloxy-N,N'-diacylmalonamides of the formula ##STR3## wherein R 1 , R 2 , R 3 , and R 4 are the same or different and are hydrogen, straight-chain or branched-chain alkyl radicals having from one to eleven carbon atoms, or hydrocarbon radicals having from six to twelve carbon atoms and containing at least one aromatic ring.
Claim 3
Dependent Claim
42 words
α-Acyloxy-N,N'-diacylmalonamides according to claim 1 wherein at least one radical is substituted by a nitro, hydroxy, alkoxy, carboxylic ester or amide, ether oxide, amino, sulfoxide, sulfone, or sulfonic acid group; by fluorine, chlorine, bromine, or iodine; or by a halogenated hydrocarbon group.
Claim 4
Dependent Claim
15 words
α-Acyloxy-N,N'-diacylmalonamides according to claim 2 wherein the halogenated hydrocarbon group is a halogenated methyl radical.
Claim 5
Dependent Claim
12 words
α-Acyloxy-N,N'-diacylmalonamides according to claim 3 wherein the halogen is chloro or fluoro.
Claim 6
Dependent Claim
14 words
α-Acyloxy-N,N'-diacylmalonamides according to claim 4 wherein the halogenated methyl radical is trifluoromethyl or trichloromethyl.
Claim 7
Dependent Claim
47 words
A process for preparation of the acyloxydiacylmalonamides of claim 1 which comprises reacting an α-acyloxymalononitrile having the formula R 1 COO--C(CN) 2 --R 2 with at least one carboxylic acid having the formula R 3 COOH or R 4 COOH in the presence of an acid catalyst.
Claim 8
Dependent Claim
51 words
A process according to claim 6 wherein the α-acyloxymalononitrile is produced in situ by the reaction of hydrogen cyanide or a metal cyanide with a carboxylic acid anhydride to form the nitrile and carboxylic acid and wherein the carboxylic acid is reacted with the nitrile upon addition of the acid catalyst.
Claim 9
Dependent Claim
39 words
A process according to claim 7 wherein the anhydride is a simple or mixed anhydride of formic, acetic, propionic, butyric, isobutyric, valeric, caproic, heptanoic, caprylic, capric, lauric, stearic, benzoic, phenylacetic, toluic, naphthoic, mono-, di- or trifluoro, or -chloroacetic acids.
Claim 10
Dependent Claim
42 words
A process according to claim 6 wherein the carboxylic acid is formic, acetic, propionic, butyric, isobutyric, valeric, caproic, heptanoic, caprylic, capric, lauric, stearic, benzoic, phenylacetic, toluic, naphthoic, mono-, di- or trifluoro, or -chloroacetic acid or a mixture of two or more thereof.
Claim 11
Dependent Claim
29 words
A process according to claim 6 wherein the acid catalyst is perchloric, hydrochloric, hydrobromic, phosphoric, polyphosphoric, paratoluene sulfonic, or sulfuric acid, or aluminum chloride, zinc chloride, or boron trifluoride.
Claim 12
Dependent Claim
26 words
A process according to claim 6 wherein the catalyst used is added at the rate of 0.01 to 10% by weight of the total reaction mixture.
Claim 13
Dependent Claim
19 words
A process according to claim 6 wherein the reaction is performed at a temperature between 0° and 100° C.
References Cited (Backward Citations)
US808748A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-07-02 | 1983-01-01 | 1983-07-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-07-02 | 1987-01-01 | 1987-07-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-07-02 | 1991-01-01 | 1991-07-03 | $7700.00 | Window Closed / Lapsed |